diff --git a/backend/migrations/004_add_books_table.sql b/backend/migrations/004_add_books_table.sql
new file mode 100644
index 0000000..7b7165d
--- /dev/null
+++ b/backend/migrations/004_add_books_table.sql
@@ -0,0 +1,50 @@
+-- 서적 테이블 및 관계 추가
+-- 2025-08-22: 서적 그룹화 기능 추가
+
+-- 서적 테이블 생성
+CREATE TABLE IF NOT EXISTS books (
+    id UUID PRIMARY KEY DEFAULT gen_random_uuid(),
+    title VARCHAR(500) NOT NULL,
+    author VARCHAR(200),
+    publisher VARCHAR(200),
+    isbn VARCHAR(20) UNIQUE,
+    description TEXT,
+    language VARCHAR(10) DEFAULT 'ko',
+    total_pages INTEGER DEFAULT 0,
+    cover_image_path VARCHAR(500),
+    is_public BOOLEAN DEFAULT true,
+    tags VARCHAR(1000),
+    created_at TIMESTAMP WITH TIME ZONE DEFAULT CURRENT_TIMESTAMP,
+    updated_at TIMESTAMP WITH TIME ZONE
+);
+
+-- 인덱스 생성
+CREATE INDEX IF NOT EXISTS idx_books_title ON books(title);
+CREATE INDEX IF NOT EXISTS idx_books_author ON books(author);
+CREATE INDEX IF NOT EXISTS idx_books_created_at ON books(created_at);
+
+-- documents 테이블에 book_id 컬럼 추가
+ALTER TABLE documents ADD COLUMN IF NOT EXISTS book_id UUID;
+
+-- 외래키 제약조건 추가
+ALTER TABLE documents ADD CONSTRAINT IF NOT EXISTS fk_documents_book_id 
+    FOREIGN KEY (book_id) REFERENCES books(id) ON DELETE SET NULL;
+
+-- book_id 인덱스 생성
+CREATE INDEX IF NOT EXISTS idx_documents_book_id ON documents(book_id);
+
+-- 업데이트 트리거 함수 생성 (updated_at 자동 업데이트)
+CREATE OR REPLACE FUNCTION update_updated_at_column()
+RETURNS TRIGGER AS $$
+BEGIN
+    NEW.updated_at = CURRENT_TIMESTAMP;
+    RETURN NEW;
+END;
+$$ language 'plpgsql';
+
+-- books 테이블에 업데이트 트리거 추가
+DROP TRIGGER IF EXISTS update_books_updated_at ON books;
+CREATE TRIGGER update_books_updated_at
+    BEFORE UPDATE ON books
+    FOR EACH ROW
+    EXECUTE FUNCTION update_updated_at_column();
diff --git a/backend/src/api/routes/book_categories.py b/backend/src/api/routes/book_categories.py
new file mode 100644
index 0000000..32d83a8
--- /dev/null
+++ b/backend/src/api/routes/book_categories.py
@@ -0,0 +1,155 @@
+from fastapi import APIRouter, Depends, HTTPException, status
+from sqlalchemy.ext.asyncio import AsyncSession
+from sqlalchemy import select, func, update
+from typing import List
+from uuid import UUID
+
+from ...core.database import get_db
+from ..dependencies import get_current_active_user
+from ...models.user import User
+from ...models.book import Book
+from ...models.book_category import BookCategory
+from ...models.document import Document
+from ...schemas.book_category import (
+    CreateBookCategoryRequest, 
+    UpdateBookCategoryRequest, 
+    BookCategoryResponse,
+    UpdateDocumentOrderRequest
+)
+
+router = APIRouter()
+
+@router.post("/", response_model=BookCategoryResponse, status_code=status.HTTP_201_CREATED)
+async def create_book_category(
+    category_data: CreateBookCategoryRequest,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """새로운 서적 소분류 생성"""
+    # 서적 존재 확인
+    book_result = await db.execute(select(Book).where(Book.id == category_data.book_id))
+    book = book_result.scalar_one_or_none()
+    if not book:
+        raise HTTPException(status_code=status.HTTP_404_NOT_FOUND, detail="Book not found")
+    
+    # 권한 확인 (관리자만)
+    if not current_user.is_admin:
+        raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail="Only administrators can create categories")
+    
+    new_category = BookCategory(**category_data.model_dump())
+    db.add(new_category)
+    await db.commit()
+    await db.refresh(new_category)
+    
+    return await _get_category_response(db, new_category)
+
+@router.get("/book/{book_id}", response_model=List[BookCategoryResponse])
+async def get_book_categories(
+    book_id: UUID,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """특정 서적의 소분류 목록 조회"""
+    result = await db.execute(
+        select(BookCategory)
+        .where(BookCategory.book_id == book_id)
+        .order_by(BookCategory.sort_order, BookCategory.name)
+    )
+    categories = result.scalars().all()
+    
+    response_categories = []
+    for category in categories:
+        response_categories.append(await _get_category_response(db, category))
+    return response_categories
+
+@router.put("/{category_id}", response_model=BookCategoryResponse)
+async def update_book_category(
+    category_id: UUID,
+    category_data: UpdateBookCategoryRequest,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """서적 소분류 수정"""
+    if not current_user.is_admin:
+        raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail="Only administrators can update categories")
+    
+    result = await db.execute(select(BookCategory).where(BookCategory.id == category_id))
+    category = result.scalar_one_or_none()
+    if not category:
+        raise HTTPException(status_code=status.HTTP_404_NOT_FOUND, detail="Category not found")
+    
+    for field, value in category_data.model_dump(exclude_unset=True).items():
+        setattr(category, field, value)
+    
+    await db.commit()
+    await db.refresh(category)
+    return await _get_category_response(db, category)
+
+@router.delete("/{category_id}", status_code=status.HTTP_204_NO_CONTENT)
+async def delete_book_category(
+    category_id: UUID,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """서적 소분류 삭제 (포함된 문서들은 미분류로 이동)"""
+    if not current_user.is_admin:
+        raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail="Only administrators can delete categories")
+    
+    result = await db.execute(select(BookCategory).where(BookCategory.id == category_id))
+    category = result.scalar_one_or_none()
+    if not category:
+        raise HTTPException(status_code=status.HTTP_404_NOT_FOUND, detail="Category not found")
+    
+    # 포함된 문서들을 미분류로 이동 (category_id를 NULL로 설정)
+    await db.execute(
+        update(Document)
+        .where(Document.category_id == category_id)
+        .values(category_id=None)
+    )
+    
+    await db.delete(category)
+    await db.commit()
+    return {"message": "Category deleted successfully"}
+
+@router.put("/documents/reorder", status_code=status.HTTP_200_OK)
+async def update_document_order(
+    order_data: UpdateDocumentOrderRequest,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """문서 순서 변경"""
+    if not current_user.is_admin:
+        raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail="Only administrators can reorder documents")
+    
+    # 문서 순서 업데이트
+    for item in order_data.document_orders:
+        document_id = item.get("document_id")
+        sort_order = item.get("sort_order", 0)
+        
+        await db.execute(
+            update(Document)
+            .where(Document.id == document_id)
+            .values(sort_order=sort_order)
+        )
+    
+    await db.commit()
+    return {"message": "Document order updated successfully"}
+
+# Helper function
+async def _get_category_response(db: AsyncSession, category: BookCategory) -> BookCategoryResponse:
+    """BookCategory를 BookCategoryResponse로 변환"""
+    document_count_result = await db.execute(
+        select(func.count(Document.id)).where(Document.category_id == category.id)
+    )
+    document_count = document_count_result.scalar_one()
+    
+    return BookCategoryResponse(
+        id=category.id,
+        book_id=category.book_id,
+        name=category.name,
+        description=category.description,
+        sort_order=category.sort_order,
+        created_at=category.created_at,
+        updated_at=category.updated_at,
+        document_count=document_count
+    )
diff --git a/backend/src/api/routes/books.py b/backend/src/api/routes/books.py
new file mode 100644
index 0000000..dce1034
--- /dev/null
+++ b/backend/src/api/routes/books.py
@@ -0,0 +1,230 @@
+from fastapi import APIRouter, Depends, HTTPException, status, Query
+from sqlalchemy.ext.asyncio import AsyncSession
+from sqlalchemy import select, func, or_
+from sqlalchemy.orm import selectinload
+from typing import List, Optional
+from uuid import UUID
+import difflib # For similarity suggestions
+
+from ...core.database import get_db
+from ..dependencies import get_current_active_user
+from ...models.user import User
+from ...models.book import Book
+from ...models.document import Document
+from ...schemas.book import CreateBookRequest, UpdateBookRequest, BookResponse, BookSearchResponse, BookSuggestionResponse
+
+router = APIRouter()
+
+# Helper to convert Book ORM object to BookResponse
+async def _get_book_response(db: AsyncSession, book: Book) -> BookResponse:
+    document_count_result = await db.execute(
+        select(func.count(Document.id)).where(Document.book_id == book.id)
+    )
+    document_count = document_count_result.scalar_one()
+    return BookResponse(
+        id=book.id,
+        title=book.title,
+        author=book.author,
+        description=book.description,
+        language=book.language,
+        is_public=book.is_public,
+        created_at=book.created_at,
+        updated_at=book.updated_at,
+        document_count=document_count
+    )
+
+@router.post("/", response_model=BookResponse, status_code=status.HTTP_201_CREATED)
+async def create_book(
+    book_data: CreateBookRequest,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """새로운 서적 생성"""
+    # Check if a book with the same title and author already exists for the user
+    existing_book_query = select(Book).where(Book.title == book_data.title)
+    if book_data.author:
+        existing_book_query = existing_book_query.where(Book.author == book_data.author)
+    
+    existing_book = await db.execute(existing_book_query)
+    if existing_book.scalar_one_or_none():
+        raise HTTPException(
+            status_code=status.HTTP_409_CONFLICT,
+            detail="A book with this title and author already exists."
+        )
+
+    new_book = Book(**book_data.model_dump())
+    db.add(new_book)
+    await db.commit()
+    await db.refresh(new_book)
+    return await _get_book_response(db, new_book)
+
+@router.get("/", response_model=List[BookResponse])
+async def get_books(
+    skip: int = 0,
+    limit: int = 50,
+    search: Optional[str] = Query(None, description="Search by book title or author"),
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """모든 서적 목록 조회"""
+    query = select(Book)
+    if search:
+        query = query.where(
+            or_(
+                Book.title.ilike(f"%{search}%"),
+                Book.author.ilike(f"%{search}%")
+            )
+        )
+    
+    # Only show public books or books owned by the current user/admin
+    if not current_user.is_admin:
+        query = query.where(Book.is_public == True) # For simplicity, assuming all books are public for now or user can only see public ones.
+                                                    # In a real app, you'd link books to users.
+    
+    query = query.offset(skip).limit(limit).order_by(Book.title)
+    result = await db.execute(query)
+    books = result.scalars().all()
+
+    response_books = []
+    for book in books:
+        response_books.append(await _get_book_response(db, book))
+    return response_books
+
+@router.get("/{book_id}", response_model=BookResponse)
+async def get_book(
+    book_id: UUID,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """특정 서적 상세 정보 조회"""
+    result = await db.execute(
+        select(Book).where(Book.id == book_id)
+    )
+    book = result.scalar_one_or_none()
+
+    if not book:
+        raise HTTPException(status_code=status.HTTP_404_NOT_FOUND, detail="Book not found")
+    
+    # Access control (simplified)
+    if not book.is_public and not current_user.is_admin:
+        raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail="Not enough permissions to access this book")
+
+    return await _get_book_response(db, book)
+
+@router.put("/{book_id}", response_model=BookResponse)
+async def update_book(
+    book_id: UUID,
+    book_data: UpdateBookRequest,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """서적 정보 업데이트"""
+    if not current_user.is_admin: # Only admin can update books for now
+        raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail="Only administrators can update books")
+
+    result = await db.execute(
+        select(Book).where(Book.id == book_id)
+    )
+    book = result.scalar_one_or_none()
+
+    if not book:
+        raise HTTPException(status_code=status.HTTP_404_NOT_FOUND, detail="Book not found")
+
+    for field, value in book_data.model_dump(exclude_unset=True).items():
+        setattr(book, field, value)
+    
+    await db.commit()
+    await db.refresh(book)
+    return await _get_book_response(db, book)
+
+@router.delete("/{book_id}", status_code=status.HTTP_204_NO_CONTENT)
+async def delete_book(
+    book_id: UUID,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """서적 삭제"""
+    if not current_user.is_admin: # Only admin can delete books for now
+        raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail="Only administrators can delete books")
+
+    result = await db.execute(
+        select(Book).where(Book.id == book_id)
+    )
+    book = result.scalar_one_or_none()
+
+    if not book:
+        raise HTTPException(status_code=status.HTTP_404_NOT_FOUND, detail="Book not found")
+    
+    # Disassociate documents from this book before deleting
+    await db.execute(
+        select(Document).where(Document.book_id == book_id)
+    )
+    documents_to_update = (await db.execute(select(Document).where(Document.book_id == book_id))).scalars().all()
+    for doc in documents_to_update:
+        doc.book_id = None
+    
+    await db.delete(book)
+    await db.commit()
+    return {"message": "Book deleted successfully"}
+
+@router.get("/search/", response_model=List[BookSearchResponse])
+async def search_books(
+    q: str = Query(..., min_length=1, description="Search query for book title or author"),
+    limit: int = Query(10, ge=1, le=100),
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """서적 검색 (제목 또는 저자)"""
+    query = select(Book).where(
+        or_(
+            Book.title.ilike(f"%{q}%"),
+            Book.author.ilike(f"%{q}%")
+        )
+    )
+    if not current_user.is_admin:
+        query = query.where(Book.is_public == True)
+    
+    result = await db.execute(query.limit(limit))
+    books = result.scalars().all()
+
+    response_books = []
+    for book in books:
+        response_books.append(await _get_book_response(db, book))
+    return response_books
+
+@router.get("/suggestions/", response_model=List[BookSuggestionResponse])
+async def get_book_suggestions(
+    title: str = Query(..., min_length=1, description="Book title for suggestions"),
+    limit: int = Query(5, ge=1, le=10),
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """제목 유사도 기반 서적 추천"""
+    all_books_query = select(Book)
+    if not current_user.is_admin:
+        all_books_query = all_books_query.where(Book.is_public == True)
+    
+    all_books_result = await db.execute(all_books_query)
+    all_books = all_books_result.scalars().all()
+
+    suggestions = []
+    for book in all_books:
+        # Calculate similarity score using difflib
+        score = difflib.SequenceMatcher(None, title.lower(), book.title.lower()).ratio()
+        if score > 0.1: # Only consider if there's some similarity
+            suggestions.append({
+                "book": book,
+                "similarity_score": score
+            })
+    
+    # Sort by similarity score in descending order
+    suggestions.sort(key=lambda x: x["similarity_score"], reverse=True)
+    
+    response_suggestions = []
+    for s in suggestions[:limit]:
+        book_response = await _get_book_response(db, s["book"])
+        response_suggestions.append(BookSuggestionResponse(
+            **book_response.model_dump(),
+            similarity_score=s["similarity_score"]
+        ))
+    return response_suggestions
\ No newline at end of file
diff --git a/backend/src/api/routes/documents.py b/backend/src/api/routes/documents.py
index 5ac2639..5ac9386 100644
--- a/backend/src/api/routes/documents.py
+++ b/backend/src/api/routes/documents.py
@@ -8,6 +8,7 @@ from sqlalchemy.orm import selectinload
 from typing import List, Optional
 import os
 import uuid
+from uuid import UUID
 import aiofiles
 from pathlib import Path
 
@@ -15,6 +16,7 @@ from ...core.database import get_db
 from ...core.config import settings
 from ...models.user import User
 from ...models.document import Document, Tag
+from ...models.book import Book
 from ..dependencies import get_current_active_user, get_current_admin_user
 from pydantic import BaseModel
 from datetime import datetime
@@ -38,6 +40,16 @@ class DocumentResponse(BaseModel):
     document_date: Optional[datetime]
     uploader_name: Optional[str]
     tags: List[str] = []
+    
+    # 서적 정보
+    book_id: Optional[str] = None
+    book_title: Optional[str] = None
+    book_author: Optional[str] = None
+    
+    # 소분류 정보
+    category_id: Optional[str] = None
+    category_name: Optional[str] = None
+    sort_order: int = 0
 
     class Config:
         from_attributes = True
@@ -77,7 +89,9 @@ async def list_documents(
     """문서 목록 조회"""
     query = select(Document).options(
         selectinload(Document.uploader),
-        selectinload(Document.tags)
+        selectinload(Document.tags),
+        selectinload(Document.book),  # 서적 정보 추가
+        selectinload(Document.category)  # 소분류 정보 추가
     )
     
     # 권한 필터링 (관리자가 아니면 공개 문서 + 자신이 업로드한 문서만)
@@ -126,13 +140,108 @@ async def list_documents(
             updated_at=doc.updated_at,
             document_date=doc.document_date,
             uploader_name=doc.uploader.full_name or doc.uploader.email,
-            tags=[tag.name for tag in doc.tags]
+            tags=[tag.name for tag in doc.tags],
+            # 서적 정보 추가
+            book_id=str(doc.book.id) if doc.book else None,
+            book_title=doc.book.title if doc.book else None,
+            book_author=doc.book.author if doc.book else None,
+            # 소분류 정보 추가
+            category_id=str(doc.category.id) if doc.category else None,
+            category_name=doc.category.name if doc.category else None,
+            sort_order=doc.sort_order
         )
         response_data.append(doc_data)
     
     return response_data
 
 
+@router.get("/hierarchy/structured", response_model=dict)
+async def get_documents_by_hierarchy(
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """계층구조별 문서 조회 (서적 > 소분류 > 문서)"""
+    # 모든 문서 조회 (기존 로직 재사용)
+    query = select(Document).options(
+        selectinload(Document.uploader),
+        selectinload(Document.tags),
+        selectinload(Document.book),
+        selectinload(Document.category)
+    )
+    
+    # 권한 필터링
+    if not current_user.is_admin:
+        query = query.where(
+            or_(
+                Document.is_public == True,
+                Document.uploaded_by == current_user.id
+            )
+        )
+    
+    # 정렬: 서적별 > 소분류별 > 문서 순서별
+    query = query.order_by(
+        Document.book_id.nulls_last(),  # 서적 있는 것 먼저
+        Document.category_id.nulls_last(),  # 소분류 있는 것 먼저
+        Document.sort_order,
+        Document.created_at.desc()
+    )
+    
+    result = await db.execute(query)
+    documents = result.scalars().all()
+    
+    # 계층구조로 그룹화
+    hierarchy = {
+        "books": {},  # 서적별 그룹
+        "uncategorized": []  # 미분류 문서들
+    }
+    
+    for doc in documents:
+        doc_data = {
+            "id": str(doc.id),
+            "title": doc.title,
+            "description": doc.description,
+            "created_at": doc.created_at.isoformat(),
+            "uploader_name": doc.uploader.full_name or doc.uploader.email,
+            "tags": [tag.name for tag in doc.tags],
+            "sort_order": doc.sort_order,
+            "book_id": str(doc.book.id) if doc.book else None,
+            "book_title": doc.book.title if doc.book else None,
+            "category_id": str(doc.category.id) if doc.category else None,
+            "category_name": doc.category.name if doc.category else None
+        }
+        
+        if doc.book:
+            # 서적이 있는 문서
+            book_id = str(doc.book.id)
+            if book_id not in hierarchy["books"]:
+                hierarchy["books"][book_id] = {
+                    "id": book_id,
+                    "title": doc.book.title,
+                    "author": doc.book.author,
+                    "categories": {},
+                    "uncategorized_documents": []
+                }
+            
+            if doc.category:
+                # 소분류가 있는 문서
+                category_id = str(doc.category.id)
+                if category_id not in hierarchy["books"][book_id]["categories"]:
+                    hierarchy["books"][book_id]["categories"][category_id] = {
+                        "id": category_id,
+                        "name": doc.category.name,
+                        "documents": []
+                    }
+                hierarchy["books"][book_id]["categories"][category_id]["documents"].append(doc_data)
+            else:
+                # 서적은 있지만 소분류가 없는 문서
+                hierarchy["books"][book_id]["uncategorized_documents"].append(doc_data)
+        else:
+            # 서적이 없는 미분류 문서
+            hierarchy["uncategorized"].append(doc_data)
+    
+    return hierarchy
+
+
 @router.post("/", response_model=DocumentResponse)
 async def upload_document(
     title: str = Form(...),
@@ -141,6 +250,7 @@ async def upload_document(
     language: Optional[str] = Form("ko"),
     is_public: bool = Form(False),
     tags: Optional[List[str]] = Form(None),  # 태그 리스트
+    book_id: Optional[str] = Form(None),  # 서적 ID 추가
     html_file: UploadFile = File(...),
     pdf_file: Optional[UploadFile] = File(None),
     current_user: User = Depends(get_current_active_user),
@@ -181,6 +291,21 @@ async def upload_document(
                 content = await pdf_file.read()
                 await f.write(content)
         
+        # 서적 ID 검증 (있는 경우)
+        validated_book_id = None
+        if book_id:
+            try:
+                # UUID 형식 검증 및 서적 존재 확인
+                from uuid import UUID
+                book_uuid = UUID(book_id)
+                book_result = await db.execute(select(Book).where(Book.id == book_uuid))
+                book = book_result.scalar_one_or_none()
+                if book:
+                    validated_book_id = book_uuid
+            except (ValueError, Exception):
+                # 잘못된 UUID 형식이거나 서적이 없으면 무시
+                pass
+
         # 문서 메타데이터 생성
         document = Document(
             id=doc_id,
@@ -193,7 +318,8 @@ async def upload_document(
             uploaded_by=current_user.id,
             original_filename=html_file.filename,
             is_public=is_public,
-            document_date=datetime.fromisoformat(document_date) if document_date else None
+            document_date=datetime.fromisoformat(document_date) if document_date else None,
+            book_id=validated_book_id  # 서적 ID 추가
         )
         
         db.add(document)
@@ -307,6 +433,48 @@ async def get_document(
     )
 
 
+@router.get("/{document_id}/content")
+async def get_document_content(
+    document_id: str,
+    current_user: User = Depends(get_current_active_user),
+    db: AsyncSession = Depends(get_db)
+):
+    """문서 HTML 콘텐츠 조회"""
+    try:
+        doc_uuid = UUID(document_id)
+    except ValueError:
+        raise HTTPException(status_code=400, detail="Invalid document ID format")
+    
+    # 문서 조회
+    query = select(Document).where(Document.id == doc_uuid)
+    result = await db.execute(query)
+    document = result.scalar_one_or_none()
+    
+    if not document:
+        raise HTTPException(status_code=404, detail="Document not found")
+    
+    # 권한 확인
+    if not current_user.is_admin and not document.is_public and document.uploaded_by != current_user.id:
+        raise HTTPException(status_code=403, detail="Access denied")
+    
+    # HTML 파일 읽기
+    import os
+    from fastapi.responses import HTMLResponse
+    
+    # html_path는 이미 전체 경로를 포함하고 있음
+    file_path = document.html_path
+    
+    if not os.path.exists(file_path):
+        raise HTTPException(status_code=404, detail="Document file not found")
+    
+    try:
+        with open(file_path, 'r', encoding='utf-8') as f:
+            content = f.read()
+        return HTMLResponse(content=content)
+    except Exception as e:
+        raise HTTPException(status_code=500, detail=f"Error reading document: {str(e)}")
+
+
 @router.delete("/{document_id}")
 async def delete_document(
     document_id: str,
@@ -323,11 +491,11 @@ async def delete_document(
             detail="Document not found"
         )
     
-    # 권한 확인 (업로더 또는 관리자만)
-    if document.uploaded_by != current_user.id and not current_user.is_admin:
+    # 권한 확인 (관리자만)
+    if not current_user.is_admin:
         raise HTTPException(
             status_code=status.HTTP_403_FORBIDDEN,
-            detail="Not enough permissions"
+            detail="Only administrators can delete documents"
         )
     
     # 파일 삭제
@@ -338,7 +506,23 @@ async def delete_document(
     if document.thumbnail_path and os.path.exists(document.thumbnail_path):
         os.remove(document.thumbnail_path)
     
-    # 데이터베이스에서 삭제
+    # 관련 데이터 먼저 삭제 (외래키 제약 조건 해결)
+    from ...models.highlight import Highlight
+    from ...models.note import Note
+    from ...models.bookmark import Bookmark
+    
+    # 메모 먼저 삭제 (하이라이트를 참조하므로)
+    await db.execute(delete(Note).where(Note.document_id == document_id))
+    
+    # 북마크 삭제
+    await db.execute(delete(Bookmark).where(Bookmark.document_id == document_id))
+    
+    # 마지막으로 하이라이트 삭제
+    await db.execute(delete(Highlight).where(Highlight.document_id == document_id))
+    
+    # 문서-태그 관계 삭제 (Document.tags 관계를 통해 자동 처리됨)
+    
+    # 마지막으로 문서 삭제
     await db.execute(delete(Document).where(Document.id == document_id))
     await db.commit()
     
diff --git a/backend/src/api/routes/highlights.py b/backend/src/api/routes/highlights.py
index d68c240..68d4ca0 100644
--- a/backend/src/api/routes/highlights.py
+++ b/backend/src/api/routes/highlights.py
@@ -36,6 +36,7 @@ class UpdateHighlightRequest(BaseModel):
     """하이라이트 업데이트 요청"""
     highlight_color: Optional[str] = None
     highlight_type: Optional[str] = None
+    note: Optional[str] = None  # 메모 업데이트 지원
 
 
 class HighlightResponse(BaseModel):
@@ -155,63 +156,60 @@ async def get_document_highlights(
     try:
         print(f"DEBUG: Getting highlights for document {document_id}, user {current_user.id}")
         
-        # 임시로 빈 배열 반환 (테스트용)
-        return []
+        # 문서 존재 및 권한 확인
+        result = await db.execute(select(Document).where(Document.id == document_id))
+        document = result.scalar_one_or_none()
         
-        # 원래 코드는 주석 처리
-        # # 문서 존재 및 권한 확인
-        # result = await db.execute(select(Document).where(Document.id == document_id))
-        # document = result.scalar_one_or_none()
-        # 
-        # if not document:
-        #     raise HTTPException(
-        #         status_code=status.HTTP_404_NOT_FOUND,
-        #         detail="Document not found"
-        #     )
-        # 
-        # # 문서 접근 권한 확인
-        # if not document.is_public and document.uploaded_by != current_user.id and not current_user.is_admin:
-        #     raise HTTPException(
-        #         status_code=status.HTTP_403_FORBIDDEN,
-        #         detail="Not enough permissions to access this document"
-        #     )
-        # 
-        # # 사용자의 하이라이트만 조회 (notes 로딩 제거)
-        # result = await db.execute(
-        #     select(Highlight)
-        #     .where(
-        #         and_(
-        #             Highlight.document_id == document_id,
-        #             Highlight.user_id == current_user.id
-        #         )
-        #     )
-        #     .order_by(Highlight.start_offset)
-        # )
-        # highlights = result.scalars().all()
-        # 
-        # # 응답 데이터 변환
-        # response_data = []
-        # for highlight in highlights:
-        #     highlight_data = HighlightResponse(
-        #         id=str(highlight.id),
-        #         user_id=str(highlight.user_id),
-        #         document_id=str(highlight.document_id),
-        #         start_offset=highlight.start_offset,
-        #         end_offset=highlight.end_offset,
-        #         selected_text=highlight.selected_text,
-        #         element_selector=highlight.element_selector,
-        #         start_container_xpath=highlight.start_container_xpath,
-        #         end_container_xpath=highlight.end_container_xpath,
-        #         highlight_color=highlight.highlight_color,
-        #         highlight_type=highlight.highlight_type,
-        #         created_at=highlight.created_at,
-        #         updated_at=highlight.updated_at,
-        #         note=None
-        #     )
-        #     # 메모는 별도 API에서 조회하므로 여기서는 처리하지 않음
-        #     response_data.append(highlight_data)
-        # 
-        # return response_data
+        if not document:
+            raise HTTPException(
+                status_code=status.HTTP_404_NOT_FOUND,
+                detail="Document not found"
+            )
+        
+        # 문서 접근 권한 확인
+        if not document.is_public and document.uploaded_by != current_user.id and not current_user.is_admin:
+            raise HTTPException(
+                status_code=status.HTTP_403_FORBIDDEN,
+                detail="Not enough permissions to access this document"
+            ) 
+        
+        # 사용자의 하이라이트만 조회
+        result = await db.execute(
+            select(Highlight)
+            .where(
+                and_(
+                    Highlight.document_id == document_id,
+                    Highlight.user_id == current_user.id
+                )
+            )
+            .order_by(Highlight.start_offset)
+        )
+        highlights = result.scalars().all()
+        
+        print(f"DEBUG: Found {len(highlights)} highlights for user {current_user.id}")
+        
+        # 응답 데이터 변환
+        response_data = []
+        for highlight in highlights:
+            highlight_data = HighlightResponse(
+                id=str(highlight.id),
+                user_id=str(highlight.user_id),
+                document_id=str(highlight.document_id),
+                start_offset=highlight.start_offset,
+                end_offset=highlight.end_offset,
+                selected_text=highlight.selected_text,
+                element_selector=highlight.element_selector,
+                start_container_xpath=highlight.start_container_xpath,
+                end_container_xpath=highlight.end_container_xpath,
+                highlight_color=highlight.highlight_color,
+                highlight_type=highlight.highlight_type,
+                created_at=highlight.created_at,
+                updated_at=highlight.updated_at,
+                note=None
+            )
+            response_data.append(highlight_data)
+        
+        return response_data
         
     except Exception as e:
         print(f"ERROR in get_document_highlights: {e}")
@@ -288,7 +286,7 @@ async def update_highlight(
     """하이라이트 업데이트"""
     result = await db.execute(
         select(Highlight)
-        .options(selectinload(Highlight.user))
+        .options(selectinload(Highlight.user), selectinload(Highlight.notes))
         .where(Highlight.id == highlight_id)
     )
     highlight = result.scalar_one_or_none()
@@ -312,6 +310,23 @@ async def update_highlight(
     if highlight_data.highlight_type:
         highlight.highlight_type = highlight_data.highlight_type
     
+    # 메모 업데이트 처리
+    if highlight_data.note is not None:
+        if highlight.notes:
+            # 기존 메모 업데이트
+            highlight.notes.content = highlight_data.note
+            highlight.notes.updated_at = datetime.utcnow()
+        else:
+            # 새 메모 생성
+            new_note = Note(
+                user_id=current_user.id,
+                document_id=highlight.document_id,
+                highlight_id=highlight.id,
+                content=highlight_data.note,
+                tags=""
+            )
+            db.add(new_note)
+    
     await db.commit()
     await db.refresh(highlight)
     
diff --git a/backend/src/main.py b/backend/src/main.py
index 4826788..15fed77 100644
--- a/backend/src/main.py
+++ b/backend/src/main.py
@@ -9,7 +9,7 @@ import uvicorn
 
 from .core.config import settings
 from .core.database import init_db
-from .api.routes import auth, users, documents, highlights, notes, bookmarks, search
+from .api.routes import auth, users, documents, highlights, notes, bookmarks, search, books, book_categories
 
 
 @asynccontextmanager
@@ -47,6 +47,8 @@ app.include_router(users.router, prefix="/api/users", tags=["사용자"])
 app.include_router(documents.router, prefix="/api/documents", tags=["문서"])
 app.include_router(highlights.router, prefix="/api/highlights", tags=["하이라이트"])
 app.include_router(notes.router, prefix="/api/notes", tags=["메모"])
+app.include_router(books.router, prefix="/api/books", tags=["서적"])
+app.include_router(book_categories.router, prefix="/api/book-categories", tags=["서적 소분류"])
 app.include_router(bookmarks.router, prefix="/api/bookmarks", tags=["책갈피"])
 app.include_router(search.router, prefix="/api/search", tags=["검색"])
 
diff --git a/backend/src/models/book.py b/backend/src/models/book.py
new file mode 100644
index 0000000..cb0c67a
--- /dev/null
+++ b/backend/src/models/book.py
@@ -0,0 +1,27 @@
+from sqlalchemy import Column, String, DateTime, Text, Boolean
+from sqlalchemy.dialects.postgresql import UUID
+from sqlalchemy.orm import relationship
+from sqlalchemy.sql import func
+import uuid
+
+from ..core.database import Base
+
+class Book(Base):
+    """서적 테이블 (여러 문서를 묶는 단위)"""
+    __tablename__ = "books"
+
+    id = Column(UUID(as_uuid=True), primary_key=True, default=uuid.uuid4)
+    title = Column(String(500), nullable=False, index=True)
+    author = Column(String(255), nullable=True)
+    description = Column(Text, nullable=True)
+    language = Column(String(10), default="ko")
+    is_public = Column(Boolean, default=False)
+    created_at = Column(DateTime(timezone=True), server_default=func.now())
+    updated_at = Column(DateTime(timezone=True), onupdate=func.now())
+
+    # 관계
+    documents = relationship("Document", back_populates="book", cascade="all, delete-orphan")
+    categories = relationship("BookCategory", back_populates="book", cascade="all, delete-orphan", order_by="BookCategory.sort_order")
+
+    def __repr__(self):
+        return f"<Book(title='{self.title}', author='{self.author}')>"
\ No newline at end of file
diff --git a/backend/src/models/book_category.py b/backend/src/models/book_category.py
new file mode 100644
index 0000000..834ac4c
--- /dev/null
+++ b/backend/src/models/book_category.py
@@ -0,0 +1,26 @@
+from sqlalchemy import Column, String, DateTime, Text, Integer, ForeignKey
+from sqlalchemy.dialects.postgresql import UUID
+from sqlalchemy.orm import relationship
+from sqlalchemy.sql import func
+import uuid
+
+from ..core.database import Base
+
+class BookCategory(Base):
+    """서적 소분류 테이블 (서적 내 문서 그룹화)"""
+    __tablename__ = "book_categories"
+
+    id = Column(UUID(as_uuid=True), primary_key=True, default=uuid.uuid4)
+    book_id = Column(UUID(as_uuid=True), ForeignKey('books.id', ondelete='CASCADE'), nullable=False, index=True)
+    name = Column(String(200), nullable=False)  # 소분류 이름 (예: "Chapter 1", "설계 기준", "계산서")
+    description = Column(Text, nullable=True)  # 소분류 설명
+    sort_order = Column(Integer, default=0)  # 소분류 정렬 순서
+    created_at = Column(DateTime(timezone=True), server_default=func.now())
+    updated_at = Column(DateTime(timezone=True), onupdate=func.now())
+
+    # 관계
+    book = relationship("Book", back_populates="categories")
+    documents = relationship("Document", back_populates="category", cascade="all, delete-orphan")
+
+    def __repr__(self):
+        return f"<BookCategory(name='{self.name}', book='{self.book.title if self.book else None}')>"
diff --git a/backend/src/models/document.py b/backend/src/models/document.py
index 68252f3..583edcb 100644
--- a/backend/src/models/document.py
+++ b/backend/src/models/document.py
@@ -24,7 +24,10 @@ class Document(Base):
     __tablename__ = "documents"
 
     id = Column(UUID(as_uuid=True), primary_key=True, default=uuid.uuid4)
+    book_id = Column(UUID(as_uuid=True), ForeignKey('books.id'), nullable=True, index=True)  # 서적 ID
+    category_id = Column(UUID(as_uuid=True), ForeignKey('book_categories.id'), nullable=True, index=True)  # 소분류 ID
     title = Column(String(500), nullable=False, index=True)
+    sort_order = Column(Integer, default=0)  # 문서 정렬 순서 (소분류 내에서)
     description = Column(Text, nullable=True)
     
     # 파일 정보
@@ -51,6 +54,8 @@ class Document(Base):
     document_date = Column(DateTime(timezone=True), nullable=True)  # 문서 작성일 (사용자 입력)
     
     # 관계
+    book = relationship("Book", back_populates="documents")  # 서적 관계
+    category = relationship("BookCategory", back_populates="documents")  # 소분류 관계
     uploader = relationship("User", backref="uploaded_documents")
     tags = relationship("Tag", secondary=document_tags, back_populates="documents")
     highlights = relationship("Highlight", back_populates="document", cascade="all, delete-orphan")
diff --git a/backend/src/schemas/book.py b/backend/src/schemas/book.py
new file mode 100644
index 0000000..8c3c5f9
--- /dev/null
+++ b/backend/src/schemas/book.py
@@ -0,0 +1,32 @@
+from pydantic import BaseModel, Field
+from typing import Optional, List
+from datetime import datetime
+from uuid import UUID
+
+class BookBase(BaseModel):
+    title: str = Field(..., min_length=1, max_length=500)
+    author: Optional[str] = Field(None, max_length=255)
+    description: Optional[str] = None
+    language: str = Field("ko", max_length=10)
+    is_public: bool = False
+
+class CreateBookRequest(BookBase):
+    pass
+
+class UpdateBookRequest(BookBase):
+    pass
+
+class BookResponse(BookBase):
+    id: UUID
+    created_at: datetime
+    updated_at: Optional[datetime]
+    document_count: int = 0 # 문서 개수 추가
+
+    class Config:
+        from_attributes = True
+
+class BookSearchResponse(BookResponse):
+    pass
+
+class BookSuggestionResponse(BookResponse):
+    similarity_score: float = Field(..., ge=0.0, le=1.0)
\ No newline at end of file
diff --git a/backend/src/schemas/book_category.py b/backend/src/schemas/book_category.py
new file mode 100644
index 0000000..cdcaf4c
--- /dev/null
+++ b/backend/src/schemas/book_category.py
@@ -0,0 +1,31 @@
+from pydantic import BaseModel, Field
+from typing import Optional, List
+from datetime import datetime
+from uuid import UUID
+
+class BookCategoryBase(BaseModel):
+    name: str = Field(..., min_length=1, max_length=200)
+    description: Optional[str] = None
+    sort_order: int = Field(0, ge=0)
+
+class CreateBookCategoryRequest(BookCategoryBase):
+    book_id: UUID
+
+class UpdateBookCategoryRequest(BaseModel):
+    name: Optional[str] = Field(None, min_length=1, max_length=200)
+    description: Optional[str] = None
+    sort_order: Optional[int] = Field(None, ge=0)
+
+class BookCategoryResponse(BookCategoryBase):
+    id: UUID
+    book_id: UUID
+    created_at: datetime
+    updated_at: Optional[datetime]
+    document_count: int = 0  # 포함된 문서 수
+
+    class Config:
+        from_attributes = True
+
+class UpdateDocumentOrderRequest(BaseModel):
+    document_orders: List[dict] = Field(..., description="문서 ID와 순서 정보")
+    # 예: [{"document_id": "uuid", "sort_order": 1}, ...]
diff --git a/frontend/hierarchy.html b/frontend/hierarchy.html
new file mode 100644
index 0000000..af7c5b4
--- /dev/null
+++ b/frontend/hierarchy.html
@@ -0,0 +1,677 @@
+<!DOCTYPE html>
+<html lang="ko">
+<head>
+    <meta charset="UTF-8">
+    <meta name="viewport" content="width=device-width, initial-scale=1.0">
+    <title>문서 관리 시스템 - 계층구조</title>
+    <script src="https://cdn.tailwindcss.com"></script>
+    <script src="https://unpkg.com/alpinejs@3.x.x/dist/cdn.min.js" defer></script>
+    <link href="https://cdnjs.cloudflare.com/ajax/libs/font-awesome/6.0.0/css/all.min.css" rel="stylesheet">
+    <style>
+        /* 드래그 앤 드롭 스타일 */
+        .draggable {
+            cursor: move;
+            transition: all 0.2s ease;
+        }
+        .draggable:hover {
+            transform: translateY(-1px);
+            box-shadow: 0 4px 12px rgba(0, 0, 0, 0.15);
+        }
+        .drag-over {
+            border: 2px dashed #3b82f6;
+            background-color: #eff6ff;
+        }
+        .tree-item {
+            position: relative;
+        }
+        .tree-item::before {
+            content: '';
+            position: absolute;
+            left: -12px;
+            top: 0;
+            bottom: 0;
+            width: 1px;
+            background: #e5e7eb;
+        }
+        .tree-item:last-child::before {
+            height: 20px;
+        }
+        .tree-item::after {
+            content: '';
+            position: absolute;
+            left: -12px;
+            top: 20px;
+            width: 12px;
+            height: 1px;
+            background: #e5e7eb;
+        }
+        .sidebar-scroll {
+            scrollbar-width: thin;
+            scrollbar-color: #cbd5e1 #f1f5f9;
+        }
+        .sidebar-scroll::-webkit-scrollbar {
+            width: 6px;
+        }
+        .sidebar-scroll::-webkit-scrollbar-track {
+            background: #f1f5f9;
+        }
+        .sidebar-scroll::-webkit-scrollbar-thumb {
+            background: #cbd5e1;
+            border-radius: 3px;
+        }
+        
+        /* 하이라이트 스타일 */
+        .highlight {
+            border-radius: 2px;
+            padding: 1px 2px;
+            margin: 0 1px;
+            transition: all 0.2s ease;
+        }
+        .highlight:hover {
+            opacity: 0.8;
+            transform: scale(1.02);
+        }
+        
+        /* 텍스트 선택 시 하이라이트 메뉴 */
+        .highlight-menu {
+            animation: fadeInUp 0.2s ease-out;
+            box-shadow: 0 10px 25px rgba(0, 0, 0, 0.3) !important;
+            border: 3px solid #3b82f6 !important;
+            background: white !important;
+            z-index: 99999 !important;
+        }
+        
+        @keyframes fadeInUp {
+            from {
+                opacity: 0;
+                transform: translateY(10px);
+            }
+            to {
+                opacity: 1;
+                transform: translateY(0);
+            }
+        }
+        
+        /* 문서 콘텐츠 영역 */
+        .prose {
+            user-select: text;
+            -webkit-user-select: text;
+            -moz-user-select: text;
+            -ms-user-select: text;
+        }
+    </style>
+</head>
+<body class="bg-gray-50" x-data="hierarchyApp()" x-init="init()">
+    <!-- 헤더 -->
+    <header class="bg-white shadow-sm border-b">
+        <div class="px-6 py-4">
+            <div class="flex items-center justify-between">
+                <div class="flex items-center space-x-4">
+                    <h1 class="text-2xl font-bold text-gray-900">📚 문서 관리 시스템</h1>
+                    <div class="flex space-x-2">
+                        <a href="index.html" class="px-3 py-1 text-sm bg-gray-100 text-gray-600 rounded-full hover:bg-gray-200">그리드 뷰</a>
+                        <span class="px-3 py-1 text-sm bg-blue-100 text-blue-800 rounded-full">계층구조 뷰</span>
+                    </div>
+                </div>
+                
+                <div class="flex items-center space-x-4">
+                    <!-- 검색 -->
+                    <div class="relative" x-show="currentUser">
+                        <i class="fas fa-search absolute left-3 top-1/2 transform -translate-y-1/2 text-gray-400"></i>
+                        <input 
+                            type="text" 
+                            x-model="searchQuery" 
+                            @input="searchDocuments"
+                            placeholder="문서, 메모 검색..." 
+                            class="w-80 pl-10 pr-4 py-2 border border-gray-300 rounded-lg focus:outline-none focus:ring-2 focus:ring-blue-500"
+                        >
+                    </div>
+                    
+                    <!-- 사용자 메뉴 -->
+                    <div x-show="currentUser" class="flex items-center space-x-3">
+                        <span class="text-sm text-gray-600" x-text="currentUser?.full_name || currentUser?.email"></span>
+                        <button @click="logout()" class="text-sm text-red-600 hover:text-red-800">로그아웃</button>
+                    </div>
+                    
+                    <!-- 로그인 버튼 -->
+                    <button x-show="!currentUser" @click="openLoginModal()" class="px-4 py-2 bg-blue-600 text-white rounded-lg hover:bg-blue-700">
+                        로그인
+                    </button>
+                </div>
+            </div>
+        </div>
+    </header>
+
+    <!-- 메인 컨테이너 -->
+    <div class="flex h-screen pt-16">
+        <!-- 사이드바 -->
+        <aside class="w-80 bg-white shadow-lg border-r flex flex-col">
+            <!-- 사이드바 헤더 -->
+            <div class="p-4 border-b bg-gray-50">
+                <div class="flex items-center justify-between">
+                    <h2 class="font-semibold text-gray-900">📖 문서 구조</h2>
+                    <div class="flex space-x-2">
+                        <button 
+                            @click="showUploadModal = true"
+                            x-show="currentUser"
+                            class="p-2 text-blue-600 hover:bg-blue-50 rounded-lg"
+                            title="문서 업로드"
+                        >
+                            <i class="fas fa-plus"></i>
+                        </button>
+                        <button 
+                            @click="refreshHierarchy()"
+                            class="p-2 text-gray-600 hover:bg-gray-100 rounded-lg"
+                            title="새로고침"
+                        >
+                            <i class="fas fa-sync-alt"></i>
+                        </button>
+                    </div>
+                </div>
+            </div>
+            
+            <!-- 트리 구조 -->
+            <div class="flex-1 overflow-y-auto sidebar-scroll p-4">
+                <div x-show="loading" class="text-center py-8">
+                    <i class="fas fa-spinner fa-spin text-gray-400"></i>
+                    <p class="text-gray-500 mt-2">로딩 중...</p>
+                </div>
+                
+                <div x-show="!loading">
+                    <!-- 서적들 -->
+                    <template x-for="(book, bookId) in hierarchy.books" :key="bookId">
+                        <div class="mb-4">
+                            <!-- 서적 헤더 -->
+                            <div 
+                                class="flex items-center p-3 bg-blue-50 border border-blue-200 rounded-lg cursor-pointer hover:bg-blue-100"
+                                @click="toggleBook(bookId)"
+                            >
+                                <i class="fas fa-book text-blue-600 mr-3"></i>
+                                <div class="flex-1">
+                                    <h3 class="font-medium text-blue-900" x-text="book.title"></h3>
+                                    <p class="text-sm text-blue-700" x-text="book.author || '저자 미상'"></p>
+                                </div>
+                                <i 
+                                    class="fas fa-chevron-down transition-transform duration-200"
+                                    :class="expandedBooks.includes(bookId) ? 'rotate-180' : ''"
+                                ></i>
+                            </div>
+                            
+                            <!-- 서적 내용 -->
+                            <div x-show="expandedBooks.includes(bookId)" class="mt-2 ml-4 space-y-2">
+                                <!-- 소분류들 -->
+                                <template x-for="(category, categoryId) in book.categories" :key="categoryId">
+                                    <div class="tree-item">
+                                        <!-- 소분류 헤더 -->
+                                        <div 
+                                            class="flex items-center p-2 bg-green-50 border border-green-200 rounded cursor-pointer hover:bg-green-100"
+                                            @click="toggleCategory(categoryId)"
+                                        >
+                                            <i class="fas fa-folder text-green-600 mr-2"></i>
+                                            <span class="flex-1 font-medium text-green-900" x-text="category.name"></span>
+                                            <span class="text-xs text-green-700" x-text="`${category.documents.length}개`"></span>
+                                            <i 
+                                                class="fas fa-chevron-down ml-2 transition-transform duration-200"
+                                                :class="expandedCategories.includes(categoryId) ? 'rotate-180' : ''"
+                                            ></i>
+                                        </div>
+                                        
+                                        <!-- 소분류 문서들 -->
+                                        <div x-show="expandedCategories.includes(categoryId)" class="mt-1 ml-4 space-y-1">
+                                            <template x-for="doc in category.documents" :key="doc.id">
+                                                <div 
+                                                    class="flex items-center p-2 bg-white border rounded cursor-pointer hover:bg-gray-50 draggable"
+                                                    @click="openDocument(doc.id)"
+                                                    draggable="true"
+                                                    @dragstart="handleDragStart($event, doc)"
+                                                    @dragover.prevent
+                                                    @drop="handleDrop($event, categoryId)"
+                                                >
+                                                    <i class="fas fa-file-alt text-gray-500 mr-2"></i>
+                                                    <span class="flex-1 text-sm" x-text="doc.title"></span>
+                                                    <div class="flex space-x-1">
+                                                        <button 
+                                                            @click.stop="editDocument(doc)"
+                                                            class="p-1 text-gray-400 hover:text-blue-600"
+                                                            title="편집"
+                                                        >
+                                                            <i class="fas fa-edit text-xs"></i>
+                                                        </button>
+                                                        <button 
+                                                            x-show="currentUser && currentUser.is_admin"
+                                                            @click.stop="deleteDocument(doc.id)"
+                                                            class="p-1 text-gray-400 hover:text-red-600"
+                                                            title="삭제"
+                                                        >
+                                                            <i class="fas fa-trash text-xs"></i>
+                                                        </button>
+                                                    </div>
+                                                </div>
+                                            </template>
+                                        </div>
+                                    </div>
+                                </template>
+                                
+                                <!-- 서적 내 미분류 문서들 -->
+                                <div x-show="book.uncategorized_documents.length > 0" class="tree-item">
+                                    <div 
+                                        class="flex items-center p-2 bg-yellow-50 border border-yellow-200 rounded cursor-pointer hover:bg-yellow-100"
+                                        @click="toggleUncategorizedInBook(bookId)"
+                                    >
+                                        <i class="fas fa-folder-open text-yellow-600 mr-2"></i>
+                                        <span class="flex-1 font-medium text-yellow-900">미분류</span>
+                                        <span class="text-xs text-yellow-700" x-text="`${book.uncategorized_documents.length}개`"></span>
+                                        <i 
+                                            class="fas fa-chevron-down ml-2 transition-transform duration-200"
+                                            :class="expandedUncategorizedInBooks.includes(bookId) ? 'rotate-180' : ''"
+                                        ></i>
+                                    </div>
+                                    
+                                    <div x-show="expandedUncategorizedInBooks.includes(bookId)" class="mt-1 ml-4 space-y-1">
+                                        <template x-for="doc in book.uncategorized_documents" :key="doc.id">
+                                            <div 
+                                                class="flex items-center p-2 bg-white border rounded cursor-pointer hover:bg-gray-50 draggable"
+                                                @click="openDocument(doc.id)"
+                                                draggable="true"
+                                                @dragstart="handleDragStart($event, doc)"
+                                            >
+                                                <i class="fas fa-file-alt text-gray-500 mr-2"></i>
+                                                <span class="flex-1 text-sm" x-text="doc.title"></span>
+                                                <div class="flex space-x-1">
+                                                    <button 
+                                                        @click.stop="editDocument(doc)"
+                                                        class="p-1 text-gray-400 hover:text-blue-600"
+                                                        title="편집"
+                                                    >
+                                                        <i class="fas fa-edit text-xs"></i>
+                                                    </button>
+                                                    <button 
+                                                        x-show="currentUser && currentUser.is_admin"
+                                                        @click.stop="deleteDocument(doc.id)"
+                                                        class="p-1 text-gray-400 hover:text-red-600"
+                                                        title="삭제"
+                                                    >
+                                                        <i class="fas fa-trash text-xs"></i>
+                                                    </button>
+                                                </div>
+                                            </div>
+                                        </template>
+                                    </div>
+                                </div>
+                            </div>
+                        </div>
+                    </template>
+                    
+                    <!-- 전체 미분류 문서들 -->
+                    <div x-show="hierarchy.uncategorized.length > 0" class="mb-4">
+                        <div 
+                            class="flex items-center p-3 bg-gray-100 border border-gray-300 rounded-lg cursor-pointer hover:bg-gray-200"
+                            @click="toggleUncategorized()"
+                        >
+                            <i class="fas fa-folder-open text-gray-600 mr-3"></i>
+                            <div class="flex-1">
+                                <h3 class="font-medium text-gray-900">📄 미분류 문서</h3>
+                                <p class="text-sm text-gray-600" x-text="`${hierarchy.uncategorized.length}개 문서`"></p>
+                            </div>
+                            <i 
+                                class="fas fa-chevron-down transition-transform duration-200"
+                                :class="showUncategorized ? 'rotate-180' : ''"
+                            ></i>
+                        </div>
+                        
+                        <div x-show="showUncategorized" class="mt-2 ml-4 space-y-1">
+                            <template x-for="doc in hierarchy.uncategorized" :key="doc.id">
+                                <div 
+                                    class="flex items-center p-2 bg-white border rounded cursor-pointer hover:bg-gray-50 draggable"
+                                    @click="openDocument(doc.id)"
+                                    draggable="true"
+                                    @dragstart="handleDragStart($event, doc)"
+                                >
+                                    <i class="fas fa-file-alt text-gray-500 mr-2"></i>
+                                    <span class="flex-1 text-sm" x-text="doc.title"></span>
+                                    <div class="flex space-x-1">
+                                        <button 
+                                            @click.stop="editDocument(doc)"
+                                            class="p-1 text-gray-400 hover:text-blue-600"
+                                            title="편집"
+                                        >
+                                            <i class="fas fa-edit text-xs"></i>
+                                        </button>
+                                        <button 
+                                            x-show="currentUser && currentUser.is_admin"
+                                            @click.stop="deleteDocument(doc.id)"
+                                            class="p-1 text-gray-400 hover:text-red-600"
+                                            title="삭제"
+                                        >
+                                            <i class="fas fa-trash text-xs"></i>
+                                        </button>
+                                    </div>
+                                </div>
+                            </template>
+                        </div>
+                    </div>
+                    
+                    <!-- 빈 상태 -->
+                    <div x-show="Object.keys(hierarchy.books).length === 0 && hierarchy.uncategorized.length === 0" class="text-center py-8">
+                        <i class="fas fa-folder-open text-gray-300 text-4xl mb-4"></i>
+                        <p class="text-gray-500">아직 문서가 없습니다.</p>
+                        <button 
+                            x-show="currentUser"
+                            @click="showUploadModal = true"
+                            class="mt-4 px-4 py-2 bg-blue-600 text-white rounded-lg hover:bg-blue-700"
+                        >
+                            첫 문서 업로드하기
+                        </button>
+                    </div>
+                </div>
+            </div>
+        </aside>
+        
+        <!-- 메인 콘텐츠 영역 -->
+        <main class="flex-1 flex flex-col">
+            <!-- 콘텐츠 헤더 -->
+            <div class="bg-white border-b p-4">
+                <div class="flex items-center justify-between">
+                    <div>
+                        <h2 class="text-lg font-semibold text-gray-900" x-text="selectedDocument ? selectedDocument.title : '문서를 선택하세요'"></h2>
+                        <p class="text-sm text-gray-500" x-text="selectedDocument ? `${selectedDocument.book_title || '미분류'} ${selectedDocument.category_name ? '> ' + selectedDocument.category_name : ''}` : '사이드바에서 문서를 클릭하여 내용을 확인하세요'"></p>
+                    </div>
+                    
+                    <div x-show="selectedDocument" class="flex space-x-2">
+                        <button 
+                            @click="toggleHighlightMode()"
+                            class="px-3 py-2 rounded transition-colors"
+                            :class="highlightMode ? 'bg-yellow-500 text-white' : 'text-yellow-600 border border-yellow-600 hover:bg-yellow-50'"
+                        >
+                            <i class="fas fa-highlighter mr-1"></i> 
+                            <span x-text="highlightMode ? '하이라이트 ON' : '하이라이트 OFF'"></span>
+                        </button>
+                        <button 
+                            @click="editDocument(selectedDocument)"
+                            class="px-3 py-2 text-blue-600 border border-blue-600 rounded hover:bg-blue-50"
+                        >
+                            <i class="fas fa-edit mr-1"></i> 편집
+                        </button>
+                        <button 
+                            x-show="currentUser && currentUser.is_admin"
+                            @click="deleteDocument(selectedDocument.id)"
+                            class="px-3 py-2 text-red-600 border border-red-600 rounded hover:bg-red-50"
+                        >
+                            <i class="fas fa-trash mr-1"></i> 삭제
+                        </button>
+                    </div>
+                </div>
+            </div>
+            
+            <!-- 문서 뷰어 -->
+            <div class="flex-1 overflow-auto">
+                <div x-show="!selectedDocument" class="flex items-center justify-center h-full">
+                    <div class="text-center">
+                        <i class="fas fa-file-alt text-gray-300 text-6xl mb-4"></i>
+                        <h3 class="text-xl font-medium text-gray-600 mb-2">문서를 선택하세요</h3>
+                        <p class="text-gray-500">왼쪽 사이드바에서 문서를 클릭하면 내용이 표시됩니다.</p>
+                    </div>
+                </div>
+                
+                <div x-show="selectedDocument && documentContent" class="p-6">
+                    <div x-html="documentContent" class="prose max-w-none"></div>
+                </div>
+                
+                <div x-show="selectedDocument && !documentContent && loadingDocument" class="flex items-center justify-center h-full">
+                    <div class="text-center">
+                        <i class="fas fa-spinner fa-spin text-gray-400 text-3xl mb-4"></i>
+                        <p class="text-gray-500">문서를 불러오는 중...</p>
+                    </div>
+                </div>
+            </div>
+            
+            <!-- 하이라이트 메뉴 (직접 DOM 조작) -->
+            <div 
+                id="highlight-menu"
+                class="fixed top-20 left-1/2 transform -translate-x-1/2 z-50 bg-white border border-gray-300 rounded-lg shadow-lg p-3"
+                style="display: none;"
+            >
+                <div class="text-center mb-2">
+                    <h4 class="font-semibold text-sm">하이라이트 색상</h4>
+                </div>
+                <div class="flex space-x-2">
+                    <button onclick="window.hierarchyInstance.createHighlight('yellow')" class="w-8 h-8 bg-yellow-300 rounded hover:bg-yellow-400" title="노랑"></button>
+                    <button onclick="window.hierarchyInstance.createHighlight('blue')" class="w-8 h-8 bg-blue-300 rounded hover:bg-blue-400" title="파랑"></button>
+                    <button onclick="window.hierarchyInstance.createHighlight('green')" class="w-8 h-8 bg-green-300 rounded hover:bg-green-400" title="초록"></button>
+                    <button onclick="window.hierarchyInstance.createHighlight('red')" class="w-8 h-8 bg-red-300 rounded hover:bg-red-400" title="빨강"></button>
+                </div>
+            </div>
+        </main>
+    </div>
+
+    <!-- 로그인 모달 -->
+    <div x-data="authModal()" x-show="showLoginModal" class="fixed inset-0 bg-black bg-opacity-50 flex items-center justify-center z-50">
+        <div class="bg-white rounded-lg p-6 w-96 max-w-md mx-4">
+            <h2 class="text-xl font-bold mb-4">로그인</h2>
+            <form @submit.prevent="login()">
+                <div class="mb-4">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">이메일</label>
+                    <input 
+                        type="email" 
+                        x-model="loginForm.email" 
+                        required 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500"
+                    >
+                </div>
+                <div class="mb-6">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">비밀번호</label>
+                    <input 
+                        type="password" 
+                        x-model="loginForm.password" 
+                        required 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500"
+                    >
+                </div>
+                <div x-show="loginError" class="mb-4 p-3 bg-red-100 border border-red-400 text-red-700 rounded">
+                    <span x-text="loginError"></span>
+                </div>
+                <div class="flex justify-end space-x-3">
+                    <button 
+                        type="button" 
+                        @click="showLoginModal = false" 
+                        class="px-4 py-2 text-gray-600 border border-gray-300 rounded-md hover:bg-gray-50"
+                    >
+                        취소
+                    </button>
+                    <button 
+                        type="submit" 
+                        :disabled="loggingIn" 
+                        class="px-4 py-2 bg-blue-600 text-white rounded-md hover:bg-blue-700 disabled:opacity-50"
+                    >
+                        <span x-show="!loggingIn">로그인</span>
+                        <span x-show="loggingIn">로그인 중...</span>
+                    </button>
+                </div>
+            </form>
+        </div>
+    </div>
+
+    <!-- 업로드 모달 -->
+    <div x-data="uploadModal()" x-show="showUploadModal" class="fixed inset-0 bg-black bg-opacity-50 flex items-center justify-center z-50">
+        <div class="bg-white rounded-lg p-6 w-full max-w-2xl mx-4 max-h-[90vh] overflow-y-auto">
+            <h2 class="text-xl font-bold mb-4">문서 업로드</h2>
+            <form @submit.prevent="upload()">
+                <!-- 파일 선택 -->
+                <div class="mb-4">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">HTML 파일 *</label>
+                    <input 
+                        type="file" 
+                        accept=".html,.htm" 
+                        @change="handleFileSelect($event, 'html_file')"
+                        required 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500"
+                    >
+                </div>
+                
+                <div class="mb-4">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">PDF 파일 (선택사항)</label>
+                    <input 
+                        type="file" 
+                        accept=".pdf" 
+                        @change="handleFileSelect($event, 'pdf_file')"
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500"
+                    >
+                </div>
+
+                <!-- 서적 선택 -->
+                <div class="mb-4">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">서적 분류</label>
+                    <div class="space-y-2">
+                        <label class="flex items-center">
+                            <input type="radio" x-model="bookSelectionMode" value="existing" class="mr-2 text-blue-600" name="bookSelectionMode">
+                            기존 서적 선택
+                        </label>
+                        <label class="flex items-center">
+                            <input type="radio" x-model="bookSelectionMode" value="new" class="mr-2 text-blue-600" name="bookSelectionMode">
+                            새 서적 생성
+                        </label>
+                        <label class="flex items-center">
+                            <input type="radio" x-model="bookSelectionMode" value="none" class="mr-2 text-blue-600" name="bookSelectionMode">
+                            서적 없이 업로드
+                        </label>
+                    </div>
+                </div>
+
+                <!-- 기존 서적 선택 -->
+                <div x-show="bookSelectionMode === 'existing'" class="mb-4 space-y-3">
+                    <input 
+                        type="text" 
+                        x-model="bookSearchQuery" 
+                        @input="searchBooks" 
+                        placeholder="서적 제목으로 검색..." 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500"
+                    >
+                    <div x-show="searchedBooks.length > 0" class="max-h-40 overflow-y-auto border border-gray-200 rounded-md">
+                        <template x-for="book in searchedBooks" :key="book.id">
+                            <div 
+                                @click="selectBook(book)" 
+                                class="p-3 hover:bg-gray-50 cursor-pointer border-b last:border-b-0"
+                            >
+                                <div class="font-medium" x-text="book.title"></div>
+                                <div class="text-sm text-gray-600" x-text="book.author || '저자 미상'"></div>
+                            </div>
+                        </template>
+                    </div>
+                    <div x-show="selectedBook" class="p-3 bg-blue-50 border border-blue-200 rounded-md">
+                        <div class="font-medium text-blue-900" x-text="selectedBook?.title"></div>
+                        <div class="text-sm text-blue-700" x-text="selectedBook?.author || '저자 미상'"></div>
+                    </div>
+                </div>
+
+                <!-- 새 서적 생성 -->
+                <div x-show="bookSelectionMode === 'new'" class="mb-4 space-y-3">
+                    <input 
+                        type="text" 
+                        x-model="newBook.title" 
+                        @input="getSuggestions" 
+                        placeholder="서적 제목 *" 
+                        :required="bookSelectionMode === 'new'"
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500"
+                    >
+                    <input 
+                        type="text" 
+                        x-model="newBook.author" 
+                        placeholder="저자" 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500"
+                    >
+                    <div x-show="suggestions.length > 0" class="p-3 bg-yellow-50 border border-yellow-200 rounded-md">
+                        <p class="text-sm text-yellow-800 mb-2">비슷한 서적이 있습니다:</p>
+                        <template x-for="suggestion in suggestions" :key="suggestion.id">
+                            <div 
+                                @click="selectExistingFromSuggestion(suggestion)" 
+                                class="p-2 hover:bg-yellow-100 cursor-pointer rounded text-sm"
+                            >
+                                <span class="font-medium" x-text="suggestion.title"></span>
+                                <span class="text-yellow-700" x-text="suggestion.author ? ` - ${suggestion.author}` : ''"></span>
+                            </div>
+                        </template>
+                    </div>
+                </div>
+
+                <!-- 문서 정보 -->
+                <div class="mb-4">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">문서 제목 *</label>
+                    <input 
+                        type="text" 
+                        x-model="uploadForm.title" 
+                        required 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500" 
+                        placeholder="문서 제목"
+                    >
+                </div>
+
+                <div class="mb-4">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">문서 날짜</label>
+                    <input 
+                        type="date" 
+                        x-model="uploadForm.document_date" 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500"
+                    >
+                </div>
+
+                <div class="mb-4">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">설명</label>
+                    <textarea 
+                        x-model="uploadForm.description" 
+                        rows="3" 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500" 
+                        placeholder="문서에 대한 간단한 설명"
+                    ></textarea>
+                </div>
+
+                <div class="mb-4">
+                    <label class="block text-sm font-medium text-gray-700 mb-2">태그</label>
+                    <input 
+                        type="text" 
+                        x-model="uploadForm.tags" 
+                        class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500" 
+                        placeholder="태그를 쉼표로 구분하여 입력 (예: 중요, 회의록, 2024)"
+                    >
+                </div>
+
+                <div class="mb-6">
+                    <label class="flex items-center">
+                        <input type="checkbox" x-model="uploadForm.is_public" class="mr-2">
+                        <span class="text-sm text-gray-700">공개 문서로 설정</span>
+                    </label>
+                </div>
+
+                <div x-show="uploadError" class="mb-4 p-3 bg-red-100 border border-red-400 text-red-700 rounded">
+                    <span x-text="uploadError"></span>
+                </div>
+
+                <div class="flex justify-end space-x-3">
+                    <button 
+                        type="button" 
+                        @click="closeUploadModal()" 
+                        class="px-4 py-2 text-gray-600 border border-gray-300 rounded-md hover:bg-gray-50"
+                    >
+                        취소
+                    </button>
+                    <button 
+                        type="submit" 
+                        :disabled="uploading || !uploadForm.html_file || !uploadForm.title" 
+                        class="px-6 py-2 bg-blue-600 text-white rounded-md hover:bg-blue-700 disabled:opacity-50 disabled:cursor-not-allowed"
+                    >
+                        <span x-show="!uploading">업로드</span>
+                        <span x-show="uploading">
+                            <i class="fas fa-spinner fa-spin mr-2"></i>
+                            업로드 중...
+                        </span>
+                    </button>
+                </div>
+            </form>
+        </div>
+    </div>
+
+    <!-- JavaScript -->
+    <script src="static/js/api.js?v=2025012225"></script>
+    <script src="static/js/auth.js?v=2025012225"></script>
+    <script src="static/js/hierarchy.js?v=2025012225"></script>
+</body>
+</html>
diff --git a/frontend/index.html b/frontend/index.html
index 3141943..2144c22 100644
--- a/frontend/index.html
+++ b/frontend/index.html
@@ -12,9 +12,9 @@
 </head>
 <body class="bg-gray-50 min-h-screen">
     <!-- 메인 앱 -->
-    <div x-data="documentApp" x-init="init()">
+    <div x-data="documentApp()" x-init="init()">
         <!-- 로그인 모달 -->
-        <div x-data="authModal" x-show="showLoginModal" x-cloak class="fixed inset-0 bg-black bg-opacity-50 flex items-center justify-center z-50">
+        <div x-data="authModal()" x-show="showLoginModal" x-cloak class="fixed inset-0 bg-black bg-opacity-50 flex items-center justify-center z-50">
             <div class="bg-white rounded-lg p-8 max-w-md w-full mx-4">
                 <div class="flex justify-between items-center mb-6">
                     <h2 class="text-2xl font-bold text-gray-900">로그인</h2>
@@ -53,11 +53,15 @@
             <div class="max-w-7xl mx-auto px-4 sm:px-6 lg:px-8">
                 <div class="flex justify-between items-center h-16">
                     <!-- 로고 -->
-                    <div class="flex items-center">
+                    <div class="flex items-center space-x-4">
                         <h1 class="text-xl font-bold text-gray-900">
                             <i class="fas fa-file-alt mr-2"></i>
                             Document Server
                         </h1>
+                        <div class="flex space-x-2">
+                            <span class="px-3 py-1 text-sm bg-blue-100 text-blue-800 rounded-full">그리드 뷰</span>
+                            <a href="hierarchy.html" class="px-3 py-1 text-sm bg-gray-100 text-gray-600 rounded-full hover:bg-gray-200">계층구조 뷰</a>
+                        </div>
                     </div>
 
                     <!-- 검색바 -->
@@ -181,7 +185,16 @@
                                         <i class="fas fa-file-alt text-blue-500 text-xl"></i>
                                     </div>
                                     
-                                    <p class="text-gray-600 text-sm mb-4 line-clamp-3" x-text="doc.description || '설명 없음'"></p>
+                                    <p class="text-gray-600 text-sm mb-3 line-clamp-3" x-text="doc.description || '설명 없음'"></p>
+                                    
+                                    <!-- 서적 정보 -->
+                                    <div x-show="doc.book_title" class="mb-3 p-2 bg-green-50 border border-green-200 rounded-md">
+                                        <div class="flex items-center text-sm">
+                                            <i class="fas fa-book text-green-600 mr-2"></i>
+                                            <span class="font-medium text-green-800" x-text="doc.book_title"></span>
+                                            <span x-show="doc.book_author" class="text-green-600 ml-1" x-text="' by ' + doc.book_author"></span>
+                                        </div>
+                                    </div>
                                     
                                     <div class="flex flex-wrap gap-1 mb-4">
                                         <template x-for="tag in doc.tags" :key="tag">
@@ -191,7 +204,24 @@
                                     
                                     <div class="flex justify-between items-center text-sm text-gray-500">
                                         <span x-text="formatDate(doc.created_at)"></span>
-                                        <span x-text="doc.uploader_name"></span>
+                                        <div class="flex items-center space-x-2">
+                                            <span x-text="doc.uploader_name"></span>
+                                            <!-- 액션 버튼들 -->
+                                            <div class="flex space-x-1 ml-2">
+                                                <button @click.stop="editDocument(doc)" 
+                                                        class="p-1 text-gray-400 hover:text-blue-600 transition-colors"
+                                                        title="문서 수정">
+                                                    <i class="fas fa-edit text-sm"></i>
+                                                </button>
+                                                <!-- 관리자만 삭제 버튼 표시 -->
+                                                <button x-show="currentUser && currentUser.is_admin" 
+                                                        @click.stop="deleteDocument(doc.id)" 
+                                                        class="p-1 text-gray-400 hover:text-red-600 transition-colors"
+                                                        title="문서 삭제 (관리자 전용)">
+                                                    <i class="fas fa-trash text-sm"></i>
+                                                </button>
+                                            </div>
+                                        </div>
                                     </div>
                                 </div>
                             </div>
@@ -225,7 +255,7 @@
                     </button>
                 </div>
 
-                <div x-data="uploadModal">
+                <div x-data="uploadModal()">
                     <form @submit.prevent="upload">
                         <!-- 파일 업로드 영역 -->
                         <div class="mb-6">
@@ -272,6 +302,98 @@
                             </div>
                         </div>
 
+                        <!-- 서적 선택/생성 -->
+                        <div class="mb-6 p-4 bg-gray-50 rounded-lg">
+                            <label class="block text-sm font-medium text-gray-700 mb-3">📚 서적 설정</label>
+                            
+                            <!-- 서적 선택 방식 -->
+                            <div class="flex space-x-4 mb-4">
+                                <label class="flex items-center">
+                                    <input type="radio" x-model="bookSelectionMode" value="existing" 
+                                           class="mr-2 text-blue-600">
+                                    <span class="text-sm">기존 서적에 추가</span>
+                                </label>
+                                <label class="flex items-center">
+                                    <input type="radio" x-model="bookSelectionMode" value="new" 
+                                           class="mr-2 text-blue-600">
+                                    <span class="text-sm">새 서적 생성</span>
+                                </label>
+                                <label class="flex items-center">
+                                    <input type="radio" x-model="bookSelectionMode" value="none" 
+                                           class="mr-2 text-blue-600">
+                                    <span class="text-sm">서적 없이 업로드</span>
+                                </label>
+                            </div>
+
+                            <!-- 기존 서적 선택 -->
+                            <div x-show="bookSelectionMode === 'existing'" class="space-y-3">
+                                <div>
+                                    <input type="text" x-model="bookSearchQuery" @input="searchBooks" 
+                                           placeholder="서적 제목으로 검색..."
+                                           class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500">
+                                </div>
+                                
+                                <!-- 검색 결과 -->
+                                <div x-show="searchedBooks.length > 0" class="max-h-40 overflow-y-auto border border-gray-200 rounded-md">
+                                    <template x-for="book in searchedBooks" :key="book.id">
+                                        <div @click="selectBook(book)" 
+                                             :class="selectedBook?.id === book.id ? 'bg-blue-100 border-blue-500' : 'hover:bg-gray-50'"
+                                             class="p-3 border-b border-gray-200 cursor-pointer">
+                                            <div class="font-medium text-sm" x-text="book.title"></div>
+                                            <div class="text-xs text-gray-500">
+                                                <span x-text="book.author || '저자 미상'"></span> · 
+                                                <span x-text="book.document_count + '개 문서'"></span>
+                                            </div>
+                                        </div>
+                                    </template>
+                                </div>
+
+                                <!-- 선택된 서적 표시 -->
+                                <div x-show="selectedBook" class="p-3 bg-blue-50 border border-blue-200 rounded-md">
+                                    <div class="flex items-center justify-between">
+                                        <div>
+                                            <div class="font-medium text-blue-900" x-text="selectedBook?.title"></div>
+                                            <div class="text-sm text-blue-700" x-text="selectedBook?.author || '저자 미상'"></div>
+                                        </div>
+                                        <button @click="selectedBook = null" class="text-blue-500 hover:text-blue-700">
+                                            <i class="fas fa-times"></i>
+                                        </button>
+                                    </div>
+                                </div>
+                            </div>
+
+                            <!-- 새 서적 생성 -->
+                            <div x-show="bookSelectionMode === 'new'" class="space-y-3">
+                                <div class="grid grid-cols-1 md:grid-cols-2 gap-3">
+                                    <div>
+                                        <input type="text" x-model="newBook.title" @input="getSuggestions"
+                                               placeholder="서적 제목 *" :required="bookSelectionMode === 'new'"
+                                               class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500">
+                                    </div>
+                                    <div>
+                                        <input type="text" x-model="newBook.author" 
+                                               placeholder="저자"
+                                               class="w-full px-3 py-2 border border-gray-300 rounded-md focus:outline-none focus:ring-2 focus:ring-blue-500">
+                                    </div>
+                                </div>
+                                
+                                <!-- 유사 서적 추천 -->
+                                <div x-show="suggestions.length > 0" class="p-3 bg-yellow-50 border border-yellow-200 rounded-md">
+                                    <div class="text-sm font-medium text-yellow-800 mb-2">💡 유사한 서적이 있습니다:</div>
+                                    <template x-for="suggestion in suggestions" :key="suggestion.id">
+                                        <div @click="selectExistingFromSuggestion(suggestion)" 
+                                             class="p-2 bg-white border border-yellow-300 rounded cursor-pointer hover:bg-yellow-50 mb-1">
+                                            <div class="text-sm font-medium" x-text="suggestion.title"></div>
+                                            <div class="text-xs text-gray-600">
+                                                <span x-text="suggestion.author || '저자 미상'"></span> · 
+                                                <span x-text="Math.round(suggestion.similarity_score * 100) + '% 유사'"></span>
+                                            </div>
+                                        </div>
+                                    </template>
+                                </div>
+                            </div>
+                        </div>
+
                         <!-- 문서 정보 -->
                         <div class="grid grid-cols-1 md:grid-cols-2 gap-4 mb-4">
                             <div>
@@ -356,5 +478,10 @@
             overflow: hidden;
         }
     </style>
+
+    <!-- JavaScript 파일들 -->
+    <script src="/static/js/api.js?v=2025012222"></script>
+    <script src="/static/js/auth.js?v=2025012222"></script>
+    <script src="/static/js/main.js?v=2025012222"></script>
 </body>
 </html>
diff --git a/frontend/static/js/api.js b/frontend/static/js/api.js
index 9a1efa3..065ff93 100644
--- a/frontend/static/js/api.js
+++ b/frontend/static/js/api.js
@@ -1,9 +1,9 @@
 /**
  * API 통신 유틸리티
  */
-class API {
+class DocumentServerAPI {
     constructor() {
-        this.baseURL = 'http://localhost:24102/api';
+        this.baseURL = '/api';  // Nginx 프록시를 통해 접근
         this.token = localStorage.getItem('access_token');
     }
 
@@ -143,10 +143,18 @@ class API {
         return await this.get('/documents/', params);
     }
 
+    async getDocumentsHierarchy() {
+        return await this.get('/documents/hierarchy/structured');
+    }
+
     async getDocument(documentId) {
         return await this.get(`/documents/${documentId}`);
     }
 
+    async getDocumentContent(documentId) {
+        return await this.get(`/documents/${documentId}/content`);
+    }
+
     async uploadDocument(formData) {
         return await this.uploadFile('/documents/', formData);
     }
@@ -326,7 +334,87 @@ class API {
         if (documentId) params.append('document_id', documentId);
         return await this.get(`/search/notes?${params}`);
     }
+
+    // === 서적 관련 API ===
+    async getBooks(skip = 0, limit = 50, search = null) {
+        const params = new URLSearchParams({ skip, limit });
+        if (search) params.append('search', search);
+        return await this.get(`/books?${params}`);
+    }
+
+    async createBook(bookData) {
+        return await this.post('/books', bookData);
+    }
+
+    async getBook(bookId) {
+        return await this.get(`/books/${bookId}`);
+    }
+
+    async searchBooks(query, limit = 10) {
+        const params = new URLSearchParams({ q: query, limit });
+        return await this.get(`/books/search/?${params}`);
+    }
+
+    async getBookSuggestions(title, limit = 5) {
+        const params = new URLSearchParams({ title, limit });
+        return await this.get(`/books/suggestions/?${params}`);
+    }
+
+    // === 서적 소분류 관련 API ===
+    async createBookCategory(categoryData) {
+        return await this.post('/book-categories/', categoryData);
+    }
+
+    async getBookCategories(bookId) {
+        return await this.get(`/book-categories/book/${bookId}`);
+    }
+
+    async updateBookCategory(categoryId, categoryData) {
+        return await this.put(`/book-categories/${categoryId}`, categoryData);
+    }
+
+    async deleteBookCategory(categoryId) {
+        return await this.delete(`/book-categories/${categoryId}`);
+    }
+
+    async updateDocumentOrder(orderData) {
+        return await this.put('/book-categories/documents/reorder', orderData);
+    }
+
+    // === 하이라이트 관련 API ===
+    async getDocumentHighlights(documentId) {
+        return await this.get(`/highlights/document/${documentId}`);
+    }
+
+    async createHighlight(highlightData) {
+        return await this.post('/highlights/', highlightData);
+    }
+
+    async updateHighlight(highlightId, highlightData) {
+        return await this.put(`/highlights/${highlightId}`, highlightData);
+    }
+
+    async deleteHighlight(highlightId) {
+        return await this.delete(`/highlights/${highlightId}`);
+    }
+
+    // === 메모 관련 API ===
+    async getDocumentNotes(documentId) {
+        return await this.get(`/notes/document/${documentId}`);
+    }
+
+    async createNote(noteData) {
+        return await this.post('/notes/', noteData);
+    }
+
+    async updateNote(noteId, noteData) {
+        return await this.put(`/notes/${noteId}`, noteData);
+    }
+
+    async deleteNote(noteId) {
+        return await this.delete(`/notes/${noteId}`);
+    }
 }
 
 // 전역 API 인스턴스
-window.api = new API();
+window.api = new DocumentServerAPI();
diff --git a/frontend/static/js/auth.js b/frontend/static/js/auth.js
index ed2df17..9c9ec22 100644
--- a/frontend/static/js/auth.js
+++ b/frontend/static/js/auth.js
@@ -18,14 +18,14 @@ window.authModal = () => ({
 
         try {
             // 실제 API 호출
-            const response = await api.login(this.loginForm.email, this.loginForm.password);
+            const response = await window.api.login(this.loginForm.email, this.loginForm.password);
             
             // 토큰 저장
-            api.setToken(response.access_token);
+            window.api.setToken(response.access_token);
             localStorage.setItem('refresh_token', response.refresh_token);
             
             // 사용자 정보 가져오기
-            const userResponse = await api.getCurrentUser();
+            const userResponse = await window.api.getCurrentUser();
             
             // 전역 상태 업데이트
             window.dispatchEvent(new CustomEvent('auth-changed', { 
@@ -45,7 +45,7 @@ window.authModal = () => ({
 
     async logout() {
         try {
-            await api.logout();
+            await window.api.logout();
         } catch (error) {
             console.error('Logout error:', error);
         } finally {
@@ -79,7 +79,7 @@ async function refreshTokenIfNeeded() {
     } catch (error) {
         console.error('Token refresh failed:', error);
         // 갱신 실패시 로그아웃
-        api.setToken(null);
+        window.api.setToken(null);
         localStorage.removeItem('refresh_token');
         window.dispatchEvent(new CustomEvent('auth-changed', { 
             detail: { isAuthenticated: false, user: null } 
diff --git a/frontend/static/js/hierarchy.js b/frontend/static/js/hierarchy.js
new file mode 100644
index 0000000..f3d42b2
--- /dev/null
+++ b/frontend/static/js/hierarchy.js
@@ -0,0 +1,1115 @@
+// 계층구조 뷰 전용 JavaScript
+
+// 메인 계층구조 앱
+window.hierarchyApp = function() {
+    return {
+        // 상태 관리
+        currentUser: null,
+        hierarchy: { books: {}, uncategorized: [] },
+        loading: false,
+        searchQuery: '',
+        
+        // UI 상태
+        expandedBooks: [],
+        expandedCategories: [],
+        expandedUncategorizedInBooks: [],
+        showUncategorized: false,
+        showUploadModal: false,
+        showLoginModal: false,
+        
+        // 선택된 문서
+        selectedDocument: null,
+        documentContent: null,
+        loadingDocument: false,
+        
+        // 하이라이트 & 메모
+        highlights: [],
+        notes: [],
+        selectedText: '',
+        showHighlightMenu: false,
+        highlightMenuPosition: { x: 0, y: 0 },
+        highlightMode: false, // 하이라이트 모드 토글
+        
+        // 드래그 앤 드롭
+        draggedDocument: null,
+        
+        // 초기화
+        async init() {
+            console.log('🚀 계층구조 앱 초기화 중...');
+            // 전역 인스턴스 등록
+            window.hierarchyInstance = this;
+            await this.checkAuthStatus();
+            if (this.currentUser) {
+                await this.loadHierarchy();
+            }
+            this.setupEventListeners();
+        },
+        
+        // 이벤트 리스너 설정
+        setupEventListeners() {
+            // 인증 상태 변경 이벤트
+            window.addEventListener('auth-changed', (event) => {
+                this.currentUser = event.detail.user;
+                if (this.currentUser) {
+                    this.loadHierarchy();
+                }
+            });
+            
+            // 업로드 완료 이벤트
+            window.addEventListener('upload-complete', () => {
+                this.loadHierarchy();
+            });
+        },
+        
+        // 인증 상태 확인
+        async checkAuthStatus() {
+            try {
+                const user = await window.api.getCurrentUser();
+                this.currentUser = user;
+                console.log('✅ 사용자 인증됨:', user.email);
+            } catch (error) {
+                console.log('❌ 인증되지 않음');
+                this.currentUser = null;
+            }
+        },
+        
+        // 계층구조 데이터 로드
+        async loadHierarchy() {
+            if (!this.currentUser) return;
+            
+            this.loading = true;
+            try {
+                console.log('📊 계층구조 데이터 로딩...');
+                const data = await window.api.getDocumentsHierarchy();
+                this.hierarchy = data;
+                console.log('✅ 계층구조 로드 완료:', data);
+                
+                // 첫 번째 서적과 미분류를 기본으로 펼치기
+                if (Object.keys(data.books).length > 0) {
+                    const firstBookId = Object.keys(data.books)[0];
+                    this.expandedBooks = [firstBookId];
+                }
+                if (data.uncategorized.length > 0) {
+                    this.showUncategorized = true;
+                }
+            } catch (error) {
+                console.error('❌ 계층구조 로드 실패:', error);
+            } finally {
+                this.loading = false;
+            }
+        },
+        
+        // 계층구조 새로고침
+        async refreshHierarchy() {
+            await this.loadHierarchy();
+        },
+        
+        // 서적 토글
+        toggleBook(bookId) {
+            const index = this.expandedBooks.indexOf(bookId);
+            if (index > -1) {
+                this.expandedBooks.splice(index, 1);
+            } else {
+                this.expandedBooks.push(bookId);
+            }
+        },
+        
+        // 소분류 토글
+        toggleCategory(categoryId) {
+            const index = this.expandedCategories.indexOf(categoryId);
+            if (index > -1) {
+                this.expandedCategories.splice(index, 1);
+            } else {
+                this.expandedCategories.push(categoryId);
+            }
+        },
+        
+        // 서적 내 미분류 토글
+        toggleUncategorizedInBook(bookId) {
+            const index = this.expandedUncategorizedInBooks.indexOf(bookId);
+            if (index > -1) {
+                this.expandedUncategorizedInBooks.splice(index, 1);
+            } else {
+                this.expandedUncategorizedInBooks.push(bookId);
+            }
+        },
+        
+        // 전체 미분류 토글
+        toggleUncategorized() {
+            this.showUncategorized = !this.showUncategorized;
+        },
+        
+        // 문서 열기
+        async openDocument(documentId) {
+            console.log('📄 문서 열기:', documentId);
+            this.loadingDocument = true;
+            this.documentContent = null;
+            this.highlights = [];
+            this.notes = [];
+            
+            try {
+                // 문서 정보 가져오기
+                const docInfo = await window.api.getDocument(documentId);
+                this.selectedDocument = docInfo;
+                
+                // HTML 콘텐츠 가져오기 (인증된 API 사용)
+                const content = await window.api.getDocumentContent(documentId);
+                this.documentContent = content;
+                
+                // 하이라이트 및 메모 로드
+                await this.loadHighlightsAndNotes(documentId);
+                
+                // 문서 로드 후 하이라이트 적용 (DOM이 준비될 때까지 대기)
+                setTimeout(async () => {
+                    console.log(`🎨 하이라이트 적용 시도: ${this.highlights.length}개`);
+                    this.applyHighlights();
+                    this.setupTextSelection();
+                }, 200);
+                
+                console.log('✅ 문서 로드 완료');
+            } catch (error) {
+                console.error('❌ 문서 로드 실패:', error);
+                alert('문서를 불러오는 중 오류가 발생했습니다.');
+            } finally {
+                this.loadingDocument = false;
+            }
+        },
+        
+        // 하이라이트 및 메모 로드
+        async loadHighlightsAndNotes(documentId) {
+            try {
+                console.log(`📊 하이라이트/메모 로드 시작: ${documentId}`);
+                
+                // 하이라이트 로드
+                console.log('🔍 하이라이트 API 호출 중...');
+                const highlights = await window.api.getDocumentHighlights(documentId);
+                console.log('📥 하이라이트 API 응답:', highlights);
+                
+                // 메모 로드
+                console.log('🔍 메모 API 호출 중...');
+                const notes = await window.api.getDocumentNotes(documentId);
+                console.log('📥 메모 API 응답:', notes);
+                
+                this.highlights = highlights || [];
+                this.notes = notes || [];
+                
+                console.log(`📝 최종 저장: 하이라이트 ${this.highlights.length}개, 메모 ${this.notes.length}개`);
+                
+                if (this.highlights.length > 0) {
+                    console.log('📝 하이라이트 상세:', this.highlights.map(h => ({
+                        id: h.id,
+                        text: h.selected_text,
+                        color: h.color || h.highlight_color
+                    })));
+                }
+                
+            } catch (error) {
+                console.error('❌ 하이라이트/메모 로드 실패:', error);
+                console.error('❌ 오류 상세:', error.message, error.stack);
+                this.highlights = [];
+                this.notes = [];
+            }
+        },
+        
+        // 하이라이트 적용 (viewer.js와 동일한 로직)
+        applyHighlights() {
+            if (!this.selectedDocument || !this.highlights.length) {
+                console.log('📝 하이라이트 적용 건너뜀: 문서 없음 또는 하이라이트 없음');
+                return;
+            }
+            
+            const contentElement = document.querySelector('.prose');
+            if (!contentElement) {
+                console.log('📝 하이라이트 적용 건너뜀: .prose 요소 없음');
+                return;
+            }
+            
+            console.log(`📝 하이라이트 적용 시작: ${this.highlights.length}개`);
+            
+            // 기존 하이라이트 제거
+            contentElement.querySelectorAll('.highlight').forEach(el => {
+                const parent = el.parentNode;
+                parent.replaceChild(document.createTextNode(el.textContent), el);
+                parent.normalize();
+            });
+            
+            // 새 하이라이트 적용
+            this.highlights.forEach(highlight => {
+                this.applyHighlight(highlight);
+            });
+        },
+        
+        // 개별 하이라이트 적용 (viewer.js와 동일한 로직)
+        applyHighlight(highlight) {
+            const content = document.querySelector('.prose');
+            if (!content) return;
+            
+            const walker = document.createTreeWalker(
+                content,
+                NodeFilter.SHOW_TEXT,
+                null,
+                false
+            );
+            
+            let currentOffset = 0;
+            let node;
+            
+            while (node = walker.nextNode()) {
+                const nodeLength = node.textContent.length;
+                
+                if (currentOffset + nodeLength > highlight.start_offset) {
+                    const startInNode = Math.max(0, highlight.start_offset - currentOffset);
+                    const endInNode = Math.min(nodeLength, highlight.end_offset - currentOffset);
+                    
+                    if (startInNode < endInNode) {
+                        try {
+                            const range = document.createRange();
+                            range.setStart(node, startInNode);
+                            range.setEnd(node, endInNode);
+                            
+                            const span = document.createElement('span');
+                            span.className = `highlight cursor-pointer`;
+                            span.style.backgroundColor = highlight.color || '#FFFF00';
+                            span.dataset.highlightId = highlight.id;
+                            span.title = highlight.note || '하이라이트';
+                            
+                            // 하이라이트 클릭 이벤트
+                            span.addEventListener('click', (e) => {
+                                e.stopPropagation();
+                                this.showHighlightDetails(highlight, e.target);
+                            });
+                            
+                            range.surroundContents(span);
+                            console.log(`✅ 하이라이트 적용됨: ${highlight.selected_text}`);
+                            break;
+                        } catch (error) {
+                            console.warn('하이라이트 적용 실패:', error);
+                        }
+                    }
+                }
+                
+                currentOffset += nodeLength;
+                
+                if (currentOffset >= highlight.end_offset) {
+                    break;
+                }
+            }
+        },
+        
+        // 텍스트 선택 설정
+        setupTextSelection() {
+            console.log('🎯 텍스트 선택 이벤트 설정 중...');
+            const contentElement = document.querySelector('.prose');
+            if (!contentElement) {
+                console.warn('❌ .prose 요소를 찾을 수 없습니다');
+                return;
+            }
+            
+            contentElement.addEventListener('mouseup', (e) => {
+                console.log('🖱️ 마우스업 이벤트 발생');
+                const selection = window.getSelection();
+                if (selection.rangeCount > 0 && !selection.isCollapsed) {
+                    const range = selection.getRangeAt(0);
+                    const text = selection.toString().trim();
+                    
+                    console.log('📝 선택된 텍스트:', text);
+                    
+                    if (text.length > 0 && this.highlightMode) {
+                        this.selectedText = text;
+                        // 직접 DOM 조작으로 메뉴 표시
+                        const menu = document.getElementById('highlight-menu');
+                        if (menu) {
+                            menu.style.display = 'block';
+                            console.log('✅ 하이라이트 메뉴 표시됨');
+                        } else {
+                            console.error('❌ 하이라이트 메뉴 DOM 요소를 찾을 수 없음');
+                        }
+                    }
+                }
+            });
+            
+            // 다른 곳 클릭 시 메뉴 숨기기 (메뉴 자체 클릭은 제외)
+            document.addEventListener('click', (e) => {
+                if (!e.target.closest('#highlight-menu') && !e.target.closest('.prose')) {
+                    const menu = document.getElementById('highlight-menu');
+                    if (menu) {
+                        menu.style.display = 'none';
+                    }
+                }
+            });
+        },
+        
+        // 하이라이트 생성 (viewer.js와 동일한 로직)
+        async createHighlight(color = 'yellow') {
+            if (!this.selectedText || !this.selectedDocument) return;
+            
+            const selection = window.getSelection();
+            if (selection.rangeCount === 0) return;
+            
+            try {
+                const range = selection.getRangeAt(0);
+                const content = document.querySelector('.prose');
+                
+                // 텍스트 오프셋 계산
+                const offsets = this.calculateTextOffsets(range, content);
+                
+                // 색상 매핑
+                const colorMap = {
+                    'yellow': '#FFFF00',
+                    'blue': '#87CEEB', 
+                    'green': '#90EE90',
+                    'red': '#FFB6C1'
+                };
+                
+                const highlightData = {
+                    document_id: this.selectedDocument.id,
+                    start_offset: offsets.start,
+                    end_offset: offsets.end,
+                    selected_text: this.selectedText,
+                    color: colorMap[color] || '#FFFF00',
+                    note: null
+                };
+                
+                console.log('📝 하이라이트 생성 데이터:', highlightData);
+                
+                const newHighlight = await window.api.createHighlight(highlightData);
+                this.highlights.push(newHighlight);
+                
+                // 하이라이트 다시 렌더링
+                this.applyHighlights();
+                
+                // 선택 해제
+                selection.removeAllRanges();
+                const menu = document.getElementById('highlight-menu');
+                if (menu) {
+                    menu.style.display = 'none';
+                }
+                this.selectedText = '';
+                
+                console.log('✅ 하이라이트 생성 완료');
+                
+                // 성공 메시지
+                alert(`하이라이트가 생성되었습니다: "${this.selectedText}"`);
+                
+                // 메모 추가는 하이라이트 클릭으로만 가능하도록 변경
+                
+            } catch (error) {
+                console.error('❌ 하이라이트 생성 실패:', error);
+                alert('하이라이트 생성 중 오류가 발생했습니다.');
+            }
+        },
+        
+        // 텍스트 오프셋 계산 (viewer.js와 동일한 로직)
+        calculateTextOffsets(range, container) {
+            const walker = document.createTreeWalker(
+                container,
+                NodeFilter.SHOW_TEXT,
+                null,
+                false
+            );
+            
+            let currentOffset = 0;
+            let startOffset = -1;
+            let endOffset = -1;
+            let node;
+            
+            while (node = walker.nextNode()) {
+                const nodeLength = node.textContent.length;
+                
+                if (startOffset === -1 && node === range.startContainer) {
+                    startOffset = currentOffset + range.startOffset;
+                }
+                
+                if (endOffset === -1 && node === range.endContainer) {
+                    endOffset = currentOffset + range.endOffset;
+                    break;
+                }
+                
+                currentOffset += nodeLength;
+            }
+            
+            return {
+                start: startOffset,
+                end: endOffset
+            };
+        },
+        
+        // 텍스트 오프셋 계산 (간단한 버전)
+        getTextOffset(container, offset) {
+            const contentElement = document.querySelector('.prose');
+            if (!contentElement) return 0;
+            
+            const walker = document.createTreeWalker(
+                contentElement,
+                NodeFilter.SHOW_TEXT,
+                null,
+                false
+            );
+            
+            let textOffset = 0;
+            let node;
+            
+            while (node = walker.nextNode()) {
+                if (node === container) {
+                    return textOffset + offset;
+                }
+                textOffset += node.textContent.length;
+            }
+            
+            return textOffset;
+        },
+        
+        // 하이라이트에서 Range 생성 (간단한 버전)
+        createRangeFromHighlight(highlight) {
+            const contentElement = document.querySelector('.prose');
+            if (!contentElement) return null;
+            
+            const walker = document.createTreeWalker(
+                contentElement,
+                NodeFilter.SHOW_TEXT,
+                null,
+                false
+            );
+            
+            let currentOffset = 0;
+            let startNode = null, startOffset = 0;
+            let endNode = null, endOffset = 0;
+            let node;
+            
+            while (node = walker.nextNode()) {
+                const nodeLength = node.textContent.length;
+                
+                if (!startNode && currentOffset + nodeLength > highlight.start_offset) {
+                    startNode = node;
+                    startOffset = highlight.start_offset - currentOffset;
+                }
+                
+                if (!endNode && currentOffset + nodeLength >= highlight.end_offset) {
+                    endNode = node;
+                    endOffset = highlight.end_offset - currentOffset;
+                    break;
+                }
+                
+                currentOffset += nodeLength;
+            }
+            
+            if (startNode && endNode) {
+                const range = document.createRange();
+                range.setStart(startNode, startOffset);
+                range.setEnd(endNode, endOffset);
+                return range;
+            }
+            
+            return null;
+        },
+        
+        // 하이라이트 상세 정보 표시 (viewer.js와 동일한 툴팁 방식)
+        showHighlightDetails(highlight, element) {
+            // 기존 툴팁 제거
+            this.hideTooltip();
+            
+            const tooltip = document.createElement('div');
+            tooltip.id = 'highlight-tooltip';
+            tooltip.className = 'absolute bg-white border border-gray-300 rounded-lg shadow-lg p-4 z-50 max-w-sm';
+            tooltip.style.minWidth = '300px';
+            
+            // 하이라이트 정보와 메모 표시
+            const highlightNotes = this.notes.filter(note => note.highlight_id === highlight.id);
+            
+            tooltip.innerHTML = `
+                <div class="mb-3">
+                    <div class="text-sm text-gray-600 mb-1">선택된 텍스트</div>
+                    <div class="font-medium text-gray-900 bg-yellow-100 px-2 py-1 rounded">
+                        "${highlight.selected_text}"
+                    </div>
+                </div>
+                
+                <div class="mb-3">
+                    <div class="flex items-center justify-between mb-2">
+                        <span class="text-sm font-medium text-gray-700">메모 (${highlightNotes.length})</span>
+                        <button onclick="window.hierarchyInstance.showAddNoteForm('${highlight.id}')" 
+                                class="text-xs bg-blue-500 text-white px-2 py-1 rounded hover:bg-blue-600">
+                            + 메모 추가
+                        </button>
+                    </div>
+                    
+                    <div id="notes-list" class="space-y-2 max-h-40 overflow-y-auto">
+                        ${highlightNotes.length > 0 ? 
+                            highlightNotes.map(note => `
+                                <div class="bg-gray-50 p-2 rounded text-sm">
+                                    <div class="text-gray-800">${note.content}</div>
+                                    <div class="flex justify-between items-center mt-1">
+                                        <span class="text-xs text-gray-500">${new Date(note.created_at).toLocaleDateString()}</span>
+                                        <div class="space-x-1">
+                                            <button onclick="window.hierarchyInstance.editNote('${note.id}', '${note.content.replace(/'/g, "\\'")}')" 
+                                                    class="text-xs text-blue-600 hover:text-blue-800">수정</button>
+                                            <button onclick="window.hierarchyInstance.deleteNote('${note.id}')" 
+                                                    class="text-xs text-red-600 hover:text-red-800">삭제</button>
+                                        </div>
+                                    </div>
+                                </div>
+                            `).join('') 
+                            : '<div class="text-gray-500 text-sm text-center py-2">메모가 없습니다</div>'
+                        }
+                    </div>
+                </div>
+                
+                <div class="flex justify-between pt-2 border-t">
+                    <button onclick="window.hierarchyInstance.deleteHighlight('${highlight.id}')" 
+                            class="text-xs bg-red-500 text-white px-3 py-1 rounded hover:bg-red-600">
+                        하이라이트 삭제
+                    </button>
+                    <button onclick="window.hierarchyInstance.hideTooltip()" 
+                            class="text-xs bg-gray-500 text-white px-3 py-1 rounded hover:bg-gray-600">
+                        닫기
+                    </button>
+                </div>
+            `;
+            
+            document.body.appendChild(tooltip);
+            
+            // 위치 계산
+            const rect = element.getBoundingClientRect();
+            const tooltipRect = tooltip.getBoundingClientRect();
+            
+            let top = rect.bottom + window.scrollY + 10;
+            let left = rect.left + window.scrollX;
+            
+            // 화면 경계 체크
+            if (left + tooltipRect.width > window.innerWidth) {
+                left = window.innerWidth - tooltipRect.width - 10;
+            }
+            if (top + tooltipRect.height > window.innerHeight + window.scrollY) {
+                top = rect.top + window.scrollY - tooltipRect.height - 10;
+            }
+            
+            tooltip.style.top = top + 'px';
+            tooltip.style.left = left + 'px';
+            
+            // 외부 클릭 시 닫기
+            setTimeout(() => {
+                document.addEventListener('click', this.handleTooltipOutsideClick.bind(this));
+            }, 100);
+        },
+        
+        // 툴팁 숨기기
+        hideTooltip() {
+            const tooltip = document.getElementById('highlight-tooltip');
+            if (tooltip) {
+                tooltip.remove();
+            }
+            document.removeEventListener('click', this.handleTooltipOutsideClick.bind(this));
+        },
+        
+        // 툴팁 외부 클릭 처리
+        handleTooltipOutsideClick(e) {
+            if (!e.target.closest('#highlight-tooltip')) {
+                this.hideTooltip();
+            }
+        },
+        
+        // 메모 추가 폼 표시
+        showAddNoteForm(highlightId) {
+            const tooltip = document.getElementById('highlight-tooltip');
+            if (!tooltip) return;
+            
+            const notesList = tooltip.querySelector('#notes-list');
+            notesList.innerHTML = `
+                <div class="bg-blue-50 p-3 rounded">
+                    <div class="mb-2">
+                        <label class="block text-sm font-medium text-gray-700 mb-1">새 메모</label>
+                        <textarea id="new-note-content" 
+                                  class="w-full px-2 py-1 border border-gray-300 rounded text-sm" 
+                                  rows="3" 
+                                  placeholder="메모를 입력하세요..."></textarea>
+                    </div>
+                    <div class="flex justify-end space-x-2">
+                        <button onclick="window.hierarchyInstance.cancelAddNote('${highlightId}')" 
+                                class="text-xs bg-gray-500 text-white px-2 py-1 rounded hover:bg-gray-600">
+                            취소
+                        </button>
+                        <button onclick="window.hierarchyInstance.saveNewNote('${highlightId}')" 
+                                class="text-xs bg-blue-500 text-white px-2 py-1 rounded hover:bg-blue-600">
+                            저장
+                        </button>
+                    </div>
+                </div>
+            `;
+        },
+        
+        // 새 메모 저장
+        async saveNewNote(highlightId) {
+            const content = document.getElementById('new-note-content').value.trim();
+            if (!content) {
+                alert('메모 내용을 입력해주세요');
+                return;
+            }
+            
+            try {
+                const noteData = {
+                    highlight_id: highlightId,
+                    content: content,
+                    is_private: false,
+                    tags: []
+                };
+                
+                const newNote = await window.api.createNote(noteData);
+                
+                // 로컬 데이터 업데이트
+                this.notes.push(newNote);
+                
+                // 툴팁 새로고침
+                const highlight = this.highlights.find(h => h.id === highlightId);
+                if (highlight) {
+                    const element = document.querySelector(`[data-highlight-id="${highlightId}"]`);
+                    if (element) {
+                        this.showHighlightDetails(highlight, element);
+                    }
+                }
+                
+            } catch (error) {
+                console.error('Failed to save note:', error);
+                alert('메모 저장에 실패했습니다');
+            }
+        },
+        
+        // 메모 추가 취소
+        cancelAddNote(highlightId) {
+            const highlight = this.highlights.find(h => h.id === highlightId);
+            if (highlight) {
+                const element = document.querySelector(`[data-highlight-id="${highlightId}"]`);
+                if (element) {
+                    this.showHighlightDetails(highlight, element);
+                }
+            }
+        },
+        
+        // 메모 수정
+        editNote(noteId, currentContent) {
+            const newContent = prompt('메모를 수정하세요:', currentContent);
+            if (newContent !== null && newContent.trim() !== currentContent) {
+                this.updateNote(noteId, newContent.trim());
+            }
+        },
+        
+        // 메모 업데이트
+        async updateNote(noteId, content) {
+            try {
+                await window.api.updateNote(noteId, { content });
+                
+                // 로컬 데이터 업데이트
+                const note = this.notes.find(n => n.id === noteId);
+                if (note) {
+                    note.content = content;
+                }
+                
+                // 툴팁 새로고침
+                const highlight = this.highlights.find(h => 
+                    this.notes.some(n => n.id === noteId && n.highlight_id === h.id)
+                );
+                if (highlight) {
+                    const element = document.querySelector(`[data-highlight-id="${highlight.id}"]`);
+                    if (element) {
+                        this.showHighlightDetails(highlight, element);
+                    }
+                }
+                
+            } catch (error) {
+                console.error('Failed to update note:', error);
+                alert('메모 수정에 실패했습니다');
+            }
+        },
+        
+        // 메모 삭제
+        async deleteNote(noteId) {
+            if (!confirm('이 메모를 삭제하시겠습니까?')) {
+                return;
+            }
+            
+            try {
+                await window.api.deleteNote(noteId);
+                
+                // 로컬 데이터에서 제거
+                this.notes = this.notes.filter(n => n.id !== noteId);
+                
+                // 툴팁 새로고침
+                const highlight = this.highlights.find(h => 
+                    this.notes.some(n => n.highlight_id === h.id) || 
+                    document.querySelector(`[data-highlight-id="${h.id}"]`)
+                );
+                if (highlight) {
+                    const element = document.querySelector(`[data-highlight-id="${highlight.id}"]`);
+                    if (element) {
+                        this.showHighlightDetails(highlight, element);
+                    }
+                }
+                
+            } catch (error) {
+                console.error('Failed to delete note:', error);
+                alert('메모 삭제에 실패했습니다');
+            }
+        },
+        
+        // 하이라이트 삭제
+        async deleteHighlight(highlightId) {
+            if (!confirm('이 하이라이트를 삭제하시겠습니까? 연결된 메모도 함께 삭제됩니다.')) {
+                return;
+            }
+            
+            try {
+                await window.api.deleteHighlight(highlightId);
+                
+                // 로컬 데이터에서 제거
+                this.highlights = this.highlights.filter(h => h.id !== highlightId);
+                this.notes = this.notes.filter(n => n.highlight_id !== highlightId);
+                
+                // UI 업데이트
+                this.hideTooltip();
+                this.applyHighlights();
+                
+            } catch (error) {
+                console.error('Failed to delete highlight:', error);
+                alert('하이라이트 삭제에 실패했습니다');
+            }
+        },
+        
+        // 하이라이트 메모 업데이트
+        async updateHighlightNote(highlightId, note) {
+            try {
+                await window.api.updateHighlight(highlightId, { note });
+                const highlight = this.highlights.find(h => h.id === highlightId);
+                if (highlight) {
+                    highlight.note = note;
+                }
+                console.log('✅ 하이라이트 메모 업데이트 완료');
+            } catch (error) {
+                console.error('❌ 하이라이트 메모 업데이트 실패:', error);
+            }
+        },
+        
+        // 하이라이트 모드 토글
+        toggleHighlightMode() {
+            this.highlightMode = !this.highlightMode;
+            if (!this.highlightMode) {
+                this.showHighlightMenu = false;
+            }
+            console.log('🎨 하이라이트 모드:', this.highlightMode ? '활성화' : '비활성화');
+        },
+        
+        // 문서 편집
+        editDocument(document) {
+            console.log('✏️ 문서 편집:', document.title);
+            // TODO: 편집 모달 구현
+            alert('문서 편집 기능은 곧 구현될 예정입니다.');
+        },
+        
+        // 문서 삭제
+        async deleteDocument(documentId) {
+            if (!confirm('정말로 이 문서를 삭제하시겠습니까?')) {
+                return;
+            }
+            
+            try {
+                await window.api.deleteDocument(documentId);
+                console.log('✅ 문서 삭제 완료');
+                
+                // 선택된 문서가 삭제된 경우 선택 해제
+                if (this.selectedDocument && this.selectedDocument.id === documentId) {
+                    this.selectedDocument = null;
+                    this.documentContent = null;
+                }
+                
+                // 계층구조 새로고침
+                await this.loadHierarchy();
+            } catch (error) {
+                console.error('❌ 문서 삭제 실패:', error);
+                alert('문서 삭제 중 오류가 발생했습니다.');
+            }
+        },
+        
+        // 검색
+        async searchDocuments() {
+            // TODO: 검색 기능 구현
+            console.log('🔍 검색:', this.searchQuery);
+        },
+        
+        // 드래그 앤 드롭 처리
+        handleDragStart(event, document) {
+            this.draggedDocument = document;
+            event.dataTransfer.effectAllowed = 'move';
+            event.dataTransfer.setData('text/html', document.id);
+            
+            // 드래그 중인 요소 스타일
+            event.target.style.opacity = '0.5';
+        },
+        
+        handleDrop(event, targetCategoryId) {
+            event.preventDefault();
+            
+            if (!this.draggedDocument) return;
+            
+            console.log('📦 드롭:', this.draggedDocument.title, '→', targetCategoryId);
+            
+            // TODO: 문서 순서 변경 API 호출
+            // await window.api.updateDocumentOrder({
+            //     document_id: this.draggedDocument.id,
+            //     category_id: targetCategoryId,
+            //     new_order: targetOrder
+            // });
+            
+            // 드래그 상태 초기화
+            this.draggedDocument = null;
+            
+            // UI 새로고침
+            this.loadHierarchy();
+        },
+        
+        // 로그인 모달 열기
+        openLoginModal() {
+            this.showLoginModal = true;
+        },
+        
+        // 로그아웃
+        async logout() {
+            try {
+                await window.api.logout();
+                this.currentUser = null;
+                this.hierarchy = { books: {}, uncategorized: [] };
+                this.selectedDocument = null;
+                this.documentContent = null;
+                console.log('✅ 로그아웃 완료');
+            } catch (error) {
+                console.error('❌ 로그아웃 실패:', error);
+            }
+        }
+    };
+};
+
+// 업로드 모달 (기존 로직 재사용)
+window.uploadModal = function() {
+    return {
+        // 폼 데이터
+        uploadForm: {
+            html_file: null,
+            pdf_file: null,
+            title: '',
+            description: '',
+            document_date: '',
+            tags: '',
+            is_public: false
+        },
+        
+        // 서적 관련
+        bookSelectionMode: 'none',
+        bookSearchQuery: '',
+        searchedBooks: [],
+        selectedBook: null,
+        newBook: {
+            title: '',
+            author: ''
+        },
+        suggestions: [],
+        searchTimeout: null,
+        
+        // 상태
+        uploading: false,
+        uploadError: null,
+        
+        // 파일 선택 처리
+        handleFileSelect(event, fileType) {
+            const file = event.target.files[0];
+            if (file) {
+                this.uploadForm[fileType] = file;
+                console.log(`📎 ${fileType} 선택:`, file.name);
+            }
+        },
+        
+        // 서적 검색
+        async searchBooks() {
+            if (!this.bookSearchQuery.trim()) {
+                this.searchedBooks = [];
+                return;
+            }
+            
+            try {
+                const books = await window.api.searchBooks(this.bookSearchQuery);
+                this.searchedBooks = books;
+            } catch (error) {
+                console.error('❌ 서적 검색 실패:', error);
+            }
+        },
+        
+        // 서적 선택
+        selectBook(book) {
+            this.selectedBook = book;
+            this.searchedBooks = [];
+            this.bookSearchQuery = book.title;
+        },
+        
+        // 추천 서적 가져오기
+        async getSuggestions() {
+            if (!this.newBook.title.trim()) {
+                this.suggestions = [];
+                return;
+            }
+            
+            // 디바운스
+            if (this.searchTimeout) {
+                clearTimeout(this.searchTimeout);
+            }
+            
+            this.searchTimeout = setTimeout(async () => {
+                try {
+                    const suggestions = await window.api.getBookSuggestions(this.newBook.title);
+                    this.suggestions = suggestions;
+                } catch (error) {
+                    console.error('❌ 추천 가져오기 실패:', error);
+                }
+            }, 300);
+        },
+        
+        // 추천에서 기존 서적 선택
+        selectExistingFromSuggestion(suggestion) {
+            this.bookSelectionMode = 'existing';
+            this.selectedBook = suggestion;
+            this.suggestions = [];
+            this.newBook = { title: '', author: '' };
+        },
+        
+        // 업로드 실행
+        async upload() {
+            this.uploading = true;
+            this.uploadError = null;
+            
+            try {
+                const formData = new FormData();
+                
+                // 파일 추가
+                formData.append('html_file', this.uploadForm.html_file);
+                if (this.uploadForm.pdf_file) {
+                    formData.append('pdf_file', this.uploadForm.pdf_file);
+                }
+                
+                // 문서 정보 추가
+                formData.append('title', this.uploadForm.title);
+                formData.append('description', this.uploadForm.description || '');
+                formData.append('document_date', this.uploadForm.document_date || '');
+                formData.append('tags', this.uploadForm.tags || '');
+                formData.append('is_public', this.uploadForm.is_public);
+                
+                // 서적 정보 처리
+                let bookId = null;
+                
+                if (this.bookSelectionMode === 'existing' && this.selectedBook) {
+                    bookId = this.selectedBook.id;
+                } else if (this.bookSelectionMode === 'new' && this.newBook.title) {
+                    // 새 서적 생성
+                    const newBook = await window.api.createBook({
+                        title: this.newBook.title,
+                        author: this.newBook.author || null
+                    });
+                    bookId = newBook.id;
+                }
+                
+                if (bookId) {
+                    formData.append('book_id', bookId);
+                }
+                
+                // 업로드 실행
+                await window.api.uploadDocument(formData);
+                
+                console.log('✅ 문서 업로드 완료');
+                
+                // 성공 후 처리
+                this.closeUploadModal();
+                window.dispatchEvent(new CustomEvent('upload-complete'));
+                
+            } catch (error) {
+                console.error('❌ 업로드 실패:', error);
+                this.uploadError = error.message || '업로드 중 오류가 발생했습니다.';
+            } finally {
+                this.uploading = false;
+            }
+        },
+        
+        // 모달 닫기
+        closeUploadModal() {
+            this.showUploadModal = false;
+            this.resetForm();
+        },
+        
+        // 폼 초기화
+        resetForm() {
+            this.uploadForm = {
+                html_file: null,
+                pdf_file: null,
+                title: '',
+                description: '',
+                document_date: '',
+                tags: '',
+                is_public: false
+            };
+            this.bookSelectionMode = 'none';
+            this.bookSearchQuery = '';
+            this.searchedBooks = [];
+            this.selectedBook = null;
+            this.newBook = { title: '', author: '' };
+            this.suggestions = [];
+            this.uploadError = null;
+        }
+    };
+};
+
+// 로그인 모달 (기존 로직 재사용)
+window.authModal = function() {
+    return {
+        loginForm: {
+            email: '',
+            password: ''
+        },
+        loggingIn: false,
+        loginError: null,
+        
+        async login() {
+            this.loggingIn = true;
+            this.loginError = null;
+            
+            try {
+                const response = await window.api.login(this.loginForm.email, this.loginForm.password);
+                
+                // 토큰 저장
+                localStorage.setItem('access_token', response.access_token);
+                if (response.refresh_token) {
+                    localStorage.setItem('refresh_token', response.refresh_token);
+                }
+                
+                // 사용자 정보 가져오기
+                const user = await window.api.getCurrentUser();
+                
+                console.log('✅ 로그인 성공:', user.email);
+                
+                // 전역 이벤트 발생
+                window.dispatchEvent(new CustomEvent('auth-changed', {
+                    detail: { user }
+                }));
+                
+                // 모달 닫기
+                this.showLoginModal = false;
+                this.resetLoginForm();
+                
+            } catch (error) {
+                console.error('❌ 로그인 실패:', error);
+                this.loginError = error.message || '로그인에 실패했습니다.';
+            } finally {
+                this.loggingIn = false;
+            }
+        },
+        
+        resetLoginForm() {
+            this.loginForm = { email: '', password: '' };
+            this.loginError = null;
+        }
+    };
+};
+
+console.log('📚 계층구조 JavaScript 로드 완료');
diff --git a/frontend/static/js/main.js b/frontend/static/js/main.js
index be611df..714e45c 100644
--- a/frontend/static/js/main.js
+++ b/frontend/static/js/main.js
@@ -1,201 +1,239 @@
-/**
- * 메인 애플리케이션 Alpine.js 컴포넌트
- */
-
-// 메인 문서 앱 컴포넌트
+// 메인 애플리케이션 컴포넌트
 window.documentApp = () => ({
-    // 상태
-    isAuthenticated: false,
-    user: null,
-    loading: false,
-    
-    // 문서 관련
+    // 상태 관리
     documents: [],
-    tags: [],
-    selectedTag: '',
-    viewMode: 'grid', // 'grid' 또는 'list'
+    filteredDocuments: [],
+    loading: false,
+    error: '',
     
-    // 검색
+    // 인증 상태
+    isAuthenticated: false,
+    currentUser: null,
+    showLoginModal: false,
+    
+    // 필터링 및 검색
     searchQuery: '',
-    searchResults: [],
+    selectedTag: '',
+    availableTags: [],
+    
+    // UI 상태
+    viewMode: 'grid', // 'grid' 또는 'list'
+    user: null, // currentUser의 별칭
+    tags: [], // availableTags의 별칭
     
     // 모달 상태
-    showLoginModal: false,
     showUploadModal: false,
-    showProfile: false,
-    showMyNotes: false,
-    showBookmarks: false,
-    showAdmin: false,
-
+    
     // 초기화
     async init() {
-        // 인증 상태 확인
-        await this.checkAuth();
-        
-        // 인증 상태 변경 이벤트 리스너
-        window.addEventListener('auth-changed', (event) => {
-            this.isAuthenticated = event.detail.isAuthenticated;
-            this.user = event.detail.user;
-            
-            if (this.isAuthenticated) {
-                this.loadInitialData();
-            } else {
-                this.resetData();
-            }
-        });
-        
-        // 로그인 모달 닫기 이벤트 리스너
-        window.addEventListener('close-login-modal', () => {
-            this.showLoginModal = false;
-        });
-        
-        // 문서 변경 이벤트 리스너
-        window.addEventListener('documents-changed', () => {
-            if (this.isAuthenticated) {
-                this.loadDocuments();
-                this.loadTags();
-            }
-        });
-        
-        // 업로드 모달 닫기 이벤트 리스너
-        window.addEventListener('close-upload-modal', () => {
-            this.showUploadModal = false;
-        });
-        
-        // 알림 표시 이벤트 리스너
-        window.addEventListener('show-notification', (event) => {
-            if (this.showNotification) {
-                this.showNotification(event.detail.message, event.detail.type);
-            }
-        });
-        
-        // 초기 데이터 로드
+        await this.checkAuthStatus();
         if (this.isAuthenticated) {
-            await this.loadInitialData();
+            await this.loadDocuments();
         }
+        this.setupEventListeners();
     },
 
     // 인증 상태 확인
-    async checkAuth() {
-        if (!api.token) {
-            this.isAuthenticated = false;
-            return;
-        }
-
+    async checkAuthStatus() {
         try {
-            this.user = await api.getCurrentUser();
-            this.isAuthenticated = true;
-        } catch (error) {
-            console.error('Auth check failed:', error);
-            this.isAuthenticated = false;
-            api.setToken(null);
-        }
-    },
-
-    // 초기 데이터 로드
-    async loadInitialData() {
-        this.loading = true;
-        try {
-            await Promise.all([
-                this.loadDocuments(),
-                this.loadTags()
-            ]);
-        } catch (error) {
-            console.error('Failed to load initial data:', error);
-        } finally {
-            this.loading = false;
-        }
-    },
-
-    // 데이터 리셋
-    resetData() {
-        this.documents = [];
-        this.tags = [];
-        this.selectedTag = '';
-        this.searchQuery = '';
-        this.searchResults = [];
-    },
-
-    // 문서 목록 로드
-    async loadDocuments() {
-        try {
-            const response = await api.getDocuments();
-            let allDocuments = response || [];
-            
-            // 태그 필터링
-            let filteredDocs = allDocuments;
-            if (this.selectedTag) {
-                filteredDocs = allDocuments.filter(doc => 
-                    doc.tags && doc.tags.includes(this.selectedTag)
-                );
+            const token = localStorage.getItem('access_token');
+            if (token) {
+                window.api.setToken(token);
+                const user = await window.api.getCurrentUser();
+                this.isAuthenticated = true;
+                this.currentUser = user;
+                this.syncUIState(); // UI 상태 동기화
             }
-            
-            this.documents = filteredDocs;
         } catch (error) {
-            console.error('Failed to load documents:', error);
-            this.documents = [];
-            this.showNotification('문서 목록을 불러오는데 실패했습니다', 'error');
+            console.log('Not authenticated or token expired');
+            this.isAuthenticated = false;
+            this.currentUser = null;
+            localStorage.removeItem('access_token');
+            this.syncUIState(); // UI 상태 동기화
         }
     },
 
-    // 태그 목록 로드
-    async loadTags() {
-        try {
-            const response = await api.getTags();
-            this.tags = response || [];
-        } catch (error) {
-            console.error('Failed to load tags:', error);
-            this.tags = [];
-        }
-    },
-
-    // 문서 검색
-    async searchDocuments() {
-        if (!this.searchQuery.trim()) {
-            this.searchResults = [];
-            return;
-        }
-
-        try {
-            const results = await api.search({ 
-                q: this.searchQuery,
-                limit: 20 
-            });
-            this.searchResults = results.results;
-        } catch (error) {
-            console.error('Search failed:', error);
-        }
-    },
-
-    // 문서 열기
-    openDocument(document) {
-        // 문서 뷰어 페이지로 이동
-        window.location.href = `/viewer.html?id=${document.id}`;
+    // 로그인 모달 열기
+    openLoginModal() {
+        this.showLoginModal = true;
     },
 
     // 로그아웃
     async logout() {
         try {
-            await api.logout();
-            this.isAuthenticated = false;
-            this.user = null;
-            this.resetData();
+            await window.api.logout();
         } catch (error) {
-            console.error('Logout failed:', error);
+            console.error('Logout error:', error);
+        } finally {
+            this.isAuthenticated = false;
+            this.currentUser = null;
+            localStorage.removeItem('access_token');
+            localStorage.removeItem('refresh_token');
+            this.documents = [];
+            this.filteredDocuments = [];
+        }
+    },
+    
+    // 이벤트 리스너 설정
+    setupEventListeners() {
+        // 문서 변경 이벤트 리스너
+        window.addEventListener('documents-changed', () => {
+            this.loadDocuments();
+        });
+        
+        // 알림 이벤트 리스너
+        window.addEventListener('show-notification', (event) => {
+            this.showNotification(event.detail.message, event.detail.type);
+        });
+
+        // 인증 상태 변경 이벤트 리스너
+        window.addEventListener('auth-changed', (event) => {
+            this.isAuthenticated = event.detail.isAuthenticated;
+            this.currentUser = event.detail.user;
+            this.showLoginModal = false;
+            this.syncUIState(); // UI 상태 동기화
+            if (this.isAuthenticated) {
+                this.loadDocuments();
+            }
+        });
+
+        // 로그인 모달 닫기 이벤트 리스너
+        window.addEventListener('close-login-modal', () => {
+            this.showLoginModal = false;
+        });
+    },
+
+    // 문서 목록 로드
+    async loadDocuments() {
+        this.loading = true;
+        this.error = '';
+        
+        try {
+            this.documents = await window.api.getDocuments();
+            this.updateAvailableTags();
+            this.filterDocuments();
+            this.syncUIState(); // UI 상태 동기화
+        } catch (error) {
+            console.error('Failed to load documents:', error);
+            this.error = 'Failed to load documents: ' + error.message;
+            this.documents = [];
+        } finally {
+            this.loading = false;
         }
     },
 
-    // 문서 뷰어 열기
+    // 사용 가능한 태그 업데이트
+    updateAvailableTags() {
+        const tagSet = new Set();
+        this.documents.forEach(doc => {
+            if (doc.tags) {
+                doc.tags.forEach(tag => tagSet.add(tag));
+            }
+        });
+        this.availableTags = Array.from(tagSet).sort();
+        this.tags = this.availableTags; // 별칭 동기화
+    },
+
+    // UI 상태 동기화
+    syncUIState() {
+        this.user = this.currentUser;
+        this.tags = this.availableTags;
+    },
+
+    // 문서 필터링
+    filterDocuments() {
+        let filtered = this.documents;
+
+        // 검색어 필터링
+        if (this.searchQuery) {
+            const query = this.searchQuery.toLowerCase();
+            filtered = filtered.filter(doc => 
+                doc.title.toLowerCase().includes(query) ||
+                (doc.description && doc.description.toLowerCase().includes(query)) ||
+                (doc.tags && doc.tags.some(tag => tag.toLowerCase().includes(query)))
+            );
+        }
+
+        // 태그 필터링
+        if (this.selectedTag) {
+            filtered = filtered.filter(doc => 
+                doc.tags && doc.tags.includes(this.selectedTag)
+            );
+        }
+
+        this.filteredDocuments = filtered;
+    },
+
+    // 검색어 변경 시
+    onSearchChange() {
+        this.filterDocuments();
+    },
+
+    // 문서 검색 (HTML에서 사용)
+    searchDocuments() {
+        this.filterDocuments();
+    },
+
+    // 태그 선택 시
+    onTagSelect(tag) {
+        this.selectedTag = this.selectedTag === tag ? '' : tag;
+        this.filterDocuments();
+    },
+
+    // 태그 필터 초기화
+    clearTagFilter() {
+        this.selectedTag = '';
+        this.filterDocuments();
+    },
+
+    // 문서 삭제
+    async deleteDocument(documentId) {
+        if (!confirm('정말로 이 문서를 삭제하시겠습니까?')) {
+            return;
+        }
+
+        try {
+            await window.api.deleteDocument(documentId);
+            await this.loadDocuments();
+            this.showNotification('문서가 삭제되었습니다', 'success');
+        } catch (error) {
+            console.error('Failed to delete document:', error);
+            this.showNotification('문서 삭제에 실패했습니다: ' + error.message, 'error');
+        }
+    },
+
+    // 문서 보기
+    viewDocument(documentId) {
+        window.open(`/viewer.html?id=${documentId}`, '_blank');
+    },
+
+    // 문서 열기 (HTML에서 사용)
     openDocument(documentId) {
-        window.location.href = `/viewer.html?id=${documentId}`;
+        this.viewDocument(documentId);
+    },
+
+    // 문서 수정 (HTML에서 사용)
+    editDocument(document) {
+        // TODO: 문서 수정 모달 구현
+        console.log('문서 수정:', document);
+        alert('문서 수정 기능은 곧 구현됩니다!');
+    },
+
+    // 업로드 모달 열기
+    openUploadModal() {
+        this.showUploadModal = true;
+    },
+
+    // 업로드 모달 닫기
+    closeUploadModal() {
+        this.showUploadModal = false;
     },
 
     // 날짜 포맷팅
     formatDate(dateString) {
-        const date = new Date(dateString);
-        return date.toLocaleDateString('ko-KR', {
+        return new Date(dateString).toLocaleDateString('ko-KR', {
             year: 'numeric',
-            month: 'short',
+            month: 'long',
             day: 'numeric'
         });
     },
@@ -221,7 +259,6 @@ window.documentApp = () => ({
 
 // 파일 업로드 컴포넌트
 window.uploadModal = () => ({
-    show: false,
     uploading: false,
     uploadForm: {
         title: '',
@@ -233,6 +270,19 @@ window.uploadModal = () => ({
         pdf_file: null
     },
     uploadError: '',
+    
+    // 서적 관련 상태
+    bookSelectionMode: 'none', // 'existing', 'new', 'none'
+    bookSearchQuery: '',
+    searchedBooks: [],
+    selectedBook: null,
+    newBook: {
+        title: '',
+        author: '',
+        description: ''
+    },
+    suggestions: [],
+    searchTimeout: null,
 
     // 파일 선택
     onFileSelect(event, fileType) {
@@ -247,15 +297,44 @@ window.uploadModal = () => ({
         }
     },
 
+    // 드래그 앤 드롭 처리
+    handleFileDrop(event, fileType) {
+        event.target.classList.remove('dragover');
+        const files = event.dataTransfer.files;
+        if (files.length > 0) {
+            const file = files[0];
+            
+            // 파일 타입 검증
+            if (fileType === 'html_file' && !file.name.match(/\.(html|htm)$/i)) {
+                this.uploadError = 'HTML 파일만 업로드 가능합니다';
+                return;
+            }
+            
+            if (fileType === 'pdf_file' && !file.name.match(/\.pdf$/i)) {
+                this.uploadError = 'PDF 파일만 업로드 가능합니다';
+                return;
+            }
+            
+            this.uploadForm[fileType] = file;
+            this.uploadError = '';
+            
+            // HTML 파일의 경우 제목 자동 설정
+            if (fileType === 'html_file' && !this.uploadForm.title) {
+                this.uploadForm.title = file.name.replace(/\.[^/.]+$/, "");
+            }
+        }
+    },
+
     // 업로드 실행
     async upload() {
+        // 필수 필드 검증
         if (!this.uploadForm.html_file) {
             this.uploadError = 'HTML 파일을 선택해주세요';
             return;
         }
-
+        
         if (!this.uploadForm.title.trim()) {
-            this.uploadError = '제목을 입력해주세요';
+            this.uploadError = '문서 제목을 입력해주세요';
             return;
         }
 
@@ -263,25 +342,52 @@ window.uploadModal = () => ({
         this.uploadError = '';
 
         try {
+            let bookId = null;
+
+            // 서적 처리
+            if (this.bookSelectionMode === 'new' && this.newBook.title.trim()) {
+                const newBook = await window.api.createBook({
+                    title: this.newBook.title,
+                    author: this.newBook.author || null,
+                    description: this.newBook.description || null,
+                    language: this.uploadForm.language || 'ko',
+                    is_public: this.uploadForm.is_public
+                });
+                bookId = newBook.id;
+            } else if (this.bookSelectionMode === 'existing' && this.selectedBook) {
+                bookId = this.selectedBook.id;
+            }
+
+            // FormData 생성
             const formData = new FormData();
             formData.append('title', this.uploadForm.title);
-            formData.append('description', this.uploadForm.description);
-            formData.append('tags', this.uploadForm.tags);
-            formData.append('is_public', this.uploadForm.is_public);
+            formData.append('description', this.uploadForm.description || '');
             formData.append('html_file', this.uploadForm.html_file);
             
             if (this.uploadForm.pdf_file) {
                 formData.append('pdf_file', this.uploadForm.pdf_file);
             }
             
+            // 서적 ID 추가
+            if (bookId) {
+                formData.append('book_id', bookId);
+            }
+            
+            formData.append('language', this.uploadForm.language || 'ko');
+            formData.append('is_public', this.uploadForm.is_public);
+            
+            if (this.uploadForm.tags) {
+                formData.append('tags', this.uploadForm.tags);
+            }
+            
             if (this.uploadForm.document_date) {
                 formData.append('document_date', this.uploadForm.document_date);
             }
 
-            await api.uploadDocument(formData);
+            // 업로드 실행
+            await window.api.uploadDocument(formData);
             
-            // 성공시 모달 닫기 및 목록 새로고침
-            this.show = false;
+            // 성공 처리
             this.resetForm();
             
             // 문서 목록 새로고침
@@ -315,138 +421,66 @@ window.uploadModal = () => ({
         // 파일 입력 필드 리셋
         const fileInputs = document.querySelectorAll('input[type="file"]');
         fileInputs.forEach(input => input.value = '');
-    }
-});
-
-// 파일 업로드 컴포넌트
-window.uploadModal = () => ({
-    uploading: false,
-    uploadForm: {
-        title: '',
-        description: '',
-        tags: '',
-        is_public: false,
-        document_date: '',
-        html_file: null,
-        pdf_file: null
-    },
-    uploadError: '',
-
-    // 파일 선택
-    onFileSelect(event, fileType) {
-        const file = event.target.files[0];
-        if (file) {
-            this.uploadForm[fileType] = file;
-            
-            // HTML 파일의 경우 제목 자동 설정
-            if (fileType === 'html_file' && !this.uploadForm.title) {
-                this.uploadForm.title = file.name.replace(/\.[^/.]+$/, "");
-            }
-        }
-    },
-
-    // 드래그 앤 드롭 처리
-    handleFileDrop(event, fileType) {
-        event.target.classList.remove('dragover');
-        const files = event.dataTransfer.files;
-        if (files.length > 0) {
-            const file = files[0];
-            
-            // 파일 타입 검증
-            if (fileType === 'html_file' && !file.name.match(/\.(html|htm)$/i)) {
-                this.uploadError = 'HTML 파일만 업로드 가능합니다';
-                return;
-            }
-            if (fileType === 'pdf_file' && !file.name.match(/\.pdf$/i)) {
-                this.uploadError = 'PDF 파일만 업로드 가능합니다';
-                return;
-            }
-            
-            this.uploadForm[fileType] = file;
-            this.uploadError = '';
-            
-            // HTML 파일의 경우 제목 자동 설정
-            if (fileType === 'html_file' && !this.uploadForm.title) {
-                this.uploadForm.title = file.name.replace(/\.[^/.]+$/, "");
-            }
-        }
-    },
-
-    // 업로드 실행 (목업)
-    async upload() {
-        if (!this.uploadForm.html_file) {
-            this.uploadError = 'HTML 파일을 선택해주세요';
-            return;
-        }
-
-        if (!this.uploadForm.title.trim()) {
-            this.uploadError = '제목을 입력해주세요';
-            return;
-        }
-
-        this.uploading = true;
-        this.uploadError = '';
-
-        try {
-            // FormData 생성
-            const formData = new FormData();
-            formData.append('title', this.uploadForm.title);
-            formData.append('description', this.uploadForm.description || '');
-            formData.append('html_file', this.uploadForm.html_file);
-            
-            if (this.uploadForm.pdf_file) {
-                formData.append('pdf_file', this.uploadForm.pdf_file);
-            }
-            
-            formData.append('language', this.uploadForm.language);
-            formData.append('is_public', this.uploadForm.is_public);
-            
-            // 태그 추가
-            if (this.uploadForm.tags && this.uploadForm.tags.length > 0) {
-                this.uploadForm.tags.forEach(tag => {
-                    formData.append('tags', tag);
-                });
-            }
-            
-            // 실제 API 호출
-            await api.uploadDocument(formData);
-            
-            // 성공시 모달 닫기 및 목록 새로고침
-            window.dispatchEvent(new CustomEvent('close-upload-modal'));
-            this.resetForm();
-            
-            // 문서 목록 새로고침
-            window.dispatchEvent(new CustomEvent('documents-changed'));
-            
-            // 성공 알림
-            window.dispatchEvent(new CustomEvent('show-notification', { 
-                detail: { message: '문서가 성공적으로 업로드되었습니다', type: 'success' } 
-            }));
-            
-        } catch (error) {
-            this.uploadError = error.message || '업로드에 실패했습니다';
-        } finally {
-            this.uploading = false;
-        }
-    },
-
-    // 폼 리셋
-    resetForm() {
-        this.uploadForm = {
-            title: '',
-            description: '',
-            tags: '',
-            is_public: false,
-            document_date: '',
-            html_file: null,
-            pdf_file: null
-        };
-        this.uploadError = '';
         
-        // 파일 입력 필드 리셋
-        const fileInputs = document.querySelectorAll('input[type="file"]');
-        fileInputs.forEach(input => input.value = '');
+        // 서적 관련 상태 리셋
+        this.bookSelectionMode = 'none';
+        this.bookSearchQuery = '';
+        this.searchedBooks = [];
+        this.selectedBook = null;
+        this.newBook = { title: '', author: '', description: '' };
+        this.suggestions = [];
+        if (this.searchTimeout) {
+            clearTimeout(this.searchTimeout);
+            this.searchTimeout = null;
+        }
+    },
+
+    // 서적 검색
+    async searchBooks() {
+        if (!this.bookSearchQuery.trim()) {
+            this.searchedBooks = [];
+            return;
+        }
+        try {
+            const books = await window.api.searchBooks(this.bookSearchQuery, 10);
+            this.searchedBooks = books;
+        } catch (error) {
+            console.error('서적 검색 실패:', error);
+            this.searchedBooks = [];
+        }
+    },
+
+    // 서적 선택
+    selectBook(book) {
+        this.selectedBook = book;
+        this.bookSearchQuery = book.title;
+        this.searchedBooks = [];
+    },
+
+    // 유사도 추천 가져오기
+    async getSuggestions() {
+        if (!this.newBook.title.trim()) {
+            this.suggestions = [];
+            return;
+        }
+        clearTimeout(this.searchTimeout);
+        this.searchTimeout = setTimeout(async () => {
+            try {
+                const suggestions = await window.api.getBookSuggestions(this.newBook.title, 3);
+                this.suggestions = suggestions.filter(s => s.similarity_score > 0.5); // 50% 이상 유사한 것만
+            } catch (error) {
+                console.error('추천 가져오기 실패:', error);
+                this.suggestions = [];
+            }
+        }, 300);
+    },
+
+    // 추천에서 기존 서적 선택
+    selectExistingFromSuggestion(suggestion) {
+        this.bookSelectionMode = 'existing';
+        this.selectedBook = suggestion;
+        this.bookSearchQuery = suggestion.title;
+        this.suggestions = [];
+        this.newBook = { title: '', author: '', description: '' };
     }
-});
-
-
+});
\ No newline at end of file
diff --git a/frontend/test.html b/frontend/test.html
new file mode 100644
index 0000000..b6376a5
--- /dev/null
+++ b/frontend/test.html
@@ -0,0 +1,24 @@
+<!DOCTYPE html>
+<html lang="ko">
+<head>
+    <meta charset="UTF-8">
+    <meta name="viewport" content="width=device-width, initial-scale=1.0">
+    <title>테스트 페이지</title>
+    <script src="https://cdn.tailwindcss.com"></script>
+    <script src="https://unpkg.com/alpinejs@3.x.x/dist/cdn.min.js" defer></script>
+</head>
+<body class="bg-gray-100 p-8">
+    <div x-data="{ message: '페이지가 정상 작동합니다!' }">
+        <h1 class="text-3xl font-bold text-blue-600 mb-4" x-text="message"></h1>
+        <p class="text-gray-700">이 페이지가 보이면 기본 설정은 정상입니다.</p>
+        
+        <div class="mt-8">
+            <h2 class="text-xl font-semibold mb-4">링크</h2>
+            <div class="space-y-2">
+                <a href="index.html" class="block px-4 py-2 bg-blue-500 text-white rounded hover:bg-blue-600">그리드 뷰</a>
+                <a href="hierarchy.html" class="block px-4 py-2 bg-green-500 text-white rounded hover:bg-green-600">계층구조 뷰</a>
+            </div>
+        </div>
+    </div>
+</body>
+</html>