KR100788127B1 - 감방사선성 수지 조성물 - Google Patents
감방사선성 수지 조성물 Download PDFInfo
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- KR100788127B1 KR100788127B1 KR1020020002703A KR20020002703A KR100788127B1 KR 100788127 B1 KR100788127 B1 KR 100788127B1 KR 1020020002703 A KR1020020002703 A KR 1020020002703A KR 20020002703 A KR20020002703 A KR 20020002703A KR 100788127 B1 KR100788127 B1 KR 100788127B1
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
- Y10S430/123—Sulfur in heterocyclic ring
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
수지 (부) | 산발생제 (B) (부) | 산확산 제어제 (부) | 다른 첨가제 (부) | 용매 (부) | |
실시예 1 | A-1 (100) | B-1 (2.0) b-1 (1.0) | C-1 (0.10) | - | E-1 (530) |
실시예 2 | A-1 (80) A-2 (10) | B-1 (3.0) | C-4 (0.05) | D-1 (10) | E-1 (430) E-2 (100) |
실시예 3 | A-3 (95) | B-2 (2.0) b-2 (2.0) | C-2 (0.10) | D-2 (5) | E-1 (430) E-4 (100) |
실시예 4 | A-2 (10) A-3 (80) | B-3 (3.0) b-3 (2.0) | C-3 (0.10) | D-3 (10) | E-3 (530) |
실시예 5 | A-4 (100) | B-1 (2.0) b-4 (3.0) | C-5 (0.05) | - | E-1 (530) |
실시예 6 | A-5 (90) | B-3 (2.0) b-4 (2.0) | C-5 (0.05) | D-3 (10) | E-1 (430) E-2 (100) |
실시예 7 | A-2 (10) A-5 (80) | B-2 (3.0) b-4 (2.0) | C-3 (0.05) C-5 (0.03) | D-2 (10) | E-3 (430) E-4 (100) |
실시예 8 | A-6 (90) | B-3 (5.0) | C-5 (0.10) | D-3 (10) | E-3 (530) |
실시예 9 | A-7 (100) | B-2 (5.0) | C-5 (0.10) | - | E-1 (530) |
실시예 10 | A-8 (90) | B-3 (5.0) | C-5 (0.10) | D-3 (10) | E-3 (530) |
실시예 11 | A-7 (100) | B-2 (4.0) b-2 (1.0) | C-5 (0.10) | - | E-1 (430) E-2 (100) |
실시예 12 | A-1 (90) | B-3 (5.0) | C-5 (0.10) | D-3 (10) | E-3 (530) |
비교예 1 | a-1 (90) | b-1 (2.0) | C-1 (0.05) | D-1 (10) | E-1 (530) |
레지스트 피막의 막두께 (㎛) | 기판 | PB | PEB | |||
온도 (℃) | 시간 (초) | 온도 (℃) | 시간 (초) | |||
실시예 1 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 2 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 3 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 4 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 5 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 6 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 7 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 8 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 9 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 10 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 11 | 0.4 | ARC | 130 | 90 | 140 | 90 |
실시예 12 | 0.4 | ARC | 130 | 90 | 140 | 90 |
비교예 1 | 0.4 | ARC | 130 | 90 | 140 | 90 |
방사선 투과율 (193 nm, %) | 감도 (J/m2) | 해상도 (㎛) | 드라이 에칭 내성 | 패턴 형상 | |
실시예 1 | 72 | 89 | 0.15 | 0.8 | 양호 |
실시예 2 | 74 | 95 | 0.15 | 0.6 | 양호 |
실시예 3 | 69 | 79 | 0.15 | 0.7 | 양호 |
실시예 4 | 70 | 85 | 0.15 | 0.8 | 양호 |
실시예 5 | 69 | 81 | 0.15 | 0.5 | 양호 |
실시예 6 | 73 | 86 | 0.15 | 0.7 | 양호 |
실시예 7 | 72 | 92 | 0.15 | 0.6 | 양호 |
실시예 8 | 71 | 90 | 0.15 | 0.8 | 양호 |
실시예 9 | 68 | 79 | 0.15 | 0.7 | 양호 |
실시예 10 | 71 | 90 | 0.15 | 0.8 | 양호 |
실시예 11 | 67 | 81 | 0.15 | 0.7 | 양호 |
실시예 12 | 70 | 95 | 0.15 | 0.8 | 양호 |
비교예 1 | 61 | 150 | 0.15 | 1.0 | 양호 |
Claims (14)
- (A) 하기 화학식 1로 표시된 반복 단위 및 하기 화학식 2로 표시된 반복 단위를 갖는 알칼리 불용성 또는 알칼리 난용성의 산해리성기 함유 수지로서, 이 산해리성기가 해리되었을 때 알칼리 가용성이 되는 수지, 및 (B) 하기 화학식 3으로 표시되는 감방사선성 산발생제를 함유하는 것을 특징으로 하는 감방사선성 수지 조성물.<화학식 1><화학식 2>화학식 1에서, R1 및 R2는 서로 독립적으로 수소 원자 또는 메틸기를 나타내며, 화학식 2에서 R3은 수소 원자 또는 메틸기를 나타내고, -COOC(R4)3은 하기 화학식 (I-1), (I-2), (I-10), (I-11), (I-13), (I-14), (I-16), (I-17), (I-34), (I-35), (I-40), (I-41), (I-43) 및 (I-44)로 이루어진 군으로부터 선택된 1종을 나타낸다.<화학식 3>화학식 3에서, R5는 탄소수 6 내지 20의 1가 방향족 탄화수소기 또는 그 유도체를 나타내고, m은 1 내지 8의 정수이고, n은 0 내지 5의 정수이다.
- 삭제
- 삭제
- 삭제
- 제1항에 있어서, (A)수지에서 전체 반복 단위에 대한 화학식 1로 표시되는 반복 단위의 함유율이 10 내지 80 몰%, 화학식 2로 표시되는 반복 단위의 함유율이 10 내지 8O 몰%인 감방사선성 수지 조성물.
- 제1항에 있어서, 화학식 3에서 R5가 3,5-디메틸-4-히드록시페닐기, 4-메톡시페닐기, 4-n-부톡시페닐기, 2,4-디메톡시페닐기, 3,5-디메톡시페닐기, 4-n-부톡시-1-나프틸기로부터 선택되는 1종 이상인 감방사선성 수지 조성물.
- 제1항에 있어서, 화학식 3에서 m이 4 또는 8인 감방사선성 수지 조성물.
- 제1항에 있어서, 화학식 3에서 n이 1인 감방사선성 수지 조성물.
- 제1항에 있어서, 다른 감방사선성 산발생제를 더 함유하는 감방사선성 수지 조성물.
- 제9항에 있어서, 다른 감방사선성 산발생제의 비율이 전체 감방사선성 산발생제의 80 중량% 이하인 감방사선성 수지 조성물.
- 제1항에 있어서, 산확산 제어제를 추가로 함유하는 감방사선성 수지 조성물.
- 제11항에 있어서, 산확산 제어제로서 질소 함유 유기 화합물을 함유하는 감방사선성 수지 조성물.
- 제1항에 있어서, 산해리성기를 갖는 지환족 첨가제를 추가로 함유하는 감방사선성 수지 조성물.
- 제1항에 있어서, 용매로 직쇄 또는 분지쇄 케톤류, 환상 케톤류, 프로필렌글 리콜모노알킬에테르아세테이트류, 2-히드록시프로피온산알킬류 및 3-알콕시프로피온산 알킬류에서 선택되는 1종 이상을 함유하는 감방사선성 수지 조성물.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JPJP-P-2001-00010005 | 2001-01-18 | ||
JP2001010005 | 2001-01-18 |
Publications (2)
Publication Number | Publication Date |
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KR20020062196A KR20020062196A (ko) | 2002-07-25 |
KR100788127B1 true KR100788127B1 (ko) | 2007-12-21 |
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Application Number | Title | Priority Date | Filing Date |
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KR1020020002703A KR100788127B1 (ko) | 2001-01-18 | 2002-01-17 | 감방사선성 수지 조성물 |
Country Status (5)
Country | Link |
---|---|
US (1) | US6838225B2 (ko) |
EP (1) | EP1225480B1 (ko) |
KR (1) | KR100788127B1 (ko) |
DE (1) | DE60235663D1 (ko) |
TW (1) | TWI295409B (ko) |
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JP2002357905A (ja) | 2001-03-28 | 2002-12-13 | Sumitomo Chem Co Ltd | レジスト組成物 |
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US7531286B2 (en) * | 2002-03-15 | 2009-05-12 | Jsr Corporation | Radiation-sensitive resin composition |
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TWI314943B (en) * | 2002-08-29 | 2009-09-21 | Radiation-sensitive resin composition | |
JP3937996B2 (ja) * | 2002-10-08 | 2007-06-27 | Jsr株式会社 | 感放射性樹脂組成物 |
JP4357830B2 (ja) * | 2002-12-02 | 2009-11-04 | 東京応化工業株式会社 | レジスト用(メタ)アクリル酸誘導体ポリマーの製造方法 |
US7005230B2 (en) * | 2003-01-16 | 2006-02-28 | Jsr Corporation | Radiation-sensitive resin composition |
JP4772288B2 (ja) | 2003-06-05 | 2011-09-14 | 東京応化工業株式会社 | ホトレジスト組成物用樹脂、ホトレジスト組成物、およびレジストパターン形成方法 |
JP4327003B2 (ja) * | 2003-07-01 | 2009-09-09 | 東京応化工業株式会社 | ポジ型レジスト組成物及びそれを用いたレジストパターン形成方法 |
DE602004018648D1 (de) * | 2003-08-05 | 2009-02-05 | Jsr Corp | Acrylpolymere und strahlungsempfindliche harzzusammensetzung |
US7488565B2 (en) * | 2003-10-01 | 2009-02-10 | Chevron U.S.A. Inc. | Photoresist compositions comprising diamondoid derivatives |
JP4188265B2 (ja) * | 2003-10-23 | 2008-11-26 | 東京応化工業株式会社 | レジスト組成物およびレジストパターン形成方法 |
JP4140506B2 (ja) * | 2003-10-28 | 2008-08-27 | Jsr株式会社 | 感放射線性樹脂組成物 |
EP1574903A1 (en) | 2004-03-08 | 2005-09-14 | Rohm and Haas Electronic Materials, L.L.C. | Photoresists comprising cyanoadamantyl moiety-containing polymers |
EP1586944A1 (en) * | 2004-03-09 | 2005-10-19 | Rohm and Haas Electronic Materials, L.L.C. | Cyanoadamantyl compounds and polymers |
JP4732046B2 (ja) * | 2005-07-20 | 2011-07-27 | 東京応化工業株式会社 | レジスト組成物およびレジストパターン形成方法 |
WO2009116253A1 (ja) * | 2008-03-17 | 2009-09-24 | ダイセル化学工業株式会社 | 重合体の製造方法 |
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KR101956925B1 (ko) * | 2011-09-30 | 2019-03-11 | 제이에스알 가부시끼가이샤 | 레지스트 하층막 형성용 조성물, 레지스트 하층막 및 그의 형성 방법, 및 패턴 형성 방법 |
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2002
- 2002-01-16 US US10/046,080 patent/US6838225B2/en not_active Expired - Lifetime
- 2002-01-17 TW TW091100654A patent/TWI295409B/zh not_active IP Right Cessation
- 2002-01-17 KR KR1020020002703A patent/KR100788127B1/ko active IP Right Grant
- 2002-01-17 DE DE60235663T patent/DE60235663D1/de not_active Expired - Lifetime
- 2002-01-17 EP EP02001244A patent/EP1225480B1/en not_active Expired - Lifetime
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Also Published As
Publication number | Publication date |
---|---|
US20020132181A1 (en) | 2002-09-19 |
DE60235663D1 (de) | 2010-04-29 |
EP1225480A2 (en) | 2002-07-24 |
TWI295409B (en) | 2008-04-01 |
EP1225480B1 (en) | 2010-03-17 |
EP1225480A3 (en) | 2003-03-26 |
US6838225B2 (en) | 2005-01-04 |
KR20020062196A (ko) | 2002-07-25 |
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