TWI225186B - Positive photosensitive composition - Google Patents

Positive photosensitive composition Download PDF

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Publication number
TWI225186B
TWI225186B TW091113605A TW91113605A TWI225186B TW I225186 B TWI225186 B TW I225186B TW 091113605 A TW091113605 A TW 091113605A TW 91113605 A TW91113605 A TW 91113605A TW I225186 B TWI225186 B TW I225186B
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positive
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Kunihiko Kodama
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Fuji Photo Film Co Ltd
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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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
    • 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
    • G03F7/0395—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 a backbone with alicyclic moieties
    • 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
    • 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
    • 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
    • Y10S430/115—Cationic or anionic
    • 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
    • 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
    • Y10S430/124—Carbonyl compound containing

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Ceramic Engineering (AREA)
  • Materials For Photolithography (AREA)

Description

1225186 更正本 六、申請專利範圍 ?22
Rzb C—CH—C—Π 24 (pV) ο
—C—ο—ρ I
(pVl) 其中Ru表示甲基、乙基、正丙基、異丙基、正丁基、 異丁基、或第二丁基：Z表示與碳原子一起形成脂環烴 基所需之原子基；Ri2至Ri6各獨立地表示具有1至4 個碳原子之直鏈或分支烷基或脂環烴基，其條件爲Rl 2 至Rm至少之一及R1S或R,6表示脂環烴基；Rl7至r21 各獨立地表示氫原子、具有1至4個碳原子之直鏈或分 支烷基、或脂環烴基，其條件爲R17至R2I至少之一表 示脂環烴基，及R19或R21表示具有1至4個碳原子之 直鏈或分支烷基、或脂環烴基·，及R22至R25各獨立地 表示具有1至4個碳原子之直鏈或分支烷基、或脂環烴 基’其條件爲Κ·22至Κ·25至少之一表不脂環煙基，或Κ·23 與R24可彼此組合形成環，
(ll-A) (H-B) R13 Ρ,/15 -3 - 1225186 更正本 六、申請專利範圍 其中rI3'至r16'可爲相同或不同，各獨立地表示氫原子 、鹵素原子、氰基、-COOH、-COOR5、可藉酸之作用分 解之基、-CbCO-X-Ai-R,,，、可具有取代基之C,-C4烷基 ;R5表示可具有取代基之烷基、可具有取代基之 C7-C25環形烴基、或Y表示之基；X表示氧原子、硫原 子、-NH-、-NHS〇2-、或-NHS02-NH-: A·表示單鍵或二 價鍵聯基；或Ri3·至RW至少之二可彼此組合形成環：η 表示 0 或 1 ; R17•表示-COOH、-COOR5、-CN.、羥基、 可具有取代基之C,-C4烷氧基、-CO-NH-R6、-CO-NH· so2-r6、或Y表示之基：R6表示可具有取代基之C,-C4 烷基；及Y表示之基具有下式：
其中R21'至R3q’可爲相同或不同，各獨立地表示氫原子 或可具有取代基之C^-CU烷基；及a及b各表示1或2 〇 2.如申請專利範圍第1項之正型光敏劑組成物，其中成分 (B)之樹脂含具有內酯結構之重複單位。 3 .如申請專利範圍第1項之正型光敏劑組成物，其中成分 (A1)之化合物爲锍鹽。 4.如申請專利範圍第1項之正型光敏劑組成物，其中成分 (A 1)之在以光化射線或輻射照射時產生α -位置經氟原子 -4 - 1.225186 更正本 六、申請專利範圍 取代之烷屬磺酸之化合物爲鏑鹽，其由陰離子部份與陽 離子部份組成，由以下式（A1)表示：
其中R1、R2與R3可爲相同或不同，各獨立地表示有機 殘基，或R1、R2與R3之二可彼此組合形成環，及此環 可含氧原子、硫原子、酯鍵、醯胺基鍵、或羰基；及Z· 表示陰離子爲在α-位置之碳原子經氟取代之烷屬磺酸 陰離子。 5. 如申請專利範圍第4項之正型光敏劑組成物，其中锍鹽 爲式（Α1)表示之化合物，其中R1、R2與R3可爲相同或 不同，各表示芳基。 6. 如申請專利範圍第4項之正型光敏劑組成物，其中锍鹽 爲式（Α1)表示之化合物，其中R1、R2與R3可爲相同或 不同’各獨立地表示不含芳族環之有機殘基。 7 .如申請專利範圍第4項之正型光敏劑組成物，其中锍鹽 爲以下式（Α1-3)表示之化合物：
5 1225186 更正本 六、申請專利範圍 其中Ric至Rs。可爲相同或不同，各獨立地表示氫原子 、Cm院基、Cl 5烷氧基、或鹵素原子；R6c與可爲 相同或不同’各獨立地表示氫原子、C|5烷基或苯基； 與Ry可爲相同或不同’各獨立地表示Ci 5烷基、 氧院基、C,—5烷氧基羰基甲基、烯丙基、或乙烯基， 或Rle至Rk及1^與心之二或更多個各可彼此組合形 成環結構，及環結構可含氧原子、硫原子、酯鍵、或醯 胺基鍵；及ze·表示其中〇：-位置之碳原子經氟原子取代 之烷屬磺酸陰離子。 8.如申請專利範圍第2項之正型光敏劑組成物，其中具有 內酯結構之重複單位由以下式（IV)表示： J^1a ch2-c
其中Ru表示氫原子或甲基；Wi表示單鍵、伸烷基、醚 基、硫醚基、羰基、酯基、或其二或更多種之組合； Ral、Rbl、Rel、Rdl、與Rel可爲相同或不同’各獨立地 表示氫原子或具有1至4個碳原子之烷基；及111與η可 爲相同或不同，各獨立地表示〇至3之整數，其條件爲 m與η之總和爲2至6。 9 .如申g靑專利範圍第1項之正型光敏劑組成物，其中成分 一 6 — 1225186 更正本 六、申請專利範圍 (B)之樹脂更含具有以下式（V-1)至（V·4)任何之一表示之 基之重複單位：
其中Rlb、R2b、R3b、R4b、與Rsb可爲相同或不同，各 獨立地表示氫原子、可具有取代基之烷基、可具有取代 基之環烷基、或可具有取代基之烯基，或Rlb、R2b、 R3b、R4b、與Rsb之二可彼此組合形成環。 1 0 ·如申請專利範圍第1項之正型光敏劑組成物，其中成 分（B)之樹脂更含具有以下式（VI)表示之基之重複單位：
其中A6表示單鍵、伸院基、環伸烷基、醚基、硫醚基 、羰基、酯基、或其二或更多種之組合；R6a表示氫原 1225186 更正本 六、申請專利範圍 子、具有1至4個碳原子之烷基、氰基、或鹵素原子。 11.如申請專利範圍第1項之正型光敏劑組成物，其中成 分（B)之樹脂更含具有以下式（VII)表示之基之重複單位
其中Rk、R3e與R4C可爲相同或不同，各表示氫原子或 經基’其條件爲R2e、R3c與R4c至少之一表示經基。 12.如申請專利範圍第1項之正型光敏劑組成物，其中成 分（B)之樹脂更含具有以下式（viii)表示之基之重複單位 一CH-CH —
(VIII) 其中Z2表示-〇·或_N(R41)_ ; R41表示氫原子、羥基、烷 基、齒院基、或-0-S02-R42 ;及R42表示烷基、鹵烷基 、環烷基、或莰醇殘基。 13.如申請專利範圍第1項之正型光敏劑組成物，其更包 括鹼性化合物。 1 4 ·如申請專利範圍第13項之正型光敏劑組成物，其中鹼 性化合物爲具有以下式（Α)至（Ε)任何之一表示之結構 ~ 8 - 1225186 六、申請專利範圍 之化合物： Γ' R250—N——Κ25έ (A) 個碳 R2s〇 其中R25Q、R251與R252可爲相同或不同，各獨立地 氨原子 '具有1至6個碳原子之院基、具有1运 原子之胺基烷基、具有1至6個碳原子之羥棱基 有6至2〇個碳原子之經取代或未取代芳烷基 與R2M可彼此組合形成環， •N—C=N— (B) ：C—N=C — (C) ;C—N — (D) R254 R255 ：253 —C—N —C-—R256 (E) 其中R2 53、R254、R2 5 5與R256可爲相同或不 一 j ’各獨立 地表示具有1至6個碳原子之烷基。 1 5.如申請專利範圍第1項之正型光敏劑組成物，其更包 括以氟爲主及/或以矽爲主界面活性劑。 一9一
TW091113605A 2001-06-21 2002-06-21 Positive photosensitive composition TWI225186B (en)

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JP2001188499A JP3912767B2 (ja) 2001-06-21 2001-06-21 ポジ型感光性組成物

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US11127592B2 (en) 2018-05-31 2021-09-21 Taiwan Semiconductor Manufacturing Co., Ltd. Photosensitive groups in resist layer
TWI749563B (zh) * 2019-05-27 2021-12-11 日商信越化學工業股份有限公司 分子光阻組成物及使用其之圖案形成方法

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JP5205027B2 (ja) * 2007-07-18 2013-06-05 東京応化工業株式会社 化合物の製造方法
KR20100126734A (ko) * 2008-03-12 2010-12-02 다이셀 가가꾸 고교 가부시끼가이샤 락톤 골격을 포함하는 단량체, 고분자 화합물 및 포토레지스트 조성물
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