JPWO2020196601A5 - - Google Patents

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JPWO2020196601A5
JPWO2020196601A5 JP2020517600A JP2020517600A JPWO2020196601A5 JP WO2020196601 A5 JPWO2020196601 A5 JP WO2020196601A5 JP 2020517600 A JP2020517600 A JP 2020517600A JP 2020517600 A JP2020517600 A JP 2020517600A JP WO2020196601 A5 JPWO2020196601 A5 JP WO2020196601A5
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generator
photo
resin composition
photosensitive resin
positive photosensitive
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JP7484710B2 (en
JPWO2020196601A1 (en
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下記一般式(1)および(2)で表される構造を有するポリシロキサン(A1)、ナフトキノンジアジド化合物(B)、ならびに200~360nmに極大吸収波長を有する光ラジカル発生剤(C1)および/または光酸発生剤(C1’)を含有することを特徴とする、ポジ型感光性樹脂組成物。
Figure 2020196601000001
(R1は水素原子もしくはメチル基、R2およびR3は単結合もしくは置換または無置換の炭素数1~8の炭化水素基。星印はケイ素原子に直結する。)
Polysiloxane (A1) having a structure represented by the following general formulas (1) and (2), a naphthoquinone diazide compound (B), and a photoradical generator (C1) having a maximum absorption wavelength of 200 to 360 nm and/or A positive photosensitive resin composition comprising a photoacid generator (C1′).
Figure 2020196601000001
(R 1 is a hydrogen atom or a methyl group, R 2 and R 3 are a single bond or a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms. The asterisk is directly linked to a silicon atom.)
前記光ラジカル発生剤(C1)もしくは光酸発生剤(C1’)、または前記光ラジカル発生剤(C2)もしくは光酸発生剤(C2’)の200~360nmでの吸光係数の最大値が、360nm~450nmでの吸光係数の最大値の4倍以上である、請求項1に記載のポジ型感光性樹脂組成物。 The maximum absorption coefficient at 200 to 360 nm of the photo-radical generator (C1) or photo-acid generator (C1′), or the photo-radical generator (C2) or photo-acid generator (C2′) is 360 nm. 2. The positive photosensitive resin composition according to claim 1 , which is 4 times or more the maximum absorption coefficient at ~450 nm. 前記光ラジカル発生剤(C1)もしくは光酸発生剤(C1’)、または前記光ラジカル発生剤(C2)もしくは光酸発生剤(C2’)の300nm~360nmでの吸光係数の最大値が、3000mL/g・cm以上である請求項1または2に記載のポジ型感光性樹脂組成物。 The maximum absorption coefficient at 300 nm to 360 nm of the photo-radical generator (C1) or photo-acid generator (C1′), or the photo-radical generator (C2) or photo-acid generator (C2′) is 3000 mL. /g·cm or more, the positive photosensitive resin composition according to claim 1 or 2 . 前記光ラジカル発生剤(C1)もしくは光酸発生剤(C1’)、または前記光ラジカル発生剤(C2)もしくは光酸発生剤(C2’)の360nm~450nmでの吸光係数の最大値が、500mL/g・cm未満である、請求項1~のいずれかに記載のポジ型感光性樹脂組成物。 The maximum value of the absorption coefficient at 360 nm to 450 nm of the photo-radical generator (C1) or photo-acid generator (C1′), or the photo-radical generator (C2) or photo-acid generator (C2′) is 500 mL. /g·cm, the positive photosensitive resin composition according to any one of claims 1 to 3 . 前記ポリシロキサン(A1)または前記ポリシロキサン(A2)が、さらに下記一般式(3)で表される構造を有する、請求項1~4のいずれかに記載のポジ型感光性樹脂組成物。
Figure 2020196601000002
(Rは単結合もしくは置換または無置換の2価の炭素数1~6の炭化水素基であって置換基を有していてもよい。)
The positive photosensitive resin composition according to any one of claims 1 to 4 , wherein said polysiloxane (A1) or said polysiloxane (A2) further has a structure represented by the following general formula (3).
Figure 2020196601000002
(R 4 is a single bond or a substituted or unsubstituted divalent hydrocarbon group having 1 to 6 carbon atoms, which may have a substituent.)
前記ポリシロキサン(A1)または前記ポリシロキサン(A2)がカルボキシル基またはカルボン酸無水物を有する有機基を有する請求項1~のいずれかに記載のポジ型感光性樹脂組成物。 The positive photosensitive resin composition according to any one of claims 1 to 5 , wherein the polysiloxane (A1) or the polysiloxane (A2) has an organic group having a carboxyl group or a carboxylic anhydride. 前記一般式(1)および(2)で表される構造の総量が、前記ポリシロキサン(A1)または前記ポリシロキサン(A2)中のケイ素原子の総量に対して30~60mоl%であることを特徴とする、請求項1~6のいずれかに記載のポジ型感光性樹脂組成物。 The total amount of the structures represented by the general formulas (1) and (2) is 30 to 60 mol% with respect to the total amount of silicon atoms in the polysiloxane (A1) or the polysiloxane (A2). The positive photosensitive resin composition according to any one of claims 1 to 6 , wherein さらに酸無水物基を有する化合物(D)を含有する、請求項1~のいずれかに記載のポジ型感光性樹脂組成物。 The positive photosensitive resin composition according to any one of claims 1 to 7 , further comprising a compound (D) having an acid anhydride group. さらに不飽和二重結合を二つ以上有する多官能モノマー(E)を含有する、請求項1~のいずれかに記載のポジ型感光性樹脂組成物。 The positive photosensitive resin composition according to any one of claims 1 to 8 , further comprising a polyfunctional monomer (E) having two or more unsaturated double bonds. 前記光ラジカル発生剤(C1)もしくは光酸発生剤(C1’)または前記光ラジカル発生剤(C2)もしくは光酸発生剤(C2’)が300nm~360nmに極大吸収波長を有する、請求項1~のいずれかに記載のポジ型感光性樹脂組成物。 Claims 1 to 3, wherein the photoradical generator (C1) or photoacid generator (C1') or the photoradical generator (C2) or photoacid generator (C2') has a maximum absorption wavelength of 300 nm to 360 nm. 9. The positive photosensitive resin composition according to any one of 9 . 以下の工程をこの順に行う硬化膜の製造方法。
(i)請求項1~10のいずれかに記載のポジ型感光性樹脂組成物を基板上に塗布して塗膜を形成する工程。
(ii)該塗膜を、365nm、405nm、436nmのうちいずれかの光の露光量が計10mJ/m以上となり、波長350nm未満の光の露光量が計1mJ/m以下となるようにパターン露光した後、現像液で現像することにより、塗膜の露光部分を除去する工程。
(iii)前記現像後、残った塗膜を前記光ラジカル発生剤(C1)および/または酸発生剤(C1’)、または、前記光ラジカル発生剤(C2)および/または酸発生剤(C2’)の、波長200~350nmでの露光量が、計10mJ/m以上となるよう、露光する工程。
(iv)前記露光後の塗膜を加熱する工程。
A method for producing a cured film in which the following steps are performed in this order.
(i) A step of applying the positive photosensitive resin composition according to any one of claims 1 to 10 onto a substrate to form a coating film.
(ii) The coating film is coated so that the total exposure to light of 365 nm, 405 nm, or 436 nm is 10 mJ/ m2 or more, and the total exposure to light with a wavelength of less than 350 nm is 1 mJ/m2 or less. A step of removing the exposed portion of the coating film by developing with a developer after pattern exposure.
(iii) After the development, the remaining coating film is treated with the photoradical generator (C1) and/or the acid generator (C1′), or the photoradical generator (C2) and/or the acid generator (C2′). ), the step of exposing so that the total exposure amount at a wavelength of 200 to 350 nm is 10 mJ/m 2 or more.
(iv) a step of heating the coating film after the exposure;
請求項1~10のいずれかに記載のポジ型感光性樹脂組成物の硬化膜。 A cured film of the positive photosensitive resin composition according to any one of claims 1 to 10 . 請求項12に記載の硬化膜を具備する光学デバイスもしくは電子材料。 An optical device or electronic material comprising the cured film according to claim 12 . 請求項12に記載の硬化膜からなる、光導波路、平坦化膜、保護膜、および層間絶縁膜からなる群より選ばれる少なくとも1つを含む、光学デバイスもしくは電子材料。 An optical device or electronic material comprising at least one selected from the group consisting of an optical waveguide, a planarizing film, a protective film, and an interlayer insulating film, comprising the cured film according to claim 12 .
JP2020517600A 2019-03-26 2020-03-25 Positive-type photosensitive resin composition, cured film thereof, and optical device having the same Active JP7484710B2 (en)

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JP2019058133 2019-03-26
JP2019058133 2019-03-26
PCT/JP2020/013260 WO2020196601A1 (en) 2019-03-26 2020-03-25 Positive-type photosensitive resin composition, cured film thereof, and optical device including same

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JP5310051B2 (en) 2009-02-12 2013-10-09 Jsr株式会社 Radiation-sensitive composition, microlens and method for forming the same
JP5397152B2 (en) 2009-10-22 2014-01-22 Jsr株式会社 Positive radiation-sensitive composition, interlayer insulating film and method for forming the same
JP5917150B2 (en) * 2009-11-27 2016-05-11 Jsr株式会社 Positive radiation-sensitive composition, cured film and method for forming the same
JP5818022B2 (en) 2010-05-13 2015-11-18 日産化学工業株式会社 Photosensitive resin composition and display device
EP2799928B1 (en) * 2011-12-26 2019-05-22 Toray Industries, Inc. Photosensitive resin composition and process for producing semiconductor element
JP2017173741A (en) * 2016-03-25 2017-09-28 アーゼッド・エレクトロニック・マテリアルズ(ルクセンブルグ)ソシエテ・ア・レスポンサビリテ・リミテ Photosensitive siloxane composition
CN109071742B (en) * 2016-04-25 2021-07-09 东丽株式会社 Resin composition, cured film thereof, method for producing same, and solid-state imaging device

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