JP2023159486A - Photosensitive composition, optical filter, image display device, and solid-state imaging element - Google Patents
Photosensitive composition, optical filter, image display device, and solid-state imaging element Download PDFInfo
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- JP2023159486A JP2023159486A JP2022069156A JP2022069156A JP2023159486A JP 2023159486 A JP2023159486 A JP 2023159486A JP 2022069156 A JP2022069156 A JP 2022069156A JP 2022069156 A JP2022069156 A JP 2022069156A JP 2023159486 A JP2023159486 A JP 2023159486A
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- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- UHGYPKHARWLOQB-UHFFFAOYSA-N trihydroxy-(13-phenyltridecyl)-tridecyl-lambda5-phosphane Chemical compound CCCCCCCCCCCCCP(O)(O)(O)CCCCCCCCCCCCCC1=CC=CC=C1 UHGYPKHARWLOQB-UHFFFAOYSA-N 0.000 description 1
- QHCNTMCHBZHBDY-UHFFFAOYSA-N trihydroxy-(6-methylheptyl)-phenyl-lambda5-phosphane Chemical compound CC(C)CCCCCP(O)(O)(O)C1=CC=CC=C1 QHCNTMCHBZHBDY-UHFFFAOYSA-N 0.000 description 1
- SFESXIFARCRODZ-UHFFFAOYSA-N trihydroxy-(8-methylnonyl)-phenyl-$l^{5}-phosphane Chemical compound CC(C)CCCCCCCP(O)(O)(O)C1=CC=CC=C1 SFESXIFARCRODZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Power Engineering (AREA)
- Structural Engineering (AREA)
- Optics & Photonics (AREA)
- Electromagnetism (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Architecture (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
Description
本発明は、感光性組成物、それを用いた光学フィルタに関する。 The present invention relates to a photosensitive composition and an optical filter using the same.
画像表示装置や固体撮像素子等に使用する光学フィルタの1種カラーフィルタは、ガラス基板等の透明な基板上に、色相が異なる2種以上の微細な帯状のフィルタセグメントを互いに平行に(ストライプ状に)若しくは交差するように配置する。又は、色相が異なる2種以上の微細なフィルタセグメントを縦方向及び横方向の各々において順番に配列するように配置する。このフィルタセグメントは、数ミクロン~数100ミクロンの小さな寸法を有しており、色相毎に所定の配列で整然と配置されている。 A color filter is a type of optical filter used in image display devices, solid-state imaging devices, etc. Two or more types of fine band-shaped filter segments of different hues are arranged parallel to each other (in a stripe pattern) on a transparent substrate such as a glass substrate. ) or intersect with each other. Alternatively, two or more types of fine filter segments having different hues are arranged in order in each of the vertical and horizontal directions. These filter segments have small dimensions ranging from several microns to several hundred microns, and are neatly arranged in a predetermined arrangement for each hue.
現在、カラーフィルタの製造方法としては、感光性組成物を、ガラス等の透明基板に塗布し、乾燥によってこの塗膜から溶剤を除去する工程、この塗膜を、所望するパターン形状を有するフォトマスクを介して放射線を照射・硬化(以下、露光という)工程、次いで、この塗膜の未露光部を洗浄・除去(以下、現像という)する工程、その後、必要に応じて硬化膜を十分に硬化させるために加熱処理(以下、ポストベークという)工程により1色目のフィルタセグメントパターンを得る。そして、これと同様の操作を行うことにより他の色のフィルタセグメントパターンを形成し、カラーフィルタを完成する。 Currently, the manufacturing method for color filters includes a process of applying a photosensitive composition to a transparent substrate such as glass and removing the solvent from this coating film by drying, and applying this coating film to a photomask having a desired pattern shape. irradiation and curing process (hereinafter referred to as exposure) with radiation through the coating, then a process of cleaning and removing the unexposed areas of this coating film (hereinafter referred to as development), and then, if necessary, sufficiently curing the cured film. In order to achieve this, a filter segment pattern of the first color is obtained through a heat treatment (hereinafter referred to as post-bake) step. Then, by performing a similar operation to this, filter segment patterns of other colors are formed to complete a color filter.
上記現像工程は、現像液としてアルカリ性の現像液を用いて、未露光部分を洗浄・除去する。その際に、露光した部分が欠けたり、剥がれたりしてパターン形状に欠陥が発生するという問題があった。また、アルカリ性の現像液に塗膜が曝された場合、塗膜が変色する現象(以下、水しみという)が発生する問題もあった。そのため、現像工程においてパターン形状の不良と水しみが発生しない感光性組成物が求められている。さらに、現像工程やポストベーク工程の際に、未反応物等が溶出や気化することで塗膜の膜厚が変化する(以下、残膜率という)問題もあった。 In the development step, an alkaline developer is used as a developer to wash and remove the unexposed areas. At that time, there was a problem in that the exposed portions were chipped or peeled off, resulting in defects in the pattern shape. Further, when the coating film is exposed to an alkaline developer, there is a problem in that the coating film changes color (hereinafter referred to as water stain). Therefore, there is a need for a photosensitive composition that does not cause defective pattern shapes or water stains during the development process. Furthermore, there was also the problem that the film thickness of the coating film changes (hereinafter referred to as residual film ratio) due to elution or vaporization of unreacted substances during the development process and post-baking process.
水しみの改善の取り組みとして、特許文献1には、特定構造のフッ素系界面活性剤を含むレジスト組成物が開示されている。また、現像時のパターン欠け改善の取り組みとして、特許文献2には、アルキレンオキサイド構造を有する重合性化合物を含む着色組成物が開示されている。また、高濃度の着色剤を含む場合のパターン形成性の改善の取り組みとして、特許文献3には、多官能チオール化合物およびアセトフェノン化合物を含む着色感光性樹脂組成物が開示されている。 As an effort to improve water stains, Patent Document 1 discloses a resist composition containing a fluorine-based surfactant with a specific structure. Further, as an effort to improve pattern chipping during development, Patent Document 2 discloses a colored composition containing a polymerizable compound having an alkylene oxide structure. Furthermore, as an effort to improve pattern formation when a high concentration of colorant is included, Patent Document 3 discloses a colored photosensitive resin composition containing a polyfunctional thiol compound and an acetophenone compound.
しかし、特許文献1~3のいずれの組成物も水しみ、パターン形状を満足できるものではなかった。また、残膜率に関しては考慮されておらず、満足できるものではなかった。 However, none of the compositions disclosed in Patent Documents 1 to 3 were satisfactory in terms of water stains and pattern shapes. Further, the remaining film rate was not taken into consideration, and the results were not satisfactory.
本発明は、現像後の被膜の水しみを抑制し、残膜率が良好で、優れたパターンを形成できる感光性組成物の提供を目的する。 The present invention aims to provide a photosensitive composition that can suppress water stains on a film after development, has a good residual film rate, and can form an excellent pattern.
本発明は、アルカリ可溶性樹脂(A)、重合性化合物(B)、及び光重合開始剤(C)を含む感光性組成物であって、
前記光重合開始剤(C)が、下記一般式(1)で表されるオキシム系光重合開始剤(C1)、及びオキシム系光重合開始剤(C1)以外のオキシム系光重合開始剤(C2)を含む感光性組成物に関する。
一般式(1)
The photopolymerization initiator (C) is an oxime photopolymerization initiator (C1) represented by the following general formula (1), and an oxime photopolymerization initiator (C2) other than the oxime photopolymerization initiator (C1). ).
General formula (1)
(一般式(1)中、R1は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R2は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原
子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R3は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R4は、1価の置換基を表す。nは、0~3の整数を表す。)
(In the general formula (1), R 1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or Represents 2 to 20 heterocyclic groups.
R 2 represents an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
R 3 represents an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
R 4 represents a monovalent substituent. n represents an integer from 0 to 3. )
上記の本発明によれば、現像後の被膜の水しみを抑制し、残膜率が良好で、優れたパターンを形成できる感光性組成物を提供できる。また、本発明は、光学フィルタ、画像表示装置、及び固体撮像素子を提供できる。 According to the present invention, it is possible to provide a photosensitive composition that suppresses water stains on a film after development, has a good residual film rate, and can form an excellent pattern. Further, the present invention can provide an optical filter, an image display device, and a solid-state image sensor.
以下に、本発明の感光性組成物を実施するための形態について詳細に説明する。なお、本発明は、以下の実施形態に制限されるものではなく、課題を解決可能な範囲内で変形して実施できる。 Below, modes for carrying out the photosensitive composition of the present invention will be explained in detail. Note that the present invention is not limited to the following embodiments, and can be modified and implemented within the scope that can solve the problem.
本発明において、「(メタ)アクリロイル」、「(メタ)アクリル」、「(メタ)アクリル酸」、「(メタ)アクリレート」、又は「(メタ)アクリルアミド」とは、特に説明がない限り、それぞれ、「アクリロイル及び/又はメタアクリロイル」、「アクリル及び/又はメタアクリル」、「アクリル酸及び/又はメタアクリル酸」、「アクリレート及び/又はメタクリレート」、又は「アクリルアミド及び/又はメタアクリルアミド」を意味する。また、「C.I.」は、カラーインデックス(C.I.;The Society of Dyers and Colourists 発行)を意味する。重合性不飽和基は、エチレン性不飽和二重結合である。
また、本発明における化合物の分子量に関しては、分子量が特定できる低分子化合物については、計算により算出した値(式量)、若しくはESi-MS(エレクトロスプレーイオン化質量分析法)により測定した分子量であり、分子量の分布を持つ化合物については、テトラヒドロフランを溶剤とした場合のゲルパーミエーションクロマトグラフィーで測定されるポリスチレン換算の重量平均分子量である。重合性化合物(B)は、硬化によ
り被膜を形成する化合物である。単量体は、重合により樹脂を形成する化合物である。単量体は、未反応状態であり、単量体単位は、単量体を重合後に樹脂を形成している状態である。
In the present invention, "(meth)acryloyl", "(meth)acrylic", "(meth)acrylic acid", "(meth)acrylate", or "(meth)acrylamide" are respectively used unless otherwise specified. , means "acryloyl and/or methacryloyl", "acrylic and/or methacrylic", "acrylic acid and/or methacrylic acid", "acrylate and/or methacrylate", or "acrylamide and/or methacrylamide" . Further, "C.I." means Color Index (C.I.; published by The Society of Dyers and Colorists). The polymerizable unsaturated group is an ethylenically unsaturated double bond.
In addition, regarding the molecular weight of the compound in the present invention, for low-molecular compounds whose molecular weight can be specified, the value calculated by calculation (formula weight) or the molecular weight measured by ESi-MS (electrospray ionization mass spectrometry), For compounds with a molecular weight distribution, this is the weight average molecular weight in terms of polystyrene measured by gel permeation chromatography using tetrahydrofuran as a solvent. The polymerizable compound (B) is a compound that forms a film upon curing. Monomers are compounds that form resins upon polymerization. The monomers are in an unreacted state, and the monomer units are in a state where a resin is formed after the monomers are polymerized.
<感光性組成物>
本発明の一実施形態は、感光性組成物に関する。本発明の感光性組成物は、アルカリ可溶性樹脂(A)、重合性化合物(B)、及び光重合開始剤(C)を含む感光性組成物であって、
前記光重合開始剤(C)が、下記一般式(1)で表されるオキシム系光重合開始剤(C1)、及びオキシム系光重合開始剤(C1)以外のオキシム系光重合開始剤(C2)を含む。本発明の感光性組成物は、パターン形成可能であり、被膜を形成し光硬化して使用することが好ましい。前記被膜は、例えば、画像表示装置、固体撮像素子の光学デバイスに組み込む用途が好ましい。
一般式(1)
One embodiment of the present invention relates to a photosensitive composition. The photosensitive composition of the present invention is a photosensitive composition containing an alkali-soluble resin (A), a polymerizable compound (B), and a photoinitiator (C),
The photopolymerization initiator (C) is an oxime photopolymerization initiator (C1) represented by the following general formula (1), and an oxime photopolymerization initiator (C2) other than the oxime photopolymerization initiator (C1). )including. The photosensitive composition of the present invention can be patterned, and is preferably used after forming a film and photocuring. The coating is preferably used to be incorporated into an optical device such as an image display device or a solid-state image sensor, for example.
General formula (1)
一般式(1)中、R1は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R2は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原
子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R3は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R4は、1価の置換基を表す。nは、0~3の整数を表す。
In the general formula (1), R 1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or 2 carbon atoms. ~20 heterocyclic groups.
R 2 represents an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
R 3 represents an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
R 4 represents a monovalent substituent. n represents an integer from 0 to 3.
以下、一実施形態の感光性組成物に含まれるか、又は含まれ得る成分を詳細に説明する。 Components that are or can be included in the photosensitive composition of one embodiment will be described in detail below.
[光重合開始剤(C)]
本発明の感光性組成物は、光重合開始剤(C)として、一般式(1)で表されるオキシム系光重合開始剤(C1)、及びオキシム系光重合開始剤(C1)以外のオキシム系光重合開始剤(C2)を含む。
(C1)と異なる構造の(C2)を併用することで、有効に利用できる光の波長領域が広がり感度が向上することで、被膜が強靭となり水しみ、残膜率が良好となると考えられる。
[Photopolymerization initiator (C)]
The photosensitive composition of the present invention uses an oxime-based photoinitiator (C1) represented by general formula (1) as a photoinitiator (C), and an oxime-based photoinitiator other than the oxime-based photoinitiator (C1). Contains a photopolymerization initiator (C2).
It is thought that by using (C1) and (C2) with a different structure, the wavelength range of light that can be used effectively is expanded and the sensitivity is improved, making the film tougher and reducing water stains and film retention.
(オキシム系光重合開始剤(C1))
オキシム系光重合開始剤(C1)は、下記一般式(1)で表される化合物である。
一般式(1)
The oxime photopolymerization initiator (C1) is a compound represented by the following general formula (1).
General formula (1)
一般式(1)中、R1は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R2は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原
子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R3は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R4は、任意の1価の置換基を表す。nは、0~3の整数を表す。
In the general formula (1), R 1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or 2 carbon atoms. ~20 heterocyclic groups.
R 2 represents an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
R 3 represents an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
R 4 represents any monovalent substituent. n represents an integer from 0 to 3.
一般式(1)中、R1は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
炭素原子数1~20のアルキル基としては、直鎖状でも、分岐状でも、環状でも、それらが結合したものであってもよく、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、t-ブチル基、ペンチル基、イソペンチル基、ヘキシル基、ヘプチル基、オクチル基、イソオクチル基、2-エチルヘキシル基、ノニル基、イソノニル基、デシル基、イソデシル基、ウンデシル基、ドデシル基、ヘキサデシル基、シクロペンチル基、シクロペンチルメチル基、シクロヘキシル基、シクロヘキシルメチル基、シクロヘキシルメチル基等が挙げられる。
炭素原子数6~30のアリール基としては、例えば、フェニル基、トリル基、キシリル基、エチルフェニル基、ナフチル基、アンスリル基等が挙げられる。
炭素原子数7~30のアリールアルキル基としては、例えば、ベンジル基、α―メチルベンジル、α,α―ジメチルベンジル基、フェニルエチル基等が挙げられる。
炭素原子数2~20の複素環基としては、例えば、ピリジル基、ピリミジル基、フリル基、テトラヒドロフリル基、ジオキソラニル基、イミダゾリジル基、オキサゾリジル基、ピペリジル基、モルホリニル基等が挙げられる。
上記の中でも、反応性の観点から、メチル基、エチル基、又はフェニル基が好ましく、メチル基、又はエチル基がより好ましい。
In the general formula (1), R 1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or 2 carbon atoms. ~20 heterocyclic groups.
The alkyl group having 1 to 20 carbon atoms may be linear, branched, cyclic, or a combination thereof; for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group. group, isobutyl group, t-butyl group, pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group , hexadecyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, cyclohexylmethyl group, and the like.
Examples of the aryl group having 6 to 30 carbon atoms include phenyl group, tolyl group, xylyl group, ethylphenyl group, naphthyl group, and anthryl group.
Examples of the arylalkyl group having 7 to 30 carbon atoms include benzyl group, α-methylbenzyl group, α,α-dimethylbenzyl group, and phenylethyl group.
Examples of the heterocyclic group having 2 to 20 carbon atoms include a pyridyl group, a pyrimidyl group, a furyl group, a tetrahydrofuryl group, a dioxolanyl group, an imidazolidyl group, an oxazolidyl group, a piperidyl group, a morpholinyl group, and the like.
Among the above, from the viewpoint of reactivity, a methyl group, an ethyl group, or a phenyl group is preferable, and a methyl group or an ethyl group is more preferable.
一般式(1)中、R2は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
炭素原子数3~20のアルキル基としては、直鎖状でも、分岐状でも、環状でも、それらが結合したものであってもよく、例えば、プロピル基、イソプロピル基、ブチル基、イソブチル基、t-ブチル基、ペンチル基、イソペンチル基、ヘキシル基、ヘプチル基、オクチル基、イソオクチル基、2-エチルヘキシル基、ノニル基、イソノニル基、デシル基、イソデシル基、ウンデシル基、ドデシル基、ヘキサデシル基、シクロペンチル基、シクロペンチルメチル基、シクロヘキシル基、シクロヘキシルメチル基、シクロヘキシルメチル基等が挙げられる。
炭素原子数6~30のアリール基としては、例えば、フェニル基、トリル基、キシリル基
、エチルフェニル基、ナフチル基、アンスリル基等が挙げられる。
炭素原子数7~30のアリールアルキル基としては、例えば、ベンジル基、α―メチルベンジル、α,α―ジメチルベンジル基、フェニルエチル基等が挙げられる。
炭素原子数2~20の複素環基としては、例えば、ピリジル基、ピリミジル基、フリル基、テトラヒドロフリル基、ジオキソラニル基、イミダゾリジル基、オキサゾリジル基、ピペリジル基、モルホリニル基等が挙げられる。
上記の中でも、パターン形状の観点から、炭素原子数3~20のアルキル基が好ましく、炭素原子数3~8のアルキル基がより好ましく、ペンチル基がさらに好ましい。
In the general formula (1), R 2 is an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an arylalkyl group having 2 to 20 carbon atoms. Represents a heterocyclic group.
The alkyl group having 3 to 20 carbon atoms may be linear, branched, cyclic, or a combination thereof; for example, propyl group, isopropyl group, butyl group, isobutyl group, t -Butyl group, pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, hexadecyl group, cyclopentyl group , cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, cyclohexylmethyl group, and the like.
Examples of the aryl group having 6 to 30 carbon atoms include phenyl group, tolyl group, xylyl group, ethylphenyl group, naphthyl group, and anthryl group.
Examples of the arylalkyl group having 7 to 30 carbon atoms include benzyl group, α-methylbenzyl group, α,α-dimethylbenzyl group, and phenylethyl group.
Examples of the heterocyclic group having 2 to 20 carbon atoms include a pyridyl group, a pyrimidyl group, a furyl group, a tetrahydrofuryl group, a dioxolanyl group, an imidazolidyl group, an oxazolidyl group, a piperidyl group, a morpholinyl group, and the like.
Among the above, from the viewpoint of pattern shape, alkyl groups having 3 to 20 carbon atoms are preferred, alkyl groups having 3 to 8 carbon atoms are more preferred, and pentyl groups are even more preferred.
一般式(1)中、R3は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
炭素原子数3~20のアルキル基としては、直鎖状でも、分岐状でも、環状でも、それらが結合したものであってもよく、例えば、プロピル基、イソプロピル基、ブチル基、イソブチル基、t-ブチル基、ペンチル基、イソペンチル基、ヘキシル基、ヘプチル基、オクチル基、イソオクチル基、2-エチルヘキシル基、ノニル基、イソノニル基、デシル基、イソデシル基、ウンデシル基、ドデシル基、ヘキサデシル基、シクロペンチル基、シクロペンチルメチル基、シクロヘキシル基、シクロヘキシルメチル基、シクロヘキシルメチル基等が挙げられる。
炭素原子数6~30のアリール基としては、例えば、フェニル基、トリル基、キシリル基、エチルフェニル基、ナフチル基、アンスリル基等が挙げられる。
炭素原子数7~30のアリールアルキル基としては、例えば、ベンジル基、α―メチルベンジル、α,α―ジメチルベンジル基、フェニルエチル基等が挙げられる。
炭素原子数2~20の複素環基としては、例えば、ピリジル基、ピリミジル基、フリル基、テトラヒドロフリル基、ジオキソラニル基、イミダゾリジル基、オキサゾリジル基、ピペリジル基、モルホリニル基等が挙げられる。
上記の中でも、水しみの抑制の観点から、炭素原子数3~15の分岐状のアルキル基が好ましく、炭素原子数5~12の分岐状のアルキル基がより好ましく、3-メチルブチル基、2-エチルヘキシル基がさらに好ましい。
In the general formula (1), R 3 is an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or an arylalkyl group having 2 to 20 carbon atoms. Represents a heterocyclic group.
The alkyl group having 3 to 20 carbon atoms may be linear, branched, cyclic, or a combination thereof; for example, propyl group, isopropyl group, butyl group, isobutyl group, t -Butyl group, pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, hexadecyl group, cyclopentyl group , cyclopentylmethyl group, cyclohexyl group, cyclohexylmethyl group, cyclohexylmethyl group, and the like.
Examples of the aryl group having 6 to 30 carbon atoms include phenyl group, tolyl group, xylyl group, ethylphenyl group, naphthyl group, and anthryl group.
Examples of the arylalkyl group having 7 to 30 carbon atoms include benzyl group, α-methylbenzyl group, α,α-dimethylbenzyl group, and phenylethyl group.
Examples of the heterocyclic group having 2 to 20 carbon atoms include a pyridyl group, a pyrimidyl group, a furyl group, a tetrahydrofuryl group, a dioxolanyl group, an imidazolidyl group, an oxazolidyl group, a piperidyl group, a morpholinyl group, and the like.
Among the above, from the viewpoint of suppressing water stains, a branched alkyl group having 3 to 15 carbon atoms is preferred, a branched alkyl group having 5 to 12 carbon atoms is more preferred, and a 3-methylbutyl group, a 2- Ethylhexyl group is more preferred.
一般式(1)中、R4は、任意の1価の置換基を表す。
1価の置換基としては、メチル基、エチル基等の炭素原子数1~20のアルキル基;メトキシ基、エトキシ基等の炭素原子数1~20のアルコキシ基;F、Cl、Br、i等のハロゲン原子;炭素原子数1~20のアシル基;炭素原子数1~20のアルキルエステル基;炭素原子数1~20のアルコキシカルボニル基;炭素原子数1~20のハロゲン化アルキル基、炭素原子数4~20の芳香族環基;アミノ基;炭素原子数1~20のアミノアルキル基;水酸基;ニトロ基;シアノ基;置換基を有してよいベンゾイル基;置換基を有してよいテノイル基等が挙げられる。ベンゾイル基、又はテノイル基が有してよい置換基としては、炭素原子数1~10のアルキル基、炭素原子数1~10のアルコキシ基、炭素原子数1~10のアルコキシカルボニル基等が挙げられ、1~3個の範囲で有してよい。
上記の中でも、反応性の観点から、置換基を有してよいベンゾイル基が好ましく、置換基がアルコキシカルボニル基であるベンゾイル基がより好ましい。
In general formula (1), R 4 represents any monovalent substituent.
Monovalent substituents include alkyl groups having 1 to 20 carbon atoms such as methyl and ethyl groups; alkoxy groups having 1 to 20 carbon atoms such as methoxy and ethoxy groups; F, Cl, Br, i, etc. halogen atom; acyl group having 1 to 20 carbon atoms; alkyl ester group having 1 to 20 carbon atoms; alkoxycarbonyl group having 1 to 20 carbon atoms; halogenated alkyl group having 1 to 20 carbon atoms, carbon atom Aromatic ring group having 4 to 20 atoms; amino group; aminoalkyl group having 1 to 20 carbon atoms; hydroxyl group; nitro group; cyano group; benzoyl group that may have a substituent; thenoyl group that may have a substituent Examples include groups. Examples of substituents that the benzoyl group or thenoyl group may have include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkoxycarbonyl group having 1 to 10 carbon atoms, etc. , in the range of 1 to 3.
Among the above, from the viewpoint of reactivity, a benzoyl group which may have a substituent is preferable, and a benzoyl group whose substituent is an alkoxycarbonyl group is more preferable.
一般式(1)中、nは、0~3の整数を表す。これらの中でも、ラジカル生成効率の観点から、0、又は1であることが好ましく、1であることがより好ましい。 In general formula (1), n represents an integer of 0 to 3. Among these, from the viewpoint of radical generation efficiency, it is preferably 0 or 1, and more preferably 1.
オキシム系光重合開始剤(C1)の製造方法は、公知の方法を用いることができる。例えば、国際公開第2008/078678号、国際公開第2014/050738号、特表2016-519675号公報等に記載の方法が挙げられる。 A known method can be used to produce the oxime photopolymerization initiator (C1). For example, methods described in International Publication No. 2008/078678, International Publication No. 2014/050738, Japanese Translation of PCT International Publication No. 2016-519675, etc. can be mentioned.
以下、一般式(1)で表される化合物の具体例を示す。なお、本発明はこれらに限定されない。 Specific examples of the compound represented by general formula (1) are shown below. Note that the present invention is not limited to these.
化学式(2)~(7)の化合物の中でも、水しみの抑制、パターン形状、及び残膜率の観点から、化学式(7)の化合物が好ましい。 Among the compounds of chemical formulas (2) to (7), the compound of chemical formula (7) is preferred from the viewpoint of water stain suppression, pattern shape, and film remaining rate.
オキシム系光重合開始剤(C1)は、単独または2種類以上を併用して使用できる。 The oxime photopolymerization initiator (C1) can be used alone or in combination of two or more types.
(オキシム系光重合開始剤(C2))
オキシム系光重合開始剤(C2)は、一般式(1)で表されるオキシム系光重合開始剤(C1)以外の光重合開始剤である。オキシム系光重合開始剤(C2)の市販品は、例えば、BASFジャパン社製のIRGACURE OXE-01,02,03,04、ADEKA社製のアデカアークルズN-1919,NCi-730,831,930、常州強力新材料社製のTRONLY TR-PBG-301,304,305,309,314,345,346,358,380,365,610,3054,3057、IGM Resins社製のOMNIRAD1312,1314,1316、サムヤンコーポレーション社製のSPI-02,03,04,05,06,07、ダイトーケミックス社製のDFI-020,306、EOX-01等が挙げられる。
(Oxime-based photopolymerization initiator (C2))
The oxime photopolymerization initiator (C2) is a photopolymerization initiator other than the oxime photopolymerization initiator (C1) represented by general formula (1). Commercial products of the oxime photopolymerization initiator (C2) include, for example, IRGACURE OXE-01, 02, 03, 04 manufactured by BASF Japan, and ADEKA Arkles N-1919, NCi-730, 831, 930 manufactured by ADEKA. , TRONLY TR-PBG-301, 304, 305, 309, 314, 345, 346, 358, 380, 365, 610, 3054, 3057 manufactured by Changzhou Strong New Materials, OMNIRAD1312, 1314, 1316 manufactured by IGM Resins, Examples include SPI-02, 03, 04, 05, 06, 07 manufactured by Samyang Corporation, and DFI-020, 306 and EOX-01 manufactured by Daito Chemix.
オキシム系光重合開始剤(C2)の具体例としては、例えば、以下のものが挙げられる。なお、本発明はこれらに限定されない。 Specific examples of the oxime photopolymerization initiator (C2) include the following. Note that the present invention is not limited to these.
化学式(12) 化学式(13)
化学式(8)~(16)の化合物の製造方法は、例えば、特表2004-534797号公報、特開2008-80068号公報、特表2012-526185号公報、国際公開第2015/036910号、国際公開第2015/152153号、特表2016-504270号公報、特表2017-512886号公報等に記載の方法が挙げられる。 Methods for producing compounds of chemical formulas (8) to (16) are described, for example, in Japanese Patent Publication No. 2004-534797, Japanese Patent Application Publication No. 2008-80068, Japanese Patent Application Publication No. 2012-526185, International Publication No. 2015/036910, International Publication No. 2015/036910, Examples include methods described in Publication No. 2015/152153, Japanese Translated Patent Application Publication No. 2016-504270, Japanese Patent Application Publication No. 2017-512886, and the like.
オキシム系光重合開始剤(C2)は、化学式(8)~(16)の化合物の中でも、水しみの抑制、パターン形状、及び残膜率の観点から、化学式(11)~(16)の化合物からなる群から選ばれる1種以上が好ましい。 Among the compounds of chemical formulas (8) to (16), the oxime photopolymerization initiator (C2) is preferably a compound of chemical formulas (11) to (16) from the viewpoint of water stain suppression, pattern shape, and film retention rate. One or more types selected from the group consisting of are preferred.
オキシム系光重合開始剤(C2)は、単独または2種類以上を併用して使用できる。 The oxime photopolymerization initiator (C2) can be used alone or in combination of two or more types.
オキシム系光重合開始剤(C1)とオキシム系光重合開始剤(C2)の質量比は、水しみの抑制、パターン形状、及び残膜率の観点から、90:10~10:90が好ましく、80:20~20:80がより好ましく、70:30~30:70がさらに好ましい。 The mass ratio of the oxime-based photopolymerization initiator (C1) and the oxime-based photopolymerization initiator (C2) is preferably 90:10 to 10:90 from the viewpoint of water stain suppression, pattern shape, and film remaining rate. The ratio is more preferably 80:20 to 20:80, and even more preferably 70:30 to 30:70.
オキシム系光重合開始剤(C1)とオキシム系光重合開始剤(C2)の合計含有量は、水しみの抑制、パターン形状、及び残膜率の観点から、光重合開始剤(C)100質量%中、50質量%以上であることが好ましく、80質量%以上であることがより好ましい。 The total content of the oxime-based photopolymerization initiator (C1) and the oxime-based photopolymerization initiator (C2) is 100 mass of the photopolymerization initiator (C) from the viewpoint of water stain suppression, pattern shape, and film remaining rate. %, preferably 50% by mass or more, more preferably 80% by mass or more.
((C1)及び(C2)以外の光重合開始剤(C3))
本発明の感光性組成物は、オキシム系光重合開始剤(C1)及びオキシム系光重合開始剤(C2)以外の光重合開始剤(C3)(以下、その他光重合開始剤(C3)ともいう)を含むことができる。
(Photopolymerization initiator (C3) other than (C1) and (C2))
The photosensitive composition of the present invention includes a photopolymerization initiator (C3) other than the oxime photopolymerization initiator (C1) and the oxime photopolymerization initiator (C2) (hereinafter also referred to as other photopolymerization initiator (C3)). ) can be included.
その他光重合開始剤(C3)は、光により重合性化合物(B)の重合を開始可能な化合物であれば、特に制限はなく、公知の光重合開始剤できる。例えば、4-フェノキシジクロロアセトフェノン、4-t-ブチル-ジクロロアセトフェノン、ジエトキシアセトフェノン、1-(4-イソプロピルフェニル)-2-ヒドロキシ-2-メチルプロパン-1-オン、1-ヒドロキシシクロヘキシルフェニルケトン、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン、2-(ジメチルアミノ)-1-[4-(4-モルホリノ)フェニル]-2-(フェニルメチル)-1-ブタノン、又は2-(ジメチルアミノ)-2-[(4-メチルフェニル)メチル]-1-[4-(4-モルホリニル)フェニル]-1-ブタノン等のアセトフェノン系化合物;
2,4,6-トリクロロ-s-トリアジン、2-フェニル-4,6-ビス(トリクロロメチル)-s-トリアジン、2-(p-メトキシフェニル)-4,6-ビス(トリクロロメチル)-s-トリアジン、2-(p-トリル)-4,6-ビス(トリクロロメチル)-s-トリアジン、2-ピペロニル-4,6-ビス(トリクロロメチル)-s-トリアジン、2,4-ビス(トリクロロメチル)-6-スチリル-s-トリアジン、2-(ナフト-1-イル)-4,6-ビス(トリクロロメチル)-s-トリアジン、2-(4-メトキシ-ナフト-1-イル)-4,6-ビス(トリクロロメチル)-s-トリアジン、2,4-トリクロロメチル-(ピペロニル)-6-トリアジン、又は2,4-トリクロロメチル-(4’-メトキシスチリル)-6-トリアジン等のトリアジン系化合物;
ビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキサイド、又はジフェニル-2,4,6-トリメチルベンゾイルホスフィンオキサイド等のアシルホスフィン系化合物;
9,10-フェナンスレンキノン、カンファーキノン、エチルアントラキノン等のキノン系化合物;ボレート系化合物;カルバゾール系化合物;イミダゾール系化合物;あるいは、チタノセン系化合物等が挙げられる。
Other photopolymerization initiators (C3) are not particularly limited as long as they are compounds that can initiate polymerization of the polymerizable compound (B) by light, and any known photopolymerization initiators may be used. For example, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-Methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-(dimethylamino)-1-[4-(4-morpholino)phenyl]-2-(phenylmethyl )-1-butanone, or acetophenone compounds such as 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone;
2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s -triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-triazine methyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphth-1-yl)-4 , 6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine, or 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine. system compound;
Acyl phosphine compounds such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide or diphenyl-2,4,6-trimethylbenzoylphosphine oxide;
Examples include quinone compounds such as 9,10-phenanthrenequinone, camphorquinone, and ethyl anthraquinone; borate compounds; carbazole compounds; imidazole compounds; and titanocene compounds.
その他光重合開始剤(C3)は、単独または2種類以上を併用して使用できる。 Other photopolymerization initiators (C3) can be used alone or in combination of two or more.
光重合開始剤(C)の含有量は、重合性化合物(B)100質量部に対して、光硬化性の観点から、1~100質量部が好ましく、3~50質量部がより好ましく、5~25質量部がさらに好ましい。 From the viewpoint of photocurability, the content of the photopolymerization initiator (C) is preferably 1 to 100 parts by mass, more preferably 3 to 50 parts by mass, and 5 to 50 parts by mass, based on 100 parts by mass of the polymerizable compound (B). ˜25 parts by mass is more preferred.
[アルカリ可溶性樹脂(A)]
本発明の感光性組成物は、アルカリ可溶性樹脂(A)を含む。
[Alkali-soluble resin (A)]
The photosensitive composition of the present invention contains an alkali-soluble resin (A).
アルカリ可溶性樹脂(A)は、アルカリ現像液に溶解する樹脂であればよく、公知の樹脂を用いることができる。アルカリ可溶性樹脂(B)は、非感光性アルカリ可溶性樹脂、感光性アルカリ可溶性樹脂に分類できる。アルカリ可溶性樹脂(A)は、例えば、カルボ
キシル基、リン酸基、スルホン酸基、ヒドロキシル基、フェノール性ヒドロキシル基などのアルカリ可溶性基を有する。これらの中でも、カルボキシル基が好ましい。
非感光性アルカリ可溶性樹脂は、例えば、酸性基を有するアクリル樹脂、α-オレフィン/(無水)マレイン酸共重合体、スチレン/スチレンスルホン酸共重合体、エチレン/(メタ)アクリル酸共重合体、又はイソブチレン/(無水)マレイン酸共重合体等が挙げられる。感光性アルカリ可溶性樹脂は、重合性不飽和基を有するアルカリ可溶性樹脂である。また、アルカリ可溶性樹脂(A)は、エポキシ基やオキセタニル基等の熱硬化性基を含有できる。
The alkali-soluble resin (A) may be any resin that dissolves in an alkaline developer, and any known resin may be used. The alkali-soluble resin (B) can be classified into non-photosensitive alkali-soluble resins and photosensitive alkali-soluble resins. The alkali-soluble resin (A) has an alkali-soluble group such as a carboxyl group, a phosphoric acid group, a sulfonic acid group, a hydroxyl group, or a phenolic hydroxyl group. Among these, carboxyl groups are preferred.
Non-photosensitive alkali-soluble resins include, for example, acrylic resins having acidic groups, α-olefin/(anhydride) maleic acid copolymers, styrene/styrene sulfonic acid copolymers, ethylene/(meth)acrylic acid copolymers, Alternatively, examples include isobutylene/(anhydrous) maleic acid copolymer. The photosensitive alkali-soluble resin is an alkali-soluble resin having a polymerizable unsaturated group. Moreover, the alkali-soluble resin (A) can contain a thermosetting group such as an epoxy group or an oxetanyl group.
アルカリ可溶性樹脂(A)の重量平均分子量(Mw)は、現像性の観点から、2,000~40,000が好ましく、3,000~300,00がより好ましく、4,000~20,000がさらに好ましい。また、Mw/Mnの値は10以下が好ましい。適度な重量平均分子量(Mw)により基板に対する密着性、及び現像溶解性が向上する。 From the viewpoint of developability, the weight average molecular weight (Mw) of the alkali-soluble resin (A) is preferably from 2,000 to 40,000, more preferably from 3,000 to 300,00, and from 4,000 to 20,000. More preferred. Moreover, the value of Mw/Mn is preferably 10 or less. A suitable weight average molecular weight (Mw) improves adhesion to the substrate and development solubility.
アルカリ可溶性樹脂(A)の酸価は、50~200mgKOH/gが好ましく、70~180mgKOH/gがより好ましく、90~170mgKOH/gがさらに好ましい。適度な酸価により基板に対する密着性、及び現像溶解性が向上する。 The acid value of the alkali-soluble resin (A) is preferably 50 to 200 mgKOH/g, more preferably 70 to 180 mgKOH/g, even more preferably 90 to 170 mgKOH/g. A suitable acid value improves adhesion to the substrate and development solubility.
アルカリ可溶性樹脂(A)の含有量は、感光性組成物の不揮発分100質量%中、1~80質量%が好ましく、5~60質量%がより好ましく、10~50質量%がさらに好ましい。 The content of the alkali-soluble resin (A) is preferably 1 to 80% by weight, more preferably 5 to 60% by weight, and even more preferably 10 to 50% by weight based on 100% by weight of nonvolatile content of the photosensitive composition.
アルカリ可溶性樹脂(A)は、単独または2種類以上を併用して使用できる。 The alkali-soluble resin (A) can be used alone or in combination of two or more types.
アルカリ可溶性樹脂(A)は、パターン形成の観点から、感光性アルカリ可溶性樹脂を含むことが好ましい。 From the viewpoint of pattern formation, the alkali-soluble resin (A) preferably contains a photosensitive alkali-soluble resin.
(アルカリ可溶性樹脂(A1))
本発明の感光性組成物は、アルカリ可溶性樹脂(A)として、水しみの抑制、残膜率、パターン形成の観点から、脂環式炭化水素含有単量体単位(a1)、及びカルボキシル基含有単量体単位(a2)を含有するアルカリ可溶性樹脂(A1)を含むことが好ましい。
疎水性が高く、柔軟性と剛直性を兼ね備えた脂環式炭化水素構造は、現像液との親和性が低く強靭な被膜を形成できると推測され、水しみの抑制、残膜率、及びパターン形成性が向上する。そして、更に、高感度であるオキシム系光重合開始剤(C1)とオキシム系光重合開始剤(C2)とを組み合わせることで、より強靭な被膜が形成できたと推測する。
(Alkali-soluble resin (A1))
The photosensitive composition of the present invention, as the alkali-soluble resin (A), contains an alicyclic hydrocarbon-containing monomer unit (a1) and a carboxyl group-containing monomer unit from the viewpoint of suppressing water stains, remaining film rate, and pattern formation. It is preferable to include an alkali-soluble resin (A1) containing a monomer unit (a2).
The alicyclic hydrocarbon structure, which is highly hydrophobic and has both flexibility and rigidity, has a low affinity with developing solutions and is thought to be able to form a tough film, and is expected to suppress water stains, reduce film retention, and improve patterns. Formability is improved. Furthermore, it is presumed that a stronger coating could be formed by combining the highly sensitive oxime photopolymerization initiator (C1) and oxime photopolymerization initiator (C2).
〔脂環式炭化水素含有単量体単位(a1)〕
脂環式炭化水素含有単量体は、例えば、イソボロニル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、ジシクロペンタニルオキシエチル(メタ)アクリレート、ジシクロペンテニルオキシエチル(メタ)アクリレート、アダマンチル(メタ)アクリレート等が挙げられる。これらの中でも、パターン形成の観点から、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、ジシクロペンタニルオキシエチル(メタ)アクリレートが好ましい。
[Alicyclic hydrocarbon-containing monomer unit (a1)]
Alicyclic hydrocarbon-containing monomers include, for example, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, ) acrylate, dicyclopentenyloxyethyl (meth)acrylate, adamantyl (meth)acrylate, and the like. Among these, from the viewpoint of pattern formation, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, and dicyclopentanyloxyethyl (meth)acrylate are preferred.
〔カルボキシル基含有単量体単位(a2)〕
カルボキシル基含有単量体は、例えば、アクリル酸、メタクリル酸、クロトン酸、イタコン酸、マレイン酸、フマル酸等が挙げられる。また、α-(ヒドロキシメチル)アクリル酸のような、同一分子中にヒドロキシ基およびカルボキシル基を含有する単量体を併用
することもできる。これらの中でも、アクリル酸、メタクリル酸が好ましい。
[Carboxyl group-containing monomer unit (a2)]
Examples of the carboxyl group-containing monomer include acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, and fumaric acid. Furthermore, a monomer containing a hydroxy group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid, can also be used in combination. Among these, acrylic acid and methacrylic acid are preferred.
〔その他単量体単位(a3)〕
アルカリ可溶性樹脂(A1)は、脂環式炭化水素含有単量体(a1)、及びカルボキシル基含有単量体単位(a2)以外にその他単量体単位(a3)を含有できる。
[Other monomer units (a3)]
The alkali-soluble resin (A1) can contain other monomer units (a3) in addition to the alicyclic hydrocarbon-containing monomer (a1) and the carboxyl group-containing monomer unit (a2).
その他単量体は、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n-プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、n-ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、t-ブチル(メタ)アクリレート、2-エチルヘキシル(メタ)アクリレート、ステアリル(メタ)アクリレート、ラウリル(メタ)アクリレート、フェニル(メタ)アクリレート、ベンジル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、メトキシポリプロピレングリコール(メタ)アクリレート、エトキシポリエチレングリコール(メタ)アクリレート等の(メタ)アクリレート類;
2-ヒドロキシエチル(メタ)アクリレート、2-若しくは3-ヒドロキシプロピル(メタ)アクリレート、2-若しくは3-若しくは4-ヒドロキシブチル(メタ)アクリレート、グリセロールモノ(メタ)アクリレート、又はシクロヘキサンジメタノールモノ(メタ)アクリレート等の水酸基含有(メタ)アクリレート類;
ヒドロキシアルキル(メタ)アクリレートに、エチレンオキシド、プロピレンオキシド、及び/又はブチレンオキシド等を付加重合させたポリエーテルモノ(メタ)アクリレートや、ポリγ-バレロラクトン、ポリε-カプロラクトン、及び/又はポリ12-ヒドロキシステアリン酸等を付加したポリエステルモノ(メタ)アクリレート類;
グリシジル(メタ)アクリレート、メチルグリシジル(メタ)アクリレート、2-グリシドキシエチル(メタ)アクリレート、3,4-エポキシブチル(メタ)アクリレート、及び3,4-エポキシシクロヘキシル(メタ)アクリレート等のエポキシ基含有(メタ)アクリレート類;
(メタ)アクリルアミド、N,N-ジメチル(メタ)アクリルアミド、N,N-ジエチル(メタ)アクリルアミド、N-イソプロピル(メタ)アクリルアミド、ダイアセトン(メタ)アクリルアミド、又はアクリロイルモルホリン等の(メタ)アクリルアミド類;
スチレン、又はα-メチルスチレン等のスチレン類;
エチルビニルエーテル、n-プロピルビニルエーテル、イソプロピルビニルエーテル、n-ブチルビニルエーテル、又はイソブチルビニルエーテル等のビニルエーテル類;
酢酸ビニル、又はプロピオン酸ビニル等の脂肪酸ビニル類;
フェニルマレイミド、メチルマレイミド、エチルマレイミド、1,2-ビスマレイミドエタン1,6-ビスマレイミドヘキサン、3-マレイミドプロピオン酸、6,7-メチレンジオキシ-4-メチル-3-マレイミドクマリン、4,4’-ビスマレイミドジフェニルメタン、ビス(3-エチル-5-メチル-4-マレイミドフェニル)メタン、N,N’-1,3-フェニレンジマレイミド、N,N’-1,4-フェニレンジマレイミド、N-(1-ピレニル)マレイミド、N-(2,4,6-トリクロロフェニル)マレイミド、N-(4-アミノフェニル)マレイミド、N-(4-ニトロフェニル)マレイミド、N-ベンジルマレイミド、N-ブロモメチル-2,3-ジクロロマレイミド、N-スクシンイミジル-3-マレイミドベンゾエ-ト、N-スクシンイミジル-3-マレイミドプロピオナ-ト、N-スクシンイミジル-4-マレイミドブチラ-ト、N-スクシンイミジル-6-マレイミドヘキサノア-ト、N-[4-(2-ベンゾイミダゾリル)フェニル]マレイミド、9-マレイミドアクリジン等のN-置換マレイミド類;
2-(メタ)アクリロイルオキシエチルアシッドフォスフェート、上述した水酸基含有(メタ)アクリレートの水酸基に、たとえば5酸化リンやポリリン酸等のリン酸エステル化剤を反応させた化合物等のリン酸エステル基含有(メタ)アクリレート類等が挙げられる。
Other monomers include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t- Butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, phenyl (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth) (Meth)acrylates such as acrylate, methoxypolypropylene glycol (meth)acrylate, and ethoxypolyethylene glycol (meth)acrylate;
2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 2- or 3- or 4-hydroxybutyl (meth)acrylate, glycerol mono(meth)acrylate, or cyclohexanedimethanol mono(meth)acrylate ) Hydroxyl group-containing (meth)acrylates such as acrylate;
Polyether mono(meth)acrylate obtained by addition polymerizing ethylene oxide, propylene oxide, and/or butylene oxide, etc. to hydroxyalkyl (meth)acrylate, polyγ-valerolactone, polyε-caprolactone, and/or poly12- Polyester mono(meth)acrylates with added hydroxystearic acid, etc.;
Epoxy groups such as glycidyl (meth)acrylate, methylglycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate Contains (meth)acrylates;
(Meth)acrylamides such as (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-isopropyl (meth)acrylamide, diacetone (meth)acrylamide, or acryloylmorpholine. ;
Styrene or styrenes such as α-methylstyrene;
Vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether;
Fatty acid vinyls such as vinyl acetate or vinyl propionate;
Phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimidoethane 1,6-bismaleimidehexane, 3-maleimidopropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimidocoumarin, 4,4 '-Bismaleimidodiphenylmethane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, N,N'-1,3-phenylene dimaleimide, N,N'-1,4-phenylene dimaleimide, N -(1-pyrenyl)maleimide, N-(2,4,6-trichlorophenyl)maleimide, N-(4-aminophenyl)maleimide, N-(4-nitrophenyl)maleimide, N-benzylmaleimide, N-bromomethyl -2,3-dichloromaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6- N-substituted maleimides such as maleimide hexanoate, N-[4-(2-benzimidazolyl)phenyl]maleimide, and 9-maleimidoacridine;
2-(meth)acryloyloxyethyl acid phosphate, a compound containing a phosphoric acid ester group, such as a compound obtained by reacting a phosphoric acid esterification agent such as phosphorus pentoxide or polyphosphoric acid with the hydroxyl group of the above-mentioned hydroxyl group-containing (meth)acrylate. Examples include (meth)acrylates.
アルカリ可溶性樹脂(A1)は、脂環式炭化水素含有単量体単位(a1)、及びカルボキシル基含有単量体単位(a2)を含有すれば良く、その合成方法は限定されない。以下、好ましい合成法である方法(i)、方法(ii)を説明する。 The alkali-soluble resin (A1) may contain an alicyclic hydrocarbon-containing monomer unit (a1) and a carboxyl group-containing monomer unit (a2), and its synthesis method is not limited. Preferred synthesis methods, method (i) and method (ii), will be explained below.
<方法(i)>
方法(i)は、例えば、脂環式炭化水素含有単量体、及びカルボキシル基含有単量体の共重合体を合成することで、アルカリ可溶性樹脂(A1)を合成できる。
<Method (i)>
In method (i), for example, the alkali-soluble resin (A1) can be synthesized by synthesizing a copolymer of an alicyclic hydrocarbon-containing monomer and a carboxyl group-containing monomer.
<方法(ii)>
方法(ii)は、例えば、脂環式炭化水素含有単量体、及びエポキシ基含有単量体の共重合体を合成する。次いで、前記共重合体のエポキシ基に、カルボキシル基含有単量体を付加し、生成した水酸基と酸無水物とをエステル化反応させることで、アルカリ可溶性樹脂(A1)を合成できる。
<Method (ii)>
In method (ii), for example, a copolymer of an alicyclic hydrocarbon-containing monomer and an epoxy group-containing monomer is synthesized. Next, an alkali-soluble resin (A1) can be synthesized by adding a carboxyl group-containing monomer to the epoxy group of the copolymer and causing an esterification reaction between the generated hydroxyl group and an acid anhydride.
エポキシ基含有単量体は、例えば、グリシジル(メタ)アクリレート、メチルグリシジル(メタ)アクリレート、2-グリシドキシエチル(メタ)アクリレート、3,4-エポキシブチル(メタ)アクリレート、及び3,4-エポキシシクロヘキシル(メタ)アクリレートが挙げられる。これらの中でも、反応性の観点で、グリシジル(メタ)アクリレートが好ましい。 Epoxy group-containing monomers include, for example, glycidyl (meth)acrylate, methylglycidyl (meth)acrylate, 2-glycidoxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4- Epoxycyclohexyl (meth)acrylate is mentioned. Among these, glycidyl (meth)acrylate is preferred from the viewpoint of reactivity.
酸無水物は、例えば、テトラヒドロ無水フタル酸、無水フタル酸、ヘキサヒドロ無水フタル酸、無水コハク酸、無水マレイン酸等が挙げられる。これらは、単独又は2種以上併用して使用できる。 Examples of the acid anhydride include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, maleic anhydride, and the like. These can be used alone or in combination of two or more.
脂環式炭化水素含有単量体単位(a1)の含有量は、水しみの抑制、パターン形成の観点から、アルカリ可溶性樹脂(A1)の全構成単位100質量%中、5~60質量が好ましく、10~50質量%がより好ましい。 The content of the alicyclic hydrocarbon-containing monomer unit (a1) is preferably 5 to 60% by mass based on 100% by mass of the total constituent units of the alkali-soluble resin (A1) from the viewpoint of suppressing water stains and forming a pattern. , more preferably 10 to 50% by mass.
アルカリ可溶性樹脂(A1)の含有量は、水しみの抑制、残膜率、及びパターン形成の観点から、アルカリ可溶性樹脂(A)100質量%中、50質量%以上が好ましく、70質量%以上がより好ましい。 The content of the alkali-soluble resin (A1) is preferably 50% by mass or more, and 70% by mass or more in 100% by mass of the alkali-soluble resin (A) from the viewpoint of suppressing water stains, remaining film rate, and pattern formation. More preferred.
(アルカリ可溶性樹脂(A2))
本発明の感光性組成物は、アルカリ可溶性樹脂(A)として、アルカリ可溶性樹脂(A1)以外のアルカリ可溶性樹脂(A2)を含有することができる。
(Alkali-soluble resin (A2))
The photosensitive composition of the present invention can contain an alkali-soluble resin (A2) other than the alkali-soluble resin (A1) as the alkali-soluble resin (A).
[重合性化合物(B)]
本発明の感光性組成物は、重合性化合物(B)を含む。
[Polymerizable compound (B)]
The photosensitive composition of the present invention contains a polymerizable compound (B).
重合性化合物(B)は、モノマー、オリゴマーが挙げられる。重合性不飽和基は、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、(メタ)アクリロイルオキシ基等が挙げられる。重合性化合物(B)は、例えば、ラクトン変性された重合性化合物(B1)、酸基を有する重合性化合物(B2)、ウレタン結合を有する重合性化合物(B3)、その他重合性化合物(B4)等が挙げられる。 Examples of the polymerizable compound (B) include monomers and oligomers. Examples of the polymerizable unsaturated group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and a (meth)acryloyloxy group. Examples of the polymerizable compound (B) include a lactone-modified polymerizable compound (B1), a polymerizable compound having an acid group (B2), a polymerizable compound having a urethane bond (B3), and other polymerizable compounds (B4). etc.
(ラクトン変性された重合性化合物(B1))
本発明の感光性組成物は、水しみの抑制の観点から、ラクトン変性された重合性化合物(B1)を含むことが好ましい。
(Lactone-modified polymerizable compound (B1))
The photosensitive composition of the present invention preferably contains a lactone-modified polymerizable compound (B1) from the viewpoint of suppressing water stains.
ラクトン変性された重合性化合物(B1)は、分子内にラクトンで変性された構造を有
する化合物である。ラクトン変性された重合性化合物(B1)は、トリメチロールエタン、ジトリメチロールエタン、トリメチロールプロパン、ジトリメチロールプロパン、ペンタエチスリトール、トリペンタエリスリトール、グリセリン、ジグリセロール、トリメトロールメラミン等の多価アルコールと、(メタ)アクリル酸およびε-カプロラクトンもしくはその他のラクトン化合物をエステル化することにより得られる。ラクトン変性された重合性化合物(B1)は、下記一般式(17)で表される化合物が好ましい。
The lactone-modified polymerizable compound (B1) is a compound having a lactone-modified structure in its molecule. The lactone-modified polymerizable compound (B1) is a polyhydric alcohol such as trimethylolethane, ditrimethylolethane, trimethylolpropane, ditrimethylolpropane, pentaethythritol, tripentaerythritol, glycerin, diglycerol, and trimerolmelamine. It can be obtained by esterifying (meth)acrylic acid and ε-caprolactone or other lactone compounds. The lactone-modified polymerizable compound (B1) is preferably a compound represented by the following general formula (17).
一般式(17)
一般式(17)中、6個のRは全て下記一般式(18)で表される基、または6個のRのうち1~5個が下記一般式(18)で表される基であり、残りが下記一般式(19)で表される基である。 In general formula (17), all six R's are groups represented by the following general formula (18), or 1 to 5 of the six Rs are groups represented by the following general formula (18). , the remainder is a group represented by the following general formula (19).
一般式(18)
General formula (18)
一般式(18)中、R1は水素原子、またはメチル基を表し、mは1、または2の整数であり、*は一般式(17)の酸素原子と結合する結合手である。 In the general formula (18), R 1 represents a hydrogen atom or a methyl group, m is an integer of 1 or 2, and * is a bond bonding to the oxygen atom of the general formula (17).
一般式(19)
General formula (19)
一般式(19)中、R1は水素原子、またはメチル基を表し、*は一般式(17)の酸素原子と結合する結合手である。 In the general formula (19), R 1 represents a hydrogen atom or a methyl group, and * is a bond bonding to the oxygen atom of the general formula (17).
ラクトン変性された重合性化合物(B1)は、例えば、日本化薬社製のKAYARAD
DPCAシリーズとして市販されており、DPCA-20(上記一般式(17)~(19)において、m=1、一般式(18)に表される基の数=2、R1が全て水素原子である化合物)、DPCA-30(上記一般式(17)~(19)において、m=1、一般式(18)に表される基の数=3、R1が全て水素原子である化合物)、DPCA-60(上記一般式(17)~(19)において、m=1、一般式(18)に表される基の数=6
、R1が全て水素原子である化合物)、DPCA-120(上記一般式(17)~(19)において、m=2、一般式(18)に表される基の数=6、R1が全て水素原子である化合物)等が挙げられる。
The lactone-modified polymerizable compound (B1) is, for example, KAYARAD manufactured by Nippon Kayaku Co., Ltd.
It is commercially available as the DPCA series, and DPCA-20 (in the above general formulas (17) to (19), m = 1, the number of groups represented by general formula (18) = 2, and R 1 is all hydrogen atoms) (a certain compound), DPCA-30 (a compound in which in the above general formulas (17) to (19), m = 1, the number of groups represented by general formula (18) = 3, and all R 1 are hydrogen atoms), DPCA-60 (in the above general formulas (17) to (19), m = 1, the number of groups represented by general formula (18) = 6
, a compound in which R 1 is all hydrogen atoms), DPCA-120 (in the above general formulas (17) to (19), m = 2, the number of groups represented by general formula (18) = 6, R 1 is (compounds in which all hydrogen atoms are hydrogen atoms), etc.
ラクトン変性された重合性化合物(B1)は、水しみの抑制の観点から、上記一般式(17)~(19)において、m=1、一般式(18)に表される基の数=2~6、R1が全て水素原子である化合物が好ましく、上記一般式(17)~(19)において、m=1、一般式(18)に表される基の数=2又は3、R1が全て水素原子である化合物がより好ましい。 From the viewpoint of suppressing water stains, the lactone-modified polymerizable compound (B1) has m=1 in the above general formulas (17) to (19), and the number of groups represented by general formula (18)=2. ~6, compounds in which all R 1 are hydrogen atoms are preferred; in the above general formulas (17) to (19), m = 1, the number of groups represented by general formula (18) = 2 or 3, R 1 A compound in which all are hydrogen atoms is more preferred.
ラクトン変性された重合性化合物(B1)の含有量は、水しみの抑制の観点から、重合性化合物(B)100質量%中、5~80質量%が好ましく、10~70質量%がより好ましく、20~60質量%がさらに好ましい。 From the viewpoint of suppressing water stains, the content of the lactone-modified polymerizable compound (B1) is preferably 5 to 80% by mass, more preferably 10 to 70% by mass based on 100% by mass of the polymerizable compound (B). , more preferably 20 to 60% by mass.
(酸基を有する重合性化合物(B2))
本発明の感光性組成物は、アルカリ現像性、パターン形成の観点から、酸基を有する重合性化合物(B2)を含むことが好ましい。酸基を有する重合性化合物(B2)の酸基は、例えば、スルホン酸基、カルボキシル基、リン酸基等を挙げられる。これらの中でも、カルボキシル基が好ましい。
(Polymerizable compound (B2) having an acid group)
The photosensitive composition of the present invention preferably contains a polymerizable compound (B2) having an acid group from the viewpoint of alkali developability and pattern formation. Examples of the acid group of the polymerizable compound (B2) having an acid group include a sulfonic acid group, a carboxyl group, and a phosphoric acid group. Among these, carboxyl groups are preferred.
酸基を有する重合性化合物(B2)は、例えば、多価アルコールと(メタ)アクリル酸との遊離水酸基含有ポリ(メタ)アクリレート類と、ジカルボン酸類とのエステル化物;多価カルボン酸と、モノヒドロキシアルキル(メタ)アクリレート類とのエステル化物等を挙げられる。
多価アルコールは、例えば、エチレングリコール、プロピレングリコール、ポリエチレングリコール、ポリプロピレングリコール、グリセリン、トリメチロールプロパン、ジトリメチロールプロパン、ペンタエリスリトール、ジペンタエリスリトール等が挙げられる。
ジカルボン酸類は、例えば、マロン酸、コハク酸、マレイン酸、グルタル酸、フタル酸イタコン酸等が挙げられる。
多価カルボン酸は、例えば、トリメリット酸、ピロメリット酸等が挙げられる。
モノヒドロキシアルキル(メタ)アクリレート類は、例えば、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、4-ヒドロキシブチル(メタ)アクリレート、ペンタエリスリトールトリアクリレート、2-ヒドロキシ-3-アクリロイロキシプロピルメタクリレート等が挙げられる。
The polymerizable compound (B2) having an acid group is, for example, an esterified product of a free hydroxyl group-containing poly(meth)acrylate of a polyhydric alcohol and (meth)acrylic acid, and a dicarboxylic acid; Examples include esterified products with hydroxyalkyl (meth)acrylates.
Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, glycerin, trimethylolpropane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, and the like.
Examples of dicarboxylic acids include malonic acid, succinic acid, maleic acid, glutaric acid, phthalic acid, itaconic acid, and the like.
Examples of polyhydric carboxylic acids include trimellitic acid and pyromellitic acid.
Examples of monohydroxyalkyl (meth)acrylates include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and pentaerythritol. Examples include triacrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, and the like.
酸基を有する重合性化合物(B2)の市販品は、大阪有機社製のビスコート#2500P、東亞合成社製アロニックスM-5300,M-5400,M-5700,M-510,M-520,M-521等が挙げられる。 Commercial products of the polymerizable compound (B2) having an acid group include Viscoat #2500P manufactured by Osaka Organic Co., Ltd. and Aronix M-5300, M-5400, M-5700, M-510, M-520, and M manufactured by Toagosei Co., Ltd. -521 etc. are mentioned.
酸基を有する重合性化合物(B2)の含有量は、アルカリ現像性、パターン形成の観点から、重合性化合物(B)100質量%中、5~80質量%が好ましく、10~70質量部%であることがより好ましく、20~60質量%であることがさらに好ましい。 From the viewpoint of alkali developability and pattern formation, the content of the polymerizable compound (B2) having an acid group is preferably 5 to 80% by mass, and 10 to 70 parts by mass based on 100% by mass of the polymerizable compound (B). It is more preferable that the amount is 20 to 60% by mass.
(ウレタン結合を有する重合性化合物(B3))
本発明の感光性組成物は、パターン形成の観点から、ウレタン結合を有する重合性化合物(B3)を含むことが好ましい。
(Polymerizable compound (B3) having a urethane bond)
From the viewpoint of pattern formation, the photosensitive composition of the present invention preferably contains a polymerizable compound (B3) having a urethane bond.
ウレタン結合を有する重合性化合物(B3)は、例えば、水酸基を有する(メタ)アク
リレートに多官能イソシアネートを反応させて得られるウレタン(メタ)アクリレートや、多価アルコールに多官能イソシアネートを反応させ、さらに水酸基を有する(メタ)アクリレートを反応させて得られるウレタン(メタ)アクリレート等が挙げられる。
The polymerizable compound (B3) having a urethane bond is, for example, a urethane (meth)acrylate obtained by reacting a polyfunctional isocyanate with a (meth)acrylate having a hydroxyl group, or a polyfunctional isocyanate obtained by reacting a polyhydric alcohol with a polyfunctional isocyanate. Examples include urethane (meth)acrylate obtained by reacting (meth)acrylate having a hydroxyl group.
上記水酸基を有する(メタ)アクリレートは、例えば、2-ヒドロキシエチル(メタ)
アクリレート、4-ヒドロキシブチル(メタ)アクリレート、トリメチロールプロパンジ
(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ジトリメチロールプロパントリ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールエチレンオキサイド変性ペンタ(メタ)アクリレート、ジペンタエリスリトールプロピレンオキサイド変性ペンタ(メタ)アクリレート、ジペンタエリスリトールカプロラクトン変性ペンタ(メタ)アクリレート、グリセロールアクリレートメタクリレート、グリセロールジメタクリレート、2-ヒドロキシ-3-アクリロイ
ルプロピルメタクリレート、エポキシ基含有化合物とカルボキシ(メタ)アクリレートの反応物、水酸基含有ポリオールポリアクリレート等が挙げられる。
The (meth)acrylate having a hydroxyl group is, for example, 2-hydroxyethyl (meth)
Acrylate, 4-hydroxybutyl (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol ethylene Oxide-modified penta(meth)acrylate, dipentaerythritol propylene oxide-modified penta(meth)acrylate, dipentaerythritol caprolactone-modified penta(meth)acrylate, glycerol acrylate methacrylate, glycerol dimethacrylate, 2-hydroxy-3-acryloylpropyl methacrylate, epoxy Examples include reaction products of group-containing compounds and carboxy (meth)acrylates, hydroxyl group-containing polyol polyacrylates, and the like.
上記多官能イソシアネートは、例えば、芳香族ジイソシアネートであるトリレンジイソシアネート、ジフェニルメチレンジイソシアネート、キシレンジイソシアネート、脂肪族ジイソシアネートであるトリメチレンジイソシアネート、テトラメチレンジイソシアネート、ヘキサメチレンジイソシアネート、脂環式ジイソシアネートであるイソホロンジイソシアネートや、これらのビュレット体、イソシアネートヌレート体、トリメチロールプロパンアダクト体等が挙げられる。 Examples of the polyfunctional isocyanates include aromatic diisocyanates such as tolylene diisocyanate, diphenylmethylene diisocyanate, and xylene diisocyanate, aliphatic diisocyanates such as trimethylene diisocyanate, tetramethylene diisocyanate, and hexamethylene diisocyanate, and alicyclic diisocyanate such as isophorone diisocyanate. , their burette bodies, isocyanate nurate bodies, trimethylolpropane adducts, and the like.
ウレタン結合を有する重合性化合物(B3)は、現像性の観点から、更に、酸基を有することも好ましい。酸基は、例えば、スルホン酸基、カルボキシル基、リン酸基等を挙げられる。なかでも、カルボキシル基が好ましい。 From the viewpoint of developability, it is also preferable that the polymerizable compound (B3) having a urethane bond further has an acid group. Examples of acid groups include sulfonic acid groups, carboxyl groups, and phosphoric acid groups. Among these, a carboxyl group is preferred.
ウレタン結合を有する重合性化合物(B3)に酸基を導入する方法は、例えば、まず、上記水酸基を有する(メタ)アクリレートと上記多官能イソシアネートとを反応させる。次いで、生成物にカルボキシル基を有するメルカプト化合物を付加させる方法で合成できる。 As a method for introducing an acid group into the polymerizable compound (B3) having a urethane bond, for example, first, the above-mentioned (meth)acrylate having a hydroxyl group and the above-mentioned polyfunctional isocyanate are reacted. Next, it can be synthesized by adding a mercapto compound having a carboxyl group to the product.
上記カルボキシル基を有するメルカプト化合物は、例えば、メルカプト酢酸、2-メルカプトプロピオン酸、3-メルカプトプロピオン酸、o-メルカプト安息香酸、2-メルカプトニコチン酸、メルカプトコハク酸等が挙げられる。 Examples of the above-mentioned mercapto compounds having a carboxyl group include mercaptoacetic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, o-mercaptobenzoic acid, 2-mercaptonicotinic acid, and mercaptosuccinic acid.
ウレタン結合を有する重合性化合物(B3)の含有量は、パターン形成の観点から、重合性化合物(B)100質量%中、5~80質量%が好ましく、10~70質量部%がより好ましく、20~60質量%がさらに好ましい。 From the viewpoint of pattern formation, the content of the polymerizable compound (B3) having a urethane bond is preferably 5 to 80 parts by mass, more preferably 10 to 70 parts by mass, based on 100 parts by mass of the polymerizable compound (B). More preferably 20 to 60% by mass.
(その他重合性化合物(B4))
その他重合性化合物(B4)は、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、β-カルボキシエチル(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、1,6-ヘキサンジオ-ルジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、トリメチロ-ルプロパントリ(メタ)アクリレート、フェノキシテトラエチレングリコール(メタ)アクリレート、フェノキシヘキサエチレングリコール(メタ)アクリレート、トリメチロ-ルプロパンPO変性トリ(メタ)アクリレート、トリメチロ-ルプロパンEO変性トリ(メタ)アクリレート、イソシアヌル酸EO変性ジ(メタ)アクリレート、イソシアヌル酸EO変性トリ(メタ)
アクリレート、ジトリメチロ-ルプロパンテトラ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、1,6-ヘキサンジオ-ルジグリシジルエーテルジ(メタ)アクリレート、ビスフェノールAジグリシジルエーテルジ(メタ)アクリレート、ネオペンチルグリコールジグリシジルエーテルジ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、トリシクロデカニル(メタ)アクリレート、メチロ-ル化メラミンの(メタ)アクリル酸エステル、エポキシ(メタ)アクリレート等の各種アクリル酸エステル及びメタクリル酸エステル、スチレン、酢酸ビニル、ヒドロキシエチルビニルエーテル、エチレングリコールジビニルエーテル、ペンタエリスリトールトリビニルエーテル、(メタ)アクリルアミド、N-ヒドロキシメチル(メタ)アクリルアミド、N-ビニルホルムアミド、アクリロニトリル等が挙げられる。
(Other polymerizable compounds (B4))
Other polymerizable compounds (B4) include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxylic Ethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate , phenoxytetraethylene glycol (meth)acrylate, phenoxyhexaethylene glycol (meth)acrylate, trimethylolpropane PO modified tri(meth)acrylate, trimethylolpropane EO modified tri(meth)acrylate, isocyanuric acid EO modified di(meth)acrylate , isocyanuric acid EO modified tri(meth)
Acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, 1,6-hexanediol diglycidyl ether di(meth)acrylate, bisphenol A diglycidyl ether di( meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecanyl(meth)acrylate, methylolated melamine ( Various acrylic esters and methacrylic esters such as meth)acrylic esters and epoxy(meth)acrylates, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl Examples include (meth)acrylamide, N-vinylformamide, acrylonitrile, and the like.
その他重合性化合物(B4)の市販品は、例えば、日本化薬社製のKAYARAD R-128H、R526、PEG400DA、MAND、NPGDA、R-167、HX-220、R-551、R712、R-604、R-684、GPO-303、TMPTA、DPHA、DPEA-12、DPHA-2C、D-310、D-330、及び東亞合成社製のアロニックスM-303、M-305、M-306、M-309、M-310、M-321、M-325、M-350、M-360、M-313、M-315、M-400、M-402、M-403、M-404、M-405、M-406、M-450、M-452、M-408、M-211B、M-101A、大阪有機社製のビスコート#310HP、#335HP、#700、#295、#330、#360、#GPT、#400、#405、共栄社化学社製のAH-600、AT-600、新中村化学社製のNKエステルA-9300,ABE-300,A-DOG,A-DCP,A-BPE-4、ダイセル・オルネクス社製のEBECRYL40,130,140,145、大阪ガスケミカル社製のOGSOL EA-0200,0300等が挙げられる。
等が挙げられる。
Other commercially available polymerizable compounds (B4) include, for example, KAYARAD R-128H, R526, PEG400DA, MAND, NPGDA, R-167, HX-220, R-551, R712, and R-604 manufactured by Nippon Kayaku Co., Ltd. , R-684, GPO-303, TMPTA, DPHA, DPEA-12, DPHA-2C, D-310, D-330, and Aronix M-303, M-305, M-306, M- manufactured by Toagosei Co., Ltd. 309, M-310, M-321, M-325, M-350, M-360, M-313, M-315, M-400, M-402, M-403, M-404, M-405, M-406, M-450, M-452, M-408, M-211B, M-101A, Viscoat #310HP, #335HP, #700, #295, #330, #360, #GPT manufactured by Osaka Organic Co., Ltd. , #400, #405, AH-600, AT-600 manufactured by Kyoeisha Chemical Co., Ltd., NK Ester A-9300, ABE-300, A-DOG, A-DCP, A-BPE-4 manufactured by Shin-Nakamura Chemical Co., Ltd. Examples include EBECRYL40, 130, 140, 145 manufactured by Daicel Allnex Corporation, and OGSOL EA-0200, 0300 manufactured by Osaka Gas Chemical Company.
etc.
重合性化合物(B)は、単独または2種類以上を併用して使用できる。 The polymerizable compound (B) can be used alone or in combination of two or more types.
重合性化合物(B)は、水しみの抑制、残膜率、及びパターン形成の観点から、ラクトン変性された重合性化合物(B1)、酸基を有する重合性化合物(B2)、及びウレタン結合及び酸基を有する重合性化合物(B3)からなる群から選ばれるいずれか1種以上を含むことが好ましく、2種以上を含むことがより好ましい。 The polymerizable compound (B) is a lactone-modified polymerizable compound (B1), an acid group-containing polymerizable compound (B2), and a urethane bond and a urethane bond. It is preferable to contain at least one kind selected from the group consisting of polymerizable compounds (B3) having an acid group, and more preferably to contain two or more kinds.
重合性化合物(B)の含有量は、感光性組成物の不揮発分100質量%中、1~60質量%が好ましく、2~50質量%がより好ましい。 The content of the polymerizable compound (B) is preferably 1 to 60% by weight, more preferably 2 to 50% by weight based on 100% by weight of the nonvolatile content of the photosensitive composition.
[チオール系連鎖移動剤(D)]
本発明の感光性組成物は、水しみの抑制、パターン形成の観点から、チオール系連鎖移動剤(D)を含むことが好ましい。
[Thiol chain transfer agent (D)]
The photosensitive composition of the present invention preferably contains a thiol chain transfer agent (D) from the viewpoint of suppressing water stains and forming a pattern.
チオール系連鎖移動剤(D)は、チオール基(SH基)を2以上有する多官能チオールが好ましい。なお、チオール系連鎖移動剤は、SH基を4以上有することがより好ましい。官能基数が増えると被膜の表面から最深部まで光硬化し易くなる。 The thiol chain transfer agent (D) is preferably a polyfunctional thiol having two or more thiol groups (SH groups). In addition, it is more preferable that the thiol-based chain transfer agent has 4 or more SH groups. As the number of functional groups increases, it becomes easier to photocure from the surface of the film to the deepest part.
多官能チオールは、例えば、ヘキサンジチオール、デカンジチオール、1,4-ブタンジオールビスチオプロピオネート、1,4-ブタンジオールビスチオグリコレート、エチレングリコールビスチオグリコレート、エチレングリコールビスチオプロピオネート、トリメチロ-ルプロパントリスチオグリコレート、トリメチロ-ルプロパントリスチオプロピオネート、トリメチロ-ルプロパントリス(3-メルカプトブチレート)、ペンタエリ
スリトールテトラキスチオグリコレート、ペンタエリスリトールテトラキスチオプロピオネート、トリメルカプトプロピオン酸トリス(2-ヒドロキシエチル)イソシアヌレート、1,4-ジメチルメルカプトベンゼン、2、4、6-トリメルカプト-s-トリアジン、2-(N,N-ジブチルアミノ)-4,6-ジメルカプト-s-トリアジンなどが挙げられ、好ましくは、エチレングリコールビスチオプロピオネート、トリメチロールプロパントリスチオプロピオネート、ペンタエリスリトールテトラキスチオプロピオネート等が挙げられる。
Examples of polyfunctional thiols include hexanedithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, and ethylene glycol bisthiopropionate. , trimethylolpropane tristhioglycolate, trimethylolpropane tristhiopropionate, trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakisthioglycolate, pentaerythritol tetrakisthiopropionate, trimercapto Tris(2-hydroxyethyl)propionate isocyanurate, 1,4-dimethylmercaptobenzene, 2,4,6-trimercapto-s-triazine, 2-(N,N-dibutylamino)-4,6-dimercapto- Examples include s-triazine, and preferred examples include ethylene glycol bisthiopropionate, trimethylolpropane tristhiopropionate, and pentaerythritol tetrakisthiopropionate.
チオール系連鎖移動剤(D)は、単独または2種類以上を併用して使用できる。 The thiol chain transfer agent (D) can be used alone or in combination of two or more types.
チオール系連鎖移動剤(D)の含有量は、感光性組成物の不揮発分100質量部中、1~10質量部が好ましく、2~8質量部がより好ましい。 The content of the thiol-based chain transfer agent (D) is preferably 1 to 10 parts by weight, more preferably 2 to 8 parts by weight, based on 100 parts by weight of the nonvolatile content of the photosensitive composition.
[着色剤(E)]
本発明の感光性組成物は、着色剤(E)を含有できる。
[Colorant (E)]
The photosensitive composition of the present invention can contain a colorant (E).
着色剤(E)は、顔料、及び染料のいずれでもよく、併用できる。 The colorant (E) may be either a pigment or a dye, and they can be used in combination.
(顔料)
顔料は、カラーインデックスにおいてピグメントに分類されている化合物である。
赤色顔料は、例えば、C.I.ピグメントレッド1,2,3,4,5,6,7,8,9,12,14,15,16,17,21,22,23,31,32,37,38,41,47,48,48:1,48:2,48:3,48:4,49,49:1,49:2,50:1,52:1,52:2,53,53:1,53:2,53:3,57,57:1,57:2,58:4,60,63,63:1,63:2,64,64:1,68,69,81,81:1,81:2,81:3,81:4,83,88,90:1,101,101:1,104,108,108:1,109,112,113,114,122,123,144,146,147,149,151,166,168,169,170,172,173,174,175,176,177,178,179,181,184,185,187,188,190,193,194,200,202,206,207,208,209,210,214,216,220,221,224,230,231,232,233,235,236,237,238,239,242,243,245,247,249,250,251,253,254,255,256,257,258,259,260,262,263,264,265,266,267,268,269,270,271,272,273,274,275,276,277,278,279,280,281,282,283,284,285,286,287,291,295,296、特開2014-134712号公報に記載された顔料、特許第6368844号公報に記載された顔料等が挙げられる。これらの中でも、耐熱性、耐光性、及び透過率の観点から、C.I.ピグメントレッド48:1,122,177,224,242,269,254,291,295,296、特開2014-134712号公報に記載された顔料、特許第6368844号公報に記載された顔料が好ましく、C.I.ピグメントレッド177,254,291,295,296、特開2014-134712号公報に記載された顔料、特許第6368844号公報に記載された顔料がさらに好ましい。
(pigment)
Pigments are compounds classified as pigments in the color index.
The red pigment is, for example, C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53: 3,57,57:1,57:2,58:4,60,63,63:1,63:2,64,64:1,68,69,81,81:1,81:2,81: 3,81:4,83,88,90:1,101,101:1,104,108,108:1,109,112,113,114,122,123,144,146,147,149,151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, 280, 281,282,283,284,285,286,287,291,295,296, pigments described in JP-A-2014-134712, pigments described in Japanese Patent No. 6368844, and the like. Among these, from the viewpoint of heat resistance, light resistance, and transmittance, C. I. Pigment Red 48:1,122,177,224,242,269,254,291,295,296, the pigment described in JP2014-134712A, the pigment described in Japanese Patent No. 6368844 are preferable, C. I. Pigment Red 177,254,291,295,296, the pigment described in Japanese Patent Application Publication No. 2014-134712, and the pigment described in Japanese Patent No. 6368844 are more preferable.
橙色顔料は、例えば、C.I.ピグメントオレンジ36,38,43,64,71,73等が挙げられる。 The orange pigment is, for example, C.I. I. Pigment Orange 36, 38, 43, 64, 71, 73 and the like.
黄色顔料は、例えば、C.I.ピグメントイエロー1,2,3,4,5,6,10,12,13,14,15,16,17,18,24,31,32,34,35,35:1,36,36:1,37,37:1,40,42,43,53,55,60,61,62,6
3,65,73,74,77,81,83,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118,119,120,123,126,127,128,129,138,139,147,150,151,152、153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,192,193,194,196,198,199,213,214,231,233、特開2012-226110号公報に記載された顔料等が挙げられる。これらの中でも、C.I.ピグメントイエロー138,139,150,185,231,233、特開2012-226110号公報に記載された顔料が好ましい。
Yellow pigments include, for example, C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 6
3,65,73,74,77,81,83,93,94,95,97,98,100,101,104,106,108,109,110,113,114,115,116,117,118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 192, 193, 194, 196, 198, 199, 213, 214, 231, 233, JP Examples include pigments described in 2012-226110. Among these, C. I. Pigment Yellow 138, 139, 150, 185, 231, 233 and the pigments described in JP 2012-226110 A are preferred.
緑色顔料は、例えば、C.I.ピグメントグリーン1,2,4,7,8,10,13,14,15,17,18,19,26,36,37,45,48,50,51,54,55,58,59,62,63等が挙げられる。これらの中でも、C.I.ピグメントグリーン36、58、59、62、63が好ましい。 The green pigment is, for example, C.I. I. Pigment Green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, 59, 62, 63 etc. are mentioned. Among these, C. I. Pigment Green 36, 58, 59, 62, and 63 are preferred.
青色顔料は、例えば、C.I.ピグメントブルー1,1:2,9,14,15,15:1,15:2,15:3,15:4,15:6,16,17,19,25,27,28,29,33,35,36,56,56:1,60,61,61:1,62,63,66,67,68,71,72,73,74,75,76,78,79等が挙げられる。これらの中でも、C.I.ピグメントブルー15,15:1,15:2,15:3,15:4,15:6が好ましい。 The blue pigment is, for example, C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 25, 27, 28, 29, 33, Examples include 35, 36, 56, 56:1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79, and the like. Among these, C. I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, and 15:6 are preferred.
紫色顔料は、例えば、C.I.ピグメントバイオレット1,1:1,2,2:2,3,3:1,3:3,5,5:1,14,15,16,19,23,25,27,29,31,32,37,39,42,44,47,49,50等が挙げられる。これらの中でも、C.I.ピグメントバイオレット19,23が好ましい。 The purple pigment is, for example, C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50, etc. Among these, C. I. Pigment Violet 19 and 23 are preferred.
黒色顔料は、具体的には、C.I.ピグメントブラック1,6,7,12,20,31等が挙げられる。また、赤色顔料、黄色顔料、青色顔料、緑色顔料、及び紫色顔料から選ばれる少なくとも2種以上の顔料を用いて黒色着色剤としてもよい。 Specifically, the black pigment is C.I. I. Pigment Black 1, 6, 7, 12, 20, 31 and the like. Alternatively, at least two or more pigments selected from red pigments, yellow pigments, blue pigments, green pigments, and violet pigments may be used as a black coloring agent.
顔料の中で無機顔料は、例えば、酸化チタン、硫酸バリウム、亜鉛華、硫酸鉛、黄色鉛、亜鉛黄、べんがら(赤色酸化鉄(iii))、カドミウム赤、群青、紺青、酸化クロム緑、コバルト緑、アンバー、合成鉄黒等が挙げられる。 Among the pigments, inorganic pigments include, for example, titanium oxide, barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron (III) oxide), cadmium red, ultramarine blue, deep blue, chromium oxide green, and cobalt. Examples include green, amber, and synthetic iron black.
(染料)
染料は、例えば、酸性染料、直接染料、塩基性染料、造塩染料、油溶性染料、分散染料、反応染料、媒染染料、建染染料、硫化染料等が挙げられる。また、これらの誘導体や、染料をレーキ化したレーキ顔料も挙げられる。
(dye)
Examples of the dye include acid dyes, direct dyes, basic dyes, salt-forming dyes, oil-soluble dyes, disperse dyes, reactive dyes, mordant dyes, vat dyes, and sulfur dyes. Also included are derivatives of these and lake pigments obtained by forming dyes into lakes.
酸性染料は、スルホン酸やカルボン酸等の酸性基を有することが好ましい。また、酸性染料と、四級アンモニウム塩化合物、三級アミン化合物、二級アミン化合物、または一級アミン化合物等の含窒素化合物との塩である造塩化合物が好ましい。また、これらの官能基を有する樹脂成分と酸性染料との塩である造塩化合物も好ましい。また、造塩化合物は、スルホンアミド化してスルホン酸アミド化合物に変性することで耐性(耐光性、耐溶剤性)に優れた感光性組成物を得やすい。
また、酸性染料とオニウム塩基を有する化合物との造塩化合物も、耐性(耐光性、溶剤耐性)に優れるため好ましい。なお、オニウム塩基を有する化合物は、カチオン性基を有する樹脂が好ましい。
It is preferable that the acidic dye has an acidic group such as sulfonic acid or carboxylic acid. Further, a salt-forming compound which is a salt of an acidic dye and a nitrogen-containing compound such as a quaternary ammonium salt compound, a tertiary amine compound, a secondary amine compound, or a primary amine compound is preferable. Also preferred are salt-forming compounds that are salts of resin components having these functional groups and acidic dyes. Further, by converting the salt-forming compound into a sulfonamide compound and modifying it into a sulfonic acid amide compound, a photosensitive composition with excellent resistance (light resistance, solvent resistance) can be easily obtained.
Further, a salt-forming compound of an acidic dye and a compound having an onium base is also preferable because it has excellent resistance (light resistance, solvent resistance). Note that the compound having an onium base is preferably a resin having a cationic group.
塩基性染料は、そのままでも使用できるが、有機酸や過塩素酸またはその金属塩と塩を形成する造塩化合物が好ましい。塩基性染料の造塩化合物は、耐性(耐光性、耐溶剤性)や、顔料との親和性が優れているため好ましい。また、塩基性染料の造塩化合物で、カウンタイオンとしてはたらくアニオン成分は、有機スルホン酸、有機硫酸、フッ素基含有リンアニオン化合物、フッ素基含有ホウ素アニオン化合物、シアノ基含有窒素アニオン化合物、ハロゲン化炭化水素基を有する有機酸の共役塩基を有するアニオン化合物、酸性染料とを造塩した造塩化合物が好ましい。なお、造塩化合物は、分子中に重合性不飽和基を含有すると耐性がより向上する。 Although the basic dye can be used as it is, it is preferably a salt-forming compound that forms a salt with an organic acid, perchloric acid, or a metal salt thereof. Salt-forming compounds of basic dyes are preferable because they have excellent resistance (light resistance, solvent resistance) and affinity with pigments. In addition, the anion components that act as counter ions in the salt-forming compounds of basic dyes include organic sulfonic acids, organic sulfuric acids, fluorine group-containing phosphorus anion compounds, fluorine group-containing boron anion compounds, cyano group-containing nitrogen anion compounds, and carbonized halides. Preferred are salt forming compounds obtained by forming salts with an anionic compound having a conjugate base of an organic acid having a hydrogen group and an acidic dye. Note that the resistance of the salt-forming compound is further improved when it contains a polymerizable unsaturated group in the molecule.
染料の化学構造は、例えば、アゾ系染料、ジスアゾ系染料、アゾメチン系染料(インドアニリン系染料、インドフェノール系染料など)、ジピロメテン系染料、キノン系染料(ベンゾキノン系染料、ナフトキノン系染料、アントラキノン系染料、アントラピリドン系染料など)、カルボニウム系染料(ジフェニルメタン系染料、トリフェニルメタン系染料、キサンテン系染料、アクリジン系染料など)、キノンイミン系染料(オキサジン系染料、チアジン系染料など)、アジン系染料、ポリメチン系染料(オキソノール系染料、メロシアニン系染料、アリーリデン系染料、スチリル系染料、シアニン系染料、スクアリリウム系染料、クロコニウム系染料など)、キノフタロン系染料、フタロシアニン系染料、サブフタロシアニン系染料、ペリノン系染料、インジゴ系染料、チオインジゴ系染料、キノリン系染料、ニトロ系染料、ニトロソ系染料、ローダミン系染料、及びそれらの金属錯体系染料等から選ばれる染料に由来する色素構造が挙げられる。 The chemical structures of dyes include, for example, azo dyes, disazo dyes, azomethine dyes (indoaniline dyes, indophenol dyes, etc.), dipyrromethene dyes, quinone dyes (benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, etc.). dyes, anthrapyridone dyes, etc.), carbonium dyes (diphenylmethane dyes, triphenylmethane dyes, xanthene dyes, acridine dyes, etc.), quinone imine dyes (oxazine dyes, thiazine dyes, etc.), azine dyes , polymethine dyes (oxonol dyes, merocyanine dyes, arylidene dyes, styryl dyes, cyanine dyes, squarylium dyes, croconium dyes, etc.), quinophthalone dyes, phthalocyanine dyes, subphthalocyanine dyes, perinone dyes Examples include dye structures derived from dyes selected from dyes, indigo dyes, thioindigo dyes, quinoline dyes, nitro dyes, nitroso dyes, rhodamine dyes, and metal complex dyes thereof.
これらの中でも、色相、色分離性、色むらなどの色特性の観点から、アゾ系染料、キサンテン系染料、シアニン系染料、トリフェニルメタン系染料、アントラキノン系染料、ジピロメテン系染料、スクアリリウム系染料、キノフタロン系染料、フタロシアニン系染料、サブフタロシアニン系染料から選ばれる色素に由来する色素構造が好ましく、キサンテン系染料、シアニン系染料、トリフェニルメタン系染料、アントラキノン系染料、ジピロメテン系染料、フタロシアニン系染料から選ばれる色素に由来する色素構造がより好ましい。 Among these, from the viewpoint of color characteristics such as hue, color separation, and color unevenness, azo dyes, xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, squarylium dyes, A dye structure derived from a dye selected from quinophthalone dyes, phthalocyanine dyes, and subphthalocyanine dyes is preferable, and dyes derived from xanthene dyes, cyanine dyes, triphenylmethane dyes, anthraquinone dyes, dipyrromethene dyes, and phthalocyanine dyes are preferred. A dye structure derived from the selected dye is more preferred.
着色剤(E)は、単独、または2種類以上を併用して使用することができる。 The colorant (E) can be used alone or in combination of two or more.
着色剤(E)の含有量は、感光性組成物の不揮発分100質量%中、5~70質量%が好ましく、10~60質量%がより好ましい。 The content of the colorant (E) is preferably 5 to 70% by weight, more preferably 10 to 60% by weight based on 100% by weight of the nonvolatile content of the photosensitive composition.
(顔料の微細化)
顔料は、微細化して用いることが好ましい。微細化方法は、特に限定されるものではなく、例えば、湿式磨砕、乾式磨砕、溶解析出法いずれも使用できる。これらの中でも、湿式磨砕の1種であるニーダー法によるソルトミリング処理が好ましい。微細化顔料のTEM(透過型電子顕微鏡)により求められる平均一次粒子径は、5~90nmが好ましい。なお、分散性、コントラスト比の観点から、平均一次粒子径は10~70nmがより好ましい。
(Refining of pigment)
It is preferable to use the pigment in a finely divided form. The refinement method is not particularly limited, and, for example, any of wet grinding, dry grinding, and solution precipitation methods can be used. Among these, salt milling treatment using a kneader method, which is a type of wet milling, is preferred. The average primary particle diameter of the finely divided pigment determined by TEM (transmission electron microscope) is preferably 5 to 90 nm. Note that from the viewpoint of dispersibility and contrast ratio, the average primary particle diameter is more preferably 10 to 70 nm.
ソルトミリング処理とは、顔料と水溶性無機塩と水溶性有機溶剤との混合物を、ニーダー、2本ロールミル、3本ロールミル、ボールミル、アトライター、サンドミル等の混練機を用いて、加熱しながら機械的に混練した後、水洗により水溶性無機塩と水溶性有機溶剤を除去する処理である。水溶性無機塩は、破砕助剤として働くものであり、ソルトミリング時に無機塩の硬度の高さを利用して顔料が破砕される。顔料をソルトミリング処理する際の条件を最適化することにより、一次粒子径が非常に微細であり、また、分布の幅がせまく、シャープな粒度分布をもつ顔料を得ることができる。 Salt milling is a process in which a mixture of pigments, water-soluble inorganic salts, and water-soluble organic solvents is mechanically heated while being heated using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attriter, or sand mill. After kneading, water-soluble inorganic salts and water-soluble organic solvents are removed by washing with water. The water-soluble inorganic salt acts as a crushing aid, and the high hardness of the inorganic salt is used to crush the pigment during salt milling. By optimizing the conditions for salt milling pigments, it is possible to obtain pigments with very fine primary particle diameters, narrow distribution widths, and sharp particle size distributions.
水溶性無機塩は、塩化ナトリウム、塩化カリウム、硫酸ナトリウム等が挙げられる。水溶性無機塩は、価格の点から塩化ナトリウム(食塩)が好ましい。水溶性無機塩の使用量は、処理効率と生産効率の両面から、顔料100質量部に対して、50~2,000質量部が好ましく、300~1,000質量部がより好ましい。 Examples of water-soluble inorganic salts include sodium chloride, potassium chloride, and sodium sulfate. The water-soluble inorganic salt is preferably sodium chloride (salt) from the viewpoint of cost. The amount of water-soluble inorganic salt used is preferably 50 to 2,000 parts by weight, more preferably 300 to 1,000 parts by weight, based on 100 parts by weight of the pigment, from the viewpoint of both processing efficiency and production efficiency.
水溶性有機溶剤は、顔料および水溶性無機塩を湿潤する働きをするものであり、水に溶解(混和)し、かつ用いる無機塩を実質的に溶解しない溶剤である。ただし、ソルトミリング時に温度が上昇し、溶剤が蒸発し易い状態になるため、安全性の点から、沸点120℃以上の高沸点溶剤が好ましい。例えば、2-メトキシエタノール、2-ブトキシエタノール、2-(イソペンチルオキシ)エタノール、2-(ヘキシルオキシ)エタノール、ジエチレングリコール、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコール、トリエチレングリコールモノメチルエーテル、液状のポリエチレングリコール、1-メトキシ-2-プロパノール、1-エトキシ-2-プロパノール、ジプロピレングリコール、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、液状のポリプロピレングリコール等が用いられる。水溶性有機溶剤の使用量は、顔料100質量部に対して、5~1,000質量部が好ましく、50~500質量部がより好ましい。 The water-soluble organic solvent functions to wet the pigment and the water-soluble inorganic salt, and is a solvent that dissolves (mixes with) water but does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent is likely to evaporate, a high boiling point solvent with a boiling point of 120° C. or higher is preferred from the viewpoint of safety. For example, 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, Liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. are used. The amount of the water-soluble organic solvent used is preferably 5 to 1,000 parts by weight, more preferably 50 to 500 parts by weight, per 100 parts by weight of the pigment.
ソルトミリング処理には、必要に応じて樹脂を添加してもよい。前記樹脂の種類は特に限定されず、天然樹脂、変性天然樹脂、合成樹脂、天然樹脂で変性された合成樹脂等が挙げられる。これらの中でも、室温で固体であり、水不溶性であることが好ましく、かつ上記有機溶剤に一部可溶であることが好ましい。樹脂の添加量は、顔料100質量部に対して、2~200質量部が好ましい。 A resin may be added to the salt milling treatment if necessary. The type of resin is not particularly limited, and examples include natural resins, modified natural resins, synthetic resins, and synthetic resins modified with natural resins. Among these, it is preferably solid at room temperature, insoluble in water, and partially soluble in the above organic solvent. The amount of resin added is preferably 2 to 200 parts by weight per 100 parts by weight of the pigment.
[色素誘導体(F)]
本発明の感光組成物は、色素誘導体(F)を含有できる。
[Dye derivative (F)]
The photosensitive composition of the present invention can contain a dye derivative (F).
色素誘導体(F)は、有機色素残基に酸性基、塩基性基、中性基などを有する化合物である。色素誘導体(F)は、例えば、スルホ基、カルボキシ基、リン酸基などの酸性置換基を有する化合物、およびこれらのアミン塩や、スルホンアミド基や末端に3級アミノ基などの塩基性置換基を有する化合物、フェニル基やフタルイミドアルキル基などの中性置換基を有する化合物が挙げられる。
有機色素は、例えばジケトピロロピロール系顔料、アントラキノン系顔料、キナクリドン系顔料、ジオキサジン系顔料、ペリノン系顔料、ペリレン系顔料、チアジンインジゴ系顔料、トリアジン系顔料、ベンズイミダゾロン系顔料、ベンゾイソインドール等のインドール系顔料、イソインドリン系顔料、イソインドリノン系顔料、キノフタロン系顔料、ナフトール系顔料、スレン系顔料、金属錯体系顔料、アゾ、ジスアゾ、ポリアゾ等のアゾ系顔料等が挙げられる。
The dye derivative (F) is a compound having an acidic group, a basic group, a neutral group, etc. in the organic dye residue. The dye derivative (F) is, for example, a compound having an acidic substituent such as a sulfo group, a carboxy group, or a phosphoric acid group, or an amine salt thereof, or a basic substituent such as a sulfonamide group or a tertiary amino group at the terminal. Examples include compounds having a neutral substituent such as a phenyl group or a phthalimido alkyl group.
Examples of organic pigments include diketopyrrolopyrrole pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thiazine indigo pigments, triazine pigments, benzimidazolone pigments, and benzoisomer pigments. Examples include indole pigments such as indole, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, naphthol pigments, threne pigments, metal complex pigments, and azo pigments such as azo, disazo, and polyazo.
具体的には、ジケトピロロピロール系色素誘導体としては、特開2001-220520号公報、国際公開第2009/081930号、国際公開第2011/052617号、国際公開第2012/102399号、特開2017-156397号公報、フタロシアニン系色素誘導体としては、特開2007-226161号公報、国際公開第2016/163351号、特開2017-165820号公報、特許第5753266号公報、アントラキノン系色素誘導体としては、特開昭63-264674号公報、特開平09-272812号公報、特開平10-245501号公報、特開平10-265697号公報、特開2007-079094号公報、国際公開第2009/025325号、キナクリドン系色素誘導体としては、特開昭48-54128号公報、特開平03-9961号公報、特開2000-273383号公報、ジオキサジン系色素誘導体としては、特開2
011-162662号公報、チアジンインジゴ系色素誘導体としては、特開2007-314785号公報、トリアジン系色素誘導体としては、特開昭61-246261号公報、特開平11-199796号公報、特開2003-165922号公報、特開2003-168208号公報、特開2004-217842号公報、特開2007-314681号公報、ベンゾイソインドール系色素誘導体としては、特開2009-57478号公報、キノフタロン系色素誘導体としては、特開2003-167112号公報、特開2006-291194号公報、特開2008-31281号公報、特開2012-226110号公報、ナフトール系色素誘導体としては、特開2012-208329号公報、特開2014-5439号公報、アゾ系色素誘導体としては、特開2001-172520号公報、特開2012-172092号公報、酸性置換基としては、特開2004-307854号公報、塩基性置換基としては、特開2002-201377号公報、特開2003-171594号公報、特開2005-181383号公報、特開2005-213404号公報等に記載の公知の色素誘導体が挙げられる。なお、これらの文献には、色素誘導体を誘導体、顔料誘導体、分散剤、顔料分散剤若しくは単に化合物などと記載している場合があるが、前記した有機色素残基に酸性基、塩基性基、中性基などの置換基を有する化合物は、色素誘導体と同義である。
Specifically, as diketopyrrolopyrrole dye derivatives, JP 2001-220520 A, WO 2009/081930, WO 2011/052617, WO 2012/102399, JP 2017 -156397, as phthalocyanine dye derivatives, JP 2007-226161, WO 2016/163351, JP 2017-165820, and Japanese Patent No. 5753266, as anthraquinone dye derivatives, JP-A-63-264674, JP-A-09-272812, JP-A-10-245501, JP-A-10-265697, JP-A-2007-079094, International Publication No. 2009/025325, Quinacridone series Examples of dye derivatives include JP-A-48-54128, JP-A-03-9961, and JP-A-2000-273383, and dioxazine-based dye derivatives include JP-A-2
011-162662, thiazine indigo dye derivatives, JP 2007-314785, triazine dye derivatives, JP 61-246261, JP 11-199796, JP 2003 -165922, JP 2003-168208, JP 2004-217842, JP 2007-314681, as benzisoindole dye derivatives, JP 2009-57478, quinophthalone dye derivatives. As for the naphthol dye derivative, JP 2003-167112, JP 2006-291194, JP 2008-31281, JP 2012-226110, and naphthol dye derivatives include JP 2012-208329, JP 2014-5439, Azo dye derivatives, JP 2001-172520, JP 2012-172092, acidic substituents, JP 2004-307854, basic substituents Examples include known dye derivatives described in JP-A No. 2002-201377, JP-A No. 2003-171594, JP-A No. 2005-181383, and JP-A No. 2005-213404. In addition, in these documents, the dye derivative is sometimes described as a derivative, a pigment derivative, a dispersant, a pigment dispersant, or simply a compound. A compound having a substituent such as a neutral group has the same meaning as a dye derivative.
色素誘導体(F)は、単独または2種類以上を併用して使用できる。 The dye derivative (F) can be used alone or in combination of two or more types.
色素誘導体(F)の含有量は、着色剤(E)100質量部に対して、1~20質量部が好ましく、2~10質量部がより好ましい。 The content of the dye derivative (F) is preferably 1 to 20 parts by weight, more preferably 2 to 10 parts by weight, based on 100 parts by weight of the colorant (E).
[分散樹脂(G)]
本発明の感光性組成物は、分散樹脂(G)を含有できる。
[Dispersion resin (G)]
The photosensitive composition of the present invention can contain a dispersion resin (G).
分散樹脂(G)は、着色剤(E)に親和性が高い吸着基を有している樹脂が好ましい。吸着基は、塩基性基、および酸性基のうち1種以上有していることが好ましく、現像性の観点から、酸性基を有することが好ましい。 The dispersion resin (G) is preferably a resin having an adsorption group with high affinity for the colorant (E). It is preferable that the adsorption group has at least one kind of a basic group and an acidic group, and from the viewpoint of developability, it is preferable that the adsorption group has an acidic group.
塩基性基は、例えば、1級アミノ基、2級アミノ基、3級アミノ基、4級アンモニア塩基、および含窒素複素環など窒素原子を含有する基等が挙げられる。 Examples of the basic group include a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonia base, and a nitrogen atom-containing group such as a nitrogen-containing heterocycle.
酸性基は、例えば、カルボキシル基、リン酸基、スルホン酸基等が挙げられる。これらの中でも、顔料への吸着性、現像性の観点からカルボキシル基、リン酸基が好ましい。 Examples of acidic groups include carboxyl groups, phosphoric acid groups, and sulfonic acid groups. Among these, carboxyl groups and phosphoric acid groups are preferred from the viewpoint of adsorption to pigments and developability.
分散樹脂(G)の樹脂種は、例えば、ウレタン樹脂、ポリアクリレート等のポリカルボン酸エステル、不飽和ポリアミド、ポリカルボン酸、ポリカルボン酸(部分)アミン塩、ポリカルボン酸アンモニウム塩、ポリカルボン酸アルキルアミン塩、ポリシロキサン、長鎖ポリアミノアマイドリン酸塩、水酸基含有ポリカルボン酸エステルや、これらの変性物、ポリ(低級アルキレンイミン)と遊離のカルボキシル基を有するポリエステルとの反応により形成されたアミドやその塩等、(メタ)アクリル酸-スチレン共重合体、(メタ)アクリル酸-(メタ)アクリル酸エステル共重合体、スチレン-マレイン酸共重合体、ポリビニルアルコ-ル、ポリビニルピロリドン等の水溶性樹脂や水溶性高分子化合物、ポリエステル系、変性ポリアクリレート系、エチレンオキサイド/プロピレンオキサイド付加化合物、リン酸エステル系等が挙げられる。 The resin species of the dispersion resin (G) include, for example, urethane resins, polycarboxylic acid esters such as polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acids. Alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, modified products thereof, and amides formed by the reaction of poly(lower alkylene imine) with polyesters having free carboxyl groups. Water-soluble products such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc. Examples include water-soluble resins, water-soluble polymer compounds, polyesters, modified polyacrylates, ethylene oxide/propylene oxide adducts, phosphate esters, and the like.
分散樹脂(G)の構造は、例えば、ランダム構造、ブロック構造、グラフト構造、くし型構造、および星型構造等が挙げられる。これらの中でも、分散安定性の観点から、ブロック構造、またはくし型構造が好ましい。 Examples of the structure of the dispersed resin (G) include a random structure, a block structure, a graft structure, a comb structure, and a star structure. Among these, a block structure or a comb structure is preferred from the viewpoint of dispersion stability.
分散樹脂(G)の市販品は、例えば、ビックケミー・ジャパン社製のDisperbyk-101,103,107,108,110,111,116,130,140,154,161,162,163,164,165,166,167,168,170,171,174,180,181,182,183,184,185,190,2000,2001,2009,2010,2020,2025,2050,2070,2095,2150,2155,2163,2164、またはAnti-Terra-U203,204、またはBYK-P104,P104S,220S、またはLactimon、Lactimon-WS、またはBykumen等、日本ルーブリゾール社製のSOLSPERSE-3000,9000,13000,13240,13650,13940,16000,17000,18000,20000,21000,24000,26000,27000,28000,31845,32000,32500,32550,33500,32600,34750,35100,36600,38500,41000,41090,53095,55000,56000,76500等、BASFジャパン社製のEFKA-46,47,48,452,4008,4009,4010,4015,4020,4047,4050,4055,4060,4080,4400,4401,4402,4403,4406,4408,4300,4310,4320,4330,4340,450,451,453,4540,4550,4560,4800,5010,5065,5066,5070,7500,7554,1101,120,150,1501,1502,1503等、味の素ファインテクノ社製のアジスーパーPA111,PB711,PB821,PB822,PB824等、特開2008-029901号公報、特開2009-155406号公報、特開2010-185934号公報、特開2011-157416号公報、国際公開2008/007776号、特開2008-029901号公報、特開2009-155406号公報、特開2010-185934号公報、特開2011-157416号公報、特開2009-251481号公報、特開2007-23195号公報、特開1996-143651号公報等に記載の樹脂が挙げられる。 Commercially available products of the dispersion resin (G) include, for example, Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, manufactured by BYK Chemie Japan Co., Ltd. 166, 167, 168, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2009, 2010, 2020, 2025, 2050, 2070, 2095, 2150, 2155, 2163, 2164, or Anti-Terra-U203, 204, or BYK-P104, P104S, 220S, or Lactimon, Lactimon-WS, or Bykumen, SOLSPERSE-3000, 9000, 13000, 13240, 136 manufactured by Japan Lubrizol Co., Ltd. 50,13940 ,16000,17000,18000,20000,21000,24000,26000,27000,28000,31845,32000,32500,32550,33500,32600,34750,35100,36600,38500,41000, 41090, 53095, 55000, 56000, 76500 etc., EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300 manufactured by BASF Japan. , 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., Ajinomoto Fine Ajisuper PA111, PB711, PB821, PB822, PB824, etc. manufactured by Techno Co., Ltd., JP 2008-029901, JP 2009-155406, JP 2010-185934, JP 2011-157416, International Publication No. 2008/007776, JP 2008-029901, JP 2009-155406, JP 2010-185934, JP 2011-157416, JP 2009-251481, JP 2007- Examples include resins described in JP-A No. 23195, JP-A No. 1996-143651, and the like.
分散樹脂(G)は、単独または2種類以上を併用して使用できる。 The dispersion resin (G) can be used alone or in combination of two or more types.
分散樹脂(G)の含有量は、分散安定性の観点から、着色剤(E)100質量部に対して、3~200質量部が好ましく、5~100質量部がより好ましい。 From the viewpoint of dispersion stability, the content of the dispersion resin (G) is preferably 3 to 200 parts by weight, more preferably 5 to 100 parts by weight, based on 100 parts by weight of the colorant (E).
[増感剤(H)]
本発明の感光性組成物は、増感剤(H)を含有できる。
[Sensitizer (H)]
The photosensitive composition of the present invention can contain a sensitizer (H).
増感剤(H)は、例えば、カルコン誘導体、ジベンザルアセトン等に代表される不飽和ケトン類、ベンジルやカンファーキノン等に代表される1,2-ジケトン誘導体、ベンゾイン誘導体、フルオレン誘導体、ナフトキノン誘導体、アントラキノン誘導体、キサンテン誘導体、チオキサンテン誘導体、キサントン誘導体、チオキサントン誘導体、クマリン誘導体、ケトクマリン誘導体、シアニン誘導体、メロシアニン誘導体、オキソノール誘導体等のポリメチン色素、アクリジン誘導体、アジン誘導体、チアジン誘導体、オキサジン誘導体、インドリン誘導体、アズレン誘導体、アズレニウム誘導体、スクアリリウム誘導体、ポルフィリン誘導体、テトラフェニルポルフィリン誘導体、トリアリールメタン誘導体、テトラベンゾポルフィリン誘導体、テトラピラジノポルフィラジン誘導体、フタロシアニン誘導体、テトラアザポルフィラジン誘導体、テトラキノキサリロポルフィラジン誘導体、ナフタロシアニン誘導体、サブフタロシアニン誘導体、ピリリウム誘導体、チオピリリウム誘導体、テトラフィリン誘導体、アヌレン誘導体、スピロピラン誘導体、スピロオキサジン誘導体、チオスピロピラン誘導体、金属アレーン錯体、有機ルテニウム錯体、又はミヒラーケトン誘導体、α-アシロキシエステル、アシルオキサイド、メチルフェニルグリオキシレート、ベンジル、9,10-フェナンスレンキノン、カンファーキノン、エチルアンスラキノン、4,4’-ジエチルイソフタロフェノーン、3,3’又は4,4
’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノン、4,4’-ビス(ジエチルアミノ)ベンゾフェノン等が挙げられる。
Examples of the sensitizer (H) include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, and naphthoquinone. Derivatives, anthraquinone derivatives, xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, polymethine dyes such as oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrin derivatives Radin derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine derivatives, thiospiropyran derivatives, metal arene complexes, organic ruthenium complexes, or Michler ketone derivatives, α- Siloxy ester, acyl oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl anthraquinone, 4,4'-diethylisophthalophenone, 3,3' or 4,4
Examples include '-tetra(t-butylperoxycarbonyl)benzophenone and 4,4'-bis(diethylamino)benzophenone.
増感剤(H)の中で、チオキサントン誘導体、ミヒラーケトン誘導体、カルバゾール誘導体が好ましい。具体的な化合物は、2,4-ジエチルチオキサントン、2-クロロチオキサントン、2,4-ジクロロチオキサントン、2-イソプロピルチオキサントン、4-イソプロピルチオキサントン、1-クロロ-4-プロポキシチオキサントン、4,4’-ビス(ジメチルアミノ)ベンゾフェノン、4,4’-ビス(ジエチルアミノ)ベンゾフェノン、4,4’-ビス(エチルメチルアミノ)ベンゾフェノン、N-エチルカルバゾール、3-ベンゾイル-N-エチルカルバゾール、3,6-ジベンゾイル-N-エチルカルバゾール等が好ましい。 Among the sensitizers (H), thioxanthone derivatives, Michler's ketone derivatives, and carbazole derivatives are preferred. Specific compounds include 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propoxythioxanthone, 4,4'-bis (dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, N-ethylcarbazole, 3-benzoyl-N-ethylcarbazole, 3,6-dibenzoyl- N-ethylcarbazole and the like are preferred.
増感剤(H)は、単独または2種類以上を併用して使用できる。 The sensitizer (H) can be used alone or in combination of two or more.
増感剤(H)の含有量は、光重合開始剤(C)100質量部に対して、3~60質量部が好ましく、5~50質量部がより好ましい。適量含有すると光硬化性、現像性が向上する。 The content of the sensitizer (H) is preferably 3 to 60 parts by weight, more preferably 5 to 50 parts by weight, based on 100 parts by weight of the photopolymerization initiator (C). Containing an appropriate amount improves photocurability and developability.
[熱硬化性化合物(I)]
本発明の感光性組成物は、熱硬化性化合物(I)を含有できる。これにより、加熱工程で熱硬化性化合物(I)が反応し、架橋密度が高まるため耐熱性が向上する。
[Thermosetting compound (I)]
The photosensitive composition of the present invention can contain a thermosetting compound (I). As a result, the thermosetting compound (I) reacts in the heating step, increasing the crosslinking density and improving heat resistance.
熱硬化性化合物(I)は、低分子化合物や、樹脂のような高分子量化合物でもよい。熱硬化性化合物(i)は、例えば、エポキシ化合物、オキセタン化合物、ベンゾグアナミン化合物、ロジン変性マレイン酸化合物、ロジン変性フマル酸化合物、メラミン化合物、尿素化合物、及びフェノール化合物が挙げられる。これらの中でもエポキシ化合物およびオキセタン化合物が好ましい。 The thermosetting compound (I) may be a low molecular weight compound or a high molecular weight compound such as a resin. Examples of the thermosetting compound (i) include epoxy compounds, oxetane compounds, benzoguanamine compounds, rosin-modified maleic acid compounds, rosin-modified fumaric acid compounds, melamine compounds, urea compounds, and phenol compounds. Among these, epoxy compounds and oxetane compounds are preferred.
(エポキシ化合物(I1))
エポキシ化合物(I1)は、例えば、ビスフェノール類(ビスフェノールA、ビスフェノールF、ビスフェノールS、ビフェノール、ビスフェノールAD等)、フェノール類(フェノール、アルキル置換フェノール、芳香族置換フェノール、ナフトール、アルキル置換ナフトール、ジヒドロキシベンゼン、アルキル置換ジヒドロキシベンゼン、ジヒドロキシナフタレン等)と各種アルデヒド(ホルムアルデヒド、アセトアルデヒド、アルキルアルデヒド、ベンズアルデヒド、アルキル置換ベンズアルデヒド、ヒドロキシベンズアルデヒド、ナフトアルデヒド、グルタルアルデヒド、フタルアルデヒド、クロトンアルデヒド、シンナムアルデヒド等)との重縮合物、フェノール類と各種ジエン化合物(ジシクロペンタジエン、テルペン類、ビニルシクロヘキセン、ノールボルナジエン、ビニルノールボルネン、テトラヒドロインデン、ジビニルベンゼン、ジビニルビフェニル、ジイソプロペニルビフェニル、ブタジエン、イソプレン等)との重合物、フェノール類とケトン類(アセトン、メチルエチルケトン、メチルイソブチルケトン、アセトフェノン、ベンゾフェノン等)との重縮合物、フェノール類と芳香族ジメタノール類(ベンゼンジメタノール、α,α,α’,α’-ベンゼンジメタノール、ビフェニルジメタノール、α,α,α’,α’-ビフェニルジメタノール等)との重縮合物、フェノール類と芳香族ジクロロメチル類(α,α’-ジクロロキシレン、ビスクロロメチルビフェニル等)との重縮合物、ビスフェノール類と各種アルデヒドの重縮合物、アルコール類等をグリシジル化したグリシジルエーテル系エポキシ樹脂、脂環式エポキシ樹脂、複素環式エポキシ樹脂、脂肪族エポキシ樹脂、グリシジルアミン系エポキシ樹脂、グリシジルエステル系エポキシ樹脂等が挙げられる。
(Epoxy compound (I1))
Epoxy compounds (I1) include, for example, bisphenols (bisphenol A, bisphenol F, bisphenol S, biphenol, bisphenol AD, etc.), phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene). , alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) and various aldehydes (formaldehyde, acetaldehyde, alkyl aldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.). Polymerization of compounds, phenols, and various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, isoprene, etc.) polycondensates of phenols and ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.), phenols and aromatic dimethanols (benzenedimethanol, α, α, α', α'- benzene dimethanol, biphenyl dimethanol, α, α, α', α'-biphenyl dimethanol, etc.), polycondensates of phenols and aromatic dichloromethyls (α, α'-dichloroxylene, bischloromethyl biphenyl, etc.) etc.), polycondensates of bisphenols and various aldehydes, glycidyl ether epoxy resins obtained by glycidylating alcohols, etc., alicyclic epoxy resins, heterocyclic epoxy resins, aliphatic epoxy resins, glycidyl amines. Examples include glycidyl ester-based epoxy resins and glycidyl ester-based epoxy resins.
市販品は、例えば、油化シェルエポキシ社製のエピコート807,815,825,827,828,190P,191P、三井化学社製のTECHMORE VG3101L、日本化薬社製のEPPN-201,501H,502H、EOCN-102S,103S,104S,1020ジャパンエポキシレジン社製のエピコート1004,1256、JER1032H60,157S65,157S70,152,154、ダイセル化学工業社製のセロキサイド2021、EHPE-3150、ナガセケムテックス社製のデナコールEX-211,212,252,313,314,321,411,421,512,521,611,612,614,614B,622,711,721、日産化学工業社製のTEPIC-L,H,S等が挙げられる。 Commercially available products include, for example, Epicoat 807, 815, 825, 827, 828, 190P, 191P manufactured by Yuka Shell Epoxy Co., Ltd., TECHMORE VG3101L manufactured by Mitsui Chemicals, EPPN-201, 501H, 502H manufactured by Nippon Kayaku Co., Ltd. EOCN-102S, 103S, 104S, 1020 Epicote 1004, 1256 manufactured by Japan Epoxy Resin Co., Ltd., JER1032H60, 157S65, 157S70, 152, 154, Celoxide 2021 manufactured by Daicel Chemical Industries, EHPE-3150, Denacol manufactured by Nagase ChemteX EX-211, 212, 252, 313, 314, 321, 411, 421, 512, 521, 611, 612, 614, 614B, 622, 711, 721, TEPIC-L, H, S, etc. manufactured by Nissan Chemical Industries, Ltd. can be mentioned.
エポキシ化合物(I1)の含有量は、硬化膜の耐熱性の観点から、感光性組成物の不揮発分100質量%中、0.5~50質量%が好ましく、1~40質量%がより好ましい。 From the viewpoint of heat resistance of the cured film, the content of the epoxy compound (I1) is preferably 0.5 to 50% by mass, more preferably 1 to 40% by mass based on 100% by mass of the nonvolatile content of the photosensitive composition.
(オキセタン化合物(I2))
オキセタン化合物(iI2)は、オキセタン基を有する公知の化合物である。オキセタン化合物は、1官能オキセタン化合物、2官能オキセタン化合物、3官能以上のオキセタン化合物が挙げられる。
(Oxetane compound (I2))
The oxetane compound (iI2) is a known compound having an oxetane group. Examples of the oxetane compound include monofunctional oxetane compounds, bifunctional oxetane compounds, and trifunctional or more functional oxetane compounds.
1官能オキセタン化合物は、例えば、(3-エチルオキセタン-3-イル)メチルアクリレート、 (3-エチルオキセタン-3-イル)メチルメタクリレート、3-エチル-3-
ヒドロキシメチルオキセタン、3-エチル-3-(2-エチルヘキシロキシメチル)オキセタン、3-エチル-3-(フェノキシメチル)オキセタン、3-エチル-3-(2-メタクリロキシメチル)オキセタン、3-エチル-3-{[3-(トリエトキシシリル)プロポキシ]メチル}オキセタン等が挙げられる。
Examples of monofunctional oxetane compounds include (3-ethyloxetan-3-yl)methyl acrylate, (3-ethyloxetan-3-yl)methyl methacrylate, and 3-ethyl-3-yl.
Hydroxymethyloxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(phenoxymethyl)oxetane, 3-ethyl-3-(2-methacryloxymethyl)oxetane, 3-ethyl -3-{[3-(triethoxysilyl)propoxy]methyl}oxetane and the like.
市販品は、例えば、大阪有機化学工業社製のOXE-10,30、東亞合成社製のOXT-101,212等が挙げられる。 Commercially available products include, for example, OXE-10,30 manufactured by Osaka Organic Chemical Industry Co., Ltd. and OXT-101,212 manufactured by Toagosei Co., Ltd.
2官能オキセタン化合物は、例えば、4,4’-ビス[(3-エチル-3-オキセタニル)メトキシメチル]ビフェニル)、1,4-ビス[(3-エチル-3-オキセタニル)メトキシメチル]ベンゼン、1,4-ビス{[(3-エチル-3-オキセタニル)メトキシ]メチル}ベンゼン、ジ[1-エチル(3-オキセタニル)]メチルエーテル、ジ[1-エチル(3-オキセタニル)]メチルエーテル3-エチル-3-ヒドロキシメチルオキセタン、3-エチル-3-(2-エチルヘキシロキシメチル)オキセタン、3-エチル-3-(2-フェノキシメチル)オキセタン、3,7-ビス(3-オキセタニル)-5-オキサ-ノナン、1,2-ビス[(3-エチル-3-オキセタニルメトキシ)メチル]エタン、1,3-ビス[(3-エチル-3-オキセタニルメトキシ)メチル]プロパン、エチレングリコ-スビス(3-エチル-3-オキセタニルメチル)エーテル、ジシクロペンテニルビス(3-エチル-3-オキセタニルメチル)エーテル、トリエチレングリコールビス(3-エチル-3-オキセタニルメチル)エーテル、テトラエチレングリコールビス(3-エチル-3-オキセタニルメチル)エーテル、1,4-ビス(3-エチル-3-オキセタニルメトキシ)ブタン、1,6-ビス(3-エチル-3-オキセタニルメトキシ)ヘキサン、ポリエチレングリコールビス(3-エチル-3-オキセタニルメチル)エーテル、エチレンオキシド(EO)変性ビスフェノールAビス(3-エチル-3-オキセタニルメチル)エーテル、プロピレンオキシド(PO)変性ビスフェノールAビス(3-エチル-3-オキセタニルメチル)エーテル、EO変性水添ビスフェノールAビス(3-エチル-3-オキセタニルメチル)エーテル、PO変性水添ビスフェノールAビス(3-エチル-3-オキセタニルメチル)エーテル、EO変性ビスフェノールF(3-エチル-3-オキセタニルメチル)エーテル等が挙げられる。 Bifunctional oxetane compounds include, for example, 4,4'-bis[(3-ethyl-3-oxetanyl)methoxymethyl]biphenyl), 1,4-bis[(3-ethyl-3-oxetanyl)methoxymethyl]benzene, 1,4-bis{[(3-ethyl-3-oxetanyl)methoxy]methyl}benzene, di[1-ethyl(3-oxetanyl)]methyl ether, di[1-ethyl(3-oxetanyl)]methyl ether 3 -Ethyl-3-hydroxymethyloxetane, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, 3-ethyl-3-(2-phenoxymethyl)oxetane, 3,7-bis(3-oxetanyl)- 5-Oxanonan, 1,2-bis[(3-ethyl-3-oxetanylmethoxy)methyl]ethane, 1,3-bis[(3-ethyl-3-oxetanylmethoxy)methyl]propane, ethylene glycose bis (3-ethyl-3-oxetanylmethyl) ether, dicyclopentenyl bis(3-ethyl-3-oxetanylmethyl) ether, triethylene glycol bis(3-ethyl-3-oxetanylmethyl) ether, tetraethylene glycol bis(3 -ethyl-3-oxetanylmethyl) ether, 1,4-bis(3-ethyl-3-oxetanylmethoxy)butane, 1,6-bis(3-ethyl-3-oxetanylmethoxy)hexane, polyethylene glycol bis(3- ethyl-3-oxetanylmethyl) ether, ethylene oxide (EO) modified bisphenol A bis(3-ethyl-3-oxetanylmethyl) ether, propylene oxide (PO) modified bisphenol A bis(3-ethyl-3-oxetanylmethyl) ether, EO-modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl) ether, PO-modified hydrogenated bisphenol A bis(3-ethyl-3-oxetanylmethyl) ether, EO-modified hydrogenated bisphenol F (3-ethyl-3-oxetanyl) Methyl) ether and the like.
市販品は、例えば、宇部興産社製のOXBP、OXTP、東亞合成社製のOXT-121,221等が挙げられる。 Commercially available products include, for example, OXBP and OXTP manufactured by Ube Industries, Ltd., and OXT-121 and 221 manufactured by Toagosei Co., Ltd.
3官能以上のオキセタン化合物は、例えば、ペンタエリスリトールトリス(3-エチル-3-オキセタニルメチル)エーテル、ペンタエリスリトールテトラキス(3-エチル-3-オキセタニルメチル)エーテル、ジペンタエリスリトールヘキサ(3-エチル-3-オキセタニルメチル)エーテル、ジペンタエリスリトールペンタキス(3-エチル-3-オキセタニルメチル)エーテル、ジペンタエリスリトールテトラキス(3-エチル-3-オキセタニルメチル)エーテル、カプロラクトン変性ジペンタエリスリトールヘキサ(3-エチル-3-オキセタニルメチル)エーテル、カプロラクトン変性ジペンタエリスリトールペンタキス(3-エチル-3-オキセタニルメチル)エーテル、ジトリメチロ-ルプロパンテトラキス(3-エチル-3-オキセタニルメチル)エーテル、オキセタン基を含有する樹脂(例えば、特許第3783462号記載のオキセタン変性フェノールノボラック樹脂等)や前述のOXE-30のような(メタ)アクリルモノマーをラジカル重合させて得られる重合体が挙げられる。 Trifunctional or higher functional oxetane compounds include, for example, pentaerythritol tris(3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis(3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol hexa(3-ethyl-3 -oxetanylmethyl) ether, dipentaerythritol pentakis (3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, caprolactone modified dipentaerythritol hexa(3-ethyl- 3-oxetanylmethyl) ether, caprolactone-modified dipentaerythritol pentakis (3-ethyl-3-oxetanylmethyl) ether, ditrimethylolpropane tetrakis (3-ethyl-3-oxetanylmethyl) ether, oxetane group-containing resin ( Examples include polymers obtained by radical polymerization of (meth)acrylic monomers such as oxetane-modified phenol novolac resin described in Japanese Patent No. 3783462) and the above-mentioned OXE-30.
オキセタン化合物(I2)の含有量は、感光性組成物の不揮発分100質量%中、0.5~50質量%が好ましく、1~40質量%がより好ましい。 The content of the oxetane compound (I2) is preferably 0.5 to 50% by weight, more preferably 1 to 40% by weight based on 100% by weight of the nonvolatile content of the photosensitive composition.
メラミン化合物は、メラミン環構造を有する化合物である。メラミン化合物は、メチロ-ル型やエーテル型の化合物が好ましく、メラミン環1個当たりのメチロ-ル基および/またはエーテル基数が平均5.0以上のメラミン化合物がより好ましい。適度にメチロ-ル基やエーテル基数を有すると過不足ない耐熱性が得やすい。 A melamine compound is a compound having a melamine ring structure. The melamine compound is preferably a methylol type or ether type compound, and more preferably a melamine compound having an average number of methylol groups and/or ether groups per melamine ring of 5.0 or more. Having an appropriate number of methylol groups or ether groups makes it easy to obtain just the right amount of heat resistance.
市販品は、例えば、三和ケミカル社製の二カラックMW-30HM,MW-390,MW-100LM,MX-750LM,MW-30M,MW-30,MW-22,MS-21,MS-11,MW-24X,MS-001,MX-002,MX-730,MX-750,MX-708,MX-706,MX-042,MX-45,MX-500,MX-520,MX-43,MX-417,MX-410、日本サイテックインダストリーズ社製のサイメル232,235,236,238,285,300,301,303,350,370等が挙げられる。 Commercially available products include, for example, Nikarak MW-30HM, MW-390, MW-100LM, MX-750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, manufactured by Sanwa Chemical Co., Ltd. MW-24X, MS-001, MX-002, MX-730, MX-750, MX-708, MX-706, MX-042, MX-45, MX-500, MX-520, MX-43, MX- 417, MX-410, and Cymel 232, 235, 236, 238, 285, 300, 301, 303, 350, and 370 manufactured by Nippon Cytec Industries.
これらの中でもメラミン環1個当たりのメチロ-ル基、及び/又は、エーテル基数が平均5.0以上である、三和ケミカル社製のニカラックMW-30HM、MW-390、MW-100LM、MX-750LM、MW-30M、MW-30、MW-22、MS-21、MS-11、MW-24X、MX-45、日本サイテックインダストリ-ズ社製のサイメル232,235,236,238,300,301,303,350等は、架橋密度を高められる面で好ましい。 Among these, Nikalac MW-30HM, MW-390, MW-100LM, and MX- manufactured by Sanwa Chemical Co., Ltd. have an average number of methylol groups and/or ether groups per melamine ring of 5.0 or more. 750LM, MW-30M, MW-30, MW-22, MS-21, MS-11, MW-24X, MX-45, Cymel 232, 235, 236, 238, 300 manufactured by Nihon Cytec Industries, 301, 303, 350, etc. are preferable in that they can increase the crosslinking density.
熱硬化性化合物(I)は、単独または2種類以上を併用して使用できる。 The thermosetting compound (I) can be used alone or in combination of two or more types.
[硬化剤(硬化促進剤)]
本発明の感光性組成物は、熱硬化性化合物(I)の硬化を補助するため、硬化剤(硬化促進剤)を併用できる。
[Curing agent (curing accelerator)]
The photosensitive composition of the present invention can be used in combination with a curing agent (curing accelerator) in order to assist in curing the thermosetting compound (I).
硬化剤は、例えば、アミン系化合物、酸無水物、活性エステル、カルボン酸系化合物、スルホン酸系化合物等が挙げられる。硬化剤は、例えば、アミン化合物(例えば、ジシアンジアミド、ベンジルジメチルアミン、4-(ジメチルアミノ)-N,N-ジメチルベンジルアミン、4-メトキシ-N,N-ジメチルベンジルアミン、4-メチル-N,N-ジメチルベンジルアミン等)、4級アンモニウム塩化合物(例えば、トリエチルベンジルアン
モニウムクロリド等)、ブロックイソシアネート化合物(例えば、ジメチルアミン等)、イミダゾール誘導体二環式アミジン化合物及びその塩(例えば、イミダゾール、2-メチルイミダゾール、2-エチルイミダゾール、2-エチル-4-メチルイミダゾール、2-フェニルイミダゾール、4-フェニルイミダゾール、1-シアノエチル-2-フェニルイミダゾール、1-(2-シアノエチル)-2-エチル-4-メチルイミダゾール等)、リン化合物(例えば、トリフェニルホスフィン等)、S-トリアジン誘導体(例えば、2,4-ジアミノ-6-メタクリロイルオキシエチル-S-トリアジン、2-ビニル-2,4-ジアミノ-S-トリアジン、2-ビニル-4,6-ジアミノ-S-トリアジン・イソシアヌル酸付加物、2,4-ジアミノ-6-メタクリロイルオキシエチル-S-トリアジン・イソシアヌル酸付加物等)等が挙げられる。
Examples of the curing agent include amine compounds, acid anhydrides, active esters, carboxylic acid compounds, and sulfonic acid compounds. The curing agent is, for example, an amine compound (for example, dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl-N, N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (e.g., triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (e.g., dimethylamine, etc.), imidazole derivatives, bicyclic amidine compounds and their salts (e.g., imidazole, -Methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4 -methylimidazole, etc.), phosphorus compounds (e.g., triphenylphosphine, etc.), S-triazine derivatives (e.g., 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino- S-triazine, 2-vinyl-4,6-diamino-S-triazine/isocyanuric acid adduct, 2,4-diamino-6-methacryloyloxyethyl-S-triazine/isocyanuric acid adduct, etc.).
硬化剤は、単独または2種類以上を併用して使用できる。 The curing agents can be used alone or in combination of two or more types.
硬化剤の含有量は、熱硬化性化合物(I)100質量部に対して、0.01~15質量部が好ましい。 The content of the curing agent is preferably 0.01 to 15 parts by mass based on 100 parts by mass of thermosetting compound (I).
[重合禁止剤(J)]
本発明の感光性組成物は、重合禁止剤(J)を含有できる。
[Polymerization inhibitor (J)]
The photosensitive composition of the present invention can contain a polymerization inhibitor (J).
重合禁止剤(J)は、例えば、カテコール、レゾールシノール、1,4-ヒドロキノン、2-メチルカテコール、3-メチルカテコール、4-メチルカテコール、2-エチルカテコール、3-エチルカテコール、4-エチルカテコール、2-プロピルカテコール、3-プロピルカテコール、4-プロピルカテコール、2-n-ブチルカテコール、3-n-ブチルカテコール、4-n-ブチルカテコール、2-t-ブチルカテコール、3-t-ブチルカテコール、4-t-ブチルカテコール、3,5-ジ-t-ブチルカテコール等のアルキルカテコール系化合物、2-メチルレゾールシノール、4-メチルレゾールシノール、2-エチルレゾールシノール、4-エチルレゾールシノール、2-プロピルレゾールシノール、4-プロピルレゾールシノール、2-n-ブチルレゾールシノール、4-n-ブチルレゾールシノール、2-t-ブチルレゾールシノール、4-t-ブチルレゾールシノール等のアルキルレゾールシノール系化合物、メチルヒドロキノン、エチルヒドロキノーン、プロピルヒドロキノーン、t-ブチルヒドロキノン、2,5-ジ-t-ブチルヒドロキノン等のアルキルヒドロキノーン系化合物、トリブチルホスフィン、トリオクチルホスフィン、トリシクロヘキシルホスフィン、トリフェニルホスフィン、トリベンジルホスフィン等のホスフィン化合物、トリオクチルホスフィンオキサイド、トリフェニルホスフィンオキサイドなどのホスフィンオキサイド化合物、トリフェニルホスファイト、トリスノニルフェニルホスファイト等のホスファイト化合物、ピロガロール、フロログルシン等が挙げられる。 Examples of the polymerization inhibitor (J) include catechol, resorcinol, 1,4-hydroquinone, 2-methylcatechol, 3-methylcatechol, 4-methylcatechol, 2-ethylcatechol, 3-ethylcatechol, and 4-ethylcatechol. , 2-propylcatechol, 3-propylcatechol, 4-propylcatechol, 2-n-butylcatechol, 3-n-butylcatechol, 4-n-butylcatechol, 2-t-butylcatechol, 3-t-butylcatechol , 4-t-butylcatechol, alkylcatechol compounds such as 3,5-di-t-butylcatechol, 2-methylresorcinol, 4-methylresorcinol, 2-ethylresorcinol, 4-ethylresorcinol, 2 - Alkylresorcinol compounds such as propylresorcinol, 4-propylresorcinol, 2-n-butylresorcinol, 4-n-butylresorcinol, 2-t-butylresorcinol, 4-t-butylresorcinol, Alkylhydroquinone compounds such as methylhydroquinone, ethylhydroquinone, propylhydroquinone, t-butylhydroquinone, 2,5-di-t-butylhydroquinone, tributylphosphine, trioctylphosphine, tricyclohexylphosphine, triphenylphosphine, tri- Examples include phosphine compounds such as benzylphosphine, phosphine oxide compounds such as trioctylphosphine oxide and triphenylphosphine oxide, phosphite compounds such as triphenylphosphite and trisnonylphenylphosphite, pyrogallol, and phloroglucin.
重合禁止剤(J)の含有量は、感光性組成物の不揮発分100質量%中、0.01~0.4質量%が好ましい。 The content of the polymerization inhibitor (J) is preferably 0.01 to 0.4% by mass based on 100% by mass of the nonvolatile content of the photosensitive composition.
[紫外線吸収剤(K)]
本発明の感光性組成物は、紫外線吸収剤(K)を含有できる。
[Ultraviolet absorber (K)]
The photosensitive composition of the present invention can contain an ultraviolet absorber (K).
紫外線吸収剤(K)は、紫外線吸収機能を有する有機化合物であり、ベンゾトリアゾール系有機化合物、トリアジン系有機化合物、ベンゾフェノン系有機化合物、サリチル酸エステル系有機化合物、シアノアクリレート系有機化合物、及びサリシレート系有機化合物等が挙げられる。 The ultraviolet absorber (K) is an organic compound having an ultraviolet absorption function, and includes benzotriazole-based organic compounds, triazine-based organic compounds, benzophenone-based organic compounds, salicylic acid ester-based organic compounds, cyanoacrylate-based organic compounds, and salicylate-based organic compounds. Examples include compounds.
ベンゾトリアゾール系化合物は、例えば、2-(5メチル-2-ヒドロキシフェニル)
ベンゾトリアゾール、2-(2-ヒドロキシ-5-t-ブチルフェニル)-2H-ベンゾトリアゾール、2-[2-ヒドロキシ-3,5-ビス(α, α-ジメチルベンジル)フェニル]-2H-ベンゾトリアゾール、2-(3-tブチル-5-メチル-2-ヒドロキシフェ
ニル)-5-クロロベンゾトリアゾール、2-(2'-ヒドロキシ-5'-t-オクチルフェニル)ベンゾトリアゾール、5%の2-メトキシ-1-メチルエチルアセテートと95%
のベンゼンプロパン酸,3-(2H-ベンゾトリアゾール2-イル)-(1,1-ジメチルエチル)-4-ヒドロキシ,C7-9側鎖及び直鎖アルキルエステルの混合物、2-(2H-ベンゾトリアゾール2-イル)-4,6-ビス(1-メチル-1-フェニルエチル)フェノール、2-(2H-ベンゾトリアゾール2-イル)-6-(1-メチル-1-フェニルエチル)-4-(1,1,3,3-テトラメチルブチル)フェノール、メチル3
-(3-(2H-ベンゾトリアゾール2-イル)-5-t-ブチル-4-ヒドロキシフェニル)プロピオネート/ポリエチレングリコール300の反応生成物、2-(2H-ベンゾトリアゾール2-イル)-4-(1,1,3,3-テトラメチルブチル)フェノール、2,2’-メチレンビス[6-(2H-ベンゾトリアゾール2-イル)-4-(1,1,3,3-テトラメチルブチル)フェノール]、2-(2H-ベンゾトリアゾール2-イル)-p-クレゾール、2-(5-クロロ-2H-ベンゾトリアゾール2-イル)-6-t-ブチル-4-メチルフェノール、2-(3,5-ジ-t-アミル-2-ヒドロキシフェニル)ベンゾトリアゾール、2-[2-ヒドロキシ-5-[2-(メタクリロイルオキシ)エチル]フェニル]-2H-ベンゾトリアゾール、オクチル-3-[3-tert-ブチル-4-ヒドロキシ-5-(5-クロロ-2H-ベンゾトリアゾール2-イル)フェニル]プロピオネート、2-エチルヘキシル-3-[3-tert-ブチル-4-ヒドロキシ-5-(5-クロロ-2H-ベンゾトリアゾール2-イル)フェニル]プロピオネートが挙げられる。
The benzotriazole compound is, for example, 2-(5methyl-2-hydroxyphenyl)
Benzotriazole, 2-(2-hydroxy-5-t-butylphenyl)-2H-benzotriazole, 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole , 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 5% 2-methoxy -1-methylethyl acetate and 95%
benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-(1,1-dimethylethyl)-4-hydroxy, a mixture of C7-9 side chain and linear alkyl esters, 2-(2H-benzotriazole) 2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-( 1,1,3,3-tetramethylbutyl)phenol, methyl 3
-(3-(2H-benzotriazol2-yl)-5-t-butyl-4-hydroxyphenyl)propionate/polyethylene glycol 300 reaction product, 2-(2H-benzotriazol2-yl)-4-( 1,1,3,3-tetramethylbutyl)phenol, 2,2'-methylenebis[6-(2H-benzotriazol2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol] , 2-(2H-benzotriazol-2-yl)-p-cresol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-t-butyl-4-methylphenol, 2-(3,5 -di-t-amyl-2-hydroxyphenyl)benzotriazole, 2-[2-hydroxy-5-[2-(methacryloyloxy)ethyl]phenyl]-2H-benzotriazole, octyl-3-[3-tert- Butyl-4-hydroxy-5-(5-chloro-2H-benzotriazol-2-yl)phenyl]propionate, 2-ethylhexyl-3-[3-tert-butyl-4-hydroxy-5-(5-chloro-2H -benzotriazol2-yl)phenyl]propionate.
市販品は、例えば、BASFジャパン社製のTINUVIN P,PS,234,32
6,329,384-2,900,928,99-2,1130、ADEKA社製のアデカスタブLA-29,LA-31RG,LA-32,LA-36、ケミプロ化成社製のKEMiSORB71,73,74,79,279、大塚化学社製のRUVA-93等が挙げられる。
Commercially available products include, for example, TINUVIN P, PS, 234, 32 manufactured by BASF Japan.
6,329,384-2,900,928,99-2,1130, ADEKA STAB LA-29, LA-31RG, LA-32, LA-36, KEMiSORB71, 73, 74, manufactured by ChemiPro Kasei Co., Ltd. 79,279, RUVA-93 manufactured by Otsuka Chemical Co., Ltd., and the like.
トリアジン系化合物は、例えば、2,4-ビス(2,4-ジメチルフェニル)-6-(2-ヒドロキシ-4-n-オクチルオキシフェニル)-1,3,5-トリアジン、2-[4,6-ビス(2,4-ジメチルフェニル)-1,3,5-トリアジン-2-イル]-5-[3-(ドデシルオキシ)-2-ヒドロキシプロポキシ]フェノール、2-(2,4-ジヒドロキシフェニル)-4,6-ビス(2,4-ジメチルフェニル)-1,3,5-トリアジンと(2-エチルヘキシル)-グリシド酸エステルの反応生成物、2,4-ビス「2-ヒドロキシ-4-ブトキシフェニル」-6-(2,4-ジブトキシフェニル)-1,3,5-トリアジン、2-(4,6-ジフェニル-1,3,5-トリアジン-2-イル)-5-(ヘキシルオキシ)フェノール、2-(4,6-ジフェニル-1,3,5-トリアジン-2-イル)-5-[2-(2-エチルヘキサノイルオキシ)エトキシ]フェノール、2,4,6-トリス(2-ヒドロキシ-4-ヘキシルオキシ-3-メチルフェニル)-1,3,5-トリアジン等が挙げられる。 Examples of triazine compounds include 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-n-octyloxyphenyl)-1,3,5-triazine, 2-[4, 6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-[3-(dodecyloxy)-2-hydroxypropoxy]phenol, 2-(2,4-dihydroxy Reaction product of phenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine and (2-ethylhexyl)-glycidic acid ester, 2,4-bis(2-hydroxy-4 -butoxyphenyl"-6-(2,4-dibutoxyphenyl)-1,3,5-triazine, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-( hexyloxy)phenol, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[2-(2-ethylhexanoyloxy)ethoxy]phenol, 2,4,6- Examples include tris(2-hydroxy-4-hexyloxy-3-methylphenyl)-1,3,5-triazine.
市販品は、例えば、ケミプロ化成社製のKEMISORB 102、BASFジャパン
社製のTINUVIN 400,405,460,477,479,1577ED、AD
EKA社のアデカスタブLA-46,LA-F70、サンケミカル社製のCYASORB
UV-1164等が挙げられる。
Commercially available products include, for example, KEMISORB 102 manufactured by ChemiPro Kasei Co., Ltd., and TINUVIN 400, 405, 460, 477, 479, 1577ED, and AD manufactured by BASF Japan.
EKA's ADK STAB LA-46, LA-F70, Sun Chemical's CYASORB
Examples include UV-1164.
ベンゾフェノン系化合物は、例えば、2,4-ジ-ヒドロキシベンゾフェノン、2-ヒドロキシ-4-メトキシベンゾフェノン、2-ヒドロキシ-4-メトキシベンゾフェノン
5-スルホン酸-3水温、2-ヒドロキシ-4-n-オクトキシベンゾフェノーン、2,2’-ジ-ヒドロキシ-4-メトキシベンゾフェノン、2,2’-ジヒドロキシ-4,4’-ジメトキシベンゾフェノン、4-ドデシロキシ-2-ヒドロキシベンゾフェノン、2-ヒドロキシ-4-オクタデシロキシベンゾフェノン、2,2’ジヒドロキシ-4,4’-ジメトキシベンゾフェノン、2,2’,4,4’-テトラヒドロキシベンゾフェノン、2-ヒドロキシ-4-メトキシ-2’-カルボキシベンゾフェノン等が挙げられる。
Examples of benzophenone compounds include 2,4-di-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone 5-sulfonic acid-3, 2-hydroxy-4-n-oct Xybenzophenone, 2,2'-di-hydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone, 2-hydroxy-4-octa Desyloxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone and the like can be mentioned.
市販品は、例えば、ケミプロ化成社製のKEMISORB 10,11,11S,12
,111、シプロ化成社製のSEESORB 101,107、ADEKA社製のアデカ
スタブ1413、サンケミカル社製のUV-12等が挙げられる。
Commercially available products include, for example, KEMISORB 10, 11, 11S, and 12 manufactured by ChemiPro Kasei Co., Ltd.
, 111, SEESORB 101, 107 manufactured by Shipro Kasei Co., Ltd., ADEKA STAB 1413 manufactured by ADEKA Co., Ltd., UV-12 manufactured by Sun Chemical Co., Ltd., and the like.
サリチル酸エステル系化合物は、例えば、サリチル酸フェニル、サリチル酸p-オクチルフェニル、サリチル酸p-tertブチルフェニル等が挙げられる。 Examples of salicylic acid ester compounds include phenyl salicylate, p-octylphenyl salicylate, and p-tertbutylphenyl salicylate.
紫外線吸収剤(K)の含有量は、光重合開始剤(C)と紫外線吸収剤(K)との合計100質量%中、5~70質量%が好ましい。 The content of the ultraviolet absorber (K) is preferably 5 to 70% by mass out of the total 100% by mass of the photopolymerization initiator (C) and the ultraviolet absorber (K).
[酸化防止剤(L)]
本発明の感光性組成物は、酸化防止剤(L)を含有できる。
[Antioxidant (L)]
The photosensitive composition of the present invention can contain an antioxidant (L).
酸化防止剤(L)は、感光性組成物に含まれる光重合開始剤(C)や熱硬化性化合物(i)が、熱硬化やiTOアニ-ル時の熱工程によって酸化による黄変を防ぐ。特に、感光性組成物の着色剤(E)濃度が高い場合、相対的に重合性化合物(B)の含有量が減少するため、光重合開始剤(C)の増量や、熱硬化性化合物(i)の配合で対応すると硬化膜が黄変し易い。そのため、酸化防止剤を含むことで、加熱工程時の酸化による硬化膜の黄変を防止する。 The antioxidant (L) prevents the photopolymerization initiator (C) and thermosetting compound (i) contained in the photosensitive composition from yellowing due to oxidation during heat curing or the thermal process during iTO annealing. . In particular, when the concentration of the colorant (E) in the photosensitive composition is high, the content of the polymerizable compound (B) is relatively reduced, so it is necessary to increase the amount of the photopolymerization initiator (C) or to increase the amount of the thermosetting compound ( If the formulation i) is used, the cured film tends to yellow. Therefore, by including an antioxidant, yellowing of the cured film due to oxidation during the heating process is prevented.
酸化防止剤(L)は、例えば、ヒンダードフェノール系、ヒンダードアミン系、リン系、イオウ系、およびヒドロキシルアミン系の化合物が挙げられる。なお、本明細書で酸化防止剤は、ハロゲン原子を含有しない化合物が好ましい。 Examples of the antioxidant (L) include hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, and hydroxylamine-based compounds. In this specification, the antioxidant is preferably a compound that does not contain a halogen atom.
これらの中でも、ヒンダードフェノール系酸化防止剤、ヒンダードアミン系酸化防止剤、リン系酸化防止剤、イオウ系酸化防止剤が好ましい。 Among these, hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants are preferred.
ヒンダードフェノール系酸化防止剤は、例えば、1,3,5-トリス(3,5-ジ-t-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、1,1,3-トリス-(2’-メチル-4’-ヒドロキシ-5’-t-ブチルフェニル)-ブタン、4,4’-ブチリデン-ビス-(2-t-ブチル-5-メチルフェノール)、3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオン酸ステアリル、ペンタエリスリトールテトラキス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、3,9-ビス[2-[3-(3-t-ブチル-4-ヒドロキシ-5-メチルフェニル)プロピオニルオキシ]-1,1-ジメチルエチル]-2,4,8,10-テトラオキサスピロ[5.5]ウンデカン、1,3,5-トリス(3,5-ジ-t-ブチル-4-ヒドロキシフェニルメチル)-2,4,6-トリメチルベンゼン、1,3,5-トリス(3-ヒドロキシ-4-t-ブチル-2,6-ジメチルベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、2,2’-メチレンビス(6-t-ブチル-4-エチルフェノール)、2,2’-チオジエチルビス-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)-プロピオネート、N,N-ヘキサメチレンビス(3,5-ジ-t-ブチル-4-ヒドロキシ-ヒドロシンナムアミド)、i-オクチル-3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)
プロピオネート、4,6-ビス(ドデシルチオメチル)-o-クレゾール、3,5-ジ-t-ブチル-4-ヒドロキシベンジルホスホン酸モノエチルエステルのカルシウム塩、4,6-ビス(オクチルチオメチル)-o-クレゾール、ビス[3-(3-メチル-4-ヒドロキシ-5-t-ブチルフェニル)プロピオン酸]エチレンビスオキシビスエチレン、
1,6-ヘキサンジオ-ルビス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニ
ル)プロピオネート、2,4-ビス-(n-オクチルチオ)-6-(4-ヒドロキシ-3,5-ジ-t-ブチルアニリノ)-1,3,5-トリアジン、2,2’-チオ-ビス-(6-t-ブチル-4-メチルフェノール)、2,5-ジ-t-アミル-ヒドロキノン、2,6-ジ-t-ブチル-4-ノニルフェノール、2,2’-イソブチリデン-ビス-(4,6-ジメチル-フェノール)、2,2’-メチレン-ビス-(6-(1-メチル-シクロヘキシル)-p-クレゾール)、2,4-ジメチル-6-(1-メチル-シクロヘキシル)-フェノール等が挙げられる。
The hindered phenolic antioxidant is, for example, 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H ,3H,5H)-trione, 1,1,3-tris-(2'-methyl-4'-hydroxy-5'-t-butylphenyl)-butane, 4,4'-butylidene-bis-(2- t-butyl-5-methylphenol), stearyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, pentaerythritol tetrakis [3-(3,5-di-t-butyl-4 -hydroxyphenyl)propionate, 3,9-bis[2-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl]-2,4,8 , 10-tetraoxaspiro[5.5]undecane, 1,3,5-tris(3,5-di-t-butyl-4-hydroxyphenylmethyl)-2,4,6-trimethylbenzene, 1,3 ,5-tris(3-hydroxy-4-t-butyl-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 2,2' -Methylenebis(6-t-butyl-4-ethylphenol), 2,2'-thiodiethylbis-(3,5-di-t-butyl-4-hydroxyphenyl)-propionate, N,N-hexamethylenebis (3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), i-octyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)
Propionate, 4,6-bis(dodecylthiomethyl)-o-cresol, calcium salt of 3,5-di-t-butyl-4-hydroxybenzylphosphonic acid monoethyl ester, 4,6-bis(octylthiomethyl) -o-cresol, bis[3-(3-methyl-4-hydroxy-5-t-butylphenyl)propionic acid]ethylenebisoxybisethylene,
1,6-hexanedi-rubis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5 -di-t-butylanilino)-1,3,5-triazine, 2,2'-thio-bis-(6-t-butyl-4-methylphenol), 2,5-di-t-amyl-hydroquinone, 2,6-di-t-butyl-4-nonylphenol, 2,2'-isobutylidene-bis-(4,6-dimethyl-phenol), 2,2'-methylene-bis-(6-(1-methyl- cyclohexyl)-p-cresol), 2,4-dimethyl-6-(1-methyl-cyclohexyl)-phenol, and the like.
市販品は、例えば、ADEKA社製のアデカスタブAO-20,AO-30,AO-40,AO-50,AO-60,AO-80,AO-330、ケミプロ社製のKEMINOX101,179,76,9425、BASFジャパン社製のIRGANOX1010,1035,1076,1098,1135,1330,1726,1425WL,1520L,245,259,3114,5057,565、サンケミカル社製のサイアノックスCY-1790,CY-2777等が挙げられる。 Commercially available products include, for example, Adeka Stab AO-20, AO-30, AO-40, AO-50, AO-60, AO-80, AO-330 manufactured by ADEKA, and KEMINOX101, 179, 76, 9425 manufactured by Chemipro. , IRGANOX 1010, 1035, 1076, 1098, 1135, 1330, 1726, 1425WL, 1520L, 245, 259, 3114, 5057, 565 manufactured by BASF Japan, Syanox CY-1790, CY-2777 manufactured by Sun Chemical, etc. Can be mentioned.
ヒンダードアミン系酸化防止剤は、例えば、テトラキス(1,2,2,6,6-ペンタメチル-4-ピペリジル)-1,2,3,4-ブタンテトラカルボキシレート、テトラキス(2,2,6,6-テトラメチル-4-ピペリジル)1,2,3,4-ブタンテトラカルボキシレート、ビス(1,2,2,6,6-ペンタメチル-4-ピペリジル)セバケート、ビス(2,2,6,6-テトラメチル-4-ピペリジル)セバケート、ビス(1-ウンデカノキシ-2,2,6,6-テトラメチルピペリジン-4-イル)カルボネート、1,2,2,6,6-ペンタメチル-4-ピペリジルメタクリレート、2,2,6,6-テトラメチル-4-ピペリジルメタクリレート、コハク酸ジメチルと1-(2-ヒドロキシエチル)-4-ヒドロキシ-2,2,6,6-テトラメチルピペリジンとの重縮合物、ポリ[[6-[(1,1,3,3-テトラメチルブチル)アミノ]-s-トリアジン-2,4-ジイル]-[(2,2,6,6-テトラメチル-4-ピペリジル)イミノ]-ヘキサメチレン-[(2,2,6,6-テトラメチル-4-ピペリジル)イミノ]]、4-ヒドロキシ-2,2,6,6-テトラメチル-1-ピペリジンエタノールと3,5,5-トリメチルヘキサン酸のエステル、N,N’-4,7-テトラキス〔4,6-ビス{N-ブチル-N-(1,2,2,6,6-ペンタメチル-4-ピペリジル)アミノ}-1,3,5-トリアジン-2-イル〕-4,7-ジアザデカン-1,10-ジアミン、デカン二酸ビス(2,2,6,6-テトラメチル-1-(オクチルオキシ)-4-ピペリジニル)エステル,1,1-ジメチルエチルヒドロペルオキシドとオクタンの反応生成物、ビス(1,2,2,6,6-ペンタメチル-4-ピリペリジル)[[3,5-ビス(1,1ジメチルエチル)-4-ヒドロキシフェニル]メチル]ブチルマロネートメチル1,2,2,6,6-ペンタメチル-4-ピリペリジルセバケート、ポリ[[6-モルホリノ-s-トリアジン-2,4-ジイル]-[(2,2,6,6-テトラメチル-4-ピペリジル)イミノ]-ヘキサメチレン-[(2,2,6,6-テトラメチル-4-ピペリジル)イミノ]]、2,2,6,6-テトラメチル-4-ピペリジル-C12-21およびC18不飽和脂肪酸エステル、N,N’-ビス(2,2,6,6-テトラメチル-4-ピペリジル)-1,6-ヘキサメチレンジアミン、2-メチル-2-(2,2,6,6-テトラメチル-4-ピペリジル)アミノ-N-(2,2,6,6-テトラメチル-4-ピペリジル)プロピオンアミド等が挙げられる。 Examples of hindered amine antioxidants include tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, tetrakis(2,2,6,6 -tetramethyl-4-piperidyl) 1,2,3,4-butanetetracarboxylate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis(2,2,6,6 -tetramethyl-4-piperidyl) sebacate, bis(1-undecanoxy-2,2,6,6-tetramethylpiperidin-4-yl)carbonate, 1,2,2,6,6-pentamethyl-4-piperidyl methacrylate , 2,2,6,6-tetramethyl-4-piperidyl methacrylate, polycondensate of dimethyl succinate and 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine , poly[[6-[(1,1,3,3-tetramethylbutyl)amino]-s-triazine-2,4-diyl]-[(2,2,6,6-tetramethyl-4-piperidyl) ) imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl)imino]], 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol and 3, Ester of 5,5-trimethylhexanoic acid, N,N'-4,7-tetrakis[4,6-bis{N-butyl-N-(1,2,2,6,6-pentamethyl-4-piperidyl) amino}-1,3,5-triazin-2-yl]-4,7-diazadecane-1,10-diamine, bis(2,2,6,6-tetramethyl-1-(octyloxy) decanedioate) -4-piperidinyl) ester, reaction product of 1,1-dimethylethyl hydroperoxide and octane, bis(1,2,2,6,6-pentamethyl-4-pyriperidyl)[[3,5-bis(1, 1dimethylethyl)-4-hydroxyphenyl]methyl]butyl malonate methyl 1,2,2,6,6-pentamethyl-4-pyriperidyl sebacate, poly[[6-morpholino-s-triazine-2,4 -diyl]-[(2,2,6,6-tetramethyl-4-piperidyl)imino]-hexamethylene-[(2,2,6,6-tetramethyl-4-piperidyl)imino]], 2, 2,6,6-tetramethyl-4-piperidyl-C12-21 and C18 unsaturated fatty acid ester, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6- Hexamethylene diamine, 2-methyl-2-(2,2,6,6-tetramethyl-4-piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide, etc. Can be mentioned.
市販品は、例えば、ADEKA社製のアデカスタブLA-52,LA-57,LA-6
3P,LA-68,LA-72,LA-77Y,LA-77G,LA-81,LA-82,LA-87,LA-402F,LA-502XP、ケミプロ化成社製のKAMISTAB29,62,77,94、BASFジャパン社製のTinuvin111FDL,123,144,249,292,5100、サンケミカル社製のサイアソ-ブUV-3346,UV-3529,UV-3853等が挙げられる。
Commercially available products include, for example, ADEKA STAB LA-52, LA-57, LA-6.
3P, LA-68, LA-72, LA-77Y, LA-77G, LA-81, LA-82, LA-87, LA-402F, LA-502XP, KAMISTAB29, 62, 77, 94 manufactured by ChemiPro Kasei Co., Ltd. , Tinuvin 111FDL, 123, 144, 249, 292, 5100 manufactured by BASF Japan, and Cyasorb UV-3346, UV-3529, UV-3853 manufactured by Sun Chemical.
リン系酸化防止剤は、例えば、ジ(2,6-ジ-t-ブチル-4-メチルフェニル)ペンタエリスリトールジホスファイト、ジステアリルペンタエリスリトールジホスファイト、2,2’-メチレンビス(4,6-ジ-t-ブチルフェニル)2-エチルヘキシルホスファイト、トリス(2,4-ジ-t-ブチルフェニル)ホスファイト、トリス(ノニルフェニル)ホスファイト、テトラ(C12~C15アルキル)-4,4’-イソプロピリデンジフェニルジホスファイト、ジフェニルモノ(2-エチルヘキシル)ホスファイト、ジフェニルイソデシルホスファイト、トリス(イソデシル)ホスファイト、トリフェニルホスファイト、テトラキス(2,4-ジ-t-ブチルフェニル)-4,4-ビフェニルジフォスホニト、トリス(トリデシル)ホスファイト、フェニルイソオクチルホスファイト、フェニルイソデシルホスファイト、フェニルジ(トリデシル)ホスファイト、ジフェニルイソオクチルホスファイト、ジフェニルトリデシルホスファイト、4,4’-イソプロピリデンジフェノールアルキルホスファイト、トリスノニルフェニルホスファイト、トリスジノニルフェニルホスファイト、トリス(ビフェニル)ホスファイト、ジ(2,4-ジ-t-ブチルフェニル)ペンタエリスリトールジホスファイト、ジ(ノニルフェニル)ペンタエリスリトールジホスファイト、フェニルビスフェノールAペンタエリスリトールジホスファイト、テトラトリデシル4,4’-ブチリデンビス(3-メチル-6-t-ブチルフェノール)ジホスファイト、ヘキサトリデシル1,1,3-トリス(2-メチル-4-ヒドロキシ-5-t-ブチルフェニル)ブタントリホスファイト、3,5-ジ-t-ブチル-4-ヒドロキシベンジルホスファイトジエチルエステル、ソジウムビス(4-t-ブチルフェニル)ホスファイト、ソジウム-2,2-メチレン-ビス(4,6-ジ-t-ブチルフェニル)-ホスファイト、1,3-ビス(ジフェノキシフォスフォニロキシ)-ベンゼン、亜リン酸エチルビス(2,4-ジt-ブチル-6-メチルフェニル)等が挙げられる。 Examples of phosphorus-based antioxidants include di(2,6-di-t-butyl-4-methylphenyl)pentaerythritol diphosphite, distearylpentaerythritol diphosphite, and 2,2'-methylenebis(4,6 -di-t-butylphenyl)2-ethylhexylphosphite, tris(2,4-di-t-butylphenyl)phosphite, tris(nonylphenyl)phosphite, tetra(C12-C15 alkyl)-4,4' -Isopropylidene diphenyl diphosphite, diphenylmono(2-ethylhexyl) phosphite, diphenylisodecyl phosphite, tris(isodecyl) phosphite, triphenyl phosphite, tetrakis(2,4-di-t-butylphenyl)- 4,4-biphenyldiphosphonite, tris(tridecyl)phosphite, phenylisooctylphosphite, phenylisodecylphosphite, phenyldi(tridecyl)phosphite, diphenylisooctylphosphite, diphenyltridecylphosphite, 4,4 '-Isopropylidene diphenol alkyl phosphite, trisnonylphenyl phosphite, trisdinonylphenyl phosphite, tris(biphenyl) phosphite, di(2,4-di-t-butylphenyl)pentaerythritol diphosphite, di (nonylphenyl) pentaerythritol diphosphite, phenylbisphenol A pentaerythritol diphosphite, tetratridecyl 4,4'-butylidenebis(3-methyl-6-t-butylphenol) diphosphite, hexatridecyl 1,1,3- Tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane triphosphite, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, sodium bis(4-t-butylphenyl) phosphite phyto, sodium-2,2-methylene-bis(4,6-di-t-butylphenyl)-phosphite, 1,3-bis(diphenoxyphosphonyloxy)-benzene, ethylbis(2,4-phosphite) -di-t-butyl-6-methylphenyl) and the like.
市販品は、例えば、ADEKA社製のアデカスタブPEP-36,PEP-8,HP-10,2112,1178,1500,C,135A,3010,TPP、BASFジャパン社製のIRGAFOS168、クラリアントケミカルズ社製のHostanoxP-EPQ等が挙げられる。 Commercially available products include, for example, ADEKA STAB PEP-36, PEP-8, HP-10, 2112, 1178, 1500, C, 135A, 3010, TPP manufactured by ADEKA, IRGAFOS168 manufactured by BASF Japan, and HostanoxP manufactured by Clariant Chemicals. - EPQ etc.
イオウ系酸化防止剤は、例えば、2,2-ビス{〔3-(ドデシルチオ)-1-オキソプロポキシ〕メチル}プロパン-1,3-ジイルビス〔3-(ドデシルチオ)プロピオネート〕、3,3’-チオビスプロピオン酸ジトリデシル、2,2-チオ-ジエチレンビス〔3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート〕、2,4-ビス〔(オクチルチオ)メチル〕-o-クレゾール、2,4-ビス〔(ラウリルチオ)メチル〕-o-クレゾール等が挙げられる。 Sulfur-based antioxidants include, for example, 2,2-bis{[3-(dodecylthio)-1-oxopropoxy]methyl}propane-1,3-diylbis[3-(dodecylthio)propionate], 3,3'- Ditridecyl thiobispropionate, 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis[(octylthio)methyl]-o- Examples include cresol, 2,4-bis[(laurylthio)methyl]-o-cresol, and the like.
市販品は、例えば、ADEKA社製のアデカスタブAO-412S,AO-503、ケミプロ化成社製のKEMiNOXPLS等が挙げられる。 Examples of commercially available products include ADEKA STAB AO-412S and AO-503 manufactured by ADEKA, and KEMiNOXPLS manufactured by ChemiPro Kasei.
酸化防止剤(L)は、単独または2種類以上を併用して使用できる。 The antioxidant (L) can be used alone or in combination of two or more kinds.
酸化防止剤(L)の含有量は、感光性組成物の不揮発分100質量%中、0.5~5.0質量%が好ましい。適量含有すると透過率、分光特性、及び感度が向上する。 The content of the antioxidant (L) is preferably 0.5 to 5.0% by weight based on 100% by weight of the nonvolatile content of the photosensitive composition. Containing an appropriate amount improves transmittance, spectral characteristics, and sensitivity.
[レベリング剤(M)]
本発明の感光性組成物は、レベリング剤(M)を含有できる。これにより、塗工時の基板に対する濡れ性、及び乾燥性がより向上する。
[Leveling agent (M)]
The photosensitive composition of the present invention can contain a leveling agent (M). This further improves the wettability and drying properties for the substrate during coating.
レベリング剤(M)は、例えば、シリコーン系界面活性剤、フッ素系界面活性剤、ノニオン性界面活性剤、カチオン性界面活性剤、アニオン性界面活性剤、両性界面活性剤等が挙げられる。 Examples of the leveling agent (M) include silicone surfactants, fluorine surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and amphoteric surfactants.
シリコーン系界面活性剤は、例えば、シロキサン結合からなる直鎖状ポリマーや、側鎖や末端に有機基を導入した変性シロキサンポリマーが挙げられる。 Examples of silicone surfactants include linear polymers comprising siloxane bonds and modified siloxane polymers having organic groups introduced into side chains or terminals.
市販品は、例えば、ビックケミー社製のBYK-300,306,310,313,315N,320,322,323,330,331,333,342,345,346,347,348,349,370,377,378,3455,UV3510,3570、東レ・ダウコ-ニング社製のFZ-7002,2110,2122,2123,2191,5609、信越化学工業社製のX-22-4952、X-22-4272、X-22-6266、KF-351A、KF-354L、KF-355A、KF-945、KF-640、KF-642、KF-643、X-22-4515、KF-6004、KP-341等が挙げられる。 Commercially available products include, for example, BYK-300, 306, 310, 313, 315N, 320, 322, 323, 330, 331, 333, 342, 345, 346, 347, 348, 349, 370, 377, manufactured by BYK Chemie. 378, 3455, UV3510, 3570, FZ-7002, 2110, 2122, 2123, 2191, 5609 manufactured by Dow Corning Toray, X-22-4952, X-22-4272, X- manufactured by Shin-Etsu Chemical Co., Ltd. 22-6266, KF-351A, KF-354L, KF-355A, KF-945, KF-640, KF-642, KF-643, X-22-4515, KF-6004, KP-341, etc.
フッ素系界面活性剤は、例えば、フルオロカーボン鎖を有する界面活性剤又はレベリング剤が挙げられる。 Examples of the fluorosurfactant include a surfactant or a leveling agent having a fluorocarbon chain.
市販品は、例えば、AGCセイミケミカル社製のサーフロンS-242,243,420,611,651,386、DIC社製のメガファックF-253,477,551,552,555,558,560,570,575,576、R-40-LM、R-41、RS-72-K、DS-21、住友スリーエム社製のFC-4430,4432、三菱マテリアル電子化成社製のEF-PP31N09、EF-PP33G1、EF-PP32C1、ネオス社製フタージェントの602A等が挙げられる。 Commercially available products include, for example, Surflon S-242, 243, 420, 611, 651, 386 manufactured by AGC Seimi Chemical, and Megafac F-253, 477, 551, 552, 555, 558, 560, 570 manufactured by DIC. , 575, 576, R-40-LM, R-41, RS-72-K, DS-21, FC-4430, 4432 manufactured by Sumitomo 3M, EF-PP31N09, EF-PP33G1 manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd. , EF-PP32C1, and Futergent 602A manufactured by Neos.
ノニオン性界面活性剤は、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンミリステルエーテル、ポリオキシエチレンオクチルドデシルエーテル、ポリオキシアルキレンアルキルエーテル、ポリオキシフェニレンジスチレン化フェニルエーテル、ポリオキシエチレントリベンジルフェニルエーテル、ポリオキシエチレンポリオキシプロピレングリコール、ポリオキシアルキレンアルケニルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンアルキルエーテルリン酸エステル、ソルビタンモノラウレート、ソルビタンモノパルミテ-ト、ソルビタンモノステアレート、ソルビタンジステアレート、ソルビタントリステアレート、ソルビタンモノオレート、ソルビタントリオレート、ソルビタンセスキオレート、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテ-ト、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリステアレート、ポリオキシエチレンソルビタンモノオレート、ポリオキシエチレンソルビタントリイソステアレート、テトラオレイン酸ポリオキシエチレンソルビット、グリセロ-ルモノステアレート、グリセロ-ルモノオレート、ポリエチレングリコールモノラウレート、ポリエチレングリコールモノステアレート、ポリエチレングリコールジステアレート、ポリエチレングリコールモノオレート、ポリオキシエチレン硬化ヒマシ油、ポリオキシエチレンアルキルアミン、アルキルアルカノールアミド、アルキルイミダゾリン等が挙げられる。 Nonionic surfactants include, for example, polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene alkyl ether, polyoxyethylene myristele ether, polyoxyethylene octyl Dodecyl ether, polyoxyalkylene alkyl ether, polyoxyphenylene distyrenated phenyl ether, polyoxyethylene tribenzylphenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyalkylene alkenyl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Alkyl ether phosphate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan distearate, sorbitan tristearate, sorbitan monooleate, sorbitan triolate, sorbitan sesquiolate, polyoxyethylene sorbitan mono Laurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan triisostearate, polyoxytetraoleate Ethylene sorbitol, glycerol monostearate, glycerol monooleate, polyethylene glycol monolaurate, polyethylene glycol monostearate, polyethylene glycol distearate, polyethylene glycol monooleate, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkylamine, alkyl Examples include alkanolamide and alkylimidazoline.
市販品は、例えば、花王社製のエマルゲン103,104P,106,108,109P,120,123P,130K,147,150,210P,220,306P,320P,350,404,408,409PV,420,430,705,707,709,1108,1118S-70,1135S-70,1150S-60,2020G-HA,2025G,LS-106,LS-110,LS-114,MS-110,A-60,A-90,B-66,PP-290、ラテムルPD-420,PD-430,PD-430S,PD-450、レオドールSP-L10,SP-P10,SP-S10V,SP-S20,SP-S30V,SP-O10V,SP-O30V、スーパーSP-L10,AS-10V,AO-10V,AO-15V,TW-L120,TW-L106,TW-P120,TW-S120V,TW-S320V,TW-O120V,TW-O106V,TW-iS399C、スーパーTW-L120,430V,440V,460V,MS-50,MS-60,MO-60,MS-165V、エマノーン1112,3199V,3299V,3299RV,4110,CH-25,CH-40,CH-60(K),アミ-ト102,105,105A,302,320、アミノーンPK-02S、L-02、ホモゲノールL-95、ADEKA社製のアデカプルロニック(登録商標)L-23,31,44,61,62,64,71,72,101,121、TR-701,702,704,913R、共栄社化学社製の(メタ)アクリル酸系(共)重合体ポリフロ-No.75,No.90,No.95等が挙げられる。 Commercially available products include, for example, Emulgen 103, 104P, 106, 108, 109P, 120, 123P, 130K, 147, 150, 210P, 220, 306P, 320P, 350, 404, 408, 409PV, 420, 430 manufactured by Kao Corporation. , 705, 707, 709, 1108, 1118S-70, 1135S-70, 1150S-60, 2020G-HA, 2025G, LS-106, LS-110, LS-114, MS-110, A-60, A-90 , B-66, PP-290, Latemur PD-420, PD-430, PD-430S, PD-450, Rheodor SP-L10, SP-P10, SP-S10V, SP-S20, SP-S30V, SP-O10V , SP-O30V, Super SP-L10, AS-10V, AO-10V, AO-15V, TW-L120, TW-L106, TW-P120, TW-S120V, TW-S320V, TW-O120V, TW-O106V, TW-iS399C, Super TW-L120, 430V, 440V, 460V, MS-50, MS-60, MO-60, MS-165V, Emanon 1112, 3199V, 3299V, 3299RV, 4110, CH-25, CH-40, CH-60 (K), Amito 102, 105, 105A, 302, 320, Aminone PK-02S, L-02, Homogenol L-95, ADEKA Pluronic (registered trademark) L-23, 31, 44,61,62,64,71,72,101,121, TR-701,702,704,913R, (meth)acrylic acid-based (co)polymer Polyflo-No. manufactured by Kyoeisha Chemical Co., Ltd. 75, No. 90, No. 95 etc. are mentioned.
カチオン性界面活性剤は、例えばアルキルアミン塩やラウリルトリメチルアンモニウムクロライド、ステアリルトリメチルアンモニウムクロライド、セチルトリメチルアンモニウムクロライドなどのアルキル4級アンモニウム塩やそれらのエチレンオキサイド付加物が挙げられる。 Examples of the cationic surfactant include alkyl amine salts, alkyl quaternary ammonium salts such as lauryltrimethylammonium chloride, stearyltrimethylammonium chloride, and cetyltrimethylammonium chloride, and ethylene oxide adducts thereof.
市販品は、例えば、花王社製のアセタミン24、コータミン24P、60W、86Pコンク等が挙げられる。 Examples of commercially available products include Acetamine 24, Cortamine 24P, 60W, and 86P Conc manufactured by Kao Corporation.
アニオン性界面活性剤は、例えば、ポリオキシエチレンアルキルエーテル硫酸塩、ドデシルベンゼンスルホン酸ナトリウム、スチレン-アクリル酸共重合体のアルカリ塩、アルキルナフタレンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、ステアリン酸ナトリウム、ラウリル硫酸ナトリウム、スチレン-アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステル等が挙げられる。 Examples of anionic surfactants include polyoxyethylene alkyl ether sulfates, sodium dodecylbenzenesulfonate, alkali salts of styrene-acrylic acid copolymers, sodium alkylnaphthalenesulfonates, sodium alkyldiphenyl ether disulfonates, and lauryl sulfate monoethanol. Examples include amine, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, and polyoxyethylene alkyl ether phosphate.
市販品は、例えば、ネオス社製のフタージェント100,150、ADEKA社製のアデカホープYES-25、アデカコールTS-230E,PS-440E,EC-8600等が挙げられる。 Commercially available products include, for example, Ftergent 100 and 150 manufactured by Neos, ADEKA HOPE YES-25, ADEKA COL TS-230E, PS-440E, and EC-8600 manufactured by ADEKA.
両性界面活性剤は、例えば、ラウリン酸アミドプロピルベタイン、ラウリルベタイン、コカミドプロピルベタイン、ステアリルベタイン、アルキルジメチルアミノ酢酸ベタイン等のアルキルベタイン、ラウリルジメチルアミンオキサイド等のアルキルアミンオキサイド等が挙げられる。 Examples of the amphoteric surfactant include alkyl betaines such as lauric acid amidopropyl betaine, lauryl betaine, cocamidopropyl betaine, stearyl betaine, and alkyldimethylaminoacetic acid betaine, and alkyl amine oxides such as lauryl dimethylamine oxide.
市販品は、花王社製のアンヒトール20AB,20BS,24B,55AB,86B,20Y-B,20N等が挙げられる。 Commercially available products include Amhitol 20AB, 20BS, 24B, 55AB, 86B, 20Y-B, and 20N manufactured by Kao Corporation.
レベリング剤(M)は、単独または2種類以上を併用して使用できる。 The leveling agent (M) can be used alone or in combination of two or more.
レベリング剤(M)の含有量は、感光性組成物の不揮発分100質量%中、0.001~
2.0質量%が好ましく、0.005~1.0質量%がより好ましい。この範囲内であることで、感光性組成物の塗布性と密着性のバランスがより向上する。
The content of the leveling agent (M) is from 0.001 to 100% by mass of the nonvolatile content of the photosensitive composition.
It is preferably 2.0% by weight, more preferably 0.005 to 1.0% by weight. Within this range, the balance between coating properties and adhesion of the photosensitive composition is further improved.
[貯蔵安定剤(N)]
本発明の感光性組成物は、貯蔵安定剤(N)を含有できる。これにより、感光性組成物の経時粘度が安定化する。
[Storage stabilizer (N)]
The photosensitive composition of the present invention can contain a storage stabilizer (N). This stabilizes the viscosity of the photosensitive composition over time.
貯蔵安定剤(N)は、例えば、ベンジルトリメチルクロライド、ジエチルヒドロキシアミンなどの4級アンモニウムクロライド、乳酸、シュウ酸などの有機酸およびそのメチルエーテル、t-ブチルピロカテコール、テトラエチルホスフィン、テトラフェニルなどの有機ホスフィン、亜リン酸塩等が挙げられる。 Storage stabilizers (N) include, for example, quaternary ammonium chloride such as benzyl trimethyl chloride and diethyl hydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, t-butylpyrocatechol, tetraethylphosphine, and tetraphenyl. Examples include organic phosphines and phosphites.
貯蔵安定剤(N)は、単独または2種類以上を併用して使用できる。 Storage stabilizers (N) can be used alone or in combination of two or more.
貯蔵安定剤(N)の含有量は、感光性組成物の不揮発分100質量%中、0.1~10質量部が好ましい。 The content of the storage stabilizer (N) is preferably 0.1 to 10 parts by mass based on 100% by mass of nonvolatile content of the photosensitive composition.
[密着向上剤(O)]
本発明の感光性組成物は、密着向上剤(O)を含有できる。これにより被膜と基材の密着性が向上する。また、フォトリソグラフィー法で幅が狭いパターンを形成し易くなる。
[Adhesion improver (O)]
The photosensitive composition of the present invention can contain an adhesion improver (O). This improves the adhesion between the coating and the base material. Further, it becomes easier to form a narrow pattern using photolithography.
密着向上剤(O)は、例えば、シランカップリング剤等が挙げられる。シランカップリング剤は、例えば、ビニルトリメトキシシラン、ビニルトリエトキシシラン等のビニルシラン類、3-メタクリロキシプロピルメチルジメトキシシラン、3-メタクリロキシプロピルトリメトキシシラン、3-メタクリロキシプロピルメチルジエトキシシラン、3-メタクリロキシプロピルトリエトキシシラン、3-アクリロキシプロピルトリメトキシシラン等の(メタ)アクリルシラン類、2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、3-グリシドキシプロピルメチルジメトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルメチルジエトキシシラン、3-グリシドキシプロピルトリエトキシシラン等のエポキシシラン類、N-2-(アミノエチル)-3-アミノプロピルメチルジメトキシシラン、N-2-(アミノエチル)-3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリメトキシシラン、3-アミノプロピルトリエトキシシラン、3-トリエトキシシリル-N-(1,3-ジメチル-ブチリデン)プロピルアミン、N-フェニル-3-アミノプロピルトリメトキシシラン、N-(ビニルベンジル)-2-アミノエチル-3-アミノプロピルトリメトキシシランの塩酸塩等のアミノシラン類、3-メルカプトプロピルメチルジメトキシシラン、3-メルカプトプロピルトリメトキシシラン等のメルカプト類、p-スチリルトリメトキシシラン等のスチリル類、3-ウレイドプロピルトリエトキシシラン等のウレイド類、ビス(トリエトキシシリルプロピル)テトラスルフィド等のスルフィド類、3-イソシアネートプロピルトリエトキシシラン等のイソシアネート類などのシランカップリング剤が挙げられる。 Examples of the adhesion improver (O) include silane coupling agents. Examples of the silane coupling agent include vinyl silanes such as vinyltrimethoxysilane and vinyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, (Meth)acrylic silanes such as 3-methacryloxypropyltriethoxysilane and 3-acryloxypropyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane , 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane and other epoxysilanes, N-2-(aminoethyl)-3-aminopropyl Methyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3- Aminosilanes such as hydrochloride of dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane, 3-mercaptopropyl Mercapto compounds such as methyldimethoxysilane and 3-mercaptopropyltrimethoxysilane, styryl compounds such as p-styryltrimethoxysilane, ureido compounds such as 3-ureidopropyltriethoxysilane, bis(triethoxysilylpropyl)tetrasulfide, etc. Examples include silane coupling agents such as sulfides and isocyanates such as 3-isocyanatepropyltriethoxysilane.
密着向上剤(O)は、単独または2種類以上を併用して使用できる。 The adhesion improver (O) can be used alone or in combination of two or more.
密着向上剤(O)の含有量は、感光性組成物の不揮発分100質量%中、0.01~10質量部が好ましく、0.05~5質量部がより好ましい。 The content of the adhesion improver (O) is preferably 0.01 to 10 parts by weight, more preferably 0.05 to 5 parts by weight based on 100% by weight of nonvolatile content of the photosensitive composition.
[有機溶剤(P)]
本発明の感光性組成物は、有機溶剤(P)を含有できる。
[Organic solvent (P)]
The photosensitive composition of the present invention can contain an organic solvent (P).
有機溶剤(P)は、例えば、1,2,3-トリクロロプロパン、1-メトキシ-2-プロ
パノール、乳酸エチル、1,3-ブタンジオ-ル、1,3-ブチレングリコール、1,3-ブチレングリコールジアセテート、1,4-ジオキサン、2-ヘプタノーン、2-メチル-1,3-プロパンジオ-ル、3,5,5-トリメチル-2-シクロヘキセン-1-オン、3,3,5-トリメチルシクロヘキサノン、3-エトキシプロピオン酸エチル、3-メチル-1,3-ブタンジオ-ル、3-メトキシ-3-メチル-1-ブタノール、3-メトキシ-3-メチルブチルアセテート、3-メトキシブタノール、3-メトキシブチルアセテート、4-ヘプタノーン、m-キシレン、m-ジエチルベンゼン、m-ジクロロベンゼン、N,N-ジメチルアセトアミド、N,N-ジメチルホルムアミド、n-ブチルアルコール、n-ブチルベンゼン、n-プロピルアセテート、N-メチルピロリドン、o-キシレン、o-クロロトールエン、o-ジエチルベンゼン、o-ジクロロベンゼン、p-クロロトールエン、p-ジエチルベンゼン、sec-ブチルベンゼン、tert-ブチルベンゼン、γ-ブチロラクトン、イソブチルアルコール、イソホロン、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノターシャリーブチルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノプロピルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテルアセテート、ジイソブチルケトン、ジエチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノイソプロピルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノメチルエーテル、シクロヘキサノール、シクロヘキサノールアセテート、シクロヘキサノン、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールメチルエーテルアセテート、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノブチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノメチルエーテル、ダイアセトンアルコール、トリアセチン、トリプロピレングリコールモノブチルエーテル、トリプロピレングリコールモノメチルエーテル、プロピレングリコールジアセテート、プロピレングリコールフェニルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテルプロピオネート、ベンジルアルコール、メチルイソブチルケトン、メチルシクロヘキサノール、酢酸n-アミル、酢酸n-ブチル、酢酸イソアミル、酢酸イソブチル、酢酸プロピル、二塩基酸エステル等が挙げられる。これらの中でも、顔料の分散性、アルカリ可溶樹脂の溶解性の観点から、乳酸エチル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート等のグリコールアセテート類、ベンジルアルコール、ダイアセトンアルコール等のアルコール類やシクロヘキサノン等のケトン類が好ましい。
The organic solvent (P) is, for example, 1,2,3-trichloropropane, 1-methoxy-2-propanol, ethyl lactate, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol. Diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone , ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxy Butyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N -Methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, Isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene Glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether Acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol Monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene Glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate , propyl acetate, dibasic acid esters, and the like. Among these, from the viewpoint of pigment dispersibility and alkali-soluble resin solubility, ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, etc. Alcohols such as glycol acetates, benzyl alcohol and diacetone alcohol, and ketones such as cyclohexanone are preferred.
有機溶剤(P)は、単独または2種類以上を併用して使用できる。 The organic solvent (P) can be used alone or in combination of two or more.
[感光性組成物の製造方法]
本発明の感光性組成物は、例えば、着色剤(E)、アルカリ可溶性樹脂(A)、分散樹脂(G)、色素誘導体(F)、及び有機溶剤(P)等を加えて分散処理を行うことで、分散体を製造する。その後、前記分散体に、重合性化合物(B)、光重合開始剤(C)等を配合し混合することで製造できる。なお、各材料を配合するタイミングは、任意である。また、分散工程を複数回行うこともできる。
[Method for manufacturing photosensitive composition]
The photosensitive composition of the present invention is subjected to a dispersion treatment by adding, for example, a colorant (E), an alkali-soluble resin (A), a dispersion resin (G), a dye derivative (F), an organic solvent (P), etc. In this way, a dispersion is produced. Thereafter, the polymerizable compound (B), the photopolymerization initiator (C), etc. are added to the dispersion and mixed. Note that the timing of blending each material is arbitrary. Moreover, the dispersion step can also be performed multiple times.
分散処理を行う分散機は、例えば、2本ロ-ルミル、3本ロールミル、ボ-ルミル、横型サンドミル、縦型サンドミル、アニュラー型ビ-ズミル、又はアトライター等が挙げられる。 Examples of the dispersing machine that performs the dispersion treatment include a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, an annular bead mill, and an attritor.
分散体中の着色剤の平均分散粒子径(二次粒子径)は、30~200nmが好ましく、40~200nmがより好ましい。適度な粒子径を有すると分散安定性が高い感光性組成物が得やすい。 The average dispersed particle size (secondary particle size) of the colorant in the dispersion is preferably 30 to 200 nm, more preferably 40 to 200 nm. When the particle size is appropriate, it is easy to obtain a photosensitive composition with high dispersion stability.
平均分散粒子径(二次粒子径)の測定方法は、例えば、動的光散乱法(FFTパワ-スペクトール法)を採用した日機装社のマイクロトラックUPA-EX150を用い、粒子透過性を吸収モ-ド、粒子形状を非球形とし、D50粒子径を平均径とする。測定用の希釈溶剤は分散に使用した有機溶剤をそれぞれ用い、超音波で処理したサンプルについてサンプル調整直後に測定するとバラツキが少ない結果が得られやすく好ましい。 The average dispersed particle size (secondary particle size) can be measured using, for example, Microtrack UPA-EX150 manufactured by Nikkiso Co., Ltd., which employs a dynamic light scattering method (FFT power spectrum method). D. The particle shape is non-spherical, and the D50 particle diameter is the average diameter. It is preferable to use the organic solvent used for dispersion as the diluting solvent for measurement, and to measure the sample treated with ultrasonic waves immediately after sample preparation, because results with less variation can be easily obtained.
感光性組成物は、遠心分離、焼結フィルタやメンブレンフィルタによる濾過等の手段にて、5μm以上の粗大粒子、好ましくは1μm以上の粗大粒子、さらに好ましくは0.5μm以上の粗大粒子、および混入した塵の除去を行うことが好ましい。本発明の感光性組成物は、実質的に0.5μm以上の粒子を含まないことが好ましく、0.3μm以下の粒子を含まないことがより好ましい。 The photosensitive composition is prepared by centrifugation, filtration with a sintered filter or membrane filter, etc. to remove coarse particles of 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more, and contaminants. It is preferable to remove the dust. The photosensitive composition of the present invention preferably does not substantially contain particles of 0.5 μm or more, and more preferably does not contain particles of 0.3 μm or less.
<光学フィルタ>
本発明の光学フィルタは、基板、及び本発明の感光性組成物から形成されるフィルタセグメントを備える。光学フィルタは、様々な用途に使用できる。本明細書で光学フィルタは、カラーフィルタが好ましい。
フィルタセグメントは、カラーフィルタの場合には、使用する着色剤(E)の種類を適宜選択することで、赤色フィルタセグメント、緑色フィルタセグメント、及び青色フィルタセグメントを有する。前記フィルタセグメントに代えてまたは加え、マゼンタ色フィルタセグメント、シアン色フィルタセグメント、イエロー色フィルタセグメント、ホワイトフィルタセグメント、ブラックフィルタセグメントを有することもできる。また、着色剤(E)を使用しないクリアのフィルタを有することができる。
前記基板は、透明基板、及び反射基板が挙げられる。前記透明基板は、例えば、ガラス基板が挙げられる。前記反射基材は、例えばアルミ電極や金属薄膜を反射面として使用する基板が挙げられる。
<Optical filter>
The optical filter of the present invention includes a substrate and a filter segment formed from the photosensitive composition of the present invention. Optical filters can be used for a variety of purposes. In this specification, the optical filter is preferably a color filter.
In the case of a color filter, the filter segment has a red filter segment, a green filter segment, and a blue filter segment by appropriately selecting the type of colorant (E) used. In place of or in addition to the filter segments, a magenta filter segment, a cyan filter segment, a yellow filter segment, a white filter segment, and a black filter segment may be included. Furthermore, it is possible to have a clear filter that does not use a colorant (E).
Examples of the substrate include a transparent substrate and a reflective substrate. Examples of the transparent substrate include a glass substrate. Examples of the reflective base material include a substrate using an aluminum electrode or a metal thin film as a reflective surface.
[光学フィルタの製造方法]
光学フィルタの製造方法は、例えば、基板上に感光性組成物を塗布し組成物の層(被膜)を形成する工程(1)、前記層に、マスクを介してパターン状に露光する工程(2)、未露光部分をアルカリ現像しパターン状の硬化膜を形成する工程(3)、前記パターンを加熱処理(ポストベーク)する工程(4)を行い作製できる。
[Optical filter manufacturing method]
The method for manufacturing an optical filter includes, for example, a step (1) of applying a photosensitive composition onto a substrate to form a layer (film) of the composition, and a step (2) of exposing the layer to light in a pattern through a mask. ), step (3) of developing the unexposed portion with alkali to form a patterned cured film, and step (4) of heat-treating the pattern (post-baking).
以下、光学フィルタの製造方法を詳細に説明する。
(工程(1))
組成物の層を形成する工程(1)は、感光性組成物を基板上に、例えば、回転塗布、ロ-ル塗布、スリット塗布、流延塗布、またはインクジェット塗布等の方法で塗布し、必要に応じてオーブン、ホットプレート等を用いて、50~120℃の温度で10~120秒乾燥(プリベーク)する。
前記基板は、例えば、ガラス基板、シリコン基板等が挙げられる。シリコン基板は、例えば、表面にCCD、CMOS等の撮像素子が形成されていてもよい。また、基板上には、必要に応じて、上部との層との密着改良、物質の拡散防止、基板表面の平坦化のために下塗り層を設けてもよい。
層の膜厚は、0.05~10.0μmが好ましく、0.3~5μmがより好ましい。
Hereinafter, a method for manufacturing an optical filter will be explained in detail.
(Step (1))
Step (1) of forming a layer of the composition is to apply the photosensitive composition onto the substrate by a method such as spin coating, roll coating, slit coating, cast coating, or inkjet coating, and apply the photosensitive composition as necessary. Dry (prebake) at a temperature of 50 to 120°C for 10 to 120 seconds using an oven, hot plate, etc., depending on the situation.
Examples of the substrate include a glass substrate, a silicon substrate, and the like. For example, an image sensor such as a CCD or CMOS may be formed on the surface of the silicon substrate. Further, an undercoat layer may be provided on the substrate, if necessary, in order to improve adhesion between the upper layer and the layer, to prevent diffusion of substances, and to flatten the surface of the substrate.
The thickness of the layer is preferably 0.05 to 10.0 μm, more preferably 0.3 to 5 μm.
(工程(2))
露光工程は、工程(1)で得られた層を、例えば、ステッパー等の露光装置を用い、マスクを介して特定のパターンを露光する。これにより硬化膜が得られる。
露光に用いる放射線は、例えば、g線、h線、i線等の紫外線が挙げられる。
(Step (2))
In the exposure step, the layer obtained in step (1) is exposed to a specific pattern through a mask using an exposure device such as a stepper. A cured film is thereby obtained.
Examples of the radiation used for exposure include ultraviolet rays such as g-line, h-line, and i-line.
(工程(3))
工程(2)で得られた硬化膜は、アルカリ現像処理を行うことで、未露光部分の組成物の層がアルカリ水溶液に溶出し、硬化部分のみが残りパターン状の硬化膜が得られる。
現像液は、例えば、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム,硅酸ナトリウム、メタ硅酸ナトリウム、アンモニア水、エチルアミン、ジエチルアミン、ジメチルエタノールアミン、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、コリン、ピロ-ル、ピペリジン、1,8-ジアザビシクロ-〔5.4.0〕-7-ウンデセン等のアルカリ性化合物が挙げられる。
現像液の濃度は、0.001~10質量%が好ましく、0.01~1質量%がより好ましい。
アルカリ現像液のpHは、11~13が好ましく、11.5~12.5がより好ましい。適度なpHで使用するとパターンの荒れや剥離を抑制し、現像後の残膜率が向上する。
(Step (3))
The cured film obtained in step (2) is subjected to an alkali development treatment, whereby the unexposed portions of the composition layer are eluted into the alkaline aqueous solution, leaving only the cured portions to form a patterned cured film.
Examples of the developer include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, Examples include alkaline compounds such as pyrrole, piperidine, and 1,8-diazabicyclo-[5.4.0]-7-undecene.
The concentration of the developer is preferably 0.001 to 10% by weight, more preferably 0.01 to 1% by weight.
The pH of the alkaline developer is preferably 11 to 13, more preferably 11.5 to 12.5. When used at an appropriate pH, pattern roughness and peeling can be suppressed and the residual film rate after development can be improved.
現像方法は、例えば、ディップ法、スプレー法、パドール法等が挙げられる。現像温度は15~40℃が好ましい。なお、アルカリ現像後は、純水で洗浄することが好ましい。 Examples of the developing method include a dip method, a spray method, and a paddle method. The developing temperature is preferably 15 to 40°C. Note that after alkaline development, it is preferable to wash with pure water.
(工程(4))
加熱処理(ポストベーク)は、工程(3)で得られたパターン状の硬化膜を加熱により十分に硬化させる。ポストベークの加熱温度は、100~300℃が好ましく、150~250℃がより好ましい。また、加熱時間は、2分間~1時間程度が好ましく、3分間~30分間程度がより好ましい。
(Step (4))
In the heat treatment (post-bake), the patterned cured film obtained in step (3) is sufficiently cured by heating. The heating temperature for post-bake is preferably 100 to 300°C, more preferably 150 to 250°C. Further, the heating time is preferably about 2 minutes to 1 hour, more preferably about 3 minutes to 30 minutes.
<画像表示装置>
本発明の画像表示装置は、本発明の光学フィルタを備える。画像表示装置は、例えば、液晶ディスプレイ、有機ELディスプレイ等が挙げられる。
画像表示装置に用いる形態は、画像表示装置として機能すればよく、特に制限されない。例えば、「次世代液晶ディスプレイ技術(内田龍男著、(株)工業調査会、1994年発行)に記載されている構成等が挙げられる。
画像表示装置の定義や各画像表示装置の詳細については、例えば、「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)、平成元年発行)」等に記載されている。
<Image display device>
The image display device of the present invention includes the optical filter of the present invention. Examples of the image display device include a liquid crystal display and an organic EL display.
The form used for the image display device is not particularly limited as long as it functions as an image display device. For example, the configuration described in "Next Generation Liquid Crystal Display Technology" (written by Tatsuo Uchida, Kogyo Chosenkai Co., Ltd., published in 1994) can be mentioned.
For the definition of an image display device and details of each image display device, see, for example, “Electronic Display Devices (written by Akio Sasaki, Kogyo Chosenkai Co., Ltd., published in 1990)” and “Display Devices (written by Junaki Ibuki, written by Sangyo Tosho)”. Co., Ltd., published in 1989).
<固体撮像素子>
本発明の固体撮像素子は、本発明の光学フィルタを備える。
固体撮像素子に用いる形態は、特に制限されないが、例えば、基材上に、固体撮像素子(CCDイメージセンサ、CMOSイメージセンサ等)の受光エリアを構成する複数のフォトダイオードおよびポリシリコン等からなる転送電極を有し、フォトダイオードおよび転送電極上にフォトダイオードの受光部のみ開口した遮光膜を有し、遮光膜上に遮光膜全面およびフォトダイオード受光部を覆うように形成された窒化シリコン等からなるデバイス保護膜を有し、デバイス保護膜上に、フィルタを有する構成である。さらに、デバイス保護膜上であってフィルタの下(基材に近い側)に集光手段(例えば、マイクロレンズ等。以下同じ)を有する構成や、フィルタ上に集光手段を有する構成等であってもよい。また、フィルタは、隔壁により例えば格子状に仕切られた空間に、各着色画素を形成する硬
化膜が埋め込まれた構造を有していてもよい。この場合の隔壁は、各着色画素に対して低屈折率であることが好ましい。
本発明の固体撮像素子を備えた撮像装置は、例えば、デジタルカメラ、撮像機能を有する電子機器(携帯電話、スマートフォン等)、車載カメラ、監視カメラ等様々な用途に使用できる。
<Solid-state image sensor>
The solid-state image sensor of the present invention includes the optical filter of the present invention.
The form used for the solid-state image sensor is not particularly limited, but for example, a transfer device consisting of a plurality of photodiodes, polysilicon, etc. that constitute the light-receiving area of the solid-state image sensor (CCD image sensor, CMOS image sensor, etc.) on a base material. It has an electrode, has a light-shielding film on the photodiode and transfer electrode with an opening only at the light-receiving part of the photodiode, and is made of silicon nitride or the like formed on the light-shielding film so as to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. It has a device protective film and a filter on the device protective film. Furthermore, there may be a configuration in which a light condensing means (for example, a microlens, etc., the same applies hereinafter) is provided on the device protective film below the filter (on the side closer to the base material), or a configuration in which the condensing means is provided on the filter. It's okay. Further, the filter may have a structure in which a cured film forming each colored pixel is embedded in a space partitioned, for example, in a lattice shape by partition walls. In this case, the partition wall preferably has a low refractive index for each colored pixel.
An imaging device equipped with the solid-state imaging device of the present invention can be used in various applications such as, for example, a digital camera, an electronic device having an imaging function (mobile phone, smart phone, etc.), an in-vehicle camera, a surveillance camera, etc.
以下、実施例で本発明をより具体的に説明する。ただし、本発明はこれらに限定されない。なお、「部」は「質量部」、「%」は「質量%」である。
また、本発明において、不揮発分もしくは不揮発分濃度は、280℃で30分間オーブン静置後の、質量残分をいう。
Hereinafter, the present invention will be explained in more detail with reference to Examples. However, the present invention is not limited to these. Note that "part" means "part by mass" and "%" means "% by mass."
Further, in the present invention, the nonvolatile content or nonvolatile content concentration refers to the mass remaining after standing in an oven at 280°C for 30 minutes.
実施例に先立ち、各測定方法について説明する。 Prior to Examples, each measurement method will be explained.
樹脂の重量平均分子量(Mw)、数平均分子量(Mn)、酸価(mgKOH/g)は、以下の通りである。 The weight average molecular weight (Mw), number average molecular weight (Mn), and acid value (mgKOH/g) of the resin are as follows.
(アルカリ可溶性樹脂、及び分散樹脂の平均分子量)
アルカリ可溶性樹脂、及び分散樹脂の数平均分子量(Mn)、重量平均分子量(Mw)は、Ri検出器を装備したゲルパーミエーションクロマトグラフィー(GPC)で測定した。装置としてHLC-8220GPC(東ソー社製)を用い、分離カラムを2本直列に繋ぎ、両方の充填剤には「TSK-GEL SUPER HZM-N」を2連でつなげて使用し、オーブン温度40℃、溶離液としてテトラヒドロフラン(THF)溶液を用い、流速0.35ml/minで測定した。サンプルは1質量%の上記溶離液からなる溶剤に溶解し、20マイクロリットール注入した。平均分子量は、ポリスチレン換算値である。
(Average molecular weight of alkali-soluble resin and dispersed resin)
The number average molecular weight (Mn) and weight average molecular weight (Mw) of the alkali-soluble resin and the dispersion resin were measured by gel permeation chromatography (GPC) equipped with an Ri detector. HLC-8220GPC (manufactured by Tosoh Corporation) was used as the equipment, two separation columns were connected in series, and the packing material for both was "TSK-GEL SUPER HZM-N" connected in two series, and the oven temperature was 40℃. The measurement was performed at a flow rate of 0.35 ml/min using a tetrahydrofuran (THF) solution as an eluent. The sample was dissolved in a solvent consisting of 1% by mass of the above eluent, and 20 microliters of the solution was injected. The average molecular weight is a polystyrene equivalent value.
(アルカリ可溶性樹脂、及び分散樹脂の酸価)
アルカリ可溶性樹脂、及び分散樹脂溶液0.5~1gに、アセトン80ml及び水10mlを加えて攪拌して均一に溶解させ、0.1mol/LのKOH水溶液を滴定液として、自動滴定装置(「COM-555」平沼産業社製)を用いて滴定し、酸価(mgKOH/g)を測定した。そして、樹脂溶液の酸価と樹脂溶液の不揮発分濃度から、樹脂の不揮発分あたりの酸価を算出した。
(Acid value of alkali-soluble resin and dispersion resin)
Add 80 ml of acetone and 10 ml of water to 0.5 to 1 g of alkali-soluble resin and dispersed resin solution, stir to dissolve uniformly, and use an automatic titration device (COM -555'' (manufactured by Hiranuma Sangyo Co., Ltd.) to measure the acid value (mgKOH/g). Then, the acid value per nonvolatile content of the resin was calculated from the acid value of the resin solution and the nonvolatile content concentration of the resin solution.
(分散樹脂のアミン価)
分散樹脂のアミン価は、ASTM D 2074の方法に準拠し、測定した全アミン価(mgKOH/g)を不揮発分換算した値である。
(Amine value of dispersion resin)
The amine value of the dispersion resin is the value obtained by converting the total amine value (mgKOH/g) measured in accordance with the method of ASTM D 2074 into nonvolatile content.
<着色剤(E)の製造>
(微細化した赤色顔料(E-1))
C.i.ピグメントレッド254を100部、塩化ナトリウム1,200部、及びジエチレングリコール120部をステンレス製1ガロンニーダー(井上製作所社製)中に仕込み、60℃で6時間混練した。次に、混練した混合物を温水に投入し、約80℃に加熱しながらハイスピードミキサーで1時間攪拌してスラリー状として、濾過・水洗をして塩化ナトリウム及びジエチレングリコールを除いた後、80℃で一昼夜乾燥させ、粉砕することにより微細化した赤色顔料(E-1)を得た。
<Production of colorant (E)>
(Fine red pigment (E-1))
C. i. 100 parts of Pigment Red 254, 1,200 parts of sodium chloride, and 120 parts of diethylene glycol were placed in a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 60° C. for 6 hours. Next, the kneaded mixture was poured into hot water, heated to about 80°C and stirred for 1 hour with a high-speed mixer to form a slurry, filtered and washed with water to remove sodium chloride and diethylene glycol, and heated to 80°C. A finely divided red pigment (E-1) was obtained by drying the mixture for one day and crushing it.
(微細化した赤色顔料(E-2))
C.i.ピグメントレッド177を100部、塩化ナトリウム1,200部、及びジエチレングリコール120部をステンレス製1ガロンニーダー(井上製作所社製)中に仕込み、60℃で6時間混練した。次に、混練した混合物を温水に投入し、約80℃に加熱し
ながらハイスピードミキサーで1時間攪拌してスラリー状として、濾過・水洗をして塩化ナトリウム及びジエチレングリコールを除いた後、80℃で一昼夜乾燥させ、粉砕することにより微細化した赤色顔料(E-2)を得た。
(Fine red pigment (E-2))
C. i. 100 parts of Pigment Red 177, 1,200 parts of sodium chloride, and 120 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 60° C. for 6 hours. Next, the kneaded mixture was poured into hot water, heated to about 80°C and stirred with a high-speed mixer for 1 hour to form a slurry, filtered and washed with water to remove sodium chloride and diethylene glycol, and heated to about 80°C. A finely divided red pigment (E-2) was obtained by drying the mixture for one day and crushing it.
(微細化した青色顔料(E-3))
C.I.Pigment Blue15:6を100部、塩化ナトリウム1,000部、およびジエチレングリコール100部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、50℃で12時間混練した。この混合物を温水3,000部に投入し、約70℃に加熱しながらハイスピードミキサーで約1時間攪拌してスラリー状とし、濾過、水洗をくりかえして食塩および溶剤を除いた後、80℃で24時間乾燥し、粉砕することにより微細化した青色顔料(E-3)を得た。
(Finely refined blue pigment (E-3))
C. I. 100 parts of Pigment Blue 15:6, 1,000 parts of sodium chloride, and 100 parts of diethylene glycol were placed in a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.), and kneaded at 50° C. for 12 hours. This mixture was poured into 3,000 parts of warm water, heated to about 70°C and stirred with a high-speed mixer for about 1 hour to form a slurry. After repeated filtration and water washing to remove salt and solvent, the mixture was heated to 80°C. A finely divided blue pigment (E-3) was obtained by drying for 24 hours and pulverizing.
(微細化した紫色顔料(E-4))
C.I.ピグメントバイオレット23を100部、塩化ナトリウム1,200部、およびジエチレングリコール100部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次に、この混練物を8,000部の温水に投入し、80℃に加熱しながらハイスピードミキサーで2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム、およびジエチレングリコールを除いた後、85℃で24時間乾燥し、粉砕することにより微細化した紫色顔料(E-4)を得た。
(Finely refined purple pigment (E-4))
C. I. 100 parts of Pigment Violet 23, 1,200 parts of sodium chloride, and 100 parts of diethylene glycol were placed in a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 80° C. for 6 hours. Next, this kneaded material was poured into 8,000 parts of warm water, stirred for 2 hours with a high-speed mixer while heating to 80°C to form a slurry, and filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol. Thereafter, it was dried at 85° C. for 24 hours and pulverized to obtain a finely divided purple pigment (E-4).
(微細化した緑色顔料(E-5))
C.I.ピグメントグリーン58を100部、塩化ナトリウム1,200部、及びジエチレングリコール120部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、70℃で6時間混練した。この混練物を3000部の温水に投入し、70℃に加熱しながらハイスピードミキサーで1時間撹拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、80℃で一昼夜乾燥し、粉砕することにより微細化した緑色顔料(E-5)を得た。
(Finely divided green pigment (E-5))
C. I. 100 parts of Pigment Green 58, 1,200 parts of sodium chloride, and 120 parts of diethylene glycol were placed in a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho) and kneaded at 70°C for 6 hours. This kneaded material was poured into 3000 parts of warm water, heated to 70°C and stirred for 1 hour with a high-speed mixer to form a slurry. After repeated filtration and water washing to remove sodium chloride and diethylene glycol, the mixture was heated to 80°C overnight. A finely divided green pigment (E-5) was obtained by drying and pulverizing.
(微細化した緑色顔料(E-6)
特開2017-111398号公報の実施例に従って、下記化学式(20)の緑色顔料(E-6)を得た。緑色顔料(E-6)を100部、塩化ナトリウム1,200部、及びジエチレングリコール120部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、70℃で6時間混練した。この混練物を3000部の温水に投入し、70℃に加熱しながらハイスピードミキサーで1時間撹拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、80℃で一昼夜乾燥し、粉砕することにより微細化した緑色顔料(E-6)を得た。
化学式(20)
(Fine green pigment (E-6)
A green pigment (E-6) having the following chemical formula (20) was obtained according to the examples of JP-A-2017-111398. 100 parts of green pigment (E-6), 1,200 parts of sodium chloride, and 120 parts of diethylene glycol were placed in a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho) and kneaded at 70° C. for 6 hours. This kneaded material was poured into 3000 parts of warm water, heated to 70°C and stirred for 1 hour with a high-speed mixer to form a slurry. After repeated filtration and water washing to remove sodium chloride and diethylene glycol, the mixture was heated to 80°C overnight. A finely divided green pigment (E-6) was obtained by drying and pulverizing.
Chemical formula (20)
(微細化した黄色顔料(E-7))
C.I.ピグメントイエロー150を100部、塩化ナトリウム700部、及びジエチレングリコール180部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、80℃で6時間混練した。この混合物を温水2,000部に投入し、80℃に加熱しながらハイスピードミキサーで1時間攪拌してスラリー状とし、濾過、水洗をくりかえして塩化ナトリウム及びジエチレングリコールを除いた後、80℃で一昼夜乾燥し、粉砕することにより微細化した黄色顔料(E-7)を得た。
(Fine yellow pigment (E-7))
C. I. 100 parts of Pigment Yellow 150, 700 parts of sodium chloride, and 180 parts of diethylene glycol were placed in a 1-gallon stainless steel kneader (manufactured by Inoue Seisakusho) and kneaded at 80° C. for 6 hours. This mixture was poured into 2,000 parts of warm water, heated to 80°C and stirred for 1 hour with a high-speed mixer to form a slurry. After repeated filtration and water washing to remove sodium chloride and diethylene glycol, the mixture was heated to 80°C overnight. A finely divided yellow pigment (E-7) was obtained by drying and pulverizing.
(微細化した黄色顔料(E-8))
C.I.ピグメントイエロー139(クラリアント社製「Novoperm Yellow P-M3R」)100部、粉砕した塩化ナトリウム800部、およびジエチレングリコール100部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、70℃で12時間混練した。この混合物を温水3000部に投入し、約70℃に加熱しながらハイスピードミキサーで約1時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウムおよびジエチレングリコールを除いた後、80℃で一昼夜乾燥し、粉砕することにより微細化した黄色顔料(E-8)を得た。
(Fine yellow pigment (E-8))
C. I. 100 parts of Pigment Yellow 139 ("Novoperm Yellow P-M3R" manufactured by Clariant), 800 parts of crushed sodium chloride, and 100 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70°C for 12 hours. . This mixture was poured into 3000 parts of warm water, heated to about 70°C and stirred with a high-speed mixer for about 1 hour to form a slurry. After repeated filtration and water washing to remove sodium chloride and diethylene glycol, the mixture was kept at 80°C overnight. A finely divided yellow pigment (E-8) was obtained by drying and pulverizing.
(微細化した黄色顔料(E-9))
C.I.ピグメントイエロー185(BASFジャパン社製「Palitol Yellow D1155」)100部、粉砕した塩化ナトリウム700部、及びジエチレングリコール180部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8リットルの温水に投入し、80℃に加熱しながらハイスピードミキサーで2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、粉砕することにより微細化した黄色顔料(E-9)を得た。
(Fine yellow pigment (E-9))
C. I. 100 parts of Pigment Yellow 185 ("Palitol Yellow D1155" manufactured by BASF Japan), 700 parts of crushed sodium chloride, and 180 parts of diethylene glycol were placed in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 80°C for 6 hours. . Next, this kneaded material was poured into 8 liters of warm water, stirred for 2 hours with a high-speed mixer while heating to 80°C to form a slurry, and after repeated filtration and water washing to remove sodium chloride and diethylene glycol, the mixture was heated to 85°C. A fine yellow pigment (E-9) was obtained by drying the powder for a day and pulverizing it.
(微細化した黄色顔料(E-10)
特開2012-226110号公報の実施例に従って、下記化学式(21)の黄色顔料(E-10)を得た。黄色顔料(E-10)100部、粉砕した塩化ナトリウム700部、及びジエチレングリコール180部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、80℃で6時間混練した。次にこの混練物を8リットルの温水に投入し、80℃に加熱しながらハイスピードミキサーで2時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、85℃で一昼夜乾燥し、粉砕することにより微細化した黄色顔料(E-10)を得た。
化学式(21)
A yellow pigment (E-10) having the following chemical formula (21) was obtained according to the examples of JP-A-2012-226110. 100 parts of yellow pigment (E-10), 700 parts of pulverized sodium chloride, and 180 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) and kneaded at 80° C. for 6 hours. Next, this kneaded material was poured into 8 liters of warm water, heated to 80°C and stirred for 2 hours with a high-speed mixer to form a slurry, and after repeated filtration and water washing to remove sodium chloride and diethylene glycol, the mixture was heated to 80°C. A fine yellow pigment (E-10) was obtained by drying the powder for a day and pulverizing it.
Chemical formula (21)
上記微細化された顔料の平均一次粒子径は、5~120nmの範囲内であった。 The average primary particle diameter of the finely divided pigment was within the range of 5 to 120 nm.
(染料(E-11))
下記の手順でC.I.アシッド レッド 52と側鎖にカチオン性基を有する樹脂1とからなる造塩化合物である染料(E-11)を製造した。
温度計、攪拌機、蒸留管、冷却器を具備した4つ口セパラブルフラスコに、メチルエチルケトン67.3 部を仕込み窒素気流下で75 ℃ に昇温した。別途、メチルメタクリ
レート34.0部、n-ブチルメタクリレート28.0部、2-エチルヘキシルメタクリレート28.0部、ジメチルアミノエチルメタクリレート10.0部、2,2’-アゾビス(2,4-ジメチルバレロニトリル)を6.5部、およびメチルエチルケトン25.1部を均一にした後、滴下ロートに仕込み、4つ口セパラブルフラスコに取り付け、2時間かけて滴下した。滴下終了2時間後、不揮発分から重合収率が98%以上であり、重量平均分子量(Mw)が、6,830であることを確認し、50℃へ冷却した。ここへ、塩化メチル3.2部、エタノール22.0部を追加し、50℃で2時間反応させた後、1時
間かけて80℃まで加温し、更に、2時間反応させた。このようにして樹脂成分が47質量%のアンモニウム基を有する側鎖にカチオン性基を有する樹脂1を得た。得られた樹脂のアンモニウム塩価は34mgKOH/gであった。
次に、水2,000部に不揮発分換算で30部の側鎖にカチオン性基を有する樹脂1を添加し、十分に攪拌混合を行った後、60℃に加熱した。一方、90部の水に10部のC.I.アシッドレッド 52を溶解させた水溶液を調製し、先ほどの樹脂溶液に少しずつ滴下した。滴下後、60℃で120分間攪拌し、十分に反応を行った。反応の終点確認としては濾紙に反応液を滴下して、にじみがなくなったところを終点として、造塩化合物が得られたものと判断した。攪拌しながら室温まで放冷した後、吸引濾過を行い、水洗後、濾紙上に残った造塩化合物を乾燥機にて水分を除去して乾燥し、32部のC.i.アシッドレッド 52と側鎖にカチオン性基を有する樹脂1との造塩化合物である染料(E-11)を得た。このとき染料(E-11)中のC.I.アシッド レッド 52に由来する成分の含有量は25質量%であった。
(Dye (E-11))
C. by following the steps below. I. A dye (E-11), which is a salt-forming compound consisting of Acid Red 52 and Resin 1 having a cationic group in its side chain, was produced.
67.3 parts of methyl ethyl ketone was charged into a four-neck separable flask equipped with a thermometer, a stirrer, a distillation tube, and a condenser, and the temperature was raised to 75° C. under a nitrogen stream. Separately, 34.0 parts of methyl methacrylate, 28.0 parts of n-butyl methacrylate, 28.0 parts of 2-ethylhexyl methacrylate, 10.0 parts of dimethylaminoethyl methacrylate, 2,2'-azobis(2,4-dimethylvaleronitrile) ) and 25.1 parts of methyl ethyl ketone were homogenized, then charged into a dropping funnel, attached to a four-neck separable flask, and added dropwise over 2 hours. Two hours after the completion of the dropwise addition, it was confirmed that the polymerization yield was 98% or more from nonvolatile components and the weight average molecular weight (Mw) was 6,830, and the mixture was cooled to 50°C. To this, 3.2 parts of methyl chloride and 22.0 parts of ethanol were added and reacted at 50°C for 2 hours, then heated to 80°C over 1 hour, and further reacted for 2 hours. In this way, a resin 1 was obtained in which the resin component had 47% by mass of ammonium groups and a cationic group in the side chain. The ammonium salt value of the obtained resin was 34 mgKOH/g.
Next, 30 parts (calculated as non-volatile content) of Resin 1 having a cationic group in the side chain was added to 2,000 parts of water, the mixture was sufficiently stirred and mixed, and then heated to 60°C. Meanwhile, 10 parts of C.I. I. An aqueous solution in which Acid Red 52 was dissolved was prepared and added dropwise little by little to the resin solution. After the dropwise addition, the mixture was stirred at 60° C. for 120 minutes to fully react. To confirm the end point of the reaction, the reaction solution was dropped onto a filter paper, and the end point was determined to be the end point when there was no bleeding, and it was determined that a salt-forming compound had been obtained. After cooling to room temperature while stirring, suction filtration was performed, and after washing with water, the salt-forming compound remaining on the filter paper was dried by removing moisture in a dryer, and 32 parts of C.I. i. A dye (E-11) which is a salt-forming compound of Acid Red 52 and Resin 1 having a cationic group in its side chain was obtained. At this time, C.I. in the dye (E-11) I. The content of components derived from Acid Red 52 was 25% by mass.
<アルカリ可溶性樹脂(A)の製造>
(アルカリ可溶性樹脂(A1-1)溶液)
撹拌機、温度計、還流冷却管、滴下ロ-トおよび窒素導入管を備えたフラスコに、プロピレングリコールモノメチルエーテルアセテート(以下、PGMAc)333部を導入し、フラスコ内雰囲気を空気から窒素にした後、100℃に昇温後、ベンジルメタクリレート70.5部(0.40モル)、グリシジルメタクリレート71.1部(0.50モル)
、ジシクロペンタニルメタクリレート22.0部(0.10モル)および、PGMAc164部からなる混合物にアゾビスイソブチロニトリル3.6部を添加した溶液を滴下ロ-トから2時間かけてフラスコに滴下し、さらに100℃で5時間撹拌し続けた。次に、フラスコ内雰囲気を窒素から空気にし、メタクリル酸43.0部[0.5モル、(本反応に用いたグリシジルメタクリレートのグリシジル基に対して100モル%)]、トリスジメチルアミノメチルフェノール0.9部およびハイドロキノン0.145部をフラスコ内に投入し、110℃で6時間反応を続け不揮発分酸価が1mgKOH/gとなったところで反応を終了した。次に、テトラヒドロフタル無水フタル酸60.9部(0.40モル)、トリエチルアミン0.8部を加え、120℃で3.5時間反応させ酸価80mgKOH/gの感光性の樹脂溶液を得た。室温まで冷却した後、感光性の樹脂溶液約2部をサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した感光性の樹脂溶液に不揮発分が20質量%になるようにPGMAcを添加して、脂環式炭化水素含有単量体単位(a1)、及びカルボキシル基含有単量体単位(a2)を含有する感光性のアルカリ可溶性樹脂(A1-1)溶液を調製した。重量平均分子量(Mw)は12,000であった。
<Production of alkali-soluble resin (A)>
(Alkali-soluble resin (A1-1) solution)
333 parts of propylene glycol monomethyl ether acetate (hereinafter referred to as PGMAc) was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube, and the atmosphere inside the flask was changed from air to nitrogen. , after heating to 100°C, 70.5 parts (0.40 mol) of benzyl methacrylate, 71.1 parts (0.50 mol) of glycidyl methacrylate.
, 22.0 parts (0.10 mol) of dicyclopentanyl methacrylate, and 164 parts of PGMAc, and 3.6 parts of azobisisobutyronitrile were added to the flask from the dropping funnel over 2 hours. The mixture was added dropwise, and stirring was continued at 100° C. for 5 hours. Next, the atmosphere inside the flask was changed from nitrogen to air, and 43.0 parts of methacrylic acid [0.5 mol, (100 mol% based on the glycidyl group of glycidyl methacrylate used in this reaction)], trisdimethylaminomethylphenol 0 .9 parts and 0.145 parts of hydroquinone were put into the flask, and the reaction was continued at 110° C. for 6 hours, and the reaction was terminated when the nonvolatile acid value reached 1 mgKOH/g. Next, 60.9 parts (0.40 mol) of tetrahydrophthalic anhydride and 0.8 parts of triethylamine were added and reacted at 120°C for 3.5 hours to obtain a photosensitive resin solution with an acid value of 80 mgKOH/g. . After cooling to room temperature, approximately 2 parts of the photosensitive resin solution was sampled and dried by heating at 180°C for 20 minutes to measure the nonvolatile content. PGMAc was added to prepare a photosensitive alkali-soluble resin (A1-1) solution containing an alicyclic hydrocarbon-containing monomer unit (a1) and a carboxyl group-containing monomer unit (a2). Prepared. The weight average molecular weight (Mw) was 12,000.
(アルカリ可溶性樹脂(A1-2)溶液)
撹拌機、温度計、還流冷却管、滴下ロ-トおよび窒素導入管を備えたフラスコに、PGMAc182部を導入し、フラスコ内雰囲気を空気から窒素にした後、100℃に昇温後
、ベンジルメタクリレート70.5部(0.40モル)、メタクリル酸43.0部(0.5モル)、ジシクロペンタニルメタクリレート22.0部(0.10モル)およびPGMAc136部からなる混合物にアゾビスイソブチロニトリル3.6部を添加した溶液を滴下ロ-トから2時間かけてフラスコに滴下し、さらに100℃で5時間撹拌し続けた。次に、フラスコ内雰囲気を窒素から空気にし、グリシジルメタクリレート35.5部[0.25モル、(本反応に用いたメタクリル酸のカルボキシル基に対して50モル%)]、トリスジメチルアミノメチルフェノール0.9部およびハイドロキノン0.145部をフラスコ内に投入し、110℃で6時間反応を続け、酸価が79mgKOH/gの感光性の樹脂溶液を得た。室温まで冷却した後、感光性の樹脂溶液約2部をサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した感光性の透明樹脂溶液に不揮発分が20質量%になるようにPGMAcを添加して、脂環式炭化水素含有単量体単位(a1)、及びカルボキシル基含有単量体単位(a2)を含有する感光性のアルカリ可溶性樹脂(A1-2)溶液を調製した。重量平均分子量(Mw)は13,000であった。
(Alkali-soluble resin (A1-2) solution)
182 parts of PGMAc was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. After changing the atmosphere inside the flask from air to nitrogen, the temperature was raised to 100°C, and benzyl methacrylate was added. 70.5 parts (0.40 mol) of methacrylic acid, 43.0 parts (0.5 mol) of methacrylic acid, 22.0 parts (0.10 mol) of dicyclopentanyl methacrylate, and 136 parts of PGMAc were mixed with azobisisobutylene. A solution containing 3.6 parts of lonitrile was added dropwise from the dropping funnel to the flask over 2 hours, and the mixture was further stirred at 100° C. for 5 hours. Next, the atmosphere inside the flask was changed from nitrogen to air, and 35.5 parts of glycidyl methacrylate [0.25 mol, (50 mol % based on the carboxyl group of methacrylic acid used in this reaction)] and 0 parts of trisdimethylaminomethylphenol were added. .9 parts and 0.145 parts of hydroquinone were put into the flask, and the reaction was continued at 110° C. for 6 hours to obtain a photosensitive resin solution with an acid value of 79 mgKOH/g. After cooling to room temperature, approximately 2 parts of the photosensitive resin solution was sampled and dried by heating at 180°C for 20 minutes to measure the nonvolatile content. A photosensitive alkali-soluble resin (A1-2) solution containing an alicyclic hydrocarbon-containing monomer unit (a1) and a carboxyl group-containing monomer unit (a2) by adding PGMAc so that was prepared. The weight average molecular weight (Mw) was 13,000.
(アルカリ可溶性樹脂(A2-1)溶液)
セパラブル4口フラスコに温度計、冷却管、窒素ガス導入管、滴下管および撹拌装置を取り付けた反応容器にシクロヘキサノン196部を仕込み、80℃に昇温し、反応容器内を窒素置換した後、滴下管より、n-ブチルメタクリレート37.2部、2-ヒドロキシエチルメタクリレート12.9部、メタクリル酸12.0部、パラクミルフェノールエチレンオキサイド変性アクリレート(東亞合成社製「アロニックスM110」)20.7部、2,2’-アゾビスイソブチロニトリル1.1部の混合物を2時間かけて滴下した。滴下終了後、更に3時間反応を継続し、アクリル樹脂の溶液を得た。室温まで冷却した後、樹脂溶液約2部をサンプリングして180℃、20分間加熱乾燥して不揮発分を測定し、先に合成した樹脂溶液に不揮発分が20質量%になるようにPGMAcを添加して、非感光性のアルカリ可溶性樹脂(A2-1)溶液を調製した。重量平均分子量(Mw)は26,000であった。
(Alkali-soluble resin (A2-1) solution)
196 parts of cyclohexanone was placed in a separable 4-neck flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube, and a stirring device. 196 parts of cyclohexanone was then heated to 80°C, the inside of the reaction vessel was replaced with nitrogen, and then added dropwise. From the tube, 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, 20.7 parts of paracumylphenol ethylene oxide modified acrylate ("Aronix M110" manufactured by Toagosei Co., Ltd.) A mixture of 1.1 parts of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours. After the dropwise addition was completed, the reaction was continued for an additional 3 hours to obtain an acrylic resin solution. After cooling to room temperature, about 2 parts of the resin solution was sampled and heated and dried at 180°C for 20 minutes to measure the nonvolatile content, and PGMAc was added to the previously synthesized resin solution so that the nonvolatile content was 20% by mass. A non-photosensitive alkali-soluble resin (A2-1) solution was prepared. The weight average molecular weight (Mw) was 26,000.
(アルカリ可溶性樹脂(A2-2)溶液)
セパラブル4口フラスコに温度計、冷却管、窒素ガス導入管、滴下管及び撹拌装置を取り付けた反応容器にシクロヘキサノン207部を仕込み、80℃に昇温し、反応容器内を窒素置換した後、滴下管より、メタクリル酸20部、ベンジルメタクリレート20部、パラクミルフェノールエチレンオキサイド変性アクリレート(東亞合成社製アロニックスM110)20部、メタクリル酸メチル25部、2-ヒドロキシエチルメタクリレート8.5部、及び2,2'-アゾビスイソブチロニトリル1.33部の混合物を2時間かけて滴下
した。滴下終了後、更に3時間反応を継続し、共重合体樹脂溶液を得た。次に得られた共重合体溶液全量に対して、窒素ガスを停止し乾燥空気を1時間注入しながら攪拌したのちに、室温まで冷却した後、2-メタクリロイルオキシエチルイソシアネート(昭和電工社製カレンズMOI)6.5部、ラウリン酸ジブチル錫0.08部、シクロヘキサノン26部の混合物を70℃で3時間かけて滴下した。滴下終了後、更に1時間反応を継続し、樹脂の溶液を得た不揮発分が20質量%になるようにシクロヘキサノンを添加して、感光性のアルカリ可溶性樹脂(A2-2)溶液を調製した。重量平均分子量(Mw)は18,000であり、不揮発分酸価が130mgKOH/gであった。
(Alkali-soluble resin (A2-2) solution)
207 parts of cyclohexanone was placed in a separable 4-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube, and a stirring device. 207 parts of cyclohexanone was heated to 80°C, the inside of the reaction vessel was replaced with nitrogen, and then added dropwise. From the tube, 20 parts of methacrylic acid, 20 parts of benzyl methacrylate, 20 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110, manufactured by Toagosei Co., Ltd.), 25 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 2, A mixture of 1.33 parts of 2'-azobisisobutyronitrile was added dropwise over 2 hours. After the dropwise addition was completed, the reaction was continued for an additional 3 hours to obtain a copolymer resin solution. Next, the entire amount of the obtained copolymer solution was stirred while stopping nitrogen gas and injecting dry air for 1 hour. After cooling to room temperature, 2-methacryloyloxyethyl isocyanate (Karens A mixture of 6.5 parts of MOI), 0.08 parts of dibutyltin laurate, and 26 parts of cyclohexanone was added dropwise at 70° C. over 3 hours. After the dropwise addition was completed, the reaction was continued for another 1 hour, and cyclohexanone was added so that the nonvolatile content of the resin solution was 20% by mass to prepare a photosensitive alkali-soluble resin (A2-2) solution. The weight average molecular weight (Mw) was 18,000, and the nonvolatile acid value was 130 mgKOH/g.
<分散樹脂(G)の製造>
(分散樹脂(G-1)溶液)
ガス導入管、温度、コンデンサー、攪拌機を備えた反応容器に、メタクリル酸10部、メチルメタクリレート100部、i-ブチルメタクリレート70部、ベンジルメタクリレート20部、PGMAc50部を仕込み、窒素ガスで置換した。反応容器内を50℃に加熱撹拌し、3-メルカプト-1,2-プロパンジオール12部を添加した。90℃に昇温し、2,2’-アゾビスイソブチロニトリル0.1部をPGMAc90部に加えた溶液を
添加しながら7時間反応した。不揮発分測定により95%が反応したことを確認した。ピロメリット酸無水物19部、PGMAc50部、シクロヘキサノン50部、触媒として1,8-ジアザビシクロ-[5.4.0]-7-ウンデセン0.4部を追加し、100℃で7時間反応させた。酸価の測定で98%以上の酸無水物がハーフエステル化していることを確認し反応を終了し、不揮発分測定で不揮発分30%となるようPGMAcを加えて希釈し、酸価70mgKOH/g、重量平均分子量8,500の分散樹脂(G-1)溶液を得た。
<Manufacture of dispersed resin (G)>
(Dispersion resin (G-1) solution)
A reaction vessel equipped with a gas inlet tube, temperature, condenser, and stirrer was charged with 10 parts of methacrylic acid, 100 parts of methyl methacrylate, 70 parts of i-butyl methacrylate, 20 parts of benzyl methacrylate, and 50 parts of PGMAc, and the mixture was purged with nitrogen gas. The inside of the reaction vessel was heated and stirred at 50°C, and 12 parts of 3-mercapto-1,2-propanediol was added. The temperature was raised to 90°C, and a reaction was carried out for 7 hours while adding a solution of 0.1 part of 2,2'-azobisisobutyronitrile to 90 parts of PGMAc. It was confirmed by non-volatile content measurement that 95% had reacted. 19 parts of pyromellitic anhydride, 50 parts of PGMAc, 50 parts of cyclohexanone, and 0.4 part of 1,8-diazabicyclo-[5.4.0]-7-undecene as a catalyst were added and reacted at 100°C for 7 hours. . After confirming that 98% or more of the acid anhydride was half-esterified by measuring the acid value, the reaction was terminated, and the mixture was diluted with PGMAc so that the non-volatile content was 30% by measuring the non-volatile content, and the acid value was 70 mgKOH/g. A dispersion resin (G-1) solution having a weight average molecular weight of 8,500 was obtained.
(分散樹脂(G-2)溶液)
ガス導入管、温度計、コンデンサー、攪拌機を備えた反応容器に、1-チオグリセロール108部、ピロメリット酸無水物174部、PGMAc650部、触媒としてモノブチルスズオキシド0.2部を仕込み、窒素ガスで置換した後、120℃で5時間反応させた(第一工程)。酸価の測定で95%以上の酸無水物がハーフエステル化していることを確認した。次に、第一工程で得られた化合物を不揮発分換算で160部、2-ヒドロキシプロピルメタクリレート200部、エチルアクリレート200部、t-ブチルアクリレート150部、2-メトキシエチルアクリレート200部、メチルアクリレート200部、メタクリル酸50部、PGMAc663部を仕込み、反応容器内を80℃に加熱して、2,2’-アゾビス(2,4-ジメチルバレロニトリル)1.2部を添加し、12時間反応した(第二工程)。不揮発分測定により95%が反応したことを確認した。最後に、第二工程で得られた化合物の不揮発分50%のPGMAc希釈溶液を500部、2-メタクリロイルオキシエチルイソシアネート(MOi)27.0部、ヒドロキノン0.1部を仕込み、IRにてイソシアネート基に基づく2270cm-1のピークの消失を確認するまで反応を行った(第三工程)。ピーク消失の確認後、反応溶液を冷却して、PGMAcで不揮発分調整することにより不揮発分30%の分散樹脂(G-2)溶液を得た。得られた分散樹脂(G-2)の酸価は68mgKOH/g、不飽和二重結合当量は1,593、重量平均分子量は13,000であった。
(Dispersion resin (G-2) solution)
108 parts of 1-thioglycerol, 174 parts of pyromellitic anhydride, 650 parts of PGMAc, and 0.2 parts of monobutyltin oxide as a catalyst were charged into a reaction vessel equipped with a gas inlet tube, a thermometer, a condenser, and a stirrer, and the mixture was heated with nitrogen gas. After the substitution, the mixture was reacted at 120° C. for 5 hours (first step). Acid value measurement confirmed that 95% or more of the acid anhydride was half-esterified. Next, 160 parts of the compound obtained in the first step in terms of nonvolatile content, 200 parts of 2-hydroxypropyl methacrylate, 200 parts of ethyl acrylate, 150 parts of t-butyl acrylate, 200 parts of 2-methoxyethyl acrylate, and 200 parts of methyl acrylate. 1 part, 50 parts of methacrylic acid, and 663 parts of PGMAc were charged, the inside of the reaction vessel was heated to 80°C, 1.2 parts of 2,2'-azobis(2,4-dimethylvaleronitrile) was added, and the mixture was reacted for 12 hours. (Second step). It was confirmed by non-volatile content measurement that 95% had reacted. Finally, 500 parts of a PGMAc diluted solution of the compound obtained in the second step with a non-volatile content of 50%, 27.0 parts of 2-methacryloyloxyethyl isocyanate (MOi), and 0.1 part of hydroquinone were added, and the isocyanate was prepared using IR. The reaction was continued until the disappearance of the peak at 2270 cm −1 based on the group was confirmed (third step). After confirming the disappearance of the peak, the reaction solution was cooled and the nonvolatile content was adjusted with PGMAc to obtain a dispersion resin (G-2) solution with a nonvolatile content of 30%. The resulting dispersed resin (G-2) had an acid value of 68 mgKOH/g, an unsaturated double bond equivalent of 1,593, and a weight average molecular weight of 13,000.
(分散樹脂(G-3)溶液)
ガス導入管、コンデンサー、攪拌翼、及び温度計を備え付けた反応装置に、メチルメタクリレート30部、nーブチルメタクリレート30部、ヒドロキシエチルメタクリレート20部、テトラメチルエチレンジアミン13.2部を仕込み、窒素を流しながら50℃で1時間撹拌し、系内を窒素置換した。次に、ブロモイソ酪酸エチル9.3部、塩化第一銅5.6部、PGMAc133部を仕込み、窒素気流下で、110℃まで昇温して第一ブロック(Bブロック)の重合を開始した。4時間重合後、重合溶液をサンプリングして不揮発分測定を行い、不揮発分から換算して重合転化率が98%以上であることを確認した。
次に、この反応装置に、PGMAc61部、第二ブロック(Aブロック)モノマーとして1,2,2,6,6-ペンタメチルピペリジルメタクリレート20部(日立化成工業社製、ファンクリルFA-711MM)を投入し、110℃・窒素雰囲気下を保持したまま撹拌し、反応を継続した。1,2,2,6,6-ペンタメチルピペリジルメタクリレート投入から2時間後、重合溶液をサンプリングして不揮発分測定を行い、不揮発分から換算して第二ブロック(Aブロック)の重合転化率が98%以上であることを確認し、反応溶液を室温まで冷却して重合を停止した。不揮発分測定で不揮発分30%となるようPGMAcを加えて希釈し、不揮発分当たりのアミン価が57mgKOH/g、数平均分子量4,500(Mn)の分散樹脂(G-3)溶液を得た。
(Dispersion resin (G-3) solution)
30 parts of methyl methacrylate, 30 parts of n-butyl methacrylate, 20 parts of hydroxyethyl methacrylate, and 13.2 parts of tetramethylethylenediamine were charged into a reaction apparatus equipped with a gas inlet pipe, a condenser, a stirring blade, and a thermometer, and the mixture was flushed with nitrogen. The mixture was stirred at 50° C. for 1 hour while the system was purged with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate, 5.6 parts of cuprous chloride, and 133 parts of PGMAc were charged, and the temperature was raised to 110° C. under a nitrogen stream to start polymerization of the first block (B block). After 4 hours of polymerization, the polymerization solution was sampled and the nonvolatile content was measured, and it was confirmed that the polymerization conversion rate was 98% or more as calculated from the nonvolatile content.
Next, 61 parts of PGMAc and 20 parts of 1,2,2,6,6-pentamethylpiperidyl methacrylate (manufactured by Hitachi Chemical Co., Ltd., Fancryl FA-711MM) were added to this reactor. The reaction was continued by stirring while maintaining the temperature at 110° C. and nitrogen atmosphere. Two hours after adding 1,2,2,6,6-pentamethylpiperidyl methacrylate, the polymerization solution was sampled and the non-volatile content was measured, and the polymerization conversion rate of the second block (A block) was 98 in terms of non-volatile content. % or more, the reaction solution was cooled to room temperature to stop the polymerization. PGMAc was added and diluted so that the nonvolatile content was 30% as determined by nonvolatile content measurement, to obtain a dispersion resin (G-3) solution with an amine value per nonvolatile content of 57 mgKOH/g and a number average molecular weight of 4,500 (Mn). .
(分散樹脂(G-4)溶液)
冷却管、添加用ロート、窒素用インレット、機械的攪拌機、デジタル温度計を備えた500mL丸底4口セパラブルフラスコに、テトラヒドロフラン(THF)250質量部及び開始剤のジメチルケテンメチルトリメチルシリルアセタール5.81質量部を、添加用ロートを介して加え、充分に窒素置換を行った。触媒のテトラブチルアンモニウムm-ク
ロロベンゾエートの1モル/Lアセトニトリル溶液0.5質量部を、シリンジを用いて注入し、親溶剤性を有するブロック用モノマーのメタクリル酸2-ヒドロキシエチル19.7質量部、メタクリル酸2-エチルヘキシル7.5質量部、メタクリル酸n-ブチル12.9質量部、メタクリル酸ベンジル10.7質量部、メタクリル酸メチル30.9質量部を、添加用ロートを用いて60分かけて滴下した。反応フラスコを氷浴で冷却することにより、温度を40℃未満に保った。1時間後、色材吸着機能ブロック用モノマーであるジメチルアミノプロピルメタクリルアミド18.3質量部を20分かけて滴下した。1時間反応させた後、メタノール1質量部を加えて反応を停止させた。得られたブロック共重合体THF溶液はヘキサン中で再沈殿させ、濾過、真空乾燥により精製を行った。
続いて、100mL丸底フラスコ中でPGMAc35質量部に、得られたブロック共重合体15.0質量部を溶解させ、塩形成成分であるフェニルホスフィン酸1.1質量部(ジメチルアミノプロピルメタクリルアミドに対し、0.5モル等量)加え、反応温度30℃で20時間攪拌し、PGMAcを添加して調整し、不揮発分30%の分散樹脂(G-4)溶液を得た。
(Dispersion resin (G-4) solution)
In a 500 mL round-bottomed 4-neck separable flask equipped with a condenser, an addition funnel, a nitrogen inlet, a mechanical stirrer, and a digital thermometer, 250 parts by mass of tetrahydrofuran (THF) and 5.81 parts of dimethylketenemethyltrimethylsilyl acetal as an initiator were added. Parts by mass were added via the addition funnel, and the mixture was sufficiently purged with nitrogen. Using a syringe, 0.5 parts by mass of a 1 mol/L acetonitrile solution of tetrabutylammonium m-chlorobenzoate as a catalyst was injected, and 19.7 parts by mass of 2-hydroxyethyl methacrylate, a blocking monomer having solvent affinity, was added. , 7.5 parts by mass of 2-ethylhexyl methacrylate, 12.9 parts by mass of n-butyl methacrylate, 10.7 parts by mass of benzyl methacrylate, and 30.9 parts by mass of methyl methacrylate were added using an addition funnel for 60 minutes. It dripped. The temperature was kept below 40°C by cooling the reaction flask with an ice bath. After 1 hour, 18.3 parts by mass of dimethylaminopropyl methacrylamide, which is a monomer for a colorant adsorption functional block, was added dropwise over 20 minutes. After reacting for 1 hour, 1 part by mass of methanol was added to stop the reaction. The obtained block copolymer THF solution was reprecipitated in hexane, and purified by filtration and vacuum drying.
Subsequently, 15.0 parts by mass of the obtained block copolymer was dissolved in 35 parts by mass of PGMAc in a 100 mL round bottom flask, and 1.1 parts by mass of phenylphosphinic acid (dimethylaminopropyl methacrylamide), which is a salt forming component, was dissolved in 35 parts by mass of PGMAc. The mixture was stirred at a reaction temperature of 30° C. for 20 hours, and adjusted by adding PGMAc to obtain a dispersion resin (G-4) solution with a nonvolatile content of 30%.
<重合性化合物(B)の製造>
(ウレタン結合を有する重合性化合物(B3-1)溶液)
撹拌機、還流冷却管、窒素導入管、温度計、滴下管を備えた5口フラスコに、ジペンタエリスリトールペンタアクリレート400部、PGMAc100部、N,N-ジメチルベンジルアミン0.5部を仕込み、70℃に昇温し、滴下管からトルエンジイソシアネート66部とPGMAc66部の混合物を2時間かけて滴下した。滴下後、50~70℃の温度で8時間反応させ、IRにより2180cm-1のイソシアネートの吸収の消失を確認
した。ついで、メルカプト酢酸35部、4-メトキシフェノール0.6部を仕込み、50~60℃の温度で6時間反応させた。不揮発分が50質量%となるように調整し、ウレタン結合を有する重合性化合物(B3-1)溶液を得た。
<Production of polymerizable compound (B)>
(Polymerizable compound (B3-1) solution having urethane bond)
Into a 5-necked flask equipped with a stirrer, reflux condenser, nitrogen inlet tube, thermometer, and dropping tube, 400 parts of dipentaerythritol pentaacrylate, 100 parts of PGMAc, and 0.5 part of N,N-dimethylbenzylamine were charged. The temperature was raised to .degree. C., and a mixture of 66 parts of toluene diisocyanate and 66 parts of PGMAc was added dropwise from a dropping tube over 2 hours. After the dropwise addition, the mixture was reacted for 8 hours at a temperature of 50 to 70°C, and the disappearance of isocyanate absorption at 2180 cm -1 was confirmed by IR. Then, 35 parts of mercaptoacetic acid and 0.6 parts of 4-methoxyphenol were charged, and the mixture was reacted at a temperature of 50 to 60°C for 6 hours. The nonvolatile content was adjusted to 50% by mass to obtain a solution of a polymerizable compound (B3-1) having a urethane bond.
<分散体の製造>
(分散体1)
下記の原料を均一になるように攪拌混合した後、直径0.5mmのジルコニアビ-ズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM-250 MKii」)で3時間分散した後、孔径1.0μmのフィルタで濾過し、分散体1を作製した。有機溶剤(P-1)は、PGMAcである。
微細化した青色顔料(E-3) :9.05質量部
微細化した紫色顔料(E-4) :0.31質量部
染料(E-11) :4.16質量部
色素誘導体(F-1) :1.04質量部
分散樹脂(G-1)溶液 :3.47質量部
アルカリ可溶性樹脂(A2-1)溶液 :2.00質量部
有機溶剤(P-1) :79.97質量部
<Production of dispersion>
(Dispersion 1)
After stirring and mixing the following raw materials so that they were uniform, they were dispersed for 3 hours using an Eiger mill (“Mini Model M-250 MKii” manufactured by Eiger Japan) using zirconia beads with a diameter of 0.5 mm. The mixture was filtered through a 1.0 μm filter to produce Dispersion 1. The organic solvent (P-1) is PGMAc.
Fine blue pigment (E-3): 9.05 parts by mass Fine purple pigment (E-4): 0.31 parts by mass Dye (E-11): 4.16 parts by mass Pigment derivative (F-1) ): 1.04 parts by mass Dispersion resin (G-1) solution: 3.47 parts by mass Alkali-soluble resin (A2-1) solution: 2.00 parts by mass Organic solvent (P-1): 79.97 parts by mass
色素誘導体(F-1):下記構造
pcは、フタロシアニン骨格を表す。
Pigment derivative (F-1): structure below
pc represents a phthalocyanine skeleton.
表1に記載した原料、量を変えた以外は、分散体1と同様に分散体2~9を作成した。 Dispersions 2 to 9 were prepared in the same manner as Dispersion 1, except that the raw materials and amounts listed in Table 1 were changed.
表1の色素誘導体(F-2):下記構造
表1の色素誘導体(F-3):下記構造
Dye derivative (F-3) in Table 1: Structure below
<感光性組成物の製造>
[実施例1]
(感光性組成物1)
以下の原料を混合、攪拌し、孔径1.0μmのフィルタで濾過して感光性着色組成物1を
得た。
分散体1 :28.85質量部
アルカリ可溶性樹脂(A1-1)溶液 :10.00質量部
重合性化合物(B1-1) :3.00質量部
重合性化合物(B2-1) :3.00質量部
重合性化合物(B3-1)溶液 :2.00質量部
オキシム系光重合開始剤(C1-1) :0.50質量部
オキシム系光重合開始剤(C2-6) :0.50質量部
チオール系連鎖移動剤(D) :0.35質量部
熱硬化性化合物(i) :0.50質量部
重合禁止剤(J) :0.01質量部
レベリング剤(M) :1.00質量部
有機溶剤(P) :50.29質量部
<Manufacture of photosensitive composition>
[Example 1]
(Photosensitive composition 1)
The following raw materials were mixed, stirred, and filtered through a filter with a pore size of 1.0 μm to obtain photosensitive coloring composition 1.
Dispersion 1: 28.85 parts by mass Alkali-soluble resin (A1-1) solution: 10.00 parts by mass Polymerizable compound (B1-1): 3.00 parts by mass Polymerizable compound (B2-1): 3.00 Parts by mass Polymerizable compound (B3-1) solution: 2.00 parts by mass Oxime photoinitiator (C1-1): 0.50 parts by mass Oxime photoinitiator (C2-6): 0.50 parts by mass Thiol chain transfer agent (D): 0.35 parts by mass Thermosetting compound (i): 0.50 parts by mass
Polymerization inhibitor (J): 0.01 parts by mass Leveling agent (M): 1.00 parts by mass Organic solvent (P): 50.29 parts by mass
[実施例2~35、比較例1~3]
(感光性組成物2~38)
実施例1の感光性組成物1を、表2-1~表2-4に記載した原料、量に変えた以外は、実施例1と同様にして感光性組成物2~38を作製した。
[Examples 2 to 35, Comparative Examples 1 to 3]
(Photosensitive compositions 2 to 38)
Photosensitive compositions 2 to 38 were prepared in the same manner as in Example 1, except that the raw materials and amounts of Photosensitive composition 1 in Example 1 were changed to those listed in Tables 2-1 to 2-4.
表2-1~表2-4に記載したそれぞれの原料については、以下の通りである。 The raw materials listed in Tables 2-1 to 2-4 are as follows.
[重合性化合物(B)]
(ラクトン変性された重合性化合物(B1))
B1-1:KAYARAD DPCA-30(日本化薬社製)
[Polymerizable compound (B)]
(Lactone-modified polymerizable compound (B1))
B1-1: KAYARAD DPCA-30 (manufactured by Nippon Kayaku Co., Ltd.)
(酸基を有する重合性化合物(B2))
B2-1:アロニックスM-520(東亞合成社製)
(Polymerizable compound (B2) having an acid group)
B2-1: Aronix M-520 (manufactured by Toagosei Co., Ltd.)
(その他重合性化合物(B4))
B4-1:アロニックスM-420(東亜合成社製)
(Other polymerizable compounds (B4))
B4-1: Aronix M-420 (manufactured by Toagosei Co., Ltd.)
[光重合開始剤(C)]
(オキシム系光重合開始剤(C1))
C1-1:上述の化学式(2)の化合物
C1-2:上述の化学式(3)の化合物
C1-3:上述の化学式(4)の化合物
C1-4:上述の化学式(5)の化合物
C1-5:上述の化学式(6)の化合物
C1-6:上述の化学式(7)の化合物
[Photopolymerization initiator (C)]
(Oxime photopolymerization initiator (C1))
C1-1: Compound of the above chemical formula (2) C1-2: Compound of the above chemical formula (3) C1-3: Compound of the above chemical formula (4) C1-4: Compound of the above chemical formula (5) C1- 5: Compound of the above chemical formula (6) C1-6: Compound of the above chemical formula (7)
(オキシム系光重合開始剤(C2))
C2-1:上述の化学式(8)の化合物
C2-2:上述の化学式(9)の化合物
C2-3:上述の化学式(10)の化合物
C2-4:上述の化学式(11)の化合物
C2-5:上述の化学式(12)の化合物
C2-6:上述の化学式(13)の化合物
C2-7:上述の化学式(14)の化合物
C2-8:上述の化学式(15)の化合物
C2-9:上述の化学式(16)の化合物
(Oxime-based photopolymerization initiator (C2))
C2-1: Compound of the above chemical formula (8) C2-2: Compound of the above chemical formula (9) C2-3: Compound of the above chemical formula (10) C2-4: Compound of the above chemical formula (11) C2- 5: Compound of the above chemical formula (12) C2-6: Compound of the above chemical formula (13) C2-7: Compound of the above chemical formula (14) C2-8: Compound of the above chemical formula (15) C2-9: Compound of the above chemical formula (16)
(その他光重合開始剤(C3))
C3-1:Omnirad 907(IGM Resins社製、アセトフェノン系光重合開始剤)
(Other photopolymerization initiators (C3))
C3-1: Omnirad 907 (manufactured by IGM Resins, acetophenone photopolymerization initiator)
[チオール系連鎖移動剤(D)]
D-1:トリメチロ-ルプロパントリス(3-メルカプトブチレート)
D-2:ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)
以上、(D-1)及び(D-2)をそれぞれ同量にて混合し、チオール系連鎖移動剤(D)とした。
[Thiol chain transfer agent (D)]
D-1: Trimethylolpropane tris (3-mercaptobutyrate)
D-2: Pentaerythritol tetrakis (3-mercaptopropionate)
As described above, (D-1) and (D-2) were mixed in the same amount to prepare a thiol-based chain transfer agent (D).
[増感剤(H)]
H-1:カヤキュアDETX-S(日本化薬社製、チオキサントン系化合物)
H-2:CHEMARK DEABP(Chemark Chemical社製、ベンゾフェノン系化合物)
以上、(H-1)及び(H-2)をそれぞれ同量にて混合し、増感剤(H)とした。
[Sensitizer (H)]
H-1: Kayacure DETX-S (manufactured by Nippon Kayaku Co., Ltd., thioxanthone compound)
H-2: CHEMARK DEABP (manufactured by Chemark Chemical, benzophenone compound)
As described above, (H-1) and (H-2) were mixed in the same amount to prepare a sensitizer (H).
[熱硬化性化合物(I)]
(エポキシ化合物(I1))
I1-1:EHPE-3150(ダイセル社製)
I1-2: デナコールEX611(ナガセケムテックス社製)
I1-3:イソシアヌル酸トリグリシジル
以上、(I1-1)~(I1-3)をそれぞれ同量混合し、熱硬化性化合物(I)とした。
[Thermosetting compound (I)]
(Epoxy compound (I1))
I1-1: EHPE-3150 (manufactured by Daicel)
I1-2: Denacol EX611 (manufactured by Nagase ChemteX)
I1-3: Triglycidyl Isocyanurate The above (I1-1) to (I1-3) were mixed in equal amounts to prepare a thermosetting compound (I).
[重合禁止剤(J)]
J-1:4-メチルカテコール
J-2:メチルヒドロキノン
J-3:t-ブチルヒドロキノン
以上、(J-1)~(J-3)をそれぞれ同量にて混合し、重合禁止剤(J)とした。
[Polymerization inhibitor (J)]
J-1: 4-methylcatechol J-2: Methylhydroquinone J-3: t-butylhydroquinone The above (J-1) to (J-3) were mixed in the same amount, and polymerization inhibitor (J) was added. And so.
[レベリング剤(M)]
M-1:BYK-330(ビックケミー社製)
M-2:メガファックF-551(DIC社製)
以上、(M-1)及び(M-2)をそれぞれ1部混合し、PGMAc98部に溶解させ
た混合溶液をレベリング剤(M)とした。
[Leveling agent (M)]
M-1: BYK-330 (manufactured by BYK Chemie)
M-2: Megafac F-551 (manufactured by DIC)
A mixed solution in which 1 part each of (M-1) and (M-2) were mixed and dissolved in 98 parts of PGMAc was used as a leveling agent (M).
[有機溶剤(P) ]
P-1:プロピレングリコールモノメチルエーテルアセテート 30部
P-2:シクロヘキサノン 30部
P-3:3-エトキシプロピオン酸エチル 10部
P-4:プロピレングリコールモノメチルエーテル 10部
P-5:シクロヘキサノールアセテート 10部
P-6:ジプロプレングリコールメチルエーテルアセテート 10部
以上、(P-1)~(P-6)をそれぞれ上記質量部にて混合し、有機溶剤(P)とした。
[Organic solvent (P)]
P-1: Propylene glycol monomethyl ether acetate 30 parts P-2: Cyclohexanone 30 parts P-3: Ethyl 3-ethoxypropionate 10 parts P-4: Propylene glycol monomethyl ether 10 parts P-5: Cyclohexanol acetate 10 parts P -6: Dipropylene glycol methyl ether acetate 10 parts Above, (P-1) to (P-6) were mixed in the above mass parts, respectively, to obtain an organic solvent (P).
<感光性組成物の評価>
得られた感光性組成物1~38(実施例1~35、比較例1~3)について、水しみ、パターン形成性(密着性、直線性)、及び残膜率の評価を下記の方法で行った。評価結果を表3に示す。
<Evaluation of photosensitive composition>
The obtained photosensitive compositions 1 to 38 (Examples 1 to 35, Comparative Examples 1 to 3) were evaluated for water stains, pattern forming properties (adhesion, linearity), and residual film rate using the following methods. went. The evaluation results are shown in Table 3.
[水しみ評価]
得られた感光性組成物について、縦100mm×横100mm、0.7mmのガラス基板(コーニング社製イーグル2000)上に、乾燥後の膜厚が3.0μmとなるように塗工し、70℃1分間ホットプレートで乾燥した。次いで、100μm幅のストライプパターンを有するマスクを通して高圧水銀灯を用いて照度30mW/cm2、40mJ/cm
2の条件下にて紫外線露光を行った。その後、非イオン系界面活性剤0.12%と水酸化カリウム0.04%とを含む水系現像液に、23℃で40秒間浸漬して現像し、純水で洗浄した。得られたパターンをNikon社製ECLIPSE LV100POL Model光学顕微鏡を用いて、パターンの表面を観察し、変色している部分の度合いを評価した。評価基準は、以下の通りであり、3以上を実用可能とする。
5:水しみがなかった。
4:水しみが全体の10%未満であった。
3:水しみが全体の10%以上~20%未満であった。
2:水しみが全体の20%以上~30%未満であった。
1:水しみが全体の30%以上であった。
[Water stain evaluation]
The obtained photosensitive composition was coated on a 0.7 mm glass substrate (Eagle 2000 manufactured by Corning) with a length of 100 mm x width of 100 mm so that the film thickness after drying was 3.0 μm, and the film was heated at 70°C. It was dried on a hot plate for 1 minute. Next, a high-pressure mercury lamp was used to pass through a mask having a stripe pattern of 100 μm width at an illuminance of 30 mW/cm 2 and 40 mJ/cm.
Ultraviolet light exposure was performed under the following conditions. Thereafter, the film was developed by immersing it in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 23° C. for 40 seconds, and was washed with pure water. The surface of the obtained pattern was observed using an optical microscope ECLIPSE LV100POL Model manufactured by Nikon, and the degree of discoloration of the portion was evaluated. The evaluation criteria are as follows, and scores of 3 or higher are considered practical.
5: There was no water stain.
4: Water stains accounted for less than 10% of the total.
3: Water stains accounted for 10% or more and less than 20% of the total.
2: Water stains accounted for 20% or more and less than 30% of the total.
1: Water stains accounted for 30% or more of the whole.
<パターン形成性評価用基板の作製>
得られた感光性組成物を、スピンコート法により縦100mm×横100mm、0.7mm厚のガラス基板(コーニング社製イーグル2000)に、乾燥後の膜厚が3.0μmとなるように塗工し、70℃1分間ホットプレートで乾燥した。次いで、この基板を室温に冷却後、高圧水銀灯ランプを用い、5μm幅刻みのストライプパターンのフォトマスクを介して照度30mW/cm2、40mJ/cm2で露光した。その後、この基板を23℃の非イオン系界面活性剤0.12質量%と水酸化カリウム0.04質量%とを含む水系現像液を用いてスプレー現像した後、イオン交換水で洗浄、風乾し、クリーンオーブン中230℃で30分間加熱しパターン形成性評価用基板を得た。スプレー現像は、それぞれの感光性組成物での被膜について、現像残りなくパターン形成可能な最短時間で行った。
<Preparation of substrate for pattern formability evaluation>
The obtained photosensitive composition was applied to a 100 mm long x 100 mm wide, 0.7 mm thick glass substrate (Eagle 2000 manufactured by Corning) by a spin coating method so that the film thickness after drying was 3.0 μm. and dried on a hot plate at 70°C for 1 minute. Next, after cooling this substrate to room temperature, it was exposed to light using a high-pressure mercury lamp at an illuminance of 30 mW/cm 2 and 40 mJ/cm 2 through a photomask having a stripe pattern with a width of 5 μm. Thereafter, this substrate was spray developed using an aqueous developer containing 0.12% by mass of a nonionic surfactant and 0.04% by mass of potassium hydroxide at 23°C, then washed with ion-exchanged water, and air-dried. The substrate was heated at 230° C. for 30 minutes in a clean oven to obtain a substrate for evaluating pattern formability. Spray development was carried out for the coating film of each photosensitive composition for the shortest time possible to form a pattern without any development residue.
[パターン形成性評価(1):密着性]
上記方法で作成されたパターン形成性評価用基板のうち幅5、10、15、20、および25μmのパターンについて、光学顕微鏡で観察し、残存したパターンの最小線幅を確認した。評価基準は、以下の通りであり、3以上を実用可能とする。
5:10μm以下の細線が残存している。
4:15μm以下の細線が残存している。
3:20μm以下の細線が残存している。
2:25μm以下の細線が残存している。
1:細線が残存していない。
[Pattern formation evaluation (1): Adhesion]
Among the substrates for evaluating pattern formability created by the above method, patterns with widths of 5, 10, 15, 20, and 25 μm were observed with an optical microscope to confirm the minimum line width of the remaining patterns. The evaluation criteria are as follows, and scores of 3 or higher are considered practical.
5: Fine lines of 10 μm or less remain.
4: Fine lines of 15 μm or less remain.
3: Fine lines of 20 μm or less remain.
2: Fine lines of 25 μm or less remain.
1: No fine lines remain.
[パターン形成評価(2):直線性]
パターン形成性評価(1)で作成した基板を、Nikon社製ECLIPSE LV100POL Model光学顕微鏡を用いて、10箇所のストライプパターンの線幅の最大と最小部分を測定しその平均を求めることで評価を行った。評価基準は、以下の通りであり、3以上を実用可能とする。
5:線幅の最大値と最小値の差が0.5μm未満
4:線幅の最大値と最小値の差が0.5μm以上、1.0μm未満
3:線幅の最大値と最小値の差が1.0μm以上、1.5μm未満
2:線幅の最大値と最小値の差が1.5μm以上、2.0μm未満
1:線幅の最大値と最小値の差が2.0μm以上
[Pattern formation evaluation (2): linearity]
The substrate prepared in pattern formability evaluation (1) was evaluated by measuring the maximum and minimum line widths of the stripe pattern at 10 locations using a Nikon ECLIPSE LV100POL Model optical microscope and calculating the average. Ta. The evaluation criteria are as follows, and scores of 3 or higher are considered practical.
5: The difference between the maximum and minimum line widths is less than 0.5 μm 4: The difference between the maximum and minimum line widths is 0.5 μm or more and less than 1.0 μm 3: The difference between the maximum and minimum line widths The difference is 1.0 μm or more and less than 1.5 μm 2: The difference between the maximum and minimum line widths is 1.5 μm or more and less than 2.0 μm 1: The difference between the maximum and minimum line widths is 2.0 μm or more
[残膜率評価]
上記パターン形成性評価用基板の作成時において、スプレー現像を行い、イオン交換水で洗浄し風乾後の塗膜の膜厚を測定した。この膜厚を現像後膜厚とする。その後、クリーンオーブン中230℃で30分間加熱し、現像後膜厚を測定した同じ場所の膜厚を測定した。この膜厚をベーク後膜厚とする。2つの膜厚から下記数式により残膜率を算出した。評価基準は、以下の通りであり、3以上を実用可能とする。なお、膜厚は、Dektak 3030(日本真空技術社製)を用いて行った。
数式:残膜率(%)=ベーク後膜厚÷現像後膜厚×100
5:残膜率85%以上
4:残膜率80%以上85%未満
3:残膜率75%以上80%未満
2:残膜率70%以上75%未満
1:残膜率70%未満
[Residual film rate evaluation]
When creating the above-mentioned substrate for evaluating pattern formability, spray development was performed, and the film thickness of the coating film after washing with ion-exchanged water and air drying was measured. This film thickness is defined as the film thickness after development. Thereafter, the film was heated in a clean oven at 230° C. for 30 minutes, and the film thickness was measured at the same location where the film thickness was measured after development. This film thickness is defined as the film thickness after baking. The remaining film rate was calculated from the two film thicknesses using the following formula. The evaluation criteria are as follows, and scores of 3 or higher are considered practical. Note that the film thickness was measured using Dektak 3030 (manufactured by Nippon Vacuum Technology Co., Ltd.).
Formula: Remaining film rate (%) = Film thickness after baking ÷ Film thickness after development x 100
5: Remaining film rate 85% or more 4: Remaining film rate 80% or more and less than 85% 3: Remaining film rate 75% or more and less than 80% 2: Remaining film rate 70% or more and less than 75% 1: Remaining film rate less than 70%
[実施例2~35、比較例1~3]
(感光性組成物2~38)
実施例1の感光性組成物1を、表2-1~表2-4に記載した原料、量に変えた以外は、実施例1と同様にして感光性組成物2~38を作製した。なお
本明細書で実施例1は、参考例である。
[Examples 2 to 35, Comparative Examples 1 to 3]
(Photosensitive compositions 2 to 38)
Photosensitive compositions 2 to 38 were prepared in the same manner as in Example 1, except that the raw materials and amounts of Photosensitive composition 1 in Example 1 were changed to those listed in Tables 2-1 to 2-4. In addition
Example 1 herein is a reference example.
Claims (7)
前記光重合開始剤(C)が、下記一般式(1)で表されるオキシム系光重合開始剤(C1)、及びオキシム系光重合開始剤(C1)以外のオキシム系光重合開始剤(C2)を含む、感光性組成物。
一般式(1)
(一般式(1)中、R1は、水素原子、炭素原子数1~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R2は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R3は、炭素原子数3~20のアルキル基、炭素原子数6~30のアリール基、炭素原子数7~30のアリールアルキル基、又は炭素原子数2~20の複素環基を表す。
R4は、1価の置換基を表す。nは、0~3の整数を表す。) A photosensitive composition comprising an alkali-soluble resin (A), a polymerizable compound (B), and a photoinitiator (C),
The photopolymerization initiator (C) is an oxime photopolymerization initiator (C1) represented by the following general formula (1), and an oxime photopolymerization initiator (C2) other than the oxime photopolymerization initiator (C1). ).
General formula (1)
(In general formula (1), R 1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or Represents 2 to 20 heterocyclic groups.
R 2 represents an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
R 3 represents an alkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.
R 4 represents a monovalent substituent. n represents an integer from 0 to 3. )
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JP2011020998A (en) * | 2009-06-17 | 2011-02-03 | Toyo Ink Mfg Co Ltd | New oxime ester compound, radical polymerization initiator comprising the same, and polymerizable composition containing the same, and negative-type resist using the composition, and method for forming image pattern using the resist |
JP2017501250A (en) * | 2013-11-28 | 2017-01-12 | タコマ テクノロジー カンパニー リミテッドTakoma Technology Co.,Ltd. | Photoinitiator and photosensitive composition thereof |
JP2017512886A (en) * | 2014-03-18 | 2017-05-25 | 常州強力先端電子材料有限公司Cahngzhou Tronly Advanced Electronic Materials Co.,Ltd. | Bisoxime ester-based photopolymerization initiator and its production method and application |
JP2020086317A (en) * | 2018-11-29 | 2020-06-04 | 東京応化工業株式会社 | Photosensitive resin composition, production method of patterned cured film, and patterned cured film |
JP2022515524A (en) * | 2018-12-28 | 2022-02-18 | サムヤン コーポレイション | A carbazole multi-β-oxime ester derivative compound, a photopolymerization initiator containing the same, and a photoresist composition. |
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JP2011020998A (en) * | 2009-06-17 | 2011-02-03 | Toyo Ink Mfg Co Ltd | New oxime ester compound, radical polymerization initiator comprising the same, and polymerizable composition containing the same, and negative-type resist using the composition, and method for forming image pattern using the resist |
JP2017501250A (en) * | 2013-11-28 | 2017-01-12 | タコマ テクノロジー カンパニー リミテッドTakoma Technology Co.,Ltd. | Photoinitiator and photosensitive composition thereof |
JP2017512886A (en) * | 2014-03-18 | 2017-05-25 | 常州強力先端電子材料有限公司Cahngzhou Tronly Advanced Electronic Materials Co.,Ltd. | Bisoxime ester-based photopolymerization initiator and its production method and application |
JP2020086317A (en) * | 2018-11-29 | 2020-06-04 | 東京応化工業株式会社 | Photosensitive resin composition, production method of patterned cured film, and patterned cured film |
JP2022515524A (en) * | 2018-12-28 | 2022-02-18 | サムヤン コーポレイション | A carbazole multi-β-oxime ester derivative compound, a photopolymerization initiator containing the same, and a photoresist composition. |
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