CN115244462A - Positive photosensitive resin composition - Google Patents
Positive photosensitive resin composition Download PDFInfo
- Publication number
- CN115244462A CN115244462A CN202180018155.6A CN202180018155A CN115244462A CN 115244462 A CN115244462 A CN 115244462A CN 202180018155 A CN202180018155 A CN 202180018155A CN 115244462 A CN115244462 A CN 115244462A
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- CN
- China
- Prior art keywords
- positive photosensitive
- resin composition
- photosensitive resin
- compound
- group
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229920005989 resin Polymers 0.000 claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 32
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 26
- 239000004094 surface-active agent Substances 0.000 claims abstract description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 4
- 230000002378 acidificating effect Effects 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 10
- -1 quinonediazide compound Chemical class 0.000 claims description 8
- 239000005011 phenolic resin Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 238000005192 partition Methods 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 2
- 238000011156 evaluation Methods 0.000 description 17
- 229920001296 polysiloxane Polymers 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 238000011161 development Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical group OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- 238000003491 array Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical group OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Polymers C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical group O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- BNWKXMCELVEAPW-UHFFFAOYSA-N chembl3305990 Chemical compound O=C1C(=[N+]=[N-])C=CC2=C1C=CC=C2S(=O)(=O)O BNWKXMCELVEAPW-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- G03F7/022—Quinonediazides
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/22—Exposing sequentially with the same light pattern different positions of the same surface
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
Abstract
The present invention relates to a positive photosensitive resin composition containing an alkali-soluble resin (A), a photosensitizer (B), a crosslinking agent (C) and a surfactant (D), wherein the crosslinking agent (C) contains a compound having 1 or more acid groups selected from the group consisting of carboxyl groups, phenolic hydroxyl groups, sulfo groups and phosphoric acid groups, the proportion of the compound having the acid groups is in the range of 5 to 35% by mass relative to the total of (A) + (B) + (C) + (D), and the surfactant (D) does not have F atoms.
Description
Technical Field
The present invention relates to a positive photosensitive resin composition.
Background
Positive photosensitive resin compositions are used for forming color filters, organic EL devices, partition walls for forming pixels used in the manufacture of TFT arrays, interlayer insulating films, planarization films, and microlenses (for example, patent documents 1 and 2).
Documents of the prior art
Patent document
Patent document 1 Japanese patent No. 6384678
Patent document 2, japanese patent laid-open No. 2010-134422
Disclosure of Invention
In recent years, the performance of products has been increasingly required, and the performance of conventional positive photosensitive resin compositions has been insufficient.
Under such circumstances, a positive photosensitive resin composition having high adhesion to a substrate, less development residue, and excellent solvent resistance has been desired.
The present invention includes the following aspects.
1. A positive photosensitive resin composition comprising an alkali-soluble resin (A), a photosensitizer (B), a crosslinking agent (C) and a surfactant (D), wherein the crosslinking agent (C) contains a compound having at least 1 kind of acidic group selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfo group and a phosphate group,
the proportion of the compound having the acidic group is in the range of 5 to 35% by mass relative to the total of (A) + (B) + (C) + (D),
the surfactant (D) does not have a F atom.
2. The positive photosensitive resin composition according to claim 1, wherein the photosensitizer (B) contains a quinonediazide compound.
3. The positive photosensitive resin composition according to 1 or 2, wherein the alkali-soluble resin (a) has a mass average molecular weight in a range of 500 to 10000.
4. The positive photosensitive resin composition according to any one of claims 1 to 3, wherein the alkali-soluble resin (A) is a phenol resin.
5. The positive photosensitive resin composition according to claim 4, wherein the phenol resin is an o-cresol resin.
6. The positive photosensitive resin composition according to any one of claims 1 to 5, wherein the acidic group is a carboxyl group.
7. The positive photosensitive resin composition according to claim 6, wherein the crosslinking agent (C) contains a compound having 1 to 3 carboxyl groups in 1 molecule.
8. The positive photosensitive resin composition according to any one of claims 1 to 7, wherein a proportion of the compound having the acidic group in the crosslinking agent (C) is 30% or more by mass.
9. The positive photosensitive resin composition according to any one of claims 1 to 8, further comprising a solvent (E), wherein the proportion of the compound having a boiling point of 170 ℃ or higher in the solvent is in the range of 10 to 70% by mass.
10. A cured product obtained by curing the positive photosensitive resin composition described in any one of 1 to 9.
11. An optical element comprising the cured product of 10 as a partition wall.
The present invention can provide a positive photosensitive resin composition having high adhesion to a substrate, less development residue, and excellent solvent resistance.
Detailed Description
The positive photosensitive resin composition of the present invention will be described below.
[ Positive photosensitive resin composition ]
The positive photosensitive resin composition of the present invention is composed of a combination of essential components and optional components. The essential component is required to be contained in the positive photosensitive resin composition and provides a main function of performance. Any component may be used as required.
Unless otherwise specified, the term "mass" means "mass%. However, in the present specification, the proportion (percentage, parts, etc.) on the mass basis is the same as the proportion (percentage, parts, etc.) on the weight basis. Numerical ranges include ranges that are rounded. In addition, the numerical range "X to Y" means "X to Y inclusive".
[ essential Components ]
The essential components are an alkali-soluble resin (A), a sensitizer (B), a crosslinking agent (C), and a surfactant (D).
< alkali-soluble resin (A) >)
The alkali-soluble resin (a) is a resin that is dissolved in an alkali used in a developing step, and is a resin that becomes a main component of a partition wall used in a pixel portion or the like.
As the alkali-soluble resin (a) used in the present invention, a known resin used in a positive photosensitive resin composition can be used.
As a specific example, alkali-soluble resins described in japanese patent No. 6177495, japanese patent No. 5447384, japanese patent No. 4770985, japanese patent No. 4600477, japanese patent No. 5444749, and international publication No. 2019/156000 are exemplified as the alkali-soluble resin (a), but the alkali-soluble resin (a) is not limited to these.
As specific examples of the preferable alkali-soluble resin (a), the following resins are shown, but the alkali-soluble resin (a) is not limited to these examples.
As the alkali-soluble resin (a), a phenolic resin is preferable. When a phenol resin is used, the curability of the obtained positive photosensitive resin composition is improved, and the occurrence of outgas is reduced. As the phenol resin, o-cresol resin is preferable because the molecular weight of the resin can be controlled to be small.
The mass average molecular weight of the alkali-soluble resin (A) is preferably in the range of 500 to 10000, more preferably in the range of 1000 to 5000, and particularly preferably in the range of 1000 to 3000, in order to achieve excellent residue removability.
The mass average molecular weight (Mw) in the present specification represents a mass average molecular weight in terms of standard polystyrene as a standard, which is measured by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a mobile phase.
The amount of the alkali-soluble resin (a) to be used is preferably in the range of 40 to 80%, more preferably in the range of 50 to 75%, and particularly preferably in the range of 55 to 72% in terms of mass ratio to the total of (a) + (B) + (C) + (D). When the amount is within this range, the effects of the present invention can be more effectively exhibited.
< photosensitizer (B) >
The sensitizer (B) is a compound which reacts with light upon exposure to change the solubility of the positive photosensitive resin composition in an alkaline solution.
Examples of the sensitizer (B) used in the present invention include known sensitizers used for positive photosensitive resin compositions.
As the photosensitizer (B), a compound having a quinonediazide group (hereinafter also referred to as a quinonediazide compound) is preferable for excellent photosensitivity.
The amount of the photosensitizer (B) to be used is preferably in the range of 10 to 35% by mass, more preferably 15 to 30% by mass, and particularly preferably 17 to 22% by mass, based on the total amount of (A) + (B) + (C) + (D). When the amount is within this range, the effects of the present invention can be more effectively exhibited.
< crosslinking agent (C) >)
The crosslinking agent (C) is a compound contributing to curability of the positive photosensitive resin composition, and has 2 or more photocurable functional groups. The photocurable functional group is preferably the same kind of functional group as the photocurable functional group of the alkali-soluble resin (a). Specifically, an ethylenic double bond is preferable as the photocurable functional group.
The number of photocurable functional groups of the crosslinking agent (C) is 2 or more, preferably 3 or more, more preferably 4 or more, and particularly preferably 5 or more per 1 molecule. The larger the number of photocurable functional groups, the higher the curability of the coating film surface, and the reliability of the cured product such as solvent resistance and outgassing is improved.
The crosslinking agent (C) used in the present invention contains a compound having 1 or more kinds of acid groups selected from a carboxyl group, a phenolic hydroxyl group, a sulfo group and a phosphoric acid group (hereinafter, also referred to as a compound having an acid group), and preferably contains a compound having a carboxyl group. The number of the acid groups of the compound having an acid group is 1 or more, preferably 1 to 3, and particularly preferably 1 in 1 molecule.
The compound having the acidic group has the above structure, and the effects of the present invention can be more effectively exhibited. In addition, the crosslinking agent is uniformly dispersed in the cured film, and the permeability of the developer can be improved.
The mass average molecular weight of the compound having an acidic group is preferably 100 to 1500, more preferably 300 to 1000, and particularly preferably 400 to 800, from the viewpoint of permeation of the developer and diffusion in a liquid.
Specific examples of the compound having the above-mentioned acidic group are given below, but the compound having an acidic group is not limited to these.
The compound having an acidic group is preferably a compound in which an acidic group is introduced into an ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound with a hydroxyl compound having a (meth) acryloyl group, and 2 or more unsaturated bonds (ethylenic double bonds) remain, for example, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, an ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid, or the like.
In addition, from the viewpoint of the introduction ratio of the ethylenic double bond, the compound having an acidic group is preferably a compound having an isocyanurate skeleton, a trimethylolpropane skeleton, a phthalic acid skeleton, a pentaerythritol skeleton, a dipentaerythritol skeleton, or a tripentaerythritol skeleton, and particularly preferably a compound having a dipentaerythritol skeleton.
More specifically, the compound having an acidic group is particularly preferably a compound in which 5 hydroxyl groups of dipentaerythritol are substituted with a (meth) acryloyloxy group, and the remaining 1 hydroxyl group is ester-bonded to succinic acid, for example, to introduce an acidic group.
These compounds have 2 or more, preferably 3 or more, more preferably 4 or more, particularly preferably 5 or more photocurable functional groups, preferably ethylenic double bonds, more preferably acrylate groups in 1 molecule and further have an acidic group at the same time, and thus can achieve both solvent resistance and a reduction in development residue at a high level.
The acid value of the crosslinking agent (C) is preferably not less than 10mgKOH/g, more preferably not less than 20mgKOH/g, and still more preferably not less than 50 mgKOH/g. The acid value is preferably 200mgKOH/g or less, more preferably 150mgKOH/g or less, and still more preferably 100mgKOH/g or less. The acid value is preferably from 10 to 200mgKOH/g, more preferably from 20 to 150mgKOH/g, and particularly preferably from 50 to 100mgKOH/g. If the acid value of the crosslinking agent (C) is not less than the lower limit, the positive photosensitive resin composition can have better solubility in a developer.
The crosslinking agent (C) may be used alone or in combination with other crosslinking agents, wherein the crosslinking agent (C) is 1 compound having the above-mentioned acidic group.
The proportion of the compound having an acidic group in the crosslinking agent (C) is preferably 30% or more, more preferably 50% or more, and particularly preferably 60% or more by mass ratio.
The amount of the compound having an acidic group is 5 to 35% by mass based on the total amount of (A) + (B) + (C) + (D). The amount of the above-mentioned compound is preferably 6% or more, more preferably 8% or more. The amount used is preferably 25% or less, more preferably 20% or less. The amount used is preferably 6 to 25%, particularly preferably 8 to 20%. When the amount is within this range, the effects of the present invention can be more effectively exhibited. More specifically, when the amount of the compound having an acidic group is equal to or more than the lower limit value, excellent solvent resistance and an effect of reducing development residue can be easily achieved at the same time. When the amount of the additive is less than the upper limit, the adhesion to the substrate is easily improved.
The proportion of the crosslinking agent (C) is preferably 8% or more, more preferably 10% or more, further preferably 12% or more, and particularly preferably 14% or more, by mass relative to the alkali-soluble resin (a). The above proportion is preferably 40% or less, more preferably 35% or less, further preferably 30% or less, and particularly preferably 26% or less. The above proportion is preferably 8 to 40%, more preferably 10 to 35%, particularly preferably 12 to 30%, most preferably 14 to 26%. When the ratio of the crosslinking agent (C) to the alkali-soluble resin (a) is in this range, the balance between the developer solubility and the pattern shape is excellent.
< surfactant (D) >, a process for producing the same, and a process for producing the same
The surfactant (D) improves the coatability of the positive photosensitive resin composition and also improves the residue removability during development.
The surfactant (D) of the present invention has no F atom. The surfactant (D) does not have F atoms, so that the ink repellency is reduced, and is suitable for applications requiring affinity for ink. On the other hand, when the ink repellent is used, ink repellency is generated at a position where the ink is applied, and the applicability of the ink is remarkably reduced. Therefore, the surfactant (D) is not preferably a compound used as an ink repellent.
Specific examples of the surfactant (D) are given below, but not limited thereto.
Examples of the surfactant (D) include silicone surfactants, nonionic, anionic, cationic and amphoteric surfactants, and polyether-modified silicone surfactants are preferred.
More specifically, examples of the Silicone surfactant include commercially available products such as "Toray Silicone DC3PA", "Toray Silicone SH7PA", "Toray Silicone DC11PA", "Toray Silicone SH21PA", "Toray Silicone SH28PA", "Toray Silicone SH29PA", "Toray Silicone SH30PA", "Toray Silicone SH8400", momentive Performance Materials Japan contract society, "TSF-4440", "TSF-4300", "TSF-4445", "TSF-444 (4) (5) (6) (7)", "TSF-4460", "TSF-4452", kyueko chemical industry Co., ltd. "KP341", and "BYK323" and "BYK330" manufactured by Big Chemie.
The amount of the surfactant (D) used is preferably in the range of 0.1 to 1.0% by mass relative to the total amount of (a) + (B) + (C) + (D). When the amount is within this range, the effects of the present invention can be more effectively exhibited.
[ optional Components ]
< solvent (E) >, and
the positive photosensitive resin composition of the present invention may contain a solvent (E).
By containing the solvent (E), the positive photosensitive resin composition is more excellent in coatability, adhesion to a substrate, and stability.
As the solvent (E), a known solvent used for a positive photosensitive resin composition can be used. Specific examples of the solvent (E) include alcohols, ethers, aromatics, and hydrocarbons, but the solvent (E) is not limited thereto.
In order to improve the uniformity of the coating film of the positive photosensitive resin composition and to achieve excellent layer separation, the proportion of the compound having a boiling point of 170 ℃ or higher in the solvent (E) is particularly preferably in the range of 10 to 70 mass%.
The amount of the solvent (E) is preferably in the range of 60 to 90% by mass, and particularly preferably in the range of 75 to 85% by mass in the positive photosensitive resin composition.
< other ingredients >
The positive photosensitive resin composition of the present invention may contain known components added as a positive photosensitive resin composition, such as a thermosetting agent, a thermosetting accelerator, a colorant, a silane coupling agent, fine particles, a thickener, a plasticizer, an antifoaming agent, a leveling agent, an anti-shrinking agent, and an ultraviolet absorber, as necessary, within a range not to impair the effects of the present invention. More specifically, components described in paragraphs 0080 to 0095 of Japanese patent No. 6098635, and the like can be added.
[ method for producing Positive photosensitive resin composition ]
The positive photosensitive resin composition is prepared by mixing an alkali-soluble resin (a), a photosensitizer (B), a crosslinking agent (C), and a surfactant (D), and a solvent and other components as necessary until uniform.
The positive photosensitive resin composition of the present invention is suitably used for the formation of partition walls for forming pixels, interlayer dielectric films, planarization films, and microlenses in optical elements such as organic EL elements, color filters, and TFT arrays, but the use is not limited thereto. For example, a cured product obtained by curing the positive photosensitive resin composition of the present invention can be suitably used for the above-mentioned applications.
As an example, a method for manufacturing an organic EL element is shown.
A transparent electrode such as tin-doped indium oxide (ITO) is formed on a transparent substrate such as glass by a sputtering method or the like, and the transparent electrode is etched into a desired pattern as necessary. Next, partition walls (cured products) are formed using the positive photosensitive resin composition of the present invention, and further, a bank-protecting agent having a liquid-repellent surface is formed, and then, a solution of a hole-transporting material and a solution of a light-emitting material are applied to the dots in this order by an ink-jet method, followed by drying, thereby forming a hole-transporting layer and a light-emitting layer. Thereafter, an electrode of aluminum or the like is formed by a vapor deposition method or the like, thereby obtaining a pixel of an organic EL element.
Examples
The present invention is specifically described by examples and comparative examples, but the embodiments may be appropriately modified as long as the effects of the present invention are obtained. Examples 1 to 10 are examples, and examples 11 to 13 are comparative examples.
< measurement Condition and evaluation Condition >
[ sample for evaluation ]
Using the positive photosensitive resin compositions described in table 1, cured films were formed on ITO substrates to prepare samples for evaluation. As evaluation samples, two kinds of evaluation samples 1 and 2 were prepared.
The adhesion and solvent resistance were evaluated using sample 1 for evaluation.
The amount of development residue was evaluated using sample 2 for evaluation.
[ sample 1 for evaluation ]
An ITO substrate (an ITO product having a resistance value of 10. Omega./sq or less, a size of 7.5 cm. Times.7.5 cm. Times.0.7 mm, manufactured by Kakkiso Co., ltd.) was ultrasonically cleaned in ethanol (30 minutes).
Next, ultraviolet/ozone cleaning was performed for 5 minutes (apparatus: PL7-200Sen Engineering Co., ltd.).
The cleaned substrate surface was spin-coated (rotation speed 610rpm,10 seconds) with a positive photosensitive resin composition using a spinner (IH-DX 2, mikasa corporation). Then, the film was dried on a hot plate at 100 ℃ for 2 minutes to form a film having a thickness of 1.3 μm. The surface of the obtained film was exposed to light under the following conditions.
< Condition >
[ photomask ]: the light shielding portion has a repeating 18 line pattern in a range of 20mm × 20 mm.
Shape of light shielding portion: 1, 2,3,4, 5,6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 30, 40, 50 μm × 1000 μm
Pattern spacing: 50 μm
[ Lamp)]: USH-255BY, manufactured by Ushio Motor Co., ltd., exposure Power (exposure output) 25mW/cm in terms of 365nm 2
[ conditions of irradiation]: cut off light below 330nm, at a gap of 50 μm, at 25mW/cm 2 The irradiation was carried out for 8 seconds.
The exposed ITO substrate was immersed in a tetramethylammonium hydroxide aqueous solution (0.4 mass%) for 40 seconds and developed. Thereafter, washing with water and drying were performed. The dried substrate was heated on a hot plate (220 ℃ C., 60 minutes) to prepare an ITO substrate having a cured film with a specific pattern formed thereon (sample 1 for evaluation).
[ sample for evaluation 2]
Sample 2 for evaluation was produced in the same manner as sample 1 for evaluation, except that the photomask used was changed.
[ photomask ]: the opening part is formed in a pattern of 20mm × 20 mm.
Shape of opening part: 100 μm × 200 μm
Pattern spacing: 20 μm
[ Adhesivity ]
The pattern of the cured film of sample 1 for evaluation was observed by a microscope, and the adhesion was judged according to the presence or absence of line defects of the cured film remaining without peeling in the cleaning step, based on the following criteria.
Good: lines with a width of less than 10 μm were defect-free.
Not: lines less than 10 μm wide have defects.
The product is qualified.
[ development residue ]
The amount of residue at the bank-removed portion of the cured film of sample 2 for evaluation was measured. Note that the bank removing portion is a portion from which the film is removed in the developing operation.
The amount of residue on the ITO surface of the bank removed portion was measured by the μ -XPS method and evaluated according to the following criteria.
< measurement conditions >
A measuring device: quanterasxmx ray manufactured by ULVAC-PHI corporation
Conditions are as follows: 50 μm phi, 12.5W,15kV
Size of grating: point
Sample angle: 45 degree
And (3) acquisition period: 18
Energy-on step length: the measurement was carried out at 0.4eV, and the measurement data were expressed by C/In.
And (3) excellent: the amount of residue is 4 or less.
Good: the amount of residue is greater than 4 and not greater than 5.
Can be as follows: the amount of residue is greater than 5 and not more than 8.
Not: the residue amount is more than 8.
Excellent and good, can be qualified.
[ solvent resistance ]
To the cured film of sample 1 for evaluation, 2.5. Mu.l of PGMEA (propylene glycol monomethyl ether acetate) was dropped and left for 60 seconds.
Thereafter, the PGMEA was wiped with a wiping cloth (manufactured by Bemcot M-3II Asahi chemical Co., ltd.), and the presence or absence of a dissolution mark on the upper surface of the film was confirmed by visual observation, and evaluated according to the following criteria.
Good: no dissolution mark.
Can be as follows: the surface had a slight trace of rounding.
Not: there were dissolution marks.
Good and acceptable.
[ examples and comparative examples ]
The raw materials were stirred (about 30 minutes) in the proportions described in table 1 until uniform to prepare a positive photosensitive resin composition. Using the positive photosensitive resin composition, samples 1 and 2 for evaluation were prepared and evaluated. The evaluation results are shown in table 1.
The numbers in the table are represented by the first digit of the decimal point of the significant figure. The blank column in the table indicates that the column of components is not included.
[ Table 1]
< description of abbreviations >
[ alkali-soluble resin (A) ]
A1: o-cresol novolac resin (Mw: 1740)
A2: o-cresol novolac resin (Mw: 2470)
[ photosensitizer (B) ]
B1: (mono-to tetra-) esters of 2,3, 4' -tetrahydroxybenzophenone with 6-diazo-5, 6-dihydro-5-oxo-naphthalene-1-sulfonic acid
[ crosslinking agent (C) ]
C1: polyacid-modified acrylic oligomer (mixture of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and succinate ester of dipentaerythritol pentaacrylate (acid value 92mgKOH/g, molecular weight 612))
C2:2, 2-Triacryloyloxymethylethyl phthalic acid (acid value: 87mgKOH/g, molecular weight: 446)
C3: mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate
[ surfactant (D) ]
D1: xylene/styrene glycol mixed solution of polyether-modified polydimethylsiloxane (solid content 12.5%)
[ solvent (E) ]
EDM: diethylene glycol ethyl methyl ether (boiling point 176 ℃ C.)
PGME: propylene glycol monomethyl ether (boiling point 120 ℃ C.)
PGMEA: propylene glycol monomethyl ether acetate (boiling point 146 ℃ C.)
While the present invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof. This application is based on Japanese patent application No. 3/4/2020 (Japanese patent application No. 2020-037170), the contents of which are incorporated herein by reference.
Claims (11)
1. A positive photosensitive resin composition comprising an alkali-soluble resin (A), a photosensitizer (B), a crosslinking agent (C) and a surfactant (D), wherein the crosslinking agent (C) comprises a compound having at least 1 selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfo group and a phosphoric group as an acidic group,
the proportion of the compound having the acidic group is in the range of 5 to 35% by mass relative to the total of (A) + (B) + (C) + (D),
the surfactant (D) has no F atom.
2. The positive photosensitive resin composition according to claim 1, wherein the sensitizer (B) contains a quinonediazide compound.
3. The positive photosensitive resin composition according to claim 1 or 2, wherein the alkali-soluble resin (a) has a mass average molecular weight in the range of 500 to 10000.
4. The positive photosensitive resin composition according to any one of claims 1 to 3, wherein the alkali-soluble resin (A) is a phenolic resin.
5. The positive photosensitive resin composition according to claim 4, wherein the phenol resin is an o-cresol resin.
6. The positive photosensitive resin composition according to any one of claims 1 to 5, wherein the acidic group is a carboxyl group.
7. The positive photosensitive resin composition according to claim 6, wherein the crosslinking agent (C) contains a compound having 1 to 3 carboxyl groups in 1 molecule.
8. The positive photosensitive resin composition according to any one of claims 1 to 7, wherein a proportion of the compound having the acidic group in the crosslinking agent (C) is 30% or more by mass.
9. The positive photosensitive resin composition according to any one of claims 1 to 8, further comprising a solvent (E), wherein the proportion of a compound having a boiling point of 170 ℃ or higher in the solvent is in the range of 10 to 70% by mass.
10. A cured product obtained by curing the positive photosensitive resin composition according to any one of claims 1 to 9.
11. An optical element comprising the cured product of claim 10 as partition walls.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020037170 | 2020-03-04 | ||
| JP2020-037170 | 2020-03-04 | ||
| PCT/JP2021/007782 WO2021177250A1 (en) | 2020-03-04 | 2021-03-01 | Positive-type photosensitive resin composition |
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| Publication Number | Publication Date |
|---|---|
| CN115244462A true CN115244462A (en) | 2022-10-25 |
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| JP (1) | JPWO2021177250A1 (en) |
| KR (1) | KR20220149671A (en) |
| CN (1) | CN115244462A (en) |
| TW (1) | TW202141186A (en) |
| WO (1) | WO2021177250A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06118648A (en) * | 1991-12-10 | 1994-04-28 | Konica Corp | Positive type photosensitive composition and image forming method |
| JP4544370B2 (en) | 2008-10-28 | 2010-09-15 | Ｊｓｒ株式会社 | Radiation-sensitive resin composition, interlayer insulating film and microlens, and production method thereof |
| JP6177495B2 (en) * | 2011-06-01 | 2017-08-09 | 日立化成株式会社 | Positive photosensitive resin composition and photosensitive film |
| CN105829967B (en) | 2013-10-21 | 2020-02-07 | 日产化学工业株式会社 | Positive photosensitive resin composition |
| JP2016042126A (en) * | 2014-08-15 | 2016-03-31 | Jsr株式会社 | Radiation-sensitive resin composition, interlayer insulation film of display element, method of forming the same, and display element |
| JP2016166951A (en) * | 2015-03-09 | 2016-09-15 | Jnc株式会社 | Photosensitive composition |
-
2021
- 2021-03-01 CN CN202180018155.6A patent/CN115244462A/en not_active Withdrawn
- 2021-03-01 JP JP2022504364A patent/JPWO2021177250A1/ja not_active Withdrawn
- 2021-03-01 WO PCT/JP2021/007782 patent/WO2021177250A1/en active Application Filing
- 2021-03-01 KR KR1020227030026A patent/KR20220149671A/en unknown
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| TW202141186A (en) | 2021-11-01 |
| JPWO2021177250A1 (en) | 2021-09-10 |
| WO2021177250A1 (en) | 2021-09-10 |
| KR20220149671A (en) | 2022-11-08 |
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