CN109997080A - Photoinitiator and shading photosensitive resin composition comprising it - Google Patents

Photoinitiator and shading photosensitive resin composition comprising it Download PDF

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Publication number
CN109997080A
CN109997080A CN201780073323.5A CN201780073323A CN109997080A CN 109997080 A CN109997080 A CN 109997080A CN 201780073323 A CN201780073323 A CN 201780073323A CN 109997080 A CN109997080 A CN 109997080A
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compound
chemical formula
resin composition
methyl
photosensitive resin
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CN201780073323.5A
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CN109997080B (en
Inventor
崔正植
金兑洙
金泰运
施允基
安廷珉
杨英恩
吴泉林
柳权壹
李德熙
李元重
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Samyang Corp
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Samyang Corp
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • 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
    • G03F7/09—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
    • 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
    • G03F7/16—Coating processes; Apparatus therefor

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

The present invention relates to a kind of photoinitiator and include its shading photosensitive resin composition, in more detail, it is related to a kind of photoinitiator and photosensitive resin composition, wherein, the photoinitiator contains the compound selected from chemical formula 1, more than two compounds in the compound of chemical formula 2 and the compound of chemical formula 3, the photosensitive resin composition shows the light-proofness of promotion comprising the photoinitiator, and show excellent deep curability, be conducive to the formation and developing process using photolithographic pattern, therefore the shading photosensitive resin composition for luminous organic material display panel can be suitable as.

Description

Photoinitiator and shading photosensitive resin composition comprising it
Technical field
It is related to one in more detail the present invention relates to a kind of photoinitiator and comprising its shading photosensitive resin composition Kind of photoinitiator and photosensitive resin composition, wherein the photoinitiator contains compound selected from chemical formula 1, chemical formula 2 More than two compounds in the compound of compound and chemical formula 3, the photosensitive resin composition include described light-initiated Agent and the light-proofness for showing promotion, and show excellent deep curability, be conducive to the shape using photolithographic pattern At and developing process, therefore the shading photosensitive resin composition for luminous organic material display panel can be suitable as.
Background technique
In recent years, it uses in equipment in display as the height more than ultrahigh resolution (Ultra Definition, UD) The element of resolution ratio and the high-speed driving of 240Hz or more just energetically studies low temperature polycrystalline silicon (Low Temperature Poly-Silicon, LTPS) and oxide thin film transistor.
In general, oxide thin film transistor makes the property of semiconductor change due to light, by importing shading Layer minimizes above-mentioned problem.After forming light shield layer, the subsequent techniques such as PE-CVD are carried out at high temperature, therefore as shading Layer mainly uses metal light shield layer.But due to the reflectivity of metal light shield layer height, light can reflect and enter source electrode, electric leakage Between pole and light shield layer, stray voltage is generated between source electrode, drain electrode, constitutes the factor for increasing the operating resistance of element, Therefore there are problems that the load of data line increases.
In particular, also light shield layer can be imported in luminous organic material display and transparent display, to eliminate upper metal The significantly reduced characteristic of contrast caused by the reflection of wiring and lower metal wiring.
The common examples of photoinitiator for photosensitive composition it has been known that there is acetophenone derivs, benzophenone derivates, Multiple types such as pyrrolotriazine derivatives, united imidazole derivative, acylphosphine oxide derivative and oxime ester derivative, wherein oxime ester derivative Have the advantages that and absorb ultraviolet light and hardly display color, free radical formation efficiency are high, and with photosensitive composition material The compatibility and excellent in stability of material.But the light-initiated low efficiency of the 9 oxime derivate compound of early development, especially in pattern In exposure technology, susceptibility is low, it is therefore desirable to increase light exposure, thus there are problems that yield tails off.It is such in order to improve Disadvantage proposes various oxime ester derivative compounds (for example, KR published patent 10-2001-0082580 as photoinitiator Number, No. 10-2007-0044753).
Summary of the invention
Technical problems to be solved
The purpose of the present invention is to provide a kind of photosensitive resin composition and it is particularly suitable for the photosensitive resin composition Photoinitiator, wherein the photosensitive resin composition shows the light-proofness of promotion, and shows excellent deep solidification Property, be conducive to the formation and developing process using photolithographic pattern, therefore can be suitable as aobvious for luminous organic material Show the shading photosensitive resin composition of panel.
Technical solution
To achieve the goals above, the present invention provides a kind of photoinitiator, contains the chemical combination selected from following chemical formula 1 More than two compounds in the compound of object, the compound of chemical formula 2 and chemical formula 3.
[chemical formula 1]
[chemical formula 2]
[chemical formula 3]
In the chemical formula 1 and chemical formula 2, R1To R3It is each independently hydrogen, halogen, alkyl, aryl, alkoxy, aralkyl Base, hydroxyalkyl, hydroxy alkoxy alkyl or naphthenic base, A are hydrogen, alkyl, aryl, alkoxy, aralkyl, hydroxyalkyl, hydroxyl alkane Oxygroup alkyl, naphthenic base, amino, nitro, cyano or hydroxyl.
In the chemical formula 3, R4To R6It is each independently hydrogen, halogen, alkyl, aryl, alkoxy, aralkyl, hydroxyl alkane Base, hydroxy alkoxy alkyl or naphthenic base.
In addition, according to another aspect of the present invention, providing a kind of shading photosensitive resin composition, it includes [A] alkali Soluble resin, [B] have polymerizable compound, [C] colorant and [D] described photoinitiator of unsaturated bond.
According to another aspect of the present invention, a kind of solidification formed by the shading photosensitive resin composition is provided Film.
Another one side according to the present invention provides a kind of display element comprising the cured film (for example, organic light emission Material shows (OLED) element).
Beneficial effect
Shading comprising photoinitiator of the invention shows the light-proofness of promotion with photosensitive resin composition, and shows Excellent deep curability out is conducive to formation and developing process using photolithographic pattern, therefore can be suitable as using In the shading photosensitive resin composition of luminous organic material display panel.
Specific embodiment
Hereinafter, the present invention will be described in more detail.
Photoinitiator of the invention contains the compound and chemical formula 3 of compound selected from following chemical formula 1, chemical formula 2 Compound in more than two oxime ester derivative compounds.
[chemical formula 1]
[chemical formula 2]
[chemical formula 3]
In the chemical formula 1 and chemical formula 2, R1To R3It is each independently hydrogen, halogen, alkyl, aryl, alkoxy, aralkyl Base, hydroxyalkyl, hydroxy alkoxy alkyl or naphthenic base, A are hydrogen, alkyl, aryl, alkoxy, aralkyl, hydroxyalkyl, hydroxyl alkane Oxygroup alkyl, naphthenic base, amino, nitro, cyano or hydroxyl.
In the chemical formula 3, R4To R6It is each independently hydrogen, halogen, alkyl, aryl, alkoxy, aralkyl, hydroxyl alkane Base, hydroxy alkoxy alkyl or naphthenic base.
Hereinbefore, specifically, the carbon atom number of alkyl and alkoxy can be 1 to 10, the carbon atom number of naphthenic base It can be 3 to 8, the carbon atom number of aryl can be 6 to 30.More specifically, the carbon atom number of alkyl and alkoxy can be 1 To 8, the carbon atom number of naphthenic base can be 3 to 6, and the carbon atom number of aryl can be 6 to 20.
More specifically, the R1To R6Hydrogen, bromine, chlorine, iodine, methyl, ethyl, n-propyl, isopropyl can be each independently Base, normal-butyl, isobutyl group, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohesyl, phenyl, naphthalene, xenyl, terphenyl Base, anthryl, indenyl, phenanthryl, methoxyl group, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, Methylol, ethoxy, hydroxy-n-propyl, hydroxy-n-butyl, hydroxyisobutyl, hydroxyl n-pentyl, hydroxyl isopentyl, hydroxyl just oneself Base, hydroxyl isohesyl, hydroxymethoxy methyl, hydroxymethoxy ethyl, hydroxymethoxy propyl, hydroxymethoxy butyl, hydroxyl Base oxethyl methyl, hydroxyl ethoxy ethyl, hydroxyethoxypropyl, hydroxyl-oxethyl butyl, hydroxyethoxypentyl or hydroxyl Base oxethyl hexyl；A can be hydrogen or nitro.
The compound of chemical formula 1 of the invention can typically enumerate more than one in following groups, but following Compound does not limit the present invention.
The compound of chemical formula 2 of the invention can typically enumerate more than one in following groups, but following Compound does not limit the present invention.
The compound of chemical formula 3 of the invention can typically enumerate more than one in following groups, but following Compound does not limit the present invention.
The chemical formula 1 for including in photoinitiator of the invention is not special to the content ratio between the compound of chemical formula 3 Limitation.
In one concrete example, using in the compound of chemical formula 1 to chemical formula 3 two compounds (the first compound and Second compound) when, the first compound: second compound can for example with 1:0.1 to 1:10, more specifically with 1:0.2 to 1:5, Further specifically with 1:0.5 to 1:2, further specifically used with the weight ratio of 1:0.8 to 1:1.3, but not limited to this.Its In, the first compound and second compound indicate two compounds in three compounds selected from chemical formula 1 to chemical formula 3, It can be chemical formula 1 and chemical formula 2, chemical formula 1 and chemical formula 3 or chemical formula 2 and chemical formula 3 respectively.
In another concrete example, when three compounds in the compound of all chemical formulas 1 to chemical formula 3 (first is used Compound is to third compound), the first compound: second compound: third compound can for example with 1:0.1~10:0.1~ 10, more specifically with 1:0.2~5:0.2~5, further specifically with 1:0.5~2:0.5~2, further specifically with 1:0.8~ The weight ratio of 1.3:0.8~1.3 uses, and but not limited to this.Wherein, the first compound, second compound and third chemical combination Object respectively indicates any one of three compounds of chemical formula 1 to chemical formula 3, they can be chemical formula 1, chemistry respectively Formula 2, chemical formula 3, chemical formula 1, chemical formula 3, chemical formula 2, chemical formula 2, chemical formula 1, chemical formula 3, chemical formula 2, chemical formula 3, Chemical formula 1, chemical formula 3, chemical formula 1, chemical formula 2 or chemical formula 3, chemical formula 2, chemical formula 1.
Shading of the invention photosensitive resin composition includes the polymerization of [A] alkali soluble resin, [B] with unsaturated bond Property compound, [C] colorant and [D] photoinitiator of the invention.
The excellent physical properties of the film of shading photosensitive resin composition of the invention, due to inhibiting to hinder to generate color difference The phenomenon that, and it is advantageous in terms of the solidification of deep, therefore be conducive to the formation of pattern.
Shading of the invention can with [A] alkali soluble resin for being included as adhesive resin in photosensitive resin composition To use the acryl adhesive resin (acrylic of acrylic polymer or side chain with acrylic acid unsaturated bond Object), organosilicon (silicone) class adhesive resin, more (cardo) the class adhesive resins of card and acid imide adhesive resin.
Although it's not limited to that, from (such as the regulation and heat resistance and resistance to of pattern properties of the physical property of film Angle chemically etc.), the content for the alkali soluble resin for including in 100 weight % of photosensitive resin composition of the invention Preferably 3~50 weight %, more preferably 5~40 weight %.In addition, the weight average molecular weight of alkali soluble resin is preferably 2, 000 to 300,000, more preferably 4,000 to 100,000.In addition, the dispersion degree of alkali soluble resin is preferably 1.0 to 10.0.
In one concrete example, the acrylic polymer can be comprising acrylic monomer including monomer (total) Polymer.The example of this acrylic monomer can enumerate (methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) third Olefin(e) acid propyl ester, (methyl) butyl acrylate, (methyl) amyl acrylate, (methyl) Hexyl 2-propenoate, (methyl) acrylate Ester, (methyl) heptylacrylate, (methyl) 2-ethyl hexyl acrylate, (methyl) nonyl acrylate, (methyl) decyl acrylate, (methyl) Lauryl acrylate, (methyl) dodecylacrylate, (methyl) acrylic acid tetradecane base ester, (methyl) acrylic acid hexadecane Base ester, (methyl) isobornyl acrylate, (methyl) adamantyl acrylate, (methyl) dicyclopentyl acrylate, (first Base) acrylic acid dicyclopentenyl base ester, (methyl) benzyl acrylate, 2- methoxy ethyl (methyl) acrylate, 2- ethyoxyl second Base (methyl) acrylate, (methyl) acrylic acid, itaconic acid, maleic acid, maleic anhydride, maleic acid mono alkyl ester, itaconic acid list Arrcostab, monoalkyl esters, (methyl) glycidyl acrylate, 3,4- epoxybutyl (methyl) acrylate, 2,3- Epoxycyclohexyl (methyl) acrylate, 3,4- epoxycyclohexyl-methyl (methyl) acrylate, 3- methy oxetane -3- Methyl (methyl) acrylate, 3- Ethyloxetane -3- methyl (methyl) acrylate, (methyl) acrylamide, N- first Base (methyl) acrylamide etc., they can respectively be used alone or two or more be used together.In addition, can also in the present invention With use this acrylic monomer and styrene, α-methylstyrene, acetoxy-styrene, N- methylmaleimido, The monomers such as n-ethylmaleimide, N- propylmaleimide, N- butyl maleimide, N- N-cyclohexylmaleimide into The copolymer of row copolymerization and acquisition.
In one concrete example, there is the side chain acrylic polymer of acrylic acid unsaturated bond can be containing carboxylic acid Acrylic copolymer and epoxy resin carry out addition reaction acquisition copolymer.For example, by the acrylic compounds containing carboxylic acid Copolymer and epoxy monomer (such as glycidyl acrylate, glycidyl methacrylate, 3,4- epoxybutyl (methyl) Acrylate, 2,3- epoxycyclohexyl (methyl) acrylate, 3,4- epoxycyclohexyl-methyl (methyl) acrylate etc.) 40 The copolymer for carrying out addition reaction at a temperature of~180 DEG C and obtaining can be used as adhesive resin, wherein described contain carboxylic acid Acrylic copolymer is by containing acrylic acid, methacrylic acid, itaconic acid, maleic acid, maleic acid mono alkyl ester etc. There are the acrylic monomer of carboxylic acid and (methyl) alkyl acrylate of (methyl) methyl acrylate, (methyl) Hexyl 2-propenoate etc. Base ester, (methyl) cyclohexyl acrylate, (methyl) isobornyl acrylate, (methyl) adamantyl acrylate, (methyl) third Olefin(e) acid bicyclopentyl ester, (methyl) acrylic acid dicyclopentenyl base ester, (methyl) benzyl acrylate, 2- methoxy ethyl (methyl) third Olefin(e) acid ester, 2- ethoxyethyl group (methyl) acrylate, styrene, α-methylstyrene, acetoxy-styrene, N- methyl horse Come acid imide, n-ethylmaleimide, N- propylmaleimide, N- butyl maleimide, N- cyclohexyl maleimide Amine, (methyl) acrylamide, N- methyl (methyl) acrylamide etc. are copolymerized and are obtained.
There is side chain another example of the acrylic polymer of acrylic acid unsaturated bond, which can enumerate, will contain epoxy group Acrylic copolymer and carboxylic acid carry out addition reaction acquisition copolymer.For example, the acrylic compounds containing epoxy group are total to Polymers and acrylic monomer (such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, maleic acid mono alkyl containing carboxylic acid Ester etc.) 40~180 DEG C at a temperature of carry out addition reaction and the copolymer that obtains can be used as adhesive resin, wherein described contain Having the acrylic copolymer of epoxy group to pass through will such as glycidyl acrylate, glycidyl methacrylate, 3,4- Epoxybutyl (methyl) acrylate, 2,3- epoxycyclohexyl (methyl) acrylate, 3,4- epoxycyclohexyl-methyl (methyl) (the first such as the acrylic monomer containing epoxy group and (methyl) methyl acrylate, (methyl) Hexyl 2-propenoate of acrylate etc. Base) alkyl acrylate, (methyl) cyclohexyl acrylate, (methyl) isobornyl acrylate, (methyl) acrylic acid adamantyl Ester, (methyl) dicyclopentyl acrylate, (methyl) acrylic acid dicyclopentenyl base ester, (methyl) benzyl acrylate, 2- methoxyl group Ethyl (methyl) acrylate, 2- ethoxyethyl group (methyl) acrylate, styrene, α-methylstyrene, acetyloxy phenyl Ethylene, N- methylmaleimido, n-ethylmaleimide, N- propylmaleimide, N- butyl maleimide, N- ring The monomers such as hexyl maleimide, (methyl) acrylamide, N- methyl (methyl) acrylamide are copolymerized and are obtained.
In one concrete example, the silicone adhesive resin contains the polymerized unit of the expression of following chemical formula 4.
[chemical formula 4]
X-R7SiO(4-n)/2
In the chemical formula 4, R7It is alkylidene, the carbon atom number 6 of straight-chain or branched that carbon atom number is 1 to 20 To 20 arlydene, total carbon atom number be 7 to 20 aryl-alkylidene, total carbon atom number be 7 to 20 alkyl-arylene or The alkylene-arylene that total carbon atom number is 7 to 20；X is hydroxyl, carboxylic acid group, acid anhydride, polycalboxylic. anhydride derivative's base, acyl Asia Amido, imide derivative base, amide groups, amide derivatives base, amido or sulfydryl；N is 0 to 3 integer；The polymerization list of n=3 Member can not be that 3 other polymerized units are used together with n.
In addition, it is, for example, possible to use be selected from tetraalkoxysilane, trialkoxy silane, methyl trialkoxysilane, ethyl Trialkoxy silane, n-propyl trialkoxy silane, isopropyl trialkoxy silane, normal-butyl trialkoxy silane, tert-butyl Trialkoxy silane, phenyl trialkoxysilane, naphthalene trialkoxy silane, vinyl trialkyl oxysilane, methacryl Oxygroup methyl trialkoxysilane, 2- methacryloxyethyl trialkoxy silane, 3- methacryloxypropyl three Alkoxy silane, 3- methacryloyloxypropyl methyl dialkoxy silicane, 3- methacryloxypropyl ethyl dioxane Oxysilane, acryloyloxymethyl trialkoxy silane, 2- acryloyl-oxyethyl trialkoxy silane, 3- acryloxy Propyl trialkoxy silane, 3- acryloxypropyl dialkoxy silicane, 3- acryloxypropyl ethyl dialkoxy Base silane, 3- glycydoxy trialkoxy silane, 2- epoxycyclohexylethyl trialkoxy silane, 3- epoxide ring Hexyl propyl trialkoxy silane, dimethyl alkoxy silane, diethyl dialkoxy silicane, dipropyl dialkoxy silicane, The list of one or more of diphenyl dialkoxy silicane, diphenyl silanodiol and phenyl methyl dialkoxy silicane Body.Wherein, alkoxy can be straight-chain, branched or cricoid aliphatic or the aromatic series alcoxyl that carbon atom number is 1 to 7 Base.In addition, hydrolyzable halogenated organo-silicon compound also are used as monomer.
In one concrete example, the card multiclass adhesive resin contains the poly- of the compound indicated from following chemical formula 5 Close unit.
[chemical formula 5]
In the chemical formula 5, R9Be each independently hydrogen orR10And R11It is same or different to each other, respectively Independently being straight-chain, branched or cricoid alkyl that hydrogen, hydroxyl, carbon atom number are 1 to 20 or carbon atom number is 6 to 10 Aryl；R12Be straight-chain, branched or cricoid alkyl, carbon atom number that hydrogen, carbon atom number are 1 to 20 be 6 to 10 aryl, The unsaturated alkyl or-C (=O)-R that carbon atom number is 2 to 1012’, wherein R12’Be hydrogen, hydroxyl, carbon atom number be 1 to 20 it is straight The aryl that chain, branched or cricoid alkyl or carbon atom number are 6 to 10；Y isIts Middle R13、R14And R15It is same or different to each other, is each independently hydrogen, the straight-chain that carbon atom number is 1 to 20, halogen replace The aryl that straight-chain, branched or cricoid alkyl or carbon atom number are 6 to 10.
In one concrete example, the acid imide adhesive resin contains the compound indicated from following chemical formula 6 Polymerized unit.
[chemical formula 6]
In the chemical formula 6, R16Be each independently hydrogen, hydroxyl, carbon atom number be 1 to 20 straight-chain, branched or The aryl that cricoid alkyl or carbon atom number are 6 to 10；R17It is hydrogen, straight-chain, branched or ring-type that carbon atom number is 1 to 20 Alkyl, carbon atom number be 6 to 10 aryl, carbon atom number be 2 to 10 unsaturated alkyl orWherein R18It is Straight-chain that straight-chain, branched or cricoid alkyl, the carbon atom number that hydrogen, hydroxyl, carbon atom number are 1 to 20 are 2 to 20, branch The aryl that chain or cricoid alkenyl or carbon atom number are 6 to 10.
Shading of the invention with [B] for including in photosensitive resin composition there is the polymerizable compound of unsaturated bond to play It is crosslinked by light reaction when forming pattern to form the effect of pattern, when high-temperature heating crosslinks and assigns chemically-resistant Property and heat resistance.
Although it's not limited to that, include in 100 weight % of photosensitive resin composition of the invention is described with insatiable hunger It for example can be 0.001~40 weight % with the content of the polymerizable compound of key, more specifically can be 0.01~30 weight %. If adding the excessive polymerizable compound with unsaturated bond in photosensitive resin composition, the degree of cross linking becomes excessively high, leads The shortcomings that causing the ductility reduction of pattern.
In one concrete example, the polymerizable compound with unsaturated bond can be the polymerization with hydroxy or carboxy Property unsaturated compound.
In one concrete example, the polymerizable compound with unsaturated bond can enumerate (methyl) methyl acrylate, (first Base) ethyl acrylate, (methyl) butyl acrylate, 2- ethylhexyl (methyl) acrylate, (methyl) lauryl acrylate etc. The Arrcostab of (methyl) acrylic acid；(methyl) glycidyl acrylate, Oxyranyle quantity be 2 to 14 polyethylene glycol Single (methyl) acrylate, ethylene glycol two (methyl) acrylate, Oxyranyle quantity be 2 to 14 polyethylene glycol two (methyl) acrylate, propylene oxide base quantity be 2 to 14 polypropylene glycol two (methyl) acrylate, trimethylolpropane Two (methyl) acrylate, bisphenol A diglycidyl ether acrylic acid adduct, two hydroxyl ethyl ester of (methyl) acrylic acid O-phthalic Acid diesters, the tolylene diisocyanate adduct of two hydroxyl ethyl ester of (methyl) acrylic acid, trimethylolpropane tris (methyl) acrylic acid Ester, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylic acid Polyalcohols and α, β-two insatiable hungers such as ester, dipentaerythritol six (methyl) acrylate, dipentaerythritol three (methyl) acrylate The compound of esterification acquisition, the glycidyls such as trihydroxymethylpropanyltri diglycidyl ether acrylic acid adduct are carried out with carboxylic acid The acrylic acid adduct etc. of object is closed, they can respectively be used alone or two or more be used together.
Shading of the invention is played to the film formed by composition with [C] colorant for including in photosensitive resin composition and is assigned Give the effect of light-proofness.
Although it's not limited to that, the colorant that includes in 100 weight % of photosensitive resin composition of the invention Content for example can be 3~40 weight %, more specifically can be 5~30 weight %.If the colorant in photosensitive resin composition Content it is very few, then light-proofness be deteriorated, on the other hand, if the content of the colorant in photosensitive resin composition is excessive, can lead The craftsmanship for forming the pattern of photomask is caused to reduce.
In one concrete example, the colorant can enumerate black carbon black, titanium, nigrosine, black (perylene black), interior Amido black (lactam black) and C.I. pigment black 7 etc., they can respectively be used alone or two or more be used together.
It include [D] above-mentioned photoinitiator of the invention in shading photosensitive resin composition of the invention.
Although it's not limited to that, from the generation for minimizing the reflectivity, inhibition color difference of shading with photoresist and smoothly The cured angle in deep is realized on ground, the photoinitiator for just including in 100 weight % of photosensitive resin composition of the invention For content, the compound of compound to the chemical formula 3 of chemical formula 1 be each independently 0.01~10 weight % be it is effective, 0.1~5 weight % is more effective.
In shading photosensitive resin composition of the invention, other than comprising [A] to [D] ingredient, as needed It also may include that there is the organosilicon compound of epoxy group or amido as bonding agent.
The organosilicon compound can be used for being promoted the bonding force of ITO electrode and photosensitive resin composition, and increase solid Heat-resistant quality after change, relative to the composition of 100 weight %, usage amount can be 0.0001~3 weight %, but and unlimited Due to this.
In one concrete example, the organosilicon compound with epoxy group or amido can enumerate (3- glycidoxy Propyl) trimethoxy silane, (3- glycidoxypropyl group) triethoxysilane, (3- glycidoxypropyl group) methyl dimethoxy oxygen Base silane, (3- glycidoxypropyl group) methyldiethoxysilane, (3- glycidoxypropyl group) dimethyl methoxy silane, (3- glycidoxypropyl group) dimethylethoxysilane, 3,4- epoxybutyl trimethoxy silane, three second of 3,4- epoxybutyl Oxysilane, 2- (3,4- epoxycyclohexyl) ethyl trimethoxy silane, 2- (3,4- epoxycyclohexyl) ethyl triethoxy silicane Alkane, TSL 8330 etc., they can respectively be used alone or two or more be used together.
In addition, as needed, shading photosensitive resin composition of the invention also may include more than one as photosensitizer, Thermal polymerization inhibitor, defoaming agent, levelling agent, dispersing agent etc. have the additive of compatibility.
In addition, as needed, shading photosensitive resin composition of the invention can be further containing selected from thioxanthene ketone class Close object, ketone compounds, bisglyoxaline class compound, compound in triazine class, O- acyl group oxime (O-acyloxime) class compound or sulphur The compound of one or more of alcohol compound.
Shading of the invention forms pattern with photosensitive resin composition by the following method: addition solvent is simultaneously enterprising in substrate Then row spin coating irradiates ultraviolet light using exposure mask, is developed with alkaline-based developer, it is preferable that the group relative to 100 weight % Object is closed, the solvent of 10~95 weight % is added, by viscosity-adjusting agent to 1~50cps range.
For the solvent, it is contemplated that the compatibility with adhesive resin, photoinitiator and other compounds can incite somebody to action Ethyl acetate, butyl acetate, diethylene glycol dimethyl ether, diethylene glycol dimethylether, methoxy methyl propionate, ethoxy-propionic acid Ethyl ester (EEP), ethyl lactate, propylene glycol methyl ether acetate (PGMEA), propylene glycol monomethyl ether acetate (PGMEP), propylene glycol first Ether, propylene glycol propyl ether, methyl acetate cellosolve (methyl cellosolve acetate), ethyl acetate cellosolve, diethyl two Alcohol methyl acetate, diethylene glycol ethyl acetate, acetone, methyl iso-butyl ketone (MIBK), cyclohexanone, dimethylformamide (DMF), N, N- bis- Methylacetamide (DMAc), n-methyl-2-pyrrolidone (NMP), gamma-butyrolacton, diethyl ether, glycol dimethyl ether, diethylene glycol (DEG) Dimethyl ether (Diglyme), tetrahydrofuran (THF), methanol, ethyl alcohol, propyl alcohol, isopropanol, methyl cellosolve, ethyl cellosolve, two Ethylene glycol monomethyl ether, diethylene glycol ether, dipropylene glycol methyl ether, toluene, dimethylbenzene, hexane, heptane, octane equal solvent are respectively independent Using or two or more be used in mixed way.
In one concrete example, solvent as described above be may be included in shading photosensitive resin composition of the invention.? In this case, the content of solvent is in the total weight of composition by the surplus except the content of remaining ingredient in composition.
Hereinafter, enumerating Examples and Comparative Examples to representative chemical combination of the invention in order to detailed understanding of the invention Object is described in detail.But the embodiment of the present invention can be deformed into various other embodiments, should not be construed as of the invention Range is defined in embodiment described below.The embodiment of the present invention be in order to those skilled in the art more completely Illustrate the present invention and provides.
[embodiment]
Synthesis example: the preparation of alkali soluble resin
A) preparation of A-1 resin
200mL propylene glycol methyl ether acetate (Propylene Glycol Methyl Ether Acetate, PGMEA) in addition 1.5g azodiisobutyronitrile (Azobisisobutyronitrile, AIBN) after, by methacrylic acid, Glycidyl methacrylate, methyl methacrylate and dicyclopentyl acrylate (dicyclopentanyl Acrylate) then existed with the molar ratio of 20:20:40:20 (solid content of acrylic monomer: 40 weight %) addition respectively Under nitrogen atmosphere, stirs and polymerize 5 hours at 70 DEG C, prepare acrylic polymer A-1 resin.It confirmed to make as described above The weight average molecular weight of standby copolymer is 25,000.
B) preparation of A-2 resin
By 3- (triethoxysilyl) methyl propionate (methyl3- of 62.5g (0.05 mole) (triethoxysilyl) propionate), the bicycloheptane ethyl triethoxy silicane alkane of 51.6g (0.04 mole) The third the two of (bicycloheptanyltriethoxy silane), the methyltrimethoxysilane of 6.8g (0.01 mole), 200g Alcohol methyl ether acetate is quantified and is mixed, and the solution of acquisition is stirred, while being added dropwise 10.4g's (0.02 mole) The mixed liquor of the tetrahydrofuran of 35% aqueous hydrochloric acid solution, the water of 47.2g and 50g.It completes after being added dropwise, reaction temperature is warming up to 85 DEG C, heating at a temperature of carry out reaction 6 hours.After reaction, the suitable tetrahydrofuran of evaporative removal and methanol add second Ether (ether), water recycle organic phase, evaporative removal remnants alcohol and solvent after extracting, obtain the silicone resin of 54g.It will The silicone resin of acquisition is dissolved in the propylene glycol methyl ether acetate of 125.5g.The siloxane polymer prepared as described above The weight average molecular weight of A-2 resin is 6,000.
C) preparation of A-3 resin
At 120 DEG C, by bis- (the 4- glycidyl oxo phenyl) fluorenes of 9, the 9- of 231g, 150mg tetrabutylammonium chloride and The propionic acid of 74g is heated and is reacted 12 hours.Reaction is terminated by analyzing propionic acid with GC, the intermediate for obtaining solid phase (is received Rate: 92%).The intermediate of the solid phase obtained of 280g is dissolved in the propylene glycol methyl ether acetate (Propylene of 400mL Glycol Methyl Ether Acetate, PGMEA) in, then add 3,3', 4, the 4'- biphenyltetracarboxyacid acids two of 101.4g The tetrabutylammonium chloride of acid anhydride, 500mg, and reacted at 120 DEG C.Finally, the phthalic anhydride of 35g is mixed, It is terminated after being reacted at 90 DEG C, obtains card multiclass polymer A-3 resin.Weight average molecular weight is 3,800.
C) preparation of A-4 resin
At 120 DEG C, by bis- (the 4- glycidyl oxo phenyl) fluorenes of 9, the 9- of 231g, 150mg tetrabutylammonium chloride, The 2,6 di tert butyl 4 methyl phenol of 100mg and the acrylic acid of 72g are heated and are reacted 12 hours.By being analyzed with GC Acrylic acid reacts to terminate, and obtains the intermediate (yield: 92%) of solid phase.The intermediate of the solid phase obtained of 280g is dissolved In the propylene glycol methyl ether acetate (Propylene Glycol Methyl Ether Acetate, PGMEA) of 400mL, then 3,3', 4, the 4'- biphenyltetracarboxylic dianhydrides of 101.4g, the tetrabutylammonium chloride of 500mg are added, and are reacted at 120 DEG C. Finally, the phthalic anhydride of 35g is mixed, is terminated after being reacted at 90 DEG C, obtain card multiclass polymer A-4 resin. Weight average molecular weight is 4,800.
D) preparation of A-5 resin
By the bis- (fluoroforms of 2,2'- of the 2,2- of 20.1g bis- (3- amino-4-hydroxylphenyl)-hexafluoropropane and 17.6g Base) -4,4'- benzidine is dissolved in propylene glycol methyl ether acetate (the Propylene Glycol Methyl of 180mL Ether Acetate, PGMEA) in, then slowly add 5- (2,5- dioxotetrahydrofuryl) -3- methyl-of 14.5g 3- cyclohexene -1,2- dicarboxylic anhydride is reacted, and 4,4'- (hexafluoroisopropylidenyl), two phthalic acid of 24.4g is then added Acid anhydride reacts 4 hours at 25 DEG C, reacts 20 hours at 50 DEG C, obtains imide polymer A-5 resin.Weight average molecular weight is 2,800。
E) preparation of A-6 resin
By bis- (3- aminopropyl) tetramethyl disiloxanes of the 1,3- of the 4,4'- diaminodiphenyl ether of 114g, 12.3g and The 3- amino-phenol of 81.8g is dissolved in the n-methyl-2-pyrrolidone (NMP) of 800g.Later, the double of 310g are added together The NMP of (3,4- dicarboxyphenyi) ether dianhydride and 200g reacts 1 hour at 20 DEG C, reacts 4 hours at 50 DEG C.Later, add The dimethylbenzene for adding 150g terminates reaction after stirring 5 hours at 150 DEG C.Precipitate the resin terminated after reacting in purified water, And washed, it is 20 hours dry in 80 DEG C of vacuum drier, obtain acid imide polymer A-6 resin.Weight-average molecular Amount is 15,000.
Examples 1 to 28 and comparative example 1~6: the preparation of photosensitive resin composition
[A] alkali-soluble tree of 20 weight % is added in the reaction mixing channel for being provided with ultraviolet screener film and blender Rouge (solid content is 50 weight %, is dissolved in solvent (PGMEA)), [B] dipentaerythritol hexaacrylate of 5 weight %, 20 [C] lactams of weight % black (solid content is 25 weight %, is dispersed in PGMEA), 0.5 weight % [D] photoinitiator and Other additive FC-430 (levelling agent of 3M company, 0.1 weight %), are stirred at normal temperature, then add the molten of surplus Agent prepares photosensitive resin composition so that total composition becomes 100 weight %.It is used in each Examples and Comparative Examples Alkali soluble resin type and photoinitiator type and content it is as described in Table 1.
[compound 1]
[compound 2]
[compound 3]
[chemical formula 4]
[chemical formula 5]
[table 1]
<evaluation of physical property>
Susceptibility, the pattern for measuring the photosensitive resin composition prepared in the Examples 1 to 28 and comparative example 1~6 are special The performances such as property, and its evaluation result is shown in following table 2.
1) it is used for the light exposure of critical dimension
Spin coating resin combination on the glass substrate after carrying out the pre-heat treatment 90 seconds at 120 DEG C, forms about 1.3 μ m-thicks The film of degree.It using photomask, is exposed with high-pressure mercury-vapor lamp, from 20mJ/cm2Start, increases 10mJ/cm every time2, then Develop in 2.38% tetramethylammonium hydroxide (Tetramethylammonium hydroxide, TMAH) aqueous solution.It Afterwards, it is washed and is dried with pure water, be heat-treated 30 minutes after being carried out in 230 DEG C of convection oven, form shading figure Case.For susceptibility, the exposure that is saturated the size of the negative pattern of critical dimension (Critical dimension, C.D.) Light quantity is expressed as the susceptibility of each sample.
2) reach the light exposure adhered to after developing process
Spin coating photoresist on the glass substrate after carrying out the pre-heat treatment 90 seconds at 120 DEG C, forms about 1.3 μ m thicks Film.It using photomask, is exposed with high-pressure mercury-vapor lamp, from 20mJ/cm2Start, increases 10mJ/cm every time2, then exist Develop in 2.38%TMAH aqueous solution.After development, according to not sentencing 10 μm of peeling-off light exposures of thread pattern Determine pattern adhesiveness.
3) surface cure degree
It is exposed with the light exposure determined in above-mentioned sensitivity assessment, and after being developed, shading is generated on surface The quantity of pin hole be determined as zero when being less than 0~3 in 10mm × 10mm, be determined as Δ when less than 3~7, at 7 or more It is determined as X.
4) developing process characteristic
After being exposed with the light exposure determined in above-mentioned sensitivity assessment, develop, by the development of non-exposed part Time is set as BT, and removing (peeling) time of 10 μm of thread patterns of exposed portion is set as BP, therefore, it is determined that developing process is wide Content (BP-BT).
5) pattern lines
Using spin coater, shading is coated on substrate with composition, then to by prebake conditions (pre-bake), exposure The linearity for the shading pattern that the technique of light, rear baking (post-bake) and development is formed is confirmed.Pattern does not have crumple Or it is determined as zero when tearing, pattern occurs to be determined as Δ when one of crumple or tearing, while occurring to sentence when crumple and tearing It is set to X.
[table 2]

Claims (12)

1. a kind of photoinitiator, contain compound selected from following chemical formula 1, chemical formula 2 compound or chemical formula 3 change More than two compounds in object are closed,
[chemical formula 1]
[chemical formula 2]
[chemical formula 3]
In the chemical formula 1 and chemical formula 2,
R1To R3Be each independently hydrogen, halogen, alkyl, aryl, alkoxy, aralkyl, hydroxyalkyl, hydroxy alkoxy alkyl or Naphthenic base,
A is hydrogen, alkyl, aryl, alkoxy, aralkyl, hydroxyalkyl, hydroxy alkoxy alkyl, naphthenic base, amino, nitro, cyano Or hydroxyl,
In the chemical formula 3,
R4To R6Be each independently hydrogen, halogen, alkyl, aryl, alkoxy, aralkyl, hydroxyalkyl, hydroxy alkoxy alkyl or Naphthenic base.
2. photoinitiator according to claim 1, wherein the compound of chemical formula 1 be one in following groups with It is upper:
The compound of chemical formula 2 is more than one in following groups:
The compound of chemical formula 3 is more than one in following groups:
3. photoinitiator according to claim 1, wherein use two changes in the compound of chemical formula 1 to chemical formula 3 It closes object (the first compound and second compound), wherein the first compound: the weight ratio of second compound is 1:0.1 to 1:10.
4. photoinitiator according to claim 1, wherein using all chemical formulas 1 into the compound of chemical formula 3 three A compound (the first compound to third compound), wherein the first compound: second compound: the weight ratio of third compound It is 1:0.1~10:0.1~10.
5. a kind of shading photosensitive resin composition, it includes:
[A] alkali soluble resin；
[B] has the polymerizable compound of unsaturated bond；
[C] colorant；And
[D] photoinitiator described in any one of Claims 1-4.
6. shading photosensitive resin composition according to claim 5, wherein [A] alkali soluble resin is selected from propylene One or more of acid resin, organic silicon resin, card multiclass resin or imide resin.
7. shading photosensitive resin composition according to claim 5, wherein [B] has the polymerism of unsaturated bond Closing object is the polymerizable unsaturated compound with hydroxy or carboxy.
8. shading photosensitive resin composition according to claim 5, wherein [C] colorant be selected from carbon black, titanium it is black, Nigrosine, black, lactams be black or one or more of C.I. pigment black 7.
9. shading photosensitive resin composition according to claim 5, wherein with 100 weight % of photosensitive resin composition On the basis of, the amount of the compound of the compound of chemical formula 1 present in [D] photoinitiator to chemical formula 3 is each independently 0.01~10 weight %.
10. shading photosensitive resin composition according to claim 5, wherein the photosensitive resin composition is further Containing selected from thioxanthene ketone class compound, ketone compounds, bisglyoxaline class compound, compound in triazine class, O- acyl group oximes chemical combination The compound of one or more of object or sulfur alcohol compound.
11. a kind of cured film, the shading as described in any one of claim 5 to 10 is formed with photosensitive resin composition.
12. a kind of display element, it includes the cured films described in claim 11.
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