CN109312170A

CN109312170A - Compound and photosensitive resin composition comprising it

Info

Publication number: CN109312170A
Application number: CN201880002348.0A
Authority: CN
Inventors: 崔相雅; 朴锺镐; 金圣勋; 梁承秦; 李多美; 朴相均; 金载骏; 李在容; 李修莲; 郑智惠
Original assignee: LG Chemical Co Ltd; Industry Academic Cooperation Foundation of KNU
Current assignee: LG Chem Ltd; LG Corp; Industry Academic Cooperation Foundation of KNU
Priority date: 2017-04-13
Filing date: 2018-03-20
Publication date: 2019-02-05
Anticipated expiration: 2038-03-20
Also published as: CN109312170B; KR102131992B1; KR20180115585A; JP6753597B2; WO2018190526A1; TWI663216B; TW201842075A; JP2019523760A

Abstract

The present invention relates to new chemical structure compound and comprising its photosensitive resin composition and by using its manufacture light-sensitive material, colour filter and display device.

Description

Compound and photosensitive resin composition comprising it

Technical field

Cross reference to related applications

This application claims preferential on April 13rd, 2017 South Korea patent application submitted the 10-2017-0048106th The equity of power, the entire disclosure are incorporated herein by reference.

The present invention relates to compound, comprising its photosensitive resin composition and by using its manufacture light-sensitive material, Colour filter and display device.More particularly it relates to the chemical combination with excellent color characteristics, heat resistance and solvent resistance Object；Use its photosensitive resin composition；And light-sensitive material, colour filter and the display device manufactured by using it.

Background technique

For present colour filter, need include high brightness and high contrast performance characteristics.In addition, exploitation display device One of main purpose be to distinguish the performance of display device by improving excitation purity and be to improve in manufacturing process Productivity.

It is photic that pigment type due to being used as the color material of existing colour filter with the state that particle disperses is present in color In resist, therefore the size by adjusting granules of pigments and distribution have difficulties to adjust brightness and contrast.In pigment In the case where grain, particle is assembled in colour filter, reduces dissolution characteristics and dispersing characteristic due to aggregated bulky grain, And many light scatterings occur.The scattering of the polarised light is considered as the principal element for reducing contrast.

Therefore, it has been carried out to be formed by the ultra-fine grain of pigment with dispersion stability and improves brightness and contrast's Research, but the freedom degree for realizing the selection of the color material of the chromaticity coordinates of high color purity display device is restricted.

In addition, the pigment dispersion method using color material especially pigment developed, which has had reached, uses this method Raising colour filter excitation purity, the limit of brightness and contrast.

Therefore, it is necessary to develop that the new color material of color rendering, brightness and contrast can be improved by increasing excitation purity Material.

Summary of the invention

Technical problem

It is an object of the present invention to provide the compounds with excellent color characteristics, heat resistance and solvent resistance.

It is a further object to provide the photosensitive resin compositions for using the above compound.

A further object of the present invention is to provide the colour filter by using the above compound or photosensitive resin composition manufacture Device and display device.

Technical solution

Present description provides the compounds indicated by chemical formula 1.

This specification additionally provides the color material composition comprising the above compound.

In addition, present description provides the photosensitive resin compositions comprising the compound or color material composition.

This specification is additionally provided by using the light-sensitive material of photosensitive resin composition manufacture and using described photosensitive The colour filter or display device of material.

Hereinafter, the compound of specific embodiment according to the present invention and the photosensitive tree comprising it will be described in further detail Oil/fat composition.

This specification in the whole text, when a part of one constituent element of " comprising ", unless otherwise specific descriptions, otherwise this is simultaneously It is not intended to exclude other constituent element, and referring to can also include other constituent element.

In the present specification, the example of substituent group is described as follows, but not limited to this.

As it is used herein, term " being substituted " means to become in addition with the hydrogen atom of the carbon atom bonding of compound Substituent group, and there is no limit as long as the position is that the substituted position of hydrogen atom i.e. substituent group can be with for position to be replaced Substituted position, and when two or more are substituted, two or more substituent groups can be mutually the same or not Together.

As it is used herein, term " be substituted or be unsubstituted " means by selected from the following one or more Substituent group is replaced: deuterium, halogen group, cyano, nitro, hydroxyl, carbonyl, ester group, imide, amino, carboxyl, sulfonic acid Base, sulfophenyl, oxidation phosphino-, alkoxy, aryloxy group, alkyl sulfenyl, artyl sulfo, alkyl sulphonyl, aryl sulfonyl, first silicon Alkyl, boryl, alkyl, naphthenic base, alkenyl, aryl, aralkyl, arylalkenyl, alkylaryl, aryl phosphino- include N, O and S The heterocycle of at least one of atom does not have substituent group, or by two in wherein illustrative substituents or more The substituent group of multiple substituent group connections is replaced or is not had substituent group.For example, " two of them or more replace term The substituent group of base connection " can refer to xenyl.That is, xenyl can be aryl, or it can be interpreted two of them phenyl The substituent group of connection.

In the present specification,Or-mean the key for being connected to another substituent group, and singly-bound means wherein another atom Be not present in by L indicate part when the case where.

In the present specification, the example of halogen group includes fluorine, chlorine, bromine and iodine.

In the present specification, the carbon atom number in imide is not particularly limited, it is preferred that being 1 to 30.Specifically, Imide can be the compound having following structure, but not limited to this.

In the present specification, in amide groups, the nitrogen of amide groups can be through hydrogen, the straight chain with 1 to 30 carbon atom, branch Change or cyclic alkyl or the aryl with 6 to 30 carbon atoms replace.Specifically, amide groups can have following structure Compound, but not limited to this.

In the present specification, the carbon atom number in carbonyl is not particularly limited, it is preferred that being 1 to 30.Specifically, carbonyl It can be the compound having following structure, but not limited to this.

In the present specification, ester group can have with flowering structure: wherein the oxygen of ester group can be had 1 to 25 carbon atom Straight chain, branching or cyclic alkyl or aryl with 6 to 25 carbon atoms replace.Specifically, ester group can for with The compound of flowering structure, but not limited to this.

In the present specification, sulfophenyl can be-SO₂NR ' R ", wherein R ' and R " is same or different to each other, and can be with It is each independently selected from hydrogen, deuterium, itrile group, the monocycle or polycyclic naphthene with 3 to 30 carbon atoms for being substituted or being unsubstituted Base, the straight chain with 1 to 30 carbon atom for being substituted or being unsubstituted or branched-alkyl are substituted or what is be unsubstituted has The monocycle or polyaromatic of 6 to 30 carbon atoms and the monocycle with 2 to 30 carbon atoms for being substituted or being unsubstituted or Polyheteroaromatic.

In the present specification, alkyl can be to be straight chain or branching, and its carbon atom number is not particularly limited, still Preferably 1 to 40.According to an embodiment, alkyl has 1 to 20 carbon atom.According to another embodiment, alkyl tool There is 1 to 10 carbon atom.According to another embodiment, alkyl has 1 to 6 carbon atom.The specific example of alkyl includes first Base, ethyl, propyl, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, tert-butyl, sec-butyl, 1- methyl-butvl, 1- second Base-butyl, amyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- methyl amyl, 2- methyl amyl, 4- Methyl -2- amyl, 3,3- dimethylbutyl, 2- ethyl-butyl, heptyl, n-heptyl, 1- methylhexyl, cyclopentyl-methyl, cycloheptyl Ylmethyl, octyl, n-octyl, t-octyl, 1- methylheptyl, 2- ethylhexyl, 2- propylpentyl, n-nonyl, 2,2- dimethyl Heptyl, 1- Ethyl-propyl, 1,1- Dimethyl-propyl, isohesyl, 2- methyl amyl, 4- methylhexyl, 5- methylhexyl etc., but It is without being limited thereto.

In the present specification, naphthenic base is not particularly limited, but its carbon atom number is preferably 3 to 60.According to a reality Scheme is applied, naphthenic base has 3 to 30 carbon atoms.According to another embodiment, naphthenic base has 3 to 20 carbon atoms.Root According to another embodiment, naphthenic base has 3 to 6 carbon atoms.Its specific example includes cyclopropyl, cyclobutyl, cyclopenta, 3- Methylcyclopentyl, 2,3- dimethylcyclopentyl, cyclohexyl, 3- methylcyclohexyl, 4- methylcyclohexyl, 2,3- dimethyleyelohexane Base, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyl, suberyl, cyclooctyl etc., but not limited to this.

In the present specification, alkoxy can be straight chain, branching or cricoid.The carbon atom number of alkoxy does not limit especially System, it is preferred that being 1 to 30.Its specific example include methoxyl group, ethyoxyl, positive propoxy, isopropoxy (isopropoxy), Isopropoxy (i-propyloxy), n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyl oxygen, Isoamoxy, positive hexyloxy, 3,3- dimethyl butyrate oxygroup, 2- ethyl-butoxy, n-octyloxy, positive nonyl epoxide, n-decyloxy, benzyl Oxygroup, to methylbenzyloxy etc., but not limited to this.

In the present specification, amido can be selected from-NH₂, monoalkyl amido, dialkyl amino, N- alkylaryl amido, list Arylamine group, diaryl amido, N- aryl heteroaryl amido, N- miscellaneous alkyl aryl amido, single heteroaryl amido and two heteroaryls Amido, and its carbon atom number is not particularly limited, it is preferred that being 1 to 30.The specific example of amido includes methylamino, two Methylamino, ethyl amido, diethyl amido, phenyl amido, naphthalene amido, xenyl amido, anthryl amido, 9- methyl-anthracene Base amido, diphenyl amido, xylyl amido, N- xenyl naphthalene amido, N- phenyltoluene base amido, N- xenyl naphthalene Amido, N- phenyltoluene base amido, triphenyl amido, N- naphthalene fluorenyl amido, N- phenyl phenanthryl amido, N- xenyl phenanthryl amine Base, N- phenylfluorenyl amido, N- phenyl triphenyl amido, N- phenanthryl fluorenyl amido, N- xenyl fluorenyl amido etc., but be not limited to This.

In the present specification, N- alkylaryl amido means the amido that the N of wherein amido replaces through alkyl and aryl.

In the present specification, N- aryl heteroaryl amido means the amido that the N of wherein amido replaces through aryl and heteroaryl.

In the present specification, N- miscellaneous alkyl aryl amido means what the N of wherein amido replaced through alkyl and heteroaryl amido Amido.

In the present specification, monoalkyl amido, dialkyl amino, N- aryl alkyl amido, alkyl sulfenyl, alkyl sulphonyl It is identical as the example of abovementioned alkyl with the alkyl in N- miscellaneous alkyl aryl amido.Specifically, the example of alkyl sulfenyl includes methyl Sulfenyl, ethylsulfanyl, tert. butyl-sulphenyl, hexyl sulfenyl, octylthio etc., and the example of alkyl sulphonyl includes sulfonyloxy methyl Base, ethylsulfonyl, sulfonyl propyl base, butyl sulfonyl etc., but the example is without being limited thereto.

In the present specification, alkenyl can be straight chain or branching, and its carbon atom number is not particularly limited, but excellent It is selected as 2 to 40.According to an embodiment, alkenyl has 2 to 20 carbon atoms.According to another embodiment, alkenyl has 2 To 10 carbon atoms.According to another embodiment, alkenyl has 2 to 6 carbon atoms.Its specific example includes vinyl, 1- Acrylic, isopropenyl, 1- cyclobutenyl, 2- cyclobutenyl, 3- cyclobutenyl, 1- pentenyl, 2- pentenyl, 3- pentenyl, 3- methyl- 1- cyclobutenyl, 1,3- butadienyl, allyl, 1- phenyl vinyl -1- base, 2- phenyl vinyl -1- base, 2,2- diphenyl second Alkenyl -1- base, 2- phenyl -2- (naphthalene -1- base) vinyl -1- base, 2,2- bis- (diphenyl -1- base) vinyl -1- bases, Stilbene Base, styryl etc., but not limited to this.

In the present specification, silicyl specifically includes trimethyl silyl, triethylsilyl, tert-butyl two Methyl silicane base, vinyldimethylsilyl, propyl-dimethyl silicyl, triphenyl-silyl, diphenylmethyl Silylation, phenyl silyl groups etc., but not limited to this.

In the present specification, boryl specifically includes trimethyl boryl, triethyl group boryl, fert-butyidimethylsilyl boryl, three Phenyl boryl, phenyl boryl etc., but not limited to this.

In the present specification, the specific example for aoxidizing phosphino- includes diphenyl phosphine oxide base, dinaphthyl oxidation phosphino- etc., but It is without being limited thereto.

In the present specification, aryl is not particularly limited, it is preferred that having 6 to 60 carbon atoms, and can be single Cyclophane base or polyaromatic.According to an embodiment, aryl has 6 to 30 carbon atoms.According to an embodiment, aryl With 6 to 20 carbon atoms.As monocyclic aryl, aryl can be phenyl, xenyl, terphenyl etc. but not limited to this.It is more The example of cyclophane base include naphthalene, anthryl, phenanthryl, pyrenyl, base,Base, fluorenyl etc., but not limited to this.

In the present specification, fluorenyl can be substituted, and two substituent groups can connect to each other to form spiro Structure.In the substituted situation of fluorenyl, it can be formedDeng.However, structure is without being limited thereto.

In the present specification, " adjacent " group can be to be taken by the atom that the atom replaced with corresponding substituent group is directly connected to The substituent group in generation, the substituent group being spatially arranged closest to corresponding substituent group, or replace original replaced corresponding substituent group Another substituent group of son.For example, replacing two of same carbon in two substituent groups and aliphatic ring that replace on the ortho position of phenyl ring Substituent group can be construed to the group of " adjacent " each other.

In the present specification, monoarylamine base, diaryl amido, aryloxy group, artyl sulfo, aryl sulfonyl, N- aryl Aryl in alkyl amine group, N- aryl heteroaryl amido and aryl phosphino- is identical as the example of above-mentioned aryl.Specifically, aryloxy group Example include phenoxy group, to toloxyl, toloxyl, 3,5- Dimehtyl-phenoxy, 2,4,6- trimethylbenzene oxygroup, To tert-butyl benzene oxygroup, 3- biphenylyloxy, 4- biphenylyloxy, 1- naphthoxy, 2- naphthoxy, 4- methyl-1-naphthoxy, 5- first Base -2- naphthoxy, 1- anthracene oxygroup, 2- anthracene oxygroup, 9- anthracene oxygroup, 1- phenanthrene oxygroup, 3- phenanthrene oxygroup, 9- phenanthrene oxygroup etc., artyl sulfo Example include phenylsulfartyl, 2- aminomethyl phenyl sulfenyl, 4- tert-butyl-phenyl sulfenyl etc., and the example of aryl sulfonyl includes Benzenesulfonyl, p-toluenesulfonyl etc., but the example is without being limited thereto.

In the present specification, heterocycle is comprising at least one of O, N, Se and S as heteroatomic heterocycle, and Its carbon atom number is not particularly limited, it is preferred that being 2 to 60.The example of heterocycle include thienyl, furyl, pyrrole radicals, Imidazole radicals, thiazolyl,Oxazolyl,Di azoly, pyridyl group, bipyridyl, pyrimidine radicals, triazine radical, acridinyl, is rattled away at triazolyl Piperazine base, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido-pyrazine base, pyrazine are simultaneously Pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzo carbazole base, benzene It is bithiophene base, dibenzothiophene, benzofuranyl, phenanthroline, thiazolyl, differentOxazolyl,Di azoly, thiadiazolyl group, Benzothiazolyl, phenothiazinyl, dibenzofuran group etc., but not limited to this.

In the present specification, heteroaryl includes one or more atoms, that is, one or more miscellaneous originals in addition to carbon Son, and specifically, hetero atom may include one or more atoms in O, N, Se and S etc..Its carbon atom number does not have There is special limitation, it is preferred that being 2 to 60, and heteroaryl may be monocyclic or polycyclic.The example of heterocycle includes thiophene Pheno base, furyl, pyrrole radicals, imidazole radicals, thiazolyl,Oxazolyl,Di azoly, pyridyl group, bipyridyl, pyrimidine radicals, triazine Base, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, Pyrido-pyrazine base, pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzo It is thiazolyl, benzo carbazole base, benzothienyl, dibenzothiophene, benzofuranyl, phenanthroline, thiazolyl, differentAzoles Base,Di azoly, thiadiazolyl group, benzothiazolyl, phenothiazinyl, '-aziridino, azaindolyl, isoindolyl, indazole Base, purine radicals, pteridyl, B-carboline base, naphthyridines base, terpyridyl base, phenazinyl, imidazopyridyl, burnt pyridine (pyropyridyl), azepines base, pyrazolyl, dibenzofuran group etc., but not limited to this.

In the present specification, single heteroaryl amido, di (hetero) arylamine group, N- aryl heteroaryl amido and N- miscellaneous alkyl aryl The example that the example of heteroaryl in amido can be selected from above-mentioned heteroaryl.

In the present specification, alkylidene be the divalent functional groups derived from alkane, and the example include straight chain, branching or Cyclic group, such as methylene, ethylidene, propylidene, isobutylidene, sub- sec-butyl, sub- tert-butyl, pentylidene, hexylidene etc..

In the present specification, halogeno alkylen means the functional group that wherein above-mentioned alkylidene replaces through halogen group, such as Perfluoropropane -2,2- diyl etc..

In the present specification, arlydene means that there are two bonding positions, i.e. bivalent group in aryl.It can be using virtue The foregoing description of base, the difference is that arlydene is respectively bivalent group.

In the present specification, it is being bonded to each other in the ring for being substituted or being unsubstituted formed by adjacent group, " ring " meaning Refer to the hydrocarbon ring for being substituted or being unsubstituted or the heterocycle for being substituted or being unsubstituted.

In the present specification, hydrocarbon ring can be the condensed ring of aromatic ring, aliphatic ring or aromatic ring and aliphatic ring, and can be with Example selected from the naphthenic base or aryl, the difference is that hydrocarbon ring is not monovalence.

In the present specification, aromatic ring can be monocycle or polycyclic, and can be different selected from the example of the aryl Place is that aromatic ring is not monovalence.

In the present specification, heterocycle includes one or more atoms, that is, one or more hetero atoms in addition to carbon, And specifically, hetero atom may include one or more atoms in O, N, Se and S etc..Heterocycle can for monocycle or Polycyclic, it can be the condensed ring of aromatic ring, aliphatic ring or aromatic ring and aliphatic ring, and the reality of the heteroaryl can be selected from Example, the difference is that heterocycle is not monovalence.

In the present specification, " direct key " refers to connect with bonding line, wherein atom or atom is not present in corresponding position Group.

An embodiment according to the present invention can provide the compound indicated by following formula 1.

[chemical formula 1]

In chemical formula 1,

Y1 and Y2 are same or different to each other, and are each independently direct key or-CQ1Q2-；

A is direct key, ether, carbonyl, ester group, two ester groups, peroxy, amino, imino group, imide, azo group, acyl Amido, the alkylidene with 1 to 10 carbon atom, the sub- miscellaneous alkyl with 1 to 10 carbon atom, has 1 to 10 carbon at sulfuryl The halogeno alkylen of atom, the arlydene with 6 to 20 carbon atoms or the inferior heteroaryl with 3 to 20 carbon atoms,

R1 is same or different to each other to R26, Q1 and Q2, and is each independently hydrogen, deuterium, halogen group, itrile group, nitre Base, hydroxyl, carbonyl, ester group, imide, amide groups, carboxyl (- COOH) ,-OC (=O) R " ', sulfonic group (- SO₃H), sulfanilamide (SN) Base, the alkyl for being substituted or being unsubstituted, the naphthenic base for being substituted or being unsubstituted, the alkoxy for being substituted or being unsubstituted, The aryloxy group that is substituted or is unsubstituted, the alkyl sulfenyl for being substituted or being unsubstituted, the aryl sulphur for being substituted or being unsubstituted Base, the aryl sulfonyl for being substituted or being unsubstituted, is substituted or is unsubstituted the alkyl sulphonyl for being substituted or being unsubstituted Alkenyl, the silicyl, the boryl for being substituted or being unsubstituted, the amine that is substituted or is unsubstituted that are substituted or are unsubstituted Base, the aryl phosphino- for being substituted or being unsubstituted are substituted or be unsubstituted oxidation phosphino-, the virtue that is substituted or is unsubstituted Base or the heteroaryl for being substituted or being unsubstituted or adjacent group can be connected to each other to form and be substituted or without taking The ring in generation, and

R " ' is the alkyl for being substituted or being unsubstituted.

The present inventor is found through experiments that, due to by the inclusion of the sulphonic acid ester in molecular structure as described in chemical formula 1 Base and increase compound solubility in a solvent, therefore the shape of compound to reassociate and inhibit foreign matter can be prevented At, and excitation purity, brightness and contrast therefore can be improved when being applied to colour filter, thereby completing the present invention.

Particularly, in the compound of an embodiment, two are introduced into molecular structure due to forming dimer Sulfonic group so that by sulfonate group improve solubility effect it is available further enhance, be furthermore appropriately combined from light The absorption spectrum and transmitted spectrum of spectrum and colour filter that source issues, so that excitation purity increases and color can be improved again Existing, brightness and contrast.Further, since molecular weight increase and improve heat resistance, even and if when manufacturing light-sensitive material The mutation of excitation purity, brightness and contrast does not occur yet after heat treatment step, to realize stable display performance.

Further, since the compound of an embodiment uses the aromatic functional group for being bonded to the end of sulfonate group, Such as the aryl with 6 to 20 carbon atoms or the heteroaryl with 3 to 20 carbon atoms, therefore may be implemented to improve heat resistance Effect.

Specifically, in chemical formula 1, Y1 and Y2 are same or different to each other, and independently are direct key or-CQ1Q2-. In-CQ1Q2-, C is carbon, and Q1 and Q2 can indicate the functional group for being bonded to carbon each independently.Therefore, as Y1 or Y2 When for direct key, the pentagon ring with 5 carbon atoms can be formed, and when Y1 or Y2 is-CQ1Q2-, can be formed has The hexagonal rings of 6 carbon atoms.

In addition, in chemical formula 1, A be direct key, ether, carbonyl, ester group, two ester groups, peroxy, amino, imino group, Imide, azo group, amide groups, sulfuryl, the alkylidene with 1 to 10 carbon atom, the Asia with 1 to 10 carbon atom are miscellaneous Alkyl, the halogeno alkylen with 1 to 10 carbon atom, the arlydene with 6 to 20 carbon atoms have 3 to 20 carbon The inferior heteroaryl of atom.

It is highly preferred that A can be direct key, ether, carbonyl, two ester groups, sulfuryl, have 1 to 10 in chemical formula 1 The alkylidene of carbon atom or halogeno alkylen with 1 to 10 carbon atom.

Two ester groups are the functional group comprising Liang Ge ester functional group, and the example includes the official indicated by following formula 2 It can group.

[chemical formula 2]

In chemical formula 2, X be the alkylidene with 1 to 10 carbon atom, the sub- miscellaneous alkyl with 1 to 10 carbon atom, Halogeno alkylen with 1 to 10 carbon atom, the arlydene with 6 to 20 carbon atoms or with 3 to 20 carbon atoms Inferior heteroaryl.Preferably, X can be alkylidene with 1 to 5 carbon atom, such as methylene, ethylidene, propylidene etc..

Halogeno alkylen with 1 to 10 carbon atom means that wherein the alkylidene with 1 to 10 carbon atom is through halogen The functional group that group replaces, and the example includes perfluoropropane -2,2- diyl etc..

In chemical formula 1, R1 to R26 is same or different to each other, and is each independently hydrogen, halogen group, nitro, carboxylic Base, ester group, hydroxyl ,-OC (=O) R' ", sulfonic group (- SO₃H), the alkyl that is substituted or is unsubstituted is substituted or without taking The alkoxy in generation, the aryloxy group for being substituted or being unsubstituted or the aryl for being substituted or being unsubstituted or adjacent group can To connect to each other to form the ring for being substituted or being unsubstituted.

R ' " is the alkyl for being substituted or being unsubstituted.

R ' " is methyl.

In chemical formula 1, R1 to R26 is identical or different each other, and independently is hydrogen, fluorine, chlorine, bromine, iodine, nitro, carboxylic Base, alkyl ester group, naphthenic base ester group, aryl alkyl ester group, hydroxyl ,-OC (═ O) CH₃, sulfonic group (- SO₃H), methyl, tertiary fourth Base, methoxyl group, phenyl or naphthyl.

In chemical formula 1, at least one of Q1, Q2 and R17 to R26 can be in conjunction with adjacent functionalities to be formed through taking Generation or the aromatic ring being unsubstituted.

Specifically, in chemical formula 1, at least one of Q1, Q2 and R17 to R26 are in conjunction with adjacent functionality to be formed The phenyl ring for being substituted or being unsubstituted or the naphthalene nucleus for being substituted or being unsubstituted.

In chemical formula 1, Y1 and Y2 can be each independently direct key.

The compound of one embodiment can be indicated by following formula 1-1.

[chemical formula 1-1]

In chemical formula 1-1,

A is direct key, ether, carbonyl, two ester groups, sulfuryl, the alkylidene with 1 to 10 carbon atom or has 1 to 10 The halogeno alkylen and R27 and R28 of a carbon atom are same or different to each other, and are each independently phenyl or naphthyl.

In addition, the compound of an embodiment can be indicated by following formula 1-2 or 1-3.

[chemical formula 1-2]

[chemical formula 1-3]

In chemical formula 1-2 or 1-3, A is direct key, ether, carbonyl, two ester groups, sulfuryl, has 1 to 10 carbon atom Alkylidene or halogeno alkylen with 1 to 10 carbon atom and R28 to R31 be same or different to each other, and respectively It independently is phenyl or naphthyl.

The compound of one embodiment can be indicated by any one of following formula 1-4 to 1-15.

[chemical formula 1-4]

[chemical formula 1-5]

[chemical formula 1-6]

[chemical formula 1-7]

[chemical formula 1-8]

[chemical formula 1-9]

[chemical formula 1-10]

[chemical formula 1-11]

[chemical formula 1-12]

[chemical formula 1-13]

[chemical formula 1-14]

[chemical formula 1-15]

Meanwhile another embodiment according to the present invention, the compound comprising said one embodiment can be provided Color material composition.

The details of the above compound include above with respect to described in an embodiment those.

Color material composition can also include at least one of dyestuff and pigment.For example, above-mentioned color material combination Object can only include the compound of said one embodiment, but its compound and one kind for may include an embodiment Or more dyestuff, perhaps may include the compound of an embodiment and one or more of pigment or may include The compound of one embodiment and one or more of dyestuffs and one or more of pigment.

The specific type of dyestuff or pigment used herein is not particularly limited, and can be without limitation using extensive For colour filter or a variety of materials of field of display.

Meanwhile another embodiment according to the present invention, the compound comprising said one embodiment can be provided Or the color material compositions of other above-mentioned embodiments, adhesive resin, polyfunctional monomer, photoinitiator and solvent it is photosensitive Resin combination.

The details of the above compound include above with respect to described in an embodiment those, and color material combine The details of object include above with respect to described in other embodiments those.

Adhesive resin is not particularly limited, as long as its physics that can show the film manufactured by the resin combination is special Property such as intensity and can developability.

Adhesive resin can be the polyfunctional monomer of imparting mechanical strength and the copolymer resin of the alkali-soluble monomer of imparting Rouge, and can also include adhesive commonly used in the art.

The polyfunctional monomer for assigning the mechanical strength of film can be esters of unsaturated carboxylic acids, aromatic vinyl, unsaturated ethers, no At least one of unsaturated imide and acid anhydrides.

The specific example of esters of unsaturated carboxylic acids can be selected from (methyl) benzyl acrylate, (methyl) methyl acrylate, (first Base) ethyl acrylate, (methyl) butyl acrylate, (methyl) acrylate, (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) cyclohexyl acrylate, (methyl) isobornyl acrylate, (methyl) acrylic acid ethyl oneself Ester, (methyl) acrylic acid 2- phenoxy ethyl, (methyl) tetrahydrofurfuryl acrylate, (methyl) Hydroxyethyl Acrylate, (methyl) Acrylic acid 2- hydroxy propyl ester, (methyl) acrylic acid 2- hydroxyl -3- chlorine propyl ester, (methyl) acrylic acid 4- hydroxybutyl, (methyl) third Olefin(e) acid acyl group octyloxy -2- hydroxy propyl ester, (methyl) glycerol acrylate, (methyl) acrylic acid 2- methoxy acrylate, (methyl) Acrylic acid 3- methoxybutyl, (methyl) ethioxy binaryglycol ester, (methyl) methoxyethyl triglycol ester, (methyl) methoxyethyl tripropylene glycol ester, poly(ethylene glycol) methyl ether (methyl) acrylate, (methyl) acrylic acid benzene oxygen Ethyl glycol ester, (methyl) acrylic acid poly- to Nonylphenoxy to Nonylphenoxy macrogol ester, (methyl) acrylic acid the third two Alcohol ester, (methyl) glycidyl acrylate, (methyl) acrylic acid tetrafluoro propyl ester, (methyl) acrylic acid 1,1,1,3,3,3- hexafluoro Isopropyl ester, (methyl) acrylic acid octafluoro pentyl ester, 17 fluorine last of the ten Heavenly stems ester of (methyl) acrylic acid, (methyl) tribromophenyl acrylate, propylene Acid methyl Alpha-hydroxy methyl esters, acrylic acid ethyl Alpha-hydroxy methyl esters, acrylic acid propyl Alpha-hydroxy methyl esters and propylene acid butyl Alpha-hydroxy Methyl esters, but not limited to this.

The specific example of aromatic vinyl monomer can be selected from styrene, α-methylstyrene, (o-, m-, to)-vinyl Toluene, (o-, m-, to)-methoxy styrene and (o-, m-, to)-chlorostyrene, but not limited to this.

The specific example of unsaturated ethers can be selected from methoxy ethylene, vinyl ethyl ether and allyl glycidyl ether, but It is without being limited thereto.

Unsaturated imido specific example can be selected from N-phenylmaleimide, N- (4- chlorphenyl) maleimide Amine, N- (4- hydroxy phenyl) maleimide and N- N-cyclohexylmaleimide, but not limited to this.

The example of acid anhydrides includes maleic anhydride, methyl maleic anhydride and tetrabydrophthalic anhydride, but not limited to this.

It assigns alkali-soluble monomer to be not particularly limited, as long as it includes acid groups, and for example it is preferable to use choosings From it is below at least one: (methyl) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5- drop ice Piece alkene -2- carboxylic acid, mono- 2- ((methyl) acryloxy) ethyl phthalate/salt, mono- 2- ((methyl) acryloyl-oxy Base) ethyl succinate/salt and ω-carboxy-polycaprolactone list (methyl) acrylate/salt, but not limited to this.

An embodiment according to the present invention, the acid value of adhesive resin are 50KOH mg/g to 130KOH mg/g, and And weight average molecular weight is 1000 to 50000.

Polyfunctional monomer is to have the function of forming the monomer of photoresist image by light, and its specific example Mixture including one selected from the following or both or more person: metering system acid propylene glycol ester, two season penta of six acrylic acid Four alcohol esters, acrylic acid dipentaerythritol ester, diacrylic acid pentyl diol ester, diacrylate 6- hexylene glycol ester, acrylic acid 1,6- oneself The double phenoxetol esters of diol ester, methacrylic acid tetraethylene glycol ester, diacrylate, trihydroxy ethyl isocyanurate trimethyl Acrylate, trimethyl propane trimethyl acrylic ester, six acrylic acid diphenyl pentaerythritols, trimethacrylate acid Ji Wusi Alcohol ester, pentaerythritol tetramethacrylate and hexamethyl acrylic acid dipentaerythritol ester.

Photoinitiator is not particularly limited, as long as it is to be generated free radicals in exposure to cause the initiator of crosslinking i.e. It can.For example, photoinitiator can for it is selected from the following at least one: acetophenone compounds, non-imidazole class compound, triazines Compound and oxime compound.

Acetophenone compounds can for it is selected from the following at least one: 2- hydroxy-2-methyl -1- phenyl-propane -1- ketone, 1- (4- isopropyl phenyl) -2- hydroxy-2-methyl propane -1- ketone, 4- (2- hydroxyl-oxethyl)-phenyl (2- hydroxyl -2- propyl) Ketone, 1- hydroxycyclohexylphenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2- dimethoxy -2- phenyl acetophenone, 2- methyl-(4- methyl mercapto) phenyl -2- morpholine -1- propane -1- ketone, 2- benzyl -2- Dimethylamino -1- (4- morpholinyl phenyl)-butane -1- ketone, the 2- (bromo- benzyl -2- dimethylamino -1- of 4- (4- morpholinyl phenyl) - Butane-1- ketone, 2- methyl-1-[4- (methyl mercapto) phenyl]-2- morpholine propane-1- ketone etc., but not limited to this.

Non-imidazole class compound can for it is selected from the following at least one: 2,2 '-bis- (2- chlorphenyls) -4,4 ', 5,5 '-four Phenyl is non-imidazole, it is 2,2 '-bis- (Chloro-O-Phenyls) -4,4 ', 5,5 '-four (3,4,5- trimethoxyphenyl) -1,2 '-non-imidazole, 2, 2 '-bis- (2,3- dichlorophenyl) -4,4 ', 5,5 '-tetraphenyls are non-imidazole, 2,2 '-bis- (Chloro-O-Phenyls) -4,4 ', 5,5 '-four benzene Base -1,2 '-is non-imidazole etc., but not limited to this.

Compound in triazine class can for it is selected from the following at least one: 3- { 4- [bis- (the trichloromethyl)-s- triazine -6- of 2,4- Base] phenylsulfartyl } propionic acid, 1,1,1,3,3,3- hexafluoro isopropyl -3- { 4- [bis- (the trichloromethyl)-s- triazine -6- bases of 2,4-] benzene Base sulfenyl } propionic ester/salt, ethyl -2- { 4- [bis- (the trichloromethyl)-s- triazine -6- bases of 2,4-] phenylsulfartyl } acetic acid esters/salt, 2- epoxy group ethyl -2- { 4- [bis- (the trichloromethyl)-s- triazine -6- bases of 2,4-] phenylsulfartyl } acetic acid esters/salt, cyclohexyl 2- { 4- [bis- (the trichloromethyl)-s- triazine -6- bases of 2,4-] phenylsulfartyl } acetic acid esters/salt, benzyl -2- { 4- [bis- (three chloromethanes of 2,4- Base)-s- triazine -6- base] phenylsulfartyl } acetic acid esters/salt, 3- (chloro- 4- [bis- (the trichloromethyl)-s- triazine -6- bases of 2,4-] phenyl Sulfenyl } propionic acid, 3- { 4- [bis- (the trichloromethyl)-s- triazine -6- bases of 2,4-] phenylsulfartyl } propionamide, bis- (three chloromethanes of 2,4- Base) -6- is to methoxyl-styrene-s- triazine, bis- (the trichloromethyl) -6- (1- is to dimethylaminophenyl) -1,3 of 2,4-,-fourth Dialkylene-s- triazine, 2- trichloromethyl -4- amino -6- to methoxyl-styrene-s- triazine etc., but not limited to this.

Oxime compound can for it is selected from the following at least one: 1,2- octadione- 1- (4- phenylsulfartyl) phenyl -2- (o-benzoyl base oxime) (CGI 124, manufactured by Ciba-Geigy), ethyl ketone -1- (9- ethyl) -6- (2- methyl benzoyl -3- Base) -1- (O- acetyl group oxime) (CGI 242, manufactured by Ciba-Geigy) and N-1919 (being manufactured by Adeka Corp.), but not It is limited to this.

Solvent can for it is selected from the following at least one: acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), methyl cellosolve, Ethyl cellosolve, tetrahydrofuran, 1,4- bis-Alkane, glycol dimethyl ether, ethylene glycol diethyl ether, Propylene Glycol Dimethyl Ether, propylene glycol Diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2- bis- Chloroethanes, 1,1,1- trichloroethanes, 1,1,2- trichloroethanes, 1,1,2- trichloro ethylene, hexane, heptane, octane, hexamethylene, benzene, Toluene, dimethylbenzene, methanol, ethyl alcohol, isopropanol, propyl alcohol, butanol, the tert-butyl alcohol, 2- ethyoxyl propyl alcohol, 2- methoxypropanol, 3- first Oxygroup butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene-glycol ethyl ether acetic acid esters, 3- methoxybutyl acetic acid esters, Ethyl -3- ethoxy-c acid esters, ethyl cellosolve acetate, methylcellosolve acetate, butyl acetate, propylene glycol monomethyl ether and Dipropylene glycol monomethyl ether, but not limited to this.

Based on the total weight of the Solid content in photosensitive resin composition, the content of compound can be 5 weight % to 60 weights Measure %.In addition, the content of adhesive resin can be 1 weight % to 60 weight %, the content of photoinitiator be 0.1 weight % extremely The content of 20 weight % and polyfunctional monomer is 0.1 weight % to 50 weight %.

The total weight of Solid content means the sum of the total weight of component in resin combination in addition to the solvent.Based on solid The standard of the weight % of content and the solid content of every kind of component can be by conventionals method of analysis used in the art for example Liquid chromatography or gas chromatography measure.

In addition, photosensitive resin composition can also include antioxidant.Based on the Solid content in photosensitive resin composition Total weight, the content of antioxidant are 0.1 weight % to 20 weight %.

Antioxidant can for it is selected from the following at least one: it is antioxidant based on hindered phenol, amine-based anti-oxidant Agent, the antioxidant based on sulphur and the antioxidant based on phosphine, but not limited to this.

The specific example of antioxidant may include: the heat stabilizer based on phosphoric acid, such as phosphoric acid, trimethyl phosphate and phosphorus Triethylenetetraminehexaacetic acid ester；Main anti-oxidant based on hindered phenol, for example, 2,6-di-tert-butyl p-cresol, octadecyl -3- (hydroxyl -3 4-, 5- di-tert-butyl-phenyl) propionic ester, four bis- [methylene -3- (3,5- di-tert-butyl-hydroxy phenyl) propionic ester] methane, 1,3, 5- trimethyl -2,4,6- three (3,5- di-tert-butyl-4-hydroxyl benzyl) benzene, 3,5- di-tert-butyl-4-hydroxyl benzyl phosphine diethyl Ester, 2,2- sulfenyl bis- (4- methyl-6-tert-butylphenols), 2,6-g, 4,4 '-butylidene of t- butylphenol-bis- (3- methyl -6- fourth Base phenol), 4,4 '-sulfenyls bis- (3 methy 6 tert butyl phenols) and it is bis- [3,3- is bis--(4 '-hydroxyls -3 '-tert-butyl-phenyl) Butyric acid] glycol ester；Secondary antioxidant amine-based, such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N '-diphenyl is to Asia Phenylenediamine and N, N '-two-betanaphthyl P- pHENYLENE dI AMINE；Antioxidant is helped based on sulphur, such as dilauryl disulphide, Dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazoler and tetramethylthiuram disulfide four are bis- [sub- Methyl -3- (lauryl sulfenyl) propionic ester] methane；And antioxidant, such as triphenylphosphine, three (nonyl benzenes are helped based on phosphine Base) the double Asias of phosphine, three isodecyl phosphines, bis- (2,4- dibutylphenyl) pentaerythrite diphosphines and (1,1 '-xenyl) -4,4 '-diyls Phosphonic acids four [bis- (1,1- dimethyl ethyl) phenyl of 2,4-] ester.

In addition, photosensitive resin composition can also include one or more of additives selected from the following: photocrosslinking is quick Agent, curing accelerator, adhesion promotor, surfactant, thermal polymerization inhibitor, ultraviolet absorber, dispersing agent and levelling agent. Based on the total weight of the Solid content in photosensitive resin composition, the content of additive is 0.1 weight % to 20 weight %.

As photo-crosslinking sensitizer, can be used it is selected from the following at least one: the compound based on benzophenone, example Such as bis- (dimethylamino) benzophenone of benzophenone, 4,4-, bis- (diethylamino) benzophenone of 4,4-, 2,4,6- trimethyl Aminobenzophenone, methyl o-benzoyl yl benzoic acid ester, 3,3- dimethyl -4- methoxy benzophenone and 3,3,4,4- tetra- (t-butylperoxycarbonyl) benzophenone；Compound based on Fluorenone, such as the chloro- 9-Fluorenone of 9-Fluorenone, 2- and 2- methyl -9- Fluorenone；Compound based on thioxanthones, such as the chloro- 4- propoxyl group of thioxanthones, 2,4- diethyl thioxanthone, 2-chlorothioxanthone, 1- Thioxanthones, isopropyl thioxanthone and diisopropylthioxanthone；Based on the compound of ton ketone, such as ton ketone and 2- methyl ton ketone；Anthracene Naphtoquinone compounds, such as anthraquinone, 2-methylanthraquinone, 2- ethyl hydrazine, tert-butyl anthraquinone and 2, chloro- 9, the 10- anthraquinone of 6- bis-；Based on a word used for translation The compound of pyridine, such as bis- (9- acridinyl) heptane of 9- phenylacridine, 1,7-, 1,5- bis- (9- acridinyl pentanes) and 1,3- is bis- (9- acridinyl) propane；Dicarbonyl compound, such as benzyl, 1,7,7- trimethyl-bicyclos [2,2,1] heptane -2,3- diketone and 9,10- phenanthrenequione；Compound based on phosphine oxide, such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis- (2,6- bis- Methoxybenzoyl base) -2,4,4- trimethylpentylphosphine oxide；Compound based on benzoic ether, such as methyl -4- (diformazan Base amino) benzoic ether, ethyl -4- (dimethylamino) benzoic ether and 2- n-butoxyethyl -4- (dimethylamino) benzene Formic acid esters；Amine synergist, such as 2, bis- (the 4- diethylamino benzal) cyclopentanone of 5-, 2,6- are bis-, and (4- diethylamino is sub- Benzyl) cyclohexanone and bis- (4- diethylamino the benzal) -4- methyl-cyclopentanones of 2,6-；Compound based on cumarin, such as 3,3- carbonyl ethenyl -7- (diethylamino) cumarin, 3- (2-[4-morpholinodithio base) -7- (diethylamino) cumarin, 3- Benzoyl -7- (diethylamino) cumarin, 3- benzoyl -7- methoxyl group-cumarin and 10,10- carbonyl it is bis- [1,1,7, 7- tetramethyl -2,3,6,7- tetrahydro -1H, 5H, 11H-C1]-benzopyrone [6,7,8-ij]-quinolizine -11- ketone；Chalcone Close object, such as 4- diethylamino chalcone and 4- triazobenzene formaldehyde acetophenone, 2- benzoyl methylene and 3- methyl-b- Naphthothiazoles.

Curing accelerator for enhance solidification and mechanical strength, and can be used it is selected from the following at least one: 2- mercapto Base benzimidazole, 2-mercaptobenzothiazole, 2- sulfydryl benzoAzoles, 2,5- dimercapto -1,3,4- thiadiazoles, 2- sulfydryl -4,6- Dimethyl aminopyridine, pentaerythrite-four (3-thiopropionate), pentaerythrite-three (3-thiopropionate), pentaerythrite- Four (2- mercaptoacetates), pentaerythrite-three (2- mercaptoacetate), trimethylolpropane-three (2- mercaptoacetate) and three Hydroxymethyl-propane-three (3-thiopropionate).

As for adhesion promotor of the invention, can be used it is selected from the following at least one: methylacryloyl silicon Alkane coupling agent, such as methacryloxypropyl trimethoxy silane, methacryloxypropyl dimethoxysilane, first Base acryloxypropyl triethoxysilane and methacryloxypropyl dimethoxysilane, and as alkyl front three Oxysilane, can be used it is selected from the following at least one: octyl trimethoxy silane, dodecyltrimethoxysilane and ten Eight alkyl trimethoxysilanes.

Surfactant includes the surfactant based on silicon and the surfactant based on fluorine.Specifically, based on silicon Surfactant includes BYK-077, BYK-085, BYK-300, BYK-301, the BYK- that can be obtained by BYK-Chemie GmbH 302、BYK-306、BYK-307、BYK-310、BYK-320、BYK-322、BYK-323、BYK-325、BYK-330、BYK-331、 BYK-333、BYK-335、BYK-341v344、BYK-345v346、BYK-348、BYK-354、BYK-355、BYK-356、BYK- 358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390 etc., and the surfactant packet based on fluorine Include can by DIC (Dai Nippon Ink&Chemicals) obtain F-114, F-177, F-410, F-411, F-450, F-493, F-494、F-443、F-444、F-445、F-446、F-470、F-471、F-472SF、F-474、F-475、F-477、F-478、F- 479、F-480SF、F-482、F-483、F-484、F-486、F-487、F-172D、MCF-350SF、TF-1025SF、TF- 1117SF、TF-1026SF、TF-1128、TF-1127、TF-1129、TF-1126、TF-1130、TF-1116SF、TF-1131、 TF1132, TF1027SF, TF-1441, TF-1442 etc., but not limited to this.

As ultraviolet absorber, can be used 2- (3- tert-butyl -5- methyl -2- hydroxy phenyl) chloro- benzotriazole of -5-, Alkoxy benzophenone etc., but not limited to this, and can without limitation using it is usually used in this field those.

The example of thermal polymerization inhibitor may include it is selected from the following at least one: to methyl phenyl ethers anisole, hydroquinone, burnt catechu Phenol (pyrocatechol), tert-butyl catechol (t-butyl catechol), N- nitroso phenylhydroxylamine base ammonium salt, N- are sub- Nitrobenzophenone hydroxyl amido aluminium salt, p methoxy phenol, di-tert-butyl p-cresol, pyrogallol, benzoquinones, the bis- (3- of 4,4- sulfenyl Methyl-6-tert-butylphenol), 2,2- di-2-ethylhexylphosphine oxide (4- methyl-6-tert-butylphenol), 2- mercaptoimidazole and phenthazine, but not Be limited to this, and can without limitation using it is usually used in this field those.

Dispersing agent can by dispersing agent in the form of pigment is surface-treated in advance inside be added in pigment Method uses the method being added in pigment outside dispersing agent.As dispersing agent, non-ionic dispersing agent, yin can be used The type of compounds of ionic dispersants or cation dispersing agent, and the example include it is based on fluorine, based on ester, cationic, Anion, nonionic and amphoteric surfactant.These can be used alone or being applied in combination with two or more.

Specifically, dispersing agent can for it is selected from the following at least one: poly- alkyl diol and its ester, polyoxyalkyl Quito First alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, ester group sulphonic acid ester/salt, sulfonate, carboxylate, carboxylic Hydrochlorate, alkylamide alkylene oxide adduct and alkylamine, but not limited to this.

Levelling agent can be polymerization or non-polymeric.The specific example of the levelling agent of polymerization includes polyethyleneimine, gathers Amide amine and amine-epoxy compound reaction product, the specific example of non-polymeric levelling agent include sulfur-bearing nonpolymer compound and Nitrogenous nonpolymer compound, but not limited to this, and can without limitation using it is usually used in this field those.

Photosensitive resin composition can be used for manufacturing the pigment of Thin Film Transistor-LCD (TFT LCD) colour filter Distributed light-sensitive material；It is used to form the black matrix of thin film transistor-liquid crystal display (LCD-TFT) or Organic Light Emitting Diode Light-sensitive material；It is used to form the light-sensitive material of coating；Column spacer light-sensitive material；For photocurable coating applications, Photocurable ink, Photocurable adhesive, printing plate and printed circuit board light-sensitive material；For plasma scope face The light-sensitive material of plate (PDP)；Etc., but its purpose is not particularly limited.

Meanwhile another embodiment according to the present invention, the photosensitive tree by using other embodiments can be provided The light-sensitive material of oil/fat composition manufacture.

The details of photosensitive resin composition include above with respect to described in other embodiments those.

Specifically, the light-sensitive material of film or pattern form can be by coating the photosensitive resin composition of embodiment It is formed on the substrate.Coating method is not particularly limited, but spray-on process, rolling method, spin-coating method can be used etc., and usually Spin-coating method is widely used.In addition, after forming coating film, if it is desired, it is molten that a part residual can be removed under reduced pressure Agent.

As for making the cured light source of photosensitive resin composition, such as it can be mentioned that launch wavelength is 250nm to 450nm The mercury vapour arc of light, carbon arc, Xe arc etc., but be not necessarily limited to this.

Meanwhile another embodiment according to the present invention, the colour filter of the light-sensitive material comprising embodiment can be provided Device.

The details of light-sensitive material include above with respect to described in other embodiments those.

Colour filter can be manufactured by using the photosensitive resin composition of the compound comprising an embodiment.Colour filter It can be by being formed as follows: photosensitive resin composition being coated in substrate to form coating film, then makes coating film exposed, aobvious Shadow and solidification.

Photosensitive resin composition excellent heat resistance and due to heat treatment and color change is smaller, therefore manufacture colour filter When even if the colour filter with high color reprodubility and high brightness and contrast can also be provided in the curing process.

Substrate can for glass plate, silicon wafer or plastic-substrates (such as polyether sulfone (PES), polycarbonate (PC)) etc., and And the kind thereof is not particularly limited.

Colour filter may include red pattern, green model, blue pattern and black matrix.

According to another embodiment, colour filter can also include coating.

Purpose in order to improve the contrast can arrange the grid of referred to as black matrix between the colored pixels of colour filter Shape black pattern.Chromium may be used as the material of black matrix.In which case it is possible to use by chromium deposition in entire substrate of glass The method for going up and pattern being formed by etching process.However, it is contemplated that the high reflectance of the high cost of technique, chromium and being given up by chromium The resin black matrix according to pigment dispersion method for being able to carry out micro manufacturing can be used in environmental pollution caused by liquid.

Black pigment or black dyes conduct can be used in the formation of the black matrix of an embodiment according to the present invention Color material.For example, can be used alone carbon black or the mixture of carbon black and coloured pigment can be used.In such case Under, due to being added to the coloured pigment with dim light shielding character, will not make the amount relative increase of color material Film strength reduces the adhesiveness of substrate.

Meanwhile another embodiment according to the present invention, the aobvious of the colour filter including embodiments above can be provided Showing device.

The details of colour filter include above with respect to described in other embodiments those.

Display device can be plasm display panel (PDP), light emitting diode (LED) display, organic light emission Diode (OLED) display, liquid crystal display (LCD), thin film transistor-liquid crystal display (TFT-LCD) and cathode-ray tube Any one of (CRT).

Beneficial effect

According to the present invention it is possible to provide the compound with excellent color characteristics, heat resistance and solvent resistance；Use it Photosensitive resin composition；And light-sensitive material, colour filter and the display device manufactured by using it.

Specific embodiment

It will be described in still more detail by the following examples embodiment of the present invention now.However, providing these embodiments It is only used for illustrating purpose, it is no intended to limit the scope of the disclosure.

Preparation example 1

Pass through the reaction synthesis compound A-1 as shown in following reaction scheme 1.

[reaction scheme 1]

25g (157.041mmol, 1 equivalent) compound 1 is added to 200g methylene chloride (MC, manufacturer: DAEJUNG) And it stirs.Ice bath is provided and reaction solution is made to reach 0 DEG C.19.07g is slowly added drop wise into reaction solution (188.454mmol, 1.2 equivalents) triethylamine (TEA).

Then, 30.787g (174.321mmol, 1.11 equivalents) compound 2 is slowly added drop wise into reaction solution. It reacts mixture 30 minutes at 0 DEG C, is then stirred at room temperature 24 hours.300g distilled water is added into reaction solution It (DI water) and stirs 30 minutes, and separates organic layer and water layer.200ml MC is added into isolated water layer and is further extracted. The K of 200ml 5% is added into organic layer₂CO₃Then solution & stir separates organic layer.It extracts repeatedly, until to organic layer Middle addition distilled water and solution are to neutralize.Make organic layer be subjected to depressurizing and removes solvent.Sediment is added to 500ml ratio The ethyl acetate (EA) that example is 1: 3: the solution & stir of n-hexane, and filter under reduced pressure.Sediment is dry at 80 DEG C One day to obtain 45.736g (152.79mmol) compound A-1 (yield: 97%) as white solid.

1H NMR(500MHz.CDCl₃): 8.00~7.97 (t, 3H), 7.70~7.68 (d, 1H), 7.66~7.65 (d, 1H), 7.59~7.55 (t, 1H), 7.47~7.42 (q.3H), 7.21~7.20 (d, 1H), 2.51 (s, 3H)

Preparation example 2

Compound A-2 is synthesized in a manner of identical with preparation example 1, the difference is that using 39.339g (174.321mmol, 1.11 equivalents) compound 3 replaces compound 2, as shown in following reaction scheme 2.

[reaction scheme 2]

Embodiment 1

(1) preparation of compound

Pass through the reaction synthesis compound C-1 as shown in following reaction scheme 3.

[reaction scheme 3]

In two neck round-bottom flasks add 1g (3.399mmol) A-1,0.518g (1.670mmol) B-1,1g benzoic acid and 10ml methyl benzoate simultaneously stirs 5 hours at 180 DEG C.Then, 100ml methanol is added, and the substance of precipitating is being depressurized Lower filtering, is then dried in an oven.To obtain 1.05g (1.2024mmol) compound C-1 (yield: 72%).

The result of the MS measurement of compound C-1 is as follows.

Ionization mode=: APCI+:m/z=873 [M+H]+, accurate mass: 872

(2) preparation of photosensitive resin composition

Compound C-1,10.376g adhesive resin [benzyl methacrylate and the methyl-prop that 5.554g or more is synthesized (molar ratio 70:30, acid value are 113KOH mg/g to the copolymer of olefin(e) acid, and the weight average molecular weight by gpc measurement is 20000g/ Mol, molecular weight distribution (PDI) are 2.0, and solid content (S.C) is 25%, and includes solvent (PGMEA)], 2.018g light draws Send out agent (I-369, BASF), 1.016g additive (F-475, DIC Corp.), 12.443g photopolymerizable compound (six acrylic acid Dipentaerythritol ester (DPHA) is manufactured by Nippon Kayaku Co., Ltd.) and 68.593g solvent (propylene glycol monomethyl ether second Acid esters, PGMEA) it mixes to manufacture photosensitive resin composition.

(3) preparation of light-sensitive material

Photosensitive resin composition is spin-coated on glass (5cm X 5cm), and at 100 DEG C prebake conditions 100 seconds to be formed Film.The distance between substrate with the membrane and photomask will be formed thereon and is set as 250 μm, and using exposure machine with 40mJ/cm² Exposure dose irradiation substrate front surface.Thereafter, make the development 60 in developing solution (KOH, 0.05%) of exposed substrate Second, and 20 minutes are toasted after carrying out at 230 DEG C to manufacture substrate.

Embodiment 2

(1) preparation of compound

0.9g (1.051mmol) compound C-2 is synthesized in the same manner as in example 1, the difference is that using 0.493g (1.590mmol) B-2 replaces compound the B-1, (yield: 66%) as shown in following reaction scheme 4.

The result of the MS measurement of compound C-2 is as follows.

Ionization mode=: APCI+:m/z=857 [M+H]+, accurate mass: 856

[reaction scheme 4]

(2) preparation of photosensitive resin composition and light-sensitive material

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-2 replaces compound C-1.

Embodiment 3

(1) preparation of compound

1.1g (1.284mmol) compound C-3 is synthesized in the same manner as in example 1, the difference is that using 0.493g (1.590mmol) B-3 replaces compound the B-1, (yield: 81%) as shown in following reaction scheme 5.

The result of the MS measurement of compound C-3 is as follows.

Ionization mode=: APCI+:m/z=857 [M+H]+, accurate mass: 856

[reaction scheme 5]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-3 replaces compound C-1.

Embodiment 4

(1) preparation of compound

1.26g (1.343mmol) compound C-4 is synthesized in the same manner as in example 1, the difference is that using 0.512g (1.590mmol) B-4 replaces compound the B-1, (yield: 85%) as shown in following reaction scheme 6.

The result of the MS measurement of compound C-4 is as follows.

Ionization mode=: APCI+:m/z=884 [M+H]+, accurate mass: 885

[reaction scheme 6]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-4 replaces compound C-1.

Embodiment 5

(1) preparation of compound

0.82g (0.843mmol) compound C-5 is synthesized in the same manner as in example 1, the difference is that using 0.652g (1.590mmol) B-5 replaces compound the B-1, (yield: 53%) as shown in following reaction scheme 7.

The result of the MS measurement of compound C-5 is as follows.

Ionization mode=: APCI+:m/z=949 [M+H]+, accurate mass: 948

[reaction scheme 7]

(2) manufacture of photosensitive resin composition and light-sensitive material

Photosensitive resin composition and light-sensitive material are manufactured in the same manner as in example 1, the difference is that using Compound C-5 replaces compound C-1.

Embodiment 6

(1) preparation of compound

1.3g (1.288mmol) compound C-6 is synthesized in the same manner as in example 1, the difference is that using 0.706g (1.590mmol) B-6 replaces compound the B-1, (yield: 81%) as shown in following reaction scheme 8.

The result of the MS measurement of compound C-6 is as follows.

Ionization mode=: APCI+:m/z=949 [M+H]+, accurate mass: 948

[reaction scheme 8]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-6 replaces compound C-1.

Embodiment 7

(1) preparation of compound

1g (1.030mmol) compound C-7 is synthesized in the same manner as in example 1, the difference is that using 1g (2.262mmol) A-2 replaces compound A-1, and uses 0.444g (1.431mmol) B-1, as shown in following reaction scheme 9 (yield: 71.9%).

The result of the MS measurement of compound C-7 is as follows.

Ionization mode=: APCI+:m/z=973 [M+H]+, accurate mass: 972

[reaction scheme 9]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-7 replaces compound C-1.

Embodiment 8

(1) preparation of compound

0.9g (0.941mmol) compound C-8 is synthesized in the same manner as in example 1, the difference is that using 1g (2.862mmol) A-2 replaces compound A-1, and uses 0.421g (1.431mmol) B-2, such as following 10 institute of reaction scheme Show (yield: 65.8%).

The result of the MS measurement of compound C-8 is as follows.

Ionization mode=: APCI+:m/z=957 [M+H]+, accurate mass: 956

[reaction scheme 10]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-8 replaces compound C-1.

Embodiment 9

(1) preparation of compound

0.9g (0.941mmol) compound C-9 is synthesized in the same manner as in example 1, the difference is that using 1g (2.862mmol) A-2 replaces compound A-1, and uses 0.421g (1.431mmol) B-3, such as following 11 institute of reaction scheme Show (yield: 65.8%).

The result of the MS measurement of compound C-9 is as follows.

Ionization mode=: APCI+:m/z=957 [M+H]+, accurate mass: 956

[reaction scheme 11]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-9 replaces compound C-1.

Embodiment 10

(1) preparation of compound

1g (1.015mmol) compound C-10 is synthesized in the same manner as in example 1, the difference is that using 1g (2.862mmol) A-2 replaces compound A-1, and uses 0.461g (1.431mmol) B-4, as shown in following reaction scheme 12 (yield: 71%).

The result of the MS measurement of compound C-10 is as follows.

Ionization mode=: APCI+:m/z=985 [M+H]+, accurate mass: 984

[reaction scheme 12]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-10 replaces compound C-1.

Embodiment 11

(1) preparation of compound

0.78g (0.730mmol) compound C-11 is synthesized in the same manner as in example 1, the difference is that making Compound A-1 is replaced with 1g (2.862mmol) A-2, and uses 0.586g (1.431mmol) B-5, such as following reaction scheme 13 Shown (yield: 51%).

The result of the MS measurement of compound C-11 is as follows.

Ionization mode=: APCI+:m/z=1073 [M+H]+, accurate mass: 1072

[reaction scheme 13]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-11 replaces compound C-1.

Embodiment 12

(1) preparation of compound

1.16g (1.045mmol) compound C-12 is synthesized in the same manner as in example 1, the difference is that making Compound A-1 is replaced with 1g (2.862mmol) A-2, and uses 0.636g (1.431mmol) B-6, such as following reaction scheme 14 Shown (yield: 73%).

The result of the MS measurement of compound C-12 is as follows.

Ionization mode=: APCI+:m/z=1107 [M+H]+, accurate mass: 1106

[reaction scheme 14]

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using Compound C-12 replaces compound C-1.

Comparative example 1

(1) preparation of compound

Use the PY138 pigment with following chemical structure.

Photosensitive resin composition and light-sensitive material are prepared in the same manner as in example 1, the difference is that using PY138 replaces compound C-1.

The physics of the photosensitive resin composition or light-sensitive material that obtain in embodiment and comparative example is measured by the following method Characteristic, and result is shown in the following table 1 to 3.

1. solvent resistance

The every kind of compound obtained in measurement embodiment and comparative example is in the dimethylformamide (DMF) as organic solvent In solubility, according to following criterion evaluation solvent resistance, and result is shown in table 1 below.

Zero: solubility is 1% or bigger

X: solubility is less than 1%

[table 1]

The result of experimental example 1

As shown in table 1, the compound of embodiment has the solubility improved in organic solvent compared with comparative example.Dissolution The raising of degree seems to come from that include SO in the compound of embodiment₃Functional group.

Therefore, from needed when being dissolved in organic solvent it is different by the general pigment of the dispersions such as derivative, dispersing agent, implement The compound of example does not need derivative or dispersing agent when being dissolved in organic solvent, therefore can easily for commercial applications.

2. the assessment of heat resistance

The substrate through prebake conditions obtained in embodiment is obtained by using spectroscope (MCPD-OTSUKA) to exist The transmitted spectrum of visible light region within the scope of 380nm to 780nm.

Then, 20 minutes will be toasted to obtain identical equipment and measurement after the substrate of prebake conditions is at 230 DEG C further The transmitted spectrum of range.

The meter of Eab is carried out by using the transmitted spectrum and the value E (L*, a*, b*) that obtains using illuminant-C backlight of acquisition It calculates, and result is shown in the following table 2.

Δ E (L*, a*, b*)={ (Δ L*)²+(Δa*)²+(Δb*)²}^1/2

Eab={ the Δ E (L*, a*, b*) after rear baking }-{ the Δ E (L*, a*, b*) after prebake conditions }

The value of Δ E is small to mean color excellent heat resistance.In the case where colour filter relevant material, when Δ Eab value is less than 3 When, it is considered as excellent material.

[table 2]

The result of experimental example 2

As shown in table 2, the light-sensitive material of embodiment has the small Eab value less than 3, this shows that it shows excellent color Heat resistance.

Claims

1. a kind of compound indicated by following formula 1:

[chemical formula 1]

Wherein, in chemical formula 1,

Y1 and Y2 are same or different to each other, and are each independently direct key or-CQ1Q2-,

A is direct key, ether, carbonyl, ester group, two ester groups, peroxy, amino, imino group, imide, azo group, amide Base, the alkylidene with 1 to 10 carbon atom, the sub- miscellaneous alkyl with 1 to 10 carbon atom, has 1 to 10 carbon original at sulfuryl The halogeno alkylen of son, the arlydene with 6 to 20 carbon atoms or the inferior heteroaryl with 3 to 20 carbon atoms,

R1 is same or different to each other to R26, Q1 and Q2, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl Base, carbonyl, ester group, imide, amide groups, carboxyl (- COOH) ,-OC (=O) R " ', sulfonic group (- SO₃H), sulfophenyl, warp Replace or be unsubstituted alkyl, be substituted or be unsubstituted naphthenic base, be substituted or be unsubstituted alkoxy, be substituted Or be unsubstituted aryloxy group, be substituted or be unsubstituted alkyl sulfenyl, be substituted or be unsubstituted artyl sulfo, through taking Generation or be unsubstituted alkyl sulphonyl, be substituted or be unsubstituted aryl sulfonyl, be substituted or be unsubstituted alkenyl, The silicyl that is substituted or is unsubstituted, the boryl for being substituted or being unsubstituted, the amido for being substituted or being unsubstituted, through taking Generation or the aryl phosphino- being unsubstituted, the oxidation phosphino- for being substituted or being unsubstituted, the aryl that is substituted or is unsubstituted or The heteroaryl or adjacent group that are substituted or are unsubstituted can connect to each other to form the ring for being substituted or being unsubstituted, And

R " ' is the alkyl for being substituted or being unsubstituted.

2. compound according to claim 1, wherein A is direct key, ether, carbonyl, two ester groups, sulfuryl, has 1 to 10 The alkylidene of a carbon atom or halogeno alkylen with 1 to 10 carbon atom.

3. compound according to claim 2, wherein the diester base includes the functional group indicated by following formula 2:

[chemical formula 2]

Wherein, in chemical formula 2, X is the alkylidene with 1 to 10 carbon atom, the miscellaneous alkane in Asia with 1 to 10 carbon atom Base, the halogeno alkylen with 1 to 10 carbon atom, the arlydene with 6 to 20 carbon atoms have 3 to 20 carbon atoms Inferior heteroaryl.

4. compound according to claim 1, wherein at least one of Q1, Q2 and R17 to R26 can be with adjacent functions Group combines to form the aromatic ring for being substituted or being unsubstituted.

5. compound according to claim 1, wherein Y1 and Y2 are respectively direct key.

6. compound according to claim 1, wherein the compound of chemical formula 1 is indicated by following formula 1-1:

[chemical formula 1-1]

Wherein, in chemical formula 1-1,

A is direct key, ether, carbonyl, two ester groups, sulfuryl, the alkylidene with 1 to 10 carbon atom or has 1 to 10 carbon The halogeno alkylen of atom, and

R27 and R28 are same or different to each other, and are each independently phenyl or naphthyl.

7. compound according to claim 1, wherein the compound of chemical formula 1 is indicated by following formula 1-2 or 1-3:

[chemical formula 1-2]

[chemical formula 1-3]

Wherein, in chemical formula 1-2 or 1-3,

R28 to R31 is same or different to each other, and is each independently phenyl or naphthyl.

8. compound according to claim 1, wherein the compound of chemical formula 1 is by following formula 1-4 into 1-15 Any one is indicated:

[chemical formula 1-4]

[chemical formula 1-5]

[chemical formula 1-6]

[chemical formula 1-7]

[chemical formula 1-8]

[chemical formula 1-9]

[chemical formula 1-10]

[chemical formula 1-11]

[chemical formula 1-12]

[chemical formula 1-13]

[chemical formula 1-14]

[chemical formula 1-15]

9. a kind of color material composition includes compound according to claim 1.

10. color material composition according to claim 9 also includes at least one of dyestuff and pigment.

11. a kind of photosensitive resin composition includes compound according to claim 1 or according to claim 9 Color material composition；Adhesive resin；Polyfunctional monomer；Photoinitiator and solvent.

12. photosensitive resin composition according to claim 11, wherein being contained based on consolidating in the photosensitive resin composition The total weight of object, the content of the compound are 5 weight % to 60 weight %.

13. a kind of light-sensitive material includes photosensitive resin composition according to claim 11.

14. a kind of colour filter includes light-sensitive material according to claim 13.

15. a kind of display device, including colour filter according to claim 14.