JP6753597B2 - Compound and photosensitive resin composition containing the compound - Google Patents

Description

Cross-reference of related applications This application claims the benefit of priority under Korean Patent Application No. 10-2017-0048106 dated April 13, 2017, and all the contents disclosed in the literature of the Korean patent application are Included as part of this specification.

The present invention relates to a compound, a photosensitive resin composition containing the compound, and a photosensitive material, a color filter, and a display element manufactured by using the compound. More specifically, the present invention relates to a compound having excellent color characteristics, heat resistance and solvent resistance, a photosensitive resin composition using the same, and a photosensitive material, a color filter and a display element manufactured by using the compound.

Recently, color filters are required to have high brightness and high brightness / dark ratio. In addition, one of the main purposes of developing a display element is to differentiate the performance of the display element by improving the color purity and to improve the productivity in the manufacturing process.

Since the pigment type conventionally used as a coloring material for a color filter exists in a color photoresist in a particle-dispersed state, it is difficult to adjust the brightness and the light-dark ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, they aggregate in the color filter to reduce their solubility and dispersibility, and the large particles that are aggregated cause multiple scattering of light. Such scattering of polarized light is cited as a main factor for lowering the light-dark ratio.

On the other hand, efforts are being made to improve the brightness and contrast ratio through ultra-fine graining and dispersion stabilization of pigments, but there is a degree of freedom in selecting color materials to realize color coordinates for high-color purity display devices. Be restricted.

In addition, the pigment dispersion method using a color material that has already been developed, particularly a pigment, has reached a limit in improving the color purity, brightness, and light-dark ratio of a color filter using the pigment dispersion method.

As a result, there is a demand for the development of new color materials capable of increasing color purity to improve color reproduction, brightness and light-dark ratio.

An object of the present invention is to provide a compound having excellent color characteristics, heat resistance and solvent resistance.

Another object of the present invention is to provide a photosensitive resin composition containing the above compound.

Another object of the present invention is to provide a photosensitive material, a color filter and a display element manufactured by using the compound or the photosensitive resin composition.

As used herein, the compounds represented by Chemical Formula 1 are provided.

Also provided herein is a colorant composition comprising said compound.

Also provided herein are photosensitive resin compositions comprising said compounds or colorant compositions.

The present specification also provides a photosensitive material produced by using the photosensitive resin composition, and a color filter or a display device using the photosensitive material.

Hereinafter, the compound according to the specific embodiment of the invention and the photosensitive resin composition containing the compound will be described in more detail.

In the present specification, when a part "contains" a component, this means that the other component may be further included, rather than excluding the other component, unless otherwise specified. To do.

Examples of substituents are described herein below, but are not limited thereto.

As used herein, the term "substitution" means that another working group is attached in place of the hydrogen atom in the compound, and the substituted position is the position where the hydrogen atom is substituted, that is, the substituent. Is not limited as long as it is a substitutable position, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein refers to dehydrogen; halogen group; cyano group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amide group; amino group; carboxy group; sulfone. Acid group; sulfonamide group; phosphine oxide group; alkoxy group; aryloxy group; alkylthioxy group; arylthioxy group; alkylsulfoxi group; arylsulfoxi group; silyl group; boron group; alkyl group; cycloalkyl group; Alkenyl group; aryl group; alalkyl group; alalkenyl group; alkylaryl group; arylphosphin group; or one or more selected from the group consisting of a heterocyclic group containing one or more of N, O and S atoms. It means that it has been substituted or unsubstituted with a substituent of the above, or that two or more of the above-exemplified substituents have been linked and substituted. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are linked.

は、他の置換基に連結される結合を意味し、単一結合は、Ｌで表される部分に別途の原子が存在しないことを意味する。 In this specification,

Means a bond linked to another substituent, and a single bond means that there is no separate atom in the portion represented by L.

Examples of halogen groups herein include fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it can be a compound having the following structure, but is not limited to this.

As used herein, the amide group may be such that the nitrogen of the amide group is substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it can be a compound having the following structural formula, but is not limited to this.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it can be a compound having the following structure, but is not limited to this.

As used herein, the ester group may have oxygen in the ester group substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it can be a compound having the following structural formula, but is not limited to this.

In the present specification, the sulfonamide group may be -SO ₂ NR'R ", and the R'and R" are the same or different from each other and are independently hydrogen; heavy hydrogen; halogen; nitrile group; Substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted It may be selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. Further, according to one embodiment, the alkyl group has 1 to 10 carbon atoms. Further, according to one embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, Pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , N-Heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, There are, but are not limited to, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.

As used herein, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy. , 3,3-Dimethylbutyloxy, 2-Ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.

In the present specification, the amine group is -NH ₂ , monoalkylamine group, dialkylamine group, N-alkylarylamine group, monoarylamine group, diarylamine group, N-arylheteroarylamine group, N-alkylhetero It may be selected from the group consisting of an arylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group and diphenylamine. Group, ditrilamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N-phenyltrilamine group, triphenylamine group, N-naphthylfluorenylamine group, N-phenylphenanthreni There are ruamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group and the like. , Not limited to this.

As used herein, the N-alkylarylamine group means an amine group in which the alkyl group and the aryl group are substituted with N of the amine group.

As used herein, the N-aryl heteroarylamine group means an amine group in which the N of the amine group is substituted with an aryl group and a heteroaryl group.

As used herein, the N-alkyl heteroarylamine group means an amine group in which the N of the amine group is substituted with an alkyl group and a heteroarylamine group.

In the present specification, the alkyl group among the monoalkylamine group, the dialkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkylsulfoxy group and the N-alkylheteroarylamine group is an example of the above-mentioned alkyl group. It is as follows. Specifically, the alkylthioxy group includes a methylthioxy group, an ethylthioxy group, a tert-butyltioxy group, a hexylthioxy group, an octylthioxy group and the like, and the alkylsulfoxy group includes a methylsulfoxy group and an ethylsulfoxy group. , Vulous sulfoxy group, butyl sulfoxy group, etc., but is not limited to this.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. Further, according to one embodiment, the alkenyl group has 2 to 10 carbon atoms. Further, according to one embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-prophenyl, isoprophenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1 , 3-Butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl There are, but are not limited to, -1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stillbenyl group, styrenyl group and the like.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like. Yes, but not limited to this.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the phosphine oxide group includes, but is not limited to, a diphenylphosphine oxide group and a dinaphthylphosphine oxide group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group can be a phenyl group, a biphenyl group, a terphenyl group, or the like as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group can be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenel group, a chrysenyl group, a fluorenyl group and the like.

などになることができる。ただし、これに限定されるのではない。 In the present specification, the fluorenyl group may be substituted, or the two substituents may be bonded to each other to form a spiro structure. If the fluorenyl group is substituted

And so on. However, it is not limited to this.

In the present specification, the "adjacent" group is a substituent substituted with an atom in which the substituent is directly linked to the substituted atom, a substituent located sterically closest to the substituent, or the said group. Substituents can mean other substituents substituted on the substituted atom. For example, two substituents substituted at the ortho position on the benzene ring and two substituents substituted on the same carbon on the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, aryl among monoarylamine groups, diarylamine groups, aryloxy groups, aryltioxy groups, arylsulfoxi groups, N-arylalkylamine groups, N-arylheteroarylamine groups and arylphosphin groups. The groups are as exemplified by the aryl groups described above. Specifically, the aryloxy group includes a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, 3 − Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, There are 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group and the like, and the aryltioxy group includes phenylthio. There are an oxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group and the like, and examples of the arylsulfoxi group include, but are limited to, a benzenesulfoxi group and a p-toluenesulfoxi group. It is not done.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Se and S as a heterologous element, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is 2 to 60. It is preferable to have. Examples of heterocyclic groups include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxaziazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acrizyl group, pyridazine Group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolin group, indol group, carbazole group, benzoxazole group, benzoimidazole group, benzo There are thiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group. However, it is not limited to these.

In the present specification, the heteroaryl group contains one or more non-carbon atoms and heteroatoms, and specifically, the heteroatoms are atoms selected from the group consisting of O, N, Se, S and the like. It may contain 1 or more. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, triazolyl group, acrizyl group and pyridadinyl group. Pyrazineyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, Benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthrolinyl group (phenanthroline), thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, aziridyl group, azaindrill group , Isoindrill group, indazolyl group, purine group, pteridine group, β-carboryl group, naphthylidine group, ter-pyridyl group, phenazinyl group, imidazole pyridyl group, pyropyridyl group, azepine group, pyrazolyl group. And dibenzofuranyl groups, but are not limited to this.

In the present specification, examples of heteroaryl groups among monoheteroarylamine groups, diheteroarylamine groups, N-arylheteroarylamine groups, and N-alkylheteroarylamine groups are examples of the above-mentioned heteroaryl groups. You may choose from.

In the present specification, the alkylene group is a divalent acting group derived from an alkane, for example, a linear type, a branched type or a cyclic group, and is a methylene group, an ethylene group, a propylene group or an isobutylene group. , Sec-butylene group, tert-butylene group, pentylene group, hexylene group and the like.

In the present specification, the haloalkylene group means an working group in which a halogen group is substituted with the above-mentioned alkylene group, and is, for example, perfluoropropane-2,2-diyl (perfluoropropane-2,2-dir). Can be done.

As used herein, an arylene group means an aryl group having two bond positions, that is, a divalent group. The above description of the aryl group is applicable, except that each of these is a divalent group.

As used herein, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" is a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle. means.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic-aliphatic fused ring, and is an example of the cycloalkyl group or the aryl group except that it is not monovalent. It may be selected from.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from the examples of the aryl group except that it is not monovalent.

In the present specification, the heterocycle contains one or more non-carbon atoms and heteroatoms, and specifically, the heterocycle contains one or more atoms selected from the group consisting of O, N, Se, S, and the like. It may be included. The heterocycle may be a monocyclic or polycyclic, aromatic, aliphatic or aromatic-aliphatic fused ring, except that it is not monovalent. It may be selected from the examples of.

As used herein, the term "direct bond" means that any atom or group of atoms does not exist at that position and is therefore connected by a bond line.

前記化学式１で、
Ｙ１およびＹ２は、互いに同一または異なり、それぞれ独立に、直接結合または−ＣＱ１Ｑ２−であり、
Ａは、直接結合；エーテル基；カルボニル基；エステル基；ジエステル基；ペルオキシ基；アミノ基；イミノ基；イミド基；アゾ基；アミド基；スルホン基；炭素数１から１０のアルキレン基；炭素数１から１０のヘテロアルキレン基；炭素数１から１０のハロアルキレン基；炭素数６から２０のアリーレン基；または炭素数３から２０のヘテロアリーレン基であり、
Ｒ１からＲ２６、Ｑ１およびＱ２は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；カルボニル基；エステル基；イミド基；アミド基；カルボキシ基（−ＣＯＯＨ）；−ＯＣ（＝Ｏ）Ｒ"'；スルホン酸基（−ＳＯ_３Ｈ）；スルホンアミド基；置換または非置換されたアルキル基；置換または非置換されたシクロアルキル基；置換または非置換されたアルコキシ基；置換または非置換されたアリールオキシ基；置換または非置換されたアルキルチオキシ基；置換または非置換されたアリールチオキシ基；置換または非置換されたアルキルスルホキシ基；置換または非置換されたアリールスルホキシ基；置換または非置換されたアルケニル基；置換または非置換されたシリル基；置換または非置換されたホウ素基；置換または非置換されたアミン基；置換または非置換されたアリールホスフィン基；置換または非置換されたホスフィンオキシド基；置換または非置換されたアリール基；または置換または非置換されたヘテロアリール基であるか、隣接した基は互いに結合して置換または非置換された環を形成してもよく、
Ｒ"'は、置換または非置換されたアルキル基である。 According to one embodiment of the invention, a compound represented by the following chemical formula 1 can be provided.
[Chemical formula 1]

With the above chemical formula 1,
Y1 and Y2 are the same or different from each other and are independently linked or -CQ1Q2-.
A is a direct bond; an ether group; a carbonyl group; an ester group; a diester group; a peroxy group; an amino group; an imino group; an imide group; an azo group; an amide group; a sulfone group; an alkylene group having 1 to 10 carbon atoms; 1 to 10 heteroalkylene groups; 1 to 10 carbon haloalkylene groups; 6 to 20 carbon number arylene groups; or 3 to 20 carbon number heteroarylene groups.
R1 to R26, Q1 and Q2 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amide group; carboxy group ( -COOH); - OC (= O ) R "'; sulfonic acid group _(-SO 3 H); sulfonamido group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted Substituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthioxy group; substituted or unsubstituted aryltioxy group; substituted or unsubstituted alkylsulfoxy group; substituted or unsubstituted Substitutable aryl sulfoxy group; substituted or unsubstituted alkenyl group; substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted amine group; substituted or unsubstituted Alylphosphin group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other and substituted or unsubstituted. May form a ring
R "'is a substituted or unsubstituted alkyl group.

As represented by the chemical formula 1, the present inventors can prevent the reaggregation of the compound by increasing the solubility of the compound in the solvent due to the sulfonate group contained in the molecular structure, and foreign substances can be prevented. The invention was completed by confirming through experiments that the color purity, brightness, and light-dark ratio can be improved when the generation is suppressed and applied to a color filter.

In particular, in the compound of the above embodiment, two sulfonate groups are introduced into the molecular structure by dimer formation, and the effect of improving the solubility by the sulfonate groups can be further enhanced, and the spectrum emitted from the light source and the color filter. The absorption and transmission spectra of the above are properly combined, and not only the color purity can be improved to improve the color reproduction and the brightness and the brightness / darkness ratio, but also the heat resistance is improved by increasing the molecular weight, and the heat treatment step at the time of manufacturing the photosensitive material is performed. Since the color purity, the brightness, and the brightness / darkness ratio do not change abruptly afterwards, stable display performance can be realized.

Further, the compound of the above embodiment has improved heat resistance by using an aromatic acting group bonded to the terminal of the sulfonate group, for example, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms. The effect of can be realized.

Specifically, in the above chemical formula 1, Y1 and Y2 are the same or different from each other and are independently bonded or -CQ1Q2-, respectively, in the above-CQ1Q2-, C is carbon, and Q1 and Q2 are independent, respectively. In addition, it can mean an active group attached to carbon. Therefore, when the Y1 or Y2 is a direct bond, a pentagonal ring having 5 carbon atoms is formed, and when the Y1 or Y2 is −CQ1Q2-, a hexagonal ring having 6 carbon atoms is formed. You may.

Further, in the above chemical formula 1, A is a direct bond; ether group; carbonyl group; ester group; diester group; peroxy group; amino group; imino group; imide group; azo group; amide group; sulfone group; carbon number 1 to 10. Alkylene group; heteroalkylene group having 1 to 10 carbon atoms; haloalkylene group having 1 to 10 carbon atoms; arylene group having 6 to 20 carbon atoms; or heteroarylene group having 3 to 20 carbon atoms.

More preferably, in the chemical formula 1, A may be a direct bond; an ether group; a carbonyl group; a diester group; a sulfone group; an alkylene group having 1 to 10 carbon atoms; or a haloalkylene group having 1 to 10 carbon atoms. ..

前記化学式２で、Ｘは、炭素数１から１０のアルキレン基；炭素数１から１０のヘテロアルキレン基；炭素数１から１０のハロアルキレン基；炭素数６から２０のアリーレン基；または炭素数３から２０のヘテロアリーレン基である。好ましくは、前記Ｘは、炭素数１から５のアルキレン基、例えば、メチレン基、エチレン基、プロピレン基などを用いてもよい。 The diester group is an active group containing two ester active groups, and may contain, for example, an active group represented by the following chemical formula 2.
[Chemical formula 2]

In the chemical formula 2, X is an alkylene group having 1 to 10 carbon atoms; a heteroalkylene group having 1 to 10 carbon atoms; a haloalkylene group having 1 to 10 carbon atoms; an arylene group having 6 to 20 carbon atoms; or 3 carbon atoms. From 20 heteroallylen groups. Preferably, the X may use an alkylene group having 1 to 5 carbon atoms, for example, a methylene group, an ethylene group, a propylene group, or the like.

The haloalkylene group having 1 to 10 carbon atoms means an working group in which a halogen group is substituted with an alkylene group having 1 to 10 carbon atoms, and for example, perfluoropropane-2,2-diyl (perfluoropropane-2,2-). Diyl) and so on.

In the above chemical formula 1, R1 to R26 are the same or different from each other, and independently, hydrogen; halogen group; nitro group; carboxy group; ester group; hydroxy group; -OC (= O) R "'; sulfonic acid group ( -SO 3 _H); substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy group; or a substituted or unsubstituted aryl groups, adjacent groups , May be combined with each other to form substituted or unsubstituted rings.

The R "'is a substituted or unsubstituted alkyl group.

The R "'is a methyl group.

In the above chemical formula 1, R1 to R26 are the same or different from each other, and independently of each other, hydrogen; fluorine; chlorine; bromine; iodine; nitro group; carboxy group; alkyl ester group; cycloalkyl ester group; arylalkyl ester group; hydroxy. _{group; -OC (= O) CH 3} ; sulfonic acid group _(-SO 3 H); may be or naphthyl group; a methyl group; t-butyl group; methoxy group; a phenyl group.

In the above chemical formula 1, at least one of Q1, Q2, R17 to R26 may be bonded to an adjacent working group to form a substituted or unsubstituted aromatic ring.

Specifically, in the above chemical formula 1, at least one of Q1, Q2, R17 to R26 is a benzene ring substituted or substituted by binding to an adjacent working group; or substituted or unsubstituted naphthalene. A ring may be formed.

In the above chemical formula 1, Y1 and Y2 may be independently and directly bonded to each other.

前記化学式１−１で、
Ａは、直接結合；エーテル基；カルボニル基；ジエステル基；スルホン基；炭素数１から１０のアルキレン基；または炭素数１から１０のハロアルキレン基であり、Ｒ２７およびＲ２８は、互いに同一または異なり、それぞれ独立に、フェニル基またはナフチル基である。 The compound of the above embodiment may be represented by the following chemical formula 1-1.
[Chemical formula 1-1]

With the above chemical formula 1-1
A is a direct bond; an ether group; a carbonyl group; a diester group; a sulfone group; an alkylene group having 1 to 10 carbon atoms; or a haloalkylene group having 1 to 10 carbon atoms, and R27 and R28 are the same or different from each other. Each is independently a phenyl group or a naphthyl group.

［化学式１−３］

前記化学式１−２または１−３で、Ａは、直接結合；エーテル基；カルボニル基；ジエステル基；スルホン基；炭素数１から１０のアルキレン基；または炭素数１から１０のハロアルキレン基であり、Ｒ２８からＲ３１は、互いに同一または異なり、それぞれ独立に、フェニル基またはナフチル基である。 Further, the compound of the above embodiment may be represented by the following chemical formula 1-2 or chemical formula 1-3.
[Chemical formula 1-2]

[Chemical formula 1-3]

In the chemical formula 1-2 or 1-3, A is a direct bond; an ether group; a carbonyl group; a diester group; a sulfone group; an alkylene group having 1 to 10 carbon atoms; or a haloalkylene group having 1 to 10 carbon atoms. , R28 to R31 are the same or different from each other and are independently phenyl or naphthyl groups.

［化学式１−５］

［化学式１−６］

［化学式１−７］

［化学式１−８］

［化学式１−９］

［化学式１−１０］

［化学式１−１１］

［化学式１−１２］

［化学式１−１３］

［化学式１−１４］

［化学式１−１５］

The compound of the above embodiment may be represented by any one of the following chemical formulas 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]

On the other hand, according to another embodiment of the invention, a color material composition containing the compound of the one embodiment can be provided.

The content relating to the compound includes the content described above with respect to the one embodiment.

The color material composition may further contain at least one of a dye and a pigment. For example, the colorant composition may contain only the compound of the one embodiment, but may contain the compound of the one embodiment and one or more dyes, or the compound of the one embodiment and one or more pigments. Or may contain one or more dyes and one or more pigments of the compound of the above embodiment.

At this time, the specific type of the dye (Dye) or the pigment (Pigment) used is not largely limited, and various substances widely used in the field of color filters or displays may be used without limitation.

On the other hand, according to still another embodiment of the invention, the compound of the one embodiment or the color material composition of the other embodiment; a binder resin; a polyfunctional monomer; a photoinitiator; and a photosensitive resin containing a solvent. Compositions may be provided.

The content relating to the compound includes the content described above with respect to the one embodiment, and the content relating to the colorant composition includes the content described above with respect to the other embodiment.

The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of the film produced by the resin composition.

The binder resin may be a copolymer resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility, and may further contain a binder generally used in the art.

The polyfunctional monomer that imparts mechanical strength to the film is any one or more of unsaturated carboxylic acid eltels; aromatic vinyls; unsaturated ethers; unsaturated imides; and acid anhydrides. There may be.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl (meth) acrylate. ) Acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobonyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) ) Acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) ) Acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) ) Methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate , 1,1,1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxy It may be selected from the group consisting of methyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but is not limited thereto.

Specific examples of the aromatic vinyl monomers include styrene, α-methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m). , P) -Choose from the group consisting of chlorostyrene, but is not limited to these.

Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ethers, vinyl ethyl ethers, and allyl glycidyl ethers, but are not limited thereto.

Specific examples of the unsaturated imides may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. Good, but not limited to these.

Examples of the acid anhydride include, but are not limited to, maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride.

The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group, and for example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2- 1 selected from the group consisting of carboxylic acid, mono-2-((meth) acryloyloxy) ethylphthalate, mono-2-((meth) acryloyloxy) ethylsuccinate, ω-carboxypolycaprolactone mono (meth) acrylate 1 It is preferable to use more than seeds, but it is not limited to these.

According to one embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOHmg / g, and the weight average molecular weight is 1,000 to 50,000.

The polyfunctional monomer is a monomer that plays a role of forming a photoresist image by light, and specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6-. Hexadiol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, penta It may be one or a mixture of two or more selected from the group consisting of erythritol tetramethritol and dipentaerythritol hexamethritol.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to induce cross-linking, and is, for example, a group consisting of an acetophenone-based compound, a biimidazole-based compound, a triazine-based compound, and an oxime-based compound. It may be one or more selected from the above.

The acetphenone compounds are 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1-one, 4- (2-). Hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoinmethyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-Methyl- (4-methylthio) Phenyl-2-morpholino-1-propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, 2-( 4-Bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, etc. There is, and is not limited to this.

Examples of the biimidazole compound include 2,2-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (o-chlorophenyl) -4,4'. , 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4', 5,5' -Tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, and the like, but not limited to this.

The triazine-based compound is 3-{4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl. -3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine -6-yl] phenylthio} acetate, 2-epoxyethyl-2-{4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, cyclohexyl-2-{4- [ 2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, benzyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} Acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s -Triazine-6-yl] phenylthio} propionamide, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-) Dimethylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but not limited to this.

The oxime compounds are 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Ciba Geigy, CGI124), ethanone-1- (9-ethyl) -6-. (2-Methylbenzoyl-3-yl) -1- (O-acetyloxime) (CGI242), N-1919 (Adeca), and the like, and are not limited thereto.

The solvents used are acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether. , Diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, octane, cyclohexane, Benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl One or more selected from the group consisting of ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether. It may be, but it is not limited to this.

The content of the compound may be 5% by weight to 60% by weight based on the total weight of the solid content in the photosensitive resin composition. The content of the binder resin may be 1% by weight to 60% by weight, the content of the photoinitiator is 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is The content is 0.1% by weight to 50% by weight.

The total weight of the solid content means the total weight of the components of the resin composition excluding the solvent. The weight% standard based on the solid content and the solid content of each component can be measured by a general analytical means used in the industry such as liquid chromatography or gas chromatography.

In addition, the photosensitive resin composition may further contain an antioxidant. The content of the antioxidant is 0.1% by weight to 20% by weight based on the total weight of the solid content in the photosensitive resin composition.

The antioxidant may be at least one selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants and phosphine antioxidants. Good, but not limited to this.

Specific examples of the antioxidant are phosphate-based heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4). -Hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl- 2,4,6-Tris (3,5-di-t-butyl-4-hydroxybenzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzyl phosphate diethyl ester, 2,2-thiobis ( 4-Methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butyl redene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl) -6-t-butylphenol) or bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-) Hindered phenolic primary antioxidants such as 3'-tert-butylphenyl) butanoicacid] glycol ester); phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p- Amine-based secondary antioxidants such as phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole Or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] a thio-based secondary antioxidant such as methane; or triphenyl phosphate, tris (nonylphenyl) phosphate, triisodecyl phosphate, Bis (2,4-dibutylphenyl) pentaerythritol diphosphate (Bis (2,4-dibutylpeneyl) Phenollythritol Hydrosphite or (1,1'-biphenyl) -4,4'-diylbisphosphonate tetrakis [2,4-bis (1,1-Dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4'-Diylbisphosphonous Phenyl-based secondary antioxidants such as acid tetrakis [2,4-bis (1,1-dimethylyl) phenyl] ester] can be mentioned.

The photosensitive resin composition is selected from the group consisting of a photocrosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant and a leveling agent1 Alternatively, two or more additives may be additionally included. The content of the additive is 0.1% by weight to 20% by weight based on the total weight of the solid content in the photosensitive resin composition.

The photocrosslinked sensitizers are benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3, Benzophenone compounds such as 3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9- Fluolenone compounds such as fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone; xanthone, 2-methylxanthone, etc. Xanthone compounds; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenylacrine, 1,7-bis (9) Acrydin compounds such as −acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; benzyl, 1,7,7-trimethyl-bicyclo [2, 2,1] Dicarbonyl compounds such as heptane-2,3-dione, 9,10-phenanthrequinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2, Phosphine oxide compounds such as 4,4-trimethylpentylphosphine oxide; methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate, etc. Benzophenone compounds; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin , 3-Benzoyl-7-methoxy-coumarin, 10,10-carbonyl Bis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolidine-11-one, etc. One or more selected from the group consisting of coumarin compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthiazoline; may be used.

The curing accelerator is used for enhancing curing and mechanical strength, and specifically 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3, 4-Thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2-mercapto) One or more selected from the group consisting of (acetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate). May be used.

Adhesion promoters used herein include metaacryloylsilane coupling agents such as metaacryloyloxypropyltrimethoxysilane, metaacryloyloxypropyldimethoxysilane, metaacryloyloxypropyltriethoxysilane, and metaacryloyloxypropyldimethoxysilane. One or more of them may be selected and used, and as the alkyltrimethoxysilane, one or more may be selected and used from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like.

The surfactant is a silicon-based surfactant or a fluorine-based surfactant, and specifically, the silicon-based surfactant is BYK-077, BYK-085, BYK-300, BYK-301 manufactured by BYK-Chemie. , BYK-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 As the fluorine-based surfactant, F-114, F-177, F-410, F-411, F-450, F-493, F- of DIC (DaiNippon Ink & Chemicals) may be used. 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 and the like may be used, but the present invention is not limited thereto.

As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone and the like may be used, but the present invention is not limited thereto. Anything commonly used in the industry may be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxyamine aluminum salt. , P-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2-methylenebis (4-methyl-6-t) It may contain one or more selected from the group consisting of −butylphenol), 2-mercaptoimidazole and phenothiazine, but the present invention is not limited thereto, and those generally known in the art are included. It may be included.

The dispersant may be used by a method of internally adding the pigment to the pigment in a form of surface treatment in advance, or a method of externally adding the pigment to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and a fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric surfactant. And so on. These may be used individually or in combination of two or more.

Specifically, the dispersant includes polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, and carboxylate. There is, but is not limited to, one or more selected from the group consisting of alkylamide alkylene oxide additions and alkylamines.

The leveling agent may be polymeric or non-polymeric. Specific examples of polymer-based leveling agents include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-. Including, but not limited to, containing and non-polymeric nitrogen-containing compounds, all commonly used in the art may be used.

The photosensitive resin composition is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode, and forming an overcoat layer. Even if it is used for photosensitive materials for thin film transistors, column spacer photosensitive materials, photocurable paints, photocurable inks, photocurable adhesives, printing boards, photosensitive materials for printing wiring boards, photosensitive materials for plasma display panels (PDPs), etc. Often, there are no particular restrictions on its use.

On the other hand, according to another embodiment of the invention, a photosensitive material produced by using the photosensitive resin composition of the above-described embodiment can be provided.

The contents relating to the photosensitive resin composition include the contents described above with respect to the other embodiments.

Specifically, the photosensitive resin composition of the above embodiment may be applied onto a substrate to form a thin film or a photosensitive material in the form of a pattern. The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like may be used, and a spin coating method is generally widely used. Further, after forming the coating film, a part of the residual solvent may be removed under reduced pressure in some cases.

Examples of the light source for curing the photosensitive resin composition include, but are limited to, a mercury vapor arc (arc), a carbon arc, and an Xe arc that emit light having a wavelength of 250 nm to 450 nm. is not.

On the other hand, according to still another embodiment of the invention, a color filter containing the photosensitive material of the above embodiment can be provided.

The content relating to the photosensitive material includes the content described above with respect to the other embodiment.

The color filter may be produced by using a photosensitive resin composition containing the compound of the above embodiment. The photosensitive resin composition may be applied onto a substrate to form a coating film, and the coating film may be exposed, developed and cured to form a color filter.

Since the photosensitive resin composition has excellent heat resistance and little color change due to heat treatment, it provides a color filter having a high color reproduction rate and a high brightness and light-dark ratio even during the manufacturing and curing process of the color filter. be able to.

The substrate may be a glass plate, a silicon wafer, a plate made of a plastic base material such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type thereof is not particularly limited.

The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.

Further, according to one embodiment, the color filter may further include an overcoat layer.

A grid-like black pattern called a black matrix may be arranged between the color pixels of the color filter for the purpose of improving contrast. Chromium may be used as the material of the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching may be used. However, in consideration of high cost in the process, high reflectance of chromium, and environmental pollution by chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing may be used.

The black matrix according to one embodiment of the present specification may use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone or a mixture of carbon black and a coloring pigment may be used. At this time, since the coloring pigment having insufficient light-shielding property is mixed, the amount of the coloring material is relatively increased. It also has the advantage that the strength of the film or the adhesion to the substrate does not decrease.

On the other hand, according to still another embodiment of the invention, a display device including the color filter of the embodiment may be provided.

The content relating to the color filter includes the content described above with respect to the other embodiment.

The display device includes a plasma display panel (Plasma Display Panel, PDP), a light emitting diode (Light Emitting Device, LED), an organic light emitting element (Organic Light Emitting Device, OLED), a liquid crystal display device (Liquid Crystal Disk), and a liquid crystal display device (Liquid Crystal Display). It may be any one of a liquid crystal display device (Thin Film Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (Cathode Ray Tube, CRT).

According to the present invention, a compound having excellent color characteristics, heat resistance and solvent resistance, a photosensitive resin composition using the compound, and a photosensitive material, a color filter and a display element manufactured by using the compound are provided. obtain.

The invention will be described in more detail with reference to the following examples. However, the following examples merely exemplify the present invention, and the content of the present invention is not limited to the following examples.

<Manufacturing Examples 1 and 2>

２５ｇ（１５７．０４１ｍｍｏｌ、１ｅｑ）の化合物１をメチレンクロライド２００ｇ（製造：大正）に入れ、攪拌した。アイス−バス（Ｉｃｅ−ｂａｔｈ）を設置して反応液を０℃に作り、トリエチルアミン（Ｔｒｉｅｔｈｙｌａｍｉｎｅ、ＴＥＡ）１９．０７ｇ（１８８．４５４ｍｍｏｌ、１．２ｅｑ）を反応液に徐々に滴下させた。 Production example 1
Compound A-1 was synthesized through a reaction as shown in [Reaction formula 1] below.
[Reaction formula 1]

25 g (157.041 mmol, 1 eq) of Compound 1 was placed in 200 g of methylene chloride (manufactured by Taisho) and stirred. An ice-bath was placed to prepare the reaction solution at 0 ° C., and 19.07 g (188.454 mmol, 1.2 eq) of triethylamine (TEA) was gradually added dropwise to the reaction solution.

Subsequently, 30.787 g (174.321 mmol, 1.11 eq) of Compound 2 was gradually added dropwise to the reaction solution. After reacting at 0 ° C. for 30 minutes, the mixture was stirred at room temperature for 24 hours. 300 g of distilled water (DI-water) was added to the reaction solution, and the mixture was stirred for 30 minutes, and then the organic layer and the aqueous layer were separated. 200 ml of MC was added to the separated aqueous layer for additional extraction. After stirring putting _K 2 _CO 3 5% solution 200ml of the organic layer, the organic layer was separated. Extraction was repeated until the organic layer was neutralized by adding distilled water. The solvent was removed from the organic layer under reduced pressure. The precipitate was added to 500 ml of a solution having an ethyl acetate (EA): n-hexane (n-Hexane) ratio of 1: 3, stirred, filtered under reduced pressure, and the precipitate was dried at 80 ° C. for 1 day to whiten. 45.736 g (152.79 mmol) of the solid compound A-1 of the above was obtained. (Yield: 97%)

1H NMR (500MHz, CDCl ₃ ): 8.00 to 7.97 (t, 3H), 7.70 to 7.68 (d, 1H), 7.66 to 7.65 (d, 1H), 7. 59 to 7.55 (t, 1H), 7.47 to 7.42 (q, 3H), 7.21 to 7.20 (d, 1H), 2.51 (s, 3H)

Production example 2
Compound A-2 is the same as in Production Example 1 except that 39.339 g (174.321 mmol, 1.11 eq) of Compound 3 was used instead of Compound 2 as shown in [Reaction Formula 2] below. Was synthesized.
[Reaction equation 2]

<Examples 1 to 12: Production of compounds, photosensitive resin compositions and photosensitive materials>

２−ｎｅｃｋ丸底フラスコに１ｇ（３．３９９ｍｍｏｌ）のＡ−１、０．５１８ｇ（１．６７０ｍｍｏｌ）のＢ−１、安息香酸（Ｂｅｎｚｏｉｃ ａｃｉｄ）１ｇ、メチルベンゾエート（Ｍｅｔｈｙｌ ｂｅｎｚｏａｔｅ）１０ｍｌを入れ、１８０℃で５時間攪拌した。以降、メタノール１００ｍｌを添加し、析出された物質を減圧フィルターした後、オーブンに乾燥させた。その結果、１．０５ｇ（１．２０２４ｍｍｏｌ）の化合物Ｃ−１を得た。（収率：７２％） Example 1
(1) Preparation of compound Compound C-1 was synthesized through the following reaction [Reaction formula 3].
[Reaction equation 3]

In a 2-neck round bottom flask, 1 g (3.399 mmol) of A-1, 0.518 g (1.670 mmol) of B-1, 1 g of benzoic acid, and 10 ml of methyl benzoate (Methyl benoate) are placed and 180. The mixture was stirred at ° C. for 5 hours. Then, 100 ml of methanol was added, and the precipitated substance was filtered under reduced pressure and then dried in an oven. As a result, 1.05 g (1.2024 mmol) of compound C-1 was obtained. (Yield: 72%)

The MS measurement results of the compound C-1 are as follows.

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

(2) Production of photosensitive resin composition 5.554 g of the compound C-1 synthesized above, a binder resin [copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70:30, acid value 113 KOH mg / g, GPC) Weight average molecular weight 20,000 g / mol, molecular weight distribution (PDI) 2.0, solid content (SC) 25%, solvent PGMEA included)] 10.376 g, photoinitiator (I-369, BASF) 2.018 g, additive (F-475, DIC) 1.016 g, photopolymerizable compound (Dipentaerythritol hexaacrylate, DPHA, Nippon Kayakusha) 12.443 g, solvent (Propyrene Glycol Monomethyl Ether Actate, PGMEA) 68 A photosensitive resin composition was produced by mixing .593 g.

(3) Production of Photosensitive Material The photosensitive resin composition was spin-coated on glass (5 cm x 5 cm) and preheated at a temperature of 100 ° C. for 100 seconds to form a film. The distance between the substrate on which the film was formed and the photomask (photomask) was set to 250 μm, and the front surface of the substrate was irradiated with an exposure amount of 40 mJ / cm ² using an exposure device. Subsequently, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and then heat-treated (post-bake) at 230 ° C. for 20 minutes to produce a substrate.

Example 2

(1) Preparation of Compound As shown in [Reaction Formula 4] below, the same as in Example 1 above, except that 0.493 g (1.590 mmol) of B-2 was used instead of Compound B-1. 0.9 g (1.051 mmol) of compound C-2 was synthesized by the above method. (Yield: 66%)

The MS measurement results of the compound C-2 are as follows.

Ionization mode =: APCI +: m / z = 857 [M + H] +, Exact Mass: 856
[Reaction formula 4]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-2 was used instead of compound C-1. Manufactured the material.

Example 3

(1) Preparation of Compound As shown in [Reaction Formula 5] below, the same as in Example 1 above, except that 0.493 g (1.590 mmol) of B-3 was used instead of Compound B-1. 1.1 g (1.284 mmol) of compound C-3 was synthesized by the above method. (Yield: 81%)

The MS measurement results of the compound C-3 are as follows.

Ionization mode =: APCI +: m / z = 857 [M + H] +, Exact Mass: 856
[Reaction formula 5]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-3 was used instead of compound C-1. Manufactured the material.

Example 4

(1) Preparation of Compound As shown in [Reaction Formula 6] below, the same as in Example 1 above, except that 0.512 g (1.590 mmol) of B-4 was used instead of Compound B-1. 1.26 g (1.343 mmol) of compound C-4 was synthesized by the above method. (Yield: 85%)

The MS measurement results of the compound C-4 are as follows.

Ionization mode =: APCI +: m / z = 884 [M + H] +, Exact Mass: 885
[Reaction formula 6]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-4 was used instead of compound C-1. Manufactured the material.

Example 5

(1) Preparation of Compound As shown in [Reaction Equation 7] below, the same as in Example 1 above, except that 0.652 g (1.590 mmol) of B-5 was used instead of Compound B-1. 0.82 g (0.843 mmol) of compound C-5 was synthesized by the above method. (Yield: 53%)

The MS measurement results of the compound C-5 are as follows.

Ionization mode =: APCI +: m / z = 949 [M + H] +, Exact Mass: 948
[Reaction equation 7]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-5 was used instead of compound C-1. Manufactured the material.

Example 6

(1) Preparation of Compound As shown in [Reaction Equation 8] below, the same as in Example 1 above, except that 0.706 g (1.590 mmol) of B-6 was used instead of Compound B-1. 1.3 g (1.288 mmol) of compound C-6 was synthesized by the above method. (Yield: 81%)

The MS measurement results of the compound C-6 are as follows.

Ionization mode =: APCI +: m / z = 949 [M + H] +, Exact Mass: 948
[Reaction equation 8]

(2) Manufacture of photosensitive resin composition and photosensitive material

A photosensitive resin composition and a photosensitive material were produced in the same manner as in Example 1 except that compound C-6 was used instead of compound C-1.

Example 7

(1) Preparation of Compound As shown in [Reaction Formula 9] below, 1 g (2.862 mmol) of A-2 is used instead of Compound A-1, and 0.444 g (1.431 mmol) of Compound B-1 is used. 1 g (1.030 mmol) of compound C-7 was synthesized in the same manner as in Example 1 above, except that it was present. (Yield: 71.9%)

The MS measurement results of the compound C-7 are as follows.

Ionization mode =: APCI +: m / z = 973 [M + H] +, Exact Mass: 972
[Reaction equation 9]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-7 was used instead of compound C-1. Manufactured the material.

Example 8

(1) Preparation of compound As shown in the following [Reaction formula 10], 1 g (2.862 mmol) of A-2 is used instead of compound A-1, and 0.421 g (1.431 mmol) of compound B-2 is used. 0.9 g (0.941 mmol) of Compound C-8 was synthesized in the same manner as in Example 1 above, except that the compound C-8 was synthesized. (Yield: 65.8%)

The MS measurement results of the compound C-8 are as follows.

Ionization mode =: APCI +: m / z = 957 [M + H] +, Exact Mass: 956
[Reaction equation 10]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-8 was used instead of compound C-1. Manufactured the material.

Example 9

(1) Preparation of compound As shown in [Reaction formula 11] below, 1 g (2.862 mmol) of A-2 is used instead of compound A-1, and 0.421 g (1.431 mmol) of compound B-3 is used. 0.9 g (0.941 mmol) of Compound C-9 was synthesized in the same manner as in Example 1 above, except that the compound C-9 was synthesized. (Yield: 65.8%)

The MS measurement results of the compound C-9 are as follows.

Ionization mode =: APCI +: m / z = 957 [M + H] +, Exact Mass: 956
[Reaction formula 11]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-9 was used instead of compound C-1. Manufactured the material.

Example 10

(1) Preparation of compound As shown in the following [Reaction formula 12], 1 g (2.862 mmol) of A-2 is used instead of compound A-1, and 0.461 g (1.431 mmol) of compound B-4 is used. Except for the above, 1 g (1.015 mmol) of compound C-10 was synthesized in the same manner as in Example 1 above. (Yield: 71%)

The MS measurement results of the compound C-10 are as follows.

Ionization mode =: APCI +: m / z = 985 [M + H] +, Exact Mass: 984
[Reaction equation 12]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-10 was used instead of compound C-1. Manufactured the material.

Example 11

(1) Preparation of compound As shown in [Reaction formula 13] below, 1 g (2.862 mmol) of A-2 is used instead of compound A-1, and compound B-5 is used for 0.586 g (1.431 mmol). 0.78 g (0.730 mmol) of compound C-11 was synthesized in the same manner as in Example 1 above, except that it was present. (Yield: 51%)

The MS measurement results of the compound C-11 are as follows.

Ionization mode =: APCI +: m / z = 1073 [M + H] +, Exact Mass: 1072
[Reaction equation 13]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-11 was used instead of compound C-1. Manufactured the material.

Example 12

(1) Preparation of compound As shown in the following [Reaction formula 14], 1 g (2.862 mmol) of A-2 is used instead of compound A-1, and compound B-6 is used for 0.636 g (1.431 mmol). 1.16 g (1.045 mmol) of compound C-12 was synthesized in the same manner as in Example 1 above, except that it was present. (Yield: 73%)

The MS measurement results of the compound C-12 are as follows.

Ionization mode =: APCI +: m / z = 1107 [M + H] +, Exact Mass: 1106
[Reaction equation 14]

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitivity were carried out in the same manner as in Example 1 except that compound C-12 was used instead of compound C-1. Manufactured the material.

<Comparative example: Production of compounds, photosensitive resin compositions and photosensitive materials>

Comparative Example 1

(1) Preparation of compound A PY138 pigment having the following chemical structure was used.

(2) Production of Photosensitive Resin Composition and Photosensitive Material The photosensitive resin composition and photosensitive material are prepared in the same manner as in Example 1 except that the PY138 pigment is used instead of the compound C-1. Manufactured.

<Experimental example: Measurement of physical properties of compounds, photosensitive resin compositions and photosensitive materials>
The physical properties of the photosensitive resin composition or the photosensitive material obtained in the above Examples and Comparative Examples were measured by the following methods, and the results are shown in Tables 1 to 3.

1. Solvent resistance For each of the compounds obtained in the above Examples and Comparative Examples, the solubility in dimethylformamide (DMF) organic solvent was measured, and the solvent resistance was evaluated according to the following criteria. The results are shown in Table 1. showed that.
◯: Solubility 1% or more X: Solubility less than 1% Results of Experimental Example 1

As shown in Table 1, the compounds of Examples had improved solubility in organic solvents as compared with Comparative Examples. The increased solubility is expected to be due to SO ₃ functional group contained in the compounds of the Examples.

As a result, unlike general pigments that require dispersion through derivatives, dispersants, etc. when dissolving organic solvents, the compounds of the above examples do not require derivatives or dispersants when dissolving organic solvents, and are commercially available. Can be easily applied.

2. Evaluation of Heat Resistance With respect to the preheat-treated (prebake) substrate obtained in the above example, a transmittance spectrum in the visible light region in the range of 380 nm to 780 nm was obtained using a spectroscope (MCPD-Otsuka).

Subsequently, the preheat-treated (prebake) substrate was additionally subjected to post-heat treatment (post-bake) at 230 ° C. for 20 minutes to obtain a transmittance spectrum with the same equipment and measurement range.

Eab was calculated using the obtained transmittance spectrum and the values E (L *, a *, b *) obtained by using the C light source backlight, and is shown in Table 2 below.
ΔE (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2
Eab = {ΔE after post-heat treatment (L *, a *, b *)}-{ΔE after pre-heat treatment (L *, a *, b *)}

A small ΔEab value means that the color heat resistance is excellent, and in the case of a color filter-related material, when the ΔEab value is less than 3, it is recognized as an excellent material.
Results of Experimental Example 2

As shown in Table 2, it was confirmed that the photosensitive material of the example had excellent color heat resistance because the Eab value was as small as less than 3.

Claims (10)

Compounds represented by the following chemical formula 1-1 :
[Chemical formula 1-1]

With the above chemical formula 1-1
A is a direct bond; an ether group; a carbonyl group ; a sulfone group; an alkylene group having 1 to 10 carbon atoms ; a haloalkylene group having 1 to 10 carbon atoms ; or a group represented by the following chemical formula 2 .
[Chemical formula 2]

In the chemical formula 2, X is an alkylene group having 1 to 10 carbon atoms; a heteroalkylene group having 1 to 10 carbon atoms; a haloalkylene group having 1 to 10 carbon atoms; an arylene group having 6 to 20 carbon atoms; or 3 carbon atoms. From 20 heteroallylen groups,
R27 and R28 are the same or different from each other and are independently phenyl or naphthyl groups. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-2 or chemical formula 1-3:
[Chemical formula 1-2]

[Chemical formula 1-3]

With the above chemical formula 1-2 or 1-3
A is a direct bond; an ether group; a carbonyl group ; a sulfone group; an alkylene group having 1 to 10 carbon atoms ; a haloalkylene group having 1 to 10 carbon atoms ; or a group represented by the chemical formula 2 .
In the chemical formula 2, X is an alkylene group having 1 to 10 carbon atoms; a heteroalkylene group having 1 to 10 carbon atoms; a haloalkylene group having 1 to 10 carbon atoms; an arylene group having 6 to 20 carbon atoms; or 3 carbon atoms. From 20 heteroallylen groups,
R28 to R31 are the same or different from each other and are independently phenyl or naphthyl groups. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 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]

A color material composition containing the compound according to any one of claims 1 to 3 . The color material composition according to claim 4 , further comprising at least one of a dye and a pigment. A photosensitive resin composition containing the compound according to any one of claims 1 to 3 or the coloring material composition according to claim 4 ; a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent. The photosensitive resin composition according to claim 6 , wherein the content of the compound is 5% by weight to 60% by weight based on the total weight of the solid content in the photosensitive resin composition. A photosensitive material comprising the photosensitive resin composition according to claim 6 or 7 . A color filter containing the photosensitive material according to claim 8 . A display device including the color filter according to claim 9 .