CN110557947B

CN110557947B - Quinophthalone compound, photosensitive resin composition containing same, photosensitive material, color filter, and display device

Info

Publication number: CN110557947B
Application number: CN201880006680.4A
Authority: CN
Inventors: 朴锺镐; 催相雅; 李多美; 梁承秦
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-04-04
Filing date: 2018-10-24
Publication date: 2022-06-14
Anticipated expiration: 2038-10-24
Also published as: JP2020520343A; TWI711673B; TW201942255A; KR102235984B1; WO2019194381A1; CN110557947A; KR20190115970A; JP6879481B2

Abstract

The present specification provides a compound represented by chemical formula 1, a photosensitive resin composition, a photosensitive material, a color filter, and a display device including the same.

Description

Quinophthalone compound, photosensitive resin composition containing same, photosensitive material, color filter, and display device

Technical Field

The present application claims priority to korean patent application No. 10-2018-0039312, which was filed to korean patent office on 4/2018, the contents of which are incorporated herein in their entirety.

The present specification relates to a quinophthalone compound and a photosensitive resin composition comprising the same. The present specification also relates to a photosensitive material and a color filter produced using the photosensitive resin composition, and a display device including the photosensitive material and the color filter.

Background

In recent years, color filters are required to have high brightness and high contrast. Further, one of the main purposes of development of display devices is to differentiate display element performance by improving color purity and to improve productivity in manufacturing processes.

Since pigment types that have been used as coloring materials for color filters exist in a particle-dispersed state in color photoresists, it is difficult to adjust the brightness and contrast by adjusting the size and distribution of pigment particles. In the case of pigment particles, dissolution and dispersibility are reduced by agglomeration in the color filter, and multiple scattering (multiple scattering) of light occurs due to agglomerated large particles. Scattering of light of this polarization is considered to be a major cause of reduced contrast. Efforts are continuously made to improve brightness and contrast by ultrafine particle formation and dispersion stabilization of pigments, but there is a limit to the degree of freedom in selecting coloring materials for realizing color coordinates for high color purity display devices. In addition, the pigment dispersion method using the developed coloring material, particularly, pigment, has reached a limit in improving color purity, brightness and contrast of the color filter using the same.

Accordingly, development of a novel coloring material capable of improving color reproduction, brightness, and contrast by improving color purity has been demanded.

Documents of the prior art

Patent document

Korean patent laid-open No. 2001 + 0009058

Disclosure of Invention

The present inventors provide a quinophthalone compound having a novel structure, a photosensitive resin composition comprising the same, a photosensitive material manufactured using the same, a color filter, and a display device comprising the same.

One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the chemical formula 1 described above,

at least one of R1 and R3 is represented by the following chemical formula 2 or chemical formula 3,

[ chemical formula 2]

[ chemical formula 3]

In the above-described chemical formulas 2 and 3,

represents a site linked to the above chemical formula 1,

x is O or NH,

l is a substituted or unsubstituted alkylene, substituted or unsubstituted heteroalkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene,

m is a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted heteroalkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, or a substituted or unsubstituted 2-valent nitrogen atom-containing dianhydride group,

r1 and R3 which are not R1 and R3, R2, R4, R41 and R42 of the above chemical formula 2 or chemical formula 3, are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a sulfonic acid group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group and a substituted or unsubstituted dianhydride group containing a nitrogen atom, adjacent groups may be bonded to each other to form a ring,

r is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group,

r1 and r3 are integers of 1 to 4, and when r1 and r3 are 2 or more, the structures in the brackets () are the same or different,

r4 is an integer of 0 to 4, and when R4 is 2 or more, R4 may be the same or different,

r2 is an integer of 0 to 2, R2 is 2, R2 may be the same as or different from each other,

when r41 and r42 are integers of 0 to 3 and r41 and r42 are 2 or more, the structures in the brackets () may be the same or different.

One embodiment of the present specification provides a photosensitive resin composition including the compound represented by chemical formula 1, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

One embodiment of the present specification provides a photosensitive material produced using the photosensitive resin composition.

One embodiment of the present specification provides a color filter including the photosensitive material.

One embodiment of the present specification provides a display device including the color filter.

The compound according to one embodiment of the present description can be used as a coloring material in a photosensitive resin composition, has excellent solubility in an organic solvent, and can reduce a dispersion step.

In addition, the quinophthalone compound represented by chemical formula 1 according to one embodiment of the present description is used as a coloring material, and thus color reproduction, brightness, and contrast can be improved.

Detailed Description

The present specification will be described in more detail below.

In the present specification, when a certain member is referred to as being "on" another member, it includes not only a case where the certain member is in contact with the another member but also a case where the other member is present between the two members.

In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.

According to an embodiment of the present specification, there is provided a compound represented by the above chemical formula 1.

One embodiment of the present specification includes the compound represented by the above chemical formula 1, thereby having excellent solubility to an organic solvent. Specifically, the solubility of chemical formula 1 is increased by including phthalimide (phthalamide) linked by an ester group (-COOR).

Bulky substituents prevent intermolecular aggregation, and solubility in solvents is further increased by free rotating substituents in the Chromophore. In particular, substituents such as phthalimide are often used as synergists (synergist) when dispersing pigments.

Since the solubility is increased, coagulation between the coloring materials can be prevented, thereby reducing the amount of material required for dispersion of the coloring materials, and thus enabling to improve the economy. In addition, improvement in contrast ratio (CR, contrast ratio) can be achieved, and excellent heat resistance can be achieved.

Examples of the substituent of the compound represented by the above chemical formula 1 will be described below, but the present invention is not limited thereto.

In the context of the present specification,

indicates a site to which another substituent or a binding moiety is attached.

In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; a carboxyl group; an imide group; an amide group; an anionic group; an alkoxy group; an alkyl group; a cycloalkyl group; an alkenyl group; a cycloalkenyl group; a sulfonate group; an amine group; an aryl group; a heteroaryl group; a silyl group; alkylsulfonyl (

Alkyl sulfo xy); arylsulfonyl (

Aryl sulfoxy); a boron group; c3An alkenoyl group; an acrylate group; an ether group; containing N, O, S or P atoms, and one or more anionic groups, or not having any substituent.

In the present specification, an "adjacent" group may represent a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, adjacent groups may be bonded to form a "ring", and the ring refers to an aromatic or aliphatic ring. Specifically, the ring may be an aromatic ring, and may be an aryl group or a heteroaryl group. The aryl and heteroaryl groups can be used as described below. The ring may be an aliphatic ring, and the aliphatic ring is not an aromatic ring.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

In the present specification, the carbonyl group may be represented by — COR ', and the R' may be hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. The carbon number of the carbonyl group is not particularly limited, but a carbonyl group having 1 to 30 carbon atoms is preferable. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, the ester group may be represented by-COOR ', and the R' may be hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group. In the above ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, with respect to the amide group, the nitrogen of the amide group may be 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, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the anionic group has a chemical bond with the structure of chemical formula 1, and the anionic group is not particularly limited, and, for example, anions described in U.S. Pat. No. 7,939,644, Japanese patent application laid-open No. 2006 + 003080, Japanese patent application laid-open No. 2006 + 001917, Japanese patent application laid-open No. 2005 + 159926, Japanese patent application laid-open No. 2007 + 7028897, Japanese patent application laid-open No. 2005 + 071680, Korean application laid-open No. 2007 + 7000693, Japanese patent application laid-open No. 2005 + 111696, Japanese patent application laid-open No. 2008 + 2014962463, and Japanese patent laid-open No. 199436 can be applied. Specific examples of the anionic group include trifluoromethanesulfonic acid anion, bis (trifluoromethylsulfonyl) amide anion, bis (trifluoromethylsulfonyl) imide anion, bisperfluoroethylsulfonylimide anion, tetraphenylborate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris (trifluoromethylsulfonyl) methide, SO₃ ^-、CO₂ ^-、SO₂N^-SO₂CF₃、SO₂N^-SO₂CF₂CF₃Halogen groups such as fluorine, iodine, chlorine, etc., but not limited thereto.

In the present specification, the anionic group may have an anion itself or may be present in a complex form together with other cations. Therefore, the sum of all charges of the molecules of the compound of the present invention may vary depending on the number of substituted anionic groups. Since the compound of the present invention has a cation on one amine group, the sum of all the charges of the molecule may have a value of 0 to 0 which is a value obtained by subtracting 1 from the number of substituted anionic groups.

In the present specification, the sulfonic acid group is-SO₃H。

In the present specification, the alkoxy group may be a linear or branched one, and the number of carbon atoms is not particularly limited, and may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, and is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl. In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and is particularly preferably a cyclopentyl group or a cyclohexyl group, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, and a cycloalkyl group having 3 to 60 carbon atoms is preferable, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

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, and is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 30. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. Specific examples of the alkenyl group include, but are not limited to, alkenyl groups substituted with an aryl group such as a stilbene group or a styrene group.

In the present specification, the cycloalkenyl group is not particularly limited, and a cycloalkenyl group having 3 to 60 carbon atoms is preferable, and according to one embodiment, the number of carbon atoms of the cycloalkenyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the above cycloalkenyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the above cycloalkenyl group is 3 to 6. Examples of the cycloalkenyl group include cyclopentenylene and cyclohexenylene, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, and is preferably an aryl group having 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 monocyclic aryl group may be, but is not limited to, phenyl, biphenyl, terphenyl, and the like. The polycyclic aromatic group may be a naphthyl group, an anthryl group, an indenyl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,

And a fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.

In the case where the above-mentioned fluorenyl group is substituted, it may be

Isospirofluorene group,

(9, 9-dimethylfluorenyl group) and

and substituted fluorenyl groups such as (9, 9-diphenylfluorenyl) and the like. But is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is 2 to 30, specifically 2 to 20. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridinyl, pyridazinyl, quinolyl, isoquinolyl, indolyl, carbazolyl, benzoquinoyl

Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuryl, dibenzofuryl and the like, but are not limited thereto.

In the present specification, the heteroaryl group may be any of the above-mentioned heterocyclic groups other than aromatic groups.

In the present specification, the silyl group may be represented by the formula of — SiY1Y2Y3, and each of Y1, Y2, and Y3 may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group (TMS), a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, examples of the alkylsulfonyl group include methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, and the like, but are not limited thereto. The alkyl group in the above alkylsulfonyl group can be applied to the above description about the alkyl group.

As the arylsulfonyl group in the present specification, there is a benzenesulfonyl group

P-toluenesulfonyl (p-

) And the like, but is not limited thereto. As the aryl group in the above arylsulfonyl group, the above-mentioned explanation about the aryl group can be applied.

In the present specification, the boron group may be represented BY the formula of-BY 4Y5, and each of Y4 and Y5 may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The boron group 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, an acryloyl group represents a photopolymerizable unsaturated group, and examples thereof include, but are not limited to, (meth) acryloyl groups.

In the present specification, the acrylate group represents a photopolymerizable unsaturated group, and examples thereof include, but are not limited to, (meth) acrylate groups.

In the present specification, "(meth) acryloyl group" means at least one selected from acryloyl groups and methacryloyl groups. The symbol "(meth) acrylate" has the same meaning.

In this specification, an ether group may be represented by — COR' ". The above R' "is a substituted or unsubstituted alkyl group. The above-mentioned alkyl group can be applied to the above-mentioned description about the alkyl group.

In the present specification, the sulfonate group may be an alkylsulfonate group, a cycloalkylsulfonate group, or an arylsulfonate group. The above description of the alkyl group can be applied to the "alkyl group", the above description of the cycloalkyl group can be applied to the "cycloalkyl group", and the above description of the aryl group can be applied to the "aryl group".

In the present specification, the sulfonate group may be represented by the following chemical formula S, but is not limited thereto.

[ chemical formula S ]

In the above chemical formula S, a is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

In the present specification, the amine group may be selected from-NH₂The number of carbon atoms of the alkylamino group, the N-alkylarylamino group, the arylamino group, the N-arylheteroarylamino group, the N-alkylheteroarylamino group, and the heteroarylamino group is not particularly limited, and is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, and an N-biphenylfluorenylamino group.

In the present specification, the number of carbon atoms of the dianhydride group containing a nitrogen atom is not particularly limited, and may be 4 to 30, specifically 4 to 20, and more specifically 4 to 15.

In the present specification, the dianhydride group containing the nitrogen atom may be represented by the following chemical formula N or chemical formula M, but is not limited thereto.

[ chemical formula N ]

[ chemical formula M ]

In the above chemical formula N and chemical formula M, B is-X-X ' -or-X ═ X ' -, and X ' are CR₁₁R₁₂，R₁₁、R₁₂The same or different from each other, each independently hydrogen, deuterium, N, or S, or adjacent groups may be bonded to each other to form a ring, and Z1 to Z3, the same or different from each other, each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a ring.

In the present specification, the substituted or unsubstituted 2-valent nitrogen atom-containing dianhydride group described above can be applied to the explanation of the nitrogen atom-containing dianhydride group described above, except that the group is a 2-valent group.

In the present specification, alkylene means that there are two binding sites on alkane (alkane). The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, and for example, the number of carbon atoms is 1 to 30, specifically 1 to 20, more specifically 1 to 10.

In the present specification, heteroalkylene means that there are two binding sites on an alkane (alkane) containing O, N or S as a heteroatom. The above-mentioned heteroalkylene group may be linear, branched or cyclic. The number of carbon atoms of the heteroalkylene group is not particularly limited, and for example, the number of carbon atoms is 2 to 30, specifically, 2 to 20, more specifically, 2 to 10.

In the present specification, arylene means a group having two binding sites on an aryl group, i.e., a valence of 2. The above description of the aryl groups applies except that they are each a 2-valent group.

In the present specification, heteroarylene means a group having two binding sites on heteroaryl, i.e., a valence of 2. The above description of heteroaryl groups can be applied, except that they are each a 2-valent group.

In one embodiment of the present specification, X is O or NH.

In one embodiment of the present specification, X is O.

In one embodiment of the present specification, X is NH.

In one embodiment of the present specification, L in chemical formula 1 may be a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroalkylene group having 2 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L in chemical formula 1 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroalkylene group having 2 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

In one embodiment of the present specification, L in chemical formula 1 is a substituted or unsubstituted, linear or branched alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L in chemical formula 1 is a substituted or unsubstituted, linear or branched alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L in chemical formula 1 is a substituted or unsubstituted, linear or branched alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L in chemical formula 1 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L in chemical formula 1 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L in chemical formula 1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L in the chemical formula 1 is a substituted or unsubstituted propylene group.

In one embodiment of the present specification, L in the chemical formula 1 is a propylene group.

In one embodiment of the present specification, M in chemical formula 1 is a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted heteroalkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, or a substituted or unsubstituted 2-valent nitrogen atom-containing dianhydride group.

In one embodiment of the present specification, M in chemical formula 1 is a 2-valent, substituted or unsubstituted, nitrogen atom-containing dianhydride group that is directly bonded to the compound.

In one embodiment of the present specification, M in the chemical formula 1 is a direct bond.

In one embodiment of the present specification, M in chemical formula 1 is a substituted or unsubstituted 2-valent dianhydride group containing a nitrogen atom.

In one embodiment of the present specification, M in chemical formula 1 is a dianhydro anhydride group containing a nitrogen atom and having a valence of 2.

In one embodiment of the present specification, M in the chemical formula 1 may be represented by the following chemical formula.

In one embodiment of the present specification, at least one of R1 and R3 in chemical formula 1 is represented by chemical formula 2 or chemical formula 3.

In one embodiment of the present specification, R1 in chemical formula 1 is represented by chemical formula 2 or chemical formula 3.

In one embodiment of the present specification, R1 in chemical formula 1 is represented by chemical formula 2.

In one embodiment of the present specification, R1 in chemical formula 1 is represented by chemical formula 3.

In one embodiment of the present specification, R1 of chemical formula 1 other than the chemical formula 2 or R1 of chemical formula 3 is selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a sulfonic acid group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, and adjacent R1 s may be bonded to each other to form a ring, the above R is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, in R1 of chemical formula 1, R1 other than chemical formula 2 or chemical formula 3 is hydrogen, a halogen group, a nitro group, a hydroxyl group, -COOR, or a substituted or unsubstituted alkyl group, or adjacent R1 may be bonded to each other to form a ring, and R is hydrogen or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, in R1 of chemical formula 1, R1 other than chemical formula 2 or chemical formula 3 is hydrogen, a halogen group, a nitro group, a hydroxyl group, -COOR, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or adjacent R1 may be bonded to each other to form an aromatic ring, and R is hydrogen or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, in R1 of chemical formula 1, R1 other than chemical formula 2 or chemical formula 3 is hydrogen, a halogen group, a nitro group, a hydroxyl group, -COOR, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or adjacent R1 may be bonded to each other to form an aromatic ring, and R is hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, in R1 of chemical formula 1, R1 other than chemical formula 2 or chemical formula 3 is hydrogen, a halogen group, a nitro group, a hydroxyl group, -COOR, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or adjacent R1 may be bonded to each other to form an aromatic ring, and R is hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, in R1 of chemical formula 1, R1 other than chemical formula 2 or chemical formula 3 is hydrogen, F, Cl, Br, nitro, hydroxyl, -COOR, or a substituted or unsubstituted tert-butyl group, or adjacent R1 may be bonded to each other to form a substituted or unsubstituted benzene ring, and R is hydrogen or a substituted or unsubstituted methyl group.

In one embodiment of the present specification, in R1 of chemical formula 1, R1 other than chemical formula 2 or chemical formula 3 is hydrogen, F, Cl, Br, nitro, hydroxy, -COOR, or tert-butyl, or adjacent R1 may be bonded to each other to form a benzene ring substituted or unsubstituted with a halogen group, nitro, or sulfonic acid group, and R is hydrogen or methyl.

In one embodiment of the present specification, in R1 of chemical formula 1, R1 other than chemical formula 2 or chemical formula 3 is hydrogen, F, Cl, Br, nitro, hydroxy, -COOR, or tert-butyl, or adjacent R1 may be bonded to each other to form a benzene ring substituted or unsubstituted with Br, nitro, or a sulfonic acid group, and R is hydrogen or methyl.

In one embodiment of the present specification, R2 is selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a sulfonic acid group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, and adjacent R2 may be bonded to each other to form a ring, and R is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R2 is hydrogen or deuterium.

In one embodiment of the present specification, R2 is hydrogen.

In one embodiment of the present specification, R3 in chemical formula 1 is represented by chemical formula 2 or chemical formula 3.

In one embodiment of the present specification, R3 in chemical formula 1 is represented by chemical formula 2.

In one embodiment of the present specification, R3 in chemical formula 1 is represented by chemical formula 3.

In one embodiment of the present specification, R3 of chemical formula 1 other than the chemical formula 2 or R3 of chemical formula 3 is selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a sulfonic acid group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, and adjacent R3 s may be bonded to each other to form a ring,

the above R is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R3 in R3 of chemical formula 1 other than chemical formula 2 or chemical formula 3 is hydrogen, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted aryl group, or a dianhydride group containing a nitrogen atom, or adjacent R3 may be bonded to each other to form a ring.

In one embodiment of the present specification, in R3 of chemical formula 1, R3 other than chemical formula 2 or chemical formula 3 is hydrogen, a substituted or unsubstituted arylsulfonate group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a dianhydride group containing a nitrogen atom, or adjacent R3 may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, R3 of the above chemical formula 1, which is not R3 of the above chemical formula 2 or 3, is hydrogen, a substituted or unsubstituted arylsulfonate group having 6 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a dianhydride group containing a nitrogen atom, or adjacent R3 may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, in R3 of chemical formula 1, R3 other than chemical formula 2 or chemical formula 3 is hydrogen, a substituted or unsubstituted arylsulfonate group having 6 to 10 carbon atoms, a phenyl group, or a dianhydride group containing a nitrogen atom, or adjacent R3 may be bonded to each other to form a benzene ring or a pyridine ring.

In one embodiment of the present specification, R3 in chemical formula 1 is not hydrogen in chemical formula 2 or R3 in chemical formula 3.

In one embodiment of the present specification, R3 of chemical formula 1 is not R3 of chemical formula 2 or chemical formula 3 and is a substituted or unsubstituted arylsulfonate group, and the substituted or unsubstituted arylsulfonate group may be represented by chemical formula S.

[ chemical formula S ]

In one embodiment of the present specification, a in the chemical formula S is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, a in the chemical formula S is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, a in the chemical formula S is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, a in the chemical formula S is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, a in the chemical formula S is phenyl or naphthyl.

In one embodiment of the present specification, the chemical formula S may be represented by any one of the following chemical formulae.

In one embodiment of the present specification, R3 of chemical formula 1 is not R3 of chemical formula 2 or chemical formula 3 and is a phenyl group.

In one embodiment of the present specification, R3 of chemical formula 1 other than chemical formula 2 or R3 of chemical formula 3 is a dianhydride group containing a nitrogen atom, and the dianhydride group containing a nitrogen atom may be represented by chemical formula N or chemical formula M.

[ chemical formula N ]

[ chemical formula M ]

In one embodiment of the present specification, B in the above chemical formula N is-X ' -or-X ═ X ' -, and X ' are CR₁₁R₁₂，R₁₁、R₁₂The same or different from each other, each independently hydrogen, deuterium, N, or S, or adjacent groups may be bonded to each other to form an aliphatic ring or an aromatic ring.

In one embodiment of the present specification, Z1 to Z3 in the above chemical formula M are the same or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, Z1 to Z3 in the above chemical formula M are the same or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, each of Z1 to Z3 in the above chemical formula M may be independently bonded to an adjacent group to form an aromatic ring.

In one embodiment of the present specification, Z1 and Z2 in the above chemical formula M may be bonded to each other to form an aromatic ring, and Z2 and Z3 may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, Z1 and Z2 of the above chemical formula M may be combined with each other to form a substituted or unsubstituted benzene ring, and Z2 and Z3 may be combined with each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, Z1 and Z2 of the above chemical formula M may be bonded to each other to form a benzene ring, and Z2 and Z3 may be bonded to each other to form a benzene ring.

In one embodiment of the present specification, the chemical formula N may be represented by any one of the following chemical formulae.

In the above chemical formulae, N1 to N18, which are the same or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, and adjacent groups may be bonded to each other to form a ring,

n1 is an integer of 0 to 4, n2 is an integer of 0 to 2, n3 is an integer of 0 to 4, n8 is an integer of 0 to 8, n9 is an integer of 0 to 4, n10 is an integer of 0 to 4, n11 is an integer of 0 to 2, n12 is an integer of 0 to 5, n13 is an integer of 0 to 2, n14 is an integer of 0 to 2, n15 is an integer of 0 to 4, n16 is an integer of 0 to 4, n17 is an integer of 0 to 3, n18 is an integer of 0 to 3,

when n1 to n18 are 2 or more, the structures in the brackets () may be the same or different.

In one embodiment of the present disclosure, N1 to N18 are hydrogen.

In one embodiment of the present specification, the chemical formula M may be represented by the following chemical formula M-1.

[ chemical formula M-1]

In the above chemical formula M-1, N19 and N20, which are the same as or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, and adjacent groups may be bonded to each other to form a ring,

n19 and n20 which are the same as or different from each other, are each independently an integer of 0 to 3, and when n19 and n20 are 2 or more, the structures in the brackets () are the same or different.

In one embodiment of the present specification, N19 and N20 in the above chemical formula M-1 are hydrogen.

In one embodiment of the present specification, R4 is selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, and adjacent groups may be bonded to each other to form a ring,

In one embodiment of the present specification, R4 represents hydrogen, or adjacent groups may be bonded to each other to form a ring.

In one embodiment of the present specification, R4 is hydrogen, or adjacent groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, R4 represents hydrogen, or adjacent groups may be bonded to each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, R4 represents hydrogen, or adjacent groups may be bonded to each other to form a benzene ring.

In one embodiment of the present specification, R41 and R42, which may be the same or different from each other, are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, -COR, -COOR, an imide group, an amide group, an anionic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, and adjacent groups may be bonded to each other to form a ring,

In one embodiment of the present specification, R41 and R42 are hydrogen.

In one embodiment of the present specification, r1 is an integer of 1 to 4.

In one embodiment of the present specification, r2 is an integer of 0 to 2.

In one embodiment of the present specification, r3 is an integer of 1 to 4.

In one embodiment of the present specification, r4 is an integer of 0 to 4.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following structure, the following structure represents an isomer of the chemical formula 1, and the chemical formula 1 represents a representative structure. Isomers refer to molecules of the same molecular formula but having different physical/chemical properties from each other.

In the above structure, R1 to R3 and R1 to R3 are the same as described above.

The description of the isomers can be applied to all chemical formulae described in the present specification.

According to another embodiment of the present disclosure, the chemical formula 1 may be represented by the following chemical formula 4 or chemical formula 5.

[ chemical formula 4]

[ chemical formula 5]

In the above-described chemical formulas 4 and 5,

r2 to R4, R41, R42, L, M, R2 to R4, R41 and R42 are the same as defined in the above chemical formula 1,

r5 is selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, nitro, hydroxyl, -COR, -COOR, an imide group, an amide group, an anionic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group,

r5 is an integer of 0 to 3, and when R5 is 2 or more, R5 may be the same as or different from each other.

In the present specification, R5 is hydrogen or deuterium.

In the present specification, R5 represents hydrogen.

According to another embodiment of the present disclosure, the chemical formula 1 may be represented by the following chemical formula 6 or chemical formula 7.

[ chemical formula 6]

[ chemical formula 7]

In the above chemical formula 6 and chemical formula 7,

r1, R2, R4, R41, R42, L, M, R1, R2, R4, R41 and R42 are the same as defined in the above chemical formula 1,

r6 is selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, nitro, hydroxyl, -COR, -COOR, an imide group, an amide group, an anionic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group,

r6 is an integer of 0 to 3, and when R6 is 2 or more, R6 may be the same as or different from each other.

In the present specification, R6 represents hydrogen or deuterium.

In the present specification, R6 represents hydrogen.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 4-1 or chemical formula 5-1.

[ chemical formula 4-1]

[ chemical formula 5-1]

In the above chemical formula 4-1 and chemical formula 5-1,

r2 to R5, R41, R42, L, M, R2 to R5, R41 and R42 are the same as defined in the above chemical formula 4 and chemical formula 5.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 6-1 or chemical formula 7-1.

[ chemical formula 6-1]

[ chemical formula 7-1]

In the above chemical formula 6-1 and chemical formula 7-1,

r1, R2, R4, R6, R41, R42, L, M, R1, R2, R4, R6, R41 and R42 are the same as defined in the above chemical formula 6 and chemical formula 7.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-1.

[ chemical formula 1-1]

In the above-mentioned chemical formula 1-1,

r1 to R3, R1 and R2 are the same as defined in the above chemical formula 1,

r31 is hydrogen, deuterium, a substituted or unsubstituted sulfonate group, or a substituted or unsubstituted dianydride group containing a nitrogen atom,

r3-1 is an integer of 0 to 3, and when R3-1 is 2 or more, R3 may be the same or different.

In R31 of the above chemical formula 1-1, the substituted or unsubstituted sulfonate group and the substituted or unsubstituted dianhydride group containing a nitrogen atom are the same as described above.

In one embodiment of the present specification, at least one of R3 is hydrogen and may be represented by the following chemical formula S, chemical formula N, or chemical formula M.

[ chemical formula S ]

[ chemical formula N ]

[ chemical formula M ]

In the above chemical formula S, chemical formula N and chemical formula M,

represents a site linked to the above chemical formula 1,

a is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group,

b is-X-X '-or-X ═ X' -,

x and X' are CR₁₁R₁₂，

R₁₁、R₁₂Are the same or different from each other and are each independently hydrogen, deuterium, N, or S, or adjacent groups are bonded to each other to form a ring,

z1 to Z3 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to each other to form a ring.

A, B and Z1 to Z3 in the above chemical formula S, chemical formula N and chemical formula M are the same as those described above.

According to another embodiment of the present disclosure, chemical formula 1 may be represented by any one of the following chemical formulae, but is not necessarily limited thereto.

In addition, one embodiment of the present specification provides a colorant composition including the compound represented by the above chemical formula 1.

The colorant composition may further include at least one of a dye and a pigment in addition to the compound of chemical formula 1. For example, the colorant composition may contain only the compound of the above chemical formula 1, but may contain the compound of the above chemical formula 1 and one or more dyes, or the compound of the above chemical formula 1 and one or more pigments, or the compound of the above chemical formula 1, one or more dyes, and one or more pigments.

One embodiment of the present specification provides a photosensitive resin composition containing the colorant composition.

One embodiment of the present specification provides a photosensitive resin composition comprising: a compound represented by the above chemical formula 1, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

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

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

The polyfunctional monomer for imparting mechanical strength to the film may be one or more selected from the group consisting of unsaturated carboxylic acid esters, aromatic vinyl compounds, unsaturated ethers, unsaturated imides, and acid anhydrides.

Specific examples of the unsaturated carboxylic acid ester include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (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, and mixtures thereof, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxyethyleneglycol (meth) acrylate, methoxytriethyleneglycol (meth) acrylate, methoxytripropyleneglycol (meth) acrylate, poly (ethyleneglycol) methyl ether (meth) acrylate, phenoxydiethyleneglycol (meth) acrylate, p-nonylphenoxypolyethyleneglycol (meth) acrylate, p-nonylphenoxypolypropyleneglycol (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 (alpha-hydroxymethyl) acrylate, methyl (meth) acrylate, n-butyl (meth) acrylate, n-nonylphenoxypolyethyleneglycol (meth) acrylate, n-nonylphenoxypolypropyleneglycol (meth) acrylate, p-nonylphenoxypolypropyleneglycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, and methyl (meth) acrylate, Ethyl (α -hydroxymethyl) acrylate, propyl (α -hydroxymethyl) acrylate, and butyl (α -hydroxymethyl) acrylate, but are not limited thereto.

Specific examples of the aromatic vinyl group include, but are not limited to, styrene, α -methylstyrene, (o, m, p) -vinyltoluenes, (o, m, p) -methoxystyrenes, and (o, m, p) -chlorostyrenes.

Specific examples of the unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.

Specific examples of the unsaturated imides include, but are not limited to, N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide.

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

The monomer for imparting alkali solubility is not particularly limited as long as it contains an acid group, and for example, one or more selected from (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleate, 5-norbornene-2-carboxylic acid, mono-2- ((meth) acryloyloxy) ethyl phthalate, mono-2- ((meth) acryloyloxy) ethyl succinate, and ω -carboxylic acid polycaprolactone mono (meth) acrylate are preferably used, but not limited thereto.

According to one embodiment of the present disclosure, the binder resin has an acid value of 50 to 130KOHmg and a weight average molecular weight of 1000 to 50000 g/mol.

The acid value of the binder resin can be measured by titration with a 0.1N potassium hydroxide (KOH) methanol solution.

In one embodiment of the present specification, the binder resin may be a copolymer (molar ratio 70:30) of benzyl methacrylate and methacrylic acid.

The polyfunctional monomer is a monomer that functions to form a resist image by light, and specifically may be one or a mixture of two or more selected from the group consisting of propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, tetraethylene glycol dimethacrylate, bisphenoxyethanol diacrylate, trihydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate.

In one embodiment of the present disclosure, the polyfunctional monomer may be DPHA (dipentaerythrityl hexaacrylate).

The photoinitiator is not particularly limited as long as it is an initiator that initiates crosslinking by photogeneration of a radical, and may be, for example, one or more selected from acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds.

Examples of the acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, and the like, but is not limited thereto.

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

The triazine compound includes 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 1,1,1,3,3, 3-hexafluoroisopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid ester, ethyl 2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid ester, 2-oxiranyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } ethanoic acid ester, cyclohexyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } ethanoic acid ester, Benzyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate, 3- { chloro-4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanamide, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) -1, 3-butadiene-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but is not limited thereto.

Examples of the oxime compounds include, but are not limited to, 1- (4-phenylthio) phenyl-1, 2-octanedione 2- (O-benzoyloxime) (CIBA-GEIGY Co., CGI 124), 1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -ethanone 1- (O-acetyloxime) (CGI 242), and N-1919(ADEKA Co.).

In one embodiment of the present specification, the photoinitiator may be I-369(BASF corporation).

The solvent can be acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1, 4-di

Alkane, ethylene 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-dichloroethane, 1,1, 1-trichloroethane, 1,1, 2-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanoneMore than one of cyclopentanone, propylene glycol monomethyl ether acetate, propylene glycol ethyl 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, but the present invention is not limited thereto.

In one embodiment of the present specification, the solvent may be propylene glycol monomethyl ether acetate.

One embodiment of the present disclosure provides a photosensitive resin composition, wherein the compound represented by chemical formula 1 is contained in an amount of 5 to 60 wt%, the binder resin is contained in an amount of 1 to 60 wt%, the photoinitiator is contained in an amount of 0.1 to 20 wt%, the polyfunctional monomer is contained in an amount of 0.1 to 50 wt%, the additive is contained in an amount of 0.1 to 10 wt%, and the solvent is contained in an amount of 10 to 80 wt%, based on the total weight of the photosensitive resin composition.

According to one embodiment of the present disclosure, the content of the compound represented by the chemical formula 1 is 5 to 60% by weight, the content of the binder resin is 1 to 60% by weight, the content of the photoinitiator is 0.1 to 20% by weight, and the content of the polyfunctional monomer is 0.1 to 50% by weight, based on the total weight of solid components in the photosensitive resin composition.

The total weight of the solid components is the sum of the total weight of the components other than the solvent in the photosensitive resin composition. The amount of the solid component or the weight% of the solid component of each component can be measured by a general analytical means used in the art such as liquid chromatography or gas chromatography.

According to an embodiment of the present disclosure, the photosensitive resin composition may further include an additive.

According to an embodiment of the present disclosure, the photosensitive resin composition may further include one or more additives selected from a photocrosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent.

According to one embodiment of the present specification, the content of the additive is 0.1 to 20% by weight based on the total weight of solid components in the photosensitive resin composition.

In one embodiment of the present specification, the additive may be a surfactant.

According to one embodiment of the present disclosure, the surfactant is contained in an amount of 0.1 wt% to 10 wt% based on the total weight of the photosensitive resin composition.

According to one embodiment of the present disclosure, the surfactant is contained in an amount of 0.1 to 10 wt% based on the total weight of solid components in the photosensitive resin composition.

As the photo-crosslinking sensitizer, a benzophenone-based compound selected from benzophenone, 4, 4-bis (dimethylamino) benzophenone, 4, 4-bis (diethylamino) benzophenone, 2,4, 6-trimethylaminobenzophenone, methylphthalylbenzoate, 3-dimethyl-4-methoxybenzophenone, 3,4, 4-tetrakis (t-butylperoxycarbonyl) benzophenone and the like; fluorenone compounds such as 9-fluorenone, 2-chloro-9-fluorenone, and 2-methyl-9-fluorenone; thioxanthone compounds such as thioxanthone, 2, 4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone and diisopropylthioxanthone; xanthone-based compounds such as xanthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tert-butylanthraquinone, and 2, 6-dichloro-9, 10-anthraquinone; acridine compounds such as 9-phenylacridine, 1, 7-bis (9-acridinyl) heptane, 1, 5-bis (9-acridinylpentane), 1, 3-bis (9-acridinyl) propane and the like; dicarbonyl compounds such as benzil, 1,7, 7-trimethyl-bicyclo [2,2,1] heptane-2, 3-dione, and 9, 10-phenanthrenequinone; phosphine oxide compounds such as 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethylpentylphosphine oxide; benzoate-based compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, and 2-n-butoxyethyl-4- (dimethylamino) benzoate; amino synergists such as 2, 5-bis (4-diethylaminobenzylidene) cyclopentanone, 2, 6-bis (4-diethylaminobenzylidene) cyclohexanone, and 2, 6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone; coumarin-based compounds such as 3, 3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, and 10, 10-carbonylbis [1,1,7, 7-tetramethyl-2, 3,6, 7-tetrahydro-1H, 5H,11H-C1] -benzopyran [6,7,8-ij ] -quinolizin-11-one; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; more than one of 2-benzoyl methylene and 3-methyl-b-naphthothiazoline.

The above-mentioned curing accelerator is used for curing and improving mechanical strength, and specifically, it is possible to use a curing accelerator selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, and 2-mercaptobenzothiazole

One or more of oxazole, 2, 5-dimercapto-1, 3, 4-thiadiazole, 2-mercapto-4, 6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate).

As the adhesion promoter used in the present specification, one or more species selected from methacryloxysilane coupling agents such as methacryloxypropyltrimethoxysilane, methacryloxypropyldimethoxysilane, methacryloxypropyltriethoxysilane, and methacryloxypropyldimethoxysilane can be used, and as the alkyltrimethoxysilane, one or more species selected from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like can be used.

The surfactant is a silicon surfactant or a fluorine surfactant, and specifically, BYK-077, BYK-085, BYK-300, BYK-301, 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-375, BYK-380, BYK-390, etc. of BYK-Chemicals, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-177, BYK-390, etc. of BYK-Chemicals, etc. of BYK-177, etc. can be used as the fluorine surfactant, DIC (DaiNippon & Chemicals) can be used, 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, and the like, but are not limited thereto.

In one embodiment of the present specification, the surfactant may be F-475 available from DIC corporation.

The antioxidant may be at least one selected from Hindered phenol (Hindered phenol) antioxidants, amine antioxidants, sulfur antioxidants, and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate and triethyl phosphate; such as 2, 6-di-tert-butyl-p-cresol, octadecyl-3- (4-hydroxy-3, 5-di-tert-butylphenyl) propionate, tetrakis [ methylene-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] methane, 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene, diethyl 3, 5-di-tert-butyl-4-hydroxybenzylphosphite, 2-thiobis (4-methyl-6-tert-butylphenol), 2,6-g, t-butylphenol 4,4 '-butylidene-bis (3-methyl-6-tert-butylphenol), 4' -thiobis (3-methyl-6-tert-butylphenol) or bis [3 ", hindered phenol (Hindered phenol) primary antioxidants such as 3-Bis- (4'-hydroxy-3' -t-butylphenyl) butanoic acid ethylene glycol ester (Bis [3,3-Bis- (4'-hydroxy-3' -tert-butyl-phenyl) butanoic acid ] glycol ester); amine-based auxiliary antioxidants such as phenyl- α -naphthylamine, phenyl- β -naphthylamine, N '-diphenyl-p-phenylenediamine or N, N' -di- β -naphthyl-p-phenylenediamine; a sulfur-based auxiliary antioxidant such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethylthiuram disulfide tetrakis [ methylene-3- (laurylthio) propionate ] methane; or phosphite-based auxiliary antioxidants such as triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, Bis (2, 4-dibutylphenyl) Pentaerythritol diphosphite (Bis (2, 4-dittouylphenyl) Pentaerythritol diphophite) or tetrakis [2,4-Bis (1, 1-dimethylethyl) phenyl ] 1,1' -diyl diphosphonite ((1,1' -Biphenyl) -4,4' -diylbisphosphanous acid tetrakis [2,4-Bis (1, 1-dimethyethyl) phenyl ] ester).

Examples of the ultraviolet absorber include 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone, but the ultraviolet absorber is not limited thereto and any ultraviolet absorber generally used in this field can be used.

The thermal polymerization inhibitor may include, for example, at least one selected from the group consisting of p-anisole, hydroquinone, catechol (pyrocatechol), t-butylcatechol (t-butyl catechol), N-nitrosophenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4-thiobis (3-methyl-6-t-butylphenol), 2-methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine (phenothiazine), but is not limited thereto, and may include a thermal polymerization inhibitor generally known in the art.

The dispersant may be used by a method of internally adding the dispersant to the pigment in a form in which the pigment is surface-treated in advance, or a method of externally adding the dispersant to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant can be used, and examples thereof include fluorine type, ester type, cationic type, anionic type, nonionic type, amphoteric surfactant and the like. These may be used individually or in combination of two or more.

Specifically, the dispersant is at least one selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, alkylamide alkylene oxide adducts, and alkylamines, but is not limited thereto.

The leveling agent may be a polymerizable leveling agent or a non-polymerizable leveling agent. Specific examples of the polymerizable leveling agent include polyethyleneimine, polyamidoamine, and a reaction product of an amine and an epoxide, and specific examples of the non-polymerizable leveling agent include a non-polymeric sulfur-containing compound and a non-polymeric nitrogen-containing compound, but the non-polymerizable leveling agent is not limited thereto, and leveling agents generally used in this field can be used.

More specifically, the photosensitive resin composition of the present specification can be applied to a substrate by an appropriate method and cured to produce a photosensitive material in the form of a film or a pattern.

The coating method is not particularly limited, and a spray coating method, a roll coating method, a spin coating method, and the like can be used, and a spin coating method is generally widely used. After the coating film is formed, the residual solvent may be partially removed under reduced pressure according to circumstances.

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

The photosensitive resin composition according to the present specification can be used for a pigment dispersion type photosensitive material for manufacturing a color filter of a thin film transistor liquid crystal display device (TFT LCD), a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display device (TFT LCD) or an organic light emitting diode, a photosensitive material for forming an overcoat layer, a photosensitive material for a column spacer, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printed wiring board, a photosensitive material for a Plasma Display Panel (PDP), and the like, but the use thereof is not particularly limited.

The color filter may be manufactured using a photosensitive resin composition including the compound represented by chemical formula 1. The photosensitive resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to produce a photosensitive material, and a color filter including the photosensitive material can be provided.

The photosensitive resin composition according to one embodiment of the present description has excellent heat resistance and little color change due to heat treatment, and thus can provide a color filter having high color reproducibility and high brightness and contrast even after a curing process is performed in the production of the color filter.

The substrate may be a glass plate, a silicon wafer, a plastic-based plate such as Polyethersulfone (PES) or Polycarbonate (PC), or the like, and the type thereof is not particularly limited.

Specifically, the photosensitive resin composition according to one embodiment of the present specification may be applied to glass (5 × 5 cm)²) Spin coating (spinning) was performed thereon, and a prebaking treatment (prebake) was performed at 100 ℃ for 100 seconds to form a film. The distance between the substrate on which the film was formed and a photomask (photo mask) was set to 250 μm, and the entire surface of the substrate was exposed to 40mJ/cm by an exposure machine²The exposure amount of (2) is used for irradiation. Then, the exposed substrate was developed in a developer (potassium hydroxide (KOH), 0.05%) for 60 seconds and post-baked (postbake) at 230 ℃ for 20 minutes to fabricate a substrate.

The heat resistance evaluation can be measured by the method described later. The substrate manufactured in the above-described embodiment was subjected to a transmittance in the visible light region in the range of 380nm to 780nm by a spectrometer. In addition, the pre-bake treated (prebake) substrate was further post-baked (postbake) at 230 ℃ for 20 minutes, and a transmittance spectrum was obtained in the same apparatus and measurement range.

The spectrometer may be a spectrometer manufactured by MCPD-Otsuka, but is not limited thereto.

Using the transmittance spectrum and C light source obtained above, the backlight was used, and the obtained value E (L, a, b) was used to calculate the color change (hereinafter referred to as Δ Eab). A small value of Δ Eab means excellent color heat resistance. When the pigment has a value of Δ Eab <3, the pigment is useful as a color filter pigment and is excellent in heat resistance. Specifically, the equation for calculating Δ Eab is as follows.

[ calculation formula 1]

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

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

According to another embodiment, the color filter may further include an overcoat layer.

For the purpose of improving contrast, a lattice-like black pattern called a black matrix may be arranged between the color pixels of the color filter. As a material of the black matrix, chromium may be used. In this case, a method of forming a pattern by depositing chromium on the entire glass substrate and performing etching treatment may be used. However, in consideration of high process costs, high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix obtained by a pigment dispersion method capable of microfabrication may be used.

The black matrix may use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone or carbon black and a coloring pigment may be used in combination, and in this case, since the coloring pigment having insufficient light-shielding property is mixed, there is an advantage that even if the amount of the coloring material is relatively increased, the strength of the film and the adhesion to the substrate are not decreased.

The Display device may be any one of a Plasma Display Panel (PDP), a Light Emitting Diode (LED), an Organic Light Emitting element (OLED), a Liquid Crystal Display (LCD), a Thin FIlm Transistor-Liquid Crystal Display (LCD-TFT), and a Cathode Ray Tube (CRT).

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present description may be modified into other various forms, and the scope of the present description should not be construed as being limited to the embodiments described below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.

< example >

< Synthesis example of colorant Compound >

Synthesis example 1: synthesis of Compound 1

A100 ml two-necked Round Bottom Flask (RBF, Round Bottom flash) was charged with 25g of methyl benzoate (Methylbenzoate) and 2g (12.642mmol) of A-1, 1.873g (12.642mmol) of B-1 and stirred. Specifically, the reaction was carried out at 180 ℃ for 12 hours.

Then, 2.429g (12.642mmol) of D-1 was added, and the reaction was further carried out at 180 ℃ for 12 hours. The reaction was cooled to ambient temperature and precipitated into 250g of methanol (MeOH). After stirring for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ℃ to obtain compound 1, which was subjected to the next reaction without further isolation.

To a 250ml two-necked Round Bottom Flask (RBF, Round Bottom flash) was added 80g of Dimethylformamide (DMF), 5g (10.813mmol) of intermediate 1, 2.725g (30.439mmol) of sodium bicarbonate (NaHCO)₃) Then, the temperature was increased to 50 ℃ and the mixture was stirred to prepare a reaction solution.

Then, 2.899g (10.813mmol) of E-1 was slowly added to the above reaction solution, followed by stirring at 120 ℃ for 4 hours. Then, the reaction solution was cooled to normal temperature, and precipitated in 1800ml of distilled Water (deionized Water (DI-Water)). After precipitation, the precipitate was filtered under reduced pressure and washed with water. The precipitate was dried under reduced pressure. 5.2g (8.010mmol) of Compound 1 are obtained.

Ionization mode APCI +: M/z 650[ M + H ], Exact Mass (Exact Mass): 649

Synthesis example 2: synthesis of Compound 2

After 100ml of 6M hydrochloric acid (HCl) was added to a 250ml two-necked Round Flask (RBF, Round Bottom flash), 9.135g (66.61mmol) of A-2 was further added thereto, the temperature was raised to 100 ℃ and the mixture was stirred for 30 minutes, thereby preparing a reaction solution 1. Then, 9.34g (133.21mmol) of A-3 was slowly added to the above reaction solution 1.

Then, the mixture was further stirred at 100 ℃ for 2 hours. Then, the reaction solution was cooled to normal temperature, and the precipitate was filtered under reduced pressure. The precipitate was recrystallized in 250ml of ethanol (EtOH). Then, the mixture was filtered under reduced pressure to obtain 7.3g (38.995mmol) of A-4.

Then, 25g of methyl benzoate (Methylenzoate), 2.366g (12.642mmol) of A-4, 1.873g (12.642mmol) of B-1 were added and stirred. Specifically, the reaction solution 2 was prepared by reacting at 180 ℃ for 12 hours.

Then, the reaction solution 2 was cooled to normal temperature, and precipitated in 250g of MeOH. After stirring for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ℃ to obtain intermediate 2, which was subjected to the next reaction without further isolation.

Into a 250ml two-necked Round Bottom Flask (RBF, Round Bottom flash) was added 80g of Dimethylformamide (DMF), 3.431g (10.813mmol) of intermediate 2, 2.725g (30.439mmol) of sodium bicarbonate (NaHCO)₃) Then, the temperature was raised to 50 ℃ and stirred, thereby producing a reaction solution 3.

Then, 2.899g (10.813mmol) of E-1 was slowly added to the reaction solution 3, and stirred at 120 ℃ for 4 hours. The stirred solution was cooled to normal temperature and precipitated in 1800ml of distilled Water (DI-Water). The precipitate was filtered under reduced pressure, washed with water, and dried under reduced pressure to obtain 3.577g (7.090mmol) of compound 2.

Ionization mode APCI +: M/z ═ 505[ M + H ], accurate mass: 504

Synthesis example 3: synthesis of Compound 3

25g of methyl benzoate (Methylbenzoate), 2.366g (12.642mmol) of A-5, 1.873g (12.642mmol) of B-1 were added and stirred. The reaction was carried out at 180 ℃ for 12 hours to prepare a reaction solution 1.

Then, the reaction solution 1 was cooled to normal temperature, and precipitated in 250g of methanol (MeOH). After stirring for 30 minutes, the precipitate was filtered under reduced pressure and dried in a vacuum oven at 80 ℃ to obtain intermediate 2, which was subjected to the next reaction without further isolation.

Into a 250ml two-necked Round Bottom Flask (RBF, Round Bottom flash) was added 80g of Dimethylformamide (DMF), 3.431g (10.813mmol) of intermediate 3 and 2.725g (30.439mmol) of sodium bicarbonate (NaHCO)₃) Then, the temperature was raised to 50 ℃ and stirred, thereby producing a reaction solution 2.

Then, 2.899g (10.813mmol) of E-1 was slowly added to the above reaction solution 2, and stirred at 120 ℃ for 4 hours. After stirring, it was cooled to normal temperature (25 ℃ C.) and precipitated in 1800ml of distilled Water (DI-Water). The precipitate was filtered under reduced pressure and washed with water. The precipitate was dried under reduced pressure to obtain 3.592g (7.120mmol) of Compound 3.

Ionization mode APCI +: M/z ═ 505[ M + H ], accurate mass: 504

Synthesis example 4: synthesis of Compound 4

In a 100ml two-necked Round Bottom Flask (RBF, Round Bottom flash), 25g of methyl benzoate (Methylbenzoate) and 2.443g (12.642mmol) of A-6, 2.429g (12.642mmol 2.642mmol) of D-1 were added and stirred at 180 ℃ for 12 hours.

The reaction was cooled to ambient temperature and precipitated into 250g of methanol (MeOH). After stirring for 30 minutes, the precipitate was filtered under reduced pressure and dried in an 80-degree vacuum oven to obtain compound 4, which was subjected to the next reaction without further isolation.

To a 250ml two-necked Round Bottom Flask (RBF, Round Bottom flash) were added 80g of Dimethylformamide (DMF), 3.972g (10.813mmol) of intermediate 4, 2.725g (30.439mmol) of sodium bicarbonate (NaHCO)₃) The temperature was raised to 50 ℃ and stirred.

Then, 2.899g (10.813mmol) of E-1 was slowly added to the reaction solution, and stirred at 120 ℃ for 4 hours. The reaction solution was cooled to normal temperature, and precipitated in 1800ml of distilled Water (deionized Water). The precipitate was filtered under reduced pressure, washed with water, and dried under reduced pressure to obtain 5.127g (9.245mmol) of compound 4.

Ionization mode APCI +: M/z 555[ M + H ], accurate mass: 554

Synthesis example 5: synthesis of Compound 5

In synthesis example 4, compound 5 was synthesized in the same manner as intermediate 4 was changed to intermediate 5.

Ionization mode APCI +: M/z 700[ M + H ], accurate mass: 699

Synthesis example 6: synthesis of Compound 6

In synthesis example 4, compound 6 was synthesized in the same manner as intermediate 6 instead of intermediate 4.

Ionization mode APCI +: M/z ═ 600[ M + H ], accurate mass: 599

Synthesis example 7: synthesis of Compound 7

In synthesis example 4, compound 7 was synthesized in the same manner as intermediate 4 was changed to intermediate 7.

Ionization mode APCI +: M/z 556[ M + H ], accurate mass: 555

Synthesis example 8: synthesis of Compound 8

In synthesis example 4, compound 8 was synthesized in the same manner as intermediate 4 was changed to intermediate 8.

Ionization mode APCI +: M/z-654 [ M + H ], accurate mass: 653

Synthesis example 9: synthesis of Compound 9

In synthesis example 4, compound 9 was synthesized in the same manner as intermediate 4 was changed to intermediate 9.

Ionization mode APCI +: M/z-654 [ M + H ], accurate mass: 653

Synthesis example 10: synthesis of Compound 10

In synthesis example 4, compound 10 was synthesized in the same manner as intermediate 10 instead of intermediate 4.

Ionization mode APCI +: M/z ═ 700[ M + H ], accurate mass: 699

Synthesis example 11: synthesis of Compound 11

In synthesis example 4, compound 11 was synthesized in the same manner as intermediate 4 was changed to intermediate 11.

Ionization mode APCI +: M/z ═ 651[ M + H ], exact mass: 650

Synthesis example 12: synthesis of Compound 12

In synthesis example 4, compound 12 was synthesized in the same manner as intermediate 4 was changed to intermediate 12.

Ionization mode APCI +: M/z 711[ M + H ], accurate mass: 710

Synthesis examples 13 to 24: synthesis of Compounds 13 to 24

Intermediates 1 to 12 were used in place of E-1 to change the reaction conditions to

Compounds 13 to 24 were synthesized by the same method.

Compound 13: ionization mode APCI +: M/z ═ 700[ M + H ], accurate mass: 699

Compound 14: ionization mode APCI +: M/z 555[ M + H ], accurate mass: 554

Compound 15: ionization mode APCI +: M/z 555[ M + H ], accurate mass: 554

Compound 16: ionization mode APCI +: M/z 605[ M + H ], accurate mass: 604

Compound 17: ionization mode APCI +: M/z ═ 750[ M + H ], exact mass: 749

Compound 18: ionization mode APCI +: M/z ═ 650[ M + H ], accurate mass: 649

Compound 19: ionization mode APCI +: M/z 606[ M + H ], exact mass: 605

Compound 20: ionization mode APCI +: M/z ═ 704[ M + H ], accurate mass: 703

Compound 21: ionization mode APCI +: M/z ═ 704[ M + H ], accurate mass: 703

Compound 22: ionization mode APCI +: M/z 750[ M + H ], accurate mass: 749

Compound 23: ionization mode APCI +: M/z 701[ M + H ], exact mass: 700

Compound 24: ionization mode APCI +: M/z 761[ M + H ], accurate mass: 760

Comparative example Compound

A colorant (PY138) of the following structural formula was purchased from BASF to be used as a comparative example compound.

< example for producing photosensitive resin composition >

Example 1

5.554g of compound 1, a copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70:30, acid value 113KOH mg/g, weight average molecular weight 20000g/mol measured by Gel Permeation Chromatography (GPC)), molecular weight distribution (PDI)2.0g, solid content (S.C) 25%, 10.376g of Propylene Glycol Monomethyl Ether Acetate (PGMEA) as a solvent, I-369(BASF corporation) 2.018g as a photoinitiator, DPHA (Japanese chemical drug) 12.443g as a photopolymerizable compound of a polyfunctional monomer, PGMEA (Propylene glycol monomethyl ether acetate) 68.593g as a solvent, and F-475 (DIC corporation) as an additive, 1.016g as a surfactant, were mixed to prepare the photosensitive resin composition of example 1.

Examples 2 to 24

Photosensitive resin compositions of examples 2 to 24 were produced in the same composition as the photosensitive resin composition of example 1, except that the compound 1 was changed to compounds 2 to 24 in example 1.

Comparative example

5.554g of the comparative compound PY138, a copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70:30, acid value 113KOH mg/g, weight average molecular weight 20000g/mol as measured by Gel Permeation Chromatography (GPC), molecular weight distribution (PDI)2.0g, solid content (S.C) 25%, including Propylene Glycol Monomethyl Ether Acetate (PGMEA) 10.376g as a solvent, I-369(BASF corporation) 2.018g as a photoinitiator, DPHA (Japanese chemical drug) 12.443g as a photopolymerizable compound as a polyfunctional monomer, PGMEA (Propylene glycol monomethyl ether acetate) 68.593g as a solvent, and F-475 of DIC corporation of 1.016g as an additive d were mixed to produce the photosensitive resin composition of the comparative example.

< Experimental example >

Evaluation of solubility

The solubility of each of the compounds 1 to 24 and the comparative compound (PY138) in 100g of DimethylFormamide (DMF) was measured at 25 ℃ and 1 atmosphere, and the results are shown in table 1 below. The case where the solubility was 1% or more was represented as O, and the case where the solubility was less than 1% was represented as X.

[ Table 1]

Distinguishing	Solubility in water
		Compounds 1 to 24	O
Comparative example Compound (PY138)	X

Referring to table 1 above, the colorants of the compounds 1 to 24 of the present invention were superior in solubility in an organic solvent (dimethylformamide) to the comparative compound (PY 138).

In general, in the case of pigments, the pigments are not dissolved in an organic solvent and need to be dispersed by a derivative, a dispersant or the like. However, when dissolved in an organic solvent like in examples 1 to 24 according to the present specification, a derivative or a dispersant is not required or the amount used can be reduced, and thus, it can be easily applied commercially.

Substrate fabrication

The photosensitive resin compositions of examples 1 to 24 were used for the production of substrates, respectively. Specifically, the photosensitive resin compositions of examples 1 to 24 were coated on glass (5X 5 cm)²) Spin coating (spin coating) was performed thereon, and a prebaking treatment (prebake) was performed at 100 ℃ for 100 seconds to form a film.

The distance between the substrate on which the film was formed and a photomask (photo mask) was set to 250 μm, and the entire surface of the substrate was exposed to 40mJ/cm by an exposure machine²The exposure amount of (2) is used for irradiation.

Then, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and subjected to post-baking treatment (postbake) at 230 ℃ for 20 minutes to fabricate a substrate.

Evaluation of Heat resistance

The substrate produced by the above-described substrate production method was used to obtain a transmittance spectrum in the visible light region in the range of 380nm to 780nm by a spectrometer (MCPD-Otsuka). In addition, the pre-bake treated (prebake) substrate was further post-baked (postbake) at 230 ℃ for 20 minutes, and a transmittance spectrum was obtained in the same apparatus and measurement range.

Using the obtained transmittance spectrum and C light source backlight, and using the obtained values E (L, a, b), the color change (hereinafter referred to as Δ Eab) was calculated by the following formula 1 and shown in the following table 2.

A small value of Δ Eab means excellent color heat resistance.

When the pigment has a value of Δ Eab <3, the pigment is useful as a color filter pigment and is excellent in heat resistance.

[ formula 1]

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

[ Table 2]

Referring to table 2 above, it was confirmed that the difference (Δ Eab) between the transmittance spectra after the post-baking treatment and the post-baking treatment of the color pattern substrates formed using the photosensitive resin compositions of examples 1 to 24 of the present invention was less than 3, the color stability was high, and Δ Eab was very small and the heat resistance was excellent.

Claims

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the metal oxide is represented by,

chemical formula 2

Chemical formula 3

In the chemical formulas 2 and 3,

is represented by the formula 1 toThe part of the connection part is provided with a connecting part,

x is O, and the compound is,

l is an alkylene group having 1 to 20 carbon atoms,

m is a direct bond or

When R1 is not the chemical formula 2 or chemical formula 3, each is independently selected from hydrogen, deuterium, a halogen group, an alkyl group having 1 to 20 carbon atoms, a sulfonate group represented by the following chemical formula S, and a nitrogen atom-containing dianhydride group represented by the following chemical formula N having 4 to 15 carbon atoms, or adjacent R1 are bonded to each other to form a benzene ring or a pyridine ring,

r3 is an integer of 1 to 2,

when R3 is not the chemical formula 2 or 3 and R3 is 1, it is selected from a sulfonate group represented by the following chemical formula S, and a nitrogen atom-containing dianhydride group represented by the following chemical formula N having 4 to 15 carbon atoms,

when R3 is not the chemical formula 2 or chemical formula 3 and R3 is 2, adjacent R3 are combined with each other to form a benzene ring or a pyridine ring,

r2, R4, R41 and R42, equal to or different from each other, are each independently selected from hydrogen, deuterium or halogen groups,

r1 is an integer of 1 to 4, and when r1 is 2 or more, the structures in parentheses are the same or different,

r2 is an integer of 0 to 2, and when R2 is 2, R2 are the same as or different from each other,

r41 and r42 are integers of 0 to 3, and when r41 and r42 are 2 or more, the structures in parentheses are the same or different:

chemical formula S

Chemical formula N

In the chemical formulas S and N,

represents a site linked to the chemical formula 1,

a is a phenyl group or a naphthyl group,

b is-X-X '-or-X ═ X' -,

x and X' are CR₁₁R₁₂，

R₁₁And R₁₂The same or different from each other, each independently hydrogen, or adjacent groups are bonded to each other to form a benzene ring, a naphthalene ring, a pyridine ring, a cycloalkyl ring having 3 to 6 carbon atoms or a cycloalkenyl ring having 3 to 6 carbon atoms.

2. The compound according to claim 1, wherein the chemical formula 1 is a compound represented by the following chemical formula 4 or chemical formula 5:

chemical formula 4

Chemical formula 5

In the chemical formulas 4 and 5,

r2 to R4, R41, R42, L, M, R2 to R4, R41 and R42 are the same as defined in said chemical formula 1,

r5 is selected from the group consisting of hydrogen, deuterium and halogen,

3. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 6 or chemical formula 7:

chemical formula 6

Chemical formula 7

In the chemical formulas 6 and 7,

r1, R2, R4, R41, R42, L, M, R1, R2, R4, R41 and R42 are the same as defined in said chemical formula 1,

r6 is selected from the group consisting of hydrogen, deuterium and halogen,

r6 is 0.

4. The compound according to claim 2, wherein the chemical formula 1 is represented by the following chemical formula 4-1 or chemical formula 5-1:

chemical formula 4-1

Chemical formula 5-1

In the chemical formula 4-1 and the chemical formula 5-1,

r2 to R5, R41, R42, L, M, R2 to R5, R41 and R42 are the same as defined in said chemical formulae 4 and 5.

5. The compound according to claim 3, wherein the chemical formula 1 is represented by the following chemical formula 6-1 or chemical formula 7-1:

chemical formula 6-1

Chemical formula 7-1

In the chemical formula 6-1 and the chemical formula 7-1,

r1, R2, R4, R6, R41, R42, L, M, R1, R2, R4, R6, R41 and R42 are the same as defined in said chemical formula 6 and chemical formula 7.

6. The compound of claim 1, wherein R3 is a group represented by formula S, or formula N:

chemical formula S

Chemical formula N

In the chemical formulas S and N,

represents a site linked to the chemical formula 1,

a is a phenyl group, and the compound has the structure of,

b is-X-X '-or-X ═ X' -,

x and X' are CR₁₁R₁₂，

R₁₁And R₁₂The same or different from each other, each independently hydrogen, or adjacent groups are bonded to each other to form a benzene ring, a naphthalene ring or a pyridine ring.

7. A compound represented by any one of the following formulae:

8. a photosensitive resin composition comprising: the compound according to any one of claims 1 to 7, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

9. The photosensitive resin composition according to claim 8, wherein the content of the compound represented by the chemical formula 1 is 5 to 60% by weight based on the total weight of solid components in the photosensitive resin composition,

the content of the binder resin is 1 to 60% by weight,

the photoinitiator is present in an amount of 0.1 to 20 wt%,

the content of the polyfunctional monomer is 0.1 to 50% by weight.

10. The photosensitive resin composition according to claim 8, further comprising an additive.

11. A photosensitive material produced by using the photosensitive resin composition according to claim 8.

12. A color filter comprising the photosensitive material of claim 11.

13. A display device comprising the color filter of claim 12.