JP6485502B2 - Photosensitive resin composition and color filter containing the same - Google Patents

Description

  The present specification relates to a photosensitive resin composition and a color filter including the same.

  In recent years, color filters are required to have performance characterized by high brightness and high contrast ratio. One of the main purposes in the development of display elements is to differentiate display element performance by improving color purity and to improve productivity in the manufacturing process.

  Pigment types that have been used as color materials for color filters in the past exist in color photoresists in a particle-dispersed state, making it difficult to adjust the brightness and contrast ratio by adjusting the size and distribution of pigment particles. . In the case of pigment particles, multiple scattering of light caused by large particles aggregated in the color filter and inferior in solubility and dispersibility is caused. Such scattering of polarized light has been pointed out as a main factor for reducing the contrast ratio. Efforts are being made to improve the brightness and contrast ratio by making the pigments ultra fine and dispersion stable, but there is a degree of freedom in selecting color materials to achieve color coordinates for display devices with high color purity. Limited. In addition, color materials that have already been developed, particularly pigment dispersion methods using pigments, have reached the limit in improving the color purity, luminance, and contrast ratio of color filters using the color materials. Therefore, development of a color material that can improve color purity and improve color reproduction, luminance, and contrast ratio, or a photosensitive resin composition containing the same is demanded.

JP-A-9-87534

  The present invention relates to a photosensitive resin composition and a color filter produced using the same.

One embodiment of the present invention provides a photosensitive resin composition comprising a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2.
[Chemical Formula 1]
[Chemical formula 2]
In Formula 1,
L _A and L _B may be the same or different from each other, and each independently represents a direct bond; or an alkylene group having 1 to 10 carbon atoms,
R _{A to} R _F may be the same or different from each other, and each independently represents hydrogen; deuterium; halogen atom; nitro group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl having 1 to 30 carbon atoms; Selected from the group consisting of:
R _{1 to} R ₆ may be the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen atom; a substituted or unsubstituted C 1-6 linear or branched alkyl group; Selected from the group consisting of a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms; a sulfonic acid group; a sulfonic acid ester group; a sulfonic acid group; a —SO ₂ NHR ₇ group; and —SO ₂ NR ₈ R ₉ ;
R _{7 to} R ₉ may be the same as or different from each other, and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms,
X _{1 to} X ₅ may be the same as or different from each other, and each independently represents hydrogen; deuterium; an anionic group; a hydroxy group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Selected from the group consisting of a substituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms;
At least one of the X _{1 to} X ₅ is an anionic group;
R _AA and R _BB may be the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon group having 1 to 30 carbon atoms. A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms; a halogen atom; a nitro group ; phenoxy group; a carboxy group; a carboxylic acid ester group; carboxylate; alkoxycarbonyl group; a hydroxyl group; a sulfonic acid group; a sulfonic acid ester group; _sulfonate; -SO 2 _NHR'; and _-SO 2 NR Selected from the group consisting of
a and b may be the same or different from each other, and each independently represents an integer of 0 to 4;
when a and b are 2 or more, the structures in parentheses may be the same or different from each other;
R ′, R ″ and R ″ ′ may be the same or different from each other, and each independently represents an alkyl group having 1 to 30 carbon atoms,
In Formula 2,
R is an alkyl group having 1 to 5 carbon atoms,
M ₁ and L ₁ may be the same or different from each other, and each independently represents a direct bond; or an alkylene group having 1 to 10 carbon atoms,
n1 and n2 may be the same as or different from each other, each independently an integer of 1 to 4,
When n1 and n2 are 2 or more, the structures in parentheses may be the same as or different from each other,
n3 is 0 or 1,
n4 is an integer of 0 to 4,
when n4 is 2 or more, the structures in parentheses may be the same as or different from each other;
R ₁₀₀ is hydrogen; deuterium; or an alkyl group having 1 to 30 carbon atoms.

  Moreover, one embodiment of the present invention provides a photosensitive material produced using the photosensitive resin composition and a color filter including the same.

  In forming a color filter pattern, the photosensitive resin composition according to an embodiment of the present invention can reduce the sensitivity and increase the luminance when realizing a hole in the pattern.

  In addition, the color filter manufactured using the photosensitive resin composition according to one embodiment of the present invention has a reduced surface abrasion of the pattern during the development process and is excellent in solvent resistance to the solvent.

The result of forming a color filter pattern using the photosensitive resin composition according to one embodiment of the present invention and the photosensitive resin composition produced as a comparative example, and comparing the chemical resistance of the color filter against the NMP solvent It is.

  Hereinafter, the present specification will be described in more detail.

  In this specification, when a part includes a component, this does not mean that the other component is excluded unless otherwise stated. It can also be included.

  According to one embodiment of the present specification, there is provided a photosensitive resin composition comprising the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

  In this specification, the term “substituted or unsubstituted” refers to deuterium, halogen atom, alkyl group, alkenyl group, alkoxy group, cycloalkyl group, arylalkenyl group, aryl group, aryloxy group, aralkyl group, aralkenyl. Group; alkylamine group; aralkylamine group; arylamine group; heteroaryl group; carbazole group; acryloyl group; acrylate group; ether group; nitrile group; nitro group; hydroxy group; cyano group; N, O, S or P atom It is substituted with one or more substituents selected from the group comprising heteroaryl groups containing one or more and anionic groups, or no substituents.

  In the present specification, the alkyl group may be linear or branched, and is not particularly limited, but may have 1 to 30 carbon atoms. Specific examples include, but are not limited to, methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, hexyl group, and heptyl group.

  In the present specification, the alkenyl group may be linear or branched, and is not particularly limited, but may have 2 to 25 carbon atoms. Specific examples include, but are not limited to, an alkenyl group substituted with an aryl group such as a stilbenyl group and a styrenyl group.

  In the present specification, the alkoxy group may be linear or branched, and is not particularly limited, but may have 1 to 30 carbon atoms.

  In the present specification, the cycloalkyl group is not particularly limited, but may have 3 to 20 carbon atoms, and may particularly be a cyclopentyl group or a cyclohexyl group.

  In the present specification, examples of the halogen atom include fluorine, chlorine, bromine or iodine.

  In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group.

  When the aryl group is a monocyclic aryl group, the number of carbon atoms may be 6 to 40, although not particularly limited. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group.

  When the aryl group is a polycyclic aryl group, the number of carbon atoms may be 10 to 40, although not particularly limited. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and a fluorenyl group.

When the fluorenyl group is substituted,
Spirofluorenyl groups, such as
(9,9-dimethylfluorenyl group), and
It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.

  In the present specification, the heteroaryl group is an aromatic heterocyclic group containing O, N, S or P as a hetero atom, and is not particularly limited, but may have 1 to 30 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridyl group, pyridazine group, quinolinyl. Group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, and dibenzofuran group. It is not limited.

  In the present specification, an alkylene group means one having two bonding positions in an alkane. The alkylene group may be a straight chain, a branched chain, or a ring chain. Although carbon number of an alkylene group is not specifically limited, 2-25 may be sufficient.

  In the present specification, the explanation of the aryl group can be applied except that the arylene group is a divalent group.

  In the present specification, the description of the heteroaryl group can be applied except that the heteroarylene group is a divalent group.

  In the present specification, adjacent groups bonded to each other to form a substituted or unsubstituted ring means a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; It is meant to form an unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof.

  In the present specification, an aliphatic hydrocarbon ring means a ring that is not aromatic and consists of only carbon and hydrogen atoms.

  Specifically, examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like. However, it is not limited to these.

  In the present specification, the aromatic hydrocarbon ring means an aromatic ring composed of only carbon and hydrogen atoms. In the present specification, specific examples of the aromatic hydrocarbon ring include phenyl group, naphthyl group, anthracenyl group, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene. , Indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but are not limited thereto.

  In this specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Specifically, examples of the aliphatic heterocycle include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, thiocan and the like. However, it is not limited to these.

  In the present specification, an aromatic heterocycle means an aromatic ring containing one or more heteroatoms. Specifically, examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole. , Pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolizine, benzothiazole , Benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzoca Bazoru, dibenzo carbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, although such indeno carbazole, not limited thereto.

  In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle may be monocyclic or polycyclic.

In one embodiment of the present specification, L _A and L _B may be the same or different from each other, and are each independently a direct bond; or an alkylene group having 1 to 10 carbon atoms.

In one embodiment, _{L A} and _{L B} are each a propylene group.

In one embodiment of the present specification, R _{A to} R _F may be the same or different from each other, and each independently represents hydrogen; deuterium; halogen atom; nitro group; substituted or unsubstituted carbon number 1 to A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted carbon group having 1 to 30 carbon atoms; Are selected from the group consisting of monocyclic or polycyclic heteroaryl groups.

In one embodiment, R _{A to} R _F are hydrogen.

According to one embodiment of the present specification, R _{1 to} R ₆ may be the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted straight chain having 1 to 6 carbon atoms. Or selected from the group consisting of branched alkyl groups, sulfonic acid groups, sulfonate groups, —SO ₂ NHR ₇ groups; and —SO ₂ NR ₈ R ₉ ;
R _{7 to} R ₉ may be the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present specification, R _{1 to} R ₆ may be the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted straight chain having 1 to 6 carbon atoms. Alternatively, it is selected from the group consisting of branched alkyl groups and sulfonate groups.

In one embodiment of the present specification, X _{1 to} X ₅ may be the same as or different from each other, and each independently represents hydrogen; deuterium; an anionic group; a hydroxy group; a substituted or unsubstituted carbon number of 1 A group consisting of a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms; And at least one of the X _{1 to} X ₅ is an anionic group.

In one embodiment herein, the anionic _{^{group, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -CO 2 H, -O 2 - Z +, -CO 2 At least one selected from the group consisting of R _a , —SO ₃ R _b and —SO ₃ NR _c R _d , Z ⁺ represents N (R _e ) ₄ ⁺ , Na ⁺ or K ⁺ ; _{a to} R _e each independently represents a substituted or unsubstituted straight or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; A group; and at least one selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms.

According to another embodiment of the present specification, the anionic group may be —SO ₃ ^— or —SO ₃ ^— Na ⁺ .

  The anionic group may itself have an anion, or may exist in the form of a complex compound together with other cations. Therefore, the sum of the total charges of the molecules of the compound of Formula 1 may vary depending on the number of substituted anionic groups. Since one amine group of the compound of the present invention has a cation, the sum of the total charges of the molecule has a value from 0 to 0 of the number of substituted anionic groups minus one. be able to.

  In one embodiment of the present specification, R ′, R ″ and R ″ ′ may be the same as or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L _{1 to} L ₄ may be the same as or different from each other, and are each independently a direct bond; or an alkylene group having 1 to 10 carbon atoms.

In one embodiment, L _{1 to} L ₄ are each an ethylene group.

In one embodiment of the present specification, R _{11 to} R ₁₄ , R _{21 to} R ₂₄ and R _{31 to} R ₃₄ may be the same as or different from each other, and each independently represents hydrogen; deuterium; or carbon number 1 to 30 alkyl groups.

In one embodiment of the present specification, R _{11 to} R ₁₄ , R _{21 to} R ₂₄ and R _{31 to} R ₃₄ may be the same as or different from each other, and are each independently hydrogen; or 1 to 10 carbon atoms. It is an alkyl group.

In one embodiment of the present specification, R _{11 to} R ₁₄ , R _{21 to} R ₂₄ and R _{31 to} R ₃₄ may be the same as or different from each other, and are each independently hydrogen; or a methyl group.

In one embodiment, R _{11 to} R ₁₄ are methyl groups.

In one embodiment, R _{22 to} R ₂₄ and R _{31 to} R ₃₄ are hydrogen.

According to one embodiment of the present specification, the compound represented by Formula 2 may be any one selected from the following compounds.

  In one embodiment of the present specification, the photosensitive resin composition may further include 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 resin composition.

  As the binder resin, a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility can be used, and a binder generally used in this technical field may be further included.

  In one embodiment, the binder resin includes an acrylic binder resin.

  The polyfunctional monomer imparting mechanical strength of the film may be any one selected from the group comprising unsaturated carboxylic acid esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and acid anhydrides. Or one or more.

  Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl (meth) acrylate. , 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- Droxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytri Propylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl ( (Meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexafluo Isopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl It is selected from the group consisting of acrylate and butyl α-hydroxymethyl acrylate, but is not limited thereto.

  Specific examples of the aromatic vinyl monomers include styrene, α-methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, p). -Selected from the group consisting of chlorostyrenes, but not limited thereto.

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

  Specific examples of the unsaturated imides are selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. It is not limited to only.

  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 examples thereof include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5- Group consisting of norbornene-2-carboxylic acid, mono-2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxypolycaprolactone mono (meth) acrylate Although it is preferable to use 1 or more types selected from these, it is not limited only to these.

  According to one embodiment of the present specification, the binder resin has an acid value of 50 to 130 KOH mg / g and a weight average molecular weight of 1,000 to 50,000.

  The polyfunctional monomer is a monomer that plays a role of forming a photoresist image by light. Specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6 -Hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, penta Erythritol tetramethacrylate and dipentaerythritol hex May be one or a mixture of two or more selected from the group consisting of methacrylates.

  The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light and catalyzes crosslinking. For example, the photoinitiator is selected from the group consisting of acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds. It may be one or more selected.

  Examples of the acetophenone compound 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, 2,2-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 Examples include, but are not limited to, -1- (4-morpholinophenyl) -butan-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, and the like. .

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

  Examples of the triazine compound include 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3-hexafluoro. Isopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4-bis (trichloromethyl) -s- Triazin-6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, cyclohexyl-2- {4- [2,4-Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, benzyl-2- {4- [2,4-bis (trick (Romethyl) -s-triazin-6-yl] phenylthio} acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 3- {4 -[2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionamide, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4- Bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine and the like Although it is mentioned, it is not limited to this.

  Examples of the oxime compound include 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (CGI124 manufactured by Ciba Geigy), ethanone, and -1- (9-ethyl). Examples include, but are not limited to, -6- (2-methylbenzoyl-3-yl)-, 1- (o-acetyloxime) (CGI242), N-1919 (manufactured by Adeka), and the like.

  Examples of the solvent include acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl. Ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, octane, cyclohexane , Benzene, toluene, xylene, methanol, ethanol, isopropa Propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, One or more selected from the group consisting of ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether are exemplified, but are limited to these. It is not a thing.

  In one embodiment of the present specification, the content of the compound represented by Formula 1 is 0.1 to 50 parts by weight based on the total weight of the solid content in the photosensitive resin composition. The content of the compound represented by Formula 2 is 0.01 to 10 parts by weight, the binder resin content is 1 to 60 parts by weight, and the photoinitiator content is 0.1 parts by weight. The content of the polyfunctional monomer is 0.1 to 50 parts by weight.

  The total weight of the solid content means the sum of the total weight of components obtained by removing the solvent from the resin composition. The weight part standard based on the solid content and the solid content of each component can be measured by a general analytical means used in the art such as liquid chromatography or gas chromatography.

  In one embodiment of the present specification, the photosensitive resin composition may further include at least one of a dye and a pigment.

  Each of the dye and the pigment plays a role of absorbing colors in a desired range and exhibiting a color, and can be classified into a dye and a pigment depending on the solubility in a solvent. A dye refers to a dye that has a high solubility in a solvent and is easy to dissolve, and a pigment refers to a dye that has a relatively low solubility and is difficult to dissolve.

  The dye may be at least one selected from the group including an anthraquinone dye, a tetraazaporphyrin dye, and a triarylmethane dye.

The anthraquinone dye may be represented by the following chemical formula 3.
[Chemical formula 3]

In Formula 3,
R ₁₁ and R ₁₂ are each independently at least one selected from the group consisting of an amino group, an alkylamino group, a dialkylamino group, a phenylamino group, and a diphenylamino group.

According to one embodiment of the present specification, the anthraquinone dye may be any one selected from the following compounds.

According to one embodiment of the present specification, the tetraazaporphyrin-based dye may be selected from the following compounds.

Moreover, according to one embodiment of the present specification, the triarylmethane dye may be any one selected from the following compounds.

  In one embodiment of the present specification, the pigment is a blue pigment.

  The blue pigment is, for example, C.I. I. Pigment blue 15, C.I. I. Pigment blue 15: 3, C.I. I. Pigment blue 15: 4, C.I. I. Pigment blue 15: 6, C.I. I. Pigment Blue 60 or the like may be included.

  In one embodiment, the pigment may include a copper phthalocyanine pigment.

  The blue dye may include, for example, a methyl dye, an anthraquinone dye, an azo dye, a triarylmethane dye, a phthalocyanine dye, and the like as a blue dye.

  In addition, the blue pigment may include, for example, a blue lake pigment obtained by lacquering the blue pigment as described above with a lake agent. The rake agent is not particularly limited. For example, phosphotungstic acid, phosphomolybdic acid, phosphotungstic molybdic acid, tannic acid, lauric acid, 3,4,5-trihydroxybenzoic acid, ferricyanide, ferrocyanide Etc. can be used.

  Specific examples of blue lake pigments include C.I. I. Pigment blue 1, C.I. I. Pigment blue 1: 2, C.I. I. Pigment blue 2, C.I. I. Pigment blue 3, C.I. I. Pigment blue 8, C.I. I. Pigment blue 9, C.I. I. Pigment blue 10, C.I. I. Pigment blue 12, C.I. I. Pigment blue 14, C.I. I. Pigment blue 17: 1, C.I. I. Pigment blue 18, C.I. I. Pigment blue 19, C.I. I. Pigment blue 24, C.I. I. Pigment blue 24: 1, C.I. I. Pigment blue 53, C.I. I. Pigment blue 56, C.I. I. Pigment blue 56: 1, C.I. I. Pigment blue 61, C.I. I. Pigment blue 61: 1, C.I. I. Pigment blue 62, C.I. I. Pigment blue 63, C.I. I. And CI Pigment Blue 78.

In one embodiment of the present specification, the photosensitive resin composition further includes a dispersant, and the dispersant includes a repeating unit represented by the following chemical formula 11 or a repeating unit represented by the chemical formula 12. May be included.
[Chemical formula 11]
[Chemical formula 12]

In Chemical Formula 11 and Chemical Formula 12,
R ₃₀₁ and R ₄₀₁ may be the same or different from each other, and each independently represents hydrogen; or an alkyl group having 1 to 10 carbon atoms;
R ₃₀₂ , R ₃₀₃ , R ₄₀₂ and R ₄₀₃ may be the same as or different from each other, and each independently represents hydrogen; an alkyl group having 1 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms; 1-30 heteroaryl groups,
R ₃₀₂ and R ₃₀₃ or R ₄₀₂ and R ₄₀₃ are bonded to each other to form a substituted or unsubstituted ring;
Ar ₃ and Ar ₄ may be the same as or different from each other, and are each independently a direct bond; an alkylene group having 1 to 10 carbon atoms; — [CH (R ₃₁₁ ) —CH (R ₃₁₂ ) —O] _x A divalent linking group represented by —CH (R ₃₁₃ ) —CH (R ₃₁₄ ) — or — [(CH ₂ ) _y1 —O] _z — (CH ₂ ) _y2 —,
R _{311 to} R ₃₁₄ may be the same as or different from each other, and each independently represents hydrogen; or an alkyl group having 1 to 10 carbon atoms;
x is an integer of 1 to 18, and when x is 2 or more, the structures in parentheses may be the same as or different from each other;
y1 and y2 may be the same as or different from each other, and are each independently an integer of 1 to 5,
z is an integer of 1 to 18, and when z is 2 or more, the structures in parentheses may be the same as or different from each other;
Q is any one selected from the group consisting of a direct bond; an alkylene group having 1 to 10 carbon atoms; an arylene group having 6 to 30 carbon atoms; —CONH—; —COO—; and an ether group having 1 to 10 carbon atoms. It is a linking group in which one or two or more are linked.

  In one embodiment, the dispersant may be included in an amount of 0.5 to 50 parts by weight based on the total weight of solids in the resin composition.

  According to one embodiment of the present specification, the resin composition may further include an antioxidant.

  According to one embodiment of the present specification, the content of the antioxidant is 0.1 to 20 parts by weight based on the total weight of solids in the resin composition.

  According to one embodiment of the present specification, the resin composition includes a photocrosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent. It further comprises one or more additives selected from the group consisting of:

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

  Examples of the photocrosslinking sensitizer include benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3 Benzophenone compounds such as 1,3-dimethyl-4-methoxybenzophenone and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9 -Fluorenone compounds such as fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone Xanthone compounds such as xanthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butylanthraquinone and 2,6-dichloro-9,10-anthraquinone; 9-phenyl Acridine compounds such as acridine, 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; benzyl, 1,7 , 7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, dicarbonyl compounds such as 9,10-phenanthrenequinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6 -Dimethoxybenzoyl) -2,4,4-trimethylpen Phosphine oxide compounds such as ruphosphine oxide; benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl-cyclopentanone Amino synergists such as 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl- 7-methoxy-coumarin, 10,10-ca Such as rubonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolizin-11-one One or more selected from the group consisting of coumarin compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthothiazoline can be used.

  The curing accelerator is used to increase curing and mechanical strength, and specifically includes 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and 2,5-dimercapto. 1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol- A group consisting of tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) One or more selected can be used.

  As an adhesion promoter used in the present specification, one or more of methacryloylsilane coupling agents such as methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane and the like are used. The alkyltrimethoxysilane can be used by selecting one or more kinds from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like.

  The surfactant is a silicon-based surfactant or a fluorine-based surfactant. Specifically, examples of the silicon-based surfactant include BYK-077, BYK-085, BYK-300, BYK manufactured by BYK-Chemie. -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-371, BYK-375, BYK-380, BYK -390 etc. can be used, and DIC (D iNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F -470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486 , F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF -1311, TF1132, TF1027SF, TF-1441, TF-1442, etc. can be used, but limited to these. Is not something

  Examples of the antioxidant include one or more selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant. However, it is not limited to these.

  Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy- 3,5-di-tert-butylphenyl) propionate, tetrabis [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, 3,5-di-tert-butyl-4-hydroxybenzyl phosphite diethyl ester, 2,2-thiobis (4-methyl) -6-tert-butylphenol), 2,6-g, tert-butylphenol 4,4'-butylidene-bis (3-methyl-6-tert-butylphenol) ), 4,4′-thiobis (3-methyl-6-tert-butylphenol) or bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoic acid] glycol ester (Bis Hindered phenol-based primary antioxidants such as [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoicacid] glycol ester); phenyl-α-naphthylamine, phenyl- Amine-based secondary antioxidants such as β-naphthylamine, N, N′-diphenyl-p-phenylenediamine or N, N′-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopro Pionate, distearyl thiopropionate, mel Thio secondary antioxidants such as captobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phos Phyto, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) pentaerythritol diphosphite) or (1,1'-biphenyl) -4,4'-diylbisphosphonite tetrakis [2 , 4-Bis (1,1-dimethylethyl) phenyl] ester ((1,1′-Biphenyl) -4,4′-Diylbisphosphono acid acid tetrakis [2,4 bis (1,1-dimethylethyl) phenyl] ester) phosphite secondary antioxidant such as and the like.

  As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but are not limited thereto. Any of those generally used can be used.

  Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxyamine aluminum salt. , P-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2-methylenebis (4-methyl-6-t) -Butylphenol), 2-mercaptoimidazole and phenothiazine may be included, but is not limited thereto and is generally known in the art. It may include those which.

  The dispersant can be used by a method in which the pigment is surface-treated in advance or added internally to the pigment, or a method in which the pigment is externally added. As the dispersant, a compound type, nonionic, anionic, or cationic dispersant can be used, such as a fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, or amphoteric surfactant. Is mentioned. These may be used respectively or in combination of two or more.

  Specifically, the dispersant includes polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, carboxylic acid Examples thereof include, but are not limited to, one or more selected from the group consisting of a salt, an alkylamide alkylene oxide adduct, and an alkylamine.

  The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamidoamine, reaction products of amines and epoxides, and specific examples of nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing compounds. However, the present invention is not limited to this, and any of those generally used in the art can be used.

One embodiment of the present specification includes a compound represented by the following chemical formula 15, a compound represented by the following chemical formula 2, a dye, and a dispersant, and the dye is a triarylmethane-based dye. A photosensitive resin composition is provided.
[Chemical formula 15]
[Chemical formula 2]

In the chemical formula 15, the definitions of the R _{1 to} R ₆ , R _{A to} R _F , R _AA , R _BB and X _{1 to} X _{5 and} the definition of the chemical formula 2 are as described above.

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

  More specifically, the present invention provides a photosensitive material in the form of a thin film or pattern in which a resin composition according to an embodiment of the present invention is coated on a substrate by an appropriate method.

  The application method is not particularly limited, and a spray method, a roll coating method, a spin coating method, and the like can be used. Usually, the spin coating method is widely used. Moreover, after forming a coating film, you may remove a part of residual solvent under reduced pressure depending on the case.

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

  The resin composition according to the present specification is a pigment-dispersed photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a thin film transistor liquid crystal display (TFT LCD) or organic light emitting diode black matrix, and an overcoat layer formation. It can be used for photosensitive materials, column spacer photosensitive materials, photocurable paints, photocurable inks, photocurable adhesives, printing plates, printed wiring board photosensitive materials, plasma display panel (PDP) photosensitive materials, etc. The application is not particularly limited.

  According to an embodiment of the present specification, a color filter including the photosensitive material is provided.

  The color filter includes the photosensitive resin composition described above. The photosensitive resin composition is applied onto a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.

  The resin composition according to one embodiment of the present specification can provide a color filter capable of reducing sensitivity and realizing high luminance when realizing holes in a pattern.

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

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

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

  A grid-like black pattern called a black matrix can be arranged between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the black matrix material. In this case, it is possible to use a method in which chromium is deposited on the entire glass substrate and a pattern is formed by etching. However, a resin black matrix by a pigment dispersion method that can be finely processed can be used in consideration of high cost in the process, high reflectance of chromium, and environmental contamination due to chromium waste liquid.

  In the black matrix according to one embodiment of the present specification, a black pigment or a black dye can be used as a coloring material. For example, carbon black may be used alone, or a mixture of carbon black and a color pigment may be used. At this time, since the color pigment lacking in light shielding properties is mixed, there is an advantage that even if the amount of the color material is relatively increased, the strength of the film and the adhesion to the substrate are not lowered.

  A display device including a color filter according to the present specification is provided.

  The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a liquid crystal display (LCD). Any one of a liquid crystal display (Thin Film Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (Cathode Ray Tube, CRT) may be used.

  Hereinafter, the present specification will be described in detail by way of examples in order to specifically describe the present specification. However, the examples according to the present specification can be modified in various other forms, and the scope of the present specification should not be construed to be limited to the examples described below. The examples herein are provided to more fully explain the present specification to those skilled in the art.

Synthesis of Compound In order to produce a photosensitive resin composition according to one embodiment of the present specification, Compound 1 was generated according to the following Reaction Scheme 1.
[Reaction Formula 1]

5 g of A-1 (8.710 mmol), 8.233 g of B-1 (34.838 mmol), 4.815 g of K ₂ CO ₃ (34.5838 mmol) were placed in 100 ml of NMP and stirred at 95 ° C. for 12 hours. Thereafter, the solvent was removed under reduced pressure, and 200 ml of water was added to the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Thereafter, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH)

  As a result, 6 g of Compound 1 (3.322 mmol) was obtained, and the yield was 72%.

The results are as follows.
Ionization mode =: APCI +: m / z = 949 [M + H] +, Exact Mass: 948

The measurement result of ¹ H-NMR of the compound 1 is as follows.
¹ H NMR (500 MHz, DMSO, ppm): 8.03 (m, 11H), 7.69-7.18 (m, 10H), 699-6.95 (t, 1H), 6.80- 6.01 (dd, 1H), 5.93 to 5.85 (dd, 1H), 4.06 to 3.79 (m, 4H), 3.72 to 3.60 (m, 4H), 2. 17-1.70 (m, 16H)
[Reaction Formula 2]

As shown in Reaction Scheme 2, 1.43 g of C-1 (2.732 mmol), 2.99 g of B-1 (9.490 mmol), 1.31 g of K ₂ CO ₃ (9.490 mmol) in 20 ml of NMP. And stirred at 95 ° C. for 12 hours. Thereafter, the solvent was removed under reduced pressure, and 200 ml of water was added to the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Thereafter, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH)

As a result, 1.622 g of compound 2 (1.912 mmol) was obtained, and the yield was 70%.
Ionization mode =: APCI +: m / z = 977 [M + H] +, Exact Mass: 976
[Reaction Formula 3]

As shown in Reaction Scheme 3, 1.608 g of D-1 (2.732 mmol), 2.99 g of B-1 (9.490 mmol), 1.31 g of K ₂ CO ₃ (9.490 mmol) in 20 ml of NMP. And stirred at 95 ° C. for 12 hours. Thereafter, the solvent was removed under reduced pressure, and 200 ml of water was added to the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Thereafter, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH)

As a result, 1.526 g of compound 3 (1.622 mmol) was obtained, and the yield was 59%.
Ionization mode =: APCI +: m / z = 963 [M + H] +, Exact Mass: 962

Experimental Examples Examples 1 to 4 and Comparative Examples 1 to 3 were manufactured at the ratios shown in Table 1 below. The dosage unit for each configuration is grams (g).

Experimental Example 1 Measurement of film scraping The photosensitive resin composition was spin-coated on glass (5 cm × 5 cm), and prebaked at 110 ° C. for 70 seconds to form a film. The entire surface of the substrate was irradiated with an exposure amount of 30 mJ / cm ² . After removing the film layer at the center of the substrate, the step was confirmed using a surface level difference measuring instrument.

  Thereafter, the exposed substrate was developed with a developer (KOH, 0.04%) at 0.1 mPa for 55 seconds, and a step was confirmed using a surface level difference measuring instrument.

  Steps before and after development were confirmed, and the degree of film abrasion was determined and shown in Table 2 below.

Experimental Example 2. Evaluation of Peeling The photosensitive resin composition was spin-coated on glass (5 cm × 5 cm), and prebaked at 110 ° C. for 70 seconds to form a film. The distance between the substrate on which the film was formed and the photomask was 600 μm, and the entire surface of the substrate was irradiated with an exposure amount of 30 mJ / cm ² . Thereafter, the exposed substrate was developed with a developer (KOH, 0.04%) at 0.2 mPa for 300 seconds, and then the pattern was observed with an Olympus optical microscope to confirm the degree of pattern peeling. The degree of peeling is shown in FIG.

  As shown in Table 2 and attached FIG. 1, the photosensitive resin compositions of Examples 1 to 4 including both the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 were used. Thus, it was found that when the color filter was manufactured, the effect of reducing film scraping and peeling was obtained.

Claims (15)

A compound represented by the following chemical formula 1, a compound represented by the following chemical formula 2,
A photosensitive resin composition comprising:
[Chemical Formula 1]
[Chemical formula 2]
(In Chemical Formula 1,
L _A and L _B may be the same or different from each other, and each independently represents a direct bond; or an alkylene group having 1 to 10 carbon atoms,
R _{A to} R _F may be the same or different from each other, and each independently represents hydrogen; deuterium; halogen atom; nitro group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl having 1 to 30 carbon atoms; Selected from the group consisting of:
R _{1 to} R ₆ may be the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen atom; a substituted or unsubstituted C 1-6 linear or branched alkyl group; Selected from the group consisting of a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms; a sulfonic acid group; a sulfonic acid ester group; a sulfonic acid group; a —SO ₂ NHR ₇ group; and —SO ₂ NR ₈ R ₉ ;
R _{7 to} R ₉ may be the same as or different from each other, and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms,
X _{1 to} X ₅ may be the same or different from each other, and each independently represents hydrogen; deuterium; an anionic group; —CO ₂ R _a ; —SO ₃ R _b ; —SO ₃ NR _c R _d ; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic group having 1 to 30 carbon atoms; Selected from the group consisting of cyclic or polycyclic heteroaryl groups;
At least one of the X _{1 to} X ₅ is at least one selected from the group consisting of an anionic group, —CO ₂ R _a , —SO ₃ R _b and —SO ₃ NR _c R _d ;
R _{a to} R _d each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and substituted or unsubstituted And at least one selected from the group consisting of substituted monocyclic or polycyclic heteroaryl groups having 1 to 30 carbon atoms,
R _AA and R _BB may be the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon group having 1 to 30 carbon atoms. A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms; a halogen atom; a nitro group ; phenoxy group; a carboxy group; a carboxylic acid ester group; carboxylate; alkoxycarbonyl group; a hydroxyl group; a sulfonic acid group; a sulfonic acid ester group; _sulfonate; -SO 2 _NHR'; and _-SO 2 NR Selected from the group consisting of
a and b may be the same or different from each other, and each independently represents an integer of 0 to 4;
when a and b are 2 or more, the structures in parentheses may be the same or different from each other;
R ′, R ″ and R ″ ′ may be the same or different from each other, and each independently represents an alkyl group having 1 to 30 carbon atoms,
In Formula 2,
R is an alkyl group having 1 to 5 carbon atoms,
M ₁ and L ₁ may be the same or different from each other, and each independently represents a direct bond; or an alkylene group having 1 to 10 carbon atoms,
n1 and n2 may be the same as or different from each other, each independently an integer of 1 to 4,
When n1 and n2 are 2 or more, the structures in parentheses may be the same as or different from each other,
n3 is 1,
n4 is an integer of 1 to 4,
when n4 is 2 or more, the structures in parentheses may be the same as or different from each other;
R ₁₀₀ is hydrogen; deuterium; or an alkyl group having 1 to 30 carbon atoms. ) The anionic ^{_{groups, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -CO 2 H, and _-O ² - is at least one selected from the group consisting of ^{Z +} ,
Z ⁺ represents N (R _e ) ₄ ⁺ , Na ⁺ or K ⁺ ,
R _{a to} R _e may be the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic group having 6 to 30 carbon atoms; A ring aryl group; and at least one selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms,
The photosensitive resin composition according to claim 1. The compound represented by Formula 2 is any one selected from the following compounds:
The photosensitive resin composition of Claim 1 or 2.
A binder resin, a polyfunctional monomer, a photoinitiator, and a solvent;
The photosensitive resin composition as described in any one of Claims 1-3. Based on the total weight of solids in the photosensitive resin composition,
The content of the compound represented by Chemical Formula 1 is 0.1 to 50 parts by weight,
The content of the compound represented by Chemical Formula 2 is 0.01 to 10 parts by weight,
The binder resin content is 1 to 60 parts by weight,
The photoinitiator content is 0.1 to 20 parts by weight,
The content of the polyfunctional monomer is 0.1 to 50 parts by weight,
The photosensitive resin composition of Claim 4. Further comprising at least one of a dye and a pigment,
The photosensitive resin composition as described in any one of Claims 1-5. The dye is at least one selected from the group comprising an anthraquinone dye, a tetraazaporphyrin dye, and a triarylmethane dye.
The photosensitive resin composition of Claim 6. The anthraquinone dye is represented by the following chemical formula 3.
The photosensitive resin composition of Claim 7.
[Chemical formula 3]
(In Formula 3 above,
R ₁₁ and R ₁₂ are each independently at least one selected from the group consisting of an amino group, an alkylamino group, a dialkylamino group, a phenylamino group, and a diphenylamino group. ) The anthraquinone dye is any one selected from the following compounds:
The photosensitive resin composition of Claim 7.
The tetraazaporphyrin-based dye is any one selected from the following compounds:
The photosensitive resin composition of Claim 7.
The triarylmethane dye is any one selected from the following compounds:
The photosensitive resin composition according to claim 7 , wherein z ⁻ is a counter anion.
It further includes a dispersant, and the dispersant includes a polymer containing a repeating unit represented by the following chemical formula 11 or a repeating unit represented by the chemical formula 12.
The photosensitive resin composition as described in any one of Claims 1-4.
[Chemical formula 11]
[Chemical formula 12]
(In Chemical Formula 11 and Chemical Formula 12,
R ₃₀₁ and R ₄₀₁ may be the same or different from each other, and each independently represents hydrogen; or an alkyl group having 1 to 10 carbon atoms;
R ₃₀₂ , R ₃₀₃ , R ₄₀₂ and R ₄₀₃ may be the same as or different from each other, and each independently represents hydrogen; an alkyl group having 1 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms; 1-30 heteroaryl groups,
R ₃₀₂ and R ₃₀₃ or R ₄₀₂ and R ₄₀₃ are bonded to each other to form a substituted or unsubstituted ring;
Ar ₃ and Ar ₄ may be the same as or different from each other, and are each independently a direct bond; an alkylene group having 1 to 10 carbon atoms; — [CH (R ₃₁₁ ) —CH (R ₃₁₂ ) —O] _x A divalent linking group represented by —CH (R ₃₁₃ ) —CH (R ₃₁₄ ) — or — [(CH ₂ ) _y —O] _z — (CH ₂ ) _y —,
R _{311 to} R ₃₁₄ may be the same as or different from each other, and each independently represents hydrogen; or an alkyl group having 1 to 10 carbon atoms;
x is an integer of 1 to 18, and when x is 2 or more, the structures in parentheses may be the same as or different from each other;
y is an integer of 1 to 5,
z is an integer of 1 to 18, and when z is 2 or more, the structures in parentheses may be the same as or different from each other;
Q is any one selected from the group consisting of a direct bond; an alkylene group having 1 to 10 carbon atoms; an arylene group having 6 to 30 carbon atoms; —CONH—; —COO—; and an ether group having 1 to 10 carbon atoms. It is a linking group in which one or two or more are linked. )   The photosensitive material manufactured using the photosensitive resin composition as described in any one of Claims 1-12.   A color filter comprising the photosensitive material according to claim 13.   A display device comprising the color filter according to claim 14.