KR101745062B1 - Resin composition, photosensitive material, color filter and display appratus - Google Patents

Abstract

In this specification, a resin composition containing a colorant-containing polymer, a light-sensitive material manufactured using the resin composition, a color filter, and a display device including the colorant are described.

Description

Technical Field [0001] The present invention relates to a resin composition, a photosensitive material, a color filter, and a display device,

The present invention relates to a resin composition. Further, the present invention relates to a photosensitive material, a color filter, and a display device including the same, which are manufactured using the resin composition.

In recent years, LEDs, OLEDs, and QDs have been widely used as light sources for liquid crystal displays (LCDs) instead of conventional CCFLs. However, in order to manufacture thin-film displays and flexible displays, display products using a self-emission such as an LED, OLED or QD as a unit pixel have been developed and produced.

However, display using LEDs, OLEDs, and QDs as unit pixels is difficult to maximize, so even when using LEDs, OLEDs, QDs, etc., .

In order to realize a desired color, a light source and an appropriate color filter are required, and it is difficult to realize a desired color coordinate by using a currently used color material, and development of a new color material is required.

In addition, in the case of the pigment dispersion method applied to the production of a color filter resist, the pigment has been striving to achieve high brightness and high contrast through atomization of the pigment. However, in order to realize a higher level of brightness, In addition to pigments, new pigments and dyes must be excavated.

In the case of a color filter using a conventional pigment type color resist, the number of pigments having absorption and transmission spectra suitable for the light source to be used is limited, and it is difficult to finely control absorption and transmission spectra. In the case of a color filter using a dye type color resist or a dye pigment hybrid color resist, absorption and transmission spectra suitable for a light source to be applied can be obtained by using various dyes. In this case, a color reproduction ratio, a high luminance, and a high contrast ratio .

Korean Patent Publication No. 2001-0009058

In this specification, a resin composition containing a colorant-containing polymer is described. Also, in this specification, a photosensitive material, a color filter, and a display device including the photosensitive material, which are manufactured using the resin composition, are described.

An embodiment of the present invention provides a resin composition comprising a polymer comprising a unit represented by the following formula (1).

In Formula 1,

n is an integer of 1 to 3,

m is an integer of 1 to 4,

X is NR or O,

R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; And a substituted or unsubstituted C2 to C25 alkenyl group,

L ₁ is a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

L ₂ is a direct bond; A substituted or unsubstituted alkylene group having 1 to 25 carbon atoms; Or a substituted or unsubstituted carbonyl group having 1 to 40 carbon atoms,

R ₁ and R ₂ are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted 7 to 50 aralkyl group; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,

R ₃ is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

R ₄ and R ₅ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,

R ₆ to R ₈ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms.

In one embodiment of the present invention, there is provided a photosensitive material produced using the photosensitive resin composition.

In one embodiment of the present invention, a color filter including the photosensitive material is provided.

In one embodiment of the present invention, a display device including the color filter is provided.

The photosensitive resin composition comprising a polymer according to one embodiment of the present specification is excellent in heat resistance and / or chemical resistance. The photosensitive resin composition according to one embodiment of the present invention can obtain absorption and transmission spectra suitable for a light source to be applied, and can achieve a higher color reproducibility, a higher luminance, a higher contrast ratio, and the like. The photosensitive resin composition according to one embodiment of the present specification has a high degree of crosslinking and is excellent in heat resistance and chemical resistance. Accordingly, the photosensitive resin composition according to one embodiment of the present invention has less color change due to heat treatment and less elution with respect to a solvent.

Fig. 1 shows the results of measurement of chemical resistance in Examples and Comparative Examples.
2 shows the transmittance spectra of the polymers prepared in Production Examples 1-1, 1-3 and 1-7.
Fig. 3 shows the transmittance spectra of Example 15 and Comparative Example 3. Fig.

Hereinafter, the present invention will be described in detail.

One embodiment of the present invention provides a resin composition comprising a polymer containing the unit represented by the formula (1).

The polymer according to the above-described embodiment is characterized in that a dye structure having a styryl-based structure is introduced into the polymer. Thus, heat resistance and / or chemical resistance can be improved.

According to one embodiment of the present invention, the polymer may further include at least one unit selected from the following formulas (2) to (9).

In Formula 2,

R ₉ to R ₁₁ are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

R ₁₂ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms.

In Formula 3,

R ₁₃ , R ₁₅ and R ₁₆ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

R ₁₄ is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms or a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms.

In Formula 4,

R ₁₇ , R ₁₉ and R ₂₀ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

R ₁₈ is a substituted or unsubstituted (meth) acrylalkyl group having 5 to 25 carbon atoms.

In Formula 5,

R ₂₁ to R ₂₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms.

In Formula 6,

R ₂₅ to R ₂₇ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms.

In Formula 7,

R ₂₈ and R ₂₉ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

R ₃₀ is an alkyl group having 1 to 25 carbon atoms; Or an alkyl ester group having 2 to 25 carbon atoms.

In Formula 8,

R ₄₁ to R ₄₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

R ₄₄ is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; Or a substituted or unsubstituted C2 to C25 alkenyl group having 5 to 20 carbon atoms.

In Formula 9,

R ₅₁ to R ₅₃ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

L ₇ is -C (= O) - or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms,

L ₈ is a substituted or unsubstituted alkenylene group having 2 to 25 carbon atoms, methylene, ethylene or propylene.

According to one embodiment of the present invention, the polymer includes units of the above formula (1) and units of at least one of the above formulas (2) to (9). In this case, the molar ratio of the unit represented by the formula (1) and the unit represented by the formula (2) to (9) is preferably 0.001: 1 to 1: 0.001.

According to one embodiment of the present disclosure, the polymer comprises units of formula (1) and units of formula (2). In this case, the molar ratio is preferably 0.001: 1 to 1: 0.001.

According to one embodiment of the present invention, the polymer comprises a unit of the formula (1) and a unit of the formula (4). In this case, the molar ratio is preferably 0.001: 1 to 1: 0.001.

According to another embodiment of the present invention, the polymer comprises a unit of the formula (1), a unit of the formula (2), and a unit of the formula (3). It is preferable that the ratio of the number of moles of the unit of the formula (1) to the sum of the moles of the remaining units is 0.001: 1 (x + y) to 1: 0.001 (x + y). (x + y = 1). The molar ratio of each of the remaining units to the units of Formula 1 is preferably 0.001: 1 to 1: 0.001.

According to another embodiment of the present invention, the polymer comprises a unit of formula (1), a unit of formula (4), and a unit of formula (6). It is preferable that the ratio of the number of moles of the unit of the formula (1) to the sum of the moles of the remaining units is 0.001: 1 (x + y) to 1: 0.001 (x + y). (x + y = 1). The molar ratio of each of the remaining units to the units of Formula 1 is preferably 0.001: 1 to 1: 0.001.

According to another embodiment of the present disclosure, the polymer comprises a unit of formula (1), a unit of formula (2), and a unit of formula (6). It is preferable that the ratio of the number of moles of the unit of the formula (1) to the sum of the moles of the remaining units is 0.001: 1 (x + y) to 1: 0.001 (x + y). (x + y = 1). The molar ratio of each of the remaining units to the units of Formula 1 is preferably 0.001: 1 to 1: 0.001.

According to another embodiment of the present invention, the polymer comprises a unit of formula (1), a unit of formula (2), a unit of formula (4) and a unit of formula (z) It is preferable that the ratio of the number of moles of the unit represented by Formula 1 to the number of moles of the remaining units is 0.001: 1 (x + y + z) to 1: 0.001 (x + y + z). (x + y + z = 1). The molar ratio of each of the remaining units to the units of Formula 1 is preferably 0.001: 1 to 1: 0.001.

According to another embodiment of the present disclosure, the polymer comprises a unit of formula (1), a unit of formula (3), a unit of formula (4) and a unit of formula (z) It is preferable that the ratio of the number of moles of the unit represented by Formula 1 to the number of moles of the remaining units is 0.001: 1 (x + y + z) to 1: 0.001 (x + y + z). (x + y + z = 1). The molar ratio of each of the remaining units to the units of Formula 1 is preferably 0.001: 1 to 1: 0.001.

According to one embodiment of the present invention, the weight average molecular weight of the polymer is 1,000 to 30,000.

According to one embodiment of the present invention, the PDI of the polymer is 1 to 3.

According to one embodiment of the present invention, the acid value of the polymer is 0 to 200 KOH mg / g.

According to another embodiment of the present invention, the formula (1) is represented by the following formula (11).

In the above formula (11), the description of the substituent is as shown in formula (1).

According to one embodiment of the present invention, the formula (2) may be represented by the following formula (21).

In Formula 21,

L ₃ is a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 25 carbon atoms,

Each R < ₃₁ > is independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

r is an integer of 1 to 5;

According to one embodiment of the present disclosure, L ₃ is an alkylene group having 1 to 6 carbon atoms, and R ₃₁ is hydrogen.

According to one embodiment of the present invention, the formula (3) may be represented by any one of the following formulas (31) to (33).

In Formulas 31 to 33,

L ₄ is a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 25 carbon atoms,

R ₃₂ to R ₃₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,

s is an integer of 1 to 10, t is an integer of 1 to 8, and u is an integer of 1 to 12.

According to one embodiment of the present disclosure, L ₄ is a direct bond and R ₃₂ to R ₃₄ are hydrogen.

 According to one embodiment of the present invention, Formula 4 may be represented by Formula 41 below.

In the above formula (41)

L ₅ is a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 25 carbon atoms,

R ₃₅ is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms.

According to one embodiment of the present invention, L ₅ is a linear or branched alkylene group having 1 to 6 carbon atoms which is substituted or unsubstituted with a hydroxy group, and R ₃₅ is hydrogen or an alkyl group having 1 to 6 carbon atoms.

According to one embodiment of the present invention, the formula (8) may be represented by the following formula (42) or (43).

In the formula (42), v is an integer of 0 to 6.

In Formula 43, L ₆ is alkylene having 1 to 6 carbon atoms.

According to one embodiment of the present invention, the formula (9) may be represented by the following formula (51) or (52).

In Formulas 51 and 52, R ₅₁ to R ₅₃ , L ₇ and L ₈ are as defined in Formula 9,

R ₅₄ is hydrogen or a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms,

w is an integer of 0 to 4;

According to one example, in the above formula (9), (51) or (52), L ₈ is methylene, ethylene or propylene. According to one example, in the above formula (9), (51) or (52), L ₈ is ethylene. The unit of the above formula (9) may be derived from an epoxy compound such as glycidyloxystyrene (GOS) or glycidyl methacrylate (GMA).

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; Carbazole group; Acryloyl group; Acrylate groups; Ether group; A fluorenyl group; A nitrile group; A nitro group; A hydroxy group; A cyano group, and a heterocyclic group containing at least one of N, O, S, or P atoms, or has no substituent group.

 In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 25. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

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

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 25.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 20 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group.

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

등이 있다.In the present specification, a fluorenyl group is a structure in which two ring organic compounds are connected via one atom,

.

등이 있다. In the present specification, a fluorenyl group includes a structure of an open fluorenyl group, wherein an open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring compounds are connected through one atom, For example,

.

In the present specification, the aralkyl group is specifically an aryl moiety having 6 to 49 carbon atoms, and the alkyl moiety has 1 to 44 carbon atoms. Specific examples thereof include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, Group, an?,? -Methylphenylbenzyl group, a 1-naphthylbenzyl group, a 2-naphthylbenzyl group, a p-fluorobenzyl group, a 3,5-difluorobenzyl group, , p-methoxybenzyl group, m-methoxybenzyl group,? -phenoxybenzyl group,? -benzyloxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, But are not limited to, an ethyl group, an aminobenzyl group, a nitrobenzyl group, a cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group and the like.

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 is not particularly limited, but is preferably 6 to 40 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 40 carbon atoms. 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 klycenyl group and a fluorenyl group.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing O, N or S, and the number of carbon atoms is not particularly limited, but is preferably 2-40 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, And the like, but the present invention is not limited thereto.

In the present specification, the alkylene group means that there are two bonding sites in the alkane. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, but is, for example, 2 to 25 carbon atoms.

In one embodiment of the present specification, R ₁ and R ₂ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.

In one embodiment of the present invention, R ₁ and R ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.

In the present specification, R ₁ and R _{2, which} are substituents of the amine, are substituted or unsubstituted aryl groups having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, the side chain of the polymer containing the same has a high molecular weight and is excellent in heat resistance.

In one embodiment of the present specification, R ₁ and R ₂ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.

In one embodiment of the present specification, R ₁ is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.

In one embodiment of the present specification, R ₁ is a substituted or unsubstituted methyl group.

In one embodiment of the present specification, R ₁ is a methyl group.

In one embodiment of the present specification, R ₁ is a substituted or unsubstituted ethyl group.

In one embodiment of the present specification, R ₁ is an ethyl group.

In one embodiment of the present specification, R ₁ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

In one embodiment of the present specification, R ₁ is a substituted or unsubstituted phenyl group.

In one embodiment of the present invention, R ₁ is a phenyl group.

In one embodiment of the present specification, R ₁ is a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.

In one embodiment of the present specification, R ₁ is a substituted or unsubstituted benzyl group.

In one embodiment of the present specification, R ₁ is a benzyl group.

In one embodiment of the present specification, R ₂ is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.

In one embodiment of the present specification, R ₂ is a substituted or unsubstituted methyl group.

In one embodiment of the present specification, R ₂ is a methyl group.

In one embodiment of the present invention, R ₂ is a substituted or unsubstituted ethyl group.

In one embodiment of the present specification, R ₂ is an ethyl group.

In one embodiment of the present specification, R ₂ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

In one embodiment of the present specification, R ₂ is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R ₂ is a phenyl group.

In one embodiment of the present specification, R ₂ is a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms.

In one embodiment of the present specification, R ₂ is a substituted or unsubstituted benzyl group.

In one embodiment of the present specification, R ₂ is a benzyl group.

In one embodiment of the present specification, R ₄ is a nitrile group; A heterocyclic group containing at least one of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, a nitrile group and N, O and S atoms An aryl group having 6 to 40 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from R < 2 > Or a heterocyclic group containing at least one of halogen, alkyl, alkenyl, cycloalkyl, aryl, arylamine, alkylamine, carbazole, fluorenyl, nitrile and N, O and S atoms And a heterocyclic group containing at least one of N, O, and S atoms substituted or unsubstituted with at least one substituent selected from the group

In one embodiment of the present invention, R ₄ in Formula 1 is a nitrile group.

In one embodiment of the present invention, L ₂ in Formula 1 is a substituted or unsubstituted carbonyl group.

In one embodiment of the present invention, L ₁ represents a group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylamine group, an alkylamine group, a carbazole group, a fluorenyl group, an acryloyl group, And a heterocyclic group containing at least one of N, O and S atoms. The alkylene group is a straight or branched chain alkylene group of 1 to 10 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen atom,

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

In another embodiment, L < _{1 >} is a linear or branched ethylene group.

In one embodiment of the present disclosure, L < ₁ > is a substituted or unsubstituted linear or branched propylene group.

In one embodiment of the present disclosure, L < ₁ > is a substituted or unsubstituted branched chain propylene group.

In another embodiment, L < ₁ > is a propylene group substituted with a branched chain acrylate.

In one embodiment of the present disclosure, L < ₁ > is an isopropylene group substituted with (meth) acrylate.

In one embodiment of the present specification, R ₃ in Formula 1 is hydrogen.

In one embodiment of the present specification, R ₅ in Formula 1 is hydrogen.

In one embodiment of the present disclosure, n is one.

In one embodiment of this disclosure, the formula X is O.

The formula 1 may be derived from any one of the following formulas 1-1 to 1-8.

The compounds of Table 1 can be prepared in a structure including a carbazole group, a cyan group and an acrylic group by reacting a starting material containing a tertiary amine structure with a compound containing a cyan group and acrylic acid, for example, NCCH ₂ COOH. If necessary, additional acrylic groups can be introduced into the acrylic groups.

In one embodiment of the present invention, the maximum absorption wavelength (? _Max ) of the polymer is 400 nm to 500 nm.

In one embodiment of the present invention, the absorption spectrum of the polymer is in the range of 350 nm to 500 nm.

The transmittance in the wavelength range of 500 nm to 800 nm of the polymer in one embodiment of the present specification may be 90% to 100%.

The photosensitive resin composition according to one embodiment of the present disclosure includes a colorant containing the polymer.

In the case of a color filter using a pigment type photosensitive resin composition containing only conventional pigments, the number of pigments having absorption and transmission spectra suitable for a light source to be used is limited, and it is difficult to finely control absorption and transmission spectra. However, the coloring material according to one embodiment of the present specification can easily control the transmission spectrum finely.

In one embodiment of the present invention, the color material is a color material of a dye type including the polymer.

In one embodiment of the present invention, the color material comprises the polymer; And one or more additional colorants selected from the group consisting of pigments and dyes.

Specifically, the color material according to one embodiment of the present invention may use the polymer alone, or may use a pigment, a dye other than the polymer, or a mixture thereof in the polymer.

Specifically, in one embodiment, the color material is a mixed type colorant of a dye containing the polymer and a dye not containing the polymer. In another embodiment, the colorant is a hybrid type colorant of a salt / pigment comprising a dye containing the polymer and a pigment. In another embodiment, the color material is a hybrid type colorant of a dye containing the polymer, a dye / pigment not including the polymer, and a salt / pigment.

In the case of a color filter using a photosensitive resin composition containing a polymer according to an embodiment of the present invention, absorption and transmission spectra suitable for a light source to be applied can be obtained by using various dyes and pigments, High contrast ratio can be achieved.

As the black pigment, carbon black, graphite, metal oxide and the like can be used. Examples of carbon blacks are cysteine 5HIISAF-HS, cysto KH, cysteo 3HHAF-HS, cysteo NH, cysto 3M, cysto 300HAF-LS, cysto 116HMMAF-HS, , SISTO SOFEF, SISTO VGPF, SISTO SVHSRF-HS and SISTO SSRF (Donghae Carbon Co., Ltd.); Diagram Black II, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Diagram SF, Diagram N550M, Diagram M, Diagram E Diagram G Diagram R Diagram N760M Diagram LR, # 2700, # 25, # 45, # 45, # 45, # 45, # 45, # 25, # CF9, # 95, # 20, # 2300, # 2350, # 2300, # 2200, # 1000, # 980, # 900, 3030, # 3050, MA7, MA77, MA8, MA11, MA100, MA40, OIL7B, OIL9B, OIL11B, OIL30B and OIL31B (Mitsubishi Chemical); PRINTEX-25, PRINTEX-25, PRINTEX-55, PRINTEX-55, PRINTEX-45, PRINTEX-35, PRINTEX- 200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100 and LAMP BLACK-101 (Daegu; 890, RAVEN-880ULTRA, RAVEN-880ULTRA, RAVEN-850R, RAVEN-1080ULTRA, RAVEN-1080ULTRA, RAVEN-1080ULTRA, RAVEN-1080ULTRA, RAVEN-1040ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN- 820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN- RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, RAVEN-1170 (Colombia Carbon) or mixtures thereof. Examples of colored coloring materials include carmine 6B (CI12490), phthalocyanine green (CI 74260), phthalocyanine blue (CI 74160), perylene black (BASF K0084.K0086), cyanine black, lino yellow (CI 21090) Linol Yellow GRO (CI 21090), Benzidine Yellow 4T-564D, Victoria Pure Blue (CI42595), CI PIGMENT RED 3, 23, 97, 108, 122, 139, 140, 141, 142, 143, 144, 149, 166, 168, 175, 177, 180, 185, 189, 190, 192, 220, 221, 224, 230, 235, 242, 254, 255, 260, 262, 264, 272; C.I. PIGMENT GREEN 7, 10, 36, 37, 58; C.I. PIGMENT blue 1, 2, 1: 3, 2, 2: 1, 2: 2, 3, 8, 9, 10, 3, 15: 4, 15: 6, 16, 18, 19, 22, 24, 24: 1, 53, 56, 56: 1, 57, 58, 59, 60, 61, 62, 64; C.I. PIGMENT yellow 1, 2, 3, 4, 5, 6, 10,12, 13,14,15,16,17,18,20,24,31,32,34,35,35: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214; C.I. PIGMENT VIOLET 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50. White pigments and fluorescent pigments can also be used. As the phthalocyanine-based complex compound used as the pigment, a material having zinc as a central metal in addition to copper may be used.

In one embodiment of the present invention, the color material includes one or more additional color materials selected from the group consisting of the polymer, pigment and dye, and the weight ratio of the color material to the polymer is from 1:99 to 99: 1. In another embodiment, the weight ratio of the color material to the polymer is from 3:97 to 97: 3. In another embodiment, the weight ratio of the color material to the polymer is from 95: 5 to 5:95. There is an advantage that the transmittance is high within the above range.

In one embodiment of the present disclosure, the pigment may be PG58 or PY138.

In one embodiment of the present invention, the coloring material is composed of the pigment PG58 and the polymer.

In one embodiment of the present invention, the color material is composed of the pigments PG58 and PY138 and the polymer.

In one embodiment of the present invention, the dye has a solubility of 10% or more with respect to propylene glycol methyl ether acetate (PGMEA).

In one embodiment of the present invention, there is provided a photosensitive resin composition comprising the coloring material.

In one embodiment of the present invention, the photosensitive resin composition comprises a binder resin; Multifunctional monomers; Photoinitiators; 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 made of a photosensitive resin composition.

The binder resin may be a copolymer resin of a monomer having a multifunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility. The binder resin may further include a binder generally used in the art.

The multifunctional monomer which imparts the mechanical strength of the film is an unsaturated carboxylic acid ester; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters 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 Hydroxypropyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (Meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, CDI ethylene glycol (Meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) , Methyl [alpha] -hydroxymethyl acrylate, ethyl [alpha] -hydroxymethyl acrylate, propyl [alpha] -hydroxymethyl acrylate and butyl [alpha] -hydroxymethyl acrylate It is, but is not limited thereto.

Specific examples of the aromatic vinyl monomers include aromatic vinyl monomers such as styrene,? -Methylstyrene, (o, m, p) -vinyltoluene, (o, Styrene, but are not limited thereto.

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 imide are selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide and N-cyclohexylmaleimide But is not limited to these.

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

The alkali-solubilizing monomer 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, monomethyl maleic acid, 5-norbornene- (Meth) acryloyloxy) ethyl phthalate, mono-2 - ((meth) acryloyloxy) ethyl succinate, omega -carboxypolycaprolactone mono But it is not limited to these.

In one embodiment of the present invention, the acid value of the binder resin is 50 to 130 KOH mg / g, and the weight average molecular weight is 1,000 to 50,000.

The multifunctional monomer is a monomer that functions to form a photoresist phase by light. Specific examples thereof include propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxy ethylisocyanurate trimethacrylate, trimethyl 1, 2 or 3 groups selected from the group consisting of propane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexa methacrylate. Species or a mixture of two or more species.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to induce crosslinking. For example, the photoinitiator may be selected from the group consisting of an acetophenone compound, a nonimidazole compound, a triazine compound, It may be at least one selected.

The acetophenone compound may be at least one selected from the group consisting of 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl- (4-morpholinophenyl) -butan-1-one, or 2- (4-bromo-benzyl-2-dimethylamino- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, and the like.

Examples of the biimidazole-based compounds include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) 4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like , But is not limited thereto.

The triazine-based compound may be at least one selected from the group consisting of 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- (Trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl 2- {4- [2,4 Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2- epoxyethyl-2- {4- [ Yl] phenylthio} acetate, benzyl-2- {4- [2- (4-fluorophenyl) (Trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, 3- {chloro-4- [ (Phenylthio) propionic acid, 2,4- bis (trichloromethyl) -s-triazine-6-yl] Methyl) -6- p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like .

The oxime-based compound may be at least one selected from the group consisting of 1,2-octadione, -1- (4-phenylthio) phenyl, 2- (o-benzoyloxime) (Ciba Geigy, Shisei 124), ethanone, -Ethyl) -6- (2-methylbenzoyl-3-yl) -, 1- (O-acetyloxime) (Cajoo 242), N-1919 (Adeca), and the like.

The solvent is selected from the group consisting of 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 Cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethylhexanoate, 2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, Methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl It may be at least one selected from the group consisting of citrate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether. But is not limited thereto.

In one embodiment of the present invention, the content of the colorant including the polymer having the unit represented by the formula (1) is 5 wt% to 60 wt% based on the total weight of the solid content in the photosensitive resin composition, The content of the binder resin is 1 wt% to 60 wt%, the content of the initiator is 0.1 wt% to 20 wt%, and the content of the polyfunctional monomer is 0.1 wt% to 50 wt%.

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

In the above numerical range, a high-luminance green color filter can be obtained.

In one embodiment of the present invention, the photosensitive resin composition is selected from the group consisting of a photo-crosslinking agent, a curing accelerator, an adhesion promoter, a surfactant, an antioxidant, a thermal polymerization inhibitor, an ultraviolet absorber, an antioxidant, a dispersant and a leveling agent One or more additives.

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

The photo-crosslinking sensitizer may be at least one selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, Benzoate compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorene-based compounds such as 9-fluorenone, 2-chloro-9-proprenone and 2-methyl-9-fluorenone; Thioxanthone systems such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxytioxanthone, isopropylthioxanthone and diisopropylthioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; (9-acridinylpentane), 1,3-bis (9-acridinyl) propane, and the like Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide-based 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; (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis Amino-synergists such as methyl-cyclopentanone; (Diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl- -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- Pyran o [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylaminokalone and 4-azidobenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline, and the like.

As the curing accelerator, curing and mechanical strength are used, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2- mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate) (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) Nate) may be used.

Examples of the adhesion promoter used in the present invention include methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane , And at least one selected from the group consisting of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like as the alkyltrimethoxysilane can be used. You can choose to use it.

Specifically, the silicone surfactant is 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-370, BYK-370, BYK-380, and BYK-390 may be used as the fluorine-based surfactant, and DIC F-444, F-444, F-441, F-450, F-493, F-494, F-443, F-444, F-445 and F-446 of Dai Nippon Ink & , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F- TF-1116SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1025SF, TF- , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like.

The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid type heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; Butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t- butylphenyl) propionate, tetrabis [methylene- Butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di- 4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3- Hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-? -Naphthylamine, phenyl-? -Naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-? -Naphthyl- Secondary antioxidant; Thio such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethyl thiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] Secondary antioxidant; (2,4-ditbutylphenyl) pentaerythritol diphosphite or (1, 2,4-dibutylphenyl) pentaerythritol diphosphite or bis (2,4-dibutylphenyl) (1,1'-biphenyl) -4,4'-diisopropylphosphonic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] -Diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).

As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone may be used. Anything that is commonly used can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy (3-methyl-6-t-butylphenol), 2,2-dimethyl-2-pyrrolidone, But are not limited to, methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, And may include those generally known in the art.

The dispersant may be used either in a manner of internally adding to the pigment in the form of surface-treating the pigment in advance, or in a method of externally adding the pigment. As the dispersing agent, compound type, nonionic, anionic or cationic dispersing agent can be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic, amphoteric surfactants and the like. These may be used individually or in combination of two or more.

Specifically, the dispersing agent is selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, Alkyl amide alkylene oxide adducts, and alkyl amines, but are not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamide amine, reaction products of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing and non-polymer nitrogen- But are not limited to, compounds commonly used in the art may all be used.

In one embodiment of the present invention, there is provided a photosensitive material made of the photosensitive resin composition.

More specifically, the photosensitive resin composition of the present invention is applied onto a substrate by a suitable method to form a photosensitive material in the form of a thin film or a pattern.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and generally, a spin coating method is widely used. After the coating film is formed, a part of the residual solvent may be removed under reduced pressure as occasion demands.

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

The photosensitive resin composition according to the present invention can be used as a light-sensitive material for forming a black matrix of a thin-film transistor liquid crystal display (TFT LCD) or an organic light-emitting diode, , A photosensitive material for overcoat layer formation, a column spacer photosensitive material, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printing wiring board, and a photosensitive material for a plasma display panel (PDP) There is no restriction.

In one embodiment of the present invention, a color filter including the photosensitive material is provided.

The color filter may be manufactured using a photosensitive resin composition comprising a polymer containing units represented by the formula (1). The photosensitive composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.

The photosensitive resin composition according to one embodiment of the present invention provides a color filter having a high color reproducibility and a high luminance and a high contrast ratio even when the color filter is cured during the production of the color filter due to its excellent heat resistance and little change in color due to heat treatment .

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

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

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

Between the color pixels of the color filter, a lattice-shaped black pattern called a black matrix can be arranged for the purpose of improving the contrast. As the material of the black matrix, chromium can be used. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used. However, in consideration of high cost in the process, high reflectivity of chrome, and environmental pollution caused by a chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

The black matrix according to one embodiment of the present invention can use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone, or a mixture of carbon black and a color pigment may be used. In this case, since the color pigment having insufficient light shielding property is mixed, the strength of the film or the adhesion to the substrate is lowered There is an advantage not to be.

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

The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD) A liquid crystal display (LCD), and a cathode ray tube (CRT).

The display device according to one embodiment of the present invention has high color reproduction rate, high luminance and high contrast ratio, and high light-shielding property can be excellent. This feature makes it possible to manufacture the display device slimly.

Further, in one embodiment of the present invention, the display module itself can be made slim and the display can be maximized by using the upper and lower plate attachment portions of the module as a minimum area.

Hereinafter, the present invention will be described in detail with reference to examples. The following examples are intended to illustrate the present disclosure and the scope of the present disclosure includes the scope of the following claims and their substitutions and modifications, which are not intended to limit the scope of the embodiments.

<Production Example>

[Preparation of intermediate]

Compounds of Table 1 were prepared as shown in Schemes 1 to 8 below.

&Lt; Production Example 1-1 >

Polymers were polymerized using the following compounds.

- Compound of formula 1-1: 7.04 g

- BzMA (Benzyl methacrylate): 6.96 g

MMP (Methyl-3-methoxy propionate): 180.4 g

- 3-mercaptopropionic acid (CTA): 0.21 g

- Initiator (V-65): 0.56 g

Specifically, N ₂ was injected into the reactor at room temperature, and the compound of Formula 1-1, BzMA, and 3-mercaptopropionic acid, a chain transfer agent, were added to the solvent MMP and stirred for 30 minutes. The reaction was heated to 60 DEG C and when the reaction reached 60 DEG C, the initiator (V-65) dissolved in MMP was added to the reaction and stirred at 60 DEG C for 12 hours. As a result, a polymer having Mw = 8,500 and PDI = 2 was obtained.

&Lt; Production Examples 1-2 > to < Production Example 1-8 &

Was prepared in the same manner as in Preparation Example 1-1 except that the compound 1-2 to 1-8 was used instead of the compound of the formula 1-1. The amount of the compound used was as shown in Table 2 below.

Manufacturing example
1-2 Manufacturing example
1-3 Manufacturing example
1-4 Manufacturing example
1-5 Manufacturing example
1-6 Manufacturing example
1-7 Manufacturing example
1-8 The units of formula (1) The
1-2
7.04 g The
1-3
7.04 g The
1-4
7.04 g The
1-5
7.04 g The
1-6
7.04 g The
1-7
7.04 g The
1-8
7.04 g BzMA  6.96 g  6.96 g  6.96 g  6.96 g  6.96 g  6.96 g  6.96 g MMP 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 3-mercaptopropionic acid 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g Initiator
(V-65)  5.6 g  5.6 g  5.6 g  5.6 g  5.6 g  5.6 g  5.6 g Mw 8600 8400 8500 8700 8500 9000 9100 PDI 2.2 2.4 1.9 2.3 2 2.3 2.1

&Lt; Production example 2-1 >

Polymers were polymerized using the following compounds.

- Compound of formula 1-1: 7.09 g

- BzMA (Benzyl methacrylate): 4.25 g

- FA-513M: 2.66 g

MMP (Methyl-3-methoxy propionate): 180.4 g

- 3-mercaptopropionic acid (CTA): 0.21 g

- Initiator (V-65): 0.56 g

Specifically, N ₂ was injected into the reactor at room temperature, and the compound of Formula 1-1, BzMA, FA-513M and 3-mercaptopropionic acid as a chain transfer agent were added to the solvent MMP and stirred for 30 minutes. The reaction was heated to 60 DEG C and when the reaction reached 60 DEG C, the initiator (V-65) dissolved in MMP was added to the reaction and stirred at 60 DEG C for 12 hours. As a result, a polymer having Mw = 8600 and PDI = 2.1 was obtained.

&Lt; Preparation Examples 2-2 > to < Production Example 2-8 &

Was prepared in the same manner as in Production Example 2-1, except that the compound 1-2 to 1-8 was used instead of the compound of the formula 1-1. The amount of the compound used was as shown in Table 3 below.

Production example 2-2 Production Example 2-3 Production example 2-4 Production example 2-5 Production Example 2-6 Production example 2-7 Production example 2-8 The units of formula (1) The
1-2
7.09 g The
1-3
7.09 g The
1-4
7.09 g The
1-5
7.09 g The
1-6
7.09 g The
1-7
7.09 g The
1-8
7.09 g BzMA 4.25 g 4.25 g 4.25 g 4.25 g 4.25 g 4.25 g 4.25 g FA-513M 2.66 g 2.66 g 2.66 g 2.66 g 2.66 g 2.66 g 2.66 g MMP 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 3-mercaptopropionic acid 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g Initiator
(V-65) 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g Mw 8800 8700 8400 8600 8700 8900 9000 PDI 2 2.3 1.9 2.1 2.2 2.3 2

&Lt; Production example 3-1 >

Polymers were polymerized using the following compounds.

- Compound of formula 1-1: 7.01 g

- BzMA (Benzyl methacrylate): 4.08 g

- CHMA (Cyclohexyl methacrylate): 2.92 g

MMP (Methyl-3-methoxy propionate): 180.4 g

- 3-mercaptopropionic acid (CTA): 0.21 g

- Initiator (V-65): 0.56 g

Specifically, N ₂ was injected into the reactor at room temperature, and dye 1, BzMA, CHMA, 3-mercaptopropionic acid as a chain transfer agent were added to the solvent MMP, and the mixture was stirred for 30 minutes. The reaction was heated to 60 DEG C and when the reaction reached 60 DEG C, the initiator (V-65) dissolved in MMP was added to the reaction and stirred at 60 DEG C for 12 hours. As a result, a polymer having Mw = 8800 and PDI = 1.9 was obtained.

<Production Example 3-2> to <Production Example 3-8>

Was prepared in the same manner as in Production Example 3-1, except that the compound 1-2 to 1-8 was used instead of the compound of the formula 1-1. The amount of the compound used was as shown in Table 4 below.

Production example 3-2 Production Example 3-3 Production example 3-4 Production Example 3-5 Production Example 3-6 Production Example 3-7 Production Example 3-8 The units of formula (1) The
1-2
7.01 g The
1-3
7.01 g The
1-4
7.01 g The
1-5
7.01 g The
1-6
7.01 g The
1-7
7.01 g The
1-8
7.01 g BzMA 4.08 g 4.08 g 4.08 g 4.08 g 4.08 g 4.08 g 4.08 g CHMA 2.92 g 2.92 g 2.92 g 2.92 g 2.92 g 2.92 g 2.92 g MMP 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 3-mercaptopropionic acid 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g Initiator
(V-65) 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g Mw 8700 8800 8400 8500 8700 8800 9000 PDI 1.9 2.1 2.6 1.9 2.2 2.2 2.6

&Lt; Production example 4-1 >

Polymers were polymerized using the following compounds.

- Compound of formula 1-1: 7.08 g

- MAA (Methacrylic acid): 2.15 g

MMA (Methyl methacrylate): 4.77 g

MMP (Methyl-3-methoxy propionate): 180.4 g

- 3-mercaptopropionic acid (CTA): 0.21 g

- Initiator (V-65): 0.56 g

Specifically, N ₂ was injected into the reactor at room temperature, dye 1, MAA, MMA, 3-mercaptopropionic acid as a chain transfer agent were added to the solvent MMP, and the mixture was stirred for 30 minutes. The reaction was heated to 60 DEG C and when the reaction reached 60 DEG C, the initiator (V-65) dissolved in MMP was added to the reaction and stirred at 60 DEG C for 12 hours. As a result of Rm, a polymer having Mw = 8500, PDI = 2.1 and AV = 100 was obtained.

<Production Example 4-2> to <Production Example 4-8>

Was prepared in the same manner as in Production Example 4-1, except that the compound 1-2 to 1-8 was used instead of the compound of the formula 1-1. The amount of the compound to be used was as shown in Table 5 below.

Production example 4-2 Production Example 4-3 Production Example 4-4 Production Example 4-5 Production Example 4-6 Production Example 4-7 Production Example 4-8 The units of formula (1) The
1-2
7.08 g The
1-3
7.08 g The
1-4
7.08 g The
1-5
7.08 g The
1-6
7.08 g The
1-7
7.08 g The
1-8
7.08 g MAA 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g MMA 4.77 g 4.77 g 4.77 g 4.77 g 4.77 g 4.77 g 4.77 g MMP 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 3-mercaptopropionic acid 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g Initiator
(V-65) 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g Mw 8400 8800 8400 8500 8700 8800 9000 PDI 2.4 2.1 2.6 1.9 2.2 2.2 2.6 AV 100 100 100 100 100 100 100

&Lt; Production example 5-1 >

Polymers were polymerized using the following compounds.

- Compound of formula 1-1: 7.03 g

- MAA (Methacrylic acid): 2.15 g

- BzMA (Benzyl methacrylate): 4.83 g

MMP (Methyl-3-methoxy propionate): 180.4 g

- 3-mercaptopropionic acid (CTA): 0.21 g

- Initiator (V-65): 0.56 g

Specifically, N ₂ was injected into the reactor at room temperature, dye 1, MAA, BzMA, 3-mercaptopropionic acid as a chain transfer agent were added to the solvent MMP, and the mixture was stirred for 30 minutes. The reaction was heated to 60 DEG C and when the reaction reached 60 DEG C, the initiator (V-65) dissolved in MMP was added to the reaction and stirred at 60 DEG C for 12 hours. As a result, a polymer having Mw = 8700, PDI = 1.9, and AV = 100 was obtained.

<Production Example 5-2> to <Production Example 5-8>

Was prepared in the same manner as in Production Example 5-1 except that the compound 1-2 to 1-8 was used instead of the compound of the formula 1-1. The amount of the compound used was as shown in Table 6 below.

Production Example 5-2 Production example 5-3 Production Example 5-4 Production Example 5-5 Production Example 5-6 Production Example 5-7 Production Example 5-8 The units of formula (1) The
1-2
7.03 g The
1-3
7.03 g The
1-4
7.03 g The
1-5
7.03 g The
1-6
7.03 g The
1-7
7.03 g The
1-8
7.03 g MAA 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g BzMA 4.83 g 4.83 g 4.83 g 4.83 g 4.83 g 4.83 g 4.83 g MMP 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 3-mercaptopropionic acid 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g Initiator
(V-65) 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g Mw 8800 9000 8700 8800 9100 9400 9300 PDI 2.1 2.3 2.5 2.4 2.3 2.3 2.7 AV 100 100 100 100 100 100 100

&Lt; Production Example 6-1 >

Polymers were polymerized using the following compounds.

- Compound of formula 1-1: 8.12 g

- MAA (Methacrylic acid): 3.29 g

- BzMA (Benzyl methacrylate): 2.59 g

MMP (Methyl-3-methoxy propionate): 180.4 g

- 3-mercaptopropionic acid (CTA): 0.21 g

- Initiator (V-65): 0.56 g

- GMA (Glycidyl methacrylate): 2.15 g

- DMAP (4-dimethylaminopyridine): 0.04 g

- MEHQ: 0.01 g

(1) Linear Binder Polymerization

N ₂ was injected into the reactor at room temperature, dye 1, MAA, BzMA, and 3-mercaptopropionic acid, a chain transfer agent, were added to the solvent MMP and stirred for 30 minutes. The reaction was heated to 60 DEG C and when the reaction reached 60 DEG C, the initiator (V-65) dissolved in MMP was added to the reaction and stirred at 60 DEG C for 12 hours.

(2) Introduction of photoreactive group

The temperature of the reactor in which the linear binder was polymerized was increased to 80 ° C, and DMAP was introduced. MEHQ, a thermal polymerization inhibitor, was added and stirred for 30 minutes, then GMA was added, and the mixture was stirred at 115 ° C for 18 hours while maintaining the air atmosphere.

Mw = 9000 and PDI = 2.6. AV: 80

&Lt; Production Examples 6-2 > to < Production Example 6-8 &

Was prepared in the same manner as in Production Example 6-1, except that the compound 1-2 to 1-8 was used instead of the compound of the formula 1-1. The amount of the compound to be used was as shown in Table 7 below.

Production Example 6-2 Production example 6-3 Production Example 6-4 Production Example 6-5 Production Example 6-6 Production Example 6-7 Production Example 6-8 The units of formula (1) The
1-2
8.12 g The
1-3
8.12 g The
1-4
8.12 g The
1-5
8.12 g The
1-6
8.12 g The
1-7
8.12 g The
1-8
8.12 g MAA 3.29 g 3.29 g 3.29 g 3.29 g 3.29 g 3.29 g 3.29 g BzMA 2.59 g 2.59 g 2.59 g 2.59 g 2.59 g 2.59 g 2.59 g MMP 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 3-mercaptopropionic acid 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g Initiator
(V-65) 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g GMA 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g 2.15 g DMAP 0.04 g 0.04 g 0.04 g 0.04 g 0.04 g 0.04 g 0.04 g MEHQ 0.01 g 0.01 g 0.01 g 0.01 g 0.01 g 0.01 g 0.01 g Mw 9100 9500 9600 9300 9500 9000 9400 PDI 2.7 2.2 2.1 2.7 2.5 2.3 2.8 AV 80 80 80 80 80 80 80

&Lt; Production Example 7-1 >

Polymers were polymerized using the following compounds.

- Compound of formula 1-1: 7.59 g

- MAA (Methacrylic acid): 2.48 g

- CHMA (Cyclohexyl methacrylate): 3.93 g

MMP (Methyl-3-methoxy propionate): 180.4 g

- 3-mercaptopropionic acid (CTA): 0.21 g

- Initiator (V-65): 0.56 g

- GMA (Glycidyl methacrylate): 1.04 g

- DMAP (4-dimethylaminopyridine): 0.03 g

- MEHQ: 0.01 g

(1) Linear Binder Polymerization

N ₂ was injected into the reactor at room temperature, dye 1, MAA, CHMA and 3-mercaptopropionic acid as a chain transfer agent were added to the solvent MMP and stirred for 30 minutes. The reaction was heated to 60 DEG C and when the reaction reached 60 DEG C, the initiator (V-65) dissolved in MMP was added to the reaction and stirred at 60 DEG C for 12 hours.

(2) Introduction of photoreactive group

The temperature of the reactor in which the linear binder was polymerized was increased to 80 ° C, and DMAP was introduced. MEHQ, a thermal polymerization inhibitor, was added and stirred for 30 minutes, then GMA was added, and the mixture was stirred at 115 ° C for 18 hours while maintaining the air atmosphere.

Mw = 8900 and PDI = 2.0. AV: 115

<Production Example 7-2> to <Production Example 7-8>

Was prepared in the same manner as in Production Example 7-1, except that the compound 1-2 to 1-8 was used instead of the compound of the formula 1-1. The amount of the compound to be used was as shown in Table 8 below.

Production Example 7-2 Production Example 7-3 Production Example 7-4 Production Example 7-5 Production Example 7-6 Production Example 7-7 Production Example 7-8 The units of formula (1) The
1-2
7.59 g The
1-3
7.59 g The
1-4
7.59 g The
1-5
7.59 g The
1-6
7.59 g The
1-7
7.59 g The
1-8
7.59 g MAA 2.48 g 2.48 g 2.48 g 2.48 g 2.48 g 2.48 g 2.48 g CHMA 3.93 g 3.93 g 3.93 g 3.93 g 3.93 g 3.93 g 3.93 g MMP 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 3-mercaptopropionic acid 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g Initiator
(V-65) 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g 0.56 g GMA 1.04 g 1.04 g 1.04 g 1.04 g 1.04 g 1.04 g 1.04 g DMAP 0.04 g 0.04 g 0.04 g 0.04 g 0.04 g 0.04 g 0.04 g MEHQ 0.01 g 0.01 g 0.01 g 0.01 g 0.01 g 0.01 g 0.01 g Mw 9200 8800 9300 9700 9500 9000 9900 PDI 2.3 2.1 2.5 2.4 2.8 2.5 2.9 A.V 115 115 115 115 115 115 115

&Lt; Production example 8-1 >

Polymers were polymerized using the following compounds.

- Compound of formula 1-1: 8.20 g

- AMA (Allyl methacrylate): 5.80 g

MMP (Methyl-3-methoxy propionate): 180.4 g

- 3-mercaptopropionic acid (CTA): 0.21 g

- Initiator (V-65): 0.56 g

Specifically, N ₂ was injected into the reactor at room temperature, dye 1, BzMA, 3-mercaptopropionic acid as a chain transfer agent were added to the solvent MMP, and the mixture was stirred for 30 minutes. The reaction was heated to 60 DEG C and when the reaction reached 60 DEG C, the initiator (V-65) dissolved in MMP was added to the reaction and stirred at 60 DEG C for 12 hours. As a result, a polymer having Mw = 8,700 and PDI = 2.1 was obtained.

< Manufacturing example  8-2> to < Manufacturing example  8-8>

Was prepared in the same manner as in Production Example 8-1, except that the compound 1-2 to 1-8 was used instead of the compound of the formula 1-1. The amount of the compound to be used was as shown in Table 9 below.

Production Example 8-2 Production example 8-3 Production Example 8-4 Production Example 8-5 Production Example 8-6 Production example 8-7 Production Example 8-8 The units of formula (1) The
1-2
8.20 g The
1-3
8.20 g The
1-4
8.20 g The
1-5
8.20 g The
1-6
8.20 g The
1-7
8.20 g The
1-8
8.20 g AMA 5.80g 5.80g 5.80g 5.80g 5.80g 5.80g 5.80g MMP 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 180.4g 3-mercaptopropionic acid 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g 0.21 g Initiator
(V-65)  5.6 g  5.6 g  5.6 g  5.6 g  5.6 g  5.6 g  5.6 g Mw 8800 9000 9200 8700 9100 9700 9500 PDI 2.3 2 2.5 2.2 2 2.3 2.2

[Examples 1 to 10 and Comparative Examples 1 to 3]

A resin composition containing the materials shown in Table 10 below was prepared.

Type of color material Coloring matter
content
(wt%) bookbinder
Suzy
content
(wt%) MM
content
(wt%) additive
content
(wt%) Photoinitiator
content
(wt%) solvent
content
(wt%) Example 1 Polymer Production Example 1-1 33.24 35.10 17.26 0.68 1.40 12.32 Example 2 Polymer Production Example 1-3 Example 3 Polymer Preparation Example 1-7 Example 4 Polymer Production Example 5-1 33.33 35.10 17.26 0.68 1.40 12.23 Example 5 Polymer Production example 5-3 Example 6 Polymer Production Example 5-7 Example 7 Polymer Production example 6-1 29.12 35.10 17.26 0.68 1.40 16.44 Example 8 Polymer Production example 6-3 Example 9 Polymer Production Example 6-7 Example 10 Polymer Production Example 7-1 31.00 35.10 17.26 0.68 1.40 14.56 Example 11 Polymer Production Example 7-3 Example 12 Polymer Production Example 7-7 Comparative Example 1 Single molecule Colorant 9 1.200 35.10 17.26 0.68 1.40 44.36 Comparative Example 2 Single molecule Colorant 10 Comparative Example 3 Single molecule Coloring material 12 * Binder Resin: Copolymer of benzyl methacrylate and methacrylic acid, molar ratio 70:30, acid value 113 KOHmg / g, weight average molecular weight measured by GPC 20,000, molecular weight distribution (PDI) 2.0 , Solids content (SC) 25 wt%
* Solvent: PGMEA
* Photoinitiator: I-369 (BASF)
* MM (Multifunction monomer, polymeric compound): DPHA (Japanese explosive)
* Additive: DIC F-475

Heat resistance evaluation

The photosensitive resin composition is spin-coated on a glass (Corning) of 5 cm x 5 cm and pre-baked at 100 ° C for about 100 seconds to form a film. The substrate and the photomask were formed in the film (photo mask) and the 40mJ / cm ² exposure amount was examined and the distance between a 300㎛, using an exposure device (Hoya-shott社). The exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and post baked (PB) at 200 캜 for 20 minutes to obtain a color pattern.

A color pattern was obtained through a spectroscope (MCPD-Otsuka) to obtain a transmittance spectrum in a visible light range of 380 nm to 780 nm. The obtained transmittance spectrum and the C light source backlight are used and ΔEab is calculated using the obtained value E (L ^* , a ^* , b ^* ), and it is shown in Table 11 below.

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

The smaller value of? E means that the color change is small and the heat resistance is excellent.

PB1 times PB2 times Example 1 2.1 2.55 Example 2 2.08 2.5 Example 3 2.01 2.23 Example 4 2.2 2.65 Example 5 2.1 2.31 Example 6 2.07 2.12 Example 7 2.23 2.6 Example 8 2.37 2.55 Example 9 2.28 2.47 Example 10 2.44 2.85 Example 11 2.37 2.8 Example 12 2.44 2.84 Comparative Example 1 18.8 20.8 Comparative Example 2 15.3 16.5 Comparative Example 3 13.7 15.4 Eab value
- PB1 times: PB1 times - prB
- PB2 times: PB2 times - prB

Chemical resistance evaluation

The photosensitive resin composition is spin-coated on a glass (Corning) of 5 cm x 5 cm and pre-baked at 100 ° C for about 100 seconds to form a film. The substrate on which the film was formed was irradiated on the entire surface at an exposure dose of 40 mJ / cm ² using an exposure machine (Hoya-shott). The exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, post baked at 200 ° C for 20 minutes, cut into 1 cm x 5 cm and transferred to 20 g of NMP solution ).

NMP solution was measured by UV spectrum and Abs. The results are shown in Table 12 and Fig.

Abs Example 1 0.045 Example 2 0.044 Example 10 0.035 Example 11 0.032 Comparative Example 1 0.23 Comparative Example 2 0.233

As shown in the above table, the polymer type color material according to the present invention is superior to the monomolecular type color material used in the comparative example in terms of heat resistance and chemical resistance.

The chemical resistance Test Abs value in FIG. 1 indicates chemical resistance. When the Abs value is small, the chemical resistance is excellent, and when it is large, the chemical resistance is weak. In other words, if the chemical resistance is excellent, the absent amount of the coloring material in the NMP solution is small and the Abs value is small. If the chemical resistance is poor, the absorption amount of the coloring material in the NMP solution is large.

The transmittance spectra of the polymers prepared in Production Examples 1-1, 1-3 and 1-7 are shown in Fig.

Examples 13 to 15 and Comparative Example 3 - Comparison of color compositions of green photosensitive resin composition

A green photosensitive resin composition was prepared using the materials shown in Table 13 below.

Example 13 Example 14 Example 15 Comparative Example 3 Coloring matter G58 3.825 3.672 3.774 3.06 G138 0.918 1.071 0.51 2.04 Production Example 1-1 10.15269 0 0 0 Production Example 1-3 - 10.15269 0 0 Preparation Example 1-7 - 0 23.20616 0 Binder resin 17.84109 17.84109 17.84109 17.84109 Photoinitiator 1.19 1.19 1.19 1.19 additive 0.00391 0.00391 0.00391 0.00391 Multifunctional monomers 5.865 5.865 5.865 5.865 solvent 60.20431 60.20431 47.60984 70 Total content 100 100 100 100 - expressed in weight ratio
- Binder resin: copolymer of benzyl methacrylate and methacrylic acid, molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight measured by GPC 20,000, molecular weight distribution (PDI ) 2.0, solid content (SC) 25%
- Solvent: Propylene glycol monomethyl ether acetate (PGMEA)
Photoinitiator: I-369 (BASF)
Polyfunctional monomer: diphenyl pentaerythritol hexaacrylate (DPHA)
- Production Example Coloring matter content: 3.516308% (weight ratio of colorant in total)

A film was formed using the compositions prepared in Examples 13 to 15 and Comparative Example 3, and the luminance was measured and shown in Table 14 below.

Gx Gy Y Comparative Example 3 0.280 0.565 62.1 Example 13 0.282 0.565 62.7 Example 14 0.279 0.565 62.3 Example 15 0.284 0.565 62.9

3 shows the transmittance spectra of Example 15 and Comparative Example 3. The increase in luminance of Example 15 was due to the increase in the transmittance of Example 15 (salt and pigment type) compared to Comparative Example 3 (pigment type) at 450-680 nm.

Claims (11)

Binder resin; Multifunctional monomers; Photoinitiators; menstruum; And
1. A resin composition comprising a polymer comprising a unit represented by the following formula (1).
[Chemical Formula 1]

In Formula 1,
n is an integer of 1 to 3,
m is an integer of 1 to 4,
X is NR or O,
R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; And a substituted or unsubstituted C2 to C25 alkenyl group,
L ₁ is a direct bond; Or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
L ₂ is a direct bond; A substituted or unsubstituted alkylene group having 1 to 25 carbon atoms; Or a substituted or unsubstituted carbonyl group having 1 to 40 carbon atoms,
R ₁ and R ₂ are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted 7 to 50 aralkyl group; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,
R ₃ is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,
R ₄ and R ₅ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1 to C25 alkoxy group; A substituted or unsubstituted C2 to C25 alkenyl group; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,
R ₆ to R ₈ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms. The resin composition according to claim 1, wherein the polymer further comprises at least one unit selected from the following formulas (2) to (9).
(2)

In Formula 2,
R ₉ to R ₁₁ are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,
R ₁₂ is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms.
(3)

In Formula 3,
R ₁₃ , R ₁₅ and R ₁₆ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,
R ₁₄ is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms or a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms.
[Chemical Formula 4]

In Formula 4,
R ₁₇ , R ₁₉ and R ₂₀ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,
R ₁₈ is a substituted or unsubstituted (meth) acrylalkyl group having 5 to 25 carbon atoms.
[Chemical Formula 5]

In Formula 5,
R ₂₁ to R ₂₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms.
[Chemical Formula 6]

In Formula 6,
R ₂₅ to R ₂₇ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms.
(7)

In Formula 7,
R ₂₈ and R ₂₉ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,
R ₃₀ is an alkyl group having 1 to 25 carbon atoms; Or an alkyl ester group having 2 to 25 carbon atoms.
[Chemical Formula 8]

In Formula 8,
R ₄₁ to R ₄₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,
R ₄₄ is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; Or a substituted or unsubstituted C2 to C25 alkenyl group having 5 to 20 carbon atoms.
[Chemical Formula 9]

In Formula 9,
R ₅₁ to R ₅₃ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C1 to C25 alkoxy group,
L ₇ is -C (= O) - or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms,
L ₈ is a substituted or unsubstituted alkenylene group having 2 to 25 carbon atoms, methylene, ethylene or propylene. The resin composition according to claim 1, wherein the formula (1) is represented by the following formula (11):
(11)

In the above formula (11), the description of the substituent is as shown in formula (1). The resin composition according to claim 1, wherein the polymer has a weight average molecular weight of 1,000 to 30,000. The resin composition according to claim 1, wherein the PDI of the polymer is 1 to 3. The resin composition according to claim 1, wherein the polymer has an acid value of 0 to 200 KOH mg / g. delete The method according to claim 1,
Based on the total weight of the solid content in the resin composition
The content of the colorant including the polymer containing the unit of the formula (1) is 5 wt% to 60 wt%
The content of the binder resin is 1 wt% to 60 wt%
The content of the photoinitiator is 0.1 wt% to 20 wt%
And the content of the polyfunctional monomer is 0.1 wt% to 50 wt%. A photosensitive material produced using the resin composition according to any one of claims 1 to 6 and 8. A color filter comprising the photosensitive material of claim 9. A display device comprising the color filter of claim 10.

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