KR102268233B1 - Compound, polymer, colorant composition, resin composition, photo resist, color filter and display device - Google Patents

Abstract

The present specification provides a compound represented by Formula 1, a polymer, a photosensitive resin composition comprising the same, a photosensitive material, a color filter, and a display device.

Description

Compound, polymer, color material composition, resin composition, photosensitive material, color filter and display device {COMPOUND, POLYMER, COLORANT COMPOSITION, RESIN COMPOSITION, PHOTO RESIST, COLOR FILTER AND DISPLAY DEVICE}

The present specification relates to a compound, a polymer, a color material composition, a resin composition, a photosensitive material, a color filter, and a display device.

Recently, instead of a conventional cold cathode tube (CCFL) as a light source for a liquid crystal display (LCD), an LED (Light Emitting Diode) or OLED (Organic Light Emitting Iode) device that emits light without driving or liquid crystal has been widely used. When the LED or OLED is used as a light source, a separate color filter is not required because red, green, and blue light is emitted by itself. Accordingly, in order to manufacture thin-film displays and flexible displays, products using secondary light emission, such as LEDs and OLEDs from which the curli filter is removed, as unit pixels, are being developed and produced.

However, in the case of a display using LEDs and OLEDs as unit pixels, it is difficult to enlarge the area, and it is not easy to match or adjust the required color coordinates using the light emitted from the LED or OLED light source. Therefore, in order to realize a desired color, a light source and an appropriate curli filter are required, and a pigment dispersion method using a pigment as a colorant is generally applied.

However, in the case of a pigment dispersion, the pigment not only scatters light because it exists in a particle state, but also rapidly increases the surface area of the pigment due to the refinement of the pigment, resulting in non-uniform pigment particles being generated due to deterioration of dispersion stability. There is this.

Therefore, the use of dyes as colorants to achieve high luminance, high contrast ratio and high resolution has been studied. Among them, xanthene dyes are widely used as red colorants. In general, xanthene dyes have a good slope and high absorbance in the range of 500 nm to 550 nm, so they are effective for color characteristics. However, due to higher solubility than pigments, chemical resistance and low heat resistance has the disadvantage of having

Korean Patent Publication No. 2001-0009058

The present specification provides a compound, a polymer, a color material composition, a resin composition, a photosensitive material, a color filter, and a display device.

An object of the present invention is to provide a photosensitive material, a color filter, etc. having excellent chemical resistance and heat resistance by using the color material composition containing the compound of Formula 1 of the present invention in a color filter.

An exemplary embodiment of the present specification provides a compound represented by Formula 1.

[Formula 1]

In Formula 1,

L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, Formula 1-A; Or represented by the following formula 1-B,

R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r1 and r2 are each an integer of 1 to 3,

r3 is an integer from 1 to 4,

When r1 to r3 are 2 or more, two or more R1 to R3 are the same as or different from each other,

X1 is represented by the following formula 1-A,

X2 is represented by the following formula 1-B,

[Formula 1-A]

[Formula 1-B]

In Formula 1-A and Formula 1-B,

Q1 and Q2 are the same as or different from each other, and each independently O; or NH;

L101 and L102 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

A1 is hydrogen; heavy hydrogen; nitro group; nitrile group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkoxy group,

a1 is an integer from 1 to 5,

When a1 is 2 or more, two or more A1s are the same as or different from each other,

B1 is any one selected from the following structures,

In the structure,

L201 is a direct bond; or O;

R201 to R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r202 is an integer from 1 to 3,

r203 is an integer from 1 to 5,

When r202 and r203 are each 2 or more, two or more R202 and R203 are the same or different from each other,

* means the part to be connected.

An exemplary embodiment of the present specification provides a polymer including the compound represented by Formula 1 as a monomer.

An exemplary embodiment of the present specification provides a color material composition comprising the compound represented by Formula 1 above.

An exemplary embodiment of the present specification includes a compound represented by Formula 1; binder resin; polyfunctional monomers; And it provides a resin composition comprising a photoinitiator.

An exemplary embodiment of the present specification provides a photosensitive material including the resin composition or cured product.

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

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

The compound represented by Formula 1 according to an exemplary embodiment of the present specification has excellent solubility in a solvent, and excellent heat resistance and chemical resistance.

In addition, according to an exemplary embodiment of the present specification, the color material composition including the compound represented by Formula 1 has a characteristic of high luminance compared to the case of using a conventional pigment.

In addition, according to an exemplary embodiment of the present specification, a high-contrast color filter having excellent heat resistance and chemical resistance may be manufactured using the color material composition including the compound represented by Formula 1 above.

In addition, according to an exemplary embodiment of the present specification, when the color material composition including the compound represented by Formula 1 is used, there is an effect of cost reduction because it is not necessary to proceed with the dispersion process necessary when applying the existing pigment.

The compound represented by Chemical Formula 1 of the present specification has a structure including at least one aryl group and at least one curable group each having an electron withdrawing group or an electron donating group as a substituent. Compared to a structure including only one of an aryl group and a curable group, heat resistance is improved, and dye transfer and dissolution, which are weak points of dye, can be suppressed. Therefore, a high-contrast color filter having excellent heat resistance and chemical resistance can be manufactured by using the color material composition including the compound represented by Formula 1 of the present specification.

In addition, if the color material composition including the compound represented by Formula 1 of the present specification is used, there is an effect of cost reduction because it is not necessary to proceed with the dispersion process necessary when applying the existing pigment.

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

The present specification provides a compound represented by Formula 1 above.

When the xanthene dye of the present invention has a curable group represented by B1 of the formula (1) in its structure, the xanthene dyes can react with each other by radicals or heat. In addition, the xanthene dye can react with the polymerizable compound, alkali-soluble resin, binder resin, etc. contained in the composition of the present invention. When the reaction occurs, the xanthene dye is firmly fixed in the cured film, resulting in improved heat resistance and chemical resistance.

In addition, since the xanthene dye of the present invention has an electron withdrawing group or an electron donating group in its structure, fine control (tuning) of the energy level becomes possible. Through this, it is possible to reduce the fluorescence intensity and as a result achieve a high contrast ratio.

In the present specification, when a part "includes" a certain component, this means that other components may be further included, rather than excluding other components, unless otherwise stated.

Examples of the substituents of the compound represented by Formula 1 are described below, but are not limited thereto.

In the present specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent is substitutable, When two or more substituents are substituted, two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; -COOH; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; aryl group; heteroaryl group; and one or more substituents selected from the group comprising a heterocyclic group containing one or more of N, O, S or Se atoms or two of the above exemplified substituents are substituted with a linked group, or does not have any substituents .

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

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 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-ox tyl group, and the like, but is not limited thereto.

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

In the present specification, the alkoxy group _{may be represented by -OR a} , and may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 25. As a specific example, an alkenyl group substituted with an aryl group such as a stylbenyl group or a styrenyl group is preferable, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20, and may be 6 to 10. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

In the present specification, the heteroaryl group includes one or more atoms other than carbon, that is, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; furanyl group; pyrrole group; imidazolyl group; thiazolyl group; oxazolyl group; oxadiazolyl group; pyridyl group; bipyridyl group; pyrimidyl group; triazinyl group; triazolyl group; acrydyl group; pyridazinyl group; pyrazinyl group; quinolinyl group; quinazolinyl group; quinoxalinyl group; phthalazinyl group; pyridopyrimidyl group; pyridopyrazinyl group; pyrazino pyrazinyl group; isoquinolinyl group; indolyl group; carbazolyl group; benzoxazolyl group; benzimidazolyl group; benzothiazolyl group; benzocarbazolyl group; benzothiophene group; dibenzothiophene group; benzofuranyl group; a phenanthrolinyl group; isoxazolyl group; thiadiazolyl group; phenothiazinyl group; and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the alkylene group means that the alkyl group has two bonding positions, that is, a divalent group. Except that each of these groups is a divalent group, the description of the alkyl group described above may be applied.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except for non-monovalent ones.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C1-C30 alkylene group; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C 1 to C 20 alkylene group; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C 1 to C 10 alkylene group; or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; a substituted or unsubstituted propylene group; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; methylene group; or an ethylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; methylene group; or an ethylene group.

In one embodiment of the present specification, L1 and L2 are a direct bond.

In an exemplary embodiment of the present specification, L3 and L4 are ethylene groups.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, Formula 1-A; Or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a substituted or unsubstituted C 1 to C 30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or the following formula 1-A; Or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a substituted or unsubstituted C 1 to C 20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or the following formula 1-A; Or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a substituted or unsubstituted C 1 to C 10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or the following formula 1-A; Or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isopropyl group; Or a substituted or unsubstituted phenyl group, Formula 1-A; Or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a methyl group in which a phenyl group is substituted or unsubstituted; an ethyl group unsubstituted or substituted with a hydroxyl group; Profile group; isopropyl group; Or a phenyl group, Formula 1-A; Or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an ethyl group, or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, Ar1 is a hydroxyl group; methyl group; a methyl group substituted with a phenyl group; ethyl group; an ethyl group substituted with a hydroxyl group; Profile group; isopropyl group; Or a phenyl group, Formula 1-A; Or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, Ar2 is a methyl group; a methyl group substituted with a phenyl group; ethyl group; Profile group; isopropyl group; Or a phenyl group, Formula 1-A; Or represented by the following formula 1-B.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; hydroxyl group; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; hydroxyl group; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; hydroxyl group; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C12 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R3 are hydrogen.

In an exemplary embodiment of the present specification, r1 and r2 are each an integer of 1 to 3, r3 is an integer of 1 to 4, and when r1 to r3 are 2 or more, two or more R1 to R3 are the same as or different from each other, respectively. Do.

In an exemplary embodiment of the present specification, r1 is an integer of 1 to 3.

In an exemplary embodiment of the present specification, r1 is 3.

In one embodiment of the present specification, r2 is an integer of 1 to 3.

In one embodiment of the present specification, r2 is 3.

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

In one embodiment of the present specification, r3 is 4.

In an exemplary embodiment of the present specification, X1 is represented by the following formula 1-A.

In an exemplary embodiment of the present specification, X2 is represented by the following formula 1-B.

[Formula 1-A]

[Formula 1-B]

In Formula 1-A and Formula 1-B,

Q1 and Q2 are the same as or different from each other, and each independently O; or NH.

In an exemplary embodiment of the present specification, Q1 and Q2 are O.

In an exemplary embodiment of the present specification, Q1 and Q2 are NH.

In one embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C1-C30 alkylene group; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C 1 to C 20 alkylene group; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C 1 to C 10 alkylene group; or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

In one embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted methylene group; or a substituted or unsubstituted ethylene group.

In one embodiment of the present specification, L101 and L102 are the same as or different from each other, and each independently a direct bond; methylene group; or an ethylene group.

In one embodiment of the present specification, L101 is a direct bond.

In an exemplary embodiment of the present specification, L102 is a methylene group; or an ethylene group.

In the compound of the present invention, A1, which is an electron withdrawing group or an electron donating group, is substituted in the aryl group to fine-tune the energy level, thereby reducing the fluorescence intensity. Specifically, in the case of an excited fluorephore, one electron is located in the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO). It is located at a lower energy level or higher than the LUMO of the fluorophore. At this time, as electrons move from the LUMO level to the HOMO level of the fluorophore, light is emitted and the fluorescence intensity is increased. On the other hand, when an electron withdrawing group or an electron donating group is substituted for the benzene ring, the HOMO level of the benzene ring is located between the LUMO and HOMO of the fluorophore. Therefore, electron transfer from the LUMO level to the HOMO level of the fluorophore is suppressed, and the fluorescence intensity can be reduced compared to the unsubstituted benzene ring.

In an exemplary embodiment of the present specification, A1 is hydrogen; heavy hydrogen; nitro group; nitrile group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

In an exemplary embodiment of the present specification, A1 is hydrogen; heavy hydrogen; nitro group; nitrile group; halogen group; hydroxyl group; a substituted or unsubstituted C 1 to C 30 alkyl group; or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, A1 is hydrogen; heavy hydrogen; nitro group; nitrile group; halogen group; hydroxyl group; a substituted or unsubstituted C 1 to C 10 alkyl group; or a substituted or unsubstituted C 1 to C 10 alkoxy group.

In an exemplary embodiment of the present specification, A1 is hydrogen; heavy hydrogen; nitro group; nitrile group; halogen group; hydroxyl group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted methoxy group; a substituted or unsubstituted ethoxy group; a substituted or unsubstituted propoxy group; Or a substituted or unsubstituted butoxy group.

In an exemplary embodiment of the present specification, A1 is hydrogen; nitro group; nitrile group; fluorine; Goat; hydroxyl group; methyl group; tert-butyl group; or a methoxy group.

In an exemplary embodiment of the present specification, A1 is a nitro group.

In the exemplary embodiment of the present specification, a1 is an integer of 1 to 5, and in the case of 2 or more, 2 or more A1s are the same or different from each other.

In one embodiment of the present specification, a1 is an integer of 1 to 3.

In one embodiment of the present specification, a1 is 1 or 2.

In an exemplary embodiment of the present specification, a1 is 1.

The compound of the present invention has a curable group, so that the xanthene dyes can react with each other by radicals or heat. In addition, the xanthene dye can react with the polymerizable compound, alkali-soluble resin, binder resin, etc. contained in the composition of the present invention. When the reaction occurs, the xanthene dye is firmly fixed in the cured film, resulting in improved heat resistance and chemical resistance.

In one embodiment of the present specification, B1 is any one selected from the following structures.

In the structure,

L201 is a direct bond; or O.

In one embodiment of the present specification, L201 is a direct bond.

In the exemplary embodiment of the present specification, L201 is O.

In an exemplary embodiment of the present specification, R201 to R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R201 to R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R201 to R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R201 to R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R201 to R203 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted methyl group; or a substituted or unsubstituted ethylene group.

In an exemplary embodiment of the present specification, R201 to R203 are the same as or different from each other, and each independently hydrogen; methyl group; or an ethylene group substituted with a methyl group.

In an exemplary embodiment of the present specification, R201 is an ethylene group substituted with a methyl group.

In an exemplary embodiment of the present specification, R202 is hydrogen.

In an exemplary embodiment of the present specification, R203 is hydrogen; or a methyl group.

In an exemplary embodiment of the present specification, r202 is an integer of 1 to 3, and when r202 is 2 or more, two or more R202 are the same as or different from each other.

In one embodiment of the present specification, r203 is an integer of 1 to 5, and when r203 is 2 or more, two or more R203 are the same or different from each other.

In one embodiment of the present specification, B1 is any one selected from the following structures.

* means the part to be connected.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of Chemical Formulas 2-1 to 2-7 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-1 to 2-7,

L1 to L4, R1 to R3, r1 to r3, Q1, Q2, L101 and L102 are as defined in Formula 1 above,

Ar11 and Ar12 are the same as or different from each other, and each independently represents a hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

Q3 to Q6 are the same as or different from each other, and each independently O; or NH;

A11 to A13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitro group; nitrile group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkoxy group,

a11 to a13 are the same as or different from each other, and each independently an integer of 1 to 5,

When a11 to a13 are two or more, two or more A11 to A13 are the same as or different from each other,

L103 to L106 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

B11 to B13 are the same as or different from each other, and each independently any one selected from the following structures,

In the structure,

L201 is a direct bond; or O;

R201 to R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r202 is an integer from 1 to 3,

r203 is an integer from 1 to 5,

When r202 and r203 are each 2 or more, two or more R202 and R203 are the same or different from each other,

* means the part to be connected.

In the exemplary embodiment of the present specification, Ar11 and Ar12 have the same definitions as Ar1 and Ar2.

In the exemplary embodiment of the present specification, Q3 to Q6 have the same definitions as Q1 and Q2.

In the exemplary embodiment of the present specification, L103 to L106 are the same as the definitions of L101 and L102.

In the exemplary embodiment of the present specification, B11 to B13 are the same as the definition of B1.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas, but is not necessarily limited thereto.

The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below. In the following preparations, representative examples are described, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, etc. can be changed.

For example, the compound represented by Formula 1 may be prepared as shown in Formula 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art. A substituent may be bonded as in the following general formula 1, but is not limited thereto.

[General formula 1]

In Formula 1, the definitions of L1 to L4, Ar1, Ar2, A1 and B1 are the same as defined in Formula 1 above. Although R1 to R3 and additional A1 are not shown in Formula 1, the substituent may be substituted by using a reactant in which the substituent is substituted or by a method known in the art for a product produced by Formula 1 have.

An exemplary embodiment of the present specification provides a polymer comprising the compound represented by Formula 1 as a monomer.

The monomer refers to a substance that becomes a unit when making a polymer compound through a chemical reaction.

The polymer refers to a compound made by polymerizing the monomer, and refers to a high molecular compound.

In an exemplary embodiment of the present specification, the polymer may further include a monomer in addition to including the compound represented by Formula 1 as a monomer. For example, it may further include a monomer or a polyfunctional monomer included in the following binder resin as a monomer.

In an exemplary embodiment of the present specification, the weight average molecular weight of the polymer including the compound represented by Formula 1 as a monomer may be 5,000 to 30,000 g/mol.

The weight average molecular weight is one of the average molecular weights for which the molecular weight is not uniform and the molecular weight of a certain polymer material is used as a reference, and is a value obtained by averaging the molecular weights of component molecular species of a polymer compound having a molecular weight distribution by weight fraction.

The weight average molecular weight may be measured through Gel Permeation Chromatography (GPC) analysis.

According to an exemplary embodiment of the present specification, there is provided a color material composition comprising the compound represented by Formula 1 above.

The color material composition may further include at least one of a dye and a pigment in addition to the compound represented by Formula 1 above. For example, the color material composition may include only the compound represented by Formula 1, but includes the compound represented by Formula 1 and one or more dyes, or includes the compound represented by Formula 1 and one or more pigments, or , may include a compound represented by Formula 1, at least one dye, and at least one pigment. In one embodiment of the present specification, there is provided a resin composition comprising the color material composition.

According to an exemplary embodiment of the present specification, the dye is at least one dye selected from a xanthene dye, a cyanine dye, an anthraquinone dye, an azaporphyrin dye, and an azo metal complex, and the pigment is a red pigment.

The xanthene dye, cyanine dye, anthraquinone dye, azaporphyrin dye, and azo metal complex are not particularly limited as long as they are used in the art.

The red pigment is not limited as long as it is used in the art, and among them, naphthol azo-based, diketopyrrolopyrrole-based, and anthraquinone-based red pigments may be included. Examples of the red pigment may include compounds classified as pigments in the color index. Specific examples include Pigment red 177, 254, 269, and the like.

In one embodiment of the present specification, the resin composition comprises a binder resin; polyfunctional monomers; A photoinitiator may be included.

In one embodiment of the present specification, the resin composition comprises a binder resin; polyfunctional monomers; photoinitiators; and additives.

In one embodiment of the present specification, the resin composition comprises a binder resin; polyfunctional monomers; photoinitiators; and solvents.

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 the resin composition.

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

In an exemplary embodiment of the present specification, the binder resin is a copolymer of a polyfunctional monomer.

The polyfunctional monomer imparting the mechanical strength of the membrane is unsaturated carboxylic acid esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and an acid anhydride.

In one embodiment of the present specification, the binder resin is unsaturated carboxylic acid esters; aromatic vinyls; and at least one monomer selected from the group of unsaturated imides.

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 (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydropuffril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy Cydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth) ) acrylate, p-nonylphenoxypolyethylene glycol (meth)acrylate, p-nonylphenoxypolypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl (meth)acrylate, tribromophenyl (meth) ) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but only It is not limited.

Specific examples of the aromatic vinyl include styrene, α-methylstyrene, (o,m,p)-vinyl toluene, (o,m,p)-methoxy styrene, and (o,m,p)-chloro styrene. It may be selected from the group consisting of, but is not limited thereto.

Specific examples of the unsaturated ethers may be 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-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. may be, but is not limited thereto.

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

The monomer imparting alkali solubility is not particularly limited as long as it contains an acid group, and for example, (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, ω-carboxy polycaprolactone mono(meth)acrylate selected from the group consisting of It is preferable to use one or more types, but is not limited thereto.

According to an exemplary 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 g/mol to 50,000 g/mol.

The polyfunctional monomer is a monomer that forms a photoresist image by light, and specifically, 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, trishydroxyethyl isocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate species or a mixture of two or more species.

The photoinitiator is not particularly limited as long as it is an initiator that triggers crosslinking by generating radicals by light, for example, selected from the group consisting of acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds. There may be more than one type.

The acetophenone-based compound is 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-hydroxycyclohexylphenyl ketone, benzoinmethyl ether, benzoinethyl 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-1-(4-morpholinophenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, and the like.

As the biimidazole-based compound, 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4 ,4',5,5'-tetrakis (3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl)-4, 4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. , but not limited thereto.

The triazine-based compound is 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-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-triazine-6 -yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, benzyl-2-{4-[ 2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazine-6 -yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionamide, 2,4-bis(trichloro methyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3,-butadienyl-s -triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but are not limited thereto.

The oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Ciba Geigisa, SI 124), ethanone, -1- (9 -ethyl)-6-(2-methylbenzoyl-3-yl)-,1-(O-acetyloxime) (CGI 242), N-1919 (Adecas), and the like, but is not limited thereto.

The solvent is 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-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 -Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy It may be at least one selected from the group consisting of propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but is not limited thereto.

According to an exemplary embodiment of the present specification, based on 100 parts by weight of the total weight of the solid content in the resin composition, the content of the compound represented by Formula 1 is greater than 0 parts by weight to 30 parts by weight; 0.00001 parts by weight to 15 parts by weight; 0.00001 parts by weight to 10 parts by weight; 0.0001 parts by weight to 5 parts by weight; or 0.00001 parts by weight to 3 parts by weight.

According to an exemplary embodiment of the present specification, based on 100 parts by weight of the total weight of the solid content in the resin composition, the content of the binder resin is 1 part by weight to 60 parts by weight, and the content of the photoinitiator is 0.1 parts by weight to 20 parts by weight, The content of the polyfunctional monomer is 0.1 parts by weight to 60 parts by weight.

The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition. The solid content and the basis of parts by weight based on the solid content of each component may be measured by general analysis means used in the art, such as liquid chromatography or gas chromatography.

According to an exemplary embodiment of the present specification, the content of the solvent is 100 parts by weight to 300 parts by weight based on 100 parts by weight of the total weight of the solid content in the resin composition.

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

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

According to an exemplary embodiment of the present specification, the resin composition is selected from the group consisting of a photocrosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent Add 1 or 2 or more additives include as

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

The photocrosslinking sensitizer is benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; fluorenone compounds such as 9-fluorenone, 2-chloro-9-prorenone, and 2-methyl-9-fluorenone; Thioxanthone type, such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, diisopropyl thioxanthone compound; xanthone-based 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-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, etc. 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 compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; benzoate compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzoyl-7-(diethylamino)coumarin, 3 -benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo coumarin-based compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; At least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline may be used.

The curing accelerator is used to increase curing and mechanical strength, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzooxazole, 2,5-dimercapto-1,3 ,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol Erythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2-mercaptoacetate), and trimethylolpropane-tris(3-mercaptopropio) nate) may be used at least one selected from the group consisting of.

The adhesion promoter used herein includes methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, and methacryloyloxy propyldimethoxysilane. It is possible to select and use at least one type of methacryloyl silane coupling agent such as, and at least one type of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc. as the alkyl trimethoxysilane. You can choose to use it. Adhesion promoters are also called adhesion aids.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used. (DaiNippon 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-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. may be used, but is not limited thereto.

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

Specific examples of the antioxidant include phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetrabis[methylene-3-(3, 5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxy benzyl)benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis(4-methyl-6-t-butylphenol), 2,6-g, t-Butylphenol 4,4'-butylidene-bis(3-methyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol) or bis[3 ,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol ester), such as a hindered phenol-based primary antioxidant; amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N′-diphenyl-p-phenylenediamine or N,N′-di-β-naphthyl-p-phenylenediamine secondary antioxidants; Thio such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane secondary antioxidants; or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl) -4,4'-diylbisphosphonoic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4' -Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester) may be mentioned as a phosphite-based secondary antioxidant.

As the ultraviolet absorber, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but the present invention is not limited thereto. All commonly used ones can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy Amine 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 may include one or more selected from the group consisting of phenothiazine (phenothiazine), but is not limited thereto. may include those generally known in the art.

The dispersant may be used as a method of internally adding the pigment to the pigment in the form of surface treatment in advance, or a method of externally adding the pigment to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and fluorine-based, ester-based, cationic, anionic, nonionic, and amphoteric surfactants may be mentioned. These may be used individually or in combination of 2 or more types.

Specifically, the dispersant is polyalkylene glycol and its esters, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylate esters, carboxylates, There is at least one selected from the group consisting of an alkylamide alkylene oxide adduct and an alkylamine, but is not limited thereto.

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

According to an exemplary embodiment of the present specification, there is provided a photosensitive material including the resin composition or a cured product thereof.

More specifically, the resin composition of the present specification is applied on a substrate by an appropriate method to form a thin film or patterned photosensitive material.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, etc. may be used, and in general, a spin coating method is widely used. In addition, after forming the coating film, in some cases, the residual solvent may be partially removed under reduced pressure.

As a light source for curing the resin composition according to the present specification, for example, a mercury vapor arc emitting light having a wavelength of 250 nm to 450 nm, a carbon arc, an Xe arc, etc., but is not necessarily limited thereto.

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 thin film transistor liquid crystal display (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode, Photosensitive material for forming overcoat layer, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. does not specifically put

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

The color filter may be manufactured using a resin composition including the compound represented by Formula 1 above. A color filter may be formed by coating the resin composition on a substrate to form a coating film, and exposing, developing and curing the coating film.

The resin composition according to an exemplary embodiment of the present specification has excellent heat resistance, and has little color change due to heat treatment, so that it is possible to provide a color filter having high color reproducibility and excellent sensitivity even by a curing process during the manufacture of a color filter.

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

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

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

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

The black matrix according to the exemplary embodiment of the present specification may use a black pigment or a black dye as a color material. For example, carbon black alone or a mixture of carbon black and a colored pigment can be used. At this time, since a colored pigment lacking in light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material is relatively increased. There are advantages to not being.

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 thin film transistor. It may be any one of a liquid crystal display device (Thin FIlm Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, examples will be given to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

<Preparation Example 1> - Preparation of compound 1-1

Preparation of [Compound A]

[A-1] (Benzenesulfonate Dichlorosulfofluorescein) (3g, 7.40mmol, 1eq), [A-2] (2-(Ethylamino)ethanol) (5.28g, 59.22mmol, 8eq), distilled water in a 100mL 1-neck round-bottom flask (DI-water) 50g was added and stirred at 100°C. Afterwards, the reaction was carried out overnight (12 hours). The reaction was terminated by quenching in 1M HCl solution, and sodium chloride (NaCl) was added to precipitate the reaction product. The resulting precipitate was filtered under reduced pressure and dried in an oven at 80°C. After drying, in order to remove NaCl between the products, it was dissolved in DMF (dimethylformamide) and filtered, and the filtrate was quenched in diethyl ether, filtered under reduced pressure, and dried to obtain compound A (2.88 g, 5.64). mmol, 76%) was obtained.

Ionization mode: APCI +:m/z = 511 [M+H]+, Exact Mass: 510.18

Preparation of [Compound B]

Dissolve compound A (1 g, 1.96 mmol) in 30 ml of tetrahydrofuran. 4-nitro benzoyl chloride (2.18g, 11.75mmol, 6eq) was added and stirred at 60°C. After that, the reaction was carried out for 12 hours. After completion of the reaction, the reactant was added dropwise to 300 ml of 35% saturated sodium chloride solution and filtered under reduced pressure. Thereafter, the precipitate was separated through column chromatography (Eluent MC (dichlorimethane):MeOH (Metanol)=10:1). As a result, Compound B (0.69 g, 1.054 mmol) was obtained, and the yield was 53.8%.

Ionization mode: APCI +:m/z = 660 [M+H]+, Exact Mass: 659

[Preparation of compound 1-1]

Compound B (1.319 g, 2. mmol) was dissolved in Chloroform (40 ml), and 4-dimethylaminopyridine (D-MAP) (0.487 g, 2.0 mmol) was added. 2-Hydroxyethyl Methacrylate (0.488 ml, 4.0 mmol) was added, and EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide) (1.15 g, 6.0 mmol) in CHCl ₃ (10 ml) was dropped and reacted at room temperature for 72 hours. After H ₂ O quenching (quenching), the water layer was transferred to a separatory funnel _{and extracted with CHCl 3} (Chloroform). The organic layer was separated, washed with brine, and dried _{over Na 2} SO _{4 .} Purification by flash silica column chromatography (CH ₂ Cl ₂ (dichloromethane):MeOH(Methanol)=9:1) gave compound 1-1 (1.29 g, 1.67 mmol, 56%).

Ionization mode: APCI +:m/z = 772 [M+H]+, Exact Mass: 771

<Preparation Example 2> - Preparation of compound 1-2

Preparation of [Compound D]

화합물 A-1 (Benzenesulfonate Dichlorosulfofluorescein) (3g, 7.40mmol, 1eq)과 디에탄올아민(Diethanolamine) (3.89g, 37mmol, 5eq)을 넣고 화합물 A의 제조와 같은 방법으로 제조하여 화합물 D 3.2g (수율 79.8%)을 얻었다.

Compound A-1 (Benzenesulfonate Dichlorosulfofluorescein) (3g, 7.40mmol, 1eq) and diethanolamine (3.89g, 37mmol, 5eq) were added and prepared in the same manner as in the preparation of Compound A. Compound D 3.2g (yield 79.8) %) was obtained.

Preparation of [Compound E]

4-nitro benzoyl chloride (4-nitro benzoyl chloride) (4.36g, 23.50mmol, 12eq) and compound D (1.06g, 1.96mmol, 1eq) were added and prepared as in the preparation of compound B, compound E 0.81g (yield) 40.1%) was obtained.

Ionization mode: APCI +:m/z = 841 [M+H]+, Exact Mass: 840

Preparation of [Compound 1-2]

Compound E (1.0 g, 1.19 mmol, 1eq), 2-hydroxyethyl methacrylate (2-Hydroxyethyl Methacrylate) (0.43 ml, 3.59 mmol, 3eq) was added and prepared in the same manner as in the preparation of Compound 1-1. 1-2 0.84 g (yield 65.7%) was obtained.

Ionization mode: APCI +:m/z = 1065 [M+H]+, Exact Mass: 1064

<Preparation Example 3> - Preparation of compound 2-1

Compound B (0.884g, 1.34mmol, 1eq) was dissolved in 50ml of dichloromethane, sodium hydroxide (0.05g, 1.34mmol, 1eq) and 0.02g of benzyltrimethyl ammonium were added and stirred at room temperature for 30 minutes. 1-chloro-2,3-epoxypropane (1-chloro-2,3-epoxypropane) (0.25g, 2.68mmol, 2eq) was added and stirred at 40°C for 20 hours. After stirring, the reaction product was quenched with an aqueous hydrochloric acid solution and transferred to a separatory funnel, and the aqueous layer was _{extracted with CHCl 3} (Chloroform). The organic layer was separated, washed with brine, and dried _{over Na 2} SO _{4 .} The organic layer was dried under reduced pressure and purified by flash silica column chromatography (CH ₂ Cl ₂ (dichloromethane):MeOH(Metanol)=9:1) to 0.58 g (0.81 mmol, yield: 60.7) of compound 2-1 %) was obtained.

Ionization mode: APCI +:m/z = 716 [M+H]+, Exact Mass: 715

<Preparation Example 4> - Preparation of compound 3-1

In the preparation of compound 2-1, 1-chloro-2,3-epoxypropane (0.25 g, 2.68 mmol, 2eq) was mixed with 3- (chloromethyl) 3-methyloxetane ( The experiment was carried out in the same manner except that it was changed to 3-(chloromethyl)-3-methyloxetane) (0.32g, 2.68mmol, 2eq). Compound 3-1 0.464 g (0.62 mmol, yield: 55.1%) was obtained.

Ionization mode: APCI +:m/z = 744 [M+H]+, Exact Mass: 743

<Preparation Example 5> - Preparation of compound 4-1

Compound B (0.884g, 1.34mmol, 1eq) was dissolved in 50ml of dichloromethane, sodium hydroxide (0.05g, 1.34mmol, 1eq) and 0.02g of benzyltrimethyl ammonium were added and stirred at room temperature for 30 minutes. 2-chloroacetic acid (0.25g, 2.68mmol, 2eq) was added and stirred at 40°C for 20 hours. After stirring, the reaction product was quenched with an aqueous hydrochloric acid solution and transferred to a separatory funnel, and the aqueous layer was _{extracted with CHCl 3} (Chloroform). The organic layer was separated, washed with brine, and dried _{over Na 2} SO _{4 .} The organic layer was dried under reduced pressure and purified by flash silica column chromatography (CH ₂ Cl ₂ (dichloromethane):MeOH(Metanol)=9:1) to 0.43 g (0.60 mmol, yield: 49.1) of compound 4-1 %) was obtained.

Ionization mode: APCI +:m/z = 718 [M+H]+, Exact Mass: 717

<Example>

<Preparation of resin composition Example 1>

Based on 100 parts by weight of the total weight of the resin composition, 0.85 parts by weight of the compound 1-1 prepared above, 20.78 parts by weight of binder A, 20.46 parts by weight of dipentaerythritol hexaacrylate as a polyfunctional acrylic monomer, PBG-3057 (Tronly) ) 0.68 parts by weight of leveling agent F-554 (DIC) 0.6 parts by weight, adhesive aid KBM-503 (ShinEtsu) 0.06 parts by weight, and 56.57 parts by weight of solvent diacetone alcohol (DAA, Diacetonealcohol) Resin composition Example 1 was prepared.

The binder A is a copolymer having a mass ratio of benzyl methacrylate: N-phenylmaleimide: styrene: methacrylic acid = 55:9:11:25.

<Preparation of resin composition Examples 2 to 5>

Resin composition Examples 2 to 5 were prepared in the same manner as in Resin Composition Example 1, except that Compound 1-1 of Resin Composition Example 1 was changed to the compound shown in Table 1 below.

Example 1 Example 2 Example 3 Example 4 Example 5 compound 1-1 1-2 2-1 3-1 4-1

<Preparation of resin composition Comparative Examples 1 and 2>

Resin composition Comparative Examples 1 and 2 were prepared in the same manner as in Resin Composition Example 1 except that the compound of Resin Composition Example 1 was changed to the following rhodamine B or compound K1.

<Comparative Example 1>

As the compound of Comparative Example 1, rhodamine B was used.

<Comparative Example 2>

[Compound K1]

As the compound of Comparative Example 2, compound K1 having the above structure was used.

<Experimental example>

[Substrate production]

The resin compositions prepared in Comparative Examples 1 and 2 and Examples 1 to 5 were spin-coated on glass (5 cm X 5 cm) and pre-bake was performed at 100° C. for 100 seconds to form a film. After the pre-heat treatment, the substrate was manufactured by post-bake treatment at 230° C. for 20 minutes.

[Heat resistance evaluation]

An absorption spectrum in a wavelength range of 380 to 780 nm was obtained by using a spectrometer (MCPD, Otsuka Co.) for the post-bake substrate prepared under the above conditions.

In addition, the transmittance spectrum was obtained in the same measurement range as the same equipment by additionally treating the post heat treatment substrate (post bake once) at 230° C. for 60 minutes.

Using the values L*, a*, and b* obtained from the absorption spectrum obtained using the C light source as a backlight, ΔEab was calculated by Equation 1 below and shown in Table 2 below.

[Formula 1]

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

A small ΔEab value means less color change, indicating excellent heat resistance.

[Evaluation of chemical resistance]

A substrate was prepared by the above method, cut to 1 cm Х 5 cm, and then two pieces of the substrate cut to 1 cm Х 5 cm were immersed in 16 g of N-methyl-2-pyrrolidone solvent, and then at 80 ° C. Additional heat treatment (Baking) was performed for 40 minutes in a convection oven of The absorbance of the solvent from which the substrate piece was taken out was measured, and the absorbance and improvement rates (%) of Examples 1 to 5 compared to Comparative Example 1 are described in Table 2 below.

As absorbance measurement equipment, Mega-2100 (Double Beam UV-Vis Spectrophotometer) manufactured by Scinco was used.

[CR Characteristics Evaluation]

After the substrate is manufactured by the above method and post-baking, the fluorescence intensity is measured using a fluorescence meter.

As a fluorescence intensity measurement device, FS-2 (Fluorescence Spectrometer) manufactured by Scinco was used.

In Table 2 below, the absorbance and improvement rates (%) of Comparative Examples 2 and 1 to 5 compared to Comparative Example 1 are described.

△Eab absorbance Chemical resistance improvement rate (%) Fluorescence intensity improvement rate (%) Comparative Example 1 62.4 1.523 100% 100% Comparative Example 2 6.66 0.702 46.1% 108.3% Example 1 3.08 0.562 63.1% 28.6% Example 2 5.49 0.377 75.2% 58.3% Example 3 7.01 0.785 48.5% 62.3% Example 4 4.58 0.269 82.3% 50.5% Example 5 5.23 0.355 76.7% 34.7%

According to Table 2, it was confirmed that the ΔEab values of Examples 1 to 5 were much smaller than the ΔEab values of Comparative Example 1. Thereby, it confirmed that it was possible to obtain the coloring composition for color filters excellent in heat resistance, and a color filter by using the xanthene type pigment|dye which introduce|transduced the specific substituent and crosslinkable group of this invention.

It was confirmed that the absorbance of Examples 1 to 5 was smaller than the absorbance of Comparative Example 1. The lower the absorbance, the better the chemical resistance. Thereby, the coloring composition for color filters in which the chemical resistance by a solvent was improved was obtained by using the xanthene type pigment|dye which introduce|transduced the specific substituent and crosslinkable group of this invention.

It was confirmed that the fluorescence intensity of Examples 1 to 5 was smaller than the fluorescence intensity of Comparative Examples 1 and 2. The lower the fluorescence intensity, the better the contrast ratio. In particular, compound K of Comparative Example 2 is a xanthene dye including a curable group, has a curable group, has a high bonding strength with the binder resin, and is not significantly different from Examples 1 to 5 in heat resistance and chemical resistance, but an electron withdrawing group or an electron donating group There is no energy level tuning effect because it does not contain fluorescence intensity. Accordingly, energy level tuning was possible through the introduction of a specific substituent of the present invention, and the fluorescence intensity could be reduced. As a result, a coloring composition for a color filter having an improved contrast ratio was obtained.

Claims (16)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
L1 to L4 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, Formula 1-A; Or represented by the following formula 1-B,
R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r1 and r2 are each an integer of 1 to 3,
r3 is an integer from 1 to 4,
When r1 to r3 are 2 or more, two or more R1 to R3 are the same as or different from each other,
X1 is represented by the following formula 1-A,
X2 is represented by the following formula 1-B,
[Formula 1-A]

[Formula 1-B]

In Formula 1-A and Formula 1-B,
Q1 and Q2 are the same as or different from each other, and each independently O; or NH;
L101 and L102 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
A1 is hydrogen; heavy hydrogen; nitro group; nitrile group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkoxy group,
a1 is an integer from 1 to 5,
When a1 is 2 or more, two or more A1s are the same as or different from each other,
B1 is any one selected from the following structures,

In the structure,
L201 is a direct bond; or O;
R201 to R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r202 is an integer from 1 to 3,
r203 is an integer from 1 to 5,
When r202 and r203 are each 2 or more, two or more R202 and R203 are the same or different from each other,
* denotes a part to be connected. The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 2-1 to 2-7:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-1 to 2-7,
L1 to L4, R1 to R3, r1 to r3, Q1, Q2, L101 and L102 are as defined in Formula 1 above,
Ar11 and Ar12 are the same as or different from each other, and each independently represents a hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
Q3 to Q6 are the same as or different from each other, and each independently O; or NH;
A11 to A13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitro group; nitrile group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkoxy group,
a11 to a13 are the same as or different from each other, and each independently an integer of 1 to 5,
When a11 to a13 are two or more, two or more A11 to A13 are the same as or different from each other,
L103 to L106 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
B11 to B13 are the same as or different from each other, and each independently any one selected from the following structures,

In the structure,
L201 is a direct bond; or O;
R201 to R203 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r202 is an integer from 1 to 3,
r203 is an integer from 1 to 5,
When r202 and r203 are each 2 or more, two or more R202 and R203 are the same or different from each other,
* denotes a part to be connected. The method according to claim 1,
B1 is a compound represented by any one of the following structures:

* means the part to be connected. The method according to claim 1,
Ar1 and Ar2 are the same as or different from each other, and each independently a hydroxyl group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isopropyl group; Or a substituted or unsubstituted phenyl group, Formula 1-A; Or a compound represented by the formula 1-B. The method according to claim 1,
L1 to L4 are the same as but different from each other, and each independently a direct bond; a substituted or unsubstituted C 1 to C 10 alkylene group; Or a substituted or unsubstituted C6-C12 substituted or unsubstituted arylene group. The method according to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following compounds:

. A polymer comprising the compound according to any one of claims 1 to 6 as a monomer. A color material composition comprising the compound according to any one of claims 1 to 6. The color material composition of claim 8, further comprising at least one of a dye and a pigment. The colorant composition according to claim 9, wherein the dye is at least one dye selected from a xanthene dye, a cyanine dye, an anthraquinone dye, an azaporphyrin dye, and an azo metal complex, and the pigment is a red pigment. The compound of any one of claims 1 to 6; binder resin; polyfunctional monomers; And a resin composition comprising a photoinitiator. The resin composition of claim 11, further comprising an additive. The resin composition of claim 11, further comprising a solvent. A photosensitive material comprising the resin composition according to claim 11 or a cured product thereof. A color filter comprising the photosensitive material according to claim 14 . A display device comprising the color filter according to claim 15 .