KR20140121209A - Positive type photosensitive resin composition for color filter and color filter using the same - Google Patents

Positive type photosensitive resin composition for color filter and color filter using the same Download PDF

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KR20140121209A
KR20140121209A KR20130037694A KR20130037694A KR20140121209A KR 20140121209 A KR20140121209 A KR 20140121209A KR 20130037694 A KR20130037694 A KR 20130037694A KR 20130037694 A KR20130037694 A KR 20130037694A KR 20140121209 A KR20140121209 A KR 20140121209A
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unsubstituted
substituted
group
formula
photosensitive resin
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KR20130037694A
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정지영
김동완
김지홍
류지현
이인재
한규석
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제일모직주식회사
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    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509Filters, e.g. light shielding masks
    • G02F1/133514Colour filters
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007Filters, e.g. additive colour filters; Components for display devices
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/022Quinonediazides
    • G03F7/023Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/039Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055Radiation sensitive composition or product or process of making

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  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)

Abstract

(A) an alkali-soluble resin comprising a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (2), or a combination thereof; (B) a dye comprising a cyanine dye represented by the following formula (C) a photosensitive diazoquinone compound, and (D) a solvent, and a photosensitive resin film and a color filter using the positive photosensitive resin composition.
[Chemical Formula 1]

Figure pat00053

(2)
Figure pat00054

(3)
Figure pat00055

(In the above Formulas 1 to 3, X 1 to X 4 , Y 1 to Y 4 , Z 1 , Z 2 , A and R 1 to R 15 are as defined in the specification.)

Description

TECHNICAL FIELD [0001] The present invention relates to a positive-type photosensitive resin composition and a color filter using the positive-

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

The liquid crystal display device, which is one of the display devices, has advantages such as lightness, thinness, low cost, low power consumption driving and bonding with a good integrated circuit, and the use range thereof is expanded for notebook computers, monitors and TV images. Such a liquid crystal display device includes a color filter in which unit pixels in which red (R), green (G), and blue (B) subpixels corresponding to the three primary colors of light are repeatedly formed. When the subpixels are arranged adjacent to each other and a color signal is applied to each subpixel to control the brightness, a specific color is displayed in the unit pixel by combining the three primary colors.

The color filters are made of red (R), green (G), and blue (B) dyes or pigments, and these dye materials convert white light of the backlight unit into respective corresponding colors. The spectrum of the dye material is improved as long as the spectrum has a narrow absorption band having no unnecessary wavelength in addition to the required absorption wavelength. In addition, it should have high heat resistance, light resistance, and chemical resistance that do not fade or discolor under ultraviolet, acid, and base conditions exposed in the etching process of color resist.

Such a color filter is known to be formed by photolithography using a photosensitive resin composition.

As such a method of producing by photolithography, a negative type having a property of curing by irradiation of light is generally used. It has also been proposed to use a positive type instead of the conventional negative type in order to form a fine profile of a fine pattern in a photosensitive resin composition containing a colorant used for forming a color filter by a photolithography method .

However, the color filter using the conventional positive photosensitive resin composition contains a novolac resin, an acrylic resin, hydroxystyrene, and the like, so that heat resistance is insufficient when a color filter, a lens, an interlayer insulating film or the like is formed. Such a heat resistance problem is remarkably deteriorated in the pattern retention performance and can cause reliability problems.

 Further, in order to improve the color development of the formed color filter, the film formed by the photosensitive resin composition containing no coloring agent is preferable to have high transparency, but transparency in the conventional positive photosensitive resin composition is also insufficient.

In recent years, as a part of environmental issues and reliability, fume problems have also emerged in the process.

Therefore, it is urgently required to develop a positive photosensitive resin composition having excellent heat resistance and high sensitivity and a color filter using the same.

An embodiment of the present invention is to provide a positive photosensitive resin composition excellent in heat resistance, pattern formability, residue removability, transparency and chemical resistance.

Another embodiment of the present invention is to provide a photosensitive resin film using the above positive photosensitive resin composition.

Another embodiment of the present invention is to provide a color filter comprising the photosensitive resin film.

(A) an alkali-soluble resin comprising a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (2), or a combination thereof, (B) a cyanine- (D) a dye, (C) a photosensitive diazoquinone compound, and (D) a solvent.

[Chemical Formula 1]

Figure pat00001

(2)

Figure pat00002

(3)

Figure pat00003

Wherein X 1 and X 2 are each independently a substituted or unsubstituted C6 to C30 aromatic organic group and Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C30 aromatic organic group , a substituted or unsubstituted divalent to hexavalent C1 to C30 aliphatic organic group, or a substituted or unsubstituted 2 to 6 valent C3 to C30 cycloaliphatic, and may organic date, R 14 and R 15 are each independently a hydrogen atom, A halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 haloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 alkenyl group, Substituted or unsubstituted C3 to C20 cycloalkenyl group, substituted or unsubstituted C3 to C20 cycloalkynyl group, substituted or unsubstituted C3 to C20 cycloalkynyl group, substituted or unsubstituted C3 to C20 cycloalkenyl group, substituted or unsubstituted C3 to C20 cycloalkynyl group, A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted A C2 to C30 heteroaryl group, or a substituted or unsubstituted C1 to C20 alkyl (meth) acrylate group.

X 3 and X 4 may each independently be a carbon atom, an oxygen atom or a sulfur atom, Y 3 and Y 4 each independently represents a single bond, -O-, - (CH 2 ) mCOO- (0≤m≤5), it may be -OCO-, -NH- or -CONH-, Z 1 and Z 2 may be a ring substituent with one double bond, respectively, R 3 to R 13 is Each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 haloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 alkene Substituted or unsubstituted C1 to C20 alkynyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C3 to C20 cycloalkenyl group, substituted or unsubstituted C3 to C20 cycloalkynyl group, substituted or unsubstituted C3 to C20 cycloalkenyl group, Unsubstituted C2 to C20 heterocycloalkyl groups, substituted Is a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or A substituted or unsubstituted C1 to C20 alkyl (meth) acrylate group,

A may be a halogen ion, a compound represented by ClO 4 - , BF 4 - , SbF 6 - , CF 3 SO 3 - , N (SO 2 CF 3 ) 2 - , the following formula have.

[Formula 3-1]

Figure pat00004

[Formula 3-2]

Figure pat00005

The alkali-soluble resin may be a polybenzoxazole precursor, a polyamic acid ester, a polyimide, or a combination thereof.

In Formula 3, Z 1 and Z 2 may each be a substituent represented by the following Formula 4-1 or a substituent represented by the following Formula 4-2.

[Formula 4-1]

Figure pat00006

[Formula 4-2]

Figure pat00007

In the general formulas (4-1) and (4-2), R and R 'are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or A substituted or unsubstituted C2 to C30 heteroaryl group.

In Formula 3, R 6 to R 11 each independently represent a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkyl (meth) acrylate group.

In Formula 3, A may be a halogen ion, CF 3 SO 3 - or N (SO 2 CF 3 ) 2- .

The cyanine-based dye may have a wavelength of 400 to 700 nm of light emitted again.

When the alkali-soluble resin is a combination of the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2), the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) To 95: 5 mol%, respectively.

When the alkali-soluble resin is a combination of the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2), the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) To 40: 60 mol% to 95: 5 mol%, respectively.

The dye may further include a methine dye represented by the following formula (5).

[Chemical Formula 5]

Figure pat00008

Wherein R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an ether group, an amine group or an amine derivative group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 A substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C2 to C20 alkynyl group, Or an unsubstituted or substituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group .

The dye may further include an organic salt type dye represented by the following formula (6).

[Chemical Formula 6]

Figure pat00009

In Formula 6, R 1 to R 3 each independently may be a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, or a substituted or unsubstituted C 3 to C 20 cycloalkyl group, and all of R 1 to R 3 are hydrogen Can be excluded,

R 1 to R 3 are independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, and combinations thereof, but not all hydrogen atoms,

R 4 may be selected from the group consisting of a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 heterocycloalkyl group, a substituted or unsubstituted C 3 to C 20 heteroaryl group, and combinations thereof, a group selected from the group consisting of an imine group, an azo group, a pyrazolone group, a fuchsine group, an anthraquinone group, and combinations thereof.

The positive photosensitive resin composition may further include at least one of a silane compound, a dissolution regulator, and an acid generator.

Wherein the positive photosensitive resin composition comprises 1 to 80 parts by weight of the dye (B), 5 to 100 parts by weight of the photosensitive diazoquinone compound (C), and 100 to 100 parts by weight of the dye (D), based on 100 parts by weight of the alkali- ) Solvent of 50 to 500 parts by weight.

Another embodiment of the present invention provides a photosensitive resin film produced using the positive photosensitive resin composition.

Another embodiment of the present invention provides a color filter comprising the photosensitive resin film.

To provide a positive photosensitive resin composition excellent in heat resistance, pattern formability, residue removability, transparency and chemical resistance, a photosensitive resin film using the same, and a color filter.

1 is a graph showing absorbance characteristics of R008.
2 is a graph showing the absorbance characteristics of YR.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, unless otherwise defined, at least one hydrogen atom of the functional group of the present invention is a halogen atom (F, Cl, Br, or I), a hydroxy group, a nitro group, a cyano group , an imino group (= NH, = NR, R is C1 to C10 alkyl group), an amino group (-NH 2, -NH (R ' ), -N (R ") (R"'), R ' to R "' A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heteroaryl group, and a substituted or unsubstituted C2 to C30 heterocycloalkyl group.

In the present specification, "hetero" means that a carbon atom is substituted with any one atom selected from the group consisting of N, O, S and P, unless otherwise defined.

In the present specification, "(meth) acrylate" should be understood to mean "acrylate" or "methacrylate".

As used herein, unless otherwise defined, "combination" means mixing or copolymerization. "Copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.

In the present specification, "*" means the same or different atom or part connected to a chemical formula.

(A) an alkali-soluble resin comprising a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (2), or a combination thereof, (B) a positive- A dye containing a cyanine dye to be displayed, (C) a photosensitive diazoquinone compound, and (D) a solvent.

When a mixture of the alkali-soluble resin (A) and the dye (B) is used, a photosensitive resin film excellent in sensitivity, low in residual film ratio, high in brightness, excellent in chemical resistance and heat resistance can be obtained.

Each component of the positive photosensitive resin composition will be specifically described below.

(A) an alkali-soluble resin

The alkali-soluble resin (A) is not limited as long as it is an alkali-soluble resin generally used in the technical field of the present invention. Specifically, the alkali-soluble resin is a polyamic acid ester precursor comprising a polybenzoxazole precursor containing a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula , A polyamic acid containing a repeating unit represented by the following formula (7), and a polyimide including a repeating unit represented by the following formula (8).

Polybenzoxazole  Precursor and Polyamic acid  Ester precursor

[Chemical Formula 1]

Figure pat00010

(2)

Figure pat00011

Wherein X 1 and X 2 are substituted or unsubstituted C6 to C30 aromatic organic groups, Y 1 and Y 2 substituted or unsubstituted C6 to C30 aromatic organic groups, substituted or unsubstituted di and to 6-valent C1-C30 aliphatic organic group, or a substituted or unsubstituted divalent to hexavalent C3 to C30 alicyclic organic ring, R 14 and R 15 are each independently a hydrogen atom, ring a halogen atom, a substituted or unsubstituted A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 haloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 alkenyl group, a substituted or unsubstituted C1 to C20 alkynyl group, Or a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, A substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted Or an unsubstituted C1 to C20 alkyl (meth) acrylate group.

In the above formula (1), X 1 is an aromatic organic group and may be a residue derived from an aromatic diamine.

Examples of the aromatic diamine include 3,3'-diamino-4,4'-dihydroxybiphenyl, 4,4'-diamino-3,3'-dihydroxybiphenyl, bis (4-amino-3-hydroxyphenyl) sulfone, bis (4-amino-3-hydroxyphenyl) sulfone, bis 2,2-bis (4-amino-3-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane, 2,2- Hexafluoropropane, 2,2-bis (3-amino-4-hydroxy-5-trifluoromethylphenyl) hexafluoropropane, 2,2- (3-amino-4-hydroxy-2-trifluoromethylphenyl) hexafluoropropane, 2,2-bis , 2-bis (4-amino-3-hydroxy-5-trifluoromethylphenyl) hexafluoropropane, 2,2- rope (4-amino-3-hydroxy-2-trifluoromethylphenyl) hexafluoropropane, 2,2-bis Phenyl) hexafluoropropane, 2- (3-amino-4-hydroxy-5-trifluoromethylphenyl) -2- 2- (3-hydroxy-4-amino-5-trifluoromethylphenyl) hexafluoropropane, 2- (3-amino-4-hydroxy-5-trifluoromethylphenyl) -2- 2- (3-amino-4-amino-6-trifluoromethylphenyl) hexafluoropropane, 2- 2-trifluoromethylphenyl) hexafluoropropane, 2- (3-amino-4-hydroxy-2-trifluoromethylphenyl) Methylphenyl) -2- (3-hydroxy-4-amino-5-trifluoromethylphenyl) hexafluoropropane and 2- Hydroxy-6-trifluoromethylphenyl) -2- (3-hydroxy-4-amino-5-trifluoromethylphenyl) hexafluoropropane may be used, It is not.

In the above formulas (1) and (2), Y 1 And Y 1 is an aromatic organic group, a divalent to hexavalent aliphatic organic group, or a divalent to hexavalent alicyclic group, and may be a residue of a dicarboxylic acid or a residue of a dicarboxylic acid derivative. Specifically, Y 1 may be an aromatic organic group, or a divalent to hexavalent alicyclic organic group.

Examples of the dicarboxylic acid include Y (COOH) 2 (wherein Y is the same as Y 1 and Y 2 in the above formulas (1) and (2)).

Examples of the di-carboxylic acid derivatives Y (COOH) carbonyl halide derivative, or Y (COOH) 2 and 1-hydroxy-1,2,3-benzotriazole-active ester derivative by reacting a sol such as the active compounds of the 2 (Wherein Y represents Y < 1 > And Y < 2 >).

Specific examples of the dicarboxylic acid derivative include 4,4'-oxydibenzoyl chloride, diphenyloxydicarbonyldichloride, bis (phenylcarbonyl chloride) sulfone, bis (phenylcarbonyl chloride) ether, bis (phenylcarbonyl chloride ) Phenone, phthaloyldichloride, terephthaloyldichloride, isophthaloyldichloride, dicarbonyldichloride, diphenyloxydicarboxylate dibenzotriazole, or combinations thereof, but is not limited thereto.

The polybenzoxazole precursor and the polyamic acid ester precursor may have a thermally polymerizable functional group derived from a reactive terminal blocking monomer on one or both of the branched chain terminals. The reactive end blocking monomer is preferably a monoamine having a carbon-carbon double bond or a monoanhydride, or a combination thereof. Examples of the monoamines include, but are not limited to, toluidine, dimethyl aniline, ethyl aniline, aminophenol, aminobenzyl alcohol, aminoindan, aminoacetone phenone, and combinations thereof.

Polyamic acid  And polyimide

(7)

Figure pat00012

[Chemical Formula 8]

Figure pat00013

In the general formulas (7) and (8), X 2 and X 3 are each independently a substituted or unsubstituted C6 to C30 aromatic organic group, a substituted or unsubstituted divalent to hexavalent C1 to C30 aliphatic group, a substituted or unsubstituted A divalent to hexavalent C3 to C30 alicyclic organic group, or an organosilane group.

Specifically, in the formulas (7) and (8), X 2 and X 3 may each independently be a residue derived from an aromatic diamine, an alicyclic diamine or a silicone diamine. At this time, the aromatic diamine, alicyclic diamine and silicon diamine may be used singly or in combination of one or more thereof.

Examples of the aromatic diamine include 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfide, benzidine, m-phenylenediamine, p-phenylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine , Bis [4- (4-aminophenoxy) phenyl] sulfone, bis (4-aminophenoxy) ] Ether, 1,4-bis (4-aminophenoxy) benzene, a compound in which the aromatic ring thereof is substituted with an alkyl group or a halogen atom, or a combination thereof, but is not limited thereto.

Examples of the alicyclic diamine include, but are not limited to, 1,2-cyclohexyldiamine, 1,3-cyclohexyldiamine, or a combination thereof.

Examples of the silicon diamine include bis (4-aminophenyl) dimethylsilane, bis (4-aminophenyl) tetramethylsiloxane, bis (p- aminophenyl) tetramethyldisiloxane, Bis (? -Aminopropyldimethylsilyl) benzene, bis (4-aminobutyl) tetramethyldisiloxane, bis (? -Aminopropyl) tetraphenyldisiloxane, 1,3- Methyldisiloxane, or combinations thereof, but are not limited thereto.

Y 2 and Y 3 are each independently a substituted or unsubstituted C6 to C30 aromatic organic group, a substituted or unsubstituted quadrivalent to hexavalent C1 to C30 aliphatic group, Is a C4 to C20 alicyclic organic group.

Y 2 and Y 3 may each independently be an aromatic acid dianhydride or a residue derived from an alicyclic acid anhydride. At this time, the aromatic acid dianhydride and the alicyclic acid dianhydride may be used alone or in admixture of at least one thereof.

Examples of the aromatic acid dianhydride include pyromellitic dianhydride; Benzophenone tetracarboxylic dianhydride such as benzophenone-3,3 ', 4,4'-tetracarboxylic dianhydride, benzophenone-3,3'4,4'-tetracarboxylic dianhydride, ; Oxydiphthalic dianhydride such as 4,4'-oxydiphthalic dianhydride; Biphthalic dianhydride such as 3,3 ', 4,4'-biphthalic dianhydride (3,3', 4,4'-biphthalic dianhydride); (Hexafluoroisopropylidene) diphthalic dianhydride such as 4,4 '- (hexafluoroisopropylidene) diphthalic dianhydride (4,4' - (hexafluoroisopropylidene) diphthalic dianhydride) ; Naphthalene-1,4,5,8-tetracarboxylic dianhydride; 3,4,9,10-perylenetetracarboxylic dianhydride, and the like, but the present invention is not limited thereto.

Examples of the alicyclic dianhydrides include 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-cyclohexane-1,2-dicarboxylic acid dianhydride (5- (2,5-dioxotetrahydrofuryl) -3-methyl-cyclohexane-1,2-dicarboxylic anhydride), 4- (2,5- dioxotetrahydrofuran-3-yl) -tetralin- (2,5-dioxotetrahydrofuran-3-yl) -tetralin-1,2-dicarboxylic anhydride, bicyclooctene-2,3,5,6-tetracarboxylic dianhydride, 2,3,5,6-tetracarboxylic dianhydride, bicyclooctene-1,2,4,5-tetracarboxylic dianhydride, and the like. But is not limited thereto.

The weight average molecular weight (Mw) of the alkali-soluble resin is preferably 3,000 to 300,000, and more preferably 5,000 to 30,000 g / mol. When the weight average molecular weight (Mw) is within the above range, a sufficient residual film ratio can be obtained in an unexposed area at the time of development with an aqueous alkali solution, and patterning can be efficiently performed.

When the alkali-soluble resin is a combination of the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2), the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) To about 95: 5 mole%, and more specifically from about 60: 40 mole% to about 95: 5 mole%, respectively, based on the total weight of the composition. When the molar ratio of the respective repeating units constituting the alkali-soluble resin is within the above range, the solubility in an aqueous alkali solution, the residual film ratio, and physical properties such as patterning can be further improved.

In particular, when the alkali-soluble resin is used in combination with a dye containing a cyanine dye represented by the following formula (3), a photosensitive resin having excellent sensitivity and low residual film ratio, high luminance, and excellent chemical resistance and heat resistance A film can be obtained.

(B) Dye

(B-1) Cyanine series  dyes

The cyanine dye may be a compound represented by the following formula (3).

In the above formula (3)

(3)

Figure pat00014

In Formula 3, X 3 and X 4 may each independently be a carbon atom, an oxygen atom or a sulfur atom.

Y 3 and Y 4 are each independently a single bond, -O-, - (CH 2 ) m COO- (0? M ? 5), -OCO-, -NH- or -CONH- have.

In Formula 3, Z 1 and Z 2 may each be a ring substituent having one double bond. Specifically, Z 1 and Z 2 may each be a substituent represented by the following formula (4-1) or a substituent represented by the following formula (4-2).

[Formula 4-1]

Figure pat00015

[Formula 4-2]

Figure pat00016

In the general formulas (4-1) and (4-2), R and R 'are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or A substituted or unsubstituted C2 to C30 heteroaryl group.

The cyclic substituent group having one double bond such as the substituents represented by the above formulas (4-1) and (4-2) is a functional group capable of thermal polymerization, and when the double bond is used together with the above-mentioned (A) The thermal crosslinking of the polymerizable functional groups may crosslink the molecular chains and increase the molecular weight of the polymer, resulting in a film that is hardened and heat resistance can be increased. In addition, since the polymers hardened by crosslinking can stably contain dyes and pigments, excellent effects on chemical resistance can be obtained. As a result, when a cyanine dye having the ring substituent at the terminal thereof is used in a photosensitive resin composition for a color filter, a color filter excellent in heat resistance and chemical resistance can be obtained.

In Formula 3, R 3 to R 15 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 haloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group , A substituted or unsubstituted C1 to C20 alkenyl group, a substituted or unsubstituted C1 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted heterocyclic alkynyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C1 to C20 alkyl (meth) acrylate One can.

Specifically, R 6 to R 11 each independently represent a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkyl (meth) acrylate group.

In Formula 3, A represents a halogen ion, ClO 4 - , BF 4 - , SbF 6 - , CF 3 SO 3 - , N (SO 2 CF 3 ) 2 - Or an ionic compound. Of these, the halogen ion may be preferably CF 3 SO 3 - , N (SO 2 CF 3 ) 2 - .

[Formula 3-1]

Figure pat00017

[Formula 3-2]

Figure pat00018

In Formula 3, Z 1 and Z 2 may be the substituent represented by the following Formula 4-1 or 4-2.

[Formula 4-1]

Figure pat00019

[Formula 4-2]

Figure pat00020

In formulas (4-1) and (4-2), R and R 'are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C2 to C20 alkene Substituted or unsubstituted C2 to C20 alkynyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C3 to C20 cycloalkenyl group, substituted or unsubstituted C3 to C20 cycloalkynyl group, substituted or unsubstituted C2 to C20 alkynyl group, A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 aryl group, Lt; / RTI > may be an unsubstituted C2 to C30 heteroaryl group.

In formula (3), R 4 to R 9 each independently represent a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C1 to C20 alkyl (meth) acrylate group, A represents a halogen ion, CF 3 SO 3 - or N (SO 2 CF 3 ) 2 - .

The cyanine dyes have a high transmittance and thus can realize a color filter having a high brightness. By introducing a structure having a crosslinking property at the terminal thereof, the cyanine dye increases the degree of curing by heat crosslinking, and exhibits excellent heat resistance and chemical resistance.

The cyanine dye represented by Formula 3 may be mixed with other red cyanine dye. The red cyanine dye may be another material having a different structure from the cyanine dye represented by Formula 3, and may be a material having a red wavelength.

The cyanine dyes may be used in combination with the dyes described below, that is, the methine dyes represented by the formula (5) or the organic salt type dyes represented by the formula (6).

(B-2) Methine system  dyes

The dye may further include a methine dye represented by the following formula (5). The methine-based dye may be a yellow-based dye.

[Chemical Formula 5]

Figure pat00021

In Formula 5,

R 1 and R 2 are the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, an ether group, an amine group or an amine derivative group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group , A substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group.

Specifically, in Formula 5, R 1 and R 2 each independently represent a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cyclo A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 aryl Or a substituted or unsubstituted C6 to C30 aryloxy group.

More specifically, R 1 is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, R 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted aniline group, A substituted or unsubstituted benzyl group, an unsubstituted aniline derivative group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted morpholinyl group, a substituted or unsubstituted naphthyl group, A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinoloxy group, a substituted or unsubstituted quinolinyl group, A quinoxalinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyrazolyl group, An imidazolyl group, A dihydrobenzofuranyl group, a substituted or unsubstituted triazolyl group, or a substituted or unsubstituted oxazolyl group. Of these, a substituted or unsubstituted aniline group, a substituted or unsubstituted thiazolyl group, Or a substituted or unsubstituted aniline derivative group.

More specifically, the methine dye may be represented by the following formula (5-1).

[Formula 5-1]

Figure pat00022

In Formula 5-1, R 7 may be a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

In Formula 5-1 R 8 and R 9 are, each independently, a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl ring, or an ether may be date, n 5 is 0 Lt; / RTI >

When the cyanine-based dye and the methine-based dye are mixed and used, a high luminance effect can be obtained while matching the target x and y coordinates.

The cyanine dye and the methine dye represented by Chemical Formula 5 may be mixed in a weight ratio of 50:50 to 90:10 and may be used in a weight ratio of 70:30 to 80:20. When they are mixed within the above weight ratio range, they can have an appropriate spectrum, and the brightness can be further improved because of high transmittance.

The photosensitive resin composition for a color filter may further comprise a yellow dye other than the methine dye represented by the formula (5).

(B-3) Organic salt  Form dye

The dye may further include an organic salt type dye represented by the following formula (6). The organic salt type dye may be a dye having a sulfonic acid group, and other dyes may be mixed as needed.

[Chemical Formula 6]

Figure pat00023

In Formula 6, R 1 to R 3 may independently be selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, and combinations thereof, It is not a hydrogen atom.

In Formula 6, R 4 is selected from the group consisting of substituted or unsubstituted C1 to C20 heteroalkyl groups, substituted or unsubstituted C3 to C20 heterocycloalkyl groups, substituted or unsubstituted C3 to C20 heteroaryl groups, and combinations thereof. And may be a group selected from the group consisting of an imine group, an azo group, a pyrazolone group, a fuchsine group, an anthraquinone group, and combinations thereof.

The amine included in the dye represented by Formula 6 is an alkylamine and is selected from the group consisting of trioctylamine (TOA), tridodecylamine (TDA), dioctylamine (DOA) But is not limited thereto.

The sulfonic acid contained in the dye represented by Formula 6 may be 2,5-dichloro-4- 4,5-dihydro-3-methyl-5-oxo-4- (4-sulfophenyl) azo- yl-benzenesulfonic acid, 4-chloro-3- [4,5-dihydro-3-methyl-5-oxo-4 - [[3 - [(phenylamino) sulfonyl] phenyl] azo] -1H-pyrazol- ] - benzenesulfonic acid, 3 - [[4- (phenylamino) phenyl] azo] -benzenesulfonic acid, [1,1'-Biphenyl] -2,2'- disulfonicacid, dihydro-3-methyl-5-oxo-1-phenyl-1H-pyrazol-4- yl) azo] -benzenesulfonic acid, hydroxy [ phenylamino) carbonyl] propyl] azo] benzenesulfonato (3-yl) -chromate (1-), 4 - [[4- (4-hydroxy-2- methylphenyl) azolphenyl] amino] -3-nitrobenzenesulfonic acid 2 methyl-3-methyl-benzenesulfonic acid and N- [4- [4-amino-3-sulfophenyl] A mixture of [4- (dimethylamino) phenyl] [4- [ethyl [(3-sulfophenyl) methyl] amino] phenyl] methylene] -2,5-cyclohexadien-1-ylidene] -N-ethyl-3-sulfo-benzenemethanaminium It may be chosen from the military, But is not limited thereto.

When the cyanine dye and the organic salt dye are mixed and used, the effect of increasing the contrast ratio can be obtained.

The cyanine dye and the organic salt dye of Formula 6 may be mixed in a weight ratio of 60:40 to 95: 5, and may be used in a weight ratio of 80:20 to 90:10. . In general, the contrast ratio is low for high brightness, but when mixed within the above weight ratio range, the contrast ratio can be improved while maintaining high brightness.

The dye is excellent in solubility in a solvent used in a photosensitive resin composition for a color filter according to one embodiment, that is, in a solvent (D) to be described later, and unlike a pigment having a particle property, The primary particle diameter is as small as 1 to 10 nm, and it can have high durability. When the particle size of the dye is very small as compared with the pigment, the light scattering is reduced and consequently the contrast ratio can be improved. Accordingly, it is possible to compensate the decrease of the contrast ratio and the luminance, which are the problems of the pigment dispersion method used mainly for the production of color filters.

The dye may have a solubility in a solvent of 3 to 20, and may be 3 to 12 in particular. When the solubility is within the above range, precipitation of the dye is prevented, and compatibility with other components constituting the photosensitive resin composition for a color filter and coloring power are excellent.

The dye may have a maximum absorption wavelength in a wavelength range of 400 to 460 nm in spectral analysis and a transmittance in a wavelength range of 500 to 800 nm in spectral analysis may be 95 to 100%. High brightness can be exhibited when having the above range of characteristics.

The dye has high heat resistance. That is, the thermal decomposition temperature when measured by a thermogravimetric analyzer (TGA) may be 200 ° C or higher, specifically 200 ° C to 400 ° C.

The dyes having the above characteristics can be usefully used for color filters such as LCDs and LEDs that exhibit high brightness and high contrast ratio in a desired color coordinate.

The dye may be contained in an amount of 0.1 to 20% by weight based on the total amount of the photosensitive resin composition for a color filter, and may be contained in an amount of 5 to 15% by weight. When the dye is used in the above range, High luminance can be expressed in the color coordinates.

(C) Photosensitive Diazoquinone  compound

The photosensitive diazoquinone compound may be a compound having a 1,2-benzoquinone diazide structure or a 1,2-naphthoquinone diazide structure.

The photosensitive diazoquinone compound may be at least one compound selected from compounds represented by the following general formulas (9) and (11) to (13), but is not limited thereto.

[Chemical Formula 9]

Figure pat00024

In the above formula (9), R 60 to R 62 each independently represents a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, and may specifically be a methyl group.

In formula (9), R 63 to R 65 may each independently be OQ, and Q may be a hydrogen atom, a functional group represented by the following formula (10a) or a functional group represented by the following formula (10b) There is no.

In Formula 9, n 20 to n 22 may each be an integer of 0 to 5.

[Chemical Formula 10a]

Figure pat00025

[Chemical Formula 10b]

Figure pat00026

(11)

Figure pat00027

In Formula 11, R 66 may be a hydrogen atom or a substituted or unsubstituted C1 to C30 alkyl group, and R 67 to R 69 may each independently be OQ, and Q is the same as defined in Formula 9 , n 23 To n 25 each may be an integer of 0 to 5.

[Chemical Formula 12]

Figure pat00028

In Formula 12, A 3 may be CO or CR 74 R 75 , and R 74 And R 75 may each independently be a substituted or unsubstituted C1 to C30 alkyl group.

In formula (12), R 70 to R 73 may each independently be a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, OQ or NHQ, and Q is the same as defined in formula (9).

In Formula 12, n 26 to n 29 may each be an integer of 0 to 4, and n 26 + n 27 and n 28 + n 29 may each be an integer of 5 or less.

Provided that at least one of R 70 and R 71 may be OQ, one to three OQs may be contained in one aromatic ring, and one to four OQs may be contained in another aromatic ring.

[Chemical Formula 13]

Figure pat00029

In Formula 13,

R 74 to R 81 may be a C1 to C30 alkyl groups each independently represent a hydrogen atom or a substituted or unsubstituted, n 30 and n 31 may be an integer from 1 to 5, respectively, Q is as defined in the formula (9) same.

The photosensitive diazoquinone compound may be included in the positive photosensitive resin composition in an amount of 5 to 100 parts by weight, specifically 10 to 50 parts by weight, based on 100 parts by weight of the alkali-soluble resin. When it is included in the above range, the pattern can be formed well with no residue by exposure, and a good pattern can be obtained without loss of film thickness upon development.

(D) Solvent

The solvent is not particularly limited, but specific examples thereof include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether and propylene glycol methyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid alkyl esters such as methyl lactate and ethyl lactate; Hydroxyacetic acid alkyl esters such as methylhydroxyacetate, ethylhydroxyacetate and butylhydroxyacetate; Alkoxyalkyl esters such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-hydroxypropionic acid alkyl esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate and propyl 2-hydroxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-hydroxy-2-methylpropionic acid alkyl esters such as methyl 2-hydroxy-2-methylpropionate and ethyl 2-hydroxy-2-methylpropionate; 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; Esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate and methyl 2-hydroxy-3-methyl butanoate; Or ethyl pyruvate. Examples of the ketone acid esters include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide Benzyl alcohol, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, benzoic acid, Ethyl benzoate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc. These may be used alone or in combination of two or more.

In view of the miscibility and reactivity of the solvent, glycol ethers such as ethylene glycol monoethyl ether and the like; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2-hydroxyethyl propionate; Diethylene glycol such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.

The solvent is preferably used in an amount of 100 to 500 parts by weight based on 100 parts by weight of the alkali-soluble resin. When the content of the solvent is within the above range, a film having a sufficient thickness can be coated, and the solubility and coatability can be excellent.

(E) Other compounds

(E-1) Silane  compound

The positive photosensitive resin composition may further include a silane compound. The silane compound can improve adhesion between the positive photosensitive resin composition and the substrate.

Examples of the silane compound include compounds represented by the following Chemical Formulas 14 to 16; Vinyltrimethoxysilane, vinyltriethoxysilane, vinyltrichlorosilane, vinyltris (? -Methoxyethoxy) silane; 3-acryloxypropyltrimethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3- - methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane; And carbon-carbon unsaturated bond-containing silane compounds such as trimethoxy [3- (phenylamino) propyl] silane, but are not limited thereto.

[Chemical Formula 14]

Figure pat00030

In formula (14), R 20 is a vinyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and specifically, 3- (meth) acryloxypropyl, ) ≪ / RTI > profile.

In Formula 14, R < 21 > To R 23 are each independently a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkyl group, or a halogen, where R 21 To R 23 At least one of them is an alkoxy group or halogen, specifically, the alkoxy group may be a C1 to C8 alkoxy group, and the alkyl group may be a C1 to C20 alkyl group.

[Chemical Formula 15]

Figure pat00031

Wherein R 24 is -NH 2 or -CH 3 CONH, and R 25 to R 27 are each independently a substituted or unsubstituted C 1 to C 20 alkoxy group, specifically, the alkoxy group is OCH 3 or OCH 2 CH 3 , and n 34 may be an integer of 1 to 5.

[Chemical Formula 16]

Figure pat00032

In Formula 16, R < 28 > To R 31 are each independently a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 unsubstituted alkoxy groups, specifically, CH 3 or OCH 3 Lt; / RTI >

In the above formula (16), R 32 and R 33 may each independently be a substituted or unsubstituted amino group, and specifically may be NH 2 or CH 3 CONH. And n 35 and n 36 may be an integer of 1 to 5, respectively.

The silane compound may be used in an amount of 0.1 to 30 parts by weight based on 100 parts by weight of the alkali-soluble resin.

When it is used within the above range, the adhesion to the upper and lower film layers is excellent, and the remaining film is not left after development, and the mechanical properties such as tensile strength, elongation and the like as well as optical characteristics such as transmittance can be improved.

(E-2) Dissolution regulator

Examples of the dissolution controlling agent used in the positive photosensitive resin composition include compounds represented by the following formulas (17) to (22), but the present invention is not limited thereto.

[Chemical Formula 17]

Figure pat00033

In Formula 17,

R 82 to R 84 are the same or different and are each independently hydrogen or a substituted or unsubstituted alkyl group,

R 85 To R 89 are the same or different from each other and are each independently H, OH, or a substituted or unsubstituted alkyl group, specifically, the alkyl group may be CH 3 ,

and n 32 is an integer of 1 to 5.

[Chemical Formula 18]

Figure pat00034

In Formula 18,

R 90 to R 95 are the same or different and are each independently H, OH, or a substituted or unsubstituted alkyl group,

A 9 is CR 213 R 214 or a single bond, R 213 and R 214 are the same or different from each other and are each independently hydrogen or a substituted or unsubstituted alkyl group, specifically, the alkyl group may be CH 3 ,

n 33 + n 34 + n 35 And n36 + n37 + n38 are the same or different from each other, and each independently is an integer of 5 or less.

[Chemical Formula 19]

Figure pat00035

In the above formula (19)

R 96 to R 98 are the same or different and are each independently hydrogen or a substituted or unsubstituted alkyl group,

n 39 , n 40, and n 43 are the same or different from each other, and are each independently an integer of 1 to 5,

n 41 and n 42 are the same or different from each other and each independently an integer of 0 to 4;

[Chemical Formula 20]

Figure pat00036

In the above formula (20)

R 99 To R < 104 > are the same or different and are each independently hydrogen, OH, or a substituted or unsubstituted alkyl group,

n 44 To n 47 are the same or different and are each independently an integer of 1 to 4,

Provided that n 44 + n 46 and n 45 + n 47 are each independently an integer of 5 or less.

[Chemical Formula 21]

Figure pat00037

In Formula 21,

R 105 is a substituted or unsubstituted alkyl group, specifically, CH 3 ,

R 106 to R 108, which may be the same or different from each other, are each independently hydrogen or a substituted or unsubstituted alkyl group,

n 48 , n 50 and n 52 are the same or different and are each independently an integer of 1 to 5,

n 49 , n 51 and n 53 are the same or different from each other, and are each independently an integer of 0 to 4,

Provided that n 48 + n 49 , n 50 + n 51 and n 52 + n 53 are each independently an integer of 5 or less.

[Chemical Formula 22]

Figure pat00038

In Formula 22,

R 109 to R 111 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group, specifically, CH 3 ,

R 112 to R 115 are the same or different and are each independently hydrogen or a substituted or unsubstituted alkyl group,

n 54 , n 56 and n 58 are the same or different and are each independently an integer of 1 to 5,

n 55 , n 57 and n 59 are the same or different and are each independently an integer of 0 to 4,

n 60 is an integer of 1 to 4,

N54 + n55 , n56 + n57, and n58 + n59 each independently represent an integer of 5 or less.

The dissolution controlling agent may be used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the alkali-soluble resin.

When it is used within the above-mentioned range, the developing speed can be controlled, and an appropriate residual film ratio, high sensitivity, and the effect of eliminating residue can be improved.

(E-3) Acid generator

The acid generator is a catalyst for the dehydration reaction of the phenolic hydroxyl group-containing polyamide of the polybenzoxazole precursor and the cyclization reaction, and the cyclization reaction can proceed smoothly even if the curing temperature is lowered.

Further, a suitable surfactant or leveling agent may be further used as an additive in order to prevent unevenness in film thickness or to improve developability.

The acid generator may be used in an amount of 1 to 20 parts by weight, preferably 1.5 to 10 parts by weight, more preferably 1.5 to 8 parts by weight, based on 100 parts by weight of the alkali-soluble resin. When the above compound is used in an amount of less than 1 part by weight, the closed rate of the polymer is lowered, the curing is insufficient, and the film characteristics are poor. When the amount is more than 20 parts by weight, the exposed part is not dissolved in the aqueous alkali solution It is difficult to proceed with the patterning.

Further, in order to prevent unevenness in film thickness or to improve developability, a suitable surfactant or leveling agent may be further used as an additive.

The step of forming a pattern using the positive photosensitive resin composition according to one embodiment of the present invention comprises the steps of: applying the positive photosensitive resin composition on a support substrate; Drying the applied composition to form a photosensitive polybenzoxazole precursor film; Exposing the polybenzoxazole precursor film; A step of developing the exposed polybenzoxazole precursor film with an alkali aqueous solution to produce a photosensitive resin film; And a step of heating the photosensitive resin film.

The conditions of the step of applying the photosensitive resin composition, forming the pattern by exposure and development are well known in the art, and therefore, a detailed description thereof will be omitted herein.

According to another embodiment of the present invention, there is provided a photosensitive resin film produced using the positive photosensitive resin composition.

The photosensitive resin film may be used as an insulating film, a buffer film, or a protective film.

According to another embodiment of the present invention, there is provided a color filter comprising the photosensitive resin film.

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following Examples are only the preferred embodiments of the present invention, and the present invention is not limited to the following Examples.

Synthetic example  One: Polybenzoxazole  Precursor ( PBO ) Synthesis of

In a four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas injector, and a condenser, 2,2-bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3 And 17.4 g of 3-hexafluoropropane were placed and dissolved in 280 g of N-methyl-2-pyrrolidone (NMP). When the solid was completely dissolved, 9.9 g of pyridine was added to the solution, and 13.3 g of 4,4'-oxydibenzoyl chloride was added to 142 g of N-methyl-2-pyrrolidone (NMP) while maintaining the temperature at 0 to 5 ° C The solution was slowly added dropwise for 30 minutes. After the dropwise addition, the reaction was carried out at 0 to 5 ° C for 1 hour, the temperature was raised to room temperature, and the reaction was terminated by stirring for 1 hour.

To this was added 1.6 g of 5-norbornene-2,3-dicarboxyanhydride and the mixture was stirred at 70 ° C for 2 hours to complete the reaction. The reaction mixture was poured into a solution of water / methanol = 10/1 (volume ratio) to form a precipitate. The precipitate was filtered and sufficiently washed with water, then dried at 80 DEG C under vacuum for 24 hours to obtain a weight average molecular weight of 9,800 A polybenzoxazole precursor (PBO) was prepared.

Synthetic example  2: Polyamic acid  Ester compound ( PAE ) Synthesis of

A four-necked flask equipped with a stirrer, a temperature controller, a nitrogen gas injector and a condenser was charged with 1,3,3a, 4,5,9b-hexahydro-5- (tetrahydro- 3-yl) naphtho [1, 2-c] furan-1,3-dione were placed and dissolved in 132 g of N-methyl-2-pyrrolidone (NMP). At this time, the solid content was 20% by weight. When the solid was completely dissolved, 9.9 g of pyridine was added to the solution, and 5.7 g of ethyl alcohol was slowly added dropwise to the solution for 30 minutes while maintaining the temperature at 0 to 5 캜. The reaction was carried out at 25 ° C for 12 hours after dropwise addition to obtain a diethylester solution of the tetracarboxylic acid dianhydride. 14.9 g of thionyl chloride was slowly added dropwise for 30 minutes while maintaining the temperature at 0 to 5 캜. After the dropwise addition, the mixture was stirred for 30 minutes while maintaining the temperature at 25 ° C, and further stirred for 1 hour and a half to obtain a diethylester dichloride solution of the tetracarboxylic acid dianhydride. While maintaining the temperature of the solution at 0 to 5 占 폚, 22.0 g of 2,2-bis (3-amino-4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane and 19 g In 168 g of NMP was slowly added dropwise for 30 minutes. After the dropwise addition, the temperature was raised to 40 DEG C and the reaction was terminated by stirring at this temperature for 2 hours. The reaction mixture was poured into a solution of water / methanol = 10/1 (volume ratio) to produce a precipitate, and the precipitate was filtered and sufficiently washed with water. Dried at 80 캜 under vacuum for 24 hours to obtain a polyamic acid ester compound (PAE) having a weight average molecular weight (Mw) of 10,200 Were synthesized.

(Preparation of photosensitive resin composition)

The specifications of the components used in the production of the photosensitive resin composition are as follows.

(A) an alkali-soluble resin

(A-1) The polybenzoxazole precursor resin prepared in Synthesis Example 1 was used.

(A-2) The polyamic acid ester precursor resin prepared in Synthesis Example 2 was used.

(A-3) Cresol novolac resin having a weight average molecular weight of 9,300 was used.

(A-4) A methacrylic acid / benzyl methacrylate copolymer acrylic resin having a weight average molecular weight of 28,000 was used.

(B) Dye

(B-1) Cyanine series  dyes

R008 from Kyungin Corporation was used .

The absorbance characteristics of R008 are shown in Fig.

(B-2) Methine system  dyes

 A methine yellow dye represented by the following formula (5-1) (solubility in propylene glycol monomethyl ether acetate (PGMEA) 7) was used.

[Formula 5-1]

Figure pat00039

(B-3) Organic salt  Form dye

YR of Gyeongin Incheon was used.

The absorbance characteristics of the YR are shown in FIG.

(C) Photosensitive Diazoquinone  compound

(23)

Figure pat00040

In the formula (23)

Q was the same as defined in the above formula (9), and 67% of the Q was substituted with the formula (32a).

(D) Dissolution regulator

A compound having a structure represented by the following formula (24) was used.

≪ EMI ID =

Figure pat00041

(E) Silane  compound

A compound having a structure represented by the following formula (25) was used

(25)

Figure pat00042

(F) Acid generator

A compound having a structure represented by the following formula (26) was used

(26)

Figure pat00043

Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, the following examples and comparative examples are for illustrative purposes only and are not intended to limit the present invention.

< Example  1>

4.5 g of the polybenzoxazole precursor (PBO) synthesized in Synthesis Example 1 was mixed at a weight ratio of 5/3/2 of? -Butyrolactone (GBL) / ethyl lactate (EL) / propylene glycol methyl ether (PGME) Dissolved in 25 g of a solvent and dissolved. 1.5 g of a cyanine dye R008, 1 g of photosensitive diazoquinone, 0.2 g of a silane coupling agent, 0.4 g of a dissolution regulator and 0.1 g of an acid generator were added and dissolved. To obtain a positive photosensitive resin composition.

< Example  2>

A positive photosensitive resin composition was obtained in the same manner as in Example 1, except that the polyamic acid ester precursor (PAE) synthesized in Synthesis Example 2 was used instead of the PBO obtained in Synthesis Example 1 of Example 1.

< Example  3>

4.5 g of PBO synthesized in Synthesis Example 1 was added to 25 g of a solvent mixed at a weight ratio of? -Butyrolactone (GBL) / ethyl lactate (EL) / propylene glycol methyl ether (PGME) After dissolving 1.0 g of the cyanine dye R008, 0.5 g of the methylene dye, 1 g of the photosensitive diazoquinone, 0.2 g of the silane coupling agent, 0.4 g of the dissolution regulator and 0.1 g of the acid generator, Followed by filtration to obtain a positive photosensitive resin composition.

< Example  4>

4.5 g of PBO synthesized in Synthesis Example 1 was added to 25 g of a solvent mixed at a weight ratio of? -Butyrolactone (GBL) / ethyl lactate (EL) / propylene glycol methyl ether (PGME) Then, 1.0 g of the cyanine dye R008, 0.5 g of the organic salt type dye YR, 1 g of the photosensitive diazoquinone, 0.2 g of the silane coupling agent, 0.4 g of the dissolution regulator and 0.1 g of the acid generator were added and dissolved and then 0.45 μm of a fluororesin And filtered through a filter to obtain a positive photosensitive resin composition.

< Example  5>

A positive photosensitive resin composition was obtained in the same manner as in Example 3, except that the PAE synthesized in Synthesis Example 2 was used instead of PBO in Example 3.

< Example  6>

A positive photosensitive resin composition was obtained in the same manner as in Example 4, except that the PAE synthesized in Synthesis Example 2 was used instead of PBO in Example 4.

< Comparative Example  1>

A positive photosensitive resin composition was obtained in the same manner as in Example 1, except that the cresol novolac resin was used in place of the PBO obtained in Synthesis Example 1 of Example 1.

< Comparative Example  2>

A positive photosensitive resin composition was obtained in the same manner as in Example 1, except that an acrylic resin was used in place of the PBO obtained in Synthesis Example 1 of Example 1.

< Comparative Example  3>

A positive photosensitive resin composition was obtained in the same manner as in Example 3, except that the cresol novolac resin was used in place of the PBO obtained in Synthesis Example 1 of Example 3.

< Comparative Example  4>

A positive photosensitive resin composition was obtained in the same manner as in Example 3, except that an acrylic resin was used in place of the PBO obtained in Synthesis Example 1 of Example 3.

&Lt; Evaluation of physical properties &

(1) Coating and pattern formation

The photosensitive resin compositions prepared according to Examples 1 to 6 and Comparative Examples 1 to 4 were applied on a 1 × 10 cm 2 glass substrate to a thickness of 2.5 to 3.5 μm by a spin coating method and prebaked at 90 ° C. for 3 minutes pre-bake). A photomask was placed on the coated film which had been cooled in the atmosphere and exposed to 400 mJ in 50 mJ units at 50 mJ using a high pressure mercury lamp having a wavelength of 365 nm and then exposed to 2.38 wt% aqueous solution of tetramethylammonium hydroxide (TMAH) at room temperature for 60 seconds The exposed portion was dissolved and removed through development, and then washed with pure water for 30 seconds. Subsequently, the obtained pattern was cured at 230 DEG C for 60 minutes using an oven to prepare a patterned film.

(2) Sensitivity measurement

The sensitivity was determined as the optimal exposure time after exposure and development, in which the 120 μm L / S pattern was formed with a line width of 1: 1. The degree of scum was confirmed by optical microscope. The results are shown in Table 1 below.

(3) Residual film ratio (%) Measure

The development was carried out by immersing the preliminarily baked film in a 2.38 wt% aqueous solution of tetramethylammonium hydroxide and rinsing with water. The change in film thickness was measured to determine the residual film ratio (thickness after development / thickness before development, unit%) The results are shown in Table 1 below.

Film thickness (占 퐉) Remaining film ratio (%) Sensitivity (mJ / cm 2 ) Scum Preliminary firing After development Example 1 4.17 3.81 91 180 radish Example 2 4.10 3.68 89 150 radish Example 3 4.15 3.55 86 165 radish Example 4 4.12 3.70 90 145 radish Example 5 4.15 3.69 89 160 radish Example 6 4.17 3.59 86 180 radish Comparative Example 1 4.11 3.07 75 280 U Comparative Example 2 4.15 3.71 89 320 U Comparative Example 3 4.12 3.50 85 350 U Comparative Example 4 4.12 3.50 85 300 U

Referring to Table 1, Examples 1 to 6 using PBO and PAE as an alkali-soluble resin in the same composition were found to have superior sensitivity, no residue, and increased residual film ratio. In the case of Comparative Examples 1 to 4, the developability of the resin itself was too large, and the developer was developed up to the unexposed portion, so that the residual film ratio was low and the developing property was fast, but the scum still remained.

(4) Evaluation of luminance and contrast ratio

The color coordinates (x and y) and the luminance (Y) were measured using a colorimeter (Otsuka Co., Ltd., MCPD 3000)

(5) Chemical resistance evaluation

The specimens were immersed in a mixed solvent of N-methylpyrrolidone (NMP) and ethylenediglycol dimethylethylether (EDM) for 10 minutes at room temperature, and then taken out and dried. Using a colorimeter, ), And the results are shown in the following three-point standard method.

○: Excellent processability - No pattern change, del (E *) less than 2.5

△: Fairness is good - There is a little pattern change, del (E *) is 2.5 or more and less than 3.5

Poor: Fairness - Pattern change or del (E *) of 3.5 or higher

(6) Evaluation of heat resistance

The color difference was converted into del (E *) before and after the experiment using a colorimeter, and the result was compared with the following 3-point standard method .

○: Excellent processability - No pattern change, del (E *) less than 2.5

△: Fairness is good - There is a little pattern change, del (E *) is 2.5 or more and less than 3.5

Poor: Fairness - Pattern change or del (E *) of 3.5 or higher

Color coordinates Luminance Chemical resistance
Heat resistance
x y Y Example 1 0.657 0.3215 19.35 Example 2 0.657 0.3225 19.48 Example 3 0.657 0.3277 19.54 Example 4 0.657 0.3273 19.50 Example 5 0.657 0.3279 19.13 Example 6 0.657 0.3280 19.10 Comparative Example 1 0.657 0.3220 18.10 × × Comparative Example 2 0.657 0.3215 18.28 × × Comparative Example 3 0.657 0.3278 18.50 × × Comparative Example 4 0.657 0.3278 18.49 × ×

According to the above Table 2, in the case of the composition examples 1 to 6 using the PBO resin and the PAE resin including the dye according to one embodiment, the transparency of the resin film itself is high, so that it is expressed in the same brightness as the dye, Can be confirmed. However, in Comparative Examples 1 to 4, it was confirmed that yellow novolak occurred in the case of novolac itself, and in case of acrylic resin, color change occurred due to poor heat resistance and brightness was lowered. Also, it was confirmed that the chemical resistance and the heat resistance were excellent in the case of the composition using the PBO resin and the PAE resin.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

Claims (14)

(A) an alkali-soluble resin comprising a repeating unit represented by the following formula (1), a repeating unit represented by the following formula (2), or a combination thereof;
(B) a dye comprising a cyanine dye represented by the following formula (3);
(C) a photosensitive diazoquinone compound; And
(D) Solvent
Wherein the positive photosensitive resin composition is a positive photosensitive resin composition.
[Chemical Formula 1]
Figure pat00044

(2)
Figure pat00045

(3)
Figure pat00046

(In the above formulas (1) and (2)
X 1 And X 2 are each independently a substituted or unsubstituted C6 to C30 aromatic organic group, Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C30 aromatic organic group, a substituted or unsubstituted di monovalent C1 to C30 aliphatic organic group, or a substituted or unsubstituted 2 to hexavalent C3 to C30 alicyclic organic ring, R 14 and R 15 are C1 to C20 each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted An alkyl group, a substituted or unsubstituted C1 to C20 haloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 alkenyl group, a substituted or unsubstituted C1 to C20 alkynyl group, A substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, Substituted or unsubstituted C2 to C20 heterocycloalkenyl groups, substituted or unsubstituted C2 to C20 heterocycloalkynyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, Or a substituted or unsubstituted C1 to C20 alkyl (meth) acrylate group.
X 3 and X 4 are each independently a carbon atom, an oxygen atom or a sulfur atom, Y 3 and Y 4 are each independently a single bond, -O-, - (CH 2 ) m COO- (O Lt; = m &lt; = 5), -OCO-, -NH- or -CONH-,
Z 1 and Z 2 are each a ring substituent having one double bond,
R 3 to R 14 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 haloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, A substituted or unsubstituted C1 to C20 alkenyl group, a substituted or unsubstituted C1 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 An aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted C1 to C20 alkyl (meth) acrylate group,
A is a halogen ion, ClO 4 - one, to an ionic compound represented by formula 3-2 or formula 3-1, to -, BF 4 -, SbF 6 -, CF 3 SO 3 -, N (SO 2 CF 3) 2 It is either.)
[Formula 3-1]
Figure pat00047

[Formula 3-2]
Figure pat00048

The method according to claim 1,
Wherein the alkali-soluble resin is a polybenzoxazole precursor, a polyamic acid ester, a polyimide, or a combination thereof.
The method according to claim 1,
In the formula (3), Z 1 and Z 2 are each a substituent represented by the following formula (4-1) or a substituent represented by the following formula (4-2).
[Formula 4-1]
Figure pat00049

[Formula 4-2]
Figure pat00050

(In formulas (4-1) and (4-2)
R and R 'are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkenyl group, A substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkenyl group, a substituted or unsubstituted C 3 to C 20 cycloalkynyl group, a substituted or unsubstituted C 2 to C 20 heterocycloalkyl group , A substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group to be.)
The method according to claim 1,
In the formula (3), each of R 6 to R 11 is independently a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkyl (meth) acrylate group.
The method according to claim 1,
In Formula 3, A is a halogen ion, CF 3 SO 3 - or N (SO 2 CF 3 ) 2 - .
The method according to claim 1,
Wherein the cyanine dye has a wavelength of light of 400 to 700 nm re-emitted.
The method according to claim 1,
When the alkali-soluble resin is a combination of the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2)
Wherein the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) are contained in an amount of 5: 95 to 95: 5 mol% based on the total amount of the alkali-soluble resin.
The method according to claim 1,
When the alkali-soluble resin is a combination of the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2)
Wherein the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) are contained in an amount of 60: 40 to 95: 5 mol% based on the total amount of the alkali-soluble resin.
The method according to claim 1,
Wherein the dye further comprises a methine-based dye represented by the following formula (5).
[Chemical Formula 5]
Figure pat00051

(Wherein R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, an ether group, an amine group or an amine derivative group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, a substituted or unsubstituted C3 to C20 cycloalkynyl group , A substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkenyl group, a substituted or unsubstituted C2 to C20 heterocycloalkynyl group, or a substituted or unsubstituted C6 to C30 aryl group to be).
The method according to claim 1,
Wherein the dye further comprises an organic salt type dye represented by the following formula (6).
[Chemical Formula 6]
Figure pat00052

(Wherein R 1 to R 3 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C3 to C20 cycloalkyl group, and R 1 to R 3 are all hydrogen However,
R 4 is selected from the group consisting of substituted or unsubstituted C 1 to C 20 alkyl groups, substituted or unsubstituted C 3 to C 20 heterocycloalkyl groups, substituted or unsubstituted C 3 to C 20 heteroaryl groups, and combinations thereof, and imine A pyrazolone group, a fuchsine group, an anthraquinone group, and a combination thereof), an azo group, an azo group, a pyrazolone group, a fuchsine group, an anthraquinone group, and combinations thereof.
The method according to claim 1,
Wherein the positive photosensitive resin composition further comprises at least one of a silane compound, a dissolution regulator, and an acid generator.
The method according to claim 1,
The positive photosensitive resin composition
With respect to 100 parts by weight of the alkali-soluble resin (A)
1 to 80 parts by weight of the dye (B);
5 to 100 parts by weight of the photosensitive diazoquinone compound (C); And
50 to 500 parts by weight of the solvent (D)
Wherein the positive photosensitive resin composition is a positive photosensitive resin composition.
A photosensitive resin film produced by using the positive photosensitive resin composition according to any one of claims 1 to 12. A color filter comprising the photosensitive resin film according to claim 13.
KR20130037694A 2013-04-05 2013-04-05 Positive type photosensitive resin composition for color filter and color filter using the same KR20140121209A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20230095572A (en) * 2021-12-22 2023-06-29 삼성에스디아이 주식회사 Photosensitive resin composition, photosensitive resin layer, redistribution layer and semiconductor device using the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20230095572A (en) * 2021-12-22 2023-06-29 삼성에스디아이 주식회사 Photosensitive resin composition, photosensitive resin layer, redistribution layer and semiconductor device using the same

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