KR20170140888A - Red colored photosensitive resin composition, color filter and display device having the same - Google Patents

Abstract

A red colored photosensitive resin composition according to the present invention comprises: a coloring agent including a C.I. pigment red 177, a compound represented by chemical formula 1, and a compound represented by chemical formula 2; and a photopolymerization initiator including a compound represented by chemical formula 3, wherein the compound represented by chemical formula 1 and the compound represented by chemical formula 2 are included in a weight ratio of 2:8 to 8:2. The red colored photosensitive resin composition according to the present invention can suppress a drop in reliability of a red photoresist (PR) when applying the red PR to a photo-alignment model.

Description

TECHNICAL FIELD [0001] The present invention relates to a red photosensitive resin composition, a color filter including the red color photosensitive resin composition,

The present invention relates to a red photosensitive resin composition, a color filter including the same, and a display device.

A color filter may be embedded in a color imaging device of an image sensor such as a complementary metal oxide semiconductor (CMOS), a charge coupled device (CCD), etc., and may be used to actually obtain a color image . In addition, the color filter is widely used for a photographing element, a plasma display panel (PDP), a liquid crystal display (LCD), a field emission display (FEL), a light emitting display (LED) and the like.

Such a color filter usually has a structure in which a pigment corresponding to each color of red, green and blue is uniformly coated on a substrate, a colored photosensitive resin composition containing a coloring agent is uniformly coated, then exposed and developed, and heated and thermally cured Is repeated according to each color to form a pixel corresponding to each color.

On the other hand, a contact rubbing method in which a polymer film such as polyimide is applied to a substrate such as glass and the surface is rubbed in a predetermined direction using fibers such as nylon or polyester is used as a conventional method of orienting the liquid crystal. However, the liquid crystal alignment by the contact type rubbing method as described above is advantageous in that a simple and stable alignment performance of liquid crystal can be obtained. However, when the fibers and the polymer film are rubbed, fine dust or electrostatic discharge (ESD) May be damaged, and as the rolls become larger due to an increase in the processing time and a larger size of the glass, difficulties such as unevenness of rubbing strength may cause serious problems in manufacturing the liquid crystal panel.

In order to solve the problems of the contact type rubbing method as described above, the photoreactive material (optical isomerization, photo dimerization, photodegradation) caused by the linearly polarized UV to the photoreactive polymer binds to a certain arrangement, An optical alignment method through an oriented mechanism is proposed.

However, since the photo alignment method does not maintain or provide stable orientation characteristics in terms of external heat, light, physical impact and chemical impact, there is a problem that productivity or reliability is low as compared with the rubbing method. Therefore, development of a red photosensitive resin composition capable of suppressing a decrease in the reliability of Red PR (photo resist) when applying a photo alignment model is required.

Korean Patent Laid-Open No. 10-2011-0068861 relates to a coloring composition, a color filter and a color liquid crystal display device, which comprises (A) a colorant, (B) a binder resin, (C) a polyfunctional monomer, and (D) And a cage-like silsesquioxane having at least one member selected from the group consisting of an unsaturated group and a unsaturated group.

However, the coloring composition of the above document has a problem that the reliability lowering suppression performance is somewhat deteriorated when applied to the photo alignment model.

Korean Patent Publication No. 10-2011-0068861 (June 22, 2011)

It is an object of the present invention to provide a red photosensitive resin composition capable of suppressing a reduction in reliability of Red PR when applied to a photo-alignment model.

The present invention also provides a color filter having excellent reliability of Red PR and an image device including the same.

In order to solve the above problems, the red photosensitive resin composition of the present invention is a red photosensitive resin composition. Pigment Red 177, a colorant comprising a compound represented by the following formula (1) and a compound represented by the following formula (2); And a photopolymerization initiator comprising a compound represented by the following formula (3), wherein the compound represented by the following formula (1) and the compound represented by the following formula (2) are contained in a weight ratio of 2: 8 to 8: 2 .

[Chemical Formula 1]

(2)

(3)

In Formula 3,

, COR₁₆ 또는 NO₂이고;R ₁ to R ₈ are each independently hydrogen, C ₁ -C ₂₀ alkyl,

, COR _16, or NO _2, and;

이며;Provided that at least one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ or R ₇ and R ₈ is

;

R ₉ to R ₁₂ are each independently hydrogen, optionally substituted C ₁ -C ₂₀ alkyl; Or substituted or unsubstituted phenyl;

X is CO or a direct bond;

R ₁₃ is selected from optionally substituted C ₁ -C ₂₀ alkyl, C ₂ -C ₁₂ alkenyl, C ₄ -C ₈ cycloalkenyl, C ₂ -C ₁₂ alkynyl, C ₃ -C ₁₀ cycloalkyl, phenyl or naphthyl (Both of which are optionally substituted);

R ₁₄ is hydrogen, C ₃ -C ₈ cycloalkyl, C ₂ -C ₅ alkenyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₂₀ alkyl, phenyl or naphthyl;

R ₁₅ is C ₆ -C ₂₀ aryl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of phenyl, halogen, C ₁ -C ₄ haloalkyl, CN, NO ₂ , OR ₁₇ , SR _{18, NR 19 R 20, PO} (OC k H 2k + 1) 2, SO-C 1 -C 10 alkyl, SO ₂ -C ₁ -C ₁₀ alkyl by, one or more O, S or NR ₂₆ is interposed a C ₂ -C ₂₀ alkyl substituted by the, or each of which is unsubstituted halogen, or more than _{1 COOR 17, CONR 19 R 20} , phenyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₂₀ heteroaryl Substituted by C ₁ -C ₂₀ alkyl substituted by aryl, C ₆ -C ₂₀ aryloxycarbonyl, C ₃ -C ₂₀ heteroaryloxycarbonyl, OR ₁₇ , SR ₁₈ or NR ₁₉ R ₂₀ ;

R ₁₆ is C ₆ -C ₂₀ aryl unsubstituted or substituted by one or more C ₁ -C ₂₀ alkoxy or C ₁ -C ₂₀ alkyl;

R ₁₇ is C ₁ -C ₄ haloalkyl;

Wherein R ₁₈ is hydrogen, C ₂ -C ₁₂ alkenyl, C ₃ -C ₂₀ cycloalkyl or phenyl-C ₁ -C ₃ alkyl, wherein C ₂ -C ₁₂ alkenyl, C ₃ -C ₂₀ cycloalkyl or phenyl- C ₁ -C ₃ alkyl is interrupted or interrupted by one or more O, S, CO, NR ₂₆ or COOR ₁₇ ;

Or R ₁₈ is unsubstituted or substituted with one or more of OH, SH, CN, C ₃ -C ₆ alkenoxy, OCH ₂ CH ₂ CN, OCH ₂ CH ₂ (CO) O (C ₁ -C ₄ alkyl) _{CO) - (C 2 -C 4} ) alkenyl, O (CO) - (C 1 -C 4 alkyl), O (CO) - phenyl, or (CO) or a C ₁ -C ₂₀ alkyl substituted by oR ₁₇ ;

Or R ₁₈ is C ₂ -C ₂₀ alkyl interrupted by one or more O, S, CO, NR ₂₆ or COOR ₁₇ ;

Or R ₁₈ is (CH ₂ CH ₂ O) _n H, (CH ₂ CH ₂ O) _n (CO) - (C ₁ -C ₈ alkyl), C ₂ -C ₈ alkanoyl or C ₃ -C ₆ alkenoyl ;

Or R ₁₈ is benzoyl which is unsubstituted or substituted by one or more C ₁ -C ₆ alkyl, halogen, OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylsulfanyl;

에 의해 치환되며;Or R ₁₈ is phenyl, naphthyl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C ₁ -C ₁₂ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₁₂ alkoxy, CN, NO _2, phenyl, -C ₁ -C ₃ alkyloxy, phenoxy, C ₁ -C ₁₂ alkyl sulfanyl, phenylsulfanyl, N (C ₁ -C ₁₂ alkyl) _2, diphenylamino, (CO ) O (C ₁ -C ₈ alkyl), (CO) -C ₁ -C ₈ alkyl, (CO) N (C ₁ -C ₈ alkyl) ₂ or

Lt; / RTI >

X ₂ is O, CO, S or a direct bond;

R ₁₉ and R ₂₀ are each independently selected from the group consisting of hydrogen, C ₁ -C ₂₀ alkyl, C ₂ -C ₄ hydroxyalkyl, C ₂ -C ₁₀ alkoxyalkyl, C ₂ -C ₅ alkenyl, C ₃ -C ₂₀ cycloalkyl , phenyl, -C ₁ -C ₃ alkyl, C ₁ -C ₈ alkanoyl, C ₁ -C ₈ alkanoyloxy, C ₃ -C ₁₂ alkenyl _{alkanoyl, SO 2 - (C 1 -C} 4 haloalkyl), or benzoyl, or ;

Or R ₁₉ and R ₂₀ are phenyl, naphthyl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₁₂ alkyl, benzoyl or C ₁ -C _12, or substituted by alkoxy;

에 의해 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR₁₇이 개재된 C₃-C₂₀ 시클로알킬에 의해 치환되거나;Or R ₁₉ and R ₂₀ together with the N-atom to which they are attached form a 5-or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR ₁₇ , membered saturated or unsaturated ring is unsubstituted or substituted, or one or more C ₁ -C ₂₀ alkyl 1, C ₁ -C _{20 alkoxy, = O, oR 17, SR} 18, NR 21 R 22, (CO) R 23, NO 2, halogen, C ₁ -C ₄ - haloalkyl, CN, phenyl,

Or by C ₃ -C ₂₀ cycloalkyl interrupted or interrupted by one or more O, S, CO or NR ₁₇ ;

, 할로겐, NO₂, CN, 페닐에 의해 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR₁₇이 개재된 C₃-C₂₀ 시클로알킬에 의해 치환된 헤테로방향족 고리계를 형성하고;Or R ₁₉ and R ₂₀ together with the N- atom to which they are attached, unsubstituted or substituted by one or more C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₂₀ alkoxy, = O, OR ₁₇ , SR ₁₈ , NR ₂₁ R ₂₂ , (CO) R ₂₃ ,

Form a heteroaromatic ring system substituted by halogen, NO ₂ , CN, phenyl, or C ₃ -C ₂₀ cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR ₁₇ ;

R ₂₁ and R ₂₂ are each independently hydrogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₁₀ cycloalkyl or phenyl;

Or R ₂₁ and R ₂₂ together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR ₂₆ , The unsubstituted or unsaturated rings are not condensed or the benzene ring is condensed to the 5- or 6-membered saturated or unsaturated ring;

R ₂₃ is hydrogen, OH, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₂₀ alkyl which is non-interrupted or interrupted by at least one O, CO or NR ₂₆ , , S, CO or NR ₂₆ intervening C ₃ -C ₂₀ cycloalkyl, or R ₂₃ is phenyl, naphthyl, phenyl-C ₁ -C ₄ alkyl, OR ₁₇ , SR ₁₈ or NR ₂₁ R ₂₂ ;

R ₂₄ is (CO) OR ₁₇ , CONR ₁₉ R ₂₀ , (CO) R ₁₇ ; Or R ₂₄ has the same meaning as R ₁₉ and R ₂₀ ;

R ₂₅ is COOR ₁₇ , CONR ₁₉ R ₂₀ , (CO) R ₁₇ ; Or R ₂₅ has the same meaning as R ₁₇ ;

에 의해 치환된 페닐이고;R ₂₆ is hydrogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₂₀ alkyl interrupted by one or more O or CO, or phenyl-C ₁ -C ₄ alkyl, Or C ₃ -C ₈ cycloalkyl interrupted by one or more O or CO, or (CO) R ₁₉ , or is phenyl which is unsubstituted or substituted by one or more C ₁ -C ₂₀ alkyl, halogen, C ₁ -C ₄ halo _{alkyl, oR 17, SR 18, NR} 19 R 20 or

Lt; / RTI >;

또는

가 분자 내에 존재한다.However, at least one

or

Is present in the molecule.

The present invention also provides a color filter comprising a cured product of the red photosensitive resin composition described above.

Further, the present invention provides an image display device including the color filter described above.

The red photosensitive resin composition according to the present invention has an advantage that the reliability can be reduced, and the reliability of Red PR can be suppressed, particularly when applied to a photo-alignment model.

In addition, the color filter and the image display device using the red photosensitive resin composition according to the present invention are advantageous in that a reduction in reliability is suppressed and excellent reliability is obtained.

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

When a member is referred to as being " on "another member in the present invention, this includes not only when a member is in contact with another member but also when another member exists between the two members.

Whenever a part is referred to as "including " an element in the present invention, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

≪ Red photosensitive resin composition >

The red photosensitive resin composition according to the present invention contains C.I. Pigment Red 177, a colorant comprising a compound represented by the following formula (1) and a compound represented by the following formula (2); And a photopolymerization initiator comprising a compound represented by the following formula (3), wherein the compound represented by the following formula (1) and the compound represented by the following formula (2) are contained in a weight ratio of 2: 8 to 8: 2 .

coloring agent

The colorant according to the present invention is a colorant. Pigment Red 177, a compound represented by the following formula (1) and a compound represented by the following formula (2), wherein the compound represented by the following formula (1) and the compound represented by the following formula (2) are mixed at a weight ratio of 2: 8 to 8: .

[Chemical Formula 1]

(2)

The colorant according to the present invention includes all of the above three pigments, and the compounds represented by the general formulas (1) and (2) are included in a specific amount, thereby increasing the reliability of the red photosensitive resin composition. It is possible to solve problems such as decomposition of the pigment, generation of foreign matter, and reduction of chromaticity. In addition, it is possible to provide a red photosensitive resin composition having an excellent adhesion property, and in particular, it is advantageous in that reliability can be suppressed even when it is applied to a photo-alignment model.

Specifically, the compound represented by Formula (1) and the compound represented by Formula (2) are contained in a weight ratio of 2: 8 to 8: 2, and the weight ratio of 2: 8 to 8: .

When the compound represented by the formula (1) and the compound represented by the formula (2) are contained in the above-mentioned ratio by weight, the NMP solvent resistance is excellent. When the compound represented by Formula 1 and the compound represented by Formula 2 are included in the weight ratio, the chemical resistance may be slightly lowered after photo-alignment (UV irradiation) and the NMP solvent resistance may be lowered. .

In one embodiment of the present invention, the colorant is added in an amount of 5 to 50 parts by weight, preferably 5 to 30 parts by weight, more preferably 5 to 10 parts by weight, per 100 parts by weight of the red photosensitive resin composition according to the present invention .

When the colorant is contained within the above range, there is an advantage in that coloring power, solvent resistance or adhesion is excellent.

When the colorant is included in the range below the above range, the coloring power may be lowered. If the colorant is added in the above range, the solvent resistance or adhesion may be lowered.

The compound represented by the formula (1) or the compound represented by the formula (2) may be directly synthesized and used, and commercially available forms may be purchased and used. The compound represented by the above formula (1) Pigment Red 254, and Irgaphor (R) Red S 3620 CF of BASF is preferable as the product of the compound represented by Formula (2).

In one embodiment of the present invention, the amount of the C.I. 5 to 70% by weight of Pigment Red 177, 5 to 60% by weight of the compound represented by the formula (1) and 5 to 60% by weight of the compound represented by the formula (2).

The C.I. When Pigment Red 177, the compound represented by Formula 1, and the compound represented by Formula 2, respectively, are contained in the above range, the coloring ability may be somewhat lowered. If the above range is exceeded, pattern formation may be somewhat difficult It may cause a decrease in adhesion.

The C.I. When Pigment Red 177, the compound represented by Formula 1 and the compound represented by Formula 2 are included together while satisfying the above-described content range, the adhesion can be prevented from lowering and the reliability can be increased. have.

The colorant may be the C.I. Pigment Red 177, the compound represented by Formula 1, and the compound represented by Formula 2, in addition to the red pigment.

The pigment may be an organic pigment or an inorganic pigment generally used in the art. The pigment may be subjected to a surface treatment using a pigment treatment, a pigment derivative into which an acidic group or a basic group is introduced, a graft treatment of the surface of the pigment with a polymer compound, an atomization treatment using a sulfuric acid atomization method or the like, A cleaning treatment with an organic solvent or water, or a treatment for removing ionic impurities by ion exchange or the like.

The organic pigments may be various pigments used in printing ink, ink jet ink, etc. Specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, A pyranthrone pigment, a diketopyrrolopyrrole pigment, an anthraquinone pigment, an anthraquinone pigment, an anthrone pigment, an anthrone pigment, an indanthrone pigment, a pravanthrone pigment, a pyranthrone pigment, a diketopyrrolopyrrole pigment And the like.

As the inorganic pigment, metal compounds such as metal oxides and metal complex salts can be used. Specific examples of the inorganic pigments include iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, A black pigment, a titanium black, and an oxide of a metal such as a pigment that mixes red, green, and blue to give a black color, or a composite metal oxide.

It is preferable to use a pigment dispersion in which the particle diameter of the pigment is uniformly dispersed. An example of a method for uniformly dispersing the particle diameter of the pigment includes a method of dispersing the pigment by adding a pigment dispersant. According to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained, Do.

Examples of the pigment dispersant include surfactants such as cationic surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, polyester surfactants, and polyamine surfactants. These surfactants may be used singly or in combination of two or more. It does not.

The content of the pigment is in the range of 20 to 90% by weight, preferably 30 to 80% by weight with respect to the total solid content in the pigment dispersion. When the content of the pigment is in the range of 20 to 90% by weight, the viscosity is low, the storage stability is excellent, and the dispersion efficiency is high, which is effective for increasing the contrast ratio.

The pigment dispersant is added for maintenance of deagglomeration and stability of the pigment, and any of those generally used in the art can be used without limitation. Specifically, it is preferable to contain an acrylate-based dispersant containing BMA (butyl methacrylate) or DMAEMA (N, N-dimethylaminoethyl methacrylate). In this case, it is preferable to apply the acrylate-based dispersing agent prepared by the living control method as disclosed in Korean Patent Publication No. 2004-0014311. DISCLOSURE OF THE INVENTION The acrylate- BYK-2000, DISPER BYK-2001, DISPER BYK-2070 and DISPER BYK-2150.

The acrylic dispersants exemplified above may be used alone or in combination of two or more.

As the pigment dispersant, other resin type pigment dispersants other than the acrylic dispersant may be used. The other resin type pigment dispersing agent may be a known resin type pigment dispersing agent, especially a polycarboxylic acid ester such as polyurethane, polyacrylate, unsaturated polyamide, polycarboxylic acid, polycarboxylic acid (partial) Amine salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and their modified products, or free ) Oil-based dispersants such as amides formed by reaction of a polyester having a carboxyl group with poly (lower alkyleneimine) or salts thereof; Soluble resin or water-soluble polymer compound such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; Polyester; Modified polyacrylates; Adducts of ethylene oxide / propylene oxide, and phosphate esters.

DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-160, BYK (trade name) 164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; EFKA-4060, EFKA-4060, EFKA-4055, EFKA-4055, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10 from Lubirzol; Hinoact T-6000, Hinoact T-7000, Hinoact T-8000; available from Kawaken Fine Chemicals; AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823 manufactured by Ajinomoto; FLORENE DOPA-17HF, fluorene DOPA-15BHF, fluorene DOPA-33, and fluorene DOPA-44 are trade names of Kyoeisha Chemical Co., In addition to the above acrylic dispersant, other resin type pigment dispersants may be used alone or in combination of two or more, and may be used in combination with an acrylic dispersant.

The content of the dispersant may be 5 to 60 parts by weight, more preferably 15 to 50 parts by weight, based on 100 parts by weight of the solid content of the pigment, but is not limited thereto. However, if the content of the dispersant is included in the above standard, it is preferable to prevent gelation after dispersion. If the content of the dispersing agent is less than 5 parts by weight, the pigment may become less finely atomized or gelation may occur after dispersion, and when the content of the dispersing agent exceeds 50 parts by weight, the viscosity may become somewhat high .

Light curing Initiator

The red photosensitive resin composition according to the present invention comprises a photopolymerization initiator comprising a compound represented by the following general formula (3). The compound represented by the following general formula (3) may be used as the oxime ester derivative of the benzocarbazole compound described in Korean Patent Publication No. 10-2013-0115272, but is not limited thereto.

(3)

In Formula 3,

, COR₁₆, OR₁₇, 할로겐, NO₂ 또는

이거나; R ₁ to R ₈ are each independently hydrogen, C ₁ -C ₂₀ alkyl,

, COR ₁₆ , OR ₁₇ , halogen, NO ₂ or

;

에 의해 치환된 C₂-C₁₀ 알케닐이거나;Or R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , or R ₇ and R ₈ are each independently

A substituted C ₂ -C ₁₀ alkenyl, or by;

Or R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , or R ₇ and R ₈ are each independently - (CH ₂ ) _p -Y - (CH _{2) q} - or;

이고;Or R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , or R ₇ and R ₈ are each independently

ego;

이고;Provided that at least one pair of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , or R ₇ and R ₈ is

ego;

R ₉ to R ₁₂ are each independently hydrogen, unsubstituted or substituted by one or more halogens, phenyl, CN, OH, SH, C ₁ -C ₄ - alkoxy, (CO) OH or by (CO) O (C ₁ which it is substituted by -C ₄ alkyl) C ₁ -C ₂₀ alkyl;

Or R ₉ to R ₁₂ are each independently phenyl unsubstituted or substituted by one or more C ₁ -C ₆ alkyl, halogen, CN, OR ₁₇ , SR ₁₈ , or NR ₁₉ R ₂₀ ;

Or R ₉ to R ₁₂ are each independently halogen, CN, OR ₁₇ , SR ₁₈ , SOR ₁₈ , SO ₂ R ₁₈ or NR ₁₉ R ₂₀ wherein the substituents OR ₁₇ , SR ₁₈ or NR ₁₉ R ₂₀ are optionally naphthyl a radical R ₁₇ and one with one of the carbon atoms of the ring, R _18, R ₁₉ and / or through a 5- or R ₂₀ forms a 6-membered ring, or;

, COR₁₆ 또는 NO₂이고;Or R ₉ to R ₁₂ are each independently

, COR _16, or NO _2, and;

Y is O, S, NR < ₂₆ > or a direct bond;

p is an integer 0, 1, 2 or 3;

q is an integer 1, 2 or 3;

X is CO or a direct bond;

에 의해 치환된 C₁-C₂₀ 알킬이거나;R ₁₃ is unsubstituted or substituted by one or more _{halogen, R 17, COOR 17, OR} 17, SR 18, CONR 19 R 20, by _{NR 19 R 20, PO (OC} k H 2k + 1) 2 , or

A substituted C ₁ -C ₂₀ alkyl, or by;

Or R ₁₃ is C ₂ -C ₂₀ alkyl interrupted by one or more O, S, SO, SO ₂ , NR _26, or CO;

Or C ₂ -C ₁₂ alkenyl which is interrupted or interrupted by one or more O, CO or NR ₂₆ ,

Wherein the intervening C ₂ -C ₂₀ alkyl and the non-interrupted or interrupted C ₂ -C ₁₂ alkenyl are unsubstituted or substituted by one or more halogens;

Or R ₁₃ is C ₄ -C ₈ cycloalkenyl, C ₂ -C ₁₂ alkynyl, or C ₃ -C ₁₀ cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR ₂₆ ;

, COR₁₆, CN, NO₂, 할로겐, C₁-C₂₀ 알킬, C₁-C₄ 할로알킬, 1개 이상의 O, S, CO 또는 NR₂₆이 개재된 C₂-C₂₀ 알킬에 의해 치환되거나, 또는 이들 각각은 C₃-C₁₀ 시클로알킬에 의해 또는 1개 이상의 O, S, CO 또는 NR₂₆이 개재된 C₃-C₁₀ 시클로알킬에 의해 치환되고;Or R ₁₃ is phenyl or naphthyl, each of which is unsubstituted or substituted by one or more of OR ₁₇ , SR ₁₈ , NR ₁₉ R ₂₀ ,

, COR ₁₆ , CN, NO ₂ , halogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₂₀ alkyl interrupted by one or more O, S, CO or NR ₂₆ or each of which is substituted by C ₃ -C ₁₀ cycloalkyl or one or more by alkyl, O, S, CO or NR ₂₆ via the C ₃ -C ₁₀ cycloalkyl;

k is an integer 1-10;

R ₁₄ is a hydrogen, C ₃ -C ₈ cycloalkyl, C ₂ -C ₅ alkenyl, C ₁ -C ₂₀ alkoxy, or unsubstituted or substituted by one or more halogens, phenyl, C ₁ -C ₂₀ alkyl, phenyl or CN the substituted by C ₁ -C ₂₀ alkyl;

Or R ₁₄ is phenyl or naphthyl, each of which is unsubstituted or substituted by one or more of C ₁ -C ₆ alkyl, C ₁ -C ₄ haloalkyl, halogen, CN, OR ₁₇ , SR ₁₈ and / or NR ₁₉ R ₂₀ ;

Or R ₁₄ is C ₃ -C ₂₀ heteroaryl, C ₁ -C ₈ alkoxy, benzyloxy or phenoxy, and the benzyloxy and phenoxy is unsubstituted or substituted by one or more C ₁ -C ₆ alkyl 1, C ₁ - C ₄ haloalkyl and / or halogen;

R ₁₅ is C ₆ -C ₂₀ aryl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of phenyl, halogen, C ₁ -C ₄ haloalkyl, CN, NO ₂ , OR ₁₇ , SR _{18, NR 19 R 20, PO} (OC k H 2k + 1) 2, SO-C 1 -C 10 alkyl, SO ₂ -C ₁ -C ₁₀ alkyl by, one or more O, S or NR ₂₆ is interposed a C ₂ -C ₂₀ alkyl substituted by the, or each of which is unsubstituted halogen, or more than _{1 COOR 17, CONR 19 R 20} , phenyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₂₀ heteroaryl Substituted by C ₁ -C ₂₀ alkyl substituted by aryl, C ₆ -C ₂₀ aryloxycarbonyl, C ₃ -C ₂₀ heteroaryloxycarbonyl, OR ₁₇ , SR ₁₈ or NR ₁₉ R ₂₀ ;

Or R ₁₅ is hydrogen, C ₂ -C ₁₂ alkenyl, C ₃ -C ₈ cycloalkyl which is interrupted or interrupted by one or more O, CO or NR ₂₆ ;

,

페닐에 의해 치환된 C₁-C₂₀ 알킬이고, 상기 C₁-C₂₀ 알킬은 할로겐, C₁-C₂₀ 알킬, C₁-C₄ 할로알킬, OR₁₇, SR₁₈ 또는 NR₁₉R₂₀에 의해 치환된 페닐에 의해 치환되거나;Or R ₁₅ is unsubstituted or substituted by one or more _{halogen, OR 17, SR 18, C} 3 -C 8 cycloalkyl, C ₃ -C ₂₀ heteroaryl, C ₆ -C ₂₀ aryloxycarbonyl, C ₃ -C _{20 heteroaryloxy-carbonyl, NR 19 R 20, COOR 17} , CONR 19 R 20, PO (OC k H 2k + 1) 2,

,

C ₁ -C ₂₀ alkyl substituted by phenyl, said C ₁ -C ₂₀ alkyl being optionally substituted by halogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, OR ₁₇ , SR ₁₈ or NR ₁₉ R ₂₀ ≪ / RTI > substituted phenyl;

Or R ₁₅ is C ₂ -C ₂₀ alkyl interrupted by one or more O, SO or SO ₂ , said intervening C ₂ -C ₂₀ alkyl is unsubstituted or substituted by one or more of halogen, OR ₁₇ , COOR ₁₇ , CONR ₁₉ R ₂₀ , phenyl or phenyl substituted by OR ₁₇ , SR ₁₈ or NR ₁₉ R ₂₀ ;

Or R ₁₅ is C ₂ -C ₂₀ alkanoyl or benzoyl which is unsubstituted or substituted by one or more C ₁ -C ₆ alkyl, halogen, phenyl, OR ₁₇ , SR ₁₈ or NR ₁₉ R ₂₀ ;

Or R _{15 is} naphthoyl which is unsubstituted or substituted by one or more OR ₁₇ or is C ₃ -C ₁₄ heteroarylcarbonyl;

Or R ₁₅ is C ₂ -C ₁₂ alkoxycarbonyl which is non-interrupted or interrupted by at least one O, said non-interrupted or interrupted C ₂ -C ₁₂ alkoxycarbonyl being unsubstituted or substituted by one or more hydroxyl groups ≪ / RTI >

Or R ₁₅ is phenoxycarbonyl which is unsubstituted or substituted by one or more C ₁ -C ₆ alkyl, halogen, C ₁ -C ₄ haloalkyl, phenyl, OR ₁₇ , SR ₁₈ or NR ₁₉ R ₂₀ ;

Or R ₁₅ is CN, CONR ₁₉ R ₂₀ , NO ₂ , C ₁ -C ₄ haloalkyl, S (O) _m -C ₁ -C ₆ alkyl; S (O) _m -phenyl unsubstituted or substituted by C ₁ -C ₁₂ alkyl or SO ₂ -C ₁ -C ₆ alkyl;

Or R ₁₅ is SO ₂ O-phenyl unsubstituted or substituted by C ₁ -C ₁₂ alkyl; Or diphenylphosphino days or di - (C ₁ -C ₄ alkoxy) - phosphino day and;

m is 1 or 2;

R _'14 has the same meaning as R ₁₄ ;

R _'15 has the same meaning as R _15;

X ₁ is O, S, SO or SO ₂ ;

X ₂ is O, CO, S or a direct bond;

R ₁₆ is C ₆ -C ₂₀ aryl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of phenyl, halogen, C ₁ -C ₄ haloalkyl, CN, NO ₂ , OR ₁₇ , SR ₁₈ , NR ₁₉ R ₂₀ , or C ₁ -C ₂₀ alkyl interrupted by one or more O, S or NR ₂₆ , or each of which is unsubstituted or substituted by one or more of halogen, COOR ₁₇ , CONR R _19, R ₂₀ , phenyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₂₀ heteroaryl, C ₆ -C ₂₀ aryloxycarbonyl, C ₃ -C ₂₀ heteroaryloxycarbonyl, OR ₁₇ , SR ₁₈ or NR ₁₉ or more 1 substituted by R ₂₀ C ₁ -C ₂₀ optionally substituted by alkyl;

Or R ₁₆ is hydrogen, unsubstituted or substituted by one or more halogen, phenyl, OH, SH, CN, C ₃ -C _{6 alkenyl-oxy, OCH 2 CH 2 CN, OCH} 2 CH 2 (CO) O (C 1 -C ₄ alkyl), O (CO) - ( C 1 -C 4 alkyl), O (CO) - phenyl, (CO) OH or (CO) O (C ₁ -C ₄ alkyl) C ₁ -C substituted by ₂₀ alkyl;

Or R ₁₆ is C ₂ -C ₁₂ alkyl interrupted by one or more O, S or NR ₂₆ ;

Or R ₁₆ is (CH ₂ CH ₂ O) _{n + 1} H, (CH ₂ CH ₂ O) _n (CO) - (C ₁ -C ₈ alkyl), C ₂ -C ₁₂ alkenyl or C ₃ -C ₈ Cycloalkyl;

Or R ₁₆ is phenyl substituted by SR ₁₈ , wherein the radical R ₁₈ represents a direct bond to a phenyl or naphthyl ring of a carbazole moiety to which the COR ₁₆ group is attached;

n is an integer from 1 to 20;

R ₁₇ is hydrogen, phenyl -C ₁ -C ₃ alkyl, unsubstituted or substituted by one or more halogen, OH, SH, CN, C ₃ -C _{6 alkenyl-oxy, OCH 2 CH 2 CN, OCH} 2 CH 2 (CO) O (C ₁ -C ₄ alkyl), O (CO) - (C ₁ -C ₄ alkyl), O (CO) - (C ₂ -C ₄ ) alkenyl, O , (CO) O (C ₁ -C ₄ alkyl), C ₃ -C ₂₀ cycloalkyl, SO ₂ - (C ₁ -C ₄ haloalkyl), O (C ₁ -C ₄ haloalkyl) or more O is interposed a C ₃ -C ₂₀ cycloalkyl substituted by C ₁ -C ₂₀ alkyl;

Or R ₁₇ is C ₂ -C ₂₀ alkyl interrupted by one or more O, S or NR ₂₆ ;

Or R ₁₇ is C ₁ -C ₄ halo alkyl;

Or R ₁₇ is _{(CH 2 CH 2 O) n} + 1 H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C ₁ -C ₈ alkanoyl, C ₂ -C ₁₂ C ₃ -C ₆ alkenoyl, or C ₃ -C ₂₀ cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR ₂₆ ;

Or R ₁₇ is C ₁ -C ₈ alkyl-C ₃ -C ₁₀ cycloalkyl which is interrupted or interrupted by one or more O;

Or R ₁₇ is benzoyl which is unsubstituted or substituted by one or more C ₁ -C ₆ alkyl, halogen, OH or C ₁ -C ₃ alkoxy;

에 의해 치환되거나;Or R ₁₇ is phenyl, naphthyl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, OH, C ₁ -C ₁₂ alkyl, C ₁ -C ₁₂ alkoxy, CN, NO ₂ , Phenyl-C ₁ -C ₃ alkyloxy, phenoxy, C ₁ -C ₁₂ alkylsulfanyl, phenylsulfanyl, N (C ₁ -C ₁₂ alkyl) ₂ , diphenylamino or

Lt; / RTI >

또는

가 위치한 페닐 또는 나프틸 고리의 탄소 원자 중 1개에 대한 직접 결합을 형성하고;Or R < ₁₇ >

or

To form a direct bond to one of the carbon atoms of the phenyl or naphthyl ring on which it is located;

Wherein R ₁₈ is hydrogen, C ₂ -C ₁₂ alkenyl, C ₃ -C ₂₀ cycloalkyl or phenyl-C ₁ -C ₃ alkyl, wherein C ₂ -C ₁₂ alkenyl, C ₃ -C ₂₀ cycloalkyl or phenyl- C ₁ -C ₃ alkyl is interrupted or interrupted by one or more O, S, CO, NR ₂₆ or COOR ₁₇ ;

Or R ₁₈ is phenyl which is unsubstituted or substituted by one or more of OH, SH, CN, C ₃ -C ₆ alkenoxy, OCH ₂ CH ₂ CN, OCH ₂ CH ₂ (CO) O (C ₁ -C ₄ alkyl) _{(CO) - (C 2 -C} 4) alkenyl, O (CO) - (C 1 -C 4 alkyl), O (CO) - phenyl, or (CO) substituted by a C ₁ -C ₂₀ alkyl oR ₁₇ ;

Or R ₁₈ is C ₂ -C ₂₀ alkyl interrupted by one or more O, S, CO, NR ₂₆ or COOR ₁₇ ;

Or R ₁₈ is (CH ₂ CH ₂ O) _n H, (CH ₂ CH ₂ O) _n (CO) - (C ₁ -C ₈ alkyl), C ₂ -C ₈ alkanoyl or C ₃ -C ₆ alkenoyl ;

Or R ₁₈ is benzoyl which is unsubstituted or substituted by one or more C ₁ -C ₆ alkyl, halogen, OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylsulfanyl;

에 의해 치환되고;Or R ₁₈ is phenyl, naphthyl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C ₁ -C ₁₂ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₁₂ alkoxy, CN, NO _2, phenyl, -C ₁ -C ₃ alkyloxy, phenoxy, C ₁ -C ₁₂ alkyl sulfanyl, phenylsulfanyl, N (C ₁ -C ₁₂ alkyl) _2, diphenylamino, (CO ) O (C ₁ -C ₈ alkyl), (CO) -C ₁ -C ₈ alkyl, (CO) N (C ₁ -C ₈ alkyl) ₂ or

Lt; / RTI >

R ₁₉ and R ₂₀ are each independently selected from the group consisting of hydrogen, C ₁ -C ₂₀ alkyl, C ₂ -C ₄ hydroxyalkyl, C ₂ -C ₁₀ alkoxyalkyl, C ₂ -C ₅ alkenyl, C ₃ -C ₂₀ cycloalkyl , phenyl, -C ₁ -C ₃ alkyl, C ₁ -C ₈ alkanoyl, C ₁ -C ₈ alkanoyloxy, C ₃ -C ₁₂ alkenyl _{alkanoyl, SO 2 - (C 1 -C} 4 haloalkyl), or benzoyl, or ;

Or R ₁₉ and R ₂₀ are phenyl, naphthyl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₁₂ alkyl, benzoyl or C ₁ -C _12, or substituted by alkoxy;

에 의해 개재 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR₁₇이 개재된 C₃-C₂₀ 시클로알킬에 의해 치환되거나;Or R ₁₉ and R ₂₀ together with the N-atom to which they are attached form a 5-or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR ₁₇ , membered saturated or unsaturated ring is unsubstituted or substituted, or one or more C ₁ -C ₂₀ alkyl 1, C ₁ -C _{20 alkoxy, = O, oR 17, SR} 18, NR 21 R 22, (CO) R 23, NO 2, halogen, C ₁ -C ₄ - haloalkyl, CN, phenyl,

Or by C ₃ -C ₂₀ cycloalkyl interrupted by one or more O, S, CO or NR ₁₇ ;

, 할로겐, NO₂, CN, 페닐에 의해 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR₁₇이 개재된 C₃-C₂₀ 시클로알킬에 의해 치환된 헤테로방향족 고리계를 형성하고;Or R ₁₉ and R ₂₀ together with the N- atom to which they are attached, unsubstituted or substituted by one or more C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₂₀ alkoxy, = O, OR ₁₇ , SR ₁₈ , NR ₂₁ R ₂₂ , (CO) R ₂₃ ,

Form a heteroaromatic ring system substituted by halogen, NO ₂ , CN, phenyl, or C ₃ -C ₂₀ cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR ₁₇ ;

R ₂₁ and R ₂₂ are each independently hydrogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₁₀ cycloalkyl or phenyl;

Or R ₂₁ and R ₂₂ together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR ₂₆ , The unsubstituted or unsaturated rings are not condensed or the benzene ring is condensed to the 5- or 6-membered saturated or unsaturated ring;

R ₂₃ is hydrogen, OH, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₂₀ alkyl which is non-interrupted or interrupted by at least one O, CO or NR ₂₆ , , S, CO or NR ₂₆ intervening C ₃ -C ₂₀ cycloalkyl, or R ₂₃ is phenyl, naphthyl, phenyl-C ₁ -C ₄ alkyl, OR ₁₇ , SR ₁₈ or NR ₂₁ R ₂₂ ;

R ₂₄ is (CO) OR ₁₇ , CONR ₁₉ R ₂₀ , (CO) R ₁₇ ; Or R ₂₄ has the same meaning as R ₁₉ and R ₂₀ ;

R ₂₅ is COOR ₁₇ , CONR ₁₉ R ₂₀ , (CO) R ₁₇ ; Or R ₂₅ has the same meaning as R ₁₇ ;

에 의해 치환된 페닐이고;R ₂₆ is hydrogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₂₀ alkyl interrupted by one or more O or CO, or phenyl-C ₁ -C ₄ alkyl, Or C ₃ -C ₈ cycloalkyl interrupted by one or more O or CO, or (CO) R ₁₉ , or is phenyl which is unsubstituted or substituted by one or more C ₁ -C ₂₀ alkyl, halogen, C ₁ -C ₄ halo _{alkyl, oR 17, SR 18, NR} 19 R 20 or

Lt; / RTI >;

또는

가 분자 내에 존재한다.However, at least one

or

Is present in the molecule.

이다.The compounds of formula (III) are characterized in that they contain at least one anilated unsaturated ring (s) in the carbazole moiety. That is, at least one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , or R ₇ and R ₈ ,

to be.

The substituents comprising alkyl, alkoxy and other alkyl moieties described in the present invention include both straight chain or branched forms, and cycloalkyl includes not only a single ring system but also several cyclic hydrocarbons. The aryls described in the present invention are organic radicals derived from aromatic hydrocarbons by the removal of one hydrogen, with a single or fused ring system, suitably containing from 4 to 7, preferably 5 or 6, ring atoms in each ring And includes a form in which a plurality of aryls are connected by a single bond. Hydroxyalkyl means OH-alkyl in which a hydroxy group is bonded to the above-defined alkyl, and hydroxyalkoxyalkyl means hydroxyalkyl-O-alkyl in which alkoxy is bonded to the above hydroxyalkyl.

The alkyl described in the present invention refers to a straight or branched chain hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, free of unsaturation and bonded to the remainder of the molecule by a single bond.

C ₁ -C ₂₀ alkyl is linear or branched and is, for example, C ₁ -C ₁₈ -, C ₁ -C ₁₄ -, C ₁ -C ₁₂ -, C ₁ -C ₈ -, C ₁ -C ₆ - Or C ₁ -C ₄ alkyl or C ₄ -C ₁₂ - or C ₄ -C ₈ alkyl. Examples are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2,4,4-trimethylpentyl, Decyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl and icosyl. C ₁ -C ₆ alkyl has the same meaning as given above for C ₁ -C ₂₀ alkyl up to the corresponding number of C-atoms.

Unsubstituted or substituted C ₁ -C ₂₀ alkyl containing one or more CC multiple bonds refers to alkenyl as described below.

C ₁ -C ₄ haloalkyl is C ₁ -C ₄ alkyl as defined above, substituted by halogen as defined below. Alkyl radicals are, for example, mono- or multi-halogenated (until all H-atoms are replaced by halogens). This is for example C _n H _x Hal _y where x + y = 2n + 1 and Hal is halogen, preferably F. Specific examples are chloromethyl, trichloromethyl, trifluoromethyl or 2-bromopropyl, especially trifluoromethyl or trichloromethyl.

C ₂ -C ₄ hydroxyalkyl means C ₂ -C ₄ alkyl substituted by one or two O-atoms. Alkyl radicals are linear or branched. Examples are 2-hydroxyethyl, 1-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1 -hydroxybutyl, 4-hydroxybutyl, 3-hydroxybutyl, 2,3-dihydroxypropyl or 2,4-dihydroxybutyl.

C ₂ -C ₁₀ alkoxyalkyl is C ₂ -C ₁₀ alkyl interrupted by one O-atom. C ₂ -C ₁₀ alkyl has the same meaning as given above for C ₁ -C ₂₀ alkyl to the corresponding number of C-atoms. Examples are methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, propoxymethyl, propoxyethyl, propoxypropyl.

C ₂ -C ₂₀ alkyl in which one or more O, S, NR ₂₆ or CO is interrupted is, for example, O, S, NR ₂₆ or CO is 1-9, 1-5, 1-3 or 1 or 2 times do. Where more than one intervening radical is present, they may be of the same kind or different. Two O-atoms are separated by one or more methylene groups, preferably two or more methylene groups, i.e., ethylene. Alkyl groups are linear or branched. For example, the following structural units -CH ₂ -CH ₂ -O-CH ₂ CH ₃ , - [CH ₂ CH ₂ O] _y -CH ₃ wherein y = 1-9, - (CH ₂ -CH _{2 O) 7 -CH 2 CH 3,} -CH 2 -CH (CH 3) -O-CH 2 -CH 2 CH 3, -CH 2 -CH (CH 3) -O-CH 2 -CH 3, -CH 2 -CH ₂ -S-CH ₂ CH ₃ , -CH ₂ -CH (CH ₃ ) -NR ₂₆ -CH ₂ -CH ₃ , -CH ₂ -CH ₂ -COO-CH ₂ CH ₃ or -CH ₂ -CH CH ₃ ) -OCO-CH ₂ -CH ₂ CH ₃ .

,

,

및 상응하는 고리를 포함하는 것으로 의도된다. 추가의 예는

,

,

이고, 보다 상세하게는

, 또는

과 같은 구조일 뿐만 아니라 가교 또는 융합된 고리계, 예를 들어

,

등이 또한 상기 용어에 의해 포함되는 것으로 의도된다.In the present invention, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₈ cycloalkyl should be understood as alkyl containing one or more rings. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, especially cyclopentyl and cyclohexyl. C ₃ -C ₁₀ cycloalkyl in the context of the present invention may also be a bicyclic ring, i.e. a bridged ring,

,

,

And the corresponding rings. A further example is

,

,

More specifically,

, or

But also crosslinked or fused ring systems, for example

,

Etc. are also intended to be encompassed by the term.

C ₃ -C ₂₀ cycloalkyl interrupted by O, S, CO, NR ₂₆ has the meanings given above, in which one or more of the CH ₂ - groups of the alkyl is exchanged for O, S, CO or NR ₂₆ .

C ₁ -C ₈ alkyl-C ₃ -C ₁₀ cycloalkyl is C ₃ -C ₁₀ cycloalkyl as defined above, substituted by one or more alkyl groups having up to 8 carbon atoms. A is at least 1 O through C ₁ -C ₈ alkyl, -C ₃ -C ₁₀ cycloalkyl is a O- interposed as defined above which is substituted by one or more groups having carbon atoms of less than 8 alkyl C ₃ - a C ₁₀ cycloalkyl.

C ₁ -C ₁₂ alkoxy is C ₁ -C ₁₂ alkyl substituted by one O-atom. C ₁ -C ₁₂ alkyl has the same meaning as given above for C ₁ -C ₂₀ alkyl to the corresponding number of C-atoms. C ₁ -C ₄ alkoxy is linear or branched and is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butyloxy, sec-butyloxy, isobutyloxy, tert-butyloxy. C ₁ -C ₈ alkoxy and C ₁ -C ₄ alkoxy have the same meaning as above to the corresponding number of C-atoms.

C ₁ -C ₁₂ alkyl sulfanyl is C ₁ -C ₁₂ alkyl substituted by one S-atom. C ₁ -C ₁₂ alkyl has the same meaning as given above for C ₁ -C ₂₀ alkyl to the corresponding number of C-atoms. C ₁ -C ₄ alkylsulfanyl is linear or branched and is, for example, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, sec-butylsulfanyl, Phenyl, < / RTI > tert-butylsulfanyl.

Phenyl-C ₁ -C ₃ alkyl is, for example, benzyl, phenylethyl, α-methylbenzyl or α, α-dimethylbenzyl, especially benzyl.

The phenyl-C ₁ -C ₃ alkoxyl is, for example, benzyloxy, phenylethyloxy, α-methylbenzyloxy or α, α-dimethylbenzyloxy, especially benzyloxy.

C ₂ -C ₁₂ alkenyl radicals are mono- or polyunsaturated and are, for example, C ₂ -C ₁₀ -, C ₂ -C ₈ -, C ₂ -C ₅ -alkenyl such as vinyl, allyl, Allyl, 1,1-dimethylallyl, 1-butenyl, 3-butenyl, 2-butenyl, 1,3-pentadienyl, 5-hexenyl, 7-octenyl or dodecenyl, especially allyl. C ₂ -C ₅ alkenyl radicals have the same meanings as given above for C ₂ -C ₁₂ alkenyl radicals up to the corresponding number of C-atoms.

C ₂ -C ₁₂ alkenyl interrupted by one or more O, CO or NR ₂₆ is interrupted, for example, by O, S, NR ₂₆ or CO 1-9, 1-5, 1-3 or 1 or 2 times . Where more than one intervening radical is present, they may be of the same kind or different. Two O-atoms are separated by one or more methylene groups, preferably two or more methylene groups, i.e., ethylene. The alkenyl group is linear or branched and is defined as above. For example, the following structural units -CH = CH-O-CH ₂ CH ₃ , -CH = CH-OCH = CH _2, etc. may be formed.

C ₄ -C ₈ cycloalkenyl has one or more double bonds, for example C ₄ -C ₆ cycloalkenyl or C ₆ -C ₈ cycloalkenyl. For example, cyclobutenyl, cyclopentenyl, cyclohexenyl or cyclooctenyl, in particular cyclopentenyl and cyclohexenyl, preferably cyclohexenyl.

C ₃ -C ₆ alkenoxy is singly or multiply unsaturated and has the same meaning as said alkenyl having an attached oxy group up to the corresponding number of C-atoms. For example, allyloxy, methallyloxy, butenyloxy, pentenoxy, 1,3-pentadienyloxy, 5-hexenyloxy.

C ₂ -C ₁₂ alkynyl is singly or multiply unsaturated, linear or branched and is, for example, C ₂ -C ₈ -, C ₂ -C ₆ - or C ₂ -C ₄ alkynyl. For example, ethynyl, propynyl, butynyl, 1-butynyl, 3-butynyl, 2-butynyl, pentynyl, hexynyl, 2-hexynyl, 5-hexynyl, octynyl and the like.

C ₂ -C ₂₀ alkanoyl is linear or branched and is, for example, C ₂ -C ₁₈ -, C ₂ -C ₁₄ -, C ₂ -C ₁₂ -, C ₂ -C ₈ -, C ₂ -C ₆ - or C ₂ -C ₄ alkanoyl or C ₄ -C ₁₂ - or C ₄ -C ₈ alkanoyl. Examples are acetyl, propionyl, butanoyl, isobutanoyl, pentanoyl, hexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, dodecanoyl, tetradecanoyl, pentadecanoyl, hexadecanoyl, octano Decanoyl, icosanoyl, preferably acetyl. C ₁ -C ₈ alkanoyl has the same meaning as given above for C ₂ -C ₂₀ alkanoyl up to the corresponding number of C-atoms.

C ₂ -C ₁₂ alkoxycarbonyl is linear or branched and is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, 1,1- Dimethyloxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl or dodecyloxycarbonyl, especially methoxycarbonyl, Ethoxycarbonyl, propoxycarbonyl, n-butyloxycarbonyl or iso-butyloxycarbonyl, preferably methoxycarbonyl.

C ₂ -C ₁₂ alkoxycarbonyl in which one or more O is interrupted is linear or branched. Two O-atoms are separated by at least two methylene groups, i.e., ethylene. The intervening alkoxycarbonyl is unsubstituted or substituted by one or more hydroxyl groups.

C ₆ -C ₂₀ aryloxycarbonyl is, for example, phenyloxycarbonyl [= phenyl-O- (CO) -], naphthyloxycarbonyl, anthryloxycarbonyl and the like.

C ₅ -C ₂₀ heteroaryloxycarbonyl is C ₅ -C ₂₀ heteroaryl-O-CO-.

C ₃ -C ₁₀ cycloalkylcarbonyl is C ₃ -C ₁₀ cycloalkyl-CO-, wherein the cycloalkyl has one of the meanings indicated above to the corresponding number of C-atoms.

C ₃ -C ₁₀ cycloalkylcarbonyl interrupted by one or more O, S, CO, NR ₂₆ refers to intervening cycloalkyl-CO-, wherein the intervening cycloalkyl is defined as described above.

C ₃ -C ₁₀ cycloalkyloxycarbonyl is C ₃ -C ₁₀ cycloalkyl-O- (CO) -, wherein the cycloalkyl has one of the meanings indicated above to the corresponding number of C-atoms.

C ₃ -C ₁₀ cycloalkyloxycarbonyl interrupted by one or more O, S, CO, NR ₂₆ refers to interrupted cycloalkyl-O- (CO) -, wherein the intervening cycloalkyl is optionally substituted as described above Is defined.

C ₁ -C ₂₀ alkylphenyl refers to phenyl substituted by one or more alkyl groups, wherein the sum of the C atoms is 20 or less.

C ₆ -C ₂₀ aryl is, for example, phenyl, naphthyl, anthryl, phenanthryl, pyrene, chrysene, naphthacene, triphenylene etc., especially phenyl or naphthyl, preferably phenyl.

Naphthyl is 1-naphthyl or 2-naphthyl.

In the context of the present invention, C ₃ -C ₂₀ heteroaryl is intended to include a single ring or multi-ring system, such as a fused ring system. For example, thienyl, benzo [b] thienyl, naphtho [2,3-b] thienyl, thianthrenyl, furyl, dibenzofuryl, chromenyl, xanthenyl, thioxanthyl, Pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, pyrrolyl, imidazolyl, pyrrolyl, pyrazinyl, pyrimidinyl, , Phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl,? -Carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl , Phenanthryl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, phenoxazinyl, 7-phenanthryl, anthraquinon-2-yl (= 9,10-dioxo-9,10-dihydroanthracene Benzo [b] thienyl, 2-benzo [b] thienyl, 4-dibenzofuryl, 4,7-dibenzofuryl, 4-methyl Dibenzofuryl, 2-xanthenyl, 8-methyl-2-xanthenyl, 3-xanthenyl, 2-phenoxy 3-pyrrolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-pyrimidinyl, Ethyl-4-imidazolyl, 2-ethyl-5-imidazolyl, 1H-tetrazol-5-yl, 3- pyrazolyl, , 1-propyl-4-pyrazolyl, 2-pyrazinyl, 5,6-dimethyl-2-pyrazinyl, 2-indolizinyl, Indolyl, 1-methyl-3-indolyl, 1,5-dimethyl-2-indolyl, 1-methyl-3-indazolyl, 2,7-dimethyl- Isoquinolyl, 3-methoxy-6-isoquinolyl, 2-methoxy-7-methyl-8-purinyl, Quinolyl, 2-methoxy-6-quinolyl, 6-phthalazinyl, 7-phthalazinyl, 1- Naphthyridin-2-yl, 2-quinoxalinyl, 6-quinoxalinyl, 2,3-dimethyl- 6-quinoxalinyl, 2,3-di Quinazolinyl, 2-quinazolinyl, 7-quinazolinyl, 2-dimethylamino-6-quinazolinyl, 3-cinnolinyl, 6-cinnolinyl, 2-pyrrolidinyl, 2-pyrrolidinyl, 3-carboxy-pyrrolidinyl, 6-pyrrolidinyl, Carbazolyl,? -Carbololin-3-yl, 1-methyl-? -Carbolin-3-yl, 1-methyl-? 3-acridinyl, 2-perimidinyl, 1-methyl-5-perimidinyl, 5-phenanthrolinyl, 6-acridinyl, 2-phenothiazinyl, 3-phenothiazinyl, 10-methyl-3- (4-isothiazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 4-methyl-3-furazanyl, 2-phenoxazinyl, 10-methyl-2-phenoxazinyl and the like.

C ₃ -C ₂₀ heteroaryl is especially thienyl, benzo [b] thienyl, thianthrenyl, thioxanyl, 1-methyl-2-indolyl or 1-methyl-3-indolyl; Especially thienyl.

C ₄ -C ₂₀ heteroarylcarbonyl is a C ₃ -C ₂₀ heteroaryl group as defined above linked to the remainder of the molecule through a CO group.

Substituted aryl radicals phenyl, naphthyl, C ₆ -C ₂₀ aryl or C ₅ -C ₂₀ heteroaryl are each substituted one to seven times, one to six times or one to four times, especially one, two or three times. It is clear that the defined aryl radical can not have more substituents than the free position in the aryl ring.

Substituents on the phenyl ring are preferably present at position 4 on the phenyl ring or in the 3,4-, 3,4,5-, 2,6-, 2,4- or 2,4,6-coordination.

The radicals interposed one or more times are interposed, for example, 1-19, 1-15, 1-12, 1-9, 1-7, 1-5, 1-4, 1-3 or 1 or 2 times The number of atoms depends on the number of C-atoms to be interposed).

Substituted radicals which are substituted more than once are, for example, 1-7, 1-5, 1-4, 1-3, or one or two identical or different substituents.

Radicals substituted by one or more defined substituents are intended to be one substituent of the same or different definition as provided, or have more substituents.

Halogen is fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine, preferably fluorine and chlorine.

When R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , or R ₅ and R ₆ , R ₆ and R ₇ , R ₇ and R ₈ are each independently of one another, -Ii is formed:

또는

와 같은 구조가 바람직하다.

or

Is preferable.

Characterization for the compounds of formula (III) is characterized in that one or more phenyl rings are condensed to the carbazole moiety to form a "naphthyl" ring. This means that one of the above structures is provided as formula (3).

,

와 같은 구조 등이 형성된다.R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ or R ₇ and R ₈ are each independently - (CH ₂ ) _p -Y- (CH ₂ ) _q -, for example,

,

And the like are formed.

The radicals R ₁₇ , R ₁₈ , R ₁₉ and / or R ₂₂ , in which the substituents OR ₁₇ , SR ₁₈ , SOR ₁₈ , SO ₂ R ₁₈ or NR ₁₉ R ₂₀ on the phenyl or naphthyl ring have one of the carbon atoms of the naphthyl ring, _When a 5- or 6-membered ring is formed through ₂₀ , a structure containing three or more rings (including a naphthyl ring) is obtained.

또는

가 위치하는 페닐 또는 나프틸 고리의 탄소 원자 중 1개에 대한 직접 결합을 형성하는 경우에, 예를 들어

,

등과 같은 구조가 형성된다.R ₁₇ is

or

Is to form a direct bond to one of the carbon atoms of the phenyl or naphthyl ring to which it is attached,

,

And the like are formed.

,

,

,

등과 같은 구조가 형성된다. 즉, R₁₆이 SR₁₈ (여기서, 라디칼 R₁₈은 COR₁₆ 기가 부착되어 있는 카르바졸 모이어티의 페닐 또는 나프틸 고리에 대한 직접 결합을 나타낸다.)에 의해 치환된 페닐인 경우에, 카르바졸 모이어티의 페닐 고리 또는 나프틸 고리 중 하나와 함께 티오크산틸 모이어티가 형성된다.R ₁₆ is SR ₁₈ wherein the radical R ₁₈ is COR ₁₆ Represents a direct bond to a phenyl or naphthyl ring of the carbazole moiety to which the group is attached), for example,

,

,

,

And the like are formed. That is, in the case where R ₁₆ is phenyl substituted by SR ₁₈ , wherein the radical R ₁₈ represents a direct bond to a phenyl or naphthyl ring of a carbazole moiety to which the COR ₁₆ group is attached, A thioxanthyl moiety is formed with one of the phenyl ring or the naphthyl ring of the thiophene ring.

R ₁₉ and R ₂₀ together with the N atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring optionally interrupted by O, S or NR ₁₇ , a saturated or unsaturated ring such as an aziridine, Pyrrole, thiazole, pyrrolidine, oxazole, pyridine, 1,3-diazine, 1,2-diazine, piperidine or morpholine.

Preferably R ₁₉ and R ₂₀ together with the N atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring optionally interrupted by O, S or NR ₁₇ , NR < / RTI > ₁₇ , especially a 5- or 6-membered saturated ring with O intervening.

등이 형성된다.When R < ₂₁ > and R < ₂₂ > together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring optionally interrupted by O, S or NR < ₂₆ > and optionally a benzene ring in the saturated or unsaturated ring , Saturated or unsaturated rings such as aziridine, pyrrole, thiazole, pyrrolidine, oxazole, pyridine, 1,3-diazine, 1,2-diazine, piperidine or morpholine, An anelated ring, e.

And so on.

When R ₁₉ and R ₂₀ together with the N-atom to which they are attached form a heteroaromatic ring system, the ring system may contain more than one ring, for example two or three rings, and also one or the same Or heteroatoms of more than one type of different species. Suitable heteroatoms are, for example, N, S, O or P, in particular N, S or O.

For example, carbazole, indole, isoindole, indazole, purine, isoquinoline, quinoline, carbolin or phenothiazine.

In another embodiment of the present invention, the photopolymerization initiator may be included in an amount of 0.1 to 15 parts by weight based on 100 parts by weight of the red photosensitive resin composition. The photopolymerization initiator may be contained in an amount of preferably 0.1 to 10 parts by weight, more preferably 0.5 to 5 parts by weight.

When the photopolymerization initiator is contained within the above range, the red photosensitive resin composition is highly sensitized, and the strength of the pixel portion formed using the red photosensitive resin composition or the smoothness of the surface of the pixel portion tends to be favorable, which is preferable .

If the photopolymerization initiator is contained in the range below the above range, the formation of the pixel portion may be somewhat difficult, and if the photopolymerization initiator is contained in the range exceeding the above range, the smoothness on the surface of the pixel portion may be somewhat lowered.

In another embodiment of the present invention, the red photosensitive resin composition may further include at least one selected from the group consisting of an alkali-soluble binder resin, a photopolymerizable compound, a solvent, and an additive.

Alkali soluble binder resin

The red photosensitive resin composition according to the present invention may contain an alkali-soluble binder resin.

The alkali-soluble binder resin can be produced by copolymerizing an ethylenically unsaturated monomer having a carboxyl group as an essential component in order to have solubility in an alkali developing solution used in a developing process for forming a pattern.

The alkali-soluble binder resin preferably has an acid value of 30 to 150 mgKOH / g in order to ensure compatibility with the dye and storage stability of the red photosensitive resin composition.

When the acid value of the alkali-soluble binder resin is less than 30 mgKOH / g, it is difficult to secure a sufficient developing rate of the red photosensitive resin composition. When the acid value exceeds 150 mgKOH / g, the adhesion with the substrate is decreased, There arises a problem of compatibility and the dye in the blue photosensitive resin composition is precipitated or the storage stability of the red photosensitive resin composition is lowered, and the viscosity tends to rise.

A hydroxyl group may be added to secure further developability of the alkali-soluble binder resin. There is an effect of improving the developing rate for imparting hydroxyl groups, but the sum of the hydroxyl value of the alkali-soluble binder resin and the photopolymerizable compound is limited to 50 mgKOH / g or more and 250 mgKOH / g or less. When the sum of the hydroxyl groups is less than 50 mgKOH / g, a sufficient developing rate can not be secured. When it exceeds 250 mgKOH / g, the dimensional stability of the formed pattern is lowered and the linearity of the pattern becomes poor and the compatibility with the dye is deteriorated A problem of storage stability tends to occur.

Specific examples of the ethylenically unsaturated monomer having a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid and itaconic acid; And anhydrides of these dicarboxylic acids; (meth) acrylates of a polymer having a carboxyl group and a hydroxyl group at both terminals such as? -carboxypolycaprolactone mono (meth) acrylate, and acrylic acid and methacrylic acid are preferable.

In order to impart a hydroxyl group to the alkali-soluble binder resin, an ethylenically unsaturated monomer having a carboxyl group and an ethylenically unsaturated monomer having a hydroxyl group can be copolymerized, and a copolymer of an ethylenically unsaturated monomer having a carboxyl group and a glycidyl group Can be prepared by further reacting the compound. And further by reacting a copolymer of an ethylenically unsaturated monomer having a carboxyl group and an ethylenically unsaturated monomer having a hydroxyl group with a compound having a glycidyl group.

Specific examples of the butylenes unsaturated monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3-phenoxypropyl (meth) acrylate, N-hydroxyethyl acrylamide and the like, and 2-hydroxyethyl (meth) acrylate is preferable, and two or more kinds thereof can be used in combination.

Specific examples of the glycidyl group-containing compounds include butyl glycidyl ether, glycidyl propyl ether, glycidyl phenyl ether, 2-ethylhexyl glycidyl ether, glycidyl butyrate, glycidyl methyl ether, Benzyl glycidyl ether, glycidyl 4-t-butyl benzoate, glycidyl stearate, aryl glycidyl ether, glycidyl methacrylate, glycidyl glycidyl ether, Epoxycyclohexanecarboxylic acid, epoxycyclohexanecarboxylic acid, epoxycyclohexanedicarboxylic acid, epoxycyclohexanedicarboxylic acid, epoxycyclohexanedicarboxylic acid, epoxycyclohexanedicarboxylic acid, epoxycyclohexanone,

The unsaturated monomers copolymerizable in the preparation of the alkali-soluble binder resin are exemplified below, but are not limited thereto.

Specific examples of the polymerizable monomer having an unsaturated bond capable of copolymerization include styrene, vinyltoluene,? -Methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, Aromatic vinyl compounds such as methyl ether, m-vinylbenzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether and p-vinyl benzyl glycidyl ether; N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm N-substituted maleimide-based compounds such as methylphenyl maleimide, Np-methylphenyl maleimide, No-methoxyphenyl maleimide, Nm-methoxyphenyl maleimide and Np-methoxyphenyl maleimide; Propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, alkyl (meth) acrylates such as sec-butyl (meth) acrylate and t-butyl (meth) acrylate; (Meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6] decan- Alicyclic (meth) acrylates such as dicyclopentanyloxyethyl (meth) acrylate and isobornyl (meth) acrylate; Aryl (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate; 3- (methacryloyloxymethyl) -2-trifluoromethyl oxetane, 3- (methacryloyloxymethyl) oxetane, 3- (methacryloyloxymethyl) 2- (methacryloyloxymethyl) oxetane, 2- (methacryloyloxymethyl) -4-trifluoromethyloxetane, and the like Unsaturated oxetane compounds.

These unsaturated monomers may be used alone or in combination of two or more.

The alkali-soluble binder resin may be directly synthesized and used, and commercially available forms may be purchased and used. Commercially available products of the alkali-soluble binder resin include, but are not limited to, SPCY-1L manufactured by Showa Denko K.K.

The content of the alkali-soluble binder resin is such that the sum of the hydroxyl value of the alkali-soluble binder resin and the photopolymerizable compound is in the range of 50 mgKOH / g to 250 mgKOH / g. The content of the alkali- Preferably 5 to 30 parts by weight, more preferably 9 to 20 parts by weight.

When the alkali-soluble binder resin is contained within the above range, the solubility in a developing solution is sufficient, and pattern formation is easy, and reduction in the film thickness of the pixel portion of the exposed portion is prevented at the time of development.

If the alkali-soluble binder resin is contained below the submergence, the non-pixel portion may be somewhat missed, and if the alkali-soluble binder resin is contained in the above range, the solubility in the developer may be somewhat lowered, .

Photopolymerization  compound

The photopolymerizable compound contained in the red photosensitive resin composition of the present invention is a compound capable of polymerizing under the action of light and a photopolymerization initiator described later, and examples thereof include monofunctional monomers, bifunctional monomers, and other polyfunctional monomers.

The type of the monofunctional monomer is not particularly limited, and examples thereof include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate N-vinylpyrrolidone, and the like.

The type of the bifunctional monomer is not particularly limited and examples thereof include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) Glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

The type of the polyfunctional monomer is not particularly limited and includes, for example, trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri Acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (Meth) acrylate, propoxylated dipentaerythritol hexa (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.

Commercially available examples of the photopolymerizable compound include, but are not limited to, A9550 from Shin Nakamura Co., Ltd.

The photopolymerizable compound may be contained in an amount of 1 to 20 parts by weight, preferably 1 to 15 parts by weight, more preferably 3 to 10 parts by weight, based on 100 parts by weight of the entire red photosensitive resin composition. There is a preferable advantage in terms of strength and smoothness of the part.

When the photopolymerizable compound is contained in the range below the above range, the strength of the pixel portion may be somewhat lowered, and when the photopolymerizable compound is contained in the range exceeding the above range, the smoothness may be somewhat lowered. .

solvent

The solvent contained in the red photosensitive resin composition of the present invention is not particularly limited and various organic solvents used in the field of the red photosensitive resin composition can be used.

Specific examples of the solvent include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether and ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, Diethylene glycol dialkyl ethers such as diethylene glycol dipropyl ether and diethylene glycol dibutyl ether; Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate and propylene glycol monopropyl ether acetate; Alkoxyalkyl acetates such as methoxybutyl acetate and methoxypentyl acetate; Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone; alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin; Esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate; and cyclic esters such as? -butyrolactone.

The solvent is preferably an organic solvent having a boiling point of 100 ° C to 200 ° C in the solvent in terms of coating property and drying property, more preferably an alkylene glycol alkyl ether acetate, a ketone, a 3-ethoxypropionic acid Ethyl, and 3-methoxypropionate, and more preferred examples thereof include propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, 3- Methyl propoxypropionate, and the like. These solvents may be used alone or in combination of two or more.

The content of the solvent in the red photosensitive resin composition of the present invention may be 20 to 85 parts by weight, preferably 30 to 80 parts by weight, more preferably 40 to 78 parts by weight, based on 100 parts by weight of the entire red photosensitive resin composition containing the same More preferably, it is included.

When the content of the solvent is within the above range, the coating property can be improved when applied by a coating apparatus such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater) desirable. When the content of the solvent is less than the above range, the coating property may be somewhat lowered, and the process may be somewhat difficult. When the content is above the range, the performance of the color filter formed of the red photosensitive resin composition may be somewhat deteriorated May occur.

The red photosensitive resin composition according to the present invention may further contain other additives such as another polymer compound, a curing agent, a surfactant, an adhesion promoter, an antioxidant, an ultraviolet absorber and an anti-aggregation agent. But it is preferably 0.05 to 1 part by weight, preferably 0.09 to 0.5 part by weight based on 100 parts by weight of the entire red photosensitive resin composition.

For example, the red photosensitive resin composition according to the present invention may further include a silicone leveling agent SH-8400 and the like.

<Color filter>

Another aspect of the present invention relates to a color filter manufactured using the above red photosensitive resin composition.

The color filter includes a substrate and a pattern layer formed on the substrate.

The substrate may be the substrate of the color filter itself, or may be a portion where a color filter is placed on a display device or the like, and is not particularly limited. The substrate may be glass, silicon (Si), silicon oxide (SiOx), or a polymer substrate. The polymer substrate may be polyethersulfone (PES) or polycarbonate (PC).

The pattern layer may be a layer containing the red photosensitive resin composition of the present invention and may be formed by applying the red photosensitive resin composition and exposing, developing and thermally curing the red photosensitive resin composition in a predetermined pattern. The pattern layer may be formed by performing a method commonly known in the art.

The color filter including the substrate and the pattern layer as described above may further include a partition wall formed between each pattern, and may further include a black matrix, but is not limited thereto.

Further, the color filter may further include a protective film formed on the pattern layer of the color filter.

<Image Display Device>

Further, another aspect of the present invention relates to an image display apparatus including the color filter described above.

The color filter of the present invention is applicable not only to a general liquid crystal display device but also to various image display devices such as an electroluminescent display device, a plasma display device, and a field emission display device.

INDUSTRIAL APPLICABILITY The image display device of the present invention has excellent light efficiency, exhibits high luminance, excellent color reproducibility, and can exhibit high contrast.

Hereinafter, the present invention will be described in detail by way of examples to illustrate the present invention. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the above-described embodiments. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art. In the following, "%" and "part" representing the content are by weight unless otherwise specified.

Synthetic example  : Light curing Initiator (C-1) Synthesis

A photopolymerization initiator C-1 was synthesized according to the procedure described in the following steps 1 to 4.

step 1: 13 -(2- Ethylhexyl ) -13H- Dibenzo [a, i] carbazole

13H-dibenzo [a, i] carbazole can be prepared according to the specific procedure, for example, the procedure described in SYNLETT, 2006, 7, 1021.

Sodium hydride (0.19 g; 4.67 mmol) was added to 13H-dibenzo [a, i] carbazole (0.70 g; 3.22 mol) in DMF (3 ml) at 0 ° C. After stirring at 0 ° C for 1 hour, 1-naphthylhydrazine hydrochloride (1.24g; 6.44mmol) was added at 0 ° C and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice water and the crude product was extracted twice with ethyl acetate. The combined organic layers were washed with H ₂ O and brine, dried over magnesium sulfate, concentrated and dried in vacuo to give a yellow liquid as a crude product (1.08 g). The product was used in the subsequent reaction without further purification.

Step 2: (13- (2- Ethylhexyl ) -5- (2,4,6- Trimethylbenzoyl ) -13H- Dibenzo [a, i] carbazole -8-yl] - [4- (2,2,3,3-tetrafluoropropoxy) -phenyl] -methanone

To a solution of 2,4,6-trimethylbenzoyl chloride (27.45 g; 0.1 mmol) at 0 &lt; 0 &gt; C was added to 13- (2-ethylhexyl) -13H- dibenzo [a, i] carbazole (47.16 g; 143.0 mmol) in methylene chloride (400 mL) 150.0mol) and aluminum chloride (20.00g; 150.0mol). After stirring at room temperature for 2 hours, aluminum chloride (22.93 g; 172.0 mol) was added at 0 ° C and 2,4,6-trimethylbenzoyl chloride (23.78 g; 150.0 mol) was added dropwise and the mixture was stirred at room temperature And stirred for 3 hours. The reaction mixture was poured into ice water and the crude product was extracted twice with methylene chloride. The combined organic layers were washed with water and brine, and dried over magnesium sulfate. After addition of 230 ml of n-hexane thereto, the methylene chloride was removed by concentration to obtain a beige solid. This was collected by filtration, washed with n-hexane and then dried to give a beige solid (81.81 g; 95.7%).

Step 3: (13- (2- Ethylhexyl ) -5- (2,4,6- Trimethylbenzoyl ) -13H- Dibenzo [a, i] carbazole -8-yl] - [4- (2,2,3,3-tetrafluoropropoxy) -phenyl] -methanone Oxime  Synthesis of

To a solution of (13- (2-ethylhexyl) -5- (2,4,6-trimethylbenzoyl) -13H-dibenzo [aiJcarbazol-8-yl] - [4- (2 Methoxyethanol (2.28 g; 30.00 mol) and potassium tert-butoxide (1.68 g, 10.0 mmol) were added at room temperature to a solution of 2- (2.08 g; 30.00 mol) was added to the reaction mixture and the mixture was stirred at 100 &lt; 0 &gt; C overnight. The mixture was stirred at room temperature for 3 hours, . After cooling at room temperature, the reaction mixture was poured into 200 ml of water. The precipitated solid was collected by filtration and then washed with methanol to give the title compound as a white solid in 71% yield (4.73 g) Respectively.

Step 4: (13- (2- Ethylhexyl ) -5- (2,4,6- Trimethylbenzoyl ) -13H- Dibenzo [a, i] carbazole -8-yl] - [4- (2,2,3,3-tetrafluoropropoxy) -phenyl] -methanone Oxime  O- Acetate  synthesis

To a solution of (13- (2-ethylhexyl) -5- (2,4,6-trimethylbenzoyl) -13H-dibenzo [aiJcarbazol-8-yl] - [4- (2 (0.78 g, 7.74 mol) and acetyl chloride (0.61 g; 7.74 mol) at 0 ° C were added at 0 ° C to a solution of 3-amino-2- After the reaction was complete, the reaction mixture was added to water, then the crude product was extracted with tert-butyl methyl ether.The organic layer was washed with water and brine, dried over anhydrous &lt; RTI ID = 0.0 &gt; Dried over magnesium sulfate and concentrated to give a residue which was recrystallized from tert-butyl methyl ether to give a white solid (2.00 g; 73%). The product consisted of an isomeric mixture.

Manufacturing example  1. Red pigment liquid composition (D-1)

As the pigment, the C.I. 40 parts by weight of Pigment Red 254 (Cl-DPP), 24 parts by weight (about 10.8 parts by weight in terms of solid content) of BYK2001 (Dispersive: manufactured by BYK, solid content concentration 45.1% by weight) And 136 parts by weight of glycol methyl ether acetate were mixed and dispersed by a bead mill for 12 hours to prepare a red pigment liquid composition (D-1).

Manufacturing example  2. Red pigment liquid composition (D-2)

40 parts by weight of brominated diketopyrrolopyrrole (Br-DPP, Irgaphor 占 Red S 3620 CF from BASF) represented by the following formula 2 as a pigment and 40 parts by weight of BYK2001 (manufactured by BYK) (D-2) was obtained by mixing and dispersing a mixed liquid containing 24 parts by weight (about 10.8 parts by weight in terms of solid content) and 136 parts by weight of propylene glycol methyl ether acetate as a solvent by a bead mill for 12 hours to obtain a red pigment liquid composition ).

Manufacturing example  3. Red pigment liquid composition (D-3)

C.I. 40 parts by weight of Pigment Red 177, 24 parts by weight (about 10.8 parts by weight in terms of solid content) of BYK2001 (manufactured by BYK, solids concentration: 45.1% by weight) as a dispersant and propylene glycol methyl ether acetate 136 Was mixed and dispersed by a bead mill for 12 hours to prepare a red pigment liquid composition (D-3).

Example  And Comparative Example

The red photosensitive resin compositions according to Examples and Comparative Examples were prepared according to the compositions shown in Table 1 below.

division
(Parts by weight) Alkali soluble binder resin Photopolymerizable compound Photopolymerization initiator Red pigment liquid composition additive solvent A B C-1 C-2 C-3 D-1 D-2 D-3 E F Comparative Example 1 10 5 - 0.6 - 20 - 10 0.1 55 Comparative Example 2 10 5 - - 0.6 20 - 10 0.1 55 Comparative Example 3 10 5 - 0.6 - - 20 10 0.1 55 Comparative Example 4 10 5 - - 0.6 - 20 10 0.1 55 Comparative Example 5 10 5 - 0.6 - 4 16 10 0.1 55 Comparative Example 6 10 5 - - 0.6 4 16 10 0.1 55 Comparative Example 7 10 5 - 0.6 - 16 4 10 0.1 55 Comparative Example 8 10 5 - - 0.6 16 4 10 0.1 55 Comparative Example 9 10 5 - 0.6 - 10 10 10 0.1 55 Comparative Example 10 10 5 - - 0.6 10 10 10 0.1 55 Comparative Example 11 10 5 0.6 - - 2 18 10 0.1 55 Comparative Example 12 10 5 0.6 - - 18 2 10 0.1 55 Comparative Example 13 10 5 0.6 - - 20 - 10 0.1 55 Comparative Example 14 10 5 0.6 - - - 20 10 0.1 55 Example 1 10 5 0.6 - - 4 16 10 0.1 55 Example 2 10 5 0.6 - - 16 4 10 0.1 55 Example 3 10 5 0.6 - - 10 10 10 0.1 55 Example 4 10 5 0.6 - - 5 5 20 0.1 55 Example 5 10 5 0.6 - - 8 2 20 0.1 55 Alkali soluble binder resin (A): SPCY-1L (Showa Denko)
Photopolymerizable compound (B): A9550 (Shin Nakamura)
The photopolymerization initiator (C)
C-1: A photopolymerization initiator of Synthesis Example 1
C-2: I-369 (BASF)
C-3: OXE-01 (BASF)
The pigment dispersion (D)
D-1: Red pigment dispersion of Preparation Example 1
D-2: Red pigment dispersion of Preparation Example 2
D-3: Red pigment dispersion of Preparation Example 3
Additive (E): Silicone leveling agent SH-8400 (Dow Corning Toray)
Solvent (F): Propylene glycol monomethyl ether acetate

(1) Manufacture of color filters

The prepared red photosensitive resin composition was applied to the top of the glass substrate by spin coating, and then placed on a heating plate and held at a temperature of 100 캜 for 3 minutes to form a color layer thin film. Then, a test photomask having a line / space pattern of 1 to 50 mu m was placed thereon, and ultraviolet light was irradiated at a distance of 250 mu m from the test photomask. At this time, the ultraviolet light source was irradiated at a light intensity of 50 mJ / cm ² using a 1 kW high pressure mercury lamp containing g, h and i lines, and no special optical filter was used. The color layer thin film irradiated with ultraviolet rays was immersed in a KOH aqueous solution of pH 10.5 for 2 minutes for development. The glass substrate on which the developed color layer thin film was formed was washed with distilled water, dried in a nitrogen gas atmosphere, and heated for 1 hour in a heating oven at 200 ° C to thermally cure the color filter.

(2) Initial chemical resistance evaluation

Using the red photosensitive resin compositions of the examples and comparative examples, one of the coating films on which the pattern was formed in the above-mentioned color filter manufacturing method was subjected to NMP elution evaluation and the other part was evaluated for NMP elution without UV irradiation, , And compared with the lowest measured value in the comparative example.

(%): The lowest measured value in the example, the comparative example / the non-UV irradiated substrate measurement value * 100)

The evaluation criteria are as follows. Initial chemical resistance evaluation results are shown in Table 2 below.

NMP solvent resistance (100 to 150%: ⊚, 150 to 200%: ◯, 200 to 250%: Δ, 250 to 500%: ×) after photo-alignment (UV irradiation)

(3) Photo orientation  Post Chemical Resistance Evaluation

After obtaining two sheets of each of the coated films of the color filter fabrication method using the red photosensitive resin compositions of Examples and Comparative Examples, one sheet was irradiated with UV of 500 mJ / cm ² or more and UV / VIS (UV-2550) And the other part was subjected to NMP elution evaluation without UV irradiation.

The results are shown in Table 2 below.

(%): UV irradiated substrate measurement value / UV not irradiated substrate measurement value * 100)

NMP solvent resistance (100 to 120%: ⊚, 120 to 150%: ◯, 150 to 250%: Δ, 250 to 500%: ×) after optical alignment (UV irradiation)

Evaluation items Initial chemical resistance NMP solvent resistance after photo-alignment (UV) Comparative Example 1 ◎ × Comparative Example 2 ◎ × Comparative Example 3 ○ △ Comparative Example 4 ○ △ Comparative Example 5 ◎ △ Comparative Example 6 ◎ △ Comparative Example 7 ◎ × Comparative Example 8 ◎ × Comparative Example 9 ◎ △ Comparative Example 10 ◎ △ Comparative Example 11 ○ ◎ Comparative Example 12 ◎ △ Comparative Example 13 ◎ △ Comparative Example 14 △ ◎ Example 1 ◎ ◎ Example 2 ◎ ◎ Example 3 ◎ ◎ Example 4 ◎ ◎ Example 5 ◎ ◎

As shown in Table 2, in the case of using the red photosensitive resin composition according to the present invention, color filters having excellent chemical resistance after photo-alignment (UV irradiation) and excellent initial chemical resistance before photo-alignment (UV irradiation) Can be implemented.

In addition, in Examples 1 to 5 using the oxime ester represented by Formula 3 of the present invention, it was confirmed that the characteristics of the NMP content agent were superior to those of Comparative Examples 1 to 10 using the conventional photoinitiator or oxime ester photoinitiator.

Particularly, in Comparative Examples 1, 2, 7 and 8 in which the red pigment was applied in a binary system and a ternary system, a significant difference in the characteristics of the NMP solvent after light alignment (UV irradiation) was largely confirmed. Also, the combination of the oxime ester compounds represented by the formula (3) according to the present invention in the red pigments of Comparative Examples 11 to 14, which were applied in a binary system and a ternary system, also showed poor results. The larger the red pigment ratio to which the compound represented by formula (2) is applied, the lower initial chemical resistance before light alignment (UV irradiation). The larger the red pigment ratio to which the compound represented by formula (1) is applied, As a result of poor chemical properties, CI It was confirmed that the chemical resistance before and after photo-alignment (UV irradiation) was improved between the ratios of the red pigments except for Pigment Red 177 pigment at 2: 8 and 8: 2.

In Examples 1 to 5, various weight ratios (2: 8 to 8: 2) of the photopolymerization initiator containing the oxime ester compound represented by Formula (3), the compound represented by Formula (1) and the compound represented by Formula It was confirmed that the characteristics of NMP content before and after photo-alignment (UV irradiation) were excellent.

Claims (7)

CI Pigment Red 177, a coloring agent comprising a compound represented by the following formula (1) and a compound represented by the following formula (2); And
A photopolymerization initiator comprising a compound represented by the following general formula (3);
Lt; / RTI &gt;
Wherein the compound represented by the following formula (1) and the compound represented by the following formula (2) are contained in a weight ratio of 2: 8 to 8: 2:
[Chemical Formula 1]

(2)

(3)

In Formula 3,
R ₁ to R ₈ are each independently hydrogen, C ₁ -C ₂₀ alkyl,

, COR _16, or NO _2, and;
Provided that at least one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ or R ₇ and R ₈ is

;
R ₉ to R ₁₂ are each independently hydrogen, optionally substituted C ₁ -C ₂₀ alkyl; Or substituted or unsubstituted phenyl;
X is CO or a direct bond;
R ₁₃ is selected from optionally substituted C ₁ -C ₂₀ alkyl, C ₂ -C ₁₂ alkenyl, C ₄ -C ₈ cycloalkenyl, C ₂ -C ₁₂ alkynyl, C ₃ -C ₁₀ cycloalkyl, phenyl or naphthyl (Both of which are optionally substituted);
R ₁₄ is hydrogen, C ₃ -C ₈ cycloalkyl, C ₂ -C ₅ alkenyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₂₀ alkyl, phenyl or naphthyl;
R ₁₅ is C ₆ -C ₂₀ aryl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of phenyl, halogen, C ₁ -C ₄ haloalkyl, CN, NO ₂ , OR ₁₇ , SR _{18, NR 19 R 20, PO} (OC k H 2k + 1) 2, SO-C 1 -C 10 alkyl, SO ₂ -C ₁ -C ₁₀ alkyl by, one or more O, S or NR ₂₆ is interposed a C ₂ -C ₂₀ alkyl substituted by the, or each of which is unsubstituted halogen, or more than _{1 COOR 17, CONR 19 R 20} , phenyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₂₀ heteroaryl Substituted by C ₁ -C ₂₀ alkyl substituted by aryl, C ₆ -C ₂₀ aryloxycarbonyl, C ₃ -C ₂₀ heteroaryloxycarbonyl, OR ₁₇ , SR ₁₈ or NR ₁₉ R ₂₀ ;
R ₁₆ is C ₆ -C ₂₀ aryl unsubstituted or substituted by one or more C ₁ -C ₂₀ alkoxy or C ₁ -C ₂₀ alkyl;
R ₁₇ is C ₁ -C ₄ haloalkyl;
Wherein R ₁₈ is hydrogen, C ₂ -C ₁₂ alkenyl, C ₃ -C ₂₀ cycloalkyl or phenyl-C ₁ -C ₃ alkyl, wherein C ₂ -C ₁₂ alkenyl, C ₃ -C ₂₀ cycloalkyl or phenyl- C ₁ -C ₃ alkyl is interrupted or interrupted by one or more O, S, CO, NR ₂₆ or COOR ₁₇ ;
Or R ₁₈ is unsubstituted or substituted with one or more of OH, SH, CN, C ₃ -C ₆ alkenoxy, OCH ₂ CH ₂ CN, OCH ₂ CH ₂ (CO) O (C ₁ -C ₄ alkyl) _{CO) - (C 2 -C 4} ) alkenyl, O (CO) - (C 1 -C 4 alkyl), O (CO) - phenyl, or (CO) or a C ₁ -C ₂₀ alkyl substituted by oR ₁₇ ;
Or R ₁₈ is C ₂ -C ₂₀ alkyl interrupted by one or more O, S, CO, NR ₂₆ or COOR ₁₇ ;
Or R ₁₈ is (CH ₂ CH ₂ O) _n H, (CH ₂ CH ₂ O) _n (CO) - (C ₁ -C ₈ alkyl), C ₂ -C ₈ alkanoyl or C ₃ -C ₆ alkenoyl ;
Or R ₁₈ is benzoyl which is unsubstituted or substituted by one or more C ₁ -C ₆ alkyl, halogen, OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylsulfanyl;
Or R ₁₈ is phenyl, naphthyl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C ₁ -C ₁₂ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₁₂ alkoxy, CN, NO _2, phenyl, -C ₁ -C ₃ alkyloxy, phenoxy, C ₁ -C ₁₂ alkyl sulfanyl, phenylsulfanyl, N (C ₁ -C ₁₂ alkyl) _2, diphenylamino, (CO ) O (C ₁ -C ₈ alkyl), (CO) -C ₁ -C ₈ alkyl, (CO) N (C ₁ -C ₈ alkyl) ₂ or

Lt; / RTI &gt;
X ₂ is O, CO, S or a direct bond;
R ₁₉ and R ₂₀ are each independently selected from the group consisting of hydrogen, C ₁ -C ₂₀ alkyl, C ₂ -C ₄ hydroxyalkyl, C ₂ -C ₁₀ alkoxyalkyl, C ₂ -C ₅ alkenyl, C ₃ -C ₂₀ cycloalkyl , phenyl, -C ₁ -C ₃ alkyl, C ₁ -C ₈ alkanoyl, C ₁ -C ₈ alkanoyloxy, C ₃ -C ₁₂ alkenyl _{alkanoyl, SO 2 - (C 1 -C} 4 haloalkyl), or benzoyl, or ;
Or R ₁₉ and R ₂₀ are phenyl, naphthyl or C ₃ -C ₂₀ heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₂₀ alkoxy, C ₁ -C ₁₂ alkyl, benzoyl or C ₁ -C _12, or substituted by alkoxy;
Or R ₁₉ and R ₂₀ together with the N-atom to which they are attached form a 5-or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR ₁₇ , membered saturated or unsaturated ring is unsubstituted or substituted, or one or more C ₁ -C ₂₀ alkyl 1, C ₁ -C _{20 alkoxy, = O, oR 17, SR} 18, NR 21 R 22, (CO) R 23, NO 2, halogen, C ₁ -C ₄ - haloalkyl, CN, phenyl,

Or by C ₃ -C ₂₀ cycloalkyl interrupted or interrupted by one or more O, S, CO or NR ₁₇ ;
Or R ₁₉ and R ₂₀ together with the N- atom to which they are attached, unsubstituted or substituted by one or more C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₂₀ alkoxy, = O, OR ₁₇ , SR ₁₈ , NR ₂₁ R ₂₂ , (CO) R ₂₃ ,

Form a heteroaromatic ring system substituted by halogen, NO ₂ , CN, phenyl, or C ₃ -C ₂₀ cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR ₁₇ ;
R ₂₁ and R ₂₂ are each independently hydrogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₁₀ cycloalkyl or phenyl;
Or R ₂₁ and R ₂₂ together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR ₂₆ , The unsubstituted or unsaturated rings are not condensed or the benzene ring is condensed to the 5- or 6-membered saturated or unsaturated ring;
R ₂₃ is hydrogen, OH, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₂₀ alkyl which is non-interrupted or interrupted by at least one O, CO or NR ₂₆ , , S, CO or NR ₂₆ intervening C ₃ -C ₂₀ cycloalkyl, or R ₂₃ is phenyl, naphthyl, phenyl-C ₁ -C ₄ alkyl, OR ₁₇ , SR ₁₈ or NR ₂₁ R ₂₂ ;
R ₂₄ is (CO) OR ₁₇ , CONR ₁₉ R ₂₀ , (CO) R ₁₇ ; Or R ₂₄ has the same meaning as R ₁₉ and R ₂₀ ;
R ₂₅ is COOR ₁₇ , CONR ₁₉ R ₂₀ , (CO) R ₁₇ ; Or R ₂₅ has the same meaning as R ₁₇ ;
R ₂₆ is hydrogen, C ₁ -C ₂₀ alkyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₂₀ alkyl interrupted by one or more O or CO, or phenyl-C ₁ -C ₄ alkyl, Or C ₃ -C ₈ cycloalkyl interrupted by one or more O or CO, or (CO) R ₁₉ , or is phenyl which is unsubstituted or substituted by one or more C ₁ -C ₂₀ alkyl, halogen, C ₁ -C ₄ halo _{alkyl, oR 17, SR 18, NR} 19 R 20 or

Lt; / RTI &gt;;
However, at least one

or

Is present in the molecule. The method according to claim 1,
5 to 70% by weight of the CI Pigment Red 177, 5 to 60% by weight of the compound represented by the formula (1) and 5 to 60% by weight of the compound represented by the formula (2), based on 100% By weight of a red photosensitive resin composition. The method according to claim 1,
An alkali-soluble binder resin, a photopolymerizable compound, a solvent, and an additive. The method according to claim 1,
Based on 100 parts by weight of the entire red photosensitive resin composition,
And the colorant is contained in an amount of 5 to 50 parts by weight. The method according to claim 1,
Based on 100 parts by weight of the entire red photosensitive resin composition,
Wherein the photopolymerization initiator is contained in an amount of 0.1 to 15 parts by weight. A color filter comprising a cured product of the red photosensitive resin composition according to any one of claims 1 to 5. An image display device comprising the color filter of claim 6.