KR20160090168A - Novel compound and polymer - Google Patents

Novel compound and polymer Download PDF

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KR20160090168A
KR20160090168A KR1020150010127A KR20150010127A KR20160090168A KR 20160090168 A KR20160090168 A KR 20160090168A KR 1020150010127 A KR1020150010127 A KR 1020150010127A KR 20150010127 A KR20150010127 A KR 20150010127A KR 20160090168 A KR20160090168 A KR 20160090168A
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KR101788089B1 (en
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박채원
최은정
신명엽
정의수
주범준
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삼성에스디아이 주식회사
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Priority to TW104131519A priority patent/TWI580737B/en
Priority to CN201510649566.1A priority patent/CN105801477B/en
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    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/24Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/30Preparation of azo dyes from other azo compounds by esterification of —COOH or —SO3H groups
    • 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
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/34Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/343Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
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Abstract

Provided are a compound represented by chemical formula 1, and a polymer. In the chemical formula 1, each substituent is defined in the specification. According to an embodiment, the azo-based compound and the polymer comprising the same as a monomer have excellent solubility with respect to an organic solvent, and can be used as a dye during the manufacture of a photosensitive resin composition for a color filter.

Description

신규한 화합물 및 폴리머{NOVEL COMPOUND AND POLYMER}NOVEL COMPOUND AND POLYMER < RTI ID = 0.0 >

본 기재는 신규한 화합물 및 폴리머에 관한 것이다.
The present disclosure relates to novel compounds and polymers.

안료형 감광성 수지 조성물로 제조된 컬러필터에서는 안료 입자 크기에서 비롯되는 휘도와 명암비의 한계가 존재한다. 또한 이미지 센서용 컬러 촬상 소자의 경우에는 미세한 패턴 형성을 위해 더 작은 분산입도를 요구하게 된다. 이와 같은 요구에 부응하고자 안료 대신 입자를 이루지 않는 염료를 도입한 감광성 수지 조성물을 제조하여 휘도와 명암비 등의 색특성이 개선된 컬러필터를 구현하려는 시도가 계속되고 있다.In a color filter made of a pigment type photosensitive resin composition, there is a limit of luminance and contrast ratio resulting from the pigment particle size. Further, in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. In order to meet such a demand, attempts have been made to fabricate a photosensitive resin composition in which a dye that does not form particles is introduced instead of a pigment, thereby realizing a color filter having improved color characteristics such as brightness and contrast ratio.

따라서, 감광성 수지 조성물의 제조에 사용되는 염료로 적합한 단분자 화합물 및 폴리머 화합물에 대한 연구가 필요한 실정이다.
Therefore, there is a need for studies on monomolecular compounds and polymer compounds suitable as dyes used in the production of photosensitive resin compositions.

일 구현예는 신규한 화합물을 제공하기 위한 것이다.One embodiment is to provide a novel compound.

다른 일 구현예는 상기 화합물을 모노머로 포함하는 폴리머를 제공하기 위한 것이다.
Another embodiment is to provide a polymer comprising said compound as a monomer.

본 발명의 일 구현예는 하기 화학식 1로 표시되는 화합물을 제공한다.An embodiment of the present invention provides a compound represented by the following formula (1).

[화학식 1][Chemical Formula 1]

Figure pat00001
Figure pat00001

상기 화학식 1에서,In Formula 1,

R1 및 R2는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, *-C(=O)OR' 또는 *-OC(=O)R' 이고,R 1 and R 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, -C (= O) OR 'or * -OC (= O)

상기 R'은 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C2 내지 C10 알케닐기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,Wherein R 'is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group or a substituted or unsubstituted C6 to C20 aryl group,

단, 상기 R1 및 R2 중 어느 하나는 치환 또는 비치환된 아크릴레이트기를 포함하고,Provided that any one of R 1 and R 2 includes a substituted or unsubstituted acrylate group,

R3은 치환 또는 비치환된 C1 내지 C20 알킬기이다.R 3 is a substituted or unsubstituted C1 to C20 alkyl group.

상기 치환 또는 비치환된 아크릴레이트기는 하기 화학식 2로 표시될 수 있다.The substituted or unsubstituted acrylate group may be represented by the following general formula (2).

[화학식 2](2)

Figure pat00002
Figure pat00002

상기 화학식 2에서,In Formula 2,

R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

상기 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 화학식 6으로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.The compound represented by the formula (1) may be represented by any one selected from the group consisting of the following chemical formulas (3) to (6).

[화학식 3](3)

Figure pat00003
Figure pat00003

[화학식 4][Chemical Formula 4]

Figure pat00004
Figure pat00004

[화학식 5][Chemical Formula 5]

Figure pat00005
Figure pat00005

[화학식 6][Chemical Formula 6]

Figure pat00006
Figure pat00006

상기 화학식 3 내지 화학식 6에서,In the above Chemical Formulas 3 to 6,

L1 내지 L3은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 *-L'-C(=O)O-L"-* 이고,L 1 to L 3 each independently represent a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group or * -L'-C (= O) OL "- *

상기 L' 및 L"은 각각 독립적으로 치환 또는 비치환된 C1 내지 C5 알킬렌기 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,Wherein L 'and L "are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,

R3 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기이고,R 3 and R 5 are each independently a substituted or unsubstituted C 1 to C 20 alkyl group,

R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

상기 화학식 1은 화학식 7 내지 화학식 26으로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.The formula (1) may be represented by any one selected from the group consisting of formulas (7) to (26).

[화학식 7](7)

Figure pat00007
Figure pat00007

[화학식 8][Chemical Formula 8]

Figure pat00008
Figure pat00008

[화학식 9][Chemical Formula 9]

Figure pat00009
Figure pat00009

[화학식 10][Chemical formula 10]

Figure pat00010
Figure pat00010

[화학식 11](11)

Figure pat00011
Figure pat00011

[화학식 12][Chemical Formula 12]

Figure pat00012
Figure pat00012

[화학식 13][Chemical Formula 13]

Figure pat00013
Figure pat00013

[화학식 14][Chemical Formula 14]

Figure pat00014
Figure pat00014

[화학식 15][Chemical Formula 15]

Figure pat00015
Figure pat00015

[화학식 16][Chemical Formula 16]

Figure pat00016
Figure pat00016

[화학식 17][Chemical Formula 17]

Figure pat00017
Figure pat00017

[화학식 18][Chemical Formula 18]

Figure pat00018
Figure pat00018

[화학식 19][Chemical Formula 19]

Figure pat00019
Figure pat00019

[화학식 20][Chemical Formula 20]

Figure pat00020
Figure pat00020

[화학식 21][Chemical Formula 21]

Figure pat00021
Figure pat00021

[화학식 22][Chemical Formula 22]

Figure pat00022
Figure pat00022

[화학식 23](23)

Figure pat00023
Figure pat00023

[화학식 24]≪ EMI ID =

Figure pat00024
Figure pat00024

[화학식 25](25)

Figure pat00025
Figure pat00025

[화학식 26](26)

Figure pat00026
Figure pat00026

상기 화합물은 황색 염료일 수 있다.The compound may be a yellow dye.

상기 황색 염료는 400nm 내지 500nm의 파장범위에서 최대 흡광영역을 가질 수 있다.The yellow dye may have a maximum light absorption region in a wavelength range of 400 nm to 500 nm.

다른 일 구현예는 상기 화학식 1로 표시되는 반복단위를 모노머로 포함하는 폴리머를 제공한다.Another embodiment provides a polymer comprising the repeating unit represented by Formula 1 as a monomer.

즉, 다른 일 구현예는 하기 화학식 27 내지 화학식 30으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나의 반복단위를 포함하는 폴리머를 제공한다.That is, another embodiment provides a polymer comprising any one repeating unit selected from the group consisting of repeating units represented by the following Chemical Formulas 27 to 30.

[화학식 27](27)

Figure pat00027
Figure pat00027

[화학식 28](28)

Figure pat00028
Figure pat00028

[화학식 29][Chemical Formula 29]

Figure pat00029
Figure pat00029

[화학식 30](30)

Figure pat00030
Figure pat00030

상기 화학식 27 내지 화학식 30에서,In the above Chemical Formulas 27 to 30,

L1 내지 L3은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 *-L'-C(=O)O-L"-* 이고,L 1 to L 3 each independently represent a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group or * -L'-C (= O) OL "- *

상기 L' 및 L"은 각각 독립적으로 치환 또는 비치환된 C1 내지 C5 알킬렌기 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,Wherein L 'and L "are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,

R3 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기이고,R 3 and R 5 are each independently a substituted or unsubstituted C 1 to C 20 alkyl group,

R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

상기 폴리머는 하기 화학식 31 및 화학식 32로 표시되는 반복단위를 더 포함할 수 있다.The polymer may further include a repeating unit represented by the following general formula (31) and general formula (32).

[화학식 31](31)

Figure pat00031
Figure pat00031

[화학식 32](32)

Figure pat00032
Figure pat00032

상기 화학식 31 및 화학식 32에서,In the above formulas (31) and (32)

R6는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,R 6 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L4는 치환 또는 비치환된 C1 내지 C10 알킬렌기이다.L 4 is a substituted or unsubstituted C1 to C10 alkylene group.

상기 폴리머는, 폴리머 총량에 대해, 상기 화학식 27 내지 화학식 30으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나의 반복단위 40 중량% 내지 60 중량%; 상기 화학식 31로 표시되는 반복단위 5 중량% 내지 25 중량% 및 상기 화학식 32로 표시되는 반복단위 25 중량% 내지 45 중량%를 포함할 수 있다.40 to 60% by weight of any one of the repeating units selected from the group consisting of the repeating units represented by the above formulas (27) to (30) relative to the total amount of the polymers; 5 to 25% by weight of the repeating unit represented by the formula (31) and 25 to 45% by weight of the repeating unit represented by the formula (32).

상기 폴리머는 하기 화학식 33 내지 화학식 52로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나의 반복단위를 포함할 수 있다.The polymer may include any one repeating unit selected from the group consisting of repeating units represented by the following chemical formulas (33) to (52).

상기 화학식 27로 표시되는 반복단위는 하기 화학식 33 내지 화학식 46으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나일 수 있다.The repeating unit represented by the formula (27) may be any one selected from repeating units represented by the following formulas (33) to (46).

[화학식 33](33)

Figure pat00033
Figure pat00033

[화학식 34](34)

Figure pat00034
Figure pat00034

[화학식 35](35)

Figure pat00035
Figure pat00035

[화학식 36](36)

Figure pat00036
Figure pat00036

[화학식 37](37)

Figure pat00037
Figure pat00037

[화학식 38](38)

Figure pat00038
Figure pat00038

[화학식 39][Chemical Formula 39]

Figure pat00039
Figure pat00039

[화학식 40](40)

Figure pat00040
Figure pat00040

[화학식 41](41)

Figure pat00041
Figure pat00041

[화학식 42](42)

Figure pat00042
Figure pat00042

[화학식 43](43)

Figure pat00043
Figure pat00043

[화학식 44](44)

Figure pat00044
Figure pat00044

[화학식 45][Chemical Formula 45]

Figure pat00045
Figure pat00045

[화학식 46](46)

Figure pat00046
Figure pat00046

상기 화학식 28로 표시되는 반복단위는 하기 화학식 47 또는 화학식 48로 표시되는 반복단위일 수 있다.The repeating unit represented by the formula (28) may be a repeating unit represented by the following formula (47) or (48).

[화학식 47](47)

Figure pat00047
Figure pat00047

[화학식 48](48)

Figure pat00048
Figure pat00048

상기 화학식 29로 표시되는 반복단위는 하기 화학식 49 또는 화학식 50으로 표시되는 반복단위일 수 있다.The repeating unit represented by the formula (29) may be a repeating unit represented by the following formula (49) or (50).

[화학식 49](49)

Figure pat00049
Figure pat00049

[화학식 50](50)

Figure pat00050
Figure pat00050

상기 화학식 30으로 표시되는 반복단위는 하기 화학식 51 또는 화학식 52로 표시되는 반복단위일 수 있다.The repeating unit represented by the formula (30) may be a repeating unit represented by the following formula (51) or (52).

[화학식 51](51)

Figure pat00051
Figure pat00051

[화학식 52](52)

Figure pat00052
Figure pat00052

기타 본 발명의 측면들의 구체적인 사항은 이하의 상세한 설명에 포함되어 있다.
Other aspects of the present invention are included in the following detailed description.

일 구현예에 따른 아조계 화합물 및 이를 모노머로 포함하는 폴리머는 우수한 황색 분광 특성과 높은 몰흡광계수를 가지고 유기 용매에 대한 용해도가 우수하여, 컬러필터용 감광성 수지 조성물 제조 시 염료로 사용될 수 있고, 상기 염료를 포함하는 컬러필터는 우수한 휘도 및 명암비를 가질 수 있다.
The azo compound and the polymer containing the azo compound according to an embodiment have excellent yellow spectral characteristics and a high molar extinction coefficient and are excellent in solubility in an organic solvent and can be used as a dye in the production of a photosensitive resin composition for a color filter, The color filter comprising the dye can have excellent brightness and contrast ratio.

이하, 본 발명의 구현예를 상세히 설명하기로 한다.  다만, 이는 예시로서 제시되는 것으로, 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구범위의 범주에 의해 정의될 뿐이다. Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

본 명세서에서 특별한 언급이 없는 한, "치환" 내지 "치환된"이란, 본 발명의 작용기 중의 하나 이상의 수소 원자가 할로겐 원자(F, Br, Cl 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기(NH2, NH(R200) 또는 N(R201)(R202)이고, 여기서 R200, R201 및 R202는 동일하거나 서로 상이하며, 각각 독립적으로 C1 내지 C10 알킬기임), 아미디노기, 하이드라진기, 하이드라존기, 카르복실기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 지환족 유기기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한다.Means that at least one hydrogen atom of the functional group of the present invention is substituted with a halogen atom (F, Br, Cl or I), a hydroxyl group, a nitro group, a cyano group, an amino group NH 2, NH (R 200), or N (R 201) (R 202), wherein R 200, R 201 and R 202 are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, And a substituted or unsubstituted heterocyclic group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group.

본 명세서에서 특별한 언급이 없는 한, "알킬기"란 C1 내지 C20 알킬기를 의미하고, 구체적으로는 C1 내지 C15 알킬기를 의미하고, "사이클로알킬기"란 C3 내지 C20 사이클로알킬기를 의미하고, 구체적으로는 C3 내지 C18 사이클로알킬기를 의미하고, "알콕시기"란 C1 내지 C20 알콕시기를 의미하고, 구체적으로는 C1 내지 C18 알콕시기를 의미하고, "아릴기"란 C6 내지 C20 아릴기를 의미하고, 구체적으로는 C6 내지 C18 아릴기를 의미하고, "알케닐기"란 C2 내지 C20 알케닐기를 의미하고, 구체적으로는 C2 내지 C18 알케닐기를 의미하고, "알킬렌기"란 C1 내지 C20 알킬렌기를 의미하고, 구체적으로는 C1 내지 C18 알킬렌기를 의미하고, "아릴렌기"란 C6 내지 C20 아릴렌기를 의미하고, 구체적으로는 C6 내지 C16 아릴렌기를 의미한다.Unless otherwise specified in the specification, "alkyl group" means C1 to C20 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C20 cycloalkyl group, specifically C3 Refers to a C1 to C20 alkoxy group, specifically, a C1 to C18 alkoxy group, and an "aryl group" means a C6 to C20 aryl group, specifically, a C6 to C20 aryl group, Refers to a C 2 to C 20 alkenyl group, specifically, a C 2 to C 18 alkenyl group, and the "alkylene group" refers to a C 1 to C 20 alkylene group, specifically, a C1 Refers to a C6 to C20 arylene group, and specifically refers to a C6 to C16 arylene group.

본 명세서에서 특별한 언급이 없는 한, "(메타)아크릴레이트"는 "아크릴레이트"와 "메타크릴레이트" 둘 다 가능함을 의미하며, "(메타)아크릴산"은 "아크릴산"과 "메타크릴산" 둘 다 가능함을 의미한다.(Meth) acrylate "refers to both" acrylic acid "and" methacrylic acid " It means both are possible.

본 명세서에서 별도의 정의가 없는 한, "조합"이란 혼합 또는 공중합을 의미한다. 또한 "공중합"이란 블록 공중합 내지 랜덤 공중합을 의미하고, "공중합체"란 블록 공중합체 내지 랜덤 공중합체를 의미한다.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.

본 명세서 내 화학식에서 별도의 정의가 없는 한, 화학 결합이 그려져야 하는 위치에 화학결합이 그려져 있지 않은 경우는 상기 위치에 수소 원자가 결합되어 있음을 의미한다.Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.

본 명세서에서 별도의 정의가 없는 한, "*"는 동일하거나 상이한 원자 또는 화학식과 연결되는 부분을 의미한다.Unless otherwise defined herein, "*" means the same or different atom or moiety connected to a formula.

또한, 본 명세서에서 별도의 정의가 없는 한, "최대 흡광영역"이란 최대 흡광도를 나타내는 영역(범위)을 의미한다.
Further, unless otherwise defined in this specification, the "maximum light absorbing region" means a region (range) showing the maximum absorbance.

일 구현예는 하기 화학식 1로 표시되는 화합물을 제공한다.An embodiment provides a compound represented by the following formula (1).

[화학식 1][Chemical Formula 1]

Figure pat00053
Figure pat00053

상기 화학식 1에서,In Formula 1,

R1 및 R2는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, *-C(=O)OR' 또는 *-OC(=O)R' 이고,R 1 and R 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, -C (= O) OR 'or * -OC (= O)

상기 R'은 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C2 내지 C10 알케닐기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,Wherein R 'is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group or a substituted or unsubstituted C6 to C20 aryl group,

단, 상기 R1 및 R2 중 어느 하나는 치환 또는 비치환된 아크릴레이트기를 포함하고,Provided that any one of R 1 and R 2 includes a substituted or unsubstituted acrylate group,

R3은 치환 또는 비치환된 C1 내지 C20 알킬기이다.R 3 is a substituted or unsubstituted C1 to C20 alkyl group.

상기 화학식 1로 표시되는 화합물은 아조계 화합물로, 우수한 황색 분광 특성과 높은 몰흡광계수를 가지며, 유기용매에 대해 용해도 또한 우수하다. 나아가, 상기 화학식 1로 표시되는 화합물의 치환기인 R1 및 R2 중 어느 하나는 반드시 치환 또는 비치환된 아크릴레이트기를 포함하기 때문에, 상기 화학식 1로 표시되는 화합물의 내열성, 내화학성 및 컬러필터 제조 시의 공정성이 우수해진다.The compound represented by Formula 1 is an azo compound having excellent yellow spectral characteristics and a high molar absorptivity, and has excellent solubility in an organic solvent. Further, since any one of R 1 and R 2 which are substituents of the compound represented by Formula 1 includes a substituted or unsubstituted acrylate group, the heat resistance, chemical resistance, and color filter production The fairness of the city is excellent.

상기 치환 또는 비치환된 아크릴레이트기는 하기 화학식 2로 표시될 수 있다.The substituted or unsubstituted acrylate group may be represented by the following general formula (2).

[화학식 2](2)

Figure pat00054
Figure pat00054

상기 화학식 2에서,In Formula 2,

R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

상기 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 화학식 6으로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.The compound represented by the formula (1) may be represented by any one selected from the group consisting of the following chemical formulas (3) to (6).

[화학식 3](3)

Figure pat00055
Figure pat00055

[화학식 4][Chemical Formula 4]

Figure pat00056
Figure pat00056

[화학식 5][Chemical Formula 5]

Figure pat00057
Figure pat00057

[화학식 6][Chemical Formula 6]

Figure pat00058
Figure pat00058

상기 화학식 3 내지 화학식 6에서,In the above Chemical Formulas 3 to 6,

L1 내지 L3은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 *-L'-C(=O)O-L"-* 이고,L 1 to L 3 each independently represent a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group or * -L'-C (= O) OL "- *

상기 L' 및 L"은 각각 독립적으로 치환 또는 비치환된 C1 내지 C5 알킬렌기 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,Wherein L 'and L "are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,

R3 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기이고,R 3 and R 5 are each independently a substituted or unsubstituted C 1 to C 20 alkyl group,

R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

예컨대, 상기 화학식 1, 구체적으로 상기 화학식 3은 화학식 7 내지 화학식 20으로 이루어진 군에서 선택된 어느 하나로 표시될 수 있으나, 이에 한정되는 것은 아니다.For example, the compound represented by Formula 1, specifically Formula 3, may be represented by any one selected from the group consisting of Formulas 7 to 20, but is not limited thereto.

[화학식 7](7)

Figure pat00059
Figure pat00059

[화학식 8][Chemical Formula 8]

Figure pat00060
Figure pat00060

[화학식 9][Chemical Formula 9]

Figure pat00061
Figure pat00061

[화학식 10][Chemical formula 10]

Figure pat00062
Figure pat00062

[화학식 11](11)

Figure pat00063
Figure pat00063

[화학식 12][Chemical Formula 12]

Figure pat00064
Figure pat00064

[화학식 13][Chemical Formula 13]

Figure pat00065
Figure pat00065

[화학식 14][Chemical Formula 14]

Figure pat00066
Figure pat00066

[화학식 15][Chemical Formula 15]

Figure pat00067
Figure pat00067

[화학식 16][Chemical Formula 16]

Figure pat00068
Figure pat00068

[화학식 17][Chemical Formula 17]

Figure pat00069
Figure pat00069

[화학식 18][Chemical Formula 18]

Figure pat00070
Figure pat00070

[화학식 19][Chemical Formula 19]

Figure pat00071
Figure pat00071

[화학식 20][Chemical Formula 20]

Figure pat00072
Figure pat00072

예컨대, 상기 화학식 1, 구체적으로 상기 화학식 4는 화학식 21 또는 화학식 22로 표시될 수 있으나, 이에 한정되는 것은 아니다.For example, Formula 1, specifically Formula 4, may be represented by Formula 21 or Formula 22, but is not limited thereto.

[화학식 21][Chemical Formula 21]

Figure pat00073
Figure pat00073

[화학식 22][Chemical Formula 22]

Figure pat00074
Figure pat00074

예컨대, 상기 화학식 1, 구체적으로 상기 화학식 5는 화학식 23 또는 화학식 24로 표시될 수 있으나, 이에 한정되는 것은 아니다.For example, Formula 1, specifically Formula 5, may be represented by Formula 23 or Formula 24, but is not limited thereto.

[화학식 23](23)

Figure pat00075
Figure pat00075

[화학식 24]≪ EMI ID =

Figure pat00076
Figure pat00076

예컨대, 상기 화학식 1, 구체적으로 상기 화학식 6은 화학식 25 또는 화학식 26으로 표시될 수 있으나, 이에 한정되는 것은 아니다.For example, Formula 1, specifically Formula 6, may be represented by Formula 25 or Formula 26, but is not limited thereto.

[화학식 25](25)

Figure pat00077
Figure pat00077

[화학식 26](26)

Figure pat00078
Figure pat00078

일 구현예에 따른 화합물은 특정 치환기에 아크릴레이트기를 포함하는 아조계 화합물로서, 적은 양으로도 보다 선명한 색의 발현이 가능하여, 착색제로 사용 시 휘도나 명암비 등의 색특성이 우수한 디스플레이 소자의 제조가 가능하다. 예컨대, 상기 화합물은 착색제, 예컨대 염료, 예컨대 황색 염료, 예컨대 400nm 내지 500nm의 파장범위, 예컨대 410nm 내지 450nm의 파장범위에서 최대 흡광영역을 가지는 염료일 수 있다.The compound according to one embodiment is an azo compound including an acrylate group in a specific substituent, and can display a clearer color even in a small amount. Thus, when used as a colorant, the manufacture of a display device having excellent color characteristics such as luminance and contrast ratio Is possible. For example, the compound may be a colorant such as a dye, such as a yellow dye, for example a dye having a maximum absorption range in the wavelength range of 400 nm to 500 nm, for example in the wavelength range of 410 nm to 450 nm.

예컨대, 상기 화합물은 400nm 내지 500nm의 파장범위, 예컨대 410nm 내지 450nm의 파장범위에서 최대 흡광도를 나타내는 염료일 수 있다.For example, the compound may be a dye exhibiting the maximum absorbance in a wavelength range of 400 nm to 500 nm, for example, a wavelength range of 410 nm to 450 nm.

일반적으로, 염료는 컬러필터 내에 사용되는 구성성분 중 가장 고가의 구성성분이다. 그러므로, 원하는 효과, 예컨대 고휘도나 고명암비 등을 달성하기 위해서는 고가의 염료를 더 많이 사용해야 하기 때문에 생산 단가가 상승할 수 밖에 없었다. 그러나, 일 구현예에 따른 화합물을 컬러필터 내 염료로 사용하는 경우, 적은 양으로도 고휘도, 고명암비 등의 우수한 색특성을 달성할 수 있어 생산 단가의 절감이 가능하다.In general, dyes are the most expensive component of the components used in color filters. Therefore, in order to achieve a desired effect, for example, a high luminance and a high contrast ratio, it is necessary to use more expensive dye, so that the production cost has to be increased. However, when the compound according to one embodiment is used as a dye in a color filter, excellent color characteristics such as high luminance and high contrast ratio can be achieved even in a small amount, and production cost can be reduced.

다른 일 구현예에 따르면, 상기 일 구현예에 따른 화합물을 모노머로 포함하는 폴리머를 제공한다.According to another embodiment, there is provided a polymer comprising a compound according to one embodiment as a monomer.

즉, 상기 폴리머는 하기 화학식 1로 표시되는 화합물을 모노머로 포함한다. That is, the polymer includes a compound represented by the following formula (1) as a monomer.

[화학식 1][Chemical Formula 1]

Figure pat00079
Figure pat00079

상기 화학식 1에서,In Formula 1,

R1 및 R2는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, *-C(=O)OR' 또는 *-OC(=O)R' 이고,R 1 and R 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, -C (= O) OR 'or * -OC (= O)

상기 R'은 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C2 내지 C10 알케닐기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,Wherein R 'is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group or a substituted or unsubstituted C6 to C20 aryl group,

단, 상기 R1 및 R2 중 어느 하나는 하기 화학식 2로 표시되는 치환기를 포함하고,Provided that any one of R 1 and R 2 includes a substituent represented by the following formula (2)

[화학식 2](2)

Figure pat00080
Figure pat00080

(상기 화학식 2에서,(In the formula (2)

R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다)R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group)

R3은 치환 또는 비치환된 C1 내지 C20 알킬기이다.R 3 is a substituted or unsubstituted C1 to C20 alkyl group.

상기 폴리머는 10,000 g/mol 내지 100,000 g/mol의 중량평균 분자량을 가질 수 있다.The polymer may have a weight average molecular weight of from 10,000 g / mol to 100,000 g / mol.

예컨대, 상기 화학식 1로 표시되는 모노머는 상기 폴리머 내에서 하기 화학식 27 내지 화학식 30으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나의 반복단위로 표시될 수 있다. 즉, 상기 폴리머는 하기 화학식 27 내지 화학식 30으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나의 반복단위를 포함할 수 있다.For example, the monomer represented by the formula (1) may be represented by any one of repeating units represented by the following formulas (27) to (30) in the polymer. That is, the polymer may include any one repeating unit selected from the group consisting of repeating units represented by the following formulas (27) to (30).

[화학식 27](27)

Figure pat00081
Figure pat00081

[화학식 28](28)

Figure pat00082
Figure pat00082

[화학식 29][Chemical Formula 29]

Figure pat00083
Figure pat00083

[화학식 30](30)

Figure pat00084
Figure pat00084

상기 화학식 27 내지 화학식 30에서,In the above Chemical Formulas 27 to 30,

L1 내지 L3은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 *-L'-C(=O)O-L"-* 이고,L 1 to L 3 each independently represent a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group or * -L'-C (= O) OL "- *

상기 L' 및 L"은 각각 독립적으로 치환 또는 비치환된 C1 내지 C5 알킬렌기 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,Wherein L 'and L "are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,

R3 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기이고,R 3 and R 5 are each independently a substituted or unsubstituted C 1 to C 20 alkyl group,

R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

상기 폴리머는 하기 화학식 31 및 화학식 32로 표시되는 반복단위를 더 포함할 수 있다.The polymer may further include a repeating unit represented by the following general formula (31) and general formula (32).

[화학식 31](31)

Figure pat00085
Figure pat00085

[화학식 32](32)

Figure pat00086
Figure pat00086

상기 화학식 31 및 화학식 32에서,In the above formulas (31) and (32)

R6는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,R 6 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L4는 치환 또는 비치환된 C1 내지 C10 알킬렌기이다.L 4 is a substituted or unsubstituted C1 to C10 alkylene group.

상기 폴리머는, 상기 화학식 27 내지 화학식 30으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나의 반복단위 40 중량% 내지 60 중량%; 상기 화학식 31로 표시되는 반복단위 5 중량% 내지 25 중량% 및 상기 화학식 32로 표시되는 반복단위 25 중량% 내지 45 중량%를 포함할 수 있다. 상기 폴리머가 상기 중량범위로 각각의 반복단위를 포함하는 경우, 용해도가 부여되고 구조적인 안정성에 유리한 효과가 있다.The polymer may include 40 wt% to 60 wt% of any one repeating unit selected from the group consisting of repeating units represented by the above formulas (27) to (30); 5 to 25% by weight of the repeating unit represented by the formula (31) and 25 to 45% by weight of the repeating unit represented by the formula (32). When the polymer contains each repeating unit in the above weight range, solubility is imparted and it is advantageous in structural stability.

예컨대, 상기 화학식 27로 표시되는 반복단위는 하기 화학식 33 내지 화학식 46으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나일 수 있다.For example, the repeating unit represented by the formula (27) may be any one selected from repeating units represented by the following formulas (33) to (46).

[화학식 33](33)

Figure pat00087
Figure pat00087

[화학식 34](34)

Figure pat00088
Figure pat00088

[화학식 35](35)

Figure pat00089
Figure pat00089

[화학식 36](36)

Figure pat00090
Figure pat00090

[화학식 37](37)

Figure pat00091
Figure pat00091

[화학식 38](38)

Figure pat00092
Figure pat00092

[화학식 39][Chemical Formula 39]

Figure pat00093
Figure pat00093

[화학식 40](40)

Figure pat00094
Figure pat00094

[화학식 41](41)

Figure pat00095
Figure pat00095

[화학식 42](42)

Figure pat00096
Figure pat00096

[화학식 43](43)

Figure pat00097
Figure pat00097

[화학식 44](44)

Figure pat00098
Figure pat00098

[화학식 45][Chemical Formula 45]

Figure pat00099
Figure pat00099

[화학식 46](46)

Figure pat00100
Figure pat00100

상기 화학식 28로 표시되는 반복단위는 하기 화학식 47 또는 화학식 48로 표시되는 반복단위일 수 있다.The repeating unit represented by the formula (28) may be a repeating unit represented by the following formula (47) or (48).

[화학식 47](47)

Figure pat00101
Figure pat00101

[화학식 48](48)

Figure pat00102
Figure pat00102

상기 화학식 29로 표시되는 반복단위는 하기 화학식 49 또는 화학식 50으로 표시되는 반복단위일 수 있다.The repeating unit represented by the formula (29) may be a repeating unit represented by the following formula (49) or (50).

[화학식 49](49)

Figure pat00103
Figure pat00103

[화학식 50](50)

Figure pat00104
Figure pat00104

상기 화학식 30으로 표시되는 반복단위는 하기 화학식 51 또는 화학식 52로 표시되는 반복단위일 수 있다.The repeating unit represented by the formula (30) may be a repeating unit represented by the following formula (51) or (52).

[화학식 51](51)

Figure pat00105
Figure pat00105

[화학식 52](52)

Figure pat00106
Figure pat00106

상기 화합물 및/또는 폴리머는 컬러필터용 감광성 수지 조성물 내 착색제로써 사용될 수 있다. The compound and / or the polymer may be used as a coloring agent in a photosensitive resin composition for a color filter.

상기 컬러필터 내 패턴 형성 공정은 다음과 같다.The pattern forming process in the color filter is as follows.

상기 감광성 수지 조성물을 지지 기판상에 스핀 코팅, 슬릿 코팅, 잉크젯 프린팅 등으로 도포하는 공정; 상기 도포된 감광성 수지 조성물을 건조하여 감광성 수지 조성물 막을 형성하는 공정; 상기 감광성 수지 조성물 막을 노광하는 공정; 상기 노광된 감광성 수지 조성물 막을 알칼리 수용액으로 현상하여 감광성 수지막을 제조하는 공정; 및 상기 감광성 수지막을 가열 처리하는 공정을 포함한다. 상기 공정 상의 조건 등에 대하여는 당해 분야에서 널리 알려진 사항이므로, 본 명세서에서 자세한 설명은 생략하기로 한다.
Applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to produce a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The process conditions and the like are well known in the art, and therefore, detailed description thereof will be omitted herein.

이하, 실시예를 들어 본 발명에 대해서 더욱 상세하게 설명할 것이나, 하기의 실시예는 본 발명의 바람직한 실시예일 뿐 본 발명이 하기 실시예에 한정되는 것은 아니다.
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.

(화합물의 합성)(Synthesis of Compound)

합성예Synthetic example 1: 화학식 7로 표시되는 화합물의 합성 1: Synthesis of compound represented by formula (7)

Figure pat00107
Figure pat00107

Figure pat00108
Figure pat00108

125mL 삼각 플라스크에 3.12g의 4-aminobenzoic acid, 75.6ml의 DI water, 17.28ml의 HCl (35%)를 icebath 하에서 stirring 한다. 14.4ml의 sodium nitrite 수용액(1mM)을 dropwise 해준 후 icebath 하에서 3시간 동안 stirring 해준다. In a 125 mL Erlenmeyer flask, 3.12 g of 4-aminobenzoic acid, 75.6 mL of DI water, and 17.28 mL of HCl (35%) are stirred under icebath. Dropwise 14.4 ml of sodium nitrite solution (1 mM) and stir for 3 hours under icebath.

4.35g의 ethyl cyanoacetate, 4.97g의 ethylhexylamine을 넣고 110℃에서 2시간 동안 reflux 반응을 보낸다. 5g의 ethylaetoacetate, 3.76g의 piperidine을 넣고 reflux 하에 overnight 반응을 보낸다.4.35 g of ethyl cyanoacetate and 4.97 g of ethylhexylamine are added and the reaction is refluxed at 110 ° C. for 2 hours. 5 g of ethylaetoacetate and 3.76 g of piperidine are added, and overnight reaction is carried out under reflux.

TLC 확인 후 산으로 워컵(work-up) 및 물로 여러번 워싱해서 피리돈 화합물 (1)을 합성한다.After confirming TLC, the pyridone compound (1) is synthesized by washing with acid several times with work-up and water.

4.722g의 피리돈 화합물 (1)을 20ml의 DI water에 넣어준 후, NaOH 수용액을 첨가하며 녹여준다(pH8). 녹아있는 피리돈 화합물 (1)을 4-aminobenzoic acid가 포함된 상기 125ml 삼각 플라스크에 첨가한 후 sodium carbonate (10%)수용액으로 pH를 중성으로 맞춘다. 물로 필터 정제 후 진공 건조하여 화합물 (2)를 만든다.4.722 g of the pyridone compound (1) are dissolved in 20 ml of DI water, followed by addition of an aqueous solution of NaOH (pH 8). The dissolved pyridone compound (1) is added to the 125 ml Erlenmeyer flask containing 4-aminobenzoic acid, and the pH is adjusted to neutral with an aqueous solution of sodium carbonate (10%). After filtration with water, the residue is vacuum dried to give compound (2).

5.5g의 화합물 (2)를 250ml 플라스크에 넣고 2.09g의 GMA, 2.16g의 TBAB, 70ml의 acetonitrile 을 첨가한 후 90℃에서 reflux 하에 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 7(CF 7)로 표시되는 화합물을 합성한다.5.5 g of the compound (2) is placed in a 250 ml flask, 2.09 g of GMA, 2.16 g of TBAB and 70 ml of acetonitrile are added, followed by an overnignt reaction at 90 ° C under reflux. After work-up with MC / water, column purification is carried out to synthesize a compound represented by formula (CF 7).

1H NMR(DMSO) : 15.02(s, 1H), 8.1(m, 1H), 7.94(m, 1H), 7.73(m, 1H), 7.55(m, 1H), 6.65(m, 1H), 6.17(m, 1H), 4.7(m, 1H), 4.3(m, 2H), 3.9(m, 2H), 2.03(s, 1H) 1.73(m, 3H), 1.96(m, 3H), 1.81(m, 1H), 1.28(m, 8H), 0.91(m, 6H)
1 H NMR (DMSO): 15.02 (s, IH), 8.1 (m, IH), 7.94 (m, IH), 7.73 (m, 3H), 1.96 (m, 3H), 1.81 (m, 2H) , 1 H), 1.28 (m, 8 H), 0.91 (m, 6 H)

합성예Synthetic example 2: 화학식 8로 표시되는 화합물의 합성 2: Synthesis of Compound Represented by Formula 8

Figure pat00109
Figure pat00109

Figure pat00110
Figure pat00110

125mL 삼각 플라스크에 3.12g의 4-aminobenzoic acid, 75.6ml의 DI water, 17.28ml의 HCl (35%)를 icebath 하에서 stirring 한다. 14.4ml의 sodium nitrite 수용액(1mM)을 dropwise 해준 후 icebath 하에서 3시간 동안 stirring 해준다. 상기 합성예 1에서 ehtylhexylamine 대신 butylamine으로 대체하여 피리돈 화합물 (3)을 합성한다. 3.69g의 피리돈 (3)을 20ml의 DI water에 넣어준 후, NaOH 수용액을 첨가하며 녹여준다(pH8). 녹아있는 피리돈 화합물 (3)을 4-aminobenzoic acid가 포함된 상기 125ml 삼각 플라스크에 첨가한 후 sodium carbonate (10%)수용액으로 pH를 중성으로 맞춘다. 물로 필터 정제 후 진공 건조하여 화합물 (4)를 만든다.In a 125 mL Erlenmeyer flask, 3.12 g of 4-aminobenzoic acid, 75.6 mL of DI water, and 17.28 mL of HCl (35%) are stirred under icebath. Dropwise 14.4 ml of sodium nitrite solution (1 mM) and stir for 3 hours under icebath. The pyridone compound (3) is synthesized by substituting butylamine for ehtylhexylamine in Synthesis Example 1 above. 3.69 g of pyridone (3) is added to 20 ml of DI water, and then an aqueous NaOH solution is added to dissolve it (pH 8). Add the dissolved pyridone compound (3) to the 125 ml Erlenmeyer flask containing 4-aminobenzoic acid and neutralize the pH with an aqueous solution of sodium carbonate (10%). After filtration with water, the residue is vacuum dried to give compound (4).

4.8g의 화합물 (4)를 250ml 플라스크에 넣고 2.09g의 GMA, 2.16g의 TBAB, 70ml의 acetonitrile 을 첨가한 후 90℃에서 reflux 하에 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 8로 표시되는 화합물을 합성한다.4.8 g of compound (4) are placed in a 250 ml flask, 2.09 g of GMA, 2.16 g of TBAB, and 70 ml of acetonitrile are added, followed by an overnignt reaction at 90 ° C under reflux. After work-up with MC / water, column purification is carried out to synthesize the compound represented by the formula (8).

1H NMR(DMSO) 15.02(s, 1H), 8.1(m, 1H), 7.94(m, 1H), 7.73(m, 1H), 7.55(m, 1H), 6.65(m, 1H), 6.17(m, 1H), 4.7(m, 1H), 4.3(m, 2H), 3.9(m, 2H), 2.03(s, 1H) 1.73(m, 3H), 1.96(m, 3H), 1.28(m, 4H), 0.9(m, 3H)
1 H NMR (DMSO) 15.02 (s, IH), 8.1 (m, IH), 7.94 (m, IH), 7.73 (m, IH), 7.55 (m, 3H), 1.96 (m, 3H), 1.28 (m, 2H) 4H), 0.9 (m, 3H)

합성예Synthetic example 3: 화학식 9로 표시되는 화합물의 합성 3: Synthesis of Compound Represented by Formula 9

Figure pat00111
Figure pat00111

Figure pat00112
Figure pat00112

125mL 삼각 플라스크에 3.12g의 3-aminobenzoic acid, 75.6ml의 DI water, 17.28ml의 HCl (35%)를 icebath 하에서 stirring 한다. 14.4ml의 sodium nitrite 수용액 (1mM)을 dropwise 해준 후 icebath 하에서 3시간 동안 stirring 해준다. 4.722g의 피리돈 화합물 (1)을 20ml의 DI water에 넣어준 후, NaOH 수용액을 첨가하며 녹여준다(pH8). 녹아있는 피리돈 화합물 (1)을 3-aminobenzoic acid가 포함된 상기 125ml 삼각 플라스크에 첨가한 후 sodium carbonate (10%)수용액으로 pH를 중성으로 맞춘다. 물로 필터 정제 후 진공 건조하여 화합물 (5)를 만든다.In a 125 mL Erlenmeyer flask, 3.12 g of 3-aminobenzoic acid, 75.6 mL of DI water, and 17.28 mL of HCl (35%) are stirred under icebath. Dropwise 14.4 ml of sodium nitrite solution (1 mM) and stir for 3 hours under icebath. 4.722 g of the pyridone compound (1) are dissolved in 20 ml of DI water, followed by addition of an aqueous solution of NaOH (pH 8). The dissolved pyridone compound (1) is added to the 125 ml Erlenmeyer flask containing 3-aminobenzoic acid, and the pH is adjusted to neutral with an aqueous solution of sodium carbonate (10%). After filtration with water, the residue is vacuum dried to give compound (5).

5.5g의 화합물 (5)를 250ml 플라스크에 넣고 2.09g의 GMA, 2.16g의 TBAB, 70ml의 acetonitrile을 첨가한 후 90℃에서 reflux 하에 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 9로 표시되는 화합물을 합성한다.5.5 g of compound (5) are placed in a 250 ml flask, 2.09 g of GMA, 2.16 g of TBAB and 70 ml of acetonitrile are added, and the overnignt reaction is carried out at 90 ° C under reflux. After work-up with MC / water, column purification is carried out to synthesize the compound represented by the formula (9).

GC-MS(DI) m/z: 552.26
GC-MS (DI) m / z: 552.26

합성예Synthetic example 4: 화학식 10으로 표시되는 화합물의 합성 4: Synthesis of Compound Represented by Formula 10

Figure pat00113
Figure pat00113

Figure pat00114
Figure pat00114

125mL 삼각 플라스크에 3.12g의 3-aminobenzoic acid, 75.6ml의 DI water, 17.28ml의 HCl (35%)를 icebath 하에서 stirring 한다. 14.4ml의 sodium nitrite 수용액 (1mM)을 dropwise 해준 후 icebath 하에서 3시간 동안 stirring 해준다. 3.69g 의 피리돈 화합물 (3)을 20ml의 DI water에 넣어준 후, NaOH 수용액을 첨가하며 녹여준다(pH8). 녹아있는 피리돈 화합물 (3)을 3-aminobenzoic acid가 포함된 상기 125ml 삼각 플라스크에 첨가한 후 sodium carbonate (10%)수용액으로 pH를 중성으로 맞춘다. 물로 필터 정제 후 진공 건조하여 화합물 (6)을 만든다.In a 125 mL Erlenmeyer flask, 3.12 g of 3-aminobenzoic acid, 75.6 mL of DI water, and 17.28 mL of HCl (35%) are stirred under icebath. Dropwise 14.4 ml of sodium nitrite solution (1 mM) and stir for 3 hours under icebath. 3.69 g of the pyridone compound (3) are dissolved in 20 ml of DI water, followed by addition of an aqueous solution of NaOH (pH 8). The dissolved pyridone compound (3) is added to the 125 ml Erlenmeyer flask containing 3-aminobenzoic acid, and the pH is adjusted to neutral with an aqueous solution of sodium carbonate (10%). After filtration with water, the residue is vacuum dried to give compound (6).

4.8g의 화합물 (6)을 250ml 플라스크에 넣고 2.09g의 GMA, 2.16g의 TBAB, 70ml의 acetonitrile 을 첨가한 후 90℃에서 reflux 하에 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 10으로 표시되는 화합물을 합성한다.4.8 g of compound (6) are placed in a 250 ml flask, 2.09 g of GMA, 2.16 g of TBAB, and 70 ml of acetonitrile are added, followed by an overnignt reaction at 90 ° C under reflux. After work-up with MC / water, column purification is performed to synthesize a compound represented by formula (10).

GC-MS(DI) m/z: 494.22
GC-MS (DI) m / z: 494.22

합성예Synthetic example 5: 화학식 25로 표시되는 화합물의 합성 5: Synthesis of Compound Represented by Chemical Formula 25

Figure pat00115
Figure pat00115

Figure pat00116
Figure pat00116

20mL vial에 1.5g의 isobutyl 4-aminobenzoate, 32ml의 DI water, 7.5ml의 HCl (35%)를 icebath 하에서 stirring 한다. 6ml의 sodium nitrite 수용액 (1mM)을 dropwise 해준 후 icebath 하에서 3시간 동안 stirring 해준다. 1.46g의 피리돈 화합물 (7)을 20ml의 DI water에 넣어준 후, NaOH 수용액을 첨가하며 녹여준다(pH8). 녹아있는 피리돈 화합물 (7)을 isobutyl 4-aminobenzoate가 포함된 상기 20mL vial에 첨가한 후 sodium carbonate (10%)수용액으로 pH를 중성으로 맞춘다. 물로 필터 정제 후 진공 건조하여 화합물 (8)를 만든다.To a 20 mL vial is added 1.5 g of isobutyl 4-aminobenzoate, 32 mL of DI water, and 7.5 mL of HCl (35%) under icebath. After dropwise adding 6 ml of sodium nitrite solution (1 mM), stir for 3 hours under icebath. 1.46 g of the pyridone compound (7) is dissolved in 20 ml of DI water, followed by addition of an aqueous solution of NaOH (pH 8). Add the dissolved pyridone compound (7) to the 20 mL vial containing isobutyl 4-aminobenzoate and neutralize the pH with an aqueous solution of sodium carbonate (10%). After purification by filtration with water, it is vacuum dried to give compound (8).

1g의 화합물 (8)를 100ml 플라스크에 넣고 0.766g의 TEA, 0.154g의 DMAP, 0.457g의 acryloyl chloride, 10ml의 acetonitrile 을 첨가한 후 RT에서 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 25로 표시되는 화합물을 합성한다.1 g of compound (8) is placed in a 100 ml flask, 0.766 g of TEA, 0.154 g of DMAP, 0.457 g of acryloyl chloride, and 10 ml of acetonitrile are added, followed by an overnignt reaction at RT. After work-up with MC / water, column purification is carried out to synthesize the compound represented by formula (25).

1H NMR(DMSO) : 14.38(s, 1H), 8.03(m, 1H), 7.85(m, 1H), 7.8(m, 1H), 7.6(m, 1H), 6.5(m, 1H), 6.26(m, 1H), 5.94(m, 1H), 4.4(m, 2H), 4.1(m, 2H), 3.9(s, 2H), 2.64(m, 1H), 2.01(s, 1H), 1.73(m, 3H), 1.21(m, 6H)
1 H NMR (DMSO): 14.38 (s, IH), 8.03 (m, IH), 7.85 (m, IH), 7.8 (m, 1H), 5.94 (m, 1H), 4.4 (m, 2H), 4.1 (m, 2H), 3.9 m, 3H), 1.21 (m, 6H)

합성예Synthetic example 6: 화학식 26으로 표시되는 화합물의 합성 6: Synthesis of the compound represented by the formula (26)

상기 합성예 5에서 acryloyl chloride 대신 methacryloyl chloride를 사용한 것을 제외하고는 합성예 5와 동일하게 하여, 화학식 26으로 표시되는 화합물(GC-MS(DI) m/z: 466.19)을 합성한다.
(GC-MS (DI) m / z: 466.19) was synthesized in the same manner as in Synthesis Example 5, except that methacryloyl chloride was used instead of acryloyl chloride in Synthesis Example 5.

합성예Synthetic example 7: 화학식 11로 표시되는 화합물의 합성 7: Synthesis of Compound Represented by Formula 11

상기 합성예 1에서, 4-aminobenzoic acid 대신 2-aminobenzoic acid를 사용한 것을 제외하고는 합성예 1과 동일하게 하여, 화학식 11로 표시되는 화합물(GC-MS(DI) m/z: 552.26)을 합성한다.
(GC-MS (DI) m / z: 552.26) was synthesized in the same manner as in Synthesis Example 1, except that 2-aminobenzoic acid was used instead of 4-aminobenzoic acid in Synthesis Example 1 do.

합성예Synthetic example 8: 화학식 12로 표시되는 화합물의 합성 8: Synthesis of Compound Represented by Formula 12

상기 합성예 1에서, ehtylhexylamine 대신 isopropylamine을 사용한 것을 제외하고는 합성예 1과 동일하게 하여, 화학식 12로 표시되는 화합물(GC-MS(DI) m/z: 480.20)을 합성한다.
(GC-MS (DI) m / z: 480.20) was synthesized in the same manner as in Synthesis Example 1, except that isopropylamine was used instead of ehtylhexylamine in Synthesis Example 1. [

합성예Synthetic example 9: 화학식 13으로 표시되는 화합물의 합성 9: Synthesis of Compound Represented by Formula 13

상기 합성예 1에서, ehtylhexylamine 대신 isobutylamine을 사용한 것을 제외하고는 합성예 1과 동일하게 하여, 화학식 13으로 표시되는 화합물(GC-MS(DI) m/z: 494.22)을 합성한다.
(GC-MS (DI) m / z: 494.22) was synthesized in the same manner as in Synthesis Example 1, except that isobutylamine was used instead of ehtylhexylamine in Synthesis Example 1.

합성예Synthetic example 10: 화학식 14로 표시되는 화합물의 합성 10: Synthesis of Compound Represented by Formula 14

상기 합성예 1에서, ehtylhexylamine 대신 isoamylamine을 사용한 것을 제외하고는 합성예 1과 동일하게 하여, 화학식 14로 표시되는 화합물(GC-MS(DI) m/z: 508.23)을 합성한다.
(GC-MS (DI) m / z: 508.23) was synthesized in the same manner as in Synthesis Example 1, except that isoamylamine was used instead of ehtylhexylamine in Synthesis Example 1.

합성예Synthetic example 11: 화학식 15로 표시되는 화합물의 합성 11: Synthesis of compound represented by formula (15)

상기 합성예 1과 동일한 방법으로 화합물 (2)를 합성한다. 이 후, 동일한 당량의 화합물 (2)와 1,4-dihydroxybenzene, 1.5 당량의 DCC를 THF 용매 하에 RT로 반응시킨다. TLC로 반응을 체크하고, EA/물로 워컵(work-up)한 후 칼럼 정제한다. 만들어진 화합물에 상기 합성예 5와 같이 TEA, DMAP, acryloyl chloride, acetonitrile을 첨가한 후 RT에서 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 15로 표시되는 화합물(GC-MS(DI) m/z: 556.23)을 합성한다.
Compound (2) is synthesized in the same manner as Synthesis Example 1. Subsequently, the same equivalent amount of compound (2) and 1,4-dihydroxybenzene, 1.5 equivalent of DCC are reacted with RT under a THF solvent. The reaction is checked by TLC, work-up with EA / water and column refined. TEA, DMAP, acryloyl chloride, and acetonitrile were added to the prepared compound as in Synthesis Example 5, and an overnignt reaction was performed at RT. (GC-MS (DI) m / z: 556.23) represented by the following formula (15).

합성예Synthetic example 12: 화학식 16으로 표시되는 화합물의 합성 12: Synthesis of the compound represented by the formula (16)

상기 합성예 11에서 acryloyl chloride 대신 methacryloyl chloride를 사용한 것을 제외하고는 합성예 11과 동일하게 하여, 화학식 16으로 표시되는 화합물(GC-MS(DI) m/z: 570.24)을 합성한다.
(GC-MS (DI) m / z: 570.24) was synthesized in the same manner as in Synthesis Example 11, except that methacryloyl chloride was used instead of acryloyl chloride in Synthesis Example 11.

합성예Synthetic example 13: 화학식 21로 표시되는 화합물의 합성 13: Synthesis of Compound Represented by Formula 21

상기 합성예 1에서의 4-aminobenzoic acid 대신 3-aminophenol을 사용한 것을 제외하고는 합성예 1과 동일한 방법으로 azo coupling 반응을 진행한다. 만들어진 화합물에 상기 합성예 5와 같이 TEA, DMAP, acryloyl chloride, acetonitrile을 첨가한 후 RT에서 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 21로 표시되는 화합물(GC-MS(DI) m/z: 436.21)을 합성한다.
The azo coupling reaction was carried out in the same manner as in Synthesis Example 1 except that 3-aminophenol was used in place of 4-aminobenzoic acid in Synthesis Example 1. [ TEA, DMAP, acryloyl chloride, and acetonitrile were added to the prepared compound as in Synthesis Example 5, and an overnignt reaction was performed at RT. After work-up with MC / water, the product was purified by column to synthesize the compound represented by Chemical Formula 21 (GC-MS (DI) m / z: 436.21).

합성예Synthetic example 14: 화학식 22로 표시되는 화합물의 합성 14: Synthesis of Compound Represented by Formula 22

상기 합성예 13에서 acryloyl chloride 대신 methacryloyl chloride를 사용한 것을 제외하고는 합성예 13과 동일하게 하여, 화학식 22로 표시되는 화합물(GC-MS(DI) m/z: 450.23)을 합성한다.
(GC-MS (DI) m / z: 450.23) was synthesized in the same manner as in Synthesis Example 13, except that methacryloyl chloride was used instead of acryloyl chloride in Synthesis Example 13.

합성예Synthetic example 15: 화학식 23으로 표시되는 화합물의 합성 15: Synthesis of compound represented by formula (23)

상기 합성예 1에서의 4-aminobenzoic acid 대신 3-aminophenol을 사용한 것을 제외하고는 합성예 1과 동일한 방법으로 azo coupling 반응을 진행한다. 만들어진 아조계 화합물과 동일한 당량의 4-hydroxybenzoic acid, 1.5 당량의 DCC를 THF 용매 하에 RT로 반응하여 esterification을 진행한다. TLC로 반응을 체크하고, EA/물로 워컵(work-up)한 후 칼럼 정제한다. 만들어진 화합물에 상기 합성예 5와 같이 TEA, DMAP, acryloyl chloride, acetonitrile 을 첨가한 후 RT에서 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 23으로 표시되는 화합물(GC-MS(DI) m/z: 556.23)을 합성하였다.
The azo coupling reaction was carried out in the same manner as in Synthesis Example 1 except that 3-aminophenol was used in place of 4-aminobenzoic acid in Synthesis Example 1. [ 4 equivalents of 4-hydroxybenzoic acid and 1.5 equivalents of DCC are reacted with RT in THF solvent to effect esterification. The reaction is checked by TLC, work-up with EA / water and column refined. TEA, DMAP, acryloyl chloride, and acetonitrile were added to the prepared compound as in Synthesis Example 5, and an overnignt reaction was performed at RT. After work-up with MC / water, the product was purified by column to synthesize a compound represented by the formula (23) (GC-MS (DI) m / z: 556.23).

합성예Synthetic example 16: 화학식 24로 표시되는 화합물의 합성 16: Synthesis of the compound represented by the formula (24)

상기 합성예 15에서 acryloyl chloride 대신 methacryloyl chloride를 사용한 것을 제외하고는 합성예 15와 동일하게 하여, 화학식 24로 표시되는 화합물(GC-MS(DI) m/z: 570.25)을 합성한다.
(GC-MS (DI) m / z: 570.25) was synthesized in the same manner as in Synthesis Example 15, except that methacryloyl chloride was used instead of acryloyl chloride in Synthesis Example 15.

합성예Synthetic example 17: 화학식 17로 표시되는 화합물의 합성 17: Synthesis of Compound Represented by Formula 17

상기 합성예 1과 동일한 방법으로 화합물 (2)를 합성한다. 이 후, 동일한 당량의 화합물 (2)와 ethylene glycol, 1.5 당량의 DCC를 THF 용매 하에 RT로 반응한다. TLC로 반응을 체크하고, EA/물로 워컵(work-up)한 후 칼럼 정제한다. 만들어진 화합물에 상기 합성예 5와 같이 TEA, DMAP, acryloyl chloride, acetonitrile 을 첨가한 후 RT에서 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 17로 표시되는 화합물(GC-MS(DI) m/z: 508.23)을 합성하였다.
Compound (2) is synthesized in the same manner as Synthesis Example 1. Subsequently, the same equivalent amount of compound (2) and ethylene glycol, 1.5 equivalents of DCC are reacted in a THF solvent at RT. The reaction is checked by TLC, work-up with EA / water and column refined. TEA, DMAP, acryloyl chloride, and acetonitrile were added to the prepared compound as in Synthesis Example 5, and an overnignt reaction was performed at RT. After work-up with MC / water, the product was purified by column to synthesize the compound represented by Chemical formula 17 (GC-MS (DI) m / z: 508.23).

합성예Synthetic example 18: 화학식 18로 표시되는 화합물의 합성 18: Synthesis of Compound Represented by Formula 18

상기 합성예 17에서 acryloyl chloride 대신 methacryloyl chloride를 사용한 것을 제외하고는 합성예 17과 동일하게 하여, 화학식 18로 표시되는 화합물(GC-MS(DI) m/z: 522.25)을 합성한다.
(GC-MS (DI) m / z: 522.25) was synthesized in the same manner as in Synthesis Example 17, except that methacryloyl chloride was used instead of acryloyl chloride in Synthesis Example 17.

합성예Synthetic example 19: 화학식 19로 표시되는 화합물의 합성 19: Synthesis of Compound Represented by Formula 19

상기 합성예 1과 동일한 방법으로 화합물 (2)를 합성한다. 이 후, 동일한 당량의 화합물 (2)와 4-hydroxybenzoic acid, 1.5 당량의 DCC를 THF 용매 하에 RT로 반응하여 esterification 한다. TLC로 반응을 체크하고, EA/물로 워컵(work-up)한 후 칼럼 정제한다. 만들어진 화합물에 상기 합성예 1과 같이 GMA, TBAB, acetonitrile 을 첨가한 후 90℃에서 reflux 하에 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 19로 표시되는 화합물(GC-MS(DI) m/z: 610.26)을 합성하였다.
Compound (2) is synthesized in the same manner as Synthesis Example 1. Subsequently, the same equivalent amount of compound (2) and 4-hydroxybenzoic acid, 1.5 equivalents of DCC are reacted with RT in THF solvent to effect esterification. The reaction is checked by TLC, work-up with EA / water and column refined. GMA, TBAB, and acetonitrile were added to the resulting compound as in Synthesis Example 1, and an overnignt reaction was conducted under reflux at 90 ° C. After work-up with MC / water, column purification was performed to synthesize the compound represented by formula 19 (GC-MS (DI) m / z: 610.26).

합성예Synthetic example 20: 화학식 20으로 표시되는 화합물의 합성 20: Synthesis of compound represented by formula (20)

상기 합성예 1과 동일한 방법으로 화합물 (2)를 합성한다. 이 후, 동일한 당량의 화합물 (2)와 4-glycolic acid, 1.5 당량의 DCC를 THF 용매 하에 RT로 반응하여 esterification 한다. TLC로 반응을 체크하고, EA/물로 워컵(work-up)한 후 칼럼 정제한다. 만들어진 화합물에 상기 합성예 1과 같이 GMA, TBAB, acetonitrile 을 첨가한 후 90℃에서 reflux 하에 overnignt 반응을 보낸다. MC/물로 워컵(work-up)한 후, 칼럼 정제하여 화학식 20으로 표시되는 화합물(GC-MS(DI) m/z: 658.26)을 합성하였다.
Compound (2) is synthesized in the same manner as Synthesis Example 1. Then, the same equivalent amount of compound (2) and 4-glycolic acid, 1.5 equivalents of DCC are reacted with RT under a THF solvent to effect esterification. The reaction is checked by TLC, work-up with EA / water and column refined. GMA, TBAB, and acetonitrile were added to the resulting compound as in Synthesis Example 1, and an overnignt reaction was conducted under reflux at 90 ° C. After work-up with MC / water, the product was purified by column to synthesize a compound represented by Chemical Formula 20 (GC-MS (DI) m / z: 658.26).

합성예Synthetic example 21: 화학식 33으로 표시되는 반복단위를 포함하는  21: A polymer comprising repeating units represented by the formula (33) 폴리머의Of polymer 합성 synthesis

합성예 1의 화학식 7로 표시되는 화합물 50 중량%, 메타크릴산(대정화금製) 15 중량% 및 벤질 메타크릴레이트(Hitach社) 35 중량%를 각각 모노머로 포함하는 폴리머를 합성한다.A polymer containing 50% by weight of the compound represented by the general formula (7) in Synthetic Example 1, 15% by weight of methacrylic acid (made by purified gold) and 35% by weight of benzylmethacrylate (Hitach) as monomers is synthesized.

구체적으로, 100ml 비커에 개시제인 V601(Wako 社)을 1.5g 첨가한 뒤, 모노머의 총합 30g을 기준으로 하여 합성예 1의 화학식 7로 표시되는 화합물 50 중량%, 메타크릴산(대정화금製) 15 중량% 및 벤질메타크릴레이트(Hitach社) 35 중량% 비율로 차례로 첨가하였다. 용매인 CYCLOHEXANONE을 72g 추가로 첨가하고 염료단량체 및 개시제가 완전히 녹을 때까지 30분간 교반하여 모노머 용액을 제조하였다. 중합반응을 진행하기 위해 냉각기가 부착된 250ml 유리 반응기에 용매 54g을 투입한 뒤 85℃까지 승온한 후, 앞서 제조된 모노머 용액을 3시간 동안 반응기에 적하 하였다. 적하 완료 후 동일 온도에서 9시간 동안 반응을 진행 한 뒤, 온도를 상온으로 낮추고 반응을 종결하였다. 상기 중합 반응은 질소분위기 하에서 진행하였다. Waters社의 겔투과 크로마토그래피(Gel Permission Chromatography; GPC)를 이용하여 측정한 중량평균분자량은 10,800 g/mol 이었다.
Specifically, 1.5 g of V601 (Wako) as an initiator was added to a 100 ml beaker, and then 50% by weight of the compound represented by the general formula (7) in Synthesis Example 1, 50% by weight of methacrylic acid ) And benzyl methacrylate (Hitach) at a ratio of 35% by weight. 72 g of CYCLOHEXANONE as a solvent was further added and stirred for 30 minutes until the dye monomer and the initiator were completely dissolved to prepare a monomer solution. To proceed the polymerization reaction, 54 g of a solvent was added to a 250 ml glass reactor equipped with a condenser, and the temperature was raised to 85 ° C., and the monomer solution prepared above was added dropwise to the reactor for 3 hours. After completion of the dropwise addition, the reaction was carried out at the same temperature for 9 hours, the temperature was lowered to room temperature and the reaction was terminated. The polymerization reaction was carried out in a nitrogen atmosphere. The weight average molecular weight measured by Gel Permeation Chromatography (GPC) of Waters was 10,800 g / mol.

합성예Synthetic example 22: 화학식 35로 표시되는 반복단위를 포함하는  22: a polymer comprising repeating units represented by the general formula (35) 폴리머의Of polymer 합성 synthesis

합성예 21에서 화학식 7로 표시되는 화합물 50 중량% 대신, 화학식 9로 표시되는 화합물 50 중량%를 사용한 것을 제외하고는 합성예 21과 동일하게 하여 화학식 35로 표시되는 반복단위를 포함하는 폴리머를 합성하였다. Waters社의 겔투과 크로마토그래피(Gel Permission Chromatography: GPC)를 이용하여 측정한 중량평균분자량은 9,300 g/mol 이었다.
The procedure of Synthesis Example 21 was repeated except that 50% by weight of the compound represented by the formula (9) was used instead of 50% by weight of the compound represented by the formula (7) to synthesize a polymer containing the repeating unit represented by the formula Respectively. The weight average molecular weight measured by Gel Permeation Chromatography (GPC) of Waters was 9,300 g / mol.

합성예Synthetic example 23: 화학식 47로 표시되는 반복단위를 포함하는  23: A polymer comprising a repeating unit represented by the formula (47) 폴리머의Of polymer 합성 synthesis

합성예 21에서 화학식 7로 표시되는 화합물 50 중량% 대신, 화학식 21로 표시되는 화합물 50 중량%를 사용한 것을 제외하고는 합성예 21과 동일하게 하여 화학식 47로 표시되는 반복단위를 포함하는 폴리머를 합성하였다. Waters社의 겔투과 크로마토그래피(Gel Permission Chromatography: GPC)를 이용하여 측정한 중량평균분자량은 9,700 g/mol 이었다.
The procedure of Synthesis Example 21 was repeated except that 50% by weight of the compound represented by the formula (21) was used instead of 50% by weight of the compound represented by the formula (7) to synthesize a polymer containing the repeating unit represented by the formula Respectively. The weight average molecular weight measured by Gel Permeation Chromatography (GPC) of Waters was 9,700 g / mol.

합성예Synthetic example 24: 화학식 49로 표시되는 반복단위를 포함하는  24: A polymer comprising repeating units represented by the formula (49) 폴리머의Of polymer 합성 synthesis

합성예 21에서 화학식 7로 표시되는 화합물 50 중량% 대신, 화학식 23으로 표시되는 화합물 50 중량%를 사용한 것을 제외하고는 합성예 21과 동일하게 하여 화학식 49로 표시되는 반복단위를 포함하는 폴리머를 합성하였다. Waters社의 겔투과 크로마토그래피(Gel Permission Chromatography: GPC)를 이용하여 측정한 중량평균분자량은 10,100 g/mol 이었다.
The procedure of Synthesis Example 21 was repeated except that 50% by weight of the compound represented by the formula (23) was used instead of 50% by weight of the compound represented by the formula (7) to synthesize a polymer containing the repeating unit represented by the formula Respectively. The weight average molecular weight measured by Gel Permeation Chromatography (GPC) of Waters Co. was 10,100 g / mol.

합성예Synthetic example 25: 화학식 52로 표시되는 반복단위를 포함하는  25: A polymer comprising repeating units represented by the formula (52) 폴리머의Of polymer 합성 synthesis

합성예 21에서 화학식 7로 표시되는 화합물 50 중량% 대신, 화학식 26으로 표시되는 화합물 50 중량%를 사용한 것을 제외하고는 합성예 21과 동일하게 하여 화학식 52로 표시되는 반복단위를 포함하는 폴리머를 합성하였다. Waters社의 겔투과 크로마토그래피(Gel Permission Chromatography: GPC)를 이용하여 측정한 중량평균분자량은 9,900 g/mol 이었다.
The procedure of Synthesis Example 21 was repeated except that 50% by weight of the compound represented by the formula (26) was used instead of 50% by weight of the compound represented by the formula (7) to synthesize a polymer containing the repeating unit represented by the formula Respectively. The weight average molecular weight measured by Gel Permeation Chromatography (GPC) of Waters was 9,900 g / mol.

비교 compare 합성예Synthetic example 1 One

환류 냉각기와 교반기를 장착한 10ℓ의 중합 반응기에 사이클로헥사논(Shiny社) 1000g을 80℃로 가열한 후, 위에서 제조된 화합물(12) 300g, 벤질 메타크릴레이트(Hitach社) 300g, 메타크릴산(대정화금製) 106g 및 2,2'-아조비스아이소부티로니트릴(wako社) 92g을 사이클로헥사논(Shiny社) 5000g에 녹인 용액을 가열된 중합 반응기에 3시간 동안 서서히 투입하였다.  투입 완료 후 14시간 동안 교반하여 하기 화학식 B로 표시되는 반복단위를 포함하는 폴리머를 얻었다.  Waters社의 겔투과 크로마토그래피(Gel Permission Chromatography: GPC)를 이용하여 측정한 중량평균분자량은 9,800 g/mol 이었다. 1000 g of cyclohexanone (Shiny) was heated to 80 占 폚, and then 300 g of the compound (12) prepared above, 300 g of benzyl methacrylate (Hitach), 300 g of methacrylic acid (Manufactured by Daikin Industries, Ltd.) and 92 g of 2,2'-azobisisobutyronitrile (wako) in 5000 g of cyclohexanone (Shiny) was slowly added to the heated polymerization reactor for 3 hours. After completion of the addition, the mixture was stirred for 14 hours to obtain a polymer containing a repeating unit represented by the following formula (B). The weight average molecular weight measured by Gel Permeation Chromatography (GPC) of Waters was 9,800 g / mol.

[화학식 B][Chemical Formula B]

Figure pat00117
Figure pat00117

(상기 화학식 B에서, a=2, b=2 및 c=1 이다.)
(In the above formula B, a = 2, b = 2 and c = 1).

평가 1: 용해도 측정Evaluation 1: Measurement of solubility

합성예 1 내지 합성예 20의 화합물 및 화학식 A로 표시되는 화합물 0.5 g에, 희석 용제(PGMEA)를 각각 첨가하고, 해당 용액을 믹스 로터(iuchi 주식회사제 MIXROTAR VMR-5)로 25℃, 100 rpm으로 1시간 동안 교반한 후, 화합물의 용해 상태(용해된 화합물 함량)를 확인한 결과를 하기 표 1에 나타내었다.
A diluting solvent (PGMEA) was added to 0.5 g of each of the compounds of Synthesis Examples 1 to 20 and the compound represented by the formula (A), and the solution was mixed with a mix rotor (MIXROTAR VMR-5 manufactured by iuchi Co., , And the dissolution state (content of dissolved compound) of the compound was confirmed. The results are shown in Table 1 below.

화합물compound 용해도 평가Solubility assessment 화학식 7Formula 7 화학식 9Formula 9 화학식 11Formula 11 화학식 14Formula 14 화학식 15Formula 15 화학식 16Formula 16 화학식 21Formula 21 화학식 22Formula 22 화학식 23Formula 23 화학식 2424 화학식 17Formula 17 화학식 1818 화학식 19Formula 19 화학식 2020 화학식 AA X

(화학식 A의 구조는 다음과 같다.(The structure of the formula (A) is as follows.

[화학식 A](A)

Figure pat00118
)
Figure pat00118
)

용해도 평가 기준Solubility evaluation criteria

≥20wt% in PGMEA : ○≥20wt% in PGMEA: ○

<20wt% in PGMEA: Ⅹ<20wt% in PGMEA: X

상기 표 1로부터, 일 구현예에 따른 화합물은 유기 용매에 대한 용해도가 우수하여, 이를 염료로 포함하는 감광성 수지 조성물은 상기 화합물을 포함하지 않는 감광성 수지 조성물보다 우수한 색특성을 나타낼 것임을 용이하게 예측할 수 있다.
From Table 1, it can be easily predicted that the compound according to one embodiment has excellent solubility in an organic solvent, and that the photosensitive resin composition containing the compound as a dye will exhibit color characteristics superior to the photosensitive resin composition not containing the compound have.

(감광성 수지 조성물 합성)(Synthesis of photosensitive resin composition)

실시예Example 1 One

하기 표 2에 기재된 조성으로, 용매에 광중합 개시제를 용해시킨 후 2시간 동안 상온에서 교반하였다. 여기에, 바인더 수지, 광중합성 단량체를 첨가하고, 2시간 동안 상온에서 교반하였다. 여기에, 합성예 21의 화합물을 첨가한 후, 1시간 동안 상온에서 교반하고, 실란계 커플링제를 첨가하고 1시간 동안 상온에서 교반하였다. 상기 용액에 대하여 3회에 걸친 여과를 행하여 불순물을 제거하여 실시예 1에 따른 감광성 수지 조성물을 제조하였다.
The photopolymerization initiator was dissolved in a solvent as shown in Table 2 below, and then stirred at room temperature for 2 hours. To this, a binder resin and a photopolymerizable monomer were added, and the mixture was stirred at room temperature for 2 hours. After the addition of the compound of Synthesis Example 21, the mixture was stirred at room temperature for 1 hour, added with a silane-based coupling agent, and stirred at room temperature for 1 hour. The solution was filtered three times to remove impurities to prepare the photosensitive resin composition of Example 1.

(단위: g)(Unit: g) 성분ingredient 함량content 바인더 수지Binder resin 아크릴계 바인더 수지 (BX-04, 일본촉매社)Acrylic binder resin (BX-04, manufactured by Nippon Shokubai Co., Ltd.) 33 광중합성 단량체Photopolymerizable monomer 디펜타에리트리톨헥사아크릴레이트 (일본촉매社)Dipentaerythritol hexaacrylate (Nippon Catalyst Co., Ltd.) 77 광중합개시제Photopolymerization initiator OXE01 (BASF社)OXE01 (BASF) 1One 착색제coloring agent 합성예 21의 화합물The compound of Synthesis Example 21 55 용매menstruum PGMEAPGMEA 83.983.9 기타 첨가제Other additives γ-글리시독시 프로필 트리메톡시실란 (S-510, Chisso社)γ-glycidoxypropyltrimethoxysilane (S-510, Chisso) 0.10.1

실시예Example 2 2

합성예 21의 화합물 대신 합성예 22의 화합물을 사용한 것을 제외하고는, 실시예 1과 동일하게 하여 실시예 2에 따른 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition according to Example 2 was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 22 was used instead of the compound of Synthesis Example 21.

실시예Example 3 3

합성예 21의 화합물 대신 합성예 23의 화합물을 사용한 것을 제외하고는, 실시예 1과 동일하게 하여 실시예 3에 따른 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition according to Example 3 was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 23 was used instead of the compound of Synthesis Example 21.

실시예Example 4 4

합성예 21의 화합물 대신 합성예 24의 화합물을 사용한 것을 제외하고는, 실시예 1과 동일하게 하여 실시예 4에 따른 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition according to Example 4 was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 24 was used in place of the compound of Synthesis Example 21.

실시예Example 5 5

합성예 21의 화합물 대신 합성예 25의 폴리머를 사용한 것을 제외하고는, 실시예 1과 동일하게 하여 실시예 5에 따른 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition according to Example 5 was prepared in the same manner as in Example 1, except that the polymer of Synthesis Example 25 was used in place of the compound of Synthesis Example 21.

비교예Comparative Example 1 One

합성예 21의 화합물 대신 비교 합성예 1의 폴리머를 사용한 것을 제외하고는, 실시예 1과 동일하게 하여 비교예 1에 따른 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition according to Comparative Example 1 was prepared in the same manner as in Example 1, except that the polymer of Comparative Synthesis Example 1 was used in place of the compound of Synthesis Example 21.

평가 2: Evaluation 2: 색좌표Color coordinates , 휘도 및 명암비 측정, Brightness and contrast ratio

탈지 세척한 두께 1 mm의 유리 기판 상에 1 ㎛ 내지 3 ㎛의 두께로 상기 실시예 1 내지 실시예 5 및 비교예 1의 감광성 수지 조성물을 도포하고, 90℃의 핫 플레이트 상에서 2분 동안 건조시켜 도막을 수득하였다. 계속해서 도막에 365nm의 주파장을 가진 고압수은램프를 사용하여 노광하여 수득하였다. 200℃의 열풍순환식 건조로 안에서 5분 동안 건조시켜 수득하였다. 화소층은 분광광도계(MCPD3000, Otsuka electronic社)를 이용하여 색좌표(x, y), 휘도(Y) 및 명암비를 측정하여, 하기 표 3에 기재하였다.
The photosensitive resin compositions of Examples 1 to 5 and Comparative Example 1 were applied on a 1 mm thick glass substrate having a thickness of 1 to 3 占 퐉 and dried on a hot plate at 90 占 폚 for 2 minutes A coating film was obtained. Subsequently, a coating film was obtained by exposure using a high-pressure mercury lamp having a dominant wavelength of 365 nm. And dried in a hot air circulating drying oven at 200 ° C for 5 minutes. The color layer (x, y), luminance (Y), and contrast ratio were measured using a spectrophotometer (MCPD3000, Otsuka electronic Co.)

색좌표 (x, y)The color coordinates (x, y) 휘도 (Y)Luminance (Y) 명암비Contrast ratio 실시예 1Example 1 0.269, 0.6200.269, 0.620 51.351.3 1125011250 실시예 2Example 2 0.267, 0.6200.267, 0.620 51.151.1 1122411224 실시예 3Example 3 0.265, 0.6200.265, 0.620 50.550.5 1126311263 실시예 4Example 4 0.266, 0.6200.266, 0.620 51.051.0 1116511165 실시예 5Example 5 0.263, 0.6200.263, 0.620 50.850.8 1118011180 비교예 1Comparative Example 1 0.267, 0.6200.267, 0.620 49.149.1 98509850

상기 표 3으로부터, 일 구현예에 따른 화합물 또는 폴리머를 염료로 포함하는 실시예 1 내지 실시예 5의 감광성 수지 조성물이 상기 화합물 또는 폴리머를 염료로 포함하지 않은 비교예 1의 감광성 수지 조성물보다 우수한 색특성을 나타냄을 확인할 수 있다.
From the above Table 3, it can be seen that the photosensitive resin compositions of Examples 1 to 5 containing the compound or polymer according to one embodiment as a dye are superior to the photosensitive resin composition of Comparative Example 1 in which the compound or polymer is not contained as a dye , Respectively.

이상 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고, 특허청구범위와 발명의 상세한 설명 및 첨부한 도면의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고, 이 또한 본 발명의 범위에 속하는 것은 당연하다.While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, And it goes without saying that the invention belongs to the scope of the invention.

Claims (16)

하기 화학식 1로 표시되는 화합물:
[화학식 1]
Figure pat00119

상기 화학식 1에서,
R1 및 R2는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, *-C(=O)OR' 또는 *-OC(=O)R' 이고,
상기 R'은 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C2 내지 C10 알케닐기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,
단, 상기 R1 및 R2 중 어느 하나는 치환 또는 비치환된 아크릴레이트기를 포함하고,
R3은 치환 또는 비치환된 C1 내지 C20 알킬기이다.
A compound represented by the following formula (1):
[Chemical Formula 1]
Figure pat00119

In Formula 1,
R 1 and R 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, -C (= O) OR 'or * -OC (= O)
Wherein R 'is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group or a substituted or unsubstituted C6 to C20 aryl group,
Provided that any one of R 1 and R 2 includes a substituted or unsubstituted acrylate group,
R 3 is a substituted or unsubstituted C1 to C20 alkyl group.
제1항에 있어서,
상기 치환 또는 비치환된 아크릴레이트기는 하기 화학식 2로 표시되는 화합물:
[화학식 2]
Figure pat00120

상기 화학식 2에서,
R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.
The method according to claim 1,
Wherein the substituted or unsubstituted acrylate group is represented by the following formula 2:
(2)
Figure pat00120

In Formula 2,
R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
제1항에 있어서,
상기 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 화학식 6으로 이루어진 군에서 선택된 어느 하나로 표시되는 화합물:
[화학식 3]
Figure pat00121

[화학식 4]
Figure pat00122

[화학식 5]
Figure pat00123

[화학식 6]
Figure pat00124

상기 화학식 3 내지 화학식 6에서,
L1 내지 L3은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 *-L'-C(=O)O-L"-* 이고,
상기 L' 및 L"은 각각 독립적으로 치환 또는 비치환된 C1 내지 C5 알킬렌기 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,
R3 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기이고,
R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.
The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by any one selected from the group consisting of the following Chemical Formulas 3 to 6:
(3)
Figure pat00121

[Chemical Formula 4]
Figure pat00122

[Chemical Formula 5]
Figure pat00123

[Chemical Formula 6]
Figure pat00124

In the above Chemical Formulas 3 to 6,
L 1 to L 3 each independently represent a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group or * -L'-C (= O) OL "- *
Wherein L 'and L "are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,
R 3 and R 5 are each independently a substituted or unsubstituted C 1 to C 20 alkyl group,
R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
제1항에 있어서,
상기 화학식 1은 화학식 7 내지 화학식 20으로 이루어진 군에서 선택된 어느 하나로 표시되는 화합물.
[화학식 7]
Figure pat00125

[화학식 8]
Figure pat00126

[화학식 9]
Figure pat00127

[화학식 10]
Figure pat00128

[화학식 11]
Figure pat00129

[화학식 12]
Figure pat00130

[화학식 13]
Figure pat00131

[화학식 14]
Figure pat00132

[화학식 15]
Figure pat00133

[화학식 16]
Figure pat00134

[화학식 17]
Figure pat00135

[화학식 18]
Figure pat00136

[화학식 19]
Figure pat00137

[화학식 20]
Figure pat00138

The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by any one selected from the group consisting of Formulas (7) to (20).
(7)
Figure pat00125

[Chemical Formula 8]
Figure pat00126

[Chemical Formula 9]
Figure pat00127

[Chemical formula 10]
Figure pat00128

(11)
Figure pat00129

[Chemical Formula 12]
Figure pat00130

[Chemical Formula 13]
Figure pat00131

[Chemical Formula 14]
Figure pat00132

[Chemical Formula 15]
Figure pat00133

[Chemical Formula 16]
Figure pat00134

[Chemical Formula 17]
Figure pat00135

[Chemical Formula 18]
Figure pat00136

[Chemical Formula 19]
Figure pat00137

[Chemical Formula 20]
Figure pat00138

제1항에 있어서,
상기 화학식 1은 화학식 21 내지 화학식 24로 이루어진 군에서 선택된 어느 하나로 표시되는 화합물.
[화학식 21]
Figure pat00139

[화학식 22]
Figure pat00140

[화학식 23]
Figure pat00141

[화학식 24]
Figure pat00142

The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the formulas (21) to (24).
[Chemical Formula 21]
Figure pat00139

[Chemical Formula 22]
Figure pat00140

(23)
Figure pat00141

&Lt; EMI ID =
Figure pat00142

상기 화학식 1은 하기 화학식 25 또는 화학식 26으로 표시되는 화합물.
[화학식 25]
Figure pat00143

[화학식 26]
Figure pat00144

The compound represented by Formula 1 is represented by Formula 25 or Formula 26 below.
(25)
Figure pat00143

(26)
Figure pat00144

제1항에 있어서,
상기 화합물은 황색 염료인 화합물.
The method according to claim 1,
Wherein said compound is a yellow dye.
제7항에 있어서,
상기 황색 염료는 400nm 내지 500nm의 파장범위에서 최대 흡광영역을 가지는 화합물.
8. The method of claim 7,
Wherein the yellow dye has a maximum light absorption region in a wavelength range of 400 nm to 500 nm.
하기 화학식 1로 표시되는 화합물을 모노머로 포함하는 폴리머:
[화학식 1]
Figure pat00145

상기 화학식 1에서,
R1 및 R2는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, *-C(=O)OR' 또는 *-OC(=O)R' 이고,
상기 R'은 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C2 내지 C10 알케닐기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,
단, 상기 R1 및 R2 중 어느 하나는 하기 화학식 2로 표시되는 치환기를 포함하고,
[화학식 2]
Figure pat00146

(상기 화학식 2에서,
R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다)
R3은 치환 또는 비치환된 C1 내지 C20 알킬기이다.
A polymer comprising a compound represented by the following formula (1) as a monomer:
[Chemical Formula 1]
Figure pat00145

In Formula 1,
R 1 and R 2 are each independently a substituted or unsubstituted C1 to C20 alkyl group, -C (= O) OR 'or * -OC (= O)
Wherein R 'is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group or a substituted or unsubstituted C6 to C20 aryl group,
Provided that any one of R 1 and R 2 includes a substituent represented by the following formula (2)
(2)
Figure pat00146

(In the formula (2)
R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group)
R 3 is a substituted or unsubstituted C1 to C20 alkyl group.
제9항에 있어서,
상기 폴리머는 하기 화학식 27 내지 화학식 30으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나의 반복단위를 포함하는 폴리머:
[화학식 27]
Figure pat00147

[화학식 28]
Figure pat00148

[화학식 29]
Figure pat00149

[화학식 30]
Figure pat00150

상기 화학식 27 내지 화학식 30에서,
L1 내지 L3은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬렌기, 치환 또는 비치환된 C6 내지 C20 아릴렌기 또는 *-L'-C(=O)O-L"-* 이고,
상기 L' 및 L"은 각각 독립적으로 치환 또는 비치환된 C1 내지 C5 알킬렌기 또는 치환 또는 비치환된 C6 내지 C12 아릴렌기이고,
R3 및 R5는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기이고,
R4는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.
10. The method of claim 9,
Wherein the polymer is a polymer comprising any one repeating unit selected from the group consisting of repeating units represented by the following Chemical Formulas 27 to 30:
(27)
Figure pat00147

(28)
Figure pat00148

[Chemical Formula 29]
Figure pat00149

(30)
Figure pat00150

In the above Chemical Formulas 27 to 30,
L 1 to L 3 each independently represent a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group or * -L'-C (= O) OL "- *
Wherein L 'and L "are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,
R 3 and R 5 are each independently a substituted or unsubstituted C 1 to C 20 alkyl group,
R 4 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
제10항에 있어서,
상기 폴리머는 하기 화학식 31 및 화학식 32로 표시되는 반복단위를 더 포함하는 폴리머:
[화학식 31]
Figure pat00151

[화학식 32]
Figure pat00152

상기 화학식 31 및 화학식 32에서,
R6는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,
L4는 치환 또는 비치환된 C1 내지 C10 알킬렌기이다.
11. The method of claim 10,
Wherein the polymer further comprises a repeating unit represented by the following general formula (31) and (32):
(31)
Figure pat00151

(32)
Figure pat00152

In the above formulas (31) and (32)
R 6 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
L 4 is a substituted or unsubstituted C1 to C10 alkylene group.
제11항에 있어서,
상기 폴리머는,
상기 화학식 27 내지 화학식 30으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나의 반복단위 40 중량% 내지 60 중량%;
상기 화학식 31로 표시되는 반복단위 5 중량% 내지 25 중량%; 및
상기 화학식 32로 표시되는 반복단위 25 중량% 내지 45 중량%
를 포함하는 폴리머.
12. The method of claim 11,
Preferably,
40 to 60% by weight of any one repeating unit selected from the group consisting of repeating units represented by formulas (27) to (30);
5 to 25% by weight of the repeating unit represented by the formula (31); And
25% by weight to 45% by weight of the repeating unit represented by the formula (32)
&Lt; / RTI &gt;
제10항에 있어서,
상기 화학식 27로 표시되는 반복단위는 하기 화학식 33 내지 화학식 46으로 표시되는 반복단위로 이루어진 군에서 선택된 어느 하나인 폴리머.
[화학식 33]
Figure pat00153

[화학식 34]
Figure pat00154

[화학식 35]
Figure pat00155

[화학식 36]
Figure pat00156

[화학식 37]
Figure pat00157

[화학식 38]
Figure pat00158

[화학식 39]
Figure pat00159

[화학식 40]
Figure pat00160

[화학식 41]
Figure pat00161

[화학식 42]
Figure pat00162

[화학식 43]
Figure pat00163

[화학식 44]
Figure pat00164

[화학식 45]
Figure pat00165

[화학식 46]
Figure pat00166

11. The method of claim 10,
Wherein the repeating unit represented by the formula (27) is any one selected from the group consisting of repeating units represented by the following formulas (33) to (46).
(33)
Figure pat00153

(34)
Figure pat00154

(35)
Figure pat00155

(36)
Figure pat00156

(37)
Figure pat00157

(38)
Figure pat00158

[Chemical Formula 39]
Figure pat00159

(40)
Figure pat00160

(41)
Figure pat00161

(42)
Figure pat00162

(43)
Figure pat00163

(44)
Figure pat00164

[Chemical Formula 45]
Figure pat00165

(46)
Figure pat00166

제10항에 있어서,
상기 화학식 28로 표시되는 반복단위는 하기 화학식 47 또는 화학식 48로 표시되는 반복단위인 폴리머.
[화학식 47]
Figure pat00167

[화학식 48]
Figure pat00168

11. The method of claim 10,
Wherein the repeating unit represented by the formula (28) is a repeating unit represented by the following formula (47) or (48).
(47)
Figure pat00167

(48)
Figure pat00168

제10항에 있어서,
상기 화학식 29로 표시되는 반복단위는 하기 화학식 49 또는 화학식 50으로 표시되는 반복단위인 폴리머.
[화학식 49]
Figure pat00169

[화학식 50]
Figure pat00170

11. The method of claim 10,
Wherein the repeating unit represented by the formula (29) is a repeating unit represented by the following formula (49) or (50).
(49)
Figure pat00169

(50)
Figure pat00170

제10항에 있어서,
상기 화학식 30으로 표시되는 반복단위는 하기 화학식 51 또는 화학식 52로 표시되는 반복단위인 폴리머.
[화학식 51]
Figure pat00171

[화학식 52]
Figure pat00172
11. The method of claim 10,
Wherein the repeating unit represented by the formula (30) is a repeating unit represented by the following formula (51) or (52).
(51)
Figure pat00171

(52)
Figure pat00172
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JP6054798B2 (en) * 2013-03-29 2016-12-27 富士フイルム株式会社 Color filter manufacturing method, color filter, and solid-state imaging device

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KR20190078428A (en) * 2017-12-26 2019-07-04 삼성에스디아이 주식회사 Optical film for improving contrast ratio, polarizing plate comprising the same and liquid crystal display apparatus comprising the same
KR20200122149A (en) * 2019-04-17 2020-10-27 삼성에스디아이 주식회사 Photosensitive resin composition and photosensitive resin layer using the same, color filter
KR20230026812A (en) * 2021-08-18 2023-02-27 삼성에스디아이 주식회사 Photosensitive resin composition, photosensitive resin layer using the same, color filter and display device

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TWI580737B (en) 2017-05-01

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