KR100976460B1 - Photosensitive resin composition for color filter and color filter using same - Google Patents
Photosensitive resin composition for color filter and color filter using same Download PDFInfo
- Publication number
- KR100976460B1 KR100976460B1 KR1020080085370A KR20080085370A KR100976460B1 KR 100976460 B1 KR100976460 B1 KR 100976460B1 KR 1020080085370 A KR1020080085370 A KR 1020080085370A KR 20080085370 A KR20080085370 A KR 20080085370A KR 100976460 B1 KR100976460 B1 KR 100976460B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- substituted
- unsubstituted
- resin composition
- photosensitive resin
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 51
- 239000000049 pigment Substances 0.000 claims abstract description 135
- 239000000178 monomer Substances 0.000 claims abstract description 22
- 125000003277 amino group Chemical group 0.000 claims abstract description 20
- 239000002270 dispersing agent Substances 0.000 claims abstract description 20
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000011230 binding agent Substances 0.000 claims abstract description 12
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 230000035945 sensitivity Effects 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 47
- -1 azide compounds Chemical class 0.000 description 32
- 239000006185 dispersion Substances 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 23
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- 239000000126 substance Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
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- 230000008569 process Effects 0.000 description 13
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- 238000002360 preparation method Methods 0.000 description 11
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- 230000000052 comparative effect Effects 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
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- 239000000758 substrate Substances 0.000 description 5
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004070 electrodeposition Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 230000007261 regionalization Effects 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
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- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229940017219 methyl propionate Drugs 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
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- FJKOQFIGFHTRRW-UHFFFAOYSA-N (2-methoxy-3-methylphenyl)-(3-methylphenyl)methanone Chemical compound COC1=C(C)C=CC=C1C(=O)C1=CC=CC(C)=C1 FJKOQFIGFHTRRW-UHFFFAOYSA-N 0.000 description 1
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- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 1
- MPNIGZBDAMWHSX-UHFFFAOYSA-N 2-(4-methylphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(C)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 MPNIGZBDAMWHSX-UHFFFAOYSA-N 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Abstract
본 발명은 컬러 필터용 감광성 수지 조성물에 관한 것으로서, 이 감광성 수지 조성물은 (A) 아미노기를 포함하는 디케토피롤로피롤계 안료유도체, (B) 안료, (C) 분산제, (D) 바인더 수지, (E) 광중합 개시제, (F) 광중합성 모노머, 및 (G) 용매를 포함한다. The present invention relates to a photosensitive resin composition for color filters, wherein the photosensitive resin composition includes (A) a diketopyrrolopyrrole pigment derivative containing an amino group, (B) pigment, (C) dispersant, (D) binder resin, ( E) a photoinitiator, (F) photopolymerizable monomer, and (G) solvent.
본 발명의 컬러 필터용 감광성 수지 조성물은 노광 및 현상 시에 해상도가 높은 미세 패턴을 구현할 수 있으며, 잔사를 현저히 감소시킬 수 있다. 따라서 본 발명의 컬러 필터용 감광성 수지 조성물을 이용하여 감도 및 화소가 향상된 CMOS 또는 CCD 이미지 센서 또는 일반적인 LCD의 디스플레이 장치에 사용되는 컬러 필터를 제조할 수 있다. The photosensitive resin composition for color filters of the present invention can implement a fine pattern having a high resolution at the time of exposure and development, and can significantly reduce the residue. Therefore, using the photosensitive resin composition for color filters of this invention, the color filter used for the display device of a CMOS or CCD image sensor or a general LCD which improved the sensitivity and the pixel can be manufactured.
컬러 필터, 염료, 잔사, 해상도 Color filter, dye, residue, resolution
Description
본 발명은 컬러 필터(color filter)용 감광성 수지 조성물 및 이로부터 제조된 컬러 필터에 관한 것으로서, 보다 상세하게는 패턴의 잔사를 감소시키고 해상도를 향상시킬 수 있는 컬러 필터용 감광성 수지 조성물 및 이로부터 제조된 컬러 필터에 관한 것이다.The present invention relates to a photosensitive resin composition for a color filter and a color filter prepared therefrom, and more particularly, to a photosensitive resin composition for a color filter capable of reducing the residue of a pattern and improving a resolution thereof. To a color filter.
컬러필터는 액정표시장치, 카메라의 광학필터 등에 사용되는 것으로서, 3종이상의 색상으로 착색된 미세한 영역을 고체촬영소자 또는 투명기판상에 코팅하여 착색박막으로 제조된다. 이와 같은 착색박막은 통상 염색법, 인쇄법, 전착법, 안료분산법, 또는 잉크젯 방식 등에 의하여 형성된다. The color filter is used in a liquid crystal display device, an optical filter of a camera, and the like, and is manufactured as a colored thin film by coating a fine region colored with three or more colors on a solid state photographing device or a transparent substrate. Such colored thin films are usually formed by dyeing, printing, electrodeposition, pigment dispersion, inkjet, or the like.
염색법의 경우, 기판상에 미리 젤라틴 등의 천연 감광성 수지, 아민 변성 폴리비닐 알코올, 또는 아민 변성 아크릴계 수지 등의 염색기재를 가진 화상을 형성시킨 후, 직접염료 등의 염료로 염색하여 착색박막을 형성한다. 그러나, 상기 염색법의 경우, 다색 박막을 동일 기판 상에 형성하기 위해서는 색상을 변화시킬 때 마다 방염가공을 할 필요가 있기 때문에, 공정이 매우 복잡해지고 공정 시간이 지연되는 문제점이 있다. In the dyeing method, an image having a dye-based base material such as a natural photosensitive resin such as gelatin, an amine modified polyvinyl alcohol, or an amine modified acrylic resin is formed on a substrate in advance, and then dyed with a dye such as a direct dye to form a colored thin film. do. However, in the case of the dyeing method, in order to form a multi-colored thin film on the same substrate, it is necessary to flame-resistant process every time the color is changed, there is a problem that the process is very complicated and the process time is delayed.
또한, 상기 염색법에 일반적으로 사용하는 염료, 및 수지 자체의 선명성과 분산성은 양호하나, 내광성, 내습성, 및 가장 중요한 특성인 내열성이 나쁘다는 단점이 있다. 예컨대, 대한민국 특허공개 제1991-4717호와 대한민국 특허공개 제1994-7778호에서는 염료로서 아조 화합물과 아지드 화합물을 사용하고 있지만, 안료형에 비하여 내열성, 및 내구성이 떨어지는 단점이 있다.In addition, although the sharpness and dispersibility of the dye and the resin itself, which are generally used in the dyeing method, are good, there are disadvantages in that light resistance, moisture resistance, and heat resistance, which is the most important characteristic, are poor. For example, although Korean Patent Publication Nos. 1991-4717 and Korean Patent Publication No. 194-7778 use azo compounds and azide compounds as dyes, they have disadvantages of poor heat resistance and durability as compared to pigments.
인쇄법에서는 열경화성, 또는 광경화성 수지에 안료를 분산시킨 잉크를 사용하여 인쇄를 행한 후, 열 또는 광으로 경화시킴으로써 착색박막을 형성시킨다. 이 방법에 의하면 타 방법에 비해 재료비를 절감할 수는 있지만, 고도로 정밀하고 세밀한 화상 형성이 곤란하고, 형성되는 박막층이 균일하지 못한 단점이 있다. In the printing method, printing is carried out using an ink in which a pigment is dispersed in a thermosetting or photocurable resin, and then a colored thin film is formed by curing with heat or light. According to this method, the material cost can be reduced compared to other methods, but it is difficult to form highly precise and detailed images, and the thin film layer formed is not uniform.
대한민국 특허공개 제1995-7003746호, 및 대한민국 특허공개 제1996-11513호에서는 잉크젯 방식을 이용한 컬러필터의 제조방법을 제안하고 있다. 상기 특허에서는 색소의 인쇄를 위하여 노즐에서 분사되는 컬러 레지스트 조성물이 염료형으로 되어있기 때문에, 염색법과 마찬가지로 내구성, 및 내열성이 떨어지게 된다.Korean Patent Publication No. 1995-9003746 and Korean Patent Publication No. 1996-11513 propose a method for manufacturing a color filter using an inkjet method. In this patent, since the color resist composition sprayed from the nozzle for dye printing is dye-type, durability and heat resistance are inferior as in the dyeing method.
이와 달리, 대한민국 특허공개 제1993-7000858호, 대한민국 특허공개 제1996-29904호에서는 전기침전법을 이용한 전착법을 제안하고 있다. 상기 전착법은 정밀한 착색막을 형성할 수 있고, 안료를 사용하므로 내열성, 및 내광성이 우수하다는 장점이 있으나, 화소크기가 정밀화되어 전극패턴이 세밀하게 되면, 패턴의 양쪽 끝에 전기저항으로 인한 착색 얼룩이 나타나거나 착색막 두께가 두꺼워져서, 고 도의 정밀성을 요구하는 컬러필터에 적용하기는 어렵다.On the contrary, Korean Patent Publication No. 1993-7000858 and Korean Patent Publication No. 1996-29904 propose an electrodeposition method using an electroprecipitation method. The electrodeposition method can form a precise colored film and has the advantage of excellent heat resistance and light resistance since the use of a pigment, but when the pixel size is precise and the electrode pattern is fine, colored stains due to electrical resistance appear at both ends of the pattern. In addition, since the thickness of the colored film becomes thick, it is difficult to apply to color filters requiring high precision.
안료분산법은 블랙 매트릭스가 제공된 투명한 기판 위에 착색제를 함유하는 광중합성 조성물을 코팅-노광-현상-열경화 시키는 일련의 과정을 반복함으로써 착색박막을 형성시키는 방법이다. 상기 안료분산법은 컬러필터의 가장 중요한 성질인 내열성 및 내구성을 향상시킬 수 있고, 필름의 두께를 균일하게 조절할 수 있다는 장점이 있다. 또한, 미세 패턴의 구현이 가능하고 제조 방법이 비교적 용이하여 보편적으로 채용되고 있다. 예컨대, 대한민국 특허공개 제1992-7002502호, 대한민국 특허공고 제1994-5617호, 대한민국 특허공고 제1995-11163호, 대한민국 특허공개 제1995-7000359호 등에서는 안료분산을 이용한 컬러 레지스트의 제조 방법이 제안되고 있다.The pigment dispersion method is a method of forming a colored thin film by repeating a series of processes of coating-exposure-developing-thermosetting a photopolymerizable composition containing a colorant on a transparent substrate provided with a black matrix. The pigment dispersion method can improve heat resistance and durability, which are the most important properties of the color filter, and have the advantage of uniformly adjusting the thickness of the film. In addition, since the fine pattern can be implemented and the manufacturing method is relatively easy, it is widely adopted. For example, Republic of Korea Patent Publication No. 1992-7002502, Republic of Korea Patent Publication 199-5617, Republic of Korea Patent Publication 1995-11163, Republic of Korea Patent Publication 1995-7000359 propose a method for producing a color resist using pigment dispersion. It is becoming.
그러나, 상기 방법은 화소를 형성하기 위하여 적색(R), 녹색(G), 및 청색(B)에 대하여 각각 코팅, 노광, 현상, 및 경화하는 과정을 요구하여 제조 공정 라인이 너무 길어지고 공정간 제어인자가 많아짐에 따라 수율 관리에 어려움이 있다. 또한, 모니터, TV 등에서 높은 색재현률과 높은 명암비가 요구됨에 따라, 코팅막의 두께를 크게 하여야 하는 등 실제 생산 공정에서 여러 문제점이 있다.However, the process requires coating, exposure, developing, and curing processes for red (R), green (G), and blue (B), respectively, to form a pixel, resulting in too long a manufacturing process line and an interprocess As the number of control factors increases, it is difficult to manage yield. In addition, as a high color reproduction ratio and high contrast ratio are required in a monitor and a TV, there are various problems in the actual production process such as increasing the thickness of the coating film.
이러한 문제점을 극복하기 위해 최근에는 종래의 안료분산법을 대체하기 위한 여러 가지 새로운 공정방식이 사용되고 있는데, 대표적인 것이 잉크젯 프린팅 방식이다. 상기 잉크젯 프린팅은 유리기판상에 블랙 매트릭스 등의 차광층을 형성하고 상기 화소 공간에 잉크를 주입하는 방식이다. 상기 잉크젯 프린팅 방식은 컬러필터를 제조함에 있어서 별도의 코팅, 노광, 현상 등의 공정이 불필요하므로 공 정에 필요한 재료를 절감할 수 있고 공정의 단순화를 가능하게 할 수 있다. In order to overcome this problem, a number of new process methods are recently used to replace the conventional pigment dispersion method, and an inkjet printing method is representative. The inkjet printing is a method of forming a light blocking layer such as a black matrix on a glass substrate and injecting ink into the pixel space. Since the inkjet printing method does not require a separate coating, exposure, or development process in manufacturing a color filter, it is possible to reduce materials required for the process and to simplify the process.
상기 잉크젯 방식에서, 컬러필터가 균일하고 우수한 컬러특성을 갖기 위해서는 픽셀간 컬러층이 균일하게 형성되어야 한다. 이는 잉크가 헤드에서 분사 시에 노즐의 막힘이 전혀 없어야 하며, 픽셀 내에 똑같은 양과 방울수로 떨어져야 한다. 따라서, 헤드의 분사노즐 표면과 컬러잉크 간의 상호작용은 분사 성능을 크게 좌우하는 요소이다.In the inkjet method, in order for the color filter to have uniform and excellent color characteristics, the color layer between pixels must be uniformly formed. This means that when the ink is ejected from the head, there should be no clogging of the nozzles and it should fall in the same amount and droplets within the pixel. Therefore, the interaction between the surface of the injection nozzle of the head and the color ink is a factor that greatly influences the injection performance.
잉크젯 방식을 이용하여 형성된 패턴은 200℃ 내외의 온도로 가열하여 경화시키는 방법을 사용함으로 안료분산법에서 형성된 패턴처럼 모노머의 경화도가 낮아져 막강도가 약해짐으로써 내열성 및 내화학성이 불량해지는 문제가 발생할 수 있다. 잉크젯 방식에 의해 제작된 컬러필터는 안료분산법과 마찬가지로 막강도, 내화학성, 및 막강도와 같은 높은 신뢰성을 요구하고 있으며, 이러한 특성을 만족하지 못하면 컬러필터의 후공정에서 색변, 또는 패턴 침해 등의 문제점이 야기된다.The pattern formed by using the inkjet method is heated to a temperature of about 200 ° C. to harden the monomer, as the pattern formed in the pigment dispersion method, so that the hardness of the monomer is low and the film strength is weakened, resulting in poor heat resistance and chemical resistance. Can be. Like the pigment dispersion method, the color filter manufactured by the inkjet method requires high reliability such as film strength, chemical resistance, and film strength. If this property is not satisfied, problems such as color change or pattern infringement in the subsequent process of the color filter are not satisfied. This is caused.
본 발명의 목적은 패턴 형성시 해상도를 증가시키고 잔사를 감소시킬 수 있도록, 산성 관능기를 갖는 분산제로 분산이 가능한 안료 유도체를 포함하는 컬러 필터용 감광성 수지 조성물을 제공하는 것이다. It is an object of the present invention to provide a photosensitive resin composition for color filters comprising a pigment derivative capable of dispersing with a dispersant having an acidic functional group so as to increase the resolution and reduce the residue upon pattern formation.
본 발명의 다른 목적은, 상기 컬러 필터용 감광성 수지 조성물을 사용하여 제조된 컬러 필터를 제공하는 것이다. Another object of the present invention is to provide a color filter manufactured using the photosensitive resin composition for color filters.
본 발명이 이루고자 하는 기술적 과제들은 이상에서 언급한 기술적 과제들로 제한되지 않으며, 언급되지 않은 또 다른 기술적 과제들은 아래의 기재로부터 당업자에게 명확하게 이해될 수 있을 것이다.Technical problems to be achieved by the present invention are not limited to the technical problems mentioned above, and other technical problems not mentioned will be clearly understood by those skilled in the art from the following description.
상기 목적을 달성하기 위한 본 발명의 일 구현예에 따르면, (A) 아미노기를 포함하는 디케토피롤로피롤계 안료유도체, (B) 안료, (C) 분산제, (D) 바인더 수지, (E) 광중합 개시제, (F) 광중합성 모노머, 및 (G) 용매를 포함하는 컬러 필터용 감광성 수지 조성물을 제공한다.According to one embodiment of the present invention for achieving the above object, (A) a diketopyrrolopyrrole pigment derivative containing an amino group, (B) pigment, (C) dispersant, (D) binder resin, (E) photopolymerization The photosensitive resin composition for color filters containing an initiator, (F) photopolymerizable monomer, and (G) solvent is provided.
본 발명의 다른 일 구현예에 따르면, 상기 컬러 필터용 감광성 수지 조성물을 이용하여 제조된 컬러 필터를 제공한다.According to another embodiment of the present invention, a color filter manufactured by using the photosensitive resin composition for color filters is provided.
기타 본 발명의 구현예들의 구체적인 사항은 이하의 상세한 설명에 포함되어 있다. Other specific details of embodiments of the present invention are included in the following detailed description.
본 발명의 컬러 필터용 감광성 수지 조성물은 노광 및 현상 시에 해상도가 높은 미세 패턴을 구현할 수 있으며, 잔사를 현저히 감소시킬 수 있다. 따라서 본 발명의 컬러 필터용 감광성 수지 조성물을 이용하여 감도 및 화소가 향상된 CMOS 또는 CCD 이미지 센서 또는 일반적인 LCD의 디스플레이 장치에 사용되는 컬러 필터를 제조할 수 있다. The photosensitive resin composition for color filters of the present invention can implement a fine pattern having a high resolution at the time of exposure and development, and can significantly reduce the residue. Therefore, using the photosensitive resin composition for color filters of this invention, the color filter used for the display device of a CMOS or CCD image sensor or a general LCD which improved the sensitivity and the pixel can be manufactured.
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, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.
본 발명의 일 구현예에 따른 컬러 필터용 감광성 수지 조성물은 (A) 아미노기를 포함하는 디케토피롤로피롤계 안료유도체; (B) 안료; (C) 분산제; (D) 바인더 수지; (E) 광중합 개시제; (F) 광중합성 모노머; 및 (G) 용매를 포함한다. Photosensitive resin composition for a color filter according to an embodiment of the present invention (A) a diketopyrrolopyrrole pigment derivative containing an amino group; (B) pigments; (C) dispersants; (D) binder resins; (E) photoinitiator; (F) photopolymerizable monomers; And (G) a solvent.
본 명세서에서 특별한 언급이 없는 한, “알킬기”란 탄소수 1 내지 30의 알킬기를, "알케닐기”란 탄소수 2 내지 16의 알케닐기를, "알키닐기"란 탄소수 3 내지 30의 알키닐기를, "아릴기”란 탄소수 6 내지 30의 아릴기를, "아릴렌기”란 탄소수 6 내지 30의 아릴렌기를, "헤테로아릴기"란 탄소수 2 내지 30의 헤테로아릴기를, “아릴알킬기”란 탄소수 6 내지 30의 아릴알킬기를, "사이클로알킬기”란 탄소수 5 내지 20의 사이클로알킬기를, "헤테로사이클로알킬기”란 탄소수 2 내지 30의 헤테로사이클로알킬기를, "사이클로알케닐기"란 탄소수 5 내지 30의 사이클로알케닐기를, "사이클로알키닐기란”란 탄소수 5 내지 20의 사이클로알키닐기를, “알콕시기”란 탄소수 1 내지 30의 알콕시기를, "알칸올기"란 탄소수 1 내지 30 알칸올기를 의미한다. 또한 알킬 아미노기 및 알콕시 아미노기란 아미노기의 수소 원자 중 일부가 알킬기 및 알콕시기로 치환된 것으로서, 이때 알킬기 및 알콕시기는 상술한 알킬기 및 알콕시기의 정의와 동일하다.Unless stated otherwise in the specification, an "alkyl group" means an alkyl group having 1 to 30 carbon atoms, an "alkenyl group" means an alkenyl group having 2 to 16 carbon atoms, an "alkynyl group" means an alkynyl group having 3 to 30 carbon atoms, " Aryl group ”means an aryl group having 6 to 30 carbon atoms,“ arylene group ”means an arylene group having 6 to 30 carbon atoms,“ heteroaryl group ”means a heteroaryl group having 2 to 30 carbon atoms, and“ arylalkyl group ”means 6 to 30 carbon atoms Arylalkyl group is a cycloalkyl group having 5 to 20 carbon atoms as a "cycloalkyl group", a heterocycloalkyl group having 2 to 30 carbon atoms as a "heterocycloalkyl group" and a cycloalkenyl group having 5 to 30 carbon atoms as a "cycloalkenyl group" "Cycloalkynyl group" means a cycloalkynyl group having 5 to 20 carbon atoms, "alkoxy group" means an alkoxy group having 1 to 30 carbon atoms, and an "alkanol group" means a 1 to 30 alkanol group. In addition, an alkyl amino group and an alkoxy amino group are those in which a part of the hydrogen atoms of the amino group is substituted with an alkyl group and an alkoxy group, wherein the alkyl group and the alkoxy group have the same definitions as the above-described alkyl group and alkoxy group.
또한 “치환”이란, 본 발명의 작용기중의 하나 이상의 수소 원자가 할로겐 원자(F, Br, Cl, 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기(-NH2, -NH(R), -N(R')(R"), R, R' 및 R"은 동일하거나 서로 상이하며, 각각 독립적으로 탄소수 1 내지 10의 알킬기임), 아미디노기, 히드라진 또는 히드라존기, 카르복실기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 사이클로알킬기, 치환 또는 비치환된 헤테로아릴기, 및 치환 또는 비치환 헤테로사이클로알킬기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한다. 이러한 정의는 상기 치환의 정의에서 언급된 "치환"에도 동일하게 적용된다. "Substituted" means that at least one hydrogen atom in the functional group of the present invention is a halogen atom (F, Br, Cl, or I), hydroxy group, nitro group, cyano group, amino group (-NH 2 , -NH (R),- N (R ') (R "), R, R' and R" are the same or different from each other, each independently an alkyl group having 1 to 10 carbon atoms, amidino group, hydrazine or hydrazone group, carboxyl group, substituted or unsubstituted Substituted with one or more substituents selected from the group consisting of a substituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heterocycloalkyl group Means that. This definition applies equally to the "substitutions" mentioned in the definition of substitution above.
또한 "헤테로"란 하나의 고리에 N, O, S, 및 P로 이루어진 군에서 선택되는 헤테로원자를 1 내지 3개 포함하는 것이 바람직하다.Also, "hetero" preferably contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P in one ring.
해상도의 증가 및 잔사의 감소를 위한 중요 요소로는 광중합 개시제, 모노머, 및 바인더의 종류와 이들의 조성비, 그리고 안료 분산액을 들 수 있다. 이러한 요소 중 안료 분산액은 미세한 패턴을 형성하기 위해 분산 입도가 작아야 하며, 현상시 잔사가 남지 않는 조성으로 이루어져야 한다. 기존 안료 분산액의 분산 입도가 작기 위해서는 사용되는 안료의 1차 입도가 작아야 하며 분산제의 종류 및 그 양 또한 중요한 항목이 된다. Important factors for increasing the resolution and reducing the residue include kinds of photopolymerization initiators, monomers, and binders, their composition ratios, and pigment dispersions. Among these elements, the pigment dispersion should have a small particle size in order to form a fine pattern, and should have a composition in which no residue is left during development. In order for the dispersion particle size of the existing pigment dispersion to be small, the primary particle size of the pigment used must be small, and the type and amount of the dispersant are also important items.
안료분산액에 사용되는 분산제의 경우 컬러 필터용 감광성 수지 조성물의 패턴 형성 후 남는 잔사에 영향을 많이 미친다. 이에 안료분산액 제조시 현상액으로 사용되는 알칼리 수용액에 대한 용해성은 중요한 문제이다. 따라서 카르복실기 또는 인산기와 같은 산성기를 갖는 분산제를 사용할 경우 잔사 개선을 할 수 있다. 따라서, 본 발명에서는 이러한 분산제를 사용하기 위하여, 카르복실기 또는 인산기 와 같은 산성기와 상호작용을 할 수 있으며, 분산할 안료와 구조가 유사한 아미노기를 포함하는 안료 유도체를 사용하여 분산 및 안정성을 확보하였다. In the case of the dispersant used for the pigment dispersion, the residue remaining after the pattern formation of the photosensitive resin composition for color filters is greatly influenced. Therefore, the solubility in the aqueous alkali solution used as a developer in the production of pigment dispersion is an important problem. Therefore, when using a dispersant having an acidic group such as a carboxyl group or a phosphoric acid group, the residue can be improved. Therefore, in the present invention, in order to use such a dispersant, it is possible to interact with an acidic group such as a carboxyl group or a phosphoric acid group, and to secure dispersion and stability by using a pigment derivative including an amino group having a structure similar to the pigment to be dispersed.
이하, 각 구성 성분에 대하여 상세히 설명하도록 한다.Hereinafter, each component will be described in detail.
(A) 안료유도체(A) Pigment derivative
상기 안료유도체는 아미노기를 포함하는 디케토피롤로피롤계 화합물을 사용할 수 있다. 이러한 안료유도체는 말단에 아미노기를 가지고 있으므로, 산성 관능기를 갖는 분산제와 상호작용하여 분산을 가능하게 한다. 즉, 종래에 사용되는 C. I. Red254 등의 적색 디케토피롤로피롤계 안료와 구조가 비슷하므로 안료와는 π-orbital 등의 상호작용을 할 수 있다.The pigment derivative may be a diketopyrrolopyrrole compound containing an amino group. Since such pigment derivatives have amino groups at their ends, they interact with dispersants having acidic functional groups to enable dispersion. That is, since the structure is similar to the conventional red diketopyrrolopyrrole pigments such as C. I. Red254, it is possible to interact with the pigment such as π-orbital.
바람직하게는, 상기 안료유도체로는 하기 화학식 1로 표현되는 화합물을 사용하는 것이 좋다.Preferably, as the pigment derivative, it is preferable to use a compound represented by the following Chemical Formula 1.
[화학식 1][Formula 1]
상기 화학식 1에서,In
상기 X1 및 X2는 동일하거나 서로 상이하며, 각각 독립적으로 할로겐, 치환 된 또는 비치환된 알킬기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 아릴알킬기, 치환 또는 비치환된 사이클로알킬기, 치환 또는 비치환된 헤테로사이클로알킬기, 치환 또는 비치환된 사이클로알케닐기, 치환 또는 비치환된 사이클로알키닐기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 알킬 아미노기, 치환 또는 비치환된 알콕시 아미노기, 및 치환 또는 비치환된 알칸올기로 이루어진 군에서 선택되는 것일 수 있으며, 보다 바람직하게는 할로겐, 치환 또는 비치환된 알킬기, 및 치환 또는 비치환된 아릴알킬기로 이루어진 군에서 선택되는 것일 수 있다. X 1 and X 2 are the same or different from each other, and each independently a halogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, Substituted or unsubstituted heteroaryl group, arylalkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted cycloalkenyl group, substituted or unsubstituted cycloalkynyl group, substituted or unsubstituted It may be selected from the group consisting of a substituted alkoxy group, a substituted or unsubstituted alkyl amino group, a substituted or unsubstituted alkoxy amino group, and a substituted or unsubstituted alkanol group, more preferably halogen, substituted or unsubstituted It may be selected from the group consisting of an alkyl group, and a substituted or unsubstituted arylalkyl group.
상기 Ar은 치환 또는 비치환된 아릴렌기이고, 바람직하게는 치환 또는 비치환된 페닐렌, 나프탈렌, 및 안트라센으로 이루어진 군에서 선택될 수 있다.Ar is a substituted or unsubstituted arylene group, and may be preferably selected from the group consisting of substituted or unsubstituted phenylene, naphthalene, and anthracene.
상기 R1 내지 R4는 동일하거나 서로 상이하며, 각각 독립적으로 수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알콕시, 및 치환 또는 비치환된 아릴알킬기로 이루어진 군에서 선택되는 것일 수 있다.R 1 to R 4 are the same or different from each other, and each independently may be selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy, and a substituted or unsubstituted arylalkyl group.
m1 및 m2는 각각 독립적으로 1 내지 20의 정수이고, m 1 and m 2 are each independently an integer of 1 to 20,
R5 내지 R8는 동일하거나 서로 상이하며, 서로 독립적으로 치환 또는 비치환된 아미노기, -SR10, 및 -OR10로 이루어진 군에서 선택되는 것일 수 있으며, R10은 수소, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴알킬기, 술폰산, 및 술폰아미노기로 이루어진 군에서 선택되는 것일 수 있 으며, 이때 R5 내지 R8 중에서 적어도 하나는 반드시 치환 또는 비치환된 아미노기이다.R 5 to R 8 are the same or different from each other, and independently from each other may be selected from the group consisting of a substituted or unsubstituted amino group, -SR 10 , and -OR 10 , R 10 is hydrogen, substituted or unsubstituted It may be selected from the group consisting of an amino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylalkyl group, sulfonic acid, and sulfonamino group, wherein at least one of R 5 to R 8 is necessarily substituted or unsubstituted amino group to be.
상기 R5 내지 R8의 바람직한 예로는 하기 화학식 2로 표현되는 화합물을 들 수 있다.Preferred examples of the R 5 to R 8 include a compound represented by the following formula (2).
[화학식 2][Formula 2]
상기 화학식 2에서,In
A는 NR15, -O-, 및 -S-로 이루어진 군에서 선택되는 것일 수 있으며, 이때, R15는 수소, 치환 또는 비치환된 알킬기, 및 치환 또는 비치환된 아릴알킬기로 이루어진 군에서 선택되는 것일 수 있고,A may be selected from the group consisting of NR 15 , -O-, and -S-, wherein R 15 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted arylalkyl group. Could be,
상기 R11 및 R12는 동일하거나 서로 상이하며, 각각 독립적으로, 수소, 치환 또는 비치환된 알킬기, 할로겐, 치환 또는 비치환된 알콕시기, 및 치환 또는 비치환된 아릴알킬기로 이루어진 군에서 선택되는 것일 수 있고,R 11 and R 12 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a halogen, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted arylalkyl group. Can be,
상기 R13 및 R14는 동일하거나 서로 상이하며, 각각 독립적으로, 수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 치환 또는 비 치환된 아릴알킬기, 치환 또는 비치환된 사이클로알킬기, 치환 또는 비치환된 헤테로사이클로알킬기, 치환 또는 비치환된 사이클로알케닐기, 치환 또는 비치환된 사이클로알키닐기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 알킬 아미노기, 치환 또는 비치환된 알콕시 아미노기, 및 치환 또는 비치환된 알칸올기로 이루어진 군에서 선택되는 것일 수 있으며, 보다 바람직하게는 수소, 치환 또는 비치환된 알킬기, 및 치환 또는 비치환된 아릴알킬기로 이루어진 군에서 선택되는 것일 수 있으며, R 13 above And R 14 are the same or different from each other, and each independently, hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted Substituted heteroaryl group, substituted or unsubstituted arylalkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted cycloalkenyl group, substituted or unsubstituted cycloalkynyl group, substituted Or an unsubstituted alkoxy group, a substituted or unsubstituted alkyl amino group, a substituted or unsubstituted alkoxy amino group, and a substituted or unsubstituted alkanol group, and more preferably hydrogen, substituted or unsubstituted. It may be selected from the group consisting of a substituted alkyl group, and a substituted or unsubstituted arylalkyl group,
상기 m3는 1 내지 20의 정수이다.M <3> is an integer of 1-20.
상기 R5 내지 R8은 모두 치환 또는 비치환된 아미노기인 것이 더욱더 바람직하다.It is still more preferable that R 5 to R 8 are all substituted or unsubstituted amino groups.
상기 안료유도체는 컬러 필터용 감광성 수지 조성물 중 0.1 내지 10 중량%로 포함되는 것이 바람직하고, 0.2 내지 5 중량%로 포함되는 것이 보다 바람직하다. 상기 범위에서는 색 표현이 효과적으로 일어나면서, 적절한 점도를 유지할 수 있어, 이 조성물을 제품 적용시 광학적, 물리적, 화학적 품질이 우수한 장점이 있다.The pigment derivative is preferably included in 0.1 to 10% by weight, more preferably in 0.2 to 5% by weight of the photosensitive resin composition for color filters. In the above range, while the color expression occurs effectively, it is possible to maintain the appropriate viscosity, there is an advantage in that the optical, physical, chemical quality when applying the composition to the product.
(B) 안료(B) pigment
상기 안료로는 안트라퀴논계 안료, 페릴렌계 등의 축합다환 안료, 프탈로시아닌 안료, 또는 아조계 안료 등의 유기안료 이외에 카본블랙 등의 무기안료도 사용할 수 있다.As the pigment, inorganic pigments such as carbon black may be used in addition to organic pigments such as anthraquinone pigments, condensed polycyclic pigments such as perylenes, phthalocyanine pigments, or azo pigments.
상기 유기안료로서는, 컬러 인덱스(Color Index)에 안료로서 분류된 화합물을 구체적인 예로 들 수 있다. 상기 컬러 인텍스에 안료로서 분류된 화합물의 구체적인 예로는, C.I. 안료 황색 1호, C.I. 안료 황색 12호, C.I. 안료 황색 13호, C.I. 안료 황색 14호, C.I. 안료 황색 15호, C.I. 안료 황색 16호, C.I. 안료 황색 17호, C.I. 안료 황색 20호, C.I. 안료 황색 24호, C.I. 안료 황색 31호, C.I. 안료 황색 53호, C.I. 안료 황색 83호, C.I. 안료 황색 86호, C.I. 안료 황색 93호, C.I. 안료 황색 94호, C.I. 안료 황색 109호, C.I. 안료 황색 110호, C.I. 안료 황색 117호, C.I. 안료 황색 125호, C.I. 안료 황색 128호, C.I. 안료 황색 137호, C.I. 안료 황색 138호, C.I. 안료 황색 139호, C.I. 안료 황색 147호, C.I. 안료 황색 148호, C.I. 안료 황색 150호, C.I. 안료 황색 153호, C.I. 안료 황색 154호, C.I. 안료 황색 166호, 또는 C.I. 안료 황색 173호 등을 들 수 있다.As said organic pigment, the compound classified as a pigment in a color index can be mentioned concretely. Specific examples of the compounds classified as pigments in the color index are C.I. Pigment Yellow No. 1, C.I. Pigment Yellow No. 12, C.I. Pigment Yellow No. 13, C.I. Pigment Yellow No. 14, C.I. Pigment Yellow No. 15, C.I. Pigment Yellow No. 16, C.I. Pigment Yellow No. 17, C.I. Pigment Yellow No. 20, C.I. Pigment Yellow No. 24, C.I. Pigment Yellow No. 31, C.I. Pigment Yellow No. 53, C.I. Pigment Yellow No. 83, C.I. Pigment Yellow No. 86, C.I. Pigment Yellow 93, C.I. Pigment Yellow No. 94, C.I. Pigment Yellow No. 109, C.I. Pigment Yellow No. 110, C.I. Pigment Yellow No. 117, C.I. Pigment Yellow No. 125, C.I. Pigment Yellow No. 128, C.I. Pigment Yellow 137, C.I. Pigment Yellow 138, C.I. Pigment Yellow No. 139, C.I. Pigment Yellow No. 147, C.I. Pigment Yellow 148, C.I. Pigment Yellow No. 150, C.I. Pigment Yellow 153, C.I. Pigment Yellow 154, C.I. Pigment yellow 166, or C.I. Pigment yellow 173 etc. are mentioned.
또한, 상기 컬러 인텍스에 안료로서 분류된 화합물의 구체적인 예로는, C.I. 안료 오렌지색 13호, C.I. 안료 오렌지색 31호, C.I. 안료 오렌지색 36호, C.I. 안료 오렌지색 38호, C.I. 안료 오렌지색 40호, C.I. 안료 오렌지색 42호, C.I. 안료 오렌지색 43호, C.I. 안료 오렌지색 51호, C.I. 안료 오렌지색 55호, C.I. 안료 오렌지색 59호, C.I. 안료 오렌지색 61호, C.I. 안료 오렌지색 64호, C.I. 안료 오렌지색 65호, C.I. 안료 오렌지색 71호, 또는 C.I. 안료 오렌지색 73호 등을 들 수 있다.In addition, specific examples of the compounds classified as pigments in the color index, C.I. Pigment Orange No. 13, C.I. Pigment Orange No. 31, C.I. Pigment Orange No. 36, C.I. Pigment Orange No. 38, C.I. Pigment Orange No. 40, C.I. Pigment Orange No. 42, C.I. Pigment Orange No. 43, C.I. Pigment Orange No. 51, C.I. Pigment Orange No. 55, C.I. Pigment Orange No. 59, C.I. Pigment Orange No. 61, C.I. Pigment Orange 64, C.I. Pigment Orange 65, C.I. Pigment Orange 71, or C.I. Pigment orange 73, etc. are mentioned.
또한, 상기 컬러 인텍스에 안료로서 분류된 화합물의 구체적인 예로는, C.I. 안료 적색 9호, C.I. 안료 적색 97호, C.I. 안료 적색 105호, C.I. 안료 적색 122 호, C.I. 안료 적색 123호, C.I. 안료 적색 144호, C.I. 안료 적색 149호, C.I. 안료 적색 166호, C.I. 안료 적색 168호, C.I. 안료 적색 176호, C.I. 안료 적색 177호, C.I. 안료 적색 180호, C.I. 안료 적색 192호, C.I. 안료 적색 215호, C.I. 안료 적색 216호, C.I. 안료 적색 224호, C.I. 안료 적색 242호, C.I. 안료 적색 254호, C.I. 안료 적색 264호, 또한 C.I. 안료 적색 265호 등을 들 수 있다. In addition, specific examples of the compounds classified as pigments in the color index, C.I. Pigment Red No. 9, C.I. Pigment Red No. 97, C.I. Pigment Red No. 105, C.I. Pigment Red No. 122, C.I. Pigment Red 123, C.I. Pigment Red 144, C.I. Pigment Red 149, C.I. Pigment Red 166, C.I. Pigment Red 168, C.I. Pigment Red 176, C.I. Pigment Red No. 177, C.I. Pigment Red No. 180, C.I. Pigment Red 192, C.I. Pigment Red 215, C.I. Pigment Red 216, C.I. Pigment Red 224, C.I. Pigment Red 242, C.I. Pigment Red No. 254, C.I. Pigment Red No. 264, as well as C.I. Pigment red 265, etc. are mentioned.
또한, 상기 컬러 인텍스에 안료로서 분류된 화합물의 구체적인 예로는, C.I. 안료 청색 15호, C.I. 안료 청색 15:3호, C.I. 안료 청색 15:4호, C.I. 안료 청색 15:6호, 또는 C.I. 안료 청색 60호 등을 들 수 있다.In addition, specific examples of the compounds classified as pigments in the color index, C.I. Pigment Blue No. 15, C.I. Pigment Blue 15: 3, C.I. Pigment Blue 15: 4, C.I. Pigment blue 15: 6, or C.I. Pigment blue 60, etc. are mentioned.
또한, 상기 컬러 인텍스에 안료로서 분류된 화합물의 구체적인 예로는, C.I. 안료 자주색 1호, C.I. 안료 자주색 19호, C.I. 안료 자주색 23호, C.I 안료 자주색 29호, C.I 안료 자주색 32호, C.I 안료 자주색 36호, 또는 C.I 안료 자주색 38호 등을 들 수 있다.In addition, specific examples of the compounds classified as pigments in the color index, C.I. Pigment Purple No. 1, C.I. Pigment Purple No. 19, C.I. Pigment Purple No. 23, C.I Pigment Purple No. 29, C.I Pigment Purple No. 32, C.I Pigment Purple No. 36, or C.I Pigment Purple No. 38 and the like.
또한, 상기 컬러 인텍스에 안료로서 분류된 화합물의 구체적인 예로는, C.I. 안료 녹색 7호, C.I. 또는 안료 녹색 36호 등을 들 수 있다.In addition, specific examples of the compounds classified as pigments in the color index, C.I. Pigment Green No. 7, C.I. Or pigment green 36.
또한, 상기 컬러 인텍스에 안료로서 분류된 화합물의 구체적인 예로는, C.I. 안료 갈색 23호, 또는 C.I. 안료 갈색 25호 등을 들 수 있다. In addition, specific examples of the compounds classified as pigments in the color index, C.I. Pigment Brown 23, or C.I. Pigment brown No. 25, etc. are mentioned.
상기 유기안료는 각각 단독으로 또는 2종 이상의 조합으로 사용할 수 있다.The organic pigments may be used alone or in combination of two or more.
상기 무기안료로는 산화티탄, 티탄블랙, 또는 카본블랙 등을 사용할 수 있다. Titanium oxide, titanium black, carbon black, or the like may be used as the inorganic pigment.
상기 안료는 컬러 필터용 감광성 수지 조성물 중 1 내지 30 중량%로 포함되 는 것이 바람직하고, 5 내지 15 중량%로 포함되는 것이 보다 바람직하다. 상기 범위에서는 우수한 색 재현율을 구현할 수 있고, 패턴의 경화특성 및 밀착특성이 우수하여 바람직하다. The pigment is preferably included in 1 to 30% by weight of the photosensitive resin composition for color filters, more preferably contained in 5 to 15% by weight. In the above range, it is possible to implement an excellent color reproducibility, excellent curing properties and adhesion properties of the pattern is preferred.
(C) (C) 분산제Dispersant
상기 분산제로는 하기 화학식 3 또는 4와 같이 인산기 또는 카르복실산기를 포함하고, 알칼리 수용액에 용해될 수 있는 분산제를 사용하는 것이 바람직하다. 이러한 분산제를 사용하면 노광 및 현상 후 잔사가 없는 패턴을 형성할 수 있다.As the dispersant, it is preferable to use a dispersant containing a phosphoric acid group or a carboxylic acid group as shown in the following Chemical Formula 3 or 4, and soluble in an aqueous alkali solution. Using such a dispersant can form a pattern free of residue after exposure and development.
[화학식 3](3)
상기 화학식 3에서, In Chemical Formula 3,
R16 및 R17은 동일하거나 서로 상이하며, 각각 독립적으로, 치환된 또는 비치환된 알킬기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 아릴기, 치환 또는 비치환된 헤테로아릴기, 아릴알킬기, 치환 또는 비치환된 사이클로알킬기, 폴리에틸렌옥시, 치환 또는 비치환된 헤테로사이클로알킬기, 치환 또는 비치환된 사이클로알케닐기, 치환 또는 비치환된 사이클로알키닐기, 치환 또는 비치환된 알콕시, 알킬 아미노기, 알콕시 아미노기, 및 치환 또는 비치환된 알칸올기로 이루어진 군에서 선택되는 것일 수 있다.R 16 and R 17 are the same or different from each other, and each independently, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or Unsubstituted heteroaryl group, arylalkyl group, substituted or unsubstituted cycloalkyl group, polyethyleneoxy, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted cycloalkenyl group, substituted or unsubstituted cycloalkynyl group, substituted or It may be selected from the group consisting of unsubstituted alkoxy, alkyl amino group, alkoxy amino group, and substituted or unsubstituted alkanol group.
[화학식 4][Formula 4]
상기 화학식 4에서, In Chemical Formula 4,
D는 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치화된 아릴기, 치환 또는 비치환된 헤테로아릴기, 치환 또는 비치환된 아릴알킬기, 치환 또는 비치환된 사이클로알킬기, 치환 또는 비치환된 헤테로사이클로알킬기, 치환 또는 비치환된 사이클로알키닐기, 치환 또는 비치환된 알콕시기, 알킬 아미노기, 알콕시 아미노기, 치환 또는 비치환된 알칸올기, 폴리에틸렌옥시기, 또는 폴리에스테르, 아크릴계수지, 우레탄 수지 등의 중합체일 수 있으며,D is a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted cycloalkyl group , Substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted cycloalkynyl group, substituted or unsubstituted alkoxy group, alkyl amino group, alkoxy amino group, substituted or unsubstituted alkanol group, polyethyleneoxy group, or polyester, acrylic type It may be a polymer such as resin, urethane resin,
m4는 1 내지 10의 정수일 수 있다. m 4 may be an integer from 1 to 10.
또한, 상기 분산제는 다른 모노머들과 폴리에스테르계, 아크릴계, 또는 우레탄계의 중합체가 될 수 있으며, 이때 중량평균분자량(Mw)은 500 내지 30,000인 것이 바람직하다. 사용 가능한 모노머로는 아크릴산, 메타크릴산, 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 프로필(메타)아크릴레이트, 에틸헥실(메타)아크릴레이트, 페닐(메타)아크릴레이트, 아크릴산 벤질(메타)아크릴레이트, 벤질(메타)아크릴레이트, 톨릴(메타)아크릴레이트, o-실릴(메타)아크릴레이트, 글리세롤(메 타)아크릴레이트, 알킬아릴(메타)아크릴레이트, 숙시닉(메타)아크릴레이트 등과 같은 (메타)아크릴레이트계 모노머; 카프로락톤, 부티로락톤 등과 같은 락톤계 모노머 등을 들 수 있으며, 1종 또는 2종 이상 혼합하여 사용할 수 있다.In addition, the dispersant may be a polymer of other monomers and polyester, acrylic, or urethane-based, wherein the weight average molecular weight (Mw) is preferably 500 to 30,000. The monomers that can be used include acrylic acid, methacrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, ethylhexyl (meth) acrylate, phenyl (meth) acrylate, and benzyl acrylate. Meth) acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, o-silyl (meth) acrylate, glycerol (meth) acrylate, alkylaryl (meth) acrylate, succinic (meth) acrylic (Meth) acrylate monomers, such as a rate; Lactone system monomers, such as caprolactone and butyrolactone, etc. are mentioned, It can use 1 type, or 2 or more types in mixture.
상기 분산제는 감광성 수지 조성물 중 0.5 내지 20 중량%로 포함되는 것이 바람직하고, 1 내지 10 중량%로 포함되는 것이 보다 바람직하다. 상기 범위에서는 분산이 효과적으로 일어나고, 분산 안정성을 확보할 수 있으며, 잔사가 없는 패턴을 형성할 수 있고, 적절한 점도를 유지할 수 있으며, 나아가 컬러필터의 광학적, 물리적, 및 화학적 품질을 향상시킬 수 있다. The dispersant is preferably contained in 0.5 to 20% by weight, more preferably in 1 to 10% by weight of the photosensitive resin composition. In the above range, dispersion can effectively occur, dispersion stability can be ensured, a pattern free of residue can be formed, an appropriate viscosity can be maintained, and further, optical, physical, and chemical quality of the color filter can be improved.
(D) 바인더 수지(D) binder resin
상기 바인더 수지는 (메타)아크릴 산, 알킬(메타)아크릴레이트, 아릴(메타)아크릴레이트, 알코올(메타)아크릴레이트, 알킬아릴 (메타)아크릴레이트, 숙시닉(메타)아크릴레이트, 스티렌 등을 모노머로 하는 (메타)아크릴레이트계 공중합체 수지 등을 들 수 있으며, 이들을 1종 또는 2종 이상 혼합하여 사용할 수 있다. The binder resin may be (meth) acrylic acid, alkyl (meth) acrylate, aryl (meth) acrylate, alcohol (meth) acrylate, alkylaryl (meth) acrylate, succinic (meth) acrylate, styrene or the like. (Meth) acrylate type copolymer resin etc. which make a monomer are mentioned, These can be used 1 type or in mixture of 2 or more types.
구체적으로 아크릴산, 메타크릴산, 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 프로필(메타)아크릴레이트, 에틸헥실(메타)아크릴레이트, 페닐(메타)아크릴레이트, 아크릴산 벤질(메타)아크릴레이트, 벤질(메타)아크릴레이트, 톨릴(메타)아크릴레이트, o-실릴(메타)아크릴레이트, 글리세롤(메타)아크릴레이트, 알킬아릴(메타)아크릴레이트, 숙시닉(메타)아크릴레이트 등을 모노머로 하는 아크릴레이트계 공중합체 수지 등을 들 수 있으며, 이들을 1종 또는 2종 이상 혼합하여 사용 할 수 있다. Specifically, acrylic acid, methacrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, ethylhexyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylic acid Monomers such as acrylate, benzyl (meth) acrylate, tolyl (meth) acrylate, o-silyl (meth) acrylate, glycerol (meth) acrylate, alkylaryl (meth) acrylate, succinic (meth) acrylate, and the like. An acrylate copolymer resin etc. can be mentioned, These can be used 1 type or in mixture of 2 or more types.
상기 바인더 수지는 컬러 필터용 감광성 수지 조성물 중 1 내지 30 중량%로 포함되는 것이 바람직하다. 상기 범위에서는 분산이 효과적으로 일어나고, 분산 안정성을 확보할 수 있으며, 적절한 점도를 유지하여 제품 적용시 광학적, 물리적, 화학적 품질이 우수한 장점이 있어 바람직하다. The binder resin is preferably contained in 1 to 30% by weight of the photosensitive resin composition for color filters. In the above range, dispersion is effectively performed, dispersion stability can be secured, and an optical, physical, and chemical quality is excellent in applying a product by maintaining an appropriate viscosity.
(E) (E) 광중합Photopolymerization 개시제Initiator
상기 광중합 개시제는 감광성 수지 조성물에 일반적으로 사용되는 광중합 개시제를 사용할 수 있으며, 예를 들면, 아세토페논계 화합물, 벤조페논계 화합물, 티오크산톤계 화합물, 벤조인계 화합물, 트리아진계 화합물, 옥심계 화합물, 및 이들의 조합 등을 사용할 수 있다. The photopolymerization initiator may be a photopolymerization initiator generally used in the photosensitive resin composition, for example, acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, oxime compounds , And combinations thereof may be used.
상기 아세토페논계의 화합물로는 2,2'-디에톡시아세토페논, 2,2'-디부톡시아세토페논, 2-히드록시-2-메틸플루오로페논, p-t-부틸트리클로로아세토페논, p-t-부틸디클로로아세토페논, 4-클로로아세토페논, 2,2'-디클로로-4-페녹시아세토페논, 2-메틸-1-(4-(메틸티오)페닐)-2-모폴리노프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-모폴리노페닐)-부탄-1-온 등을 사용할 수 있다. Examples of the acetophenone compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylfluorophenone, pt-butyltrichloroacetophenone, and pt- Butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1- On, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one and the like can be used.
상기 벤조페논계 화합물로는 벤조페논, 벤조일 안식향산, 벤조일 안식향산 메틸, 4-페닐 벤조페논, 히드록시 벤조페논, 아크릴화 벤조페논, 4,4'-비스(디메틸아미노)벤조페논, 4,4'-비스(디에틸아미노) 벤조페논, 4,4'-디메틸아미노벤조페논, 4,4'-디클로로벤조페논, 3,3'-디메틸-2-메톡시벤조페논 등을 사용할 수 있다. Examples of the benzophenone compounds include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, and 4,4'-. Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone and the like can be used.
상기 티오크산톤계 화합물로는 티오크산톤, 2-메틸티오크산톤, 이소프로필 티오크산톤, 2,4-디에틸 티오크산톤, 2,4-디이소프로필 티오크산톤, 2-클로로티오크산톤 등을 사용할 수 있다. Examples of the thioxanthone compound include thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone and 2-chlorothione. Orcanthone etc. can be used.
상기 벤조인계 화합물로는 벤조인, 벤조인 메틸 에테르, 벤조인 에틸 에테르, 벤조인 이소프로필 에테르, 벤조인 이소부틸 에테르, 벤질디메틸케탈 등을 사용할 수 있다. As the benzoin-based compound, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal and the like can be used.
상기 트리아진계 화합물로는 2,4,6,-트리클로로 s-트리아진, 2-페닐 4,6-비스(트리클로로메틸)-s-트리아진, 2-(3',4'-디메톡시스티릴)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(4'-메톡시나프틸)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(p-메톡시페닐)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(p-톨릴)-4,6-비스(트리클로로메틸)-s-트리아진, 2-비페닐 4,6-비스(트리클로로메틸)-s-트리아진, 비스(트리클로로메틸)-6-스티릴 s-트리아진, 2-(나프토1-일)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(4-메톡시나프토1-일)-4,6-비스(트리클로로메틸)-s-트리아진, 2-4-트리클로로 메틸(피페로닐)-6-트리아진, 2-4-트리클로로 메틸(4'-메톡시스티릴)-6-트리아진, 2-피페로니로-4,6-비스(트리클로로메틸)-1,3,5-트리아진 등을 사용할 수 있다.Examples of the triazine compounds include 2,4,6, -trichloro s-triazine, 2-phenyl 4,6-bis (trichloromethyl) -s-triazine, and 2- (3 ', 4'-dimethoxy Styryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2- Biphenyl 4,6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl s-triazine, 2- (naphtho1-yl) -4,6-bis ( Trichloromethyl) -s-triazine, 2- (4-methoxynaphtho1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2-4-trichloro methyl (pipero Yl) -6-triazine, 2-4-trichloro methyl (4'-methoxystyryl) -6-triazine, 2-piperoniro-4,6-bis (trichloromethyl) -1,3 , 5-triazine and the like can be used.
상기 옥심계 화합물로는 2-(o-벤조일옥심)-1-[4-(페닐티오)페닐]-1,2-옥탄디온 및 1-(o-아세틸옥심)-1-[9-에틸-6-(2-메틸벤조일)-9H-카르바졸-3-일]에탄온 등을 사용할 수 있따.Examples of the oxime compound include 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione and 1- (o-acetyloxime) -1- [9-ethyl- 6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone and the like can be used.
상기 광중합 개시제 이외에, 카바졸계 화합물, 디케톤류 화합물, 설포늄 보 레이트계 화합물, 디아조계, 비이미다졸계 화합물 등도 광중합 개시제로 사용할 수 있다. In addition to the photoinitiator, a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, a biimidazole compound, and the like can also be used as the photopolymerization initiator.
상기 광중합 개시제는 컬러 필터용 감광성 수지 조성물 중 0.01 내지 5 중량%로 포함되는 것이 바람직하고, 0.05 내지 3 중량%로 포함하는 것이 보다 바람직하다.상기 범위에서는 조성물의 감도가 우수하여 물리적 및 광학적 특성이 우수한 장점이 있다. The photopolymerization initiator is preferably included in 0.01 to 5% by weight of the photosensitive resin composition for color filters, more preferably in 0.05 to 3% by weight. In the above range, the sensitivity of the composition is excellent and the physical and optical properties are There is an excellent advantage.
(F) (F) 광중합성Photopolymerizable 모노머Monomer
상기 광중합성 모노머로는 2개 이상의 히드록시기를 갖는 다관능기 모노머를 사용할 수 있다. As the photopolymerizable monomer, a polyfunctional monomer having two or more hydroxyl groups can be used.
구체적으로는 글리세롤(메타)아크릴레이트, 펜타에리트리톨 헥사(메타)아크릴레이트, 에틸렌글리콜디(메타)아크릴레이트, 트리에틸렌글리콜디(메타)아크릴레이트, 1,4-부탄디올디(메타)아크릴레이트, 1,6-헥산디올디(메타)아크릴레이트, 네오펜틸글리콜디(메타)아크릴레이트, 펜타에리트리톨 디(메타)아크릴레이트, 펜타에리트리톨 트리(메타)아크릴레이트, 디펜타에리트리톨 트리(메타)아크릴레이트, 디펜타에리트리톨(메타)아크릴레이트, 비스페놀 A 디(메타)아크릴레이트, 트리메틸롤프로판트리(메타)아크릴레이트, 노볼락에폭시(메타)아크릴레이트, 디에틸렌글리콜디(메타)아크릴레이트, 프로필렌글리콜디(메타)아크릴레이트 등을 들 수 있다. Specifically, glycerol (meth) acrylate, pentaerythritol hexa (meth) acrylate, ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate , 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tri ( Meta) acrylate, dipentaerythritol (meth) acrylate, bisphenol A di (meth) acrylate, trimethylolpropane tri (meth) acrylate, novolac epoxy (meth) acrylate, diethylene glycol di (meth) Acrylate, propylene glycol di (meth) acrylate, etc. are mentioned.
상기 광중합 모노머는 컬러 필터용 감광성 수지 조성물 중 1 내지 80 중량%로 포함되는 것이 바람직하고, 5 내지 50 중량%로 포함되는 것이 보다 바람직하다. 상기 범위에서는, 노광 후 패턴을 잘 유지하면서 적절한 점도를 유지할 수 있고, 노광 후 잔사가 거의 없어 원하는 크기의 패턴을 얻을 수 있다. 따라서, 제품에 적용 시 물리적 및 광학적 특성이 우수한 장점이 있다. The photopolymerization monomer is preferably contained in 1 to 80% by weight, more preferably 5 to 50% by weight of the photosensitive resin composition for color filters. In the above range, an appropriate viscosity can be maintained while maintaining the post-exposure pattern well, and there is almost no post-exposure residue, so that a pattern having a desired size can be obtained. Therefore, when applied to the product has the advantage of excellent physical and optical properties.
(G) 용매(G) solvent
상기 용매는 특별히 국한되지 않으며, 컬러필터용 감광성 수지 조성물의 용매로서 공지된 것 중에서 단독 또는 2종 이상을 혼합하여 사용할 수 있다. 예를 들면 메탄올, 에탄올 등의 알코올류; 디클로로에틸 에테르, n-부틸 에테르, 디이소아밀 에테르, 메틸페닐 에테르, 테트라히드로푸란 등의 에테르류; 에틸렌 글리콜 모노메틸에테르, 에틸렌 글리콜 모노에틸에테르 등의 글리콜 에테르류; 메틸 셀로솔브 아세테이트, 에틸 셀로솔브 아세테이트, 디에틸 셀로솔브 아세테이트 등의 셀로솔브 아세테이트류; 메틸에틸 카르비톨, 디에틸 카르비톨, 디에틸렌 글리콜 모노메틸에테르, 디에틸렌 글리콜 모노에틸에테르, 디에틸렌 글리콜 디메틸에테르, 디에틸렌 글리콜 메틸에틸에테르, 디에틸렌 글리콜 디에틸에테르 등의 카르비톨류; 프로필렌글리콜메틸에틸아세테이트, 프로필렌 글리콜 메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류; 톨루엔, 크실렌 등의 방향족 탄화수소류; 메틸에틸케톤, 시클로헥사논, 4-히드록시-4-메틸-2-펜타논, 메틸-n-프로필케톤, 메틸-n-부틸케논, 메틸-n-아밀케톤, 2-헵타논 등의 케톤류; 초산 에틸, 초산-n-부틸, 초산 이소부틸 등의 포화 지방족 모노카르복실산 알킬 에스테르류; 젖산 메틸, 젖산 에틸 등의 젖산 에스테르류; 옥 시 초산 메틸, 옥시 초산 에틸, 옥시 초산 부틸 등의 옥시 초산 알킬 에스테르류; 메톡시 초산 메틸, 메톡시 초산 에틸, 메톡시 초산 부틸, 에톡시 초산 메틸, 에톡시 초산 에틸 등의 알콕시 초산 알킬 에스테르류; 3-옥시 프로피온산 메틸, 3-옥시 프로피온산 에틸 등의 3-옥시 프로피온산 알킬에스테르류; 3-메톡시 프로피온산 메틸, 3-메톡시 프로피온산 에틸, 3-에톡시 프로피온산 에틸, 3-에톡시 프로피온산 메틸 등의 3-알콕시 프로피온산 알킬 에스테르류; 2-옥시 프로피온산 메틸, 2-옥시 프로피온산 에틸, 2-옥시 프로피온산 프로필 등의 2-옥시 프로피온산 알킬 에스테르류; 2-메톡시 프로피온산 메틸, 2-메톡시 프로피온산 에틸, 2-에톡시 프로피온산 에틸, 2-에톡시 프로피온산 메틸 등의 2-알콕시 프로피온산 알킬 에스테르류; 2-옥시-2-메틸 프로피온산 메틸, 2-옥시-2-메틸 프로피온산 에틸 등의 2-옥시-2-메틸 프로피온산 에스테르류; 2-메톡시-2-메틸 프로피온산 메틸, 2-에톡시-2-메틸 프로피온산 에틸 등의 2-알콕시-2-메틸 프로피온산 알킬류의 모노옥시 모노카르복실산 알킬 에스테르류; 2-히드록시 프로피온산 에틸, 2-히드록시-2-메틸 프로피온산 에틸, 히드록시 초산 에틸, 2-히드록시-3-메틸 부탄산 메틸 등의 에스테르류; 피루빈산 에틸 등의 케톤산 에스테르류 등의 화합물이 있으며, 또한, N-메틸포름아미드, N,N-디메틸포름아미드, N-메틸포름아닐라드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드, 벤질에틸에테르, 디헥실에테르, 아세트닐아세톤, 이소포론, 카프론산, 카프릴산, 1-옥탄올, 1-노난올, 벤질알코올, 초산 벤질, 안식향산 에틸, 옥살산 디에틸, 말레인산 디에틸, γ-부티로락톤, 탄산 에틸렌, 탄산 프로필렌, 페닐 셀로솔브 아세테이트 등이 있다. The said solvent is not specifically limited, It can use individually or in mixture of 2 or more types from what is known as a solvent of the photosensitive resin composition for color filters. Alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ethyl acetate, propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butylkenone, methyl-n-amyl ketone and 2-heptanone ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxy acetic acid alkyl esters such as methyl methyl acetate, oxy ethyl acetate and oxy butyl acetate; Alkoxy acetate alkyl esters, such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxy propionic acid alkyl esters such as methyl 3-oxy propionate and ethyl 3-oxypropionate; 3-alkoxy propionic acid alkyl esters such as 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy ethyl propionate and 3-ethoxy methyl propionate; 2-oxy propionic acid alkyl esters such as 2-oxy methyl propionate, 2-oxy ethyl propionate and 2-oxy propionic acid propyl; 2-alkoxy propionic acid alkyl esters such as 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-ethoxy ethyl propionate and 2-ethoxy methyl propionate; 2-oxy-2-methyl propionic acid esters, such as methyl 2-oxy-2-methyl propionate and ethyl 2-oxy-2-methyl propionate; Monooxy monocarboxylic acid alkyl esters of alkyl 2-alkoxy-2-methyl propionic acids such as methyl 2-methoxy-2-methyl propionate and ethyl 2-ethoxy-2-methyl propionate; Esters such as 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate, and 2-hydroxy-3-methyl butanoate; And compounds such as ketone acid esters such as ethyl pyruvate, and N-methylformamide, N, N-dimethylformamide, N-methylformanilade, N-methylacetamide, and N, N-dimethyl Acetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetyl acetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, acetic acid Benzyl, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, and the like.
이들 용매 중에서 상용성 및 반응성이 우수한 점에서 에틸렌 글리콜 모노에틸 에테르 등의 글리콜 에테르류; 에틸 셀로솔브 아세테이트 등의 셀로솔브 아세테이트류; 2-히드록시 프로피온산 에틸 등의 에스테르류; 디에틸렌 글리콜 모노메틸 에테르 등의 카르비톨류; 프로필렌 글리콜 메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류가 보다 바람직하다.Glycol ethers such as ethylene glycol monoethyl ether in view of excellent compatibility and reactivity among these solvents; Cellosolve acetates such as ethyl cellosolve acetate; Esters such as 2-hydroxy ethyl propionate; Carbitols such as diethylene glycol monomethyl ether; More preferable are propylene glycol alkylether acetates such as propylene glycol methylether acetate and propylene glycol propylether acetate.
상기 용매의 사용량은 특별히 한정되지는 않으며, 색소, 바인더 수지, 광중합개시제 및 광중합성 모노머 사용량에 따라 적절하게 조절할 수 있는 잔부량이면 되나, 바람직하게는 컬러필터용 감광성 수지 조성물 중 10 내지 90 중량%, 보다 바람직하게는 50 내지 80 중량%로 포함하는 것이 좋다. 용매의 함량이 10 내지 90 중량% 인 경우에는, 보다 적절한 점도를 유지할 수 있고, 제품에 적용 시 물리적, 광학적 특성이 보다 향상될 수 있어 바람직하다. The amount of the solvent is not particularly limited, and the amount of the solvent may be appropriately adjusted according to the amount of the dye, the binder resin, the photopolymerization initiator and the photopolymerizable monomer, but preferably 10 to 90% by weight of the photosensitive resin composition for color filters. More preferably 50 to 80% by weight. When the content of the solvent is 10 to 90% by weight, a more suitable viscosity can be maintained, and when applied to a product, physical and optical properties can be further improved, which is preferable.
(H) 기타 첨가제(H) other additives
상기 컬러 필터용 감광성 수지 조성물은 상기 (A) 내지 (G)의 구성 성분들과 함께, 코팅시 얼룩, 반점 생성 방지, 레벨링 조절, 또는 미현상에 의한 잔사의 생성을 방지하기 위하여 기타 첨가제를 더욱 포함할 수 있다.The photosensitive resin composition for the color filter together with the constituents of (A) to (G), in addition to the other additives to prevent staining, spot formation prevention, leveling control, or the generation of residue by undeveloped during coating. It may include.
상기 기타 첨가제의 예로는 말론산, 3-아미노-1,2-프로판디올, 비닐기 또는 (메트)아크릴옥시기를 갖는 실란계 커플링제, 불소계 계면 활성제, 에폭시 수지, 및 이들의 조합 등을 들 수 있다. 이들 첨가제의 사용량은 원하는 물성에 따라 용 이하게 조절될 수 있다.Examples of the other additives include malonic acid, 3-amino-1,2-propanediol, a silane coupling agent having a vinyl group or a (meth) acryloxy group, a fluorine-based surfactant, an epoxy resin, a combination thereof, and the like. have. The amount of these additives can be easily adjusted according to the desired physical properties.
또한 본 발명의 감광성 수지 조성물은 밀착력 및 기타 특성의 향상 등을 위해 필요에 따라 에폭시 화합물을 추가로 더 포함할 수 있다. 상기 에폭시 화합물로는 에폭시 노볼락 아크릴 카르복실레이트 수지, 오르토 크레졸 노볼락 에폭시 수지, 페놀 노볼락 에폭시 수지, 테트라 메틸 비-페닐 에폭시 수지, 비스페놀 A형 에폭시 수지, 지환족 에폭시 수지로 이루어진 군으로부터 선택된 1종 이상을 사용할 수 있다. 이때, 에폭시 화합물은 감광성 수지 조성물 100 중량부에 대하여 0.01 내지 5 중량부로 포함되는 것이 바람직하다. 상기 범위에서는, 저장성, 경제적으로 밀착력, 및 기타 특성을 향상시킬 수 있어 바람직하다.In addition, the photosensitive resin composition of the present invention may further include an epoxy compound as needed for the improvement of adhesion and other properties. The epoxy compound is selected from the group consisting of epoxy novolac acrylic carboxylate resin, ortho cresol novolac epoxy resin, phenol novolac epoxy resin, tetramethyl bi-phenyl epoxy resin, bisphenol A type epoxy resin, alicyclic
상기 에폭시 화합물을 더 포함하는 경우 과산화물 개시제 또는 아조비스계 개시제와 같은 라디칼 중합 개시제를 더 포함할 수 있다.When the epoxy compound is further included, a radical polymerization initiator such as a peroxide initiator or an azobis-based initiator may be further included.
본 발명의 일 구현예에 따른 감광성 수지 조성물을 제조하는 방법의 일 예로는, 용매에 광중합 개시제를 용해한 후 1 내지 2시간 동안 상온에서 교반하고, 이어서 바인더 수지 및 광중합성 모노머를 첨가하고 1 내지 2시간 동안 상온에서 교반하고, 얻어진 생성물에 안료유도체를 첨가하여 30분 내지 1시간 동안 상온에서 교반하여 용해시킨 뒤, 2 내지 5회에 걸쳐 여과를 실시하여 불순물을 제거하여 감광성 수지 조성물을 제조하는 방법을 들 수 있으며, 각 성분의 첨가 순서 및 공정 조건은 적절히 변형될 수 있다.As an example of a method of manufacturing the photosensitive resin composition according to an embodiment of the present invention, after dissolving a photopolymerization initiator in a solvent, the mixture is stirred at room temperature for 1 to 2 hours, and then a binder resin and a photopolymerizable monomer are added and then 1 to 2 A method of preparing a photosensitive resin composition by stirring at room temperature for a time, adding a pigment derivative to the obtained product, stirring and dissolving at room temperature for 30 minutes to 1 hour, and then performing filtration over 2 to 5 times to remove impurities. The addition order and process conditions of each component may be suitably modified.
또한, 본 발명의 또 다른 일 구현예에 따르면, 상기 감광성 수지 조성물을 이용하여 제조된 컬러 필터가 제공된다. In addition, according to another embodiment of the present invention, there is provided a color filter manufactured using the photosensitive resin composition.
상기 컬러 필터는 다음과 같은 공정으로 제조될 수 있으나, 이외에도 본 발명의 감광성 수지 조성물을 이용한 다양한 방법으로 컬러필터가 제조될 수 있다.The color filter may be manufactured by the following process, but in addition, the color filter may be manufactured by various methods using the photosensitive resin composition of the present invention.
상기와 같은 구성을 갖는 감광성 수지 조성물을 웨이퍼 위에 스핀 도포, 슬릿 도포, 롤러 도포, 스프레이 도포 등의 적당한 방법을 사용하여, 예를 들면 5,000 내지 8,000 Å의 두께로 도포하고, 도포된 감광성 수지 조성물층에 대하여 컬러 필터에 필요한 패턴을 형성하도록 광을 조사한 후 도포층을 알칼리 현상액으로 처리하여 도포층의 비노광 부분을 용해시킴으로써 컬러 필터에 필요한 패턴을 갖는 컬러 필터를 형성한다. 이때 조사에 사용되는 광원으로서는 예를 들면, 356nm의 I-line 광을 사용할 수 있으나, 이에 한정되는 것은 아니다. The photosensitive resin composition which has the above structure is apply | coated to the thickness of 5,000-8,000 Pa, for example using suitable methods, such as spin coating, slit coating, roller coating, and spray coating on a wafer, and the applied photosensitive resin composition layer was applied. After irradiating light to form a pattern necessary for the color filter, the coating layer is treated with an alkaline developer to dissolve the non-exposed portions of the coating layer to form a color filter having a pattern necessary for the color filter. In this case, as the light source used for irradiation, for example, 356 nm I-line light may be used, but is not limited thereto.
필요한 적색, 녹색 및 청색의 수에 따라 상기 과정을 반복 수행함으로써, 원하는 패턴을 갖는 컬러 필터를 수득할 수 있다. 또한 상기와 같은 제조 과정에서, 현상에 의해 수득된 화상 패턴을 다시 가열하거나 또는 활성선 조사 등에 의해 경화시킴으로써 내크랙성 또는 내용매성 등을 더욱 향상시킬 수 있다. By repeating the above procedure according to the required number of red, green and blue colors, a color filter having a desired pattern can be obtained. In addition, in the manufacturing process as described above, crack resistance or solvent resistance can be further improved by heating the image pattern obtained by development or curing by active ray irradiation or the like.
상기 제조된 컬러 필터는 초미세의 정사각형 모양의 패턴을 갖는 초미세 픽셀로 제조가 가능하다. 이에 따라 본 발명의 컬러 필터용 감광성 수지 조성물로 제조된 컬러 필터는 고해상도를 나타낼 수 있다.The manufactured color filter may be manufactured with ultrafine pixels having an ultrafine square pattern. Accordingly, the color filter made of the photosensitive resin composition for color filters of the present invention may exhibit high resolution.
이하, 실시예를 들어 본 발명에 대하여 더욱 상세하게 설명할 것이나, 하기의 실시예는 본 발명의 바람직한 실시예일 뿐 본 발명이 하기 실시예에 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples, but the following Examples are only preferred examples of the present invention, and the present invention is not limited to the following Examples.
<< 제조예Production Example 1>: 1>: 디케토피롤로피롤계Diketopyrrolopyrrole system 안료유도체의 제조 Preparation of Pigment Derivatives
1-1: 화학식 5의 화합물의 제조1-1: Preparation of the Compound of Formula 5
C.I.적색안료 254(Ciba Specialty社, Irgaphor Red BT-CF) 30 gC.I. Red Pigment 254 (Ciba Specialty, Irgaphor Red BT-CF) 30 g
파라포름알데히드(Aldrich社) 5 g5 g of paraformaldehyde (Aldrich)
황산 (대정화금社) 400 gSulfuric acid 400 g
반응기에 황산을 넣고 교반하며, 상온에서 C.I.적색 안료 254(Irgaphor Red BT-CF)를 천천히 첨가하고, 파라포름알데히드를 투입하였다. 4시간 후, 반응액을 얼음 조각 1kg이 있는 반응기에 투입한 후 교반하였다.Sulfuric acid was added to the reactor and stirred, C.I. red pigment 254 (Irgaphor Red BT-CF) was slowly added at room temperature, and paraformaldehyde was added thereto. After 4 hours, the reaction solution was added to a reactor containing 1 kg of ice cubes and stirred.
반응액이 상온이 되면, 여과 후 물을 사용하여 여과액이 중성이 될 때까지 세척 후 건조하여 하기 화학식 5의 화합물을 제조하였다.When the reaction solution reached room temperature, the mixture was washed with water and washed until the filtrate became neutral and dried to prepare a compound of Formula 5 below.
[화학식 5][Chemical Formula 5]
1-2: 화학식 6의 화합물의 제조1-2: Preparation of Compound of Formula 6
상기 화학식 5의 화합물 10 g10 g of the compound of Formula 5
시아누릭 클로라이드(Adrich社) 8.8 gCyanuric chloride (Adrich) 8.8 g
피리딘(Aldrich社) 3.7 g3.7 g of pyridine (Aldrich)
N,N-디에틸아미노프로필아민(Aldrich社) 18.7 gN, N-diethylaminopropylamine (Aldrich) 18.7 g
디메틸포름아미드(Aldrich社) 100gDimethylformamide (Aldrich) 100g
반응기에 N2를 주입하며 상온에서 디메틸포름아미드 및 화학식 5의 화합물을 첨가하고, 온도를 10℃로 유지하며 시아누릭 클로라이드를 천천히 투입한 후 30분 교반하였다.N 2 was injected into the reactor, dimethylformamide and the compound of formula 5 were added at room temperature, and the temperature was kept at 10 ° C., and cyanuric chloride was slowly added thereto, followed by stirring for 30 minutes.
반응기를 냉각하며 피리딘을 내부 온도 10℃로 유지하며 조금씩 투입한 후 1시간 교반한다. 이어서, 내부 온도를 15℃로 승온시킨 후 N,N-디에틸아미노프로필아민을 25℃ 이하에서 조금씩 투입하고 1시간 동안 교반하였다. 이어서, 반응기의 온도를 60℃로 승온시킨 후, 1시간 동안 교반하였다.The reactor is cooled and the pyridine is kept at an internal temperature of 10 ° C. and slowly added thereto, followed by stirring for 1 hour. Subsequently, after raising the internal temperature to 15 ° C., N, N-diethylaminopropylamine was added little by little at 25 ° C. and stirred for 1 hour. The temperature of the reactor was then raised to 60 ° C. and then stirred for 1 hour.
내부온도를 15도℃로 냉각한 후 물 300g을 반응기내에 넣고 30분간 교반하고, 여과하여 얻은 고체를 건조하여 최종적으로 하기 화학식 6의 디케토피롤로피롤 유도체를 얻었다.After the internal temperature was cooled to 15 ° C., 300 g of water was added to the reactor, stirred for 30 minutes, and the solid obtained by filtration was dried to finally obtain a diketopyrrolopyrrole derivative represented by Chemical Formula 6.
[화학식 6][Formula 6]
<< 제조예Production Example 2>: 안료 분산액의 제조 2>: Preparation of pigment dispersion
C.I.Red254 (Ciba, B-CF) 15 중량%C.I.Red254 (Ciba, B-CF) 15% by weight
화학식 6의 화합물 1.5 중량%1.5 wt% of a compound of Formula 6
분산제 (BYK, Diperbyk111) 3 중량%Dispersant (BYK, Diperbyk111) 3 wt%
아크릴산 벤질메타크릴레이트 공중합체(미원상사, NPR8000) 3 중량%3% by weight of acrylic acid benzyl methacrylate copolymer (Miwon Corporation, NPR8000)
프로필렌글리콜메틸에틸아세테이트 77.5 중량%Propylene glycol methyl ethyl acetate 77.5 wt%
상기 제조예 1에서 제조된 화학식 1의 안료유도체 및 상기 각각의 성분을 혼합하고, 12시간 동안 페인트쉐이커(아사다社)를 이용해서 분산을 실시하였다.The pigment derivative of
<< 비교제조예Comparative Production Example 1>: 안료 분산액의 제조 1>: Preparation of pigment dispersion
C.I.Red254 (Ciba, B-CF) 15 중량%C.I.Red254 (Ciba, B-CF) 15% by weight
분산제 (BYK, Diperbyk163) 3 중량%Dispersant (BYK, Diperbyk163) 3 wt%
아크릴산 벤질메타크릴레이트 공중합체(미원상사, NPR8000) 3 중량%3% by weight of acrylic acid benzyl methacrylate copolymer (Miwon Corporation, NPR8000)
프로필렌글리콜메틸에틸아세테이트 79 중량%Propylene glycol methyl ethyl acetate 79% by weight
상기 각각의 성분을 혼합하고 12시간 동안 페인트쉐이커(아사다社)를 이용해서 분산을 실시하였다.Each component was mixed and dispersed using a paint shaker (Asada Co., Ltd.) for 12 hours.
<< 실시예Example 1>: 컬러 필터용 감광성 수지 조성물의 제조 1>: Preparation of the photosensitive resin composition for color filters
제조예 2에서 제조된 안료분산액 50 중량%50% by weight of the pigment dispersion prepared in Preparation Example 2.
아크릴산 벤질메타크릴레이트 공중합체(미원상사, NPR8000) 5 중량%5% by weight of acrylic acid benzyl methacrylate copolymer (Miwon Corporation, NPR8000)
광중합성 모노머 (동양합성社, DPHA) 5 중량%Photopolymerizable monomer (Dongyang Synthetic, DPHA) 5 wt%
프로필렌글리콜메틸에틸아세테이트 39.5 중량%Propylene glycol methyl ethyl acetate 39.5% by weight
트리아진계 광중합 개시제(일본화약社, TPP) 0.5 중량%Triazine photopolymerization initiator (TPP) 0.5% by weight
프로필렌글리콜 메틸에틸아세테이트에 트리아진계 광중합 개시제를 용해한 후, 30분 동안 상온에서 교반하였다. 이어서, 이 혼합물에 아크릴산 벤질메타크릴레이트 공중합체 바인더 및 광중합성 모노머를 첨가하고 30분 동안 상온에서 교반하였다. 얻어진 생성물에 실시예 1에서 제조된 안료분산액을 넣고, 1시간 동안 상온에서 교반 한 후, 1회 여과하여 컬러 필터용 감광성 수지 조성물을 제조하였다.The triazine photoinitiator was dissolved in propylene glycol methylethyl acetate, and then stirred at room temperature for 30 minutes. Then, the benzyl methacrylate copolymer binder and the photopolymerizable monomer were added to the mixture and stirred at room temperature for 30 minutes. The pigment dispersion prepared in Example 1 was added to the obtained product, stirred at room temperature for 1 hour, and then filtered once to prepare a photosensitive resin composition for color filters.
<< 비교실시예Comparative Example 1>: 컬러 필터용 감광성 수지 조성물의 제조 1>: Preparation of the photosensitive resin composition for color filters
제조예 2에서 제조된 안료분산액 대신 비교제조예 1에서 제조한 안료분산액 을 이용한 것을 제외하고는 실시예 1과 동일하게 실시하여 컬러 필터용 감광성 수지 조성물을 제조하였다.A photosensitive resin composition for a color filter was prepared in the same manner as in Example 1 except that the pigment dispersion prepared in Comparative Preparation Example 1 was used instead of the pigment dispersion prepared in Preparation Example 2.
< 실험예 >: 컬러 필터용 패턴의 주사전자현미경( SEM ; scanning election microscope) 분석 < Experimental example > : Scanning electron microscope of the pattern for color filters ( SEM ; scanning) election microscope analysis
상기 실시예 1 및 비교실시예 1에 따라 제조된 컬러 필터용 감광성 수지 조성물을 실리콘 웨이퍼(LG 실트론社) 위에 스핀 코팅기(KDNS사, K-Spin8)를 사용하여 0.8㎛ 높이로 코팅 후, 노광기(니콘社, I10C)를 사용하여 350ms로 노광하였다. 이어서 현상액으로(TMAH 0.2%) 현상하여 패턴을 제작한 후, CD SEM 분석기(KLA-Tencor사, 8100XP)를 사용하여 해상도 및 잔사 여부를 확인하였고, 실시예 1 및 비교실시예 1의 결과를 각각 도 1 및 2에 나타내었다. After coating the photosensitive resin composition for color filters prepared according to Example 1 and Comparative Example 1 on a silicon wafer (LG Siltron) using a spin coating machine (KDNS, K-Spin8) to a height of 0.8㎛, an exposure machine ( Nikon, I10C) was used for exposure at 350 ms. Subsequently, after developing with a developer (TMAH 0.2%) to produce a pattern, using a CD SEM analyzer (KLA-Tencor, 8100XP) was confirmed the resolution and residue, and the results of Example 1 and Comparative Example 1, respectively 1 and 2 are shown.
여기서, 도 1 및 2는 1.4㎛의 패턴의 해상도를 각각 나타낸 것이다. 도 1 및 2를 참고하면, 실시예 1에 따른 컬러 필터용 감광성 수지 조성물의 노광 후 현상 패턴의 해상도는 비교실시예 1에 비하여 정사각형을 이루는 해상도가 높음을 확인할 수 있었다. 또한, 실시예 1에 따른 컬러 필터용 감광성 수지 조성물에서는 잔사가 존재하지 않았으나, 비교실시예 1에서는 잔사가 매우 많이 존재하는 것을 확인할 수 있었다. 이로부터 본 발명의 감광성 수지 조성물은 패턴 형성 시 해상도를 증가시키고 잔사를 감소시킴을 확인할 수 있었다.1 and 2 show the resolution of the pattern of 1.4 mu m, respectively. 1 and 2, it was confirmed that the resolution of the post-exposure development pattern of the photosensitive resin composition for color filters according to Example 1 was higher than that of Comparative Example 1 to form a square. In addition, in the photosensitive resin composition for color filters which concerns on Example 1, there was no residue, but in Comparative Example 1, it was confirmed that there are very many residues. From this, it was confirmed that the photosensitive resin composition of the present invention increases the resolution and reduces the residue during pattern formation.
이상을 통해 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.Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention and the accompanying drawings. Naturally, it belongs to the scope of the invention.
도 1은 본 발명의 실시예 1에서 제조된 컬러 필터용 감광성 수지 조성물을 이용하여 제조한 패턴의 주사전자현미경(SEM; scanning electron microscope) 사진이다. 1 is a scanning electron microscope (SEM) photograph of a pattern prepared using the photosensitive resin composition for color filters prepared in Example 1 of the present invention.
도 2는 비교실시예 1에 따른 컬러 필터용 감광성 수지 조성물을 사용하여 제조된 컬러 필터용 감광성 수지 조성물을 이용하여 얻어진 패턴의 주사전자현미경 사진이다. 2 is a scanning electron micrograph of a pattern obtained by using the photosensitive resin composition for color filters manufactured using the photosensitive resin composition for color filters according to Comparative Example 1. FIG.
Claims (5)
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| JPH1192477A (en) | 1997-07-30 | 1999-04-06 | Ciba Specialty Chem Holding Inc | Polymerizable diketopyrrolopyrroles |
| JP2001051112A (en) | 1999-08-09 | 2001-02-23 | Toyo Ink Mfg Co Ltd | Photosensitive coloring composition for color filter and color filter using it |
| JP2007133131A (en) | 2005-11-10 | 2007-05-31 | Toyo Ink Mfg Co Ltd | Red colored composition for color filter, color filter and liquid crystal display device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH1192477A (en) | 1997-07-30 | 1999-04-06 | Ciba Specialty Chem Holding Inc | Polymerizable diketopyrrolopyrroles |
| JP2001051112A (en) | 1999-08-09 | 2001-02-23 | Toyo Ink Mfg Co Ltd | Photosensitive coloring composition for color filter and color filter using it |
| JP2007133131A (en) | 2005-11-10 | 2007-05-31 | Toyo Ink Mfg Co Ltd | Red colored composition for color filter, color filter and liquid crystal display device |
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