KR20180035074A - Novel compound, photosensitive resin composition including the same and color filter - Google Patents
Novel compound, photosensitive resin composition including the same and color filter Download PDFInfo
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- KR20180035074A KR20180035074A KR1020160125108A KR20160125108A KR20180035074A KR 20180035074 A KR20180035074 A KR 20180035074A KR 1020160125108 A KR1020160125108 A KR 1020160125108A KR 20160125108 A KR20160125108 A KR 20160125108A KR 20180035074 A KR20180035074 A KR 20180035074A
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- South Korea
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- resin composition
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 87
- 239000011342 resin composition Substances 0.000 title claims abstract description 44
- 239000000126 substance Substances 0.000 claims abstract description 24
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- 239000000049 pigment Substances 0.000 claims description 33
- -1 acryloxy group Chemical group 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 21
- 239000011230 binding agent Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 15
- 239000000975 dye Substances 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
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- 230000015572 biosynthetic process Effects 0.000 description 27
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- 230000000052 comparative effect Effects 0.000 description 13
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- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 3
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- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
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- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- MDEDOIDXVJXDBW-UHFFFAOYSA-N methoxymethyl acetate Chemical compound COCOC(C)=O MDEDOIDXVJXDBW-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical compound COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
- GSJFXBNYJCXDGI-UHFFFAOYSA-N methyl 2-hydroxyacetate Chemical compound COC(=O)CO GSJFXBNYJCXDGI-UHFFFAOYSA-N 0.000 description 1
- AKWHOGIYEOZALP-UHFFFAOYSA-N methyl 2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC AKWHOGIYEOZALP-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/02—Carbamic acids; Salts of carbamic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C07F7/0818—
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- G02B5/00—Optical elements other than lenses
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- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
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- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
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- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
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- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G—PHYSICS
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
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- Architecture (AREA)
- Structural Engineering (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
Description
본 기재는 신규한 화합물, 이를 포함하는 감광성 수지 조성물 및 이를 이용하여 제조되는 컬러필터에 관한 것이다.The present invention relates to a novel compound, a photosensitive resin composition containing the same, and a color filter manufactured using the same.
디스플레이 장치 중의 하나인 액정디스플레이 장치는 경량화, 박형화, 저가, 저소비 전력 구동화 및 우수한 집적회로와의 접합성 등의 장점을 가지고 있어, 노트북 컴퓨터, 모니터 및 TV 화상용으로 그 사용범위가 확대되고 있다. 이와 같은 액정디스플레이 장치는 블랙 매트릭스, 컬러필터 및 ITO 화소전극이 형성된 하부 기판과, 액정층, 박막트랜지스터, 축전캐패시터층으로 구성된 능동회로부와 ITO 화소전극이 형성된 상부 기판을 포함하여 구성된다. 컬러 필터는 화소 사이의 경계부를 차광하기 위해서 투명 기판 상에 정해진 패턴으로 형성된 블랙 매트릭스층 및 각각의 화소를 형성하기 위해 복수의 색, 통상적으로, 적(R), 녹(G), 청(B)의 3원색을 정해진 순서로 배열한 화소부가 차례로 적층된 구조를 취하고 있다. The liquid crystal display device, which is one of the display devices, has advantages such as lightness, thinness, low cost, low power consumption driving and bonding with a good integrated circuit, and the use range thereof is expanding for notebook computers, monitors and TV images. Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and ITO pixel electrodes are formed, and an upper substrate on which an active circuit composed of a liquid crystal layer, a thin film transistor, a capacitor capacitor layer and an ITO pixel electrode are formed. The color filter includes a black matrix layer formed in a predetermined pattern on a transparent substrate so as to shield the boundary between pixels, and a plurality of colors, typically red (R), green (G), blue ) Are arranged in a predetermined order, and the pixel portions are sequentially stacked.
컬러 필터를 구현하는 방법 중의 하나인 안료 분산법은 흑색 매트릭스가 제공된 투명한 기질 위에 착색제를 함유하는 광중합성조성물을 코팅하고, 형성하고자 하는 형태의 패턴을 노광한 후, 비노광 부위를 용매로 제거하여 열경화시키는 일련의 과정을 반복함으로써 착색박막이 형성되는 방법이다. 안료 분산법에 따른 컬러필터 제조에 사용되는 착색 감광성 수지 조성물은 일반적으로 알칼리 가용성 수지, 광중합성단량체, 광중합 개시제, 에폭시 수지, 용매, 기타 첨가제 등으로 이루어진다. 상기 안료 분산법은 휴대폰, 노트북, 모니터, TV 등의 LCD를 제조하는 데 활발하게 응용되고 있다. 그러나, 근래에는 여러 가지 장점을 가지는 안료 분산법을 이용한 컬러필터용 감광성 수지 조성물에 있어서도 우수한 패턴 특성뿐만 아니라 더욱 향상된 성능이 요구되고 있다. 특히 높은 색재현율과 함께 고휘도 및 고명암비의 특성이 시급히 요구되고 있는 실정이다.In the pigment dispersion method, which is one of the methods of implementing a color filter, a photopolymerizable composition containing a colorant is coated on a transparent substrate provided with a black matrix, a pattern of a pattern to be formed is exposed, And a coloring thin film is formed by repeating a series of processes of thermosetting. The colored photosensitive resin composition used in the production of a color filter according to the pigment dispersion method generally comprises an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives. The pigment dispersion method is actively applied to manufacturing LCDs for mobile phones, notebooks, monitors, TVs and the like. However, recently, a photosensitive resin composition for a color filter using a pigment dispersion method having various advantages has been required to have not only superior pattern characteristics but also further improved performance. In particular, high color rendering and high brightness and high contrast ratio characteristics are urgently required.
이미지 센서는 휴대전화 카메라나 DSC(digital still camera)등에서 영상을 생성해 내는 영상 촬상 소자 부품을 일컫는 것으로, 그 제작 공정과 응용 방식에 따라 크게 고체 촬상 소자(charge coupled device, CCD) 이미지 센서와 상보성 금속 산화물 반도체(complementary metal oxide semiconductor, CMOS) 이미지 센서로 분류할 수 있다. 고체 촬상 소자 또는 상보성 금속 산화물 반도체에 이용되는 컬러 촬상 소자는 수광 소자상에 적색(red), 녹색(green), 청색(blue)의 덧셈 혼합 원색의 필터 세그먼트(filter segment)를 구비하는 컬러 필터(color filter)를 각각 설치하고 색 분해하는 것이 일반적이다. 최근 이러한 컬러 촬상 소자에 장착되는 컬러 필터의 패턴 크기는 2㎛ 이하 크기로 기존 LCD용 컬러 필터 패턴의 1/100 내지 1/200 배이다. 이에 따라 해상도의 증가 및 잔사의 감소가 소자의 성능을 좌우하는 중요한 항목이다.The image sensor refers to a component of an image pickup device that generates an image from a mobile phone camera or a digital still camera (DSC). The image sensor is largely divided into a charge coupled device (CCD) image sensor and a complementary And a complementary metal oxide semiconductor (CMOS) image sensor. A color image pickup device used for a solid-state image pickup device or a complementary metal oxide semiconductor is a color filter (hereinafter referred to as " color filter ") having a filter segment of additive mixed primary colors of red, green, color filters) are separately installed and color-separated. In recent years, the pattern size of a color filter mounted on such a color imaging device has a size of 2 탆 or less and is 1/100 to 1/200 times that of a color filter pattern for a conventional LCD. Accordingly, the increase of the resolution and the reduction of the residue are important items that determine the performance of the device.
안료형 감광성 수지 조성물로 제조된 컬러필터에서는 안료 입자 크기에서 비롯되는 휘도와명암비의 한계가 존재한다. 또한 이미지 센서용 컬러 촬상 소자의 경우에는 미세한 패턴 형성을 위해 더 작은 분산입도가 요구된다. 이러한 요구에 부응하고자, 안료 대신 입자를 이루지 않는 염료를 도입하여 염료에 적합한 감광성 수지 조성물을 제조하여 휘도와 명암비가 개선된 컬러필터를 구현하려는 시도가 있다. 그러나 염료의 경우 안료 대비 내광 및 내열 등의 내구성의 열세로 인하여 휘도의 저하가 우려된다.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 demands, attempts have been made to introduce a dye that does not form particles instead of a pigment to produce a photosensitive resin composition suitable for a dye, thereby realizing a color filter having improved luminance and contrast ratio. However, in the case of dyes, the luminance may be lowered due to the poor durability such as light resistance and heat resistance compared with the pigment.
일 구현예는 휘도 및 명암비가 우수한 신규 화합물을 제공하기 위한 것이다.One embodiment is to provide a novel compound having excellent brightness and contrast ratio.
다른 일 구현예는 상기 신규 화합물을 포함하는 감광성 수지 조성물을 제공하기 위한 것이다.Another embodiment is to provide a photosensitive resin composition comprising the novel compound.
또 다른 일 구현예는 상기 감광성 수지 조성물을 이용하여 제조된 컬러필터를 제공하기 위한 것이다. Another embodiment is to provide a color filter manufactured using the photosensitive resin composition.
일 구현예는 하기 화학식 1로 표시되는 화합물을 제공한다.An embodiment provides a compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
R1 내지 R4는 각각 독립적으로 수소 원자 또는 하기 화학식 2로 표시되는 치환기이고, 단 상기 R1 내지 R4 중 어느 하나는 반드시 하기 화학식 2로 표시되는 치환기이고,R 1 to R 4 are each independently a hydrogen atom or a substituent represented by the following formula (2), provided that any one of R 1 to R 4 is a substituent represented by the following formula (2)
[화학식 2](2)
상기 화학식 2에서,In Formula 2,
L1은 단일결합 또는 치환 또는 비치환된 C1 내지 C10 알킬렌기이고, L 1 is a single bond or a substituted or unsubstituted C1 to C10 alkylene group,
R13은 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기, 치환 또는 비치환된 C6 내지 C20 아릴기, 치환 또는 비치환된 아크릴레이트기, 치환 또는 비치환된 실란기 또는 치환 또는 비치환된 C10 내지 C20 융합고리기이고,R 13 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted acrylate group, a substituted or unsubstituted silane Or a substituted or unsubstituted C10 to C20 fused ring group,
R5 내지 R8은 각각 독립적으로 수소 원자 또는 히드록시기이고, 단 상기 R5 내지 R8 중 어느 하나는 반드시 히드록시기이고,R 5 to R 8 are each independently a hydrogen atom or a hydroxy group, provided that any one of R 5 to R 8 is a hydroxy group,
R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다.R 9 to R 12 each independently represent a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
상기 R1은 상기 화학식 2로 표시될 수 있다The R 1 may be represented by the general formula (2)
상기 R5는 히드록시기일 수 있다.The R 5 may be a hydroxy group.
상기 치환 또는 비치환된 아크릴레이트기는 하기 화학식 3으로 표시될 수 있다.The substituted or unsubstituted acrylate group may be represented by the following general formula (3).
[화학식 3](3)
상기 화학식 3에서,In Formula 3,
R14는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 14 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
상기 치환 또는 비치환된 실란기는 하기 화학식 4로 표시될 수 있다.The substituted or unsubstituted silane group may be represented by the following general formula (4).
[화학식 4][Chemical Formula 4]
상기 화학식 4에서,In Formula 4,
R15 내지 R17은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 15 to R 17 are each independently a substituted or unsubstituted C1 to C10 alkyl group.
상기 치환 또는 비치환된 C10 내지 C20 융합고리기는 아다만틸(ADAMANTYL)기일 수 있다.The substituted or unsubstituted C10 to C20 fused ring group may be an adamantyl group.
상기 화학식 1로 표시되는 화합물은 하기 화학식 5로 표시될 수 있다.The compound represented by the formula (1) may be represented by the following formula (5).
[화학식 5][Chemical Formula 5]
상기 화학식 5에서,In Formula 5,
L1은 단일결합 또는 치환 또는 비치환된 C1 내지 C10 알킬렌기이고, L 1 is a single bond or a substituted or unsubstituted C1 to C10 alkylene group,
R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,R 9 to R 12 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group,
R18은 하기 화학식 5-1 내지 화학식 5-7 중 어느 하나로 표시되고,R 18 is represented by any one of the following formulas (5-1) to (5-7)
[화학식 5-1][Formula 5-1]
[화학식 5-2][Formula 5-2]
[화학식 5-3][Formula 5-3]
[화학식 5-4][Formula 5-4]
[화학식 5-5][Formula 5-5]
[화학식 5-6][Formula 5-6]
[화학식 5-7][Formula 5-7]
상기 화학식 5-1 내지 화학식 5-4 및 화학식 5-6에서,In the above Formulas 5-1 to 5-4 and 5-6,
R19는 할로겐 원자, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C1 내지 C10 알콕시기, *-C(=O)ORx 또는 *-OC(=O)Rx이고, 상기 Rx는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,R 19 represents a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, -C (= O) OR x or -OC (= O) R x , x is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
Ry 및 Rz는 각각 독립적으로 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,R y and R z are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R20 내지 R22는 각각 독립적으로 치환 또는 비치환된 C1 내지 C8 알킬기이고,R 20 to R 22 are each independently a substituted or unsubstituted C1 to C8 alkyl group,
p1은 0 내지 5의 정수이다.p1 is an integer of 0 to 5;
상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 내지 화학식 1-7로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.The compound represented by Formula 1 may be represented by any one selected from the following Formulas 1-1 to 1-7.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
[화학식 1-6][Chemical Formula 1-6]
[화학식 1-7][Chemical Formula 1-7]
다른 일 구현예는 상기 화합물을 포함하는 감광성 수지 조성물을 제공한다.Another embodiment provides a photosensitive resin composition comprising the above compound.
상기 화합물은 염료일 수 있다.The compound may be a dye.
상기 염료는 녹색 염료일 수 있다.The dye may be a green dye.
상기 감광성 수지 조성물은 바인더 수지, 광중합성 단량체, 광중합 개시제 및 용매를 더 포함할 수 있다.The photosensitive resin composition may further comprise a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.
상기 감광성 수지 조성물은 안료를 더 포함할 수 있다.The photosensitive resin composition may further comprise a pigment.
상기 안료는 상기 감광성 수지 조성물 총량에 대해 10 중량% 내지 20 중량%로 포함될 수 있다.The pigment may be included in an amount of 10% by weight to 20% by weight based on the total amount of the photosensitive resin composition.
상기 감광성 수지 조성물은, 감광성 수지 조성물 총량에 대해, 상기 화합물 1 중량% 내지 10 중량%; 상기 바인더 수지 1 중량% 내지 10 중량%; 상기 광중합성 단량체 5 중량% 내지 15 중량%; 상기 광중합 개시제 0.1 중량% 내지 5 중량%; 및 상기 용매 잔부량을 포함할 수 있다.Wherein the photosensitive resin composition contains 1 to 10% by weight of the compound, based on the total amount of the photosensitive resin composition; 1% by weight to 10% by weight of the binder resin; 5% to 15% by weight of the photopolymerizable monomer; 0.1% by weight to 5% by weight of the photopolymerization initiator; And the solvent balance.
상기 감광성 수지 조성물은 말론산, 3-아미노-1,2-프로판디올, 비닐기 또는 (메타)아크릴옥시기를 포함하는 실란계 커플링제, 레벨링제, 계면활성제, 라디칼 중합 개시제 또는 이들의 조합을 더 포함할 수 있다.The photosensitive resin composition may further include a silane coupling agent comprising malonic acid, 3-amino-1,2-propanediol, a vinyl group or a (meth) acryloxy group, a leveling agent, a surfactant, a radical polymerization initiator, .
또 다른 일 구현예는 상기 감광성 수지 조성물을 이용하여 제조된 컬러필터를 제공한다.Another embodiment provides a color filter manufactured using the photosensitive resin composition.
기타 본 발명의 구현예들의 구체적인 사항은 이하의 상세한 설명에 포함되어 있다.Other details of the embodiments of the present invention are included in the following detailed description.
일 구현예에 따른 화합물을 사용함으로써, 휘도 및 명암비가 우수한 컬러필터를 구현할 수 있다.By using the compound according to one embodiment, a color filter having excellent luminance and contrast ratio can be realized.
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"이란 화합물 중의 적어도 하나의 수소 원자가 할로겐 원자(F, Cl, Br, I), 히드록시기, C1 내지 C20 알콕시기, 니트로기, 시아노기, 아민기, 이미노기, 아지도기, 아미디노기, 히드라지노기, 히드라조노기, 카르보닐기, 카르바밀기, 티올기, 에스테르기, 에테르기, 카르복실기 또는 그것의 염, 술폰산기 또는 그것의 염, 인산이나 그것의 염, C1 내지 C20 알킬기, C2 내지 C20 알케닐기, C2 내지 C20 알키닐기, C6 내지 C30 아릴기, C3 내지 C20 사이클로알킬기, C3 내지 C20 사이클로알케닐기, C3 내지 C20 사이클로알키닐기, C2 내지 C20 헤테로사이클로알킬기, C2 내지 C20 헤테로사이클로알케닐기, C2 내지 C20 헤테로사이클로알키닐기 또는 이들의 조합의 치환기로 치환된 것을 의미한다.Unless otherwise specified herein, "substituted" means that at least one hydrogen atom in the compound is replaced by a halogen atom (F, Cl, Br, I), a hydroxy group, A thio group, an ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, an acid anhydride, an amide group, an azo group, an azido group, an amidino group, a hydrazino group, a hydrazino group, a carbonyl group, , A C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C30 aryl group, a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C2 to C20 heterocycloalkyl group , A C2 to C20 heterocycloalkenyl group, a C2 to C20 heterocycloalkynyl group, or a combination thereof.
본 명세서에서 특별한 언급이 없는 한, "헤테로사이클로알킬기", "헤테로사이클로알케닐기", "헤테로사이클로알키닐기" 및 "헤테로사이클로알킬렌기"란 각각 사이클로알킬, 사이클로알케닐, 사이클로알키닐 및 사이클로알킬렌의 고리 화합물 내에 적어도 하나의 N, O, S 또는 P의 헤테로 원자가 존재하는 것을 의미한다.Unless otherwise stated, the terms "heterocycloalkyl", "heterocycloalkenyl", "heterocycloalkynyl" and "heterocycloalkylene" refer to cycloalkyl, cycloalkenyl, cycloalkynyl, and cycloalkyl Means that at least one heteroatom of N, O, S or P is present in the ring compound of the ring.
본 명세서에서 특별한 언급이 없는 한, "(메타)아크릴레이트"는 "아크릴레이트"와 "메타크릴레이트" 둘 다 가능함을 의미한다.As used herein, unless otherwise specified, "(meth) acrylate" means that both "acrylate" and "methacrylate" are possible.
본 명세서에서 특별한 언급이 없는 한, "조합"이란 혼합 또는 공중합을 의미한다."Combination" as used herein, unless otherwise specified, means mixing or copolymerization.
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 특별한 언급이 없는 한, 융합고리라 함은 2 이상의 고리가 적어도 하나 이상의 탄소-탄소 결합을 서로 공유하는 고리를 의미한다.Unless otherwise specified herein, fused ring means a ring in which at least two rings share at least one carbon-carbon bond with each other.
또한 본 명세서에서 특별한 언급이 없는 한, "*"는 동일하거나 상이한 원자 또는 화학식과 연결되는 부분을 의미한다.Also, unless otherwise specified herein, "*" means the same or different atom or moiety connected to the formula.
일 구현예에 따른 화합물은 하기 화학식 1로 표시된다.The compound according to one embodiment is represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
R1 내지 R4는 각각 독립적으로 수소 원자 또는 하기 화학식 2로 표시되는 치환기이고, 단 상기 R1 내지 R4 중 어느 하나는 반드시 하기 화학식 2로 표시되는 치환기이고,R 1 to R 4 are each independently a hydrogen atom or a substituent represented by the following formula (2), provided that any one of R 1 to R 4 is a substituent represented by the following formula (2)
[화학식 2](2)
상기 화학식 2에서,In Formula 2,
L1은 단일결합 또는 치환 또는 비치환된 C1 내지 C10 알킬렌기이고, L 1 is a single bond or a substituted or unsubstituted C1 to C10 alkylene group,
R13은 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기, 치환 또는 비치환된 C6 내지 C20 아릴기, 치환 또는 비치환된 아크릴레이트기, 치환 또는 비치환된 실란기 또는 치환 또는 비치환된 C10 내지 C20 융합고리기이고,R 13 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted acrylate group, a substituted or unsubstituted silane Or a substituted or unsubstituted C10 to C20 fused ring group,
R5 내지 R8은 각각 독립적으로 수소 원자 또는 히드록시기이고, 단 상기 R5 내지 R8 중 어느 하나는 반드시 히드록시기이고,R 5 to R 8 are each independently a hydrogen atom or a hydroxy group, provided that any one of R 5 to R 8 is a hydroxy group,
R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다.R 9 to R 12 each independently represent a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
상기 화학식 1로 표시되는 화합물은 하기 도식에서 보는 바와 같이, 3가지 공명구조를 가지나, 본 명세서에서는 편의 상 1가지의 공명구조로만 상기 화학식 1로 표시되는 화합물을 표시했을 뿐이다. 즉, 상기 화학식 1로 표시되는 화합물은 상기 3가지 공명구조 중 어느 하나로 표시될 수 있다.The compound represented by the formula (1) has three resonance structures as shown in the following diagram, but for the sake of convenience, the compound represented by the formula (1) is merely represented by one resonance structure. That is, the compound represented by Formula 1 may be represented by any one of the three resonance structures.
[도식][scheme]
일 구현예에 따른 화합물은 상기 화학식 1로 표시됨에 따라, 특히 우레탄 연결기를 포함하는 관능기가 벤젠 고리의 치환기로 존재함에 따라, 상기 화학식 1로 표시되는 구조를 가지지 않는 다른 스쿠아릴륨계 화합물보다 우수한 휘도 및 명암비를 가질 수 있다.The compounds according to one embodiment are represented by the above formula (1). Especially, when a functional group containing a urethane linking group is present as a substituent of a benzene ring, the luminance of the compound represented by the formula 1 is lower than that of other squarylium compounds And a contrast ratio.
상기 화학식 1에서, R1은 상기 화학식 2로 표시될 수 있고, R5는 히드록시기일 수 있다. 우레탄 연결기를 포함하는 관능기 및 히드록시기가 상기 위치에 존재함으로써, 휘도 및 명암비가 우수한 유리한 효과가 있다. In Formula 1, R 1 may be represented by Formula 2, and R 5 may be a hydroxy group. The presence of the functional group and the hydroxyl group including the urethane linkage at the above positions has an advantageous effect of excellent luminance and contrast ratio.
상기 치환 또는 비치환된 아크릴레이트기는 하기 화학식 3으로 표시될 수 있다. The substituted or unsubstituted acrylate group may be represented by the following general formula (3).
[화학식 3](3)
상기 화학식 3에서,In Formula 3,
R14는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 14 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
상기 치환 또는 비치환된 실란기는 하기 화학식 4로 표시될 수 있다.The substituted or unsubstituted silane group may be represented by the following general formula (4).
[화학식 4][Chemical Formula 4]
상기 화학식 4에서,In Formula 4,
R15 내지 R17은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬기이다.R 15 to R 17 are each independently a substituted or unsubstituted C1 to C10 alkyl group.
상기 치환 또는 비치환된 C10 내지 C20 융합고리기는 아다만틸(ADAMANTYL)기일 수 있다.The substituted or unsubstituted C10 to C20 fused ring group may be an adamantyl group.
예컨대, 상기 화학식 1로 표시되는 화합물은 하기 화학식 5로 표시될 수 있다.For example, the compound represented by Formula 1 may be represented by Formula 5 below.
[화학식 5][Chemical Formula 5]
상기 화학식 5에서,In Formula 5,
L1은 단일결합 또는 치환 또는 비치환된 C1 내지 C10 알킬렌기이고, L 1 is a single bond or a substituted or unsubstituted C1 to C10 alkylene group,
R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,R 9 to R 12 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group,
R18은 하기 화학식 5-1 내지 화학식 5-7 중 어느 하나로 표시되고,R 18 is represented by any one of the following formulas (5-1) to (5-7)
[화학식 5-1][Formula 5-1]
[화학식 5-2][Formula 5-2]
[화학식 5-3][Formula 5-3]
[화학식 5-4][Formula 5-4]
[화학식 5-5][Formula 5-5]
[화학식 5-6][Formula 5-6]
[화학식 5-7][Formula 5-7]
상기 화학식 5-1 내지 화학식 5-4 및 화학식 5-6에서,In the above Formulas 5-1 to 5-4 and 5-6,
R19는 할로겐 원자, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C1 내지 C10 알콕시기, *-C(=O)ORx 또는 *-OC(=O)Rx이고, 상기 Rx는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,R 19 represents a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, -C (= O) OR x or -OC (= O) R x , x is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
Ry 및 Rz는 각각 독립적으로 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,R y and R z are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R20 내지 R22는 각각 독립적으로 치환 또는 비치환된 C1 내지 C8 알킬기이고,R 20 to R 22 are each independently a substituted or unsubstituted C1 to C8 alkyl group,
p1은 0 내지 5의 정수이다.p1 is an integer of 0 to 5;
예컨대, 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 내지 화학식 1-7로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.For example, the compound represented by Formula 1 may be represented by any one selected from the following Formulas 1-1 to 1-7.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
[화학식 1-3][Formula 1-3]
[화학식 1-4][Formula 1-4]
[화학식 1-5][Formula 1-5]
[화학식 1-6][Chemical Formula 1-6]
[화학식 1-7][Chemical Formula 1-7]
일 구현예에 따른 화합물은 녹색 염료로서 단독으로 사용할 수도 있고, 조색 염료와 혼합하여 사용할 수도 있다.The compound according to one embodiment may be used alone as a green dye, or may be mixed with a coloring dye.
상기 조색 염료로는 트리아릴메탄계 염료, 안트라퀴논계 염료, 벤질리덴계 염료, 시아닌계 염료, 프탈로시아닌계 염료, 아자포피린계 염료, 인디고계 염료, 크산텐계 염료 등을 들 수 있다. Examples of the coloring dye include triarylmethane dyes, anthraquinone dyes, benzylidene dyes, cyanine dyes, phthalocyanine dyes, azapphyrin dyes, indigo dyes, and xanthene dyes.
일 구현예에 따른 화합물은 또한 안료와 혼합하여 사용할 수도 있다.The compounds according to one embodiment may also be used in admixture with pigments.
상기 안료로는 적색 안료, 녹색 안료, 청색 안료, 황색 안료, 흑색 안료 등을 사용할 수 있다.As the pigment, a red pigment, a green pigment, a blue pigment, a yellow pigment, a black pigment and the like can be used.
상기 적색 안료의 예로는 C.I. 적색 안료 254, C.I. 적색 안료 255, C.I. 적색 안료 264, C.I. 적색 안료 270, C.I. 적색 안료 272, C.I. 적색 안료 177, C.I. 적색 안료 89 등을 들 수 있다. 상기 녹색 안료의 예로는 C.I. 녹색 안료 36, C.I. 녹색 안료 7, C.I. 녹색 안료 58 등을 들 수 있다. 상기 청색 안료의 예로는 C.I. 청색 안료 15:6, C.I. 청색 안료 15, C.I. 청색 안료 15:1, C.I. 청색 안료 15:2, C.I. 청색 안료 15:3, C.I. 청색 안료 15:4, C.I. 청색 안료 15:5, C.I. 청색 안료 16 등과 같은 구리 프탈로시아닌 안료를 들 수 있다. 상기 황색 안료의 예로는 C.I. 황색 안료 139 등과 같은 이소인돌린계 안료, C.I. 황색 안료 138 등과 같은 퀴노프탈론계 안료, C.I. 황색 안료 150 등과 같은 니켈 컴플렉스 안료 등을 들 수 있다. 상기 흑색 안료의 예로는 아닐린 블랙, 퍼릴렌 블랙, 티타늄 블랙, 카본 블랙 등을 들 수 있다. 상기 안료는 이들을 단독으로 또는 둘 이상 혼합하여 사용할 수 있으며, 이들의 예에 한정되는 것은 아니다. Examples of the red pigment include C.I. Red pigment 254, C.I. Red pigment 255, C.I. Red pigment 264, C.I. Red pigment 270, C.I. Red pigment 272, C.I. Red pigment 177, C.I. Red pigment 89 and the like. Examples of the green pigment include C.I. Green pigment 36, C.I. Green pigment 7, C.I. Green pigment 58 and the like. Examples of the blue pigments include C.I. Blue pigment 15: 6, C.I. Blue pigment 15, C.I. Blue pigment 15: 1, C.I. Blue pigment 15: 2, C.I. Blue pigment 15: 3, C.I. Blue pigment 15: 4, C.I. Blue pigment 15: 5, C.I. Blue pigment 16, and the like. Examples of the yellow pigments include C.I. Yellow pigments 139 and the like, C.I. Quinophthalone-based pigments such as yellow pigment 138 and the like, C.I. And yellow complex pigments such as yellow pigment 150 and the like. Examples of the black pigment include aniline black, perylene black, titanium black, and carbon black. These pigments can be used singly or in combination of two or more thereof, but are not limited to these examples.
상기 안료는 분산액 형태로 감광성 수지 조성물에 포함될 수 있다. 이러한 안료 분산액은 상기 안료와 용매, 분산제, 분산수지 등으로 이루어질 수 있다.The pigment may be contained in the photosensitive resin composition in the form of a dispersion. Such a pigment dispersion may be composed of the pigment, a solvent, a dispersant, a dispersion resin, or the like.
상기 용매로는 에틸렌 글리콜 아세테이트, 에틸 셀로솔브, 프로필렌 글리콜 메틸 에테르 아세테이트, 에틸 락테이트, 폴리에틸렌 글리콜, 사이클로헥사논, 프로필렌 글리콜 메틸 에테르 등을 사용할 수 있으며, 이들 중에서 좋게는 프로필렌 글리콜 메틸 에테르 아세테이트를 사용할 수 있다. As the solvent, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether and the like can be used. Among them, propylene glycol methyl ether acetate is preferably used .
상기 분산제는 상기 안료가 분산액 내에 균일하게 분산되도록 도와주며, 비이온성, 음이온성 또는 양이온성의 분산제 모두 사용할 수 있다. 구체적으로는 폴리알킬렌 글리콜 또는 이의 에스테르, 폴리옥시 알킬렌, 다가 알콜 에스테르 알킬렌 옥사이드 부가물, 알코올 알킬렌 옥사이드 부가물, 술폰산 에스테르, 술폰산 염, 카르복시산 에스테르, 카르복시산 염, 알킬 아미드 알킬렌 옥사이드 부가물, 알킬 아민 등을 사용할 수 있으며, 이들은 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다.The dispersant helps to uniformly disperse the pigment in the dispersion, and any nonionic, anionic or cationic dispersant may be used. Specific examples thereof include polyalkylene glycols or esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, alkylamide alkylene oxide adducts Water, alkylamine, and the like. These may be used alone or in combination of two or more.
상기 분산수지는 카르복시기를 포함한 아크릴계 수지를 사용할 수 있으며, 이는 안료 분산액의 안정성을 향상시킬 수 있을 뿐만 아니라 픽셀의 패턴성도 개선시킬 수 있다.The dispersion resin may use an acrylic resin containing a carboxyl group, which not only improves the stability of the pigment dispersion but also improves the patterning of pixels.
일 구현예에 따른 화합물 및 상기 안료분산액을 혼합하여 사용할 경우 1:9 내지 9:1의 중량비, 구체적으로는 1:1 내지 1:5의 중량비로 혼합하여 사용할 수 있다. 상기 중량비 범위로 혼합할 경우 색특성을 유지하면서높은 휘도 및 명암비를 가질 수 있다. When the compound according to one embodiment and the pigment dispersion are mixed, they may be used in a weight ratio of 1: 9 to 9: 1, specifically, in a weight ratio of 1: 1 to 1: 5. When mixed in the weight ratio range, a high luminance and a high contrast ratio can be obtained while maintaining color characteristics.
다른 일 구현예에 따르면, 상기 화학식 1로 표시되는 화합물을 포함하는 감광성 수지 조성물을 제공한다.According to another embodiment, there is provided a photosensitive resin composition comprising the compound represented by the general formula (1).
상기 감광성 수지 조성물은 (A) 착색제(상기 화학식 1로 표시되는 화합물), (B) 바인더 수지, (C) 광중합성 단량체, (D) 광중합 개시제 및 (E) 용매를 포함할 수 있다.The photosensitive resin composition may contain (A) a colorant (a compound represented by the formula (1), (B) a binder resin, (C) a photopolymerizable monomer, (D) a photopolymerization initiator and (E) a solvent.
이하에서 각 성분에 대하여 구체적으로 설명한다.Each component will be described in detail below.
(A) 착색제(A) Colorant
상기 착색제는 상기 화학식 1로 표시되는 화합물을 포함할 수 있으며, 상기 화학식 1로 표시되는 화합물에 대해서는 전술하였다.The coloring agent may include the compound represented by Formula 1, and the compound represented by Formula 1 has been described above.
상기 착색제는 상기 화학식 1로 표시되는 외에 추가로 안료를 더 포함할 수 있으며, 상기 안료에 대해서는 전술하였다.The colorant may further comprise a pigment other than that represented by the formula (1), and the pigment has been described above.
상기 화학식 1로 표시되는 화합물은 상기 감광성 수지 조성물 총량에 대하여 1 중량% 내지 10 중량%, 예컨대 2 중량% 내지 8 중량%로 포함될 수 있고, 상기 안료는 상기 감광성 수지 조성물 총량에 대해 10 중량% 내지 20 중량%로 포함될 수 있다. 상기 화학식 1로 표시되는 화합물 및 안료를 각각 상기 범위 내로 사용할 경우, 원하는 색좌표에서 높은 휘도 및 명암비를 발현할 수 있다. The compound represented by Formula 1 may be contained in an amount of 1 wt% to 10 wt%, for example, 2 wt% to 8 wt% based on the total amount of the photosensitive resin composition, and the pigment may be contained in an amount of 10 wt% 20% by weight. When the compound represented by Formula 1 and the pigment are used within the above ranges, a high luminance and a high contrast ratio can be exhibited in a desired color coordinate.
(B) 바인더 수지(B) binder resin
상기 바인더 수지는 제1 에틸렌성 불포화 단량체 및 이와 공중합 가능한 제2 에틸렌성 불포화 단량체의 공중합체로, 하나 이상의 아크릴계 반복단위를 포함하는 수지일 수 있다. The binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer, and may be a resin containing at least one acrylic repeating unit.
상기 제1 에틸렌성 불포화 단량체는 하나 이상의 카르복시기를 함유하는 에틸렌성 불포화 단량체이며, 이의 구체적인 예로는 아크릴산, 메타크릴산, 말레산, 이타콘산, 푸마르산또는 이들의 조합을 들 수 있다.The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.
상기 제1 에틸렌성 불포화 단량체는 상기 바인더 수지 총량에 대하여 5 중량% 내지 50 중량%, 예컨대 10 중량% 내지 40 중량%로 포함될 수 있다.The first ethylenically unsaturated monomer may be included in an amount of 5 wt% to 50 wt%, for example, 10 wt% to 40 wt% with respect to the total amount of the binder resin.
상기 제2 에틸렌성 불포화 단량체는 스티렌, α-메틸스티렌, 비닐톨루엔, 비닐벤질메틸에테르 등의 방향족 비닐 화합물; 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 2-히드록시에틸(메타)아크릴레이트, 2-히드록시 부틸(메타)아크릴레이트, 벤질(메타)아크릴레이트, 사이클로헥실(메타)아크릴레이트, 페닐(메타)아크릴레이트 등의 불포화 카르복시산 에스테르 화합물; 2-아미노에틸(메타)아크릴레이트, 2-디메틸아미노에틸(메타)아크릴레이트 등의 불포화 카르복시산 아미노 알킬 에스테르 화합물; 초산비닐, 안식향산 비닐 등의 카르복시산 비닐 에스테르 화합물; 글리시딜(메타)아크릴레이트 등의 불포화 카르복시산 글리시딜 에스테르 화합물; (메타)아크릴로니트릴 등의 시안화 비닐 화합물; (메타)아크릴아미드 등의 불포화 아미드 화합물; 등을 들 수 있으며, 이들을 단독으로 또는 둘 이상 혼합하여 사용할 수 있다.The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly or in combination of two or more.
상기 바인더 수지의 구체적인 예로는 메타크릴산/벤질메타크릴레이트 공중합체, 메타크릴산/벤질메타크릴레이트/스티렌 공중합체, 메타크릴산/벤질메타크릴레이트/2-히드록시에틸메타크릴레이트 공중합체, 메타크릴산/벤질메타크릴레이트/스티렌/2-히드록시에틸메타크릴레이트 공중합체 등을 들 수 있으나, 이에 한정되는 것은 아니며, 이들을 단독 또는 2종 이상을 배합하여 사용할 수도 있다. Specific examples of the binder resin include a methacrylic acid / benzyl methacrylate copolymer, a methacrylic acid / benzyl methacrylate / styrene copolymer, a methacrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer , Methacrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, but are not limited thereto, and they may be used alone or in combination of two or more.
상기 바인더 수지의 중량평균 분자량은 3,000 g/mol 내지 150,000 g/mol, 예컨대 5,000 g/mol 내지 50,000 g/mol, 예컨대 20,000 g/mol 내지 30,000 g/mol일 수 있다. 바인더 수지의 중량평균 분자량이 상기의 범위일 때, 기판과의 밀착성이 우수하고 물리적, 화학적 물성이 좋으며, 점도가 적절하다. The weight average molecular weight of the binder resin may be from 3,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 20,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the binder resin is within the above range, it has good adhesion with the substrate, good physical and chemical properties, and good viscosity.
상기 바인더 수지의 산가는 15 mgKOH/g 내지 60 mgKOH/g, 예컨대 20 mgKOH/g 내지 50 mgKOH/g일 수 있다. 바인더 수지의 산가가 상기 범위 내일 경우 우수한 픽셀의 해상도를 얻을 수 있다.The acid value of the binder resin may be from 15 mgKOH / g to 60 mgKOH / g, such as from 20 mgKOH / g to 50 mgKOH / g. When the acid value of the binder resin is within the above range, excellent pixel resolution can be obtained.
상기 바인더 수지는 상기 감광성 수지 조성물 총량에 대하여 1 중량% 내지 10 중량%, 예컨대 1 중량% 내지 5 중량%로 포함될 수 있다. 바인더 수지가 상기 범위 내로 포함되는 경우 컬러필터 제조 시 현상성이 우수하며 가교성이 개선되어 우수한 표면 평활도를 얻을 수 있다. The binder resin may be included in an amount of 1 wt% to 10 wt%, for example, 1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition. When the binder resin is contained within the above range, the color filter is excellent in developability in the production of a color filter and the cross-linkability is improved, so that excellent surface smoothness can be obtained.
(C) (C) 광중합성Photopolymerization 단량체 Monomer
상기 광중합성 단량체는 적어도 1개의 에틸렌성 불포화 이중결합을 가지는 (메타)아크릴산의 일관능 또는 다관능 에스테르가 사용될 수 있다.The photopolymerizable monomer may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond.
상기 광중합성 단량체는 상기 에틸렌성 불포화 이중결합을 가짐으로써, 패턴 형성 공정에서 노광시 충분한 중합을 일으킴으로써 내열성, 내광성 및 내화학성이 우수한 패턴을 형성할 수 있다.Since the photopolymerizable monomer has the ethylenically unsaturated double bond, sufficient polymerization is caused during exposure in the pattern formation step, whereby a pattern having excellent heat resistance, light resistance and chemical resistance can be formed.
상기 광중합성 단량체의 구체적인 예로는, 에틸렌 글리콜디(메타)아크릴레이트, 디에틸렌글리콜디(메타)아크릴레이트, 트리에틸렌글리콜디(메타)아크릴레이트, 프로필렌글리콜디(메타)아크릴레이트, 네오펜틸글리콜디(메타)아크릴레이트, 1,4-부탄디올 디(메타)아크릴레이트, 1,6-헥산디올 디(메타)아크릴레이트, 비스페놀A 디(메타)아크릴레이트, 펜타에리트리톨디(메타)아크릴레이트, 펜타에리트리톨 트리(메타)아크릴레이트, 펜타에리트리톨테트라(메타)아크릴레이트, 펜타에리트리톨헥사(메타)아크릴레이트, 디펜타에리트리톨디(메타)아크릴레이트, 디펜타에리트리톨 트리(메타)아크릴레이트, 디펜타에리트리톨펜타(메타)아크릴레이트, 디펜타에리트리톨헥사(메타)아크릴레이트, 비스페놀A 에폭시(메타)아크릴레이트, 에틸렌 글리콜모노메틸에테르 (메타)아크릴레이트, 트리메틸올 프로판 트리(메타)아크릴레이트, 트리스(메타)아크릴로일옥시에틸포스페이트, 노볼락에폭시 (메타)아크릴레이트등을 들 수 있다. Specific examples of the photopolymerizable monomer include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol Acrylate such as di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (Meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl ether (Meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolak epoxy (meth) acrylate and the like.
상기 광중합성 단량체의 시판되는 제품을 예로 들면 다음과 같다. 상기 (메타)아크릴산의 일관능 에스테르의 예로는, 도아 고세이 가가꾸 고교(주)社의 아로닉스 M-101®, 동 M-111®, 동 M-114® 등; 니혼 가야꾸(주)社의 KAYARAD TC-110S®, 동 TC-120S® 등; 오사카 유끼 가가꾸 고교(주)社의 V-158®, V-2311® 등을 들 수 있다. 상기 (메타)아크릴산의 이관능 에스테르의 예로는, 도아 고세이 가가꾸 고교(주)社의 아로닉스 M-210®, 동 M-240®, 동 M-6200® 등; 니혼 가야꾸(주)社의 KAYARAD HDDA®, 동 HX-220®, 동 R-604® 등; 오사카 유끼 가가꾸 고교(주)社의 V-260®, V-312®, V-335 HP® 등을 들 수 있다. 상기 (메타)아크릴산의 삼관능 에스테르의 예로는, 도아 고세이 가가꾸 고교(주)社의 아로닉스 M-309®, 동 M-400®, 동 M-405®, 동 M-450®, 동 M-7100®, 동 M-8030®, 동 M-8060® 등; 니혼 가야꾸(주)社의 KAYARAD TMPTA®, 동 DPCA-20®, 동-30®, 동-60®, 동-120® 등; 오사카 유끼 가야꾸 고교(주)社의 V-295®, 동-300®, 동-360®, 동-GPT®, 동-3PA®, 동-400® 등을 들 수 있다. 상기 제품을 단독 사용 또는 2종 이상 함께 사용할 수 있다.A commercially available product of the photopolymerizable monomer is exemplified as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ®, the same M-111 ®, the same M-114 ®; KAYARAD TC-110S ® and TC-120S ® from Nihon Kayaku Co., Ltd.; Osaka yukki the like Kagaku Kogyo (main)社of V-158 ®, V-2311 ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ®, copper or the like M-240 ®, the same M-6200 ®; KAYARAD HDDA ® , HX-220 ® and R-604 ® from Nihon Kayaku Corporation; Osaka yukki the like Kagaku Kogyo Co., Ltd. of 社V-260 ®, V- 312 ®, V-335 HP ®. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ®, the same M-400 ®, the same M-405 ®, the same M-450 ®, Dong M -7100 ® , copper M-8030 ® , copper M-8060 ® and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ®, copper DPCA-20 ®, ® copper -30, -60 ® copper, copper ® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ®, copper ® -300, -360 ® copper, copper -GPT ®, copper -3PA ®, and the like copper -400 ®. These products may be used alone or in combination of two or more.
상기 광중합성 단량체는보다 우수한 현상성을 부여하기 위하여 산무수물로 처리하여 사용할 수도 있다.The photopolymerizable monomer may be treated with an acid anhydride to give better developing properties.
상기 광중합성 단량체는 상기 감광성 수지 조성물 총량에 대하여 5 중량% 내지 15 중량%, 예컨대 5 중량% 내지 10 중량%로 포함될 수 있다. 상기 광중합성 단량체가 상기 범위 내로 포함되는 경우 컬러필터 제조 시 패턴 특성 및 현상성이 우수하다.The photopolymerizable monomer may be included in an amount of 5 wt% to 15 wt%, for example, 5 wt% to 10 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerizable monomer is contained within the above range, pattern characteristics and developability are excellent in the production of a color filter.
(D) (D) 광중합Light curing 개시제Initiator
상기 광중합 개시제는 아세토페논계 화합물, 벤조페논계 화합물, 티오크산톤계 화합물, 벤조인계 화합물, 트리아진계 화합물, 옥심계 화합물 등을 사용할 수 있다.The photopolymerization initiator may be an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, or an oxime-based compound.
상기 아세토페논계의 화합물의 예로는, 2,2'-디에톡시 아세토페논, 2,2'-디부톡시 아세토페논, 2-히드록시-2-메틸프로피오페논, p-t-부틸트리클로로 아세토페논, p-t-부틸디클로로 아세토페논, 4-클로로 아세토페논, 2,2'-디클로로-4-페녹시 아세토페논, 2-메틸-1-(4-(메틸티오)페닐)-2-모폴리노프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-모폴리노페닐)-부탄-1-온 등을 들 수 있다.Examples of the acetophenone-based compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropanone, p-butyldichloroacetophenone, 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.
상기 벤조페논계 화합물의 예로는, 벤조페논, 벤조일 안식향산, 벤조일 안식향산 메틸, 4-페닐 벤조페논, 히드록시 벤조페논, 아크릴화 벤조페논, 4,4'-비스(디메틸 아미노)벤조페논, 4,4'-비스(디에틸아미노)벤조페논, 4,4'-디메틸아미노벤조페논,4,4'-디클로로벤조페논, 3,3'-디메틸-2-메톡시벤조페논 등을 들 수 있다.Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.
상기 티오크산톤계 화합물의 예로는, 티오크산톤, 2-메틸티오크산톤, 이소프로필 티오크산톤, 2,4-디에틸 티오크산톤, 2,4-디이소프로필 티오크산톤, 2-클로로티오크산톤 등을 들 수 있다.Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Chlorothioxanthone and the like.
상기 벤조인계 화합물의 예로는, 벤조인, 벤조인 메틸 에테르, 벤조인 에틸 에테르, 벤조인 이소프로필 에테르, 벤조인 이소부틸 에테르, 벤질디메틸케탈 등을 들 수 있다.Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
상기 트리아진계 화합물의 예로는, 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(트리클로로 메틸)-s-트리아진, 2-비페닐 4,6-비스(트리클로로 메틸)-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-트리 클로로메틸(피페로닐)-6-트리아진, 2-4-트리클로로메틸(4'-메톡시스티릴)-6-트리아진 등을 들 수 있다.Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho 1-yl) -4,6 -Bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphtho-1-yl) (Piperonyl) -6-triazine, and 2-4-trichloromethyl (4'-methoxystyryl) -6-triazine.
상기 옥심계 화합물의 예로는 O-아실옥심계화합물, 2-(O-벤조일옥심)-1-[4-(페닐티오)페닐]-1,2-옥탄디온, 1-(O-아세틸옥심)-1-[9-에틸-6-(2-메틸벤조일)-9H-카르바졸-3-일]에탄온, O-에톡시카르보닐-α-옥시아미노-1-페닐프로판-1-온등을사용할수있다. 상기 O-아실옥심계 화합물의 구체적인 예로는, 1,2-옥탄디온, 2-디메틸아미노-2-(4-메틸벤질)-1-(4-모르폴린-4-일-페닐)-부탄-1-온, 1-(4-페닐술파닐페닐)-부탄-1,2-디온-2-옥심-O-벤조에이트, 1-(4-페닐술파닐페닐)-옥탄-1,2-디온-2-옥심-O-벤조에이트, 1-(4-페닐술파닐페닐)-옥탄-1-온옥심-O-아세테이트, 1-(4-페닐술파닐페닐)-부탄-1-온옥심-O-아세테이트 등을 사용할 수 있다.Examples of the oxime compounds include O-acyloxime compounds, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- -9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- Can be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- 2-oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1,2-dione -1-one oxime-O-acetate, 1- (4-phenylsulfanylphenyl) -butan-1-one oxime- O-acetate and the like can be used.
상기 광중합 개시제는 상기 화합물 이외에도 카바졸계 화합물, 디케톤류 화합물, 술포늄 보레이트계 화합물, 디아조계 화합물, 이미다졸계 화합물, 비이미다졸계 화합물 등을 사용할 수 있다.The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.
상기 광중합 개시제는 상기 감광성 수지 조성물 총량에 대하여 0.1 중량% 내지 5 중량%, 예컨대 0.5 중량% 내지 3 중량%로 포함될 수 있다. 광중합 개시제가 상기 범위 내로 포함되는 경우 컬러필터 제조를 위한 패턴 형성 공정에서 노광 시 광중합이 충분히 일어나게 되어 감도가 우수하며, 투과율이 개선된다. The photopolymerization initiator may be included in an amount of 0.1 wt% to 5 wt%, for example, 0.5 wt% to 3 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, photopolymerization occurs sufficiently during exposure in the pattern formation process for producing a color filter, and the sensitivity is excellent and the transmittance is improved.
(E) 용매(E) Solvent
상기 용매는 특별한 제한은 없으나, 구체적으로 예를 들면, 메탄올, 에탄올 등의 알코올류; 디클로로에틸 에테르, n-부틸 에테르, 디이소아밀 에테르, 메틸페닐 에테르, 테트라히드로퓨란 등의 에테르류; 에틸렌 글리콜 메틸에테르, 에틸렌 글리콜 에틸에테르, 프로필렌 글리콜 메틸에테르 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; 프로필렌 글리콜 메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류; 톨루엔, 크실렌 등의 방향족 탄화수소류; 메틸에틸케톤, 사이클로헥사논, 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; 메틸 락테이트, 에틸 락테이트 등의 락트산 알킬 에스테르류; 메틸 히드록시아세테이트, 에틸 히드록시아세테이트, 부틸 히드록시아세테이트 등의 히드록시아세트산 알킬 에스테르류; 메톡시메틸 아세테이트, 메톡시에틸 아세테이트, 메톡시부틸 아세테이트, 에톡시메틸 아세테이트, 에톡시에틸 아세테이트 등의 아세트산 알콕시알킬 에스테르류; 메틸 3-히드록시프로피오네이트, 에틸 3-히드록시프로피오네이트 등의 3-히드록시프로피온산 알킬 에스테르류; 메틸 3-메톡시프로피오네이트, 에틸 3-메톡시프로피오네이트, 에틸 3-에톡시프로피오네이트, 메틸 3-에톡시프로피오네이트 등의 3-알콕시프로피온산 알킬 에스테르류; 메틸 2-히드록시프로피오네이트, 에틸 2-히드록시프로피오네이트, 프로필 2-히드록시프로피오네이트 등의 2-히드록시프로피온산 알킬 에스테르류; 메틸 2-메톡시프로피오네이트, 에틸 2-메톡시프로피오네이트, 에틸 2-에톡시프로피오네이트, 메틸 2-에톡시프로피오네이트 등의 2-알콕시프로피온산 알킬 에스테르류; 메틸 2-히드록시-2-메틸프로피오네이트, 에틸 2-히드록시-2-메틸프로피오네이트 등의 2-히드록시-2-메틸프로피온산 알킬 에스테르류; 메틸 2-메톡시-2-메틸프로피오네이트, 에틸 2-에톡시-2-메틸프로피오네이트 등의 2-알콕시-2-메틸프로피온산 알킬 에스테르류; 2-히드록시에틸 프로피오네이트, 2-히드록시-2-메틸에틸 프로피오네이트, 히드록시에틸 아세테이트, 메틸 2-히드록시-3-메틸부타노에이트 등의 에스테르류; 또는 피루빈산 에틸 등의 케톤산 에스테르류의 화합물이 있으며, 또한 N-메틸포름아미드, N,N-디메틸포름아미드, N-메틸포름아닐리드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드, 벤질에틸에테르, 디헥실에테르, 아세틸아세톤, 이소포론, 카프론산, 카프릴산, 1-옥탄올, 1-노난올, 벤질알코올, 초산 벤질, 안식향산 에틸, 옥살산 디에틸, 말레인산 디에틸, γ-부티로락톤, 에틸렌 카보네이트, 프로필렌 카보네이트, 페닐 셀로솔브 아세테이트 등이 있으며, 이들 단독으로 사용되거나 2종 이상을 혼합하여 사용할 수 있다.The solvent is not particularly limited, but specific examples thereof include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether and propylene glycol methyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid alkyl esters such as methyl lactate and ethyl lactate; Hydroxyacetic acid alkyl esters such as methylhydroxyacetate, ethylhydroxyacetate and butylhydroxyacetate; Alkoxyalkyl esters such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-hydroxypropionic acid alkyl esters such as methyl 3-hydroxypropionate and ethyl 3-hydroxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-hydroxypropionic acid alkyl esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate and propyl 2-hydroxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-hydroxy-2-methylpropionic acid alkyl esters such as methyl 2-hydroxy-2-methylpropionate and ethyl 2-hydroxy-2-methylpropionate; 2-alkoxy-2-methylpropionic acid alkyl esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; Esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate and methyl 2-hydroxy-3-methyl butanoate; Or ethyl pyruvate. Examples of the ketone acid esters include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, Ethyl, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc. These may be used alone or in combination of two or more.
상기 용매 중 혼화성(miscibility) 및 반응성 등을 고려한다면, 좋게는 에틸렌 글리콜 모노에틸 에테르 등의 글리콜 에테르류; 에틸 셀로솔브 아세테이트 등의 에틸렌 글리콜 알킬에테르 아세테이트류; 2-히드록시에틸 프로피오네이트 등의 에스테르류; 디에틸렌 글리콜 모노메틸 에테르 등의 디에틸렌 글리콜류; 프로필렌 글리콜 모노메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류가 사용될 수 있다. In view of the miscibility and reactivity of the solvent, glycol ethers such as ethylene glycol monoethyl ether and the like; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as 2-hydroxyethyl propionate; Diethylene glycol such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.
상기 용매는 상기 감광성 수지 조성물 총량에 대하여 잔부로 포함될 수 있으며, 예컨대 60 중량% 내지 80 중량%로 포함될 수 있다. 용매가 상기 범위 내로 포함되는 경우 감광성 수지 조성물의 도포성이 우수하고, 두께 3㎛ 이상의 막에서 우수한 평탄성을 유지할 수 있다.The solvent may be included as the balance relative to the total amount of the photosensitive resin composition, and may be, for example, from 60% by weight to 80% by weight. When the solvent is contained within the above range, the photosensitive resin composition is excellent in coating property and excellent flatness can be maintained in a film having a thickness of 3 m or more.
(F) 기타 첨가제(F) Other additives
상기 감광성 수지 조성물은 도포 시 얼룩이나 반점을 방지하고, 레벨링 성능을 개선하기 위해, 또한 미현상에 의한 잔사의 생성을 방지하기 위하여, 말론산; 3-아미노-1,2-프로판디올; 비닐기 또는 (메타)아크릴옥시기를 포함하는 실란계 커플링제; 레벨링제; 불소계 계면활성제; 라디칼 중합 개시제 등의 첨가제를 더 포함할 수 있다.The above-mentioned photosensitive resin composition may contain at least one selected from the group consisting of malonic acid, malonic acid, and malonic acid, in order to prevent spots and spots upon application, to improve the leveling performance, 3-amino-1,2-propanediol; A silane-based coupling agent comprising a vinyl group or (meth) acryloxy group; Leveling agents; Fluorine surfactants; A radical polymerization initiator, and the like.
또한 상기 감광성 수지 조성물은 기판과의 밀착성 등을 개선하기 위해, 에폭시 화합물 등의 첨가제를 더 포함할 수 있다.The above-mentioned photosensitive resin composition may further contain an additive such as an epoxy compound in order to improve the adhesion with the substrate.
상기 에폭시 화합물의 예로는, 페놀 노볼락 에폭시 화합물, 테트라메틸 비페닐 에폭시 화합물, 비스페놀 A형 에폭시 화합물, 지환족 에폭시 화합물 또는 이들의 조합을 들 수 있다.Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.
상기 첨가제의 함량은 원하는 물성에 따라 용이하게 조절될 수 있다.The content of the additive can be easily adjusted according to desired properties.
또 다른 일 구현예는 전술한 감광성 수지 조성물을 이용하여 제조된 컬러필터를 제공한다. 상기 컬러필터의 제조 방법은 다음과 같다. Another embodiment provides a color filter manufactured using the above-described photosensitive resin composition. A method of manufacturing the color filter is as follows.
아무 것도 도포되어 있지 않은 유리기판 위에, 또는 보호막인 SiNx가 500Å 내지 1500Å의 두께로 도포되어 있는 유리기판 위에, 전술한 컬러필터용 감광성 수지 조성물을 스핀 도포, 슬릿 도포 등의 적당한 방법을 사용하여, 1㎛ 내지 3㎛의 두께로 각각 도포한다. 도포 후에는 컬러필터에 필요한 패턴을 형성하도록 광을 조사한다. 광을 조사한 다음, 도포층을 알칼리 현상액으로 처리하면 도포층의 미조사 부분이 용해되고 컬러필터에 필요한 패턴이 형성된다. 이러한 과정을 필요한 R, G, B 색의 수에 따라 반복수행함으로써, 원하는 패턴을 갖는 컬러필터를 수득할 수 있다. The above-mentioned photosensitive resin composition for a color filter is applied onto a glass substrate to which nothing is applied or a glass substrate on which a protective film such as SiN x is applied to a thickness of 500 to 1500 ANGSTROM by a suitable method such as spin coating or slit coating , And 1 占 퐉 to 3 占 퐉, respectively. After the application, light is irradiated to form a pattern necessary for the color filter. After the light is irradiated and the coating layer is treated with an alkali developing solution, the unexposed portions of the coating layer are dissolved and a pattern necessary for the color filter is formed. By repeating this process according to the required number of R, G, and B colors, a color filter having a desired pattern can be obtained.
또한 상기 과정에서, 현상에 의해 수득된 화상 패턴을 다시 가열하거나 또는 활성선 조사 등에 의해 경화시킴으로써 내크랙성, 내용제성 등을 더욱 향상시킬 수 있다. In addition, in the above process, the image pattern obtained by development may be further heated or cured by actinic ray irradiation or the like to further improve crack resistance, solvent resistance, and the like.
이하, 본 발명의 바람직한 실시예를 기재한다. 다만, 하기의 실시예는 본 발명의 바람직한 일 실시예일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, preferred embodiments of the present invention will be described. However, the following examples are only a preferred embodiment of the present invention, and the present invention is not limited by the following examples.
(( 단분자Single molecule 화합물 제조) Compound Preparation)
(중간체 (Intermediate 합성예Synthetic example 1: 중간체 A-1의 합성) 1: Synthesis of intermediate A-1)
LC/MS : 333.56 m/z LC / MS: 333.56 < RTI ID = 0.0 > m / z
3-aminophenol (10 mol), 1-bromo-2-ethylhexane (20mmol)을 에탄올에 넣고 24시간동안 환류 시킨다. 감압하에서 용매를 제거하고 에틸 아세테이트를 넣고 물로 2회 세정하여 유기층을 추출하였다. 추출한 유기층을 감압 증류하고 컬럼 크로마토 그래피로 정제하여, 중간체A-1로 표시되는 화합물을 수득하였다.3-aminophenol (10 mol) and 1-bromo-2-ethylhexane (20 mmol) were added to ethanol and refluxed for 24 hours. The solvent was removed under reduced pressure, ethyl acetate was added, and the mixture was washed twice with water to extract an organic layer. The extracted organic layer was distilled under reduced pressure and purified by column chromatography to obtain a compound represented by Intermediate A-1.
(중간체 (Intermediate 합성예Synthetic example 2: 중간체 A-2의 합성) 2: Synthesis of intermediate A-2)
LC/MS : 745.15 m/zLC / MS: 745.15 < RTI ID = 0.0 > m / z
중간체A-1(60 mmol), 3,4-디하이드록시-3-사이클로부틴-1,2-다이온(30 mmol)을 톨루엔(200 mL) 및 부탄올(200 mL)에 넣고 환류하여 생성되는 물을 Dean-stark 증류장치로 제거한다. 12시간 동안 교반 후 녹색 반응물을 감압증류하고 컬럼 크로마토그래피로 정제하여, 중간체 A-2로 표시되는 화합물을 수득하였다.Intermediate A-1 (60 mmol) and 3,4-dihydroxy-3-cyclobutyne-1,2-dione (30 mmol) were added to toluene (200 mL) and butanol The water is removed with a Dean-stark distillation apparatus. After stirring for 12 hours, the green reaction product was distilled under reduced pressure and purified by column chromatography to obtain a compound represented by Intermediate A-2.
(( 합성예Synthetic example 1: 화학식 1-1의 합성) 1: Synthesis of Formula 1-1)
중간체 A-2(10mol), phenylisocyanate(10mol)을 디클로로메탄에 넣고 Bu2Sn dilaurate를 촉매량 첨가한다. 40℃에서 24시간 동안 교반후 감압 하에 용매를 제거하고 컬럼 크로마토그래피로 정제하여, 화학식 1-1로 표시되는 화합물을 수득하였다. Intermediate A-2 (10 mol) and phenylisocyanate (10 mol) are added to dichloromethane and a catalytic amount of Bu 2 Sn dilaurate is added. After stirring at 40 DEG C for 24 hours, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the compound represented by formula (1-1).
Maldi-tof MS : 863.62 m/zMald-tof MS: 863.62 m / z
(( 합성예Synthetic example 2: 화학식 1-2의 합성) 2: Synthesis of Formulas 1-2)
Phenyl isocyanate 대신 cyclohexyl isocyanate를 사용한 것을 제외하고는 합성예 1과 동일한 방법으로 합성하여 화학식 1-2로 표시되는 화합물을 수득하였다. Synthesis was conducted in the same manner as in Synthesis Example 1 except that cyclohexyl isocyanate was used instead of phenyl isocyanate to obtain a compound represented by Formula 1-2.
Maldi-tof MS : 869.66m/zMald-tof MS: 869.66 m / z
(( 합성예Synthetic example 3: 화학식 1-3의 합성) 3: Synthesis of Formulas 1-3)
Phenyl isocyanate 대신 isopropyl isocyanate를 사용한 것을 제외하고는 합성예 1과 동일한 방법으로 합성하여 화학식 1-3으로 표시되는 화합물을 수득하였다. Was synthesized in the same manner as in Synthesis Example 1 except that isopropyl isocyanate was used instead of phenyl isocyanate to obtain a compound represented by Formula 1-3.
Maldi-tof MS : 829.63 m/zMald-tof MS: 829.63 m / z
(( 합성예Synthetic example 4: 화학식 1-4의 합성) 4: Synthesis of Formulas 1-4)
Phenyl isocyanate 대신 3-(Triethoxysilyl)propyl Isocyanate를 사용한 것을 제외하고는 합성예 1과 동일한 방법으로 합성하여 화학식 1-4로 표시되는 화합물을 수득하였다. Was synthesized in the same manner as in Synthesis Example 1 except that 3- (Triethoxysilyl) propyl Isocyanate was used instead of Phenyl isocyanate to obtain a compound represented by Formula 1-4.
Maldi-tof MS : 991.70 m/zMald-tof MS: 991.70 m / z
(( 합성예Synthetic example 5: 화학식 1-5의 합성) 5: Synthesis of Formulas 1-5)
Phenyl isocyanate 대신 Methacryloyloxyethyl isocyanate를 사용한 것을 제외하고는 합성예 1과 동일한 방법으로 합성하여 화학식 1-5로 표시되는 화합물을 수득하였다. Was synthesized in the same manner as in Synthesis Example 1 except that methacryloyloxyethyl isocyanate was used instead of phenyl isocyanate to obtain a compound represented by Formula 1-5.
Maldi-tof MS : 899.64 m/zMaldi-tof MS: 899.64 m / z
(( 합성예Synthetic example 6: 화학식 1-6의 합성) 6: Synthesis of 1-6)
Phenyl isocyanate 대신 Benzyl isocyanate를 사용한 것을 제외하고는 합성예 1과 동일한 방법으로 합성하여 화학식 1-6으로 표시되는 화합물을 수득하였다. Was synthesized in the same manner as in Synthesis Example 1 except that benzyl isocyanate was used instead of phenyl isocyanate to obtain the compound represented by Formula 1-6.
Maldi-tof MS : 877.63 m/zMald-tof MS: 877.63 m / z
(( 합성예Synthetic example 7: 화학식 1-7의 합성) 7: Synthesis of 1-7)
Phenyl isocyanate 대신 1-Adamantyl Isocyanate를 사용한 것을 제외하고는 합성예 1과 동일한 방법으로 합성하여 화학식 1-7로 표시되는 화합물을 수득하였다. Was synthesized in the same manner as in Synthesis Example 1 except that 1-Adamantyl Isocyanate was used instead of Phenyl isocyanate to obtain a compound represented by Formula 1-7.
Maldi-tof MS : 921.70 m/zMaldi-tof MS: 921.70 m / z
(( 비교합성예Comparative Synthetic Example 1: 화학식 C-1로 표시되는 화합물의 합성) 1: Synthesis of the compound represented by the formula C-1)
100mL 3-목 플라스크에 스쿠아린산 398mg, N-(3-디부틸아미노)페닐아세트아마이드 및 3-(디에틸아미노)페놀 2.23g을 넣은 후 n-부탄올 40mL 및 톨루엔 20mL를 첨가하고 120℃에서 5시간 동안 가열 환류하였다. 딘스타크 트랩 세트(DeanStark trap set)를 이용하여 반응 중 발생하는 물을 제거하고 반응을 촉진시켰다. 반응 종료 후 냉각하고, 메틸렌 클로라이드로 추출한 후 컬럼 크로마토그래피하여 하기 화학식 C-1로 표시되는 화합물을 60% 수율로 제조하였다.After adding 398 mg of squaric acid, 2.23 g of N- (3-dibutylamino) phenylacetamide and 3- (diethylamino) phenol, 40 mL of n-butanol and 20 mL of toluene was added to a 100 mL three- The mixture was heated under reflux for 5 hours. A DeanStark trap set was used to remove water generated during the reaction and to promote the reaction. After completion of the reaction, the reaction mixture was cooled, extracted with methylene chloride, and then subjected to column chromatography to obtain the compound represented by the following formula (C-1) in a yield of 60%.
[화학식 C-1][Chemical formula C-1]
Maldi-tof MS : 505.29 m/zMald-tof MS: 505.29 m / z
(( 비교합성예Comparative Synthetic Example 2: 화학식 C-2로 표시되는 화합물의 합성) 2: Synthesis of the compound represented by the formula C-2)
3-아미노페놀 10.9 중량부에, 트리에톡시실란 19 중량부 및 아세트산 5 중량부를, 테트라히드로푸란 200 중량부 속에서, 8시간 동안 환류하였다. 반응 종료 후, 테트라히드로푸란을 증류 제거하여 화합물을 수득하였다. 상기 수득한 화합물 2.9 중량부, 3,4-디히드록시-3-시클로부텐-1,2-디온 0.6 중량부, 1-부탄올 90 중량부 및 톨루엔 60 중량부를 혼합하였다. 얻어진 혼합물을, Dean-Stark관을 이용하여 생성된 물을 제거하면서 125℃에서 3시간 동안 교반하였다.반응 종료 후, 용매를 증류 제거하고, 아세트산을 15 중량부 첨가한 후, 18% 식염수를 적하하고, 석출된 고체를 여과하여 취하였다. 여과하여 취한 고체를 헥산으로 세정하였다. 얻어진 고체를 감압 건조시켜, 하기 화학식 C-2로 표시되는 화합물 3.4 중량부를 얻었다.To 10.9 parts by weight of 3-aminophenol, 19 parts by weight of triethoxysilane and 5 parts by weight of acetic acid were refluxed in 200 parts by weight of tetrahydrofuran for 8 hours. After completion of the reaction, tetrahydrofuran was distilled off to obtain a compound. 2.9 parts by weight of the compound obtained above, 0.6 part by weight of 3,4-dihydroxy-3-cyclobutene-1,2-dione, 90 parts by weight of 1-butanol and 60 parts by weight of toluene were mixed. After the completion of the reaction, the solvent was distilled off, 15 parts by weight of acetic acid was added, and 18% saline was added dropwise to the reaction mixture And the precipitated solid was filtered off. The solid was filtered off and washed with hexane. The resulting solid was dried under reduced pressure to obtain 3.4 parts by weight of a compound represented by the following formula (C-2).
[화학식 C-2][Chemical formula C-2]
LC-MS : 679.3 m/zLC-MS: 679.3 m / z
(감광성 수지 조성물 제조)(Preparation of photosensitive resin composition)
감광성 수지 조성물 제조에 사용되는 성분의 사양은 다음과 같다.The specifications of the components used in the production of the photosensitive resin composition are as follows.
(A) 염료(A) Dye
(A-1) 합성예 1에서 제조된 화합물(화학식 1-1로 표시)(A-1) The compound prepared in Synthesis Example 1 (represented by Formula 1-1)
(A-2) 합성예 2에서 제조된 화합물(화학식 1-2로 표시)(A-2) The compound prepared in Synthesis Example 2 (represented by Formula 1-2)
(A-3) 합성예 3에서 제조된 화합물(화학식 1-3으로 표시)(A-3) The compound prepared in Synthesis Example 3 (represented by Formula 1-3)
(A-4) 합성예 4에서 제조된 화합물(화학식 1-4로 표시)(A-4) The compound prepared in Synthesis Example 4 (represented by Formula 1-4)
(A-5) 합성예 5에서 제조된 화합물(화학식 1-5로 표시)(A-5) The compound prepared in Synthesis Example 5 (represented by Formula 1-5)
(A-6) 합성예 6에서 제조된 화합물(화학식 1-6로 표시)(A-6) The compound prepared in Synthesis Example 6 (represented by Formula 1-6)
(A-7) 합성예 7에서 제조된 화합물(화학식 1-7로 표시)(A-7) The compound prepared in Synthesis Example 7 (represented by Formula 1-7)
(A-8) 비교합성예1에서 제조된 화합물(화학식 C-1로 표시)(A-8) The compound prepared in Comparative Synthesis Example 1 (represented by the formula C-1)
(A-9) 비교합성예 2에서 제조된 화합물(화학식 C-2로 표시)(A-9) The compound prepared in Comparative Synthesis Example 2 (represented by the formula C-2)
(A') 안료 분산액(A ') Pigment dispersion
(A'-1) C.I. 녹색 안료 58(A'-1) C.I. Green pigment 58
(A'-2) C.I. 녹색 안료 36(A'-2) C.I. Green Pigment 36
(A'-3) C.I. 황색 안료 138(A'-3) C.I. Yellow pigment 138
(B) 바인더 수지(B) binder resin
중량평균분자량이 22,000 g/mol인 메타크릴산/벤질메타크릴레이트 공중합체(혼합 중량비 15wt%/85wt%)Methacrylic acid / benzyl methacrylate copolymer having a weight average molecular weight of 22,000 g / mol (mixing weight ratio 15wt% / 85wt%),
(C) (C) 광중합성Photopolymerization 단량체 Monomer
디펜타에리트리톨헥사아크릴레이트Dipentaerythritol hexaacrylate
(D) (D) 광중합Light curing 개시제Initiator
(D-1) 1,2-옥탄디온(D-1) 1,2-octanedione
(D-2) 2-디메틸아미노-2-(4-메틸-벤질)-1-(4-모르폴린-4-일-페닐)-부탄-1-온(D-2) To a solution of 2-dimethylamino-2- (4-methyl-benzyl)
(E) 용매(E) Solvent
(E-1) 사이클로헥사논(E-1) cyclohexanone
(E-2) 프로필렌글리콜 메틸에테르아세테이트(E-2) Propylene glycol methyl ether acetate
실시예Example 1 내지 1 to 실시예Example 7 및 7 and 비교예Comparative Example 1 내지 1 to 비교예Comparative Example 4 4
하기 표 1 내지 표 3의 조성으로 각 성분을 혼합하여 감광성 수지 조성물을 제조하였다. 구체적으로는, 용매에 광중합 개시제를 용해시킨 후 2시간 동안 상온에서 교반한 후, 염료(또는 안료분산액)를 투입하여 30분 간 교반한 후, 바인더 수지와 광중합성 단량체를 첨가하여 2시간 동안 상온에서 교반하였다. 상기 용액에 대하여 3회에 걸친 여과를 행하여 불순물을 제거하여 감광성 수지 조성물을 제조하였다. Each component was mixed with the compositions shown in Tables 1 to 3 below to prepare a photosensitive resin composition. Specifically, a photopolymerization initiator was dissolved in a solvent and stirred for 2 hours at room temperature. Then, a dye (or a pigment dispersion) was added thereto and stirred for 30 minutes. Then, a binder resin and a photopolymerizable monomer were added thereto. Lt; / RTI > The solution was filtered three times to remove impurities to prepare a photosensitive resin composition.
(평가)(evaluation)
휘도 및 명암비 평가Evaluation of luminance and contrast ratio
탈지 세척한 두께 1mm의 유리 기판 상에 1㎛ 내지 3㎛의 두께로 실시예 1 내지 실시예 7 및 비교예 1 내지 비교예 4에서 제조한 감광성 수지조성물을 도포하고, 90℃의 핫플레이트 상에서 2분 동안 건조시켜 도막을 수득하였다. 계속해서 도막에 365nm의 주파장을 가진 고압수은램프를 사용하여 노광한 후, 200℃의 열풍 순환식 건조로 안에서 5분 동안 건조시켰다. 화소층은 분광광도계(MCPD3000, Otsuka electronic社)를 이용하여 색좌표, 휘도 및 명암비를 측정하였고, 그 결과를 하기 표 3에 나타내었다.The photosensitive resin composition prepared in Examples 1 to 7 and Comparative Examples 1 to 4 was coated on a 1 mm thick glass substrate having a thickness of 1 탆 to 3 탆 and heat-treated on a hot plate at 90 캜 for 2 Min to obtain a coating film. Subsequently, the coated film was exposed using a high-pressure mercury lamp having a main wavelength of 365 nm, and then dried in a hot-air circulating drying oven at 200 ° C for 5 minutes. The color layer was measured for color coordinates, brightness and contrast ratio using a spectrophotometer (MCPD3000, Otsuka electronic Co.), and the results are shown in Table 3 below.
상기 표 3으로부터, 일 구현예에 따른 화합물을 포함하는 실시예 1 내지 실시예 7의 경우, 상기 화합물을 포함하지 않는 비교예 1 내지 비교예 4의 경우와 비교하여, 휘도 및 명암비가 우수함을 확인할 수 있다.From Table 3, it can be seen that Examples 1 to 7 containing the compound according to one embodiment have superior luminance and contrast ratio as compared with Comparative Examples 1 to 4 which do not contain the compound .
본 발명은 상기 실시예들에 한정되는 것이 아니라 서로 다른 다양한 형태로 제조될 수 있으며, 본 발명이 속하는 기술분야에서 통상의 지식을 가진 자는 본 발명의 기술적 사상이나 필수적인 특징을 변경하지 않고서 다른 구체적인 형태로 실시될 수 있다는 것을 이해할 수 있을 것이다. 그러므로 이상에서 기술한 실시예들은 모든 면에서 예시적인 것이며 한정적이 아닌 것으로 이해해야만 한다.It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.
Claims (17)
[화학식 1]
상기 화학식 1에서,
R1 내지 R4는 각각 독립적으로 수소 원자 또는 하기 화학식 2로 표시되는 치환기이고, 단 상기 R1 내지 R4 중 어느 하나는 반드시 하기 화학식 2로 표시되는 치환기이고,
[화학식 2]
상기 화학식 2에서,
L1은 단일결합 또는 치환 또는 비치환된 C1 내지 C10 알킬렌기이고,
R13은 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기, 치환 또는 비치환된 C6 내지 C20 아릴기, 치환 또는 비치환된 아크릴레이트기, 치환 또는 비치환된 실란기 또는 치환 또는 비치환된 C10 내지 C20 융합고리기이고,
R5 내지 R8은 각각 독립적으로 수소 원자 또는 히드록시기이고, 단 상기 R5 내지 R8 중 어느 하나는 반드시 히드록시기이고,
R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다.
A compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
R 1 to R 4 are each independently a hydrogen atom or a substituent represented by the following formula (2), provided that any one of R 1 to R 4 is a substituent represented by the following formula (2)
(2)
In Formula 2,
L 1 is a single bond or a substituted or unsubstituted C1 to C10 alkylene group,
R 13 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted acrylate group, a substituted or unsubstituted silane Or a substituted or unsubstituted C10 to C20 fused ring group,
R 5 to R 8 are each independently a hydrogen atom or a hydroxy group, provided that any one of R 5 to R 8 is a hydroxy group,
R 9 to R 12 each independently represent a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C20 aryl group.
상기 R1은 상기 화학식 2로 표시되는 화합물.
The method according to claim 1,
And R < 1 >
상기 R5는 히드록시기인 화합물.
3. The method of claim 2,
Wherein R < 5 > is a hydroxy group.
상기 치환 또는 비치환된 아크릴레이트기는 하기 화학식 3으로 표시되는 화합물:
[화학식 3]
상기 화학식 3에서,
R14는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이다.
The method according to claim 1,
Wherein the substituted or unsubstituted acrylate group is a compound represented by the following general formula (3):
(3)
In Formula 3,
R 14 is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
상기 치환 또는 비치환된 실란기는 하기 화학식 4로 표시되는 화합물:
[화학식 4]
상기 화학식 4에서,
R15 내지 R17은 각각 독립적으로 치환 또는 비치환된 C1 내지 C10 알킬기이다.
The method according to claim 1,
Wherein the substituted or unsubstituted silane group is represented by the following general formula (4):
[Chemical Formula 4]
In Formula 4,
R 15 to R 17 are each independently a substituted or unsubstituted C1 to C10 alkyl group.
상기 치환 또는 비치환된 C10 내지 C20 융합고리기는 아다만틸(ADAMANTYL)기인 화합물.
The method according to claim 1,
Wherein the substituted or unsubstituted C10 to C20 fused ring group is an adamantyl group.
상기 화학식 1로 표시되는 화합물은 하기 화학식 5로 표시되는 화합물:
[화학식 5]
상기 화학식 5에서,
L1은 단일결합 또는 치환 또는 비치환된 C1 내지 C10 알킬렌기이고,
R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C3 내지 C20 사이클로알킬기 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고,
R18은 하기 화학식 5-1 내지 화학식 5-7 중 어느 하나로 표시되고,
[화학식 5-1]
[화학식 5-2]
[화학식 5-3]
[화학식 5-4]
[화학식 5-5]
[화학식 5-6]
[화학식 5-7]
상기 화학식 5-1 내지 화학식 5-4 및 화학식 5-6에서,
R19는 할로겐 원자, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C1 내지 C10 알콕시기, *-C(=O)ORx 또는 *-OC(=O)Rx이고, 상기 Rx는 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,
Ry 및 Rz는 각각 독립적으로 수소 원자 또는 치환 또는 비치환된 C1 내지 C10 알킬기이고,
R20 내지 R22는 각각 독립적으로 치환 또는 비치환된 C1 내지 C8 알킬기이고,
p1은 0 내지 5의 정수이다.
The method according to claim 1,
The compound represented by Formula 1 is a compound represented by Formula 5:
[Chemical Formula 5]
In Formula 5,
L 1 is a single bond or a substituted or unsubstituted C1 to C10 alkylene group,
R 9 to R 12 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group or a substituted or unsubstituted C6 to C20 aryl group,
R 18 is represented by any one of the following formulas (5-1) to (5-7)
[Formula 5-1]
[Formula 5-2]
[Formula 5-3]
[Formula 5-4]
[Formula 5-5]
[Formula 5-6]
[Formula 5-7]
In the above Formulas 5-1 to 5-4 and 5-6,
R 19 represents a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, -C (= O) OR x or -OC (= O) R x , x is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R y and R z are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R 20 to R 22 are each independently a substituted or unsubstituted C1 to C8 alkyl group,
p1 is an integer of 0 to 5;
상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 내지 화학식 1-7로 이루어진 군에서 선택된 어느 하나로 표시되는 화합물.
[화학식 1-1]
[화학식 1-2]
[화학식 1-3]
[화학식 1-4]
[화학식 1-5]
[화학식 1-6]
[화학식 1-7]
The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (1-1) to (1-7).
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
[Formula 1-4]
[Formula 1-5]
[Chemical Formula 1-6]
[Chemical Formula 1-7]
9. A photosensitive resin composition comprising the compound of any one of claims 1 to 8.
상기 화합물은 염료인 감광성 수지 조성물.
10. The method of claim 9,
Wherein the compound is a dye.
상기 염료는 녹색 염료인 감광성 수지 조성물.
11. The method of claim 10,
Wherein the dye is a green dye.
상기 감광성 수지 조성물은 바인더 수지, 광중합성 단량체, 광중합 개시제 및 용매를 더 포함하는 감광성 수지 조성물.
10. The method of claim 9,
Wherein the photosensitive resin composition further comprises a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.
상기 감광성 수지 조성물은 안료를 더 포함하는 감광성 수지 조성물.
13. The method of claim 12,
Wherein the photosensitive resin composition further comprises a pigment.
상기 안료는 상기 감광성 수지 조성물 총량에 대해 10 중량% 내지 20 중량%로 포함되는 감광성 수지 조성물.
14. The method of claim 13,
Wherein the pigment is contained in an amount of 10% by weight to 20% by weight based on the total amount of the photosensitive resin composition.
상기 감광성 수지 조성물은, 감광성 수지 조성물 총량에 대해,
상기 화합물 1 중량% 내지 10 중량%;
상기 바인더 수지 1 중량% 내지 10 중량%;
상기 광중합성 단량체 5 중량% 내지 15 중량%;
상기 광중합 개시제 0.1 중량% 내지 5 중량%; 및
상기 용매 잔부량
을 포함하는 감광성 수지 조성물.
13. The method of claim 12,
The photosensitive resin composition preferably contains, relative to the total amount of the photosensitive resin composition,
1% to 10% by weight of the compound;
1% by weight to 10% by weight of the binder resin;
5% to 15% by weight of the photopolymerizable monomer;
0.1% by weight to 5% by weight of the photopolymerization initiator; And
The solvent balance
.
상기 감광성 수지 조성물은 말론산, 3-아미노-1,2-프로판디올,비닐기 또는 (메타)아크릴옥시기를 포함하는 실란계 커플링제, 레벨링제, 계면활성제, 라디칼 중합 개시제 또는 이들의 조합을 더 포함하는 감광성 수지 조성물.
13. The method of claim 12,
The photosensitive resin composition may further include a silane coupling agent comprising malonic acid, 3-amino-1,2-propanediol, a vinyl group or a (meth) acryloxy group, a leveling agent, a surfactant, a radical polymerization initiator, .
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| US6836383B1 (en) * | 2000-09-04 | 2004-12-28 | Mitsubishi Chemical Corporation | Diphenylsquarylium compound and filter for display containing the same |
| KR101413072B1 (en) * | 2011-12-22 | 2014-07-09 | 제일모직 주식회사 | Photosensitive resin composition for color filter and color filter using the same |
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| US6836383B1 (en) * | 2000-09-04 | 2004-12-28 | Mitsubishi Chemical Corporation | Diphenylsquarylium compound and filter for display containing the same |
| KR101413072B1 (en) * | 2011-12-22 | 2014-07-09 | 제일모직 주식회사 | Photosensitive resin composition for color filter and color filter using the same |
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