TW201527439A - Novel compound and composition containing novel compound - Google Patents
Novel compound and composition containing novel compound Download PDFInfo
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- TW201527439A TW201527439A TW103142228A TW103142228A TW201527439A TW 201527439 A TW201527439 A TW 201527439A TW 103142228 A TW103142228 A TW 103142228A TW 103142228 A TW103142228 A TW 103142228A TW 201527439 A TW201527439 A TW 201527439A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 185
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 24
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
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- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 235000013799 ultramarine blue Nutrition 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
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- C—CHEMISTRY; METALLURGY
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- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
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- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
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- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/086—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines more than five >CH- groups
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- C09B23/14—Styryl dyes
- C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
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Abstract
Description
本發明係關於一種具有酚系抗氧化劑結構之有機色素化合物、及含有該化合物之組合物。進而係關於一種使用該組合物之可藉由能量線進行聚合之著色感光性組合物及使用該著色感光性組合物之彩色濾光片。 The present invention relates to an organic dye compound having a phenolic antioxidant structure, and a composition containing the same. Further, it relates to a colored photosensitive composition which can be polymerized by an energy ray using the composition, and a color filter using the colored photosensitive composition.
對特定之光具有強度較大之吸收之化合物可用作CD-R(Compact Disc-Recordable,可錄式光碟)、DVD-R(Digital Versatile Disc-Recordable,可錄式數位多功能光碟)、DVD+R(Digital Versatile Disc+Recordable,可讀寫數位多功能光碟)、BD-R(Blue-ray Disc Recordable,可錄式藍光光碟)等光學記錄媒體之記錄層、或液晶顯示裝置(LCD)、電漿顯示面板(PDP)、電致發光顯示器(ELD)、陰極射線管顯示裝置(CRT)、螢光顯示管、場發射顯示器等圖像顯示裝置之光學元件。 A compound having a strong absorption for a specific light can be used as a CD-R (Compact Disc-Recordable, recordable optical disc), a DVD-R (Digital Versatile Disc-Recordable, a recordable digital versatile disc), a DVD +R (Digital Versatile Disc+Recordable), recording layer of optical recording medium such as BD-R (Blue-ray Disc Recordable), or liquid crystal display (LCD), An optical element of an image display device such as a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display device (CRT), a fluorescent display tube, or a field emission display.
於液晶顯示裝置(LCD)、電漿顯示面板(PDP)、電致發光顯示器(ELD)、陰極射線管顯示裝置(CRT)、螢光顯示管、場發射顯示器等圖像顯示裝置用之光學濾光片中,吸收300~1100nm波長之光之各種化合物係用作光吸收劑。 Optical filter for image display devices such as liquid crystal display (LCD), plasma display panel (PDP), electroluminescent display (ELD), cathode ray tube display (CRT), fluorescent display tube, field emission display, etc. In the light sheet, various compounds that absorb light having a wavelength of 300 to 1100 nm are used as a light absorber.
對於該等光吸收劑要求光吸收特別陡峭,即λmax之半值寬較小,又不會因光或熱等而喪失功能。 For these light absorbers, the light absorption is required to be particularly steep, that is, the half value width of λmax is small, and the function is not lost due to light or heat.
主要用於液晶顯示裝置(LCD)之光學濾光片有彩色濾光片。彩色 濾光片通常係使用RGB(Red Green Blue,紅綠藍)之三原色,但單獨之有色材料難以具有純粹之RGB之色相,而進行使用複數種有色材料來接近純粹之RGB之色相的努力。因此,亦必須黃色、橙色、紫色等而並非RGB之有色材料。 Optical filters mainly used for liquid crystal display devices (LCDs) have color filters. color The filter usually uses three primary colors of RGB (Red Green Blue), but it is difficult for a single colored material to have a pure RGB hue, and an effort is made to use a plurality of colored materials to approach a pure RGB hue. Therefore, it is also necessary to use yellow, orange, purple, etc. instead of RGB colored materials.
彩色濾光片所使用之光吸收劑出於耐熱性較高之原因使用有機及/或無機顏料,但有因係顏料而使作為顯示裝置之亮度降低之問題,此前係藉由提高光源之亮度而解決該問題。然而,伴隨著低耗電化之趨勢,而開始盛行使用染料之彩色濾光片之開發。 The light absorbing agent used for the color filter uses organic and/or inorganic pigments for reasons of high heat resistance, but has a problem of lowering the brightness of the display device due to the pigment, and previously by increasing the brightness of the light source And solve the problem. However, along with the trend of low power consumption, the development of color filters using dyes has begun.
進而近年來,固體攝像元件所使用之彩色濾光片就畫質提高之觀點而言,要求著色圖案之薄膜化,為了進行薄膜化,就色濃度之方面而言,必須提高染料濃度。又,於染料之莫耳吸光係數較低之情形時,亦必須添加大量之染料。 Further, in recent years, from the viewpoint of improving the image quality of the color filter used in the solid-state image sensor, it is required to thin the coloring pattern, and in order to perform film formation, it is necessary to increase the dye concentration in terms of color density. Moreover, in the case where the molar absorption coefficient of the dye is low, a large amount of dye must also be added.
然而,若提高染料濃度,則於成膜後實施加熱處理(後烘烤)之情形時,容易於鄰接像素間或積層構造中之上下層間產生混色,因此要求耐熱性。 However, when the dye concentration is increased, when heat treatment (post-baking) is performed after film formation, it is easy to cause color mixture between adjacent pixels or between the upper and lower layers in the laminated structure, and therefore heat resistance is required.
於專利文獻1~3中揭示有含有特定結構之有機色素之彩色濾光片用著色樹脂組合物。 Patent Literatures 1 to 3 disclose a colored resin composition for a color filter containing an organic dye having a specific structure.
又,於專利文獻4及5中揭示有含有色素與抗氧化劑之彩色濾光片用著色組合物。 Further, Patent Documents 4 and 5 disclose coloring compositions for color filters containing a dye and an antioxidant.
然而,該等文獻所記載之彩色濾光片用著色組合物所使用之化合物並非於耐熱性之方面可令人滿意者。 However, the compounds used in the coloring composition for color filters described in these documents are not satisfactory in terms of heat resistance.
專利文獻1:WO2012/039286 Patent Document 1: WO2012/039286
專利文獻2:WO2012/101946 Patent Document 2: WO2012/101946
專利文獻3:WO2012/111400 Patent Document 3: WO2012/111400
專利文獻4:日本專利特開2010-008650號公報 Patent Document 4: Japanese Patent Laid-Open Publication No. 2010-008650
專利文獻5:日本專利特開2011-141356號公報 Patent Document 5: Japanese Patent Laid-Open Publication No. 2011-141356
因此,本發明之目的在於提供一種耐熱性優異之著色感光性組合物(著色鹼顯影性感光性組合物)。又,本發明之另一目的在於提供一種使用上述著色感光性組合物(著色鹼顯影性感光性組合物)之光學濾光片,尤其是不使亮度降低、適合於液晶顯示面板等圖像顯示裝置之彩色濾光片。 Therefore, an object of the present invention is to provide a coloring photosensitive composition (colored alkali-developable photosensitive composition) which is excellent in heat resistance. Moreover, another object of the present invention is to provide an optical filter using the above-described colored photosensitive composition (colored alkali-developable photosensitive composition), and particularly suitable for image display such as a liquid crystal display panel without lowering the brightness. Color filter for the device.
本發明者反覆銳意研究,結果發現,具有特定結構之化合物之耐熱性優異,又發現,使用該化合物之著色感光性組合物(著色鹼顯影性感光性組合物)不使光學濾光片(尤其是彩色濾光片)之亮度降低,適合於液晶顯示面板等圖像顯示裝置用彩色濾光片,從而完成本發明。 The inventors of the present invention have conducted intensive studies and found that the compound having a specific structure is excellent in heat resistance, and it has been found that the coloring photosensitive composition (colored alkali-developable photosensitive composition) using the compound does not make an optical filter (especially The color filter is reduced in brightness and is suitable for a color filter for an image display device such as a liquid crystal display panel, thereby completing the present invention.
本發明係基於上述見解而完成者,提供一種化合物,其係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有1~10個下述通式(1)所表示之取代基。 The present invention has been completed based on the above findings, and provides a compound having an absorption maximum value of an organic dye in a wavelength range from ultraviolet to near-infrared, and having 1 to 10 molecules represented by the following formula (1) in the molecule. Substituent.
(式中,R01、R02、R03、R04及R05分別獨立表示氫原子、鹵素原 子、氰基、羥基、硝基、羧基、碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳烷基、碳原子數2~20之含雜環之基或-O-R1,R01、R02、R03、R04及R05中之至少一者由-O-R1表示,R1表示氫原子、碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳烷基、碳原子數2~20之含雜環之基或三烷基矽烷基,R01、R02、R03、R04及R05以及R1所表示之烷基、芳基、芳烷基或含雜環之基可具有取代基或者未經取代,R01、R02、R03、R04及R05以及R1所表示之烷基或芳烷基中之亞甲基可被取代為碳-碳雙鍵、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR2-、>P=O、-S-S-或-SO2-,R2表示氫原子或碳原子數1~8之烷基) (wherein R 01 , R 02 , R 03 , R 04 and R 05 each independently represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an alkyl group having 1 to 40 carbon atoms, and a carbon number An aryl group of 6 to 20, an aralkyl group having 7 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, or -OR 1 , R 01 , R 02 , R 03 , R 04 and R 05 At least one of them is represented by -OR 1 , and R 1 represents a hydrogen atom, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and a carbon number. a heterocyclic group or a trialkylsulfanyl group of 2 to 20, an alkyl group, an aryl group, an arylalkyl group or a heterocyclic ring represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 The substituent may be substituted or unsubstituted, and the methylene group in the alkyl group or the aralkyl group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 may be substituted with a carbon-carbon double bond. , -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO- O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR 2 -, >P=O, -SS- or -SO 2 -, R 2 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms)
又,本發明提供一種組合物,其含有上述化合物,該化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有1~10個下述通式(1)所表示之取代基。 Further, the present invention provides a composition comprising the above compound, which is an organic dye having an absorption maximum value in a wavelength region from ultraviolet to near-infrared, and having 1 to 10 following formula (1) in a molecule. Represents a substituent.
又,本發明提供一種著色感光性組合物,其於上述組合物中進而含有具有酸值之具有乙烯性不飽和鍵之聚合性化合物及光自由基聚合起始劑。 Moreover, the present invention provides a coloring photosensitive composition which further contains a polymerizable compound having an acid value and an ethylenically unsaturated bond and a photoradical polymerization initiator in the composition.
含有具有特定結構之化合物之本發明之著色感光性組合物(著色鹼顯影性感光性組合物)係耐熱性優異者。又,其硬化物係適合於顯示裝置用彩色濾光片者。 The colored photosensitive composition (colored alkali-developable photosensitive composition) of the present invention containing a compound having a specific structure is excellent in heat resistance. Further, the cured product is suitable for a color filter for a display device.
以下,針對本發明,基於較佳之實施形態進行說明。 Hereinafter, the present invention will be described based on preferred embodiments.
首先,對上述化合物進行說明,該化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有至少1個上述通式(1)所表示之結構者。 First, the above-mentioned compound is described as an organic dye having an absorption maximum value in a wavelength region from the ultraviolet to the near-infrared, and having at least one structure represented by the above formula (1) in the molecule.
作為上述於自紫外至近紅外之波長區域具有吸收極大值之有機色素,只要為於自紫外至近紅外之波長區域,即380~1200nm具有吸收極大值之化合物,則無特別限定,例如可列舉:氰基苯乙烯化合物、偶氮化合物、蒽醌化合物、靛藍類化合物、三芳基甲烷化合物、二苯并吡喃化合物、茜素化合物、吖啶化合物、茋化合物、噻唑化合物、萘酚化合物、喹啉化合物、硝基化合物、吲達胺化合物、化合物、酞菁化合物、花青化合物、二亞銨化合物、氰基乙烯基化合物、二氰基苯乙烯化合物、碳鎓化合物、玫瑰紅化合物、苝化合物、多烯萘內醯胺化合物、香豆素化合物、方酸鎓化合物、克酮鎓化合物、螺吡喃化合物、螺化合物、部花青化合物、氧喏化合物、苯乙烯基化合物、吡喃鎓化合物、繞丹寧化合物、唑啉酮化合物、鄰苯二甲醯亞胺化合物、萘二甲醯亞胺化合物、啉化合物、萘醌化合物、蒽醌化合物、氮雜蒽醌化合物、卟啉化合物、氮雜卟啉化合物、吡咯亞甲基化合物、喹吖啶酮化合物、二酮基吡咯并吡咯化合物、靛藍化合物、吖啶化合物、吖化合物、甲亞胺化合物、苯胺化合物、喹酞酮化合物、醌亞胺化合物、寡聚苯化合物、銥錯合物化合物、銪錯合物化合物等染料等,該等亦可混合複數種使用。 The organic dye having an absorption maximum value in the wavelength region from the ultraviolet to the near-infrared is not particularly limited as long as it has a maximum absorption value in the wavelength region from ultraviolet to near-infrared, that is, 380 to 1200 nm, and examples thereof include cyanide. Styrene compound, azo compound, hydrazine compound, indigo compound, triarylmethane compound, dibenzopyran compound, alizarin compound, acridine compound, hydrazine compound, thiazole compound, naphthol compound, quinoline compound , nitro compound, indamine compound, a compound, a phthalocyanine compound, a cyanine compound, a diimonium compound, a cyanovinyl compound, a dicyanostyrene compound, a carbonium compound, a rosin compound, an anthraquinone compound, a polyendeneamine compound, a coumarin Compound, bismuth succinate compound, ketone oxime compound, spiropyran compound, snail a compound, a merocyanine compound, an oxonium compound, a styryl compound, a pyrylium compound, a rhodanine compound, An oxazolinone compound, a phthalimide compound, a naphthyl imine compound, a porphyrin compound, a naphthoquinone compound, an anthraquinone compound, an azaindole compound, a porphyrin compound, an azaporphyrin compound, a pyrromethene compound, a quinacridone compound, a diketopyrrolopyrrole compound, an indigo compound, Acridine compound A dye such as a compound, a methylimine compound, an aniline compound, a quinophthalone compound, a quinone compound, an oligomeric benzene compound, a ruthenium complex compound, or a ruthenium complex compound may be used in combination of plural kinds.
作為將上述通式(1)所表示之結構導入上述於自紫外至近紅外之波長區域具有吸收極大值之有機色素的方法,並無特別限定,可列舉應用公知之反應之方法,例如可列舉:應用酯化、醯胺化等反應之方法。 The method of introducing the structure represented by the above formula (1) into the organic dye having an absorption maximum value in the wavelength region from the ultraviolet to the near-infrared is not particularly limited, and examples thereof include a method of applying a known reaction, and examples thereof include: A method of using a reaction such as esterification or amidation.
上述於自紫外至近紅外之波長區域具有吸收極大值之有機色素具有鍵結有1~10個上述通式(1)所表示之取代基之結構。取代基於複數個之情形時相互可相同亦可不同。關於取代基之數量,就合成之容易性之方面而言,較佳為2~6個。 The organic dye having an absorption maximum value in the wavelength region from the ultraviolet to the near-infrared has a structure in which 1 to 10 substituents represented by the above formula (1) are bonded. Instead of being based on a plurality of cases, they may be the same or different from each other. Regarding the number of substituents, it is preferably 2 to 6 in terms of easiness of synthesis.
作為上述通式(1)中之R01、R02、R03、R04及R05所表示之鹵素原子,可列舉:氟、氯、溴、碘。 Examples of the halogen atom represented by R 01 , R 02 , R 03 , R 04 and R 05 in the above formula (1) include fluorine, chlorine, bromine and iodine.
作為R01、R02、R03、R04及R05以及R1所表示之碳原子數1~40之烷基,可列舉:甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第三戊基、環戊基、己基、2-己基、3-己基、環己基、4-甲基環己基、庚基、2-庚基、3-庚基、異庚基、第三庚基、1-辛基、異辛基、第三辛基、壬基、異壬基、癸基、十一烷基、十二烷基、十三烷基、異十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、金剛烷基、1-金剛烷基、2-金剛烷基、2-甲基-1-金剛烷基、2-甲基-2-金剛烷基、2-乙基-1-金剛烷基、2-乙基-2-金剛烷基、2-降基、2-降基甲基等,作為R01、R02、R03、R04及R05以及R1所表示之碳原子數6~20之芳基,可列舉:苯基、萘基、蒽基、2-甲基苯基、3-甲基苯基、4-甲基苯基、4-乙烯基苯基、3-異丙基苯基、4-異丙基苯基、4-丁基苯基、4-異丁基苯基、4-第三丁基苯基、4-己基苯基、4-環己基苯基、4-辛基苯基、4-(2-乙基己基)苯基、4-硬脂基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4-二-第三丁基苯基、2,5-二-第三丁基苯基、2,6-二-第三丁基苯基、2,4-二-第三戊基苯基、2,5-二-第三戊基苯基、2,5-二-第三辛基苯基、2,4-二異丙苯基苯基、4-環己基苯基、(1,1'-聯苯)-4-基、2,4,5-三甲基苯基、二茂鐵基等,作為R01、R02、R03、R04及R05以及R1所表示之碳原子數7~20之 芳烷基,可列舉:苄基、茀基、茚基、9-茀基甲基、2-苯基丙烷-2-基、二苯甲基、三苯甲基、苯乙烯基、苯烯丙基等,作為R01、R02、R03、R04及R05以及R1所表示之碳原子數2~20之含雜環之基,可列舉:吡啶基、嘧啶基、嗒基、哌啶基、吡喃基、吡唑基、三嗪基、吡咯基、喹啉基、異喹啉基、咪唑基、苯并咪唑基、三唑基、呋喃基、呋喃基、苯并呋喃基、噻吩基、噻吩基、苯并噻吩基、噻二唑基、噻唑基、苯并噻唑基、唑基、苯并唑基、異噻唑基、異唑基、吲哚基、2-吡咯啶酮-1-基、2-哌啶酮-1-基、2,4-二氧基咪唑啶-3-基、2,4-二氧基唑啶-3-基等,作為R1所表示之三烷基矽烷基,可列舉:三甲基矽烷、三乙基矽烷、乙基二甲基矽烷等。 Examples of the alkyl group having 1 to 40 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include a methyl group, an ethyl group, a propyl group, an isopropyl group and a butyl group. Second butyl, tert-butyl, isobutyl, pentyl, isopentyl, third pentyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, Heptyl, 2-heptyl, 3-heptyl, isoheptyl, third heptyl, 1-octyl, isooctyl, trioctyl, decyl, isodecyl, decyl, undecyl , dodecyl, tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, adamantyl, 1-adamantane Base, 2-adamantyl, 2-methyl-1-adamantyl, 2-methyl-2-adamantyl, 2-ethyl-1-adamantyl, 2-ethyl-2-adamantane Base, 2-low Base, 2-low Examples of the aryl group having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 include a phenyl group, a naphthyl group, an anthracenyl group, and 2- Methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4 -isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, 4- Stearyl phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4- Dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-t-butylphenyl, 2,5-di-t-butylphenyl, 2,6-di-third Butylphenyl, 2,4-di-third amylphenyl, 2,5-di-third amylphenyl, 2,5-di-th-octylphenyl, 2,4-diiso Propylphenylphenyl, 4-cyclohexylphenyl, (1,1'-biphenyl)-4-yl, 2,4,5-trimethylphenyl, ferrocene, etc. as R 01 , R 02 , R 03 , R 04 and R 05 and R 1 represents an aralkyl group having 7 to 20 carbon atoms, and examples thereof include a benzyl group, a decyl group, a fluorenyl group, a 9-fluorenylmethyl group, and a 2-phenyl group. Propane-2- Base, diphenylmethyl, trityl, styryl, phenylallyl, etc., as R 01 , R 02 , R 03 , R 04 and R 05 and R 1 represents a carbon number of 2 to 20 Examples of the heterocyclic group include pyridyl, pyrimidinyl and anthracene. , piperidinyl, pyranyl, pyrazolyl, triazinyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furyl, benzo Furanyl, thienyl, thienyl, benzothienyl, thiadiazolyl, thiazolyl, benzothiazolyl, Azolyl, benzo Azolyl, isothiazolyl, iso Azyl, fluorenyl, 2-pyrrolidone-1-yl, 2-piperidin-1-yl, 2,4-dioxyimidazol-3-yl, 2,4-dioxy Examples of the trialkylsulfanyl group represented by R 1 include a trimethyldecane, a triethyldecane, and an ethyldimethylnet.
作為將R01、R02、R03、R04及R05以及R1所表示之烷基、芳基、芳烷基及含雜環之基進行取代之取代基,可列舉:乙烯基、烯丙基、丙烯酸基、甲基丙烯酸基等乙烯性不飽和基;氟、氯、溴、碘等鹵素原子;乙醯基、2-氯乙醯基、丙醯基、辛醯基、丙烯醯基、甲基丙烯醯基、苯基羰基(苯甲醯基)、鄰苯二甲醯基、4-三氟甲基苯甲醯基、三甲基乙醯基、鄰羥苯甲醯基、草醯基、硬脂醯基、甲氧基羰基、乙氧羰基、第三丁氧基羰基、正十八烷氧基羰基、胺甲醯基等醯基;乙醯氧基、苯甲醯氧基等醯氧基;胺基、乙基胺基、二甲胺基、二乙胺基、丁基胺基、環戊基胺基、2-乙基己基胺基、十二烷基胺基、苯胺基、氯苯基胺基、甲苯胺基、甲氧苯胺基、N-甲基-苯胺基、二苯基胺基、萘基胺基、2-吡啶基胺基、甲氧基羰基胺基、苯氧基羰基胺基、乙醯基胺基、苯甲醯基胺基、甲醯基胺基、三甲基乙醯基胺基、月桂醯基胺基、胺甲醯基胺基、N,N-二甲胺基羰基胺基、N,N-二乙胺基羰基胺基、嗎啉基羰基胺基、甲氧基羰基胺基、乙氧基羰基胺基、第三丁氧基羰基胺基、正十八烷氧基羰基胺基、N-甲基-甲氧基羰基 胺基、苯氧基羰基胺基、胺磺醯基胺基、N,N-二甲胺基磺醯胺基、甲基磺醯胺基、丁基磺醯胺基、苯基磺醯胺基等經取代胺基;磺醯胺基、磺醯基、羧基、氰基、磺基、羥基、硝基、巰基、醯亞胺基、胺甲醯基、磺醯胺基、膦酸基、磷酸基或羧基、磺基、膦酸基、磷酸基之鹽等。 Examples of the substituent in which R 01 , R 02 , R 03 , R 04 and R 05 and the alkyl group, the aryl group, the arylalkyl group and the hetero ring-containing group represented by R 1 are substituted include a vinyl group and an alkene group. An ethylenically unsaturated group such as a propyl group, an acryl group or a methacryl group; a halogen atom such as fluorine, chlorine, bromine or iodine; an ethyl group, a 2-chloroethyl group, a propyl group, a decyl group, an acryl group, or a group Alkyl fluorenyl, phenylcarbonyl (benzylidene), phthalic acid, 4-trifluoromethylbenzhydryl, trimethylethenyl, o-hydroxybenzhydryl, oxalyl a sulfhydryl group, a methoxycarbonyl group, an ethoxycarbonyl group, a tert-butoxycarbonyl group, an n-octadecyloxycarbonyl group, an amine carbaryl group or the like; an ethoxy group, a benzyl hydrazide group, etc. Oxyl; amine, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, Chlorophenylamino, toluidine, methoxyanilino, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino, methoxycarbonylamino, phenoxy Carbocarbonylamine, acetamidoamine, benzene Mercaptoamine, mercaptoamine, trimethylethenylamine, laurylamine, aminecarboxylamido, N,N-dimethylaminocarbonylamino, N,N-di Ethylaminocarbonylamino, morpholinylcarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-A a methoxycarbonylamino group, a phenoxycarbonylamino group, an amine sulfonylamino group, an N,N-dimethylaminosulfonylamino group, a methylsulfonylamino group, a butylsulfonylamino group, Substituted amine group such as phenylsulfonylamino; sulfonylamino, sulfonyl, carboxy, cyano, sulfo, hydroxy, nitro, decyl, quinone, amidyl, sulfonamide , a phosphonic acid group, a phosphate group or a carboxyl group, a sulfo group, a phosphonic acid group, a salt of a phosphate group, and the like.
又,R01、R02、R03、R04及R05以及R1所表示之烷基或芳烷基中之亞甲基可被取代為碳-碳雙鍵、-O-、-S-、-CO-、-O-CO-、-CO-O-、-O-CO-O-、-S-CO-、-CO-S-、-S-CO-O-、-O-CO-S-、-CO-NH-、-NH-CO-、-NH-CO-O-、-NR2-、>P=O、-S-S-或-SO2-,取代之位置及數量任意。 Further, the methylene group in the alkyl group or the aralkyl group represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 may be substituted with a carbon-carbon double bond, -O-, -S- , -CO-, -O-CO-, -CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO- S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR 2 -, >P=O, -SS- or -SO 2 -, the position and the number of substitutions are arbitrary.
作為R2所表示之碳原子數1~8之烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數1~40之烷基所例示者中滿足特定之碳原子數的基等。 Examples of the alkyl group having 1 to 8 carbon atoms represented by R 2 include an alkyl group having 1 to 40 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . A group or the like that satisfies a specific number of carbon atoms in the example.
上述通式(1)所表示之結構中,就耐熱性之方面而言,較佳為R02或R04之至少一者為碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳烷基或碳原子數2~20之含雜環之基者,R03為-O-R1者,尤其是R1為氫原子或碳原子數2~9之烷氧基羰基者,其中較佳為R1為氫原子或碳原子數2~9之烷氧基羰基,且R02或R04之至少一者為碳原子數1~40之烷基、碳原子數6~20之芳基、碳原子數7~20之芳烷基或碳原子數2~20之含雜環之基者,尤其是R1為氫原子或碳原子數2~9之烷氧基羰基,且R02或R04之至少一者為碳原子數1~10之烷基者。 In the structure represented by the above formula (1), in terms of heat resistance, it is preferred that at least one of R 02 or R 04 is an alkyl group having 1 to 40 carbon atoms and a carbon number of 6 to 20 An aryl group, an aralkyl group having 7 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, wherein R 03 is -OR 1 , especially R 1 is a hydrogen atom or a carbon number of 2 to 9 The alkoxycarbonyl group, wherein R 1 is preferably a hydrogen atom or an alkoxycarbonyl group having 2 to 9 carbon atoms, and at least one of R 02 or R 04 is an alkyl group having 1 to 40 carbon atoms. An aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms, especially R 1 being a hydrogen atom or a carbon number of 2 to 9. An alkoxycarbonyl group, and at least one of R 02 or R 04 is an alkyl group having 1 to 10 carbon atoms.
再者,作為碳原子數2~9之烷氧基羰基,可列舉:甲氧基羰基、乙氧基羰基、丙氧基羰基、異丙氧基羰基、丁氧基羰基、第二丁氧基羰基、第三丁氧基羰基、異丁氧基羰基、戊氧基羰基、異戊氧基羰基、第三戊氧基羰基、己氧基羰基、環己氧基羰基、環己基甲氧基 羰基、四氫呋喃氧基羰基、四氫吡喃氧基羰基等。 Further, examples of the alkoxycarbonyl group having 2 to 9 carbon atoms include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, and a second butoxy group. Carbonyl, tert-butoxycarbonyl, isobutoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, third pentyloxycarbonyl, hexyloxycarbonyl, cyclohexyloxycarbonyl, cyclohexylmethoxy A carbonyl group, a tetrahydrofuranyloxycarbonyl group, a tetrahydropyranyloxycarbonyl group or the like.
作為上述於自紫外至近紅外之波長區域具有吸收極大值之有機色素所例示者中,就合成之容易性及分子設計之方面而言,較佳為氰基苯乙烯化合物、三芳基甲烷化合物、花青化合物。 In the above-mentioned examples of the organic dye having an absorption maximum value in the wavelength region from the ultraviolet to the near-infrared, a cyanostyrene compound, a triarylmethane compound, and a flower are preferable in terms of easiness of synthesis and molecular design. Green compound.
上述氰基苯乙烯化合物中,就合成之容易性及分子設計之方面而言,較佳為下述通式(2)所表示者。 Among the above cyanostyrene compounds, those represented by the following formula (2) are preferred in terms of ease of synthesis and molecular design.
(式中,A表示苯環、萘環或蒽環,該等環可經上述通式(1)所表示之取代基、鹵素原子、氰基、羥基、硝基、碳原子數1~8之烷基、碳原子數1~8之烷氧基、碳原子數1~8之鹵化烷基或碳原子數1~8之鹵化烷氧基取代或者未經取代,R5表示氫原子、苯基、氰基、硝基、鹵素原子、碳原子數1~8之烷基、碳原子數1~8之烷氧基、碳原子數1~8之鹵化烷基或碳原子數1~8之鹵化烷氧基,Y表示氰基或-COOR8,R8表示氫原子、碳原子數1~8之烷基或上述通式(1)所表示之取代基,R8所表示之烷基中之亞甲基可被取代為-COO-、-O-、-OCO-、-NHCO-、-NH-或-CONH-,X為單鍵、氮原子、-NR9-、氧原子、硫原子、磷原子、-PR10-或 滿足下述<1>~<5>中之任一條件之有機基,且與Y由-COOR8表示時之R8、A、R6或R7中之任意一者以上鍵結, R6、R7、R9及R10分別獨立表示氫原子、碳原子數1~8之烷基、碳原子數6~20之芳基、碳原子數7~20之芳烷基或上述通式(1)所表示之取代基,R6、R7、R9及R10所表示之烷基、芳基及芳烷基可經上述通式(1)所表示之取代基、鹵素原子、羥基或硝基取代,R6、R7、R9及R10所表示之烷基及芳烷基中之亞甲基可被取代為-COO-、-O-、-OCO-、-NHCO-、-NH-或-CONH-,m為1~6之整數,分子內具有至少一個上述通式(1)所表示之取代基) (In the formula, A represents a benzene ring, a naphthalene ring or an anthracene ring, and the ring may be a substituent represented by the above formula (1), a halogen atom, a cyano group, a hydroxyl group, a nitro group, and a carbon number of 1 to 8; An alkyl group, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms or a halogenated alkoxy group having 1 to 8 carbon atoms substituted or unsubstituted, and R 5 represents a hydrogen atom or a phenyl group. a cyano group, a nitro group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogenated alkyl group having 1 to 8 carbon atoms or a halogenated group having 1 to 8 carbon atoms. Alkoxy, Y represents a cyano group or -COOR 8 , and R 8 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a substituent represented by the above formula (1), and an alkyl group represented by R 8 The methylene group may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-, X is a single bond, a nitrogen atom, -NR 9 -, an oxygen atom, a sulfur atom, a phosphorus atom, -PR 10 - or an organic group satisfying any of the following <1> to <5>, and any of R 8 , A, R 6 or R 7 when Y is represented by -COOR 8 one or more bond, R 6, R 7, R 9 and R 10 each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, the carbon atoms An aryl group of 6 to 20 carbon atoms, an aralkyl group having 7 to 20 or of the general formula (1) represented by the substituent group, R 6, R 7, represented by R 9 and R 10 the alkyl group, an aryl group, and The aralkyl group may be substituted by a substituent represented by the above formula (1), a halogen atom, a hydroxyl group or a nitro group, an alkyl group represented by R 6 , R 7 , R 9 and R 10 and a methylene group in an aralkyl group. The group may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-, m is an integer from 1 to 6, having at least one of the above formula (1) Substituent)
<1>m=2,且X由下述通式(3)表示。 <1> m=2, and X is represented by the following general formula (3).
(式中,X1表示-NR13-、二價之碳原子數1~35之脂肪族烴基、二價之碳原子數3~35之脂環式烴基、二價之碳原子數6~35之含芳香環烴基或二價之碳原子數2~35之雜環基或者由下述(3-1)~(3-3)中之任一者表示之取代基,X1所表示之脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-或組合該等而成之基,Z1及Z2分別獨立表示直接鍵、-O-、-S-、-SO2-、-SO-、-NR13-、-PR14-,R13及R14分別獨立表示氫原子、碳原子數1~8之烷基、碳原子數6~20之芳基或碳原子數7~20之芳烷基, R13及R14所表示之烷基、芳基及芳烷基可經鹵素原子、羥基或硝基取代,R13及R14所表示之烷基及芳烷基中之亞甲基可被取代為-COO-、-O-、-OCO-、-NHCO-、-NH-或-CONH-,其中,上述通式(3)所表示之基為碳原子數1~35之範圍內) (wherein, X 1 represents -NR 13 -, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, a divalent carbon atom group having 3 to 35 carbon atoms, and a divalent carbon atom number of 6 to 35 An aromatic ring-containing hydrocarbon group or a divalent heterocyclic group having 2 to 35 carbon atoms or a substituent represented by any one of the following (3-1) to (3-3), and a fat represented by X 1 The methylene group in the group of hydrocarbons may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -NH- or a combination thereof, and Z 1 and Z 2 are independently The direct bond, -O-, -S-, -SO 2 -, -SO-, -NR 13 -, -PR 14 -, R 13 and R 14 each independently represent a hydrogen atom and an alkyl group having 1 to 8 carbon atoms. An aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, and an alkyl group, an aryl group and an aralkyl group represented by R 13 and R 14 may be substituted by a halogen atom, a hydroxyl group or a nitro group. , the methylene group represented by R 13 and R 14 and the methylene group in the aralkyl group may be substituted with -COO-, -O-, -OCO-, -NHCO-, -NH- or -CONH-, wherein The group represented by the above formula (3) is in the range of 1 to 35 carbon atoms)
(式中,R21表示氫原子、可經碳原子數1~10之烷基或碳原子數1~10之烷氧基取代之苯基或碳原子數3~10之環烷基,R22表示碳原子數1~10之烷基、碳原子數1~10之烷氧基、碳原子數2~10之烯基或鹵素原子,R21及R22所表示之烷基、烷氧基及烯基可經鹵素原子取代或者未經取代,d為0~5之整數) (wherein R 21 represents a hydrogen atom, a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, R 22 And an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or a halogen atom, an alkyl group represented by R 21 and R 22 , an alkoxy group and Alkenyl group may be substituted or unsubstituted by a halogen atom, and d is an integer from 0 to 5)
[化6]
(式中,R23及R24分別獨立表示碳原子數1~10之烷基、碳原子數6~20之芳基、碳原子數6~20之芳氧基、碳原子數6~20之芳硫基、碳原子數8~20之芳基烯基、碳原子數7~20之芳烷基、碳原子數2~20之含雜環之基或鹵素原子,R23及R24所表示之烷基、芳基、芳氧基、芳硫基、芳基烯基、芳烷基及含雜環之基可經鹵素原子取代或者未經取代,R23及R24所表示之烷基及芳烷基中之亞甲基可被取代為不飽和鍵、-O-或-S-,R23可由鄰接之R23彼此形成環,e表示0~4之數,f表示0~8之數,g表示0~4之數,h表示0~4之數,g與h之數之合計為2~4) (wherein R 23 and R 24 each independently represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, and 6 to 20 carbon atoms; An arylthio group, an arylalkenyl group having 8 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms or a halogen atom, represented by R 23 and R 24 The alkyl group, the aryl group, the aryloxy group, the arylthio group, the arylalkenyl group, the aralkyl group and the heterocyclic group-containing group may be substituted or unsubstituted with a halogen atom, and the alkyl group represented by R 23 and R 24 may be the aralkyl group may be substituted with a methylene an unsaturated bond, -O- or -S-, R 23 may be adjacent to the R 23 form a ring, e represents a number of 0 to 4, f represents a number of 0 to 8 , g means 0~4, h means 0~4, the total of g and h is 2~4)
<2>m=3,且X由下述通式(4)表示。 <2> m=3, and X is represented by the following general formula (4).
(式中,X2表示取代有R25之碳原子、三價之碳原子數1~35之脂肪族烴基、三價之碳原子數3~35之脂環式烴基、三價之碳原子數6~35之含芳香環烴基或三價之碳原子數2~35之含雜環之基,R25表示氫原子、碳原子數1~8之烷基、碳原子數6~20之芳基或碳原子數7~20之芳烷基, X2所表示之脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-或組合該等而成之基,Z1~Z3分別獨立,與上述通式(3)中之Z1及Z2所表示之基相同,其中,上述通式(4)所表示之基為碳原子數1~35之範圍內) (wherein X 2 represents a carbon atom substituted with R 25 , an aliphatic hydrocarbon group having a trivalent carbon number of 1 to 35, an alicyclic hydrocarbon group having a trivalent carbon number of 3 to 35, and a trivalent carbon atom number 6 to 35, an aromatic cyclic hydrocarbon group or a trivalent carbon group having 2 to 35 carbon atoms, and R 25 represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an aryl group having 6 to 20 carbon atoms. Or an aralkyl group having 7 to 20 carbon atoms, and a methylene group in the aliphatic hydrocarbon group represented by X 2 may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, - NH- or a combination of these groups, Z 1 to Z 3 are each independently the same as those represented by Z 1 and Z 2 in the above formula (3), wherein the formula (4) The base is in the range of 1 to 35 carbon atoms)
<3>m=4,且X由下述通式(5)表示。 <3> m=4, and X is represented by the following general formula (5).
(式中,X3表示碳原子、四價之碳原子數1~35之脂肪族烴基、四價之碳原子數3~35之脂環式烴基、四價之碳原子數6~35之含芳香環烴基或四價之碳原子數2~35之含雜環之基,X3所表示之脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-或組合該等而成之基,Z1~Z4分別獨立,與上述通式(3)中之Z1及Z2所表示之基相同,其中,上述通式(5)所表示之基為碳原子數1~35之範圍內) (wherein X 3 represents a carbon atom, an aliphatic hydrocarbon group having a tetravalent carbon number of 1 to 35, an alicyclic hydrocarbon group having a tetravalent carbon number of 3 to 35, and a tetravalent carbon atom number of 6 to 35) An aromatic cyclic hydrocarbon group or a tetravalent heterocyclic group having 2 to 35 carbon atoms, and a methylene group in the aliphatic hydrocarbon group represented by X 3 may be substituted with -O-, -S-, -CO-, - COO-, -OCO-, -NH- or a combination thereof; Z 1 to Z 4 are each independently the same as those represented by Z 1 and Z 2 in the above formula (3), wherein The group represented by the formula (5) is in the range of 1 to 35 carbon atoms)
<4>m=5,且X由下述通式(6)表示。 <4> m=5, and X is represented by the following general formula (6).
(式中,X4表示五價之碳原子數2~35之脂肪族烴基、五價之碳原子數3~35之脂環式烴基、五價之碳原子數6~35之含芳香環烴基或五 價之碳原子數2~35之含雜環之基,X4所表示之脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-或組合該等而成之基,Z1~Z5分別獨立,與上述通式(3)中之Z1及Z2所表示之基相同,其中,上述通式(6)所表示之基為碳原子數2~35之範圍內) (wherein X 4 represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a pentavalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, and a pentavalent carbon group having 6 to 35 carbon atoms; Or a pentavalent heterocyclic group having 2 to 35 carbon atoms, and the methylene group in the aliphatic hydrocarbon group represented by X 4 may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -NH- or a combination of these groups, Z 1 to Z 5 are each independently the same as those represented by Z 1 and Z 2 in the above formula (3), wherein the above formula ( 6) The base expressed is in the range of 2 to 35 carbon atoms)
<5>m=6,且X由下述通式(7)表示。 <5> m=6, and X is represented by the following general formula (7).
(式中,X5表示六價之碳原子數2~35之脂肪族烴基、六價之碳原子數3~35之脂環式烴基、六價之碳原子數6~35之含芳香環烴基或六價之碳原子數2~35之含雜環之基,X5所表示之脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-或組合該等而成之基,Z1~Z6分別獨立,與上述通式(3)中之Z1及Z2所表示之基相同,其中,上述通式(7)所表示之基為碳原子數2~35之範圍內) (wherein, X 5 represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a hexavalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, and a hexavalent aromatic hydrocarbon group having 6 to 35 carbon atoms; Or a hexavalent heterocyclic group having 2 to 35 carbon atoms, and the methylene group in the aliphatic hydrocarbon group represented by X 5 may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -NH- or a combination of these groups, Z 1 to Z 6 are each independently the same as those represented by Z 1 and Z 2 in the above formula (3), wherein the above formula ( 7) The base expressed is in the range of 2 to 35 carbon atoms)
作為可取代上述通式(2)中之A所表示之苯環、萘環及蒽之鹵素原子、R5所表示之鹵素原子、以及可取代R6、R7、R9及R10所表示之烷基、芳基及芳烷基之鹵素原子,可列舉:作為R01、R02、R03、R04及R05所表示之鹵素原子所例示之基,作為可取代A所表示之苯環、萘環及蒽之碳原子數1~8之烷基、及R5~R10所表示之碳原子數1~8之烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數1~40之烷基所例示之基中滿 足特定之碳數的基等,作為可取代A所表示之苯環、萘環及蒽之碳原子數1~8之烷氧基及R5所表示之碳原子數1~8之烷氧基,可列舉:甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、第二丁氧基、第三丁氧基、異丁氧基、戊氧基、異戊氧基、第三戊氧基、己氧基、環己氧基、環己基甲氧基、四氫呋喃氧基、四氫吡喃氧基等,作為可取代A所表示之苯環、萘環及蒽之碳原子數1~8之鹵化烷基及R5所表示之碳原子數1~8之鹵化烷基,可列舉:上述碳原子數1~8之烷基之至少1個氫原子被取代為上述鹵素原子者,例如氯甲基、二氯甲基、三氯甲基、氟甲基、氟甲基、三氟甲基、九氟丁基等,作為可取代A所表示之苯環、萘環及蒽之碳原子數1~8之鹵化烷氧基及R5所表示之碳原子數1~8之鹵化烷氧基,可列舉:上述碳原子數1~8之烷氧基之至少1個氫原子被取代為上述鹵素原子者,例如氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、氟甲氧基、三氟甲氧基、九氟丁氧基等,作為R6、R7、R9及R10所表示之碳原子數6~20之芳基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數6~20之芳基所例示之基,作為R6、R7、R9及R10所表示之碳原子數7~20之芳烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數7~20之芳烷基所例示之基。 And a halogen atom represented by R 5 represented by A in the above formula (2), a naphthalene ring and an anthracene, a halogen atom represented by R 5 , and a substitutable R 6 , R 7 , R 9 and R 10 The halogen atom of the alkyl group, the aryl group and the aralkyl group may be exemplified as the halogen atom represented by R 01 , R 02 , R 03 , R 04 and R 05 , and may be substituted as the benzene represented by A. The alkyl group having 1 to 8 carbon atoms in the ring, naphthalene ring and anthracene, and the alkyl group having 1 to 8 carbon atoms represented by R 5 to R 10 may be exemplified as R 01 , R 02 , R 03 and R. R 05 and 04 carbon atoms, and the group represented by R 1 alkyl group of 1 to 40 of the illustrated meet specific group of carbon number, expressed as a substituent a of the benzene ring, a naphthalene ring and the carbon atom of the anthracene The alkoxy group having 1 to 8 and the alkoxy group having 1 to 8 carbon atoms represented by R 5 may, for example, be a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group or a butoxy group. Dibutoxy, tert-butoxy, isobutoxy, pentyloxy, isopentyloxy, third pentyloxy, hexyloxy, cyclohexyloxy, cyclohexylmethoxy, tetrahydrofuranyloxy, Tetrahydropyranyloxy, etc., as a substitutable A Benzene ring carbon atoms are shown, the number of carbon atoms of the naphthalene ring and an anthracene halogenated alkyl group and R 5 1 ~ 8 of the halogenated alkyl group represented by the 1-8, include: the above carbon atoms of alkyl group having 1 to 8 Where at least one hydrogen atom is substituted with the above halogen atom, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, fluoromethyl, trifluoromethyl, nonafluorobutyl, etc. The halogenated alkoxy group having 1 to 8 carbon atoms and the halogenated alkoxy group having 1 to 8 carbon atoms represented by R 5 in the benzene ring, the naphthalene ring and the fluorene represented by A, and the above-mentioned carbon atom number 1 At least one hydrogen atom of the alkoxy group of ~8 is substituted with the above halogen atom, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, fluoromethoxy, trifluoro Examples of the aryl group having 6 to 20 carbon atoms represented by R 6 , R 7 , R 9 and R 10 include a methoxy group, a nonafluorobutoxy group and the like, and examples thereof include R 01 , R 02 , R 03 and R. 04 and R 05 and R 1 represent a group represented by an aryl group having 6 to 20 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms represented by R 6 , R 7 , R 9 and R 10 . include: as R 01, R 02, R 03 , R 04 and R 05 And it illustrated the number of carbon atoms represented by R 1 of the aralkyl group having 7 to 20 of the group.
作為上述通式(3)中之X1所表示之二價之碳原子數1~35之脂肪族烴基,可列舉:甲烷、乙烷、丙烷、異丙烷、丁烷、第二丁烷、第三丁烷、異丁烷、己烷、2-甲基己烷、3-甲基己烷、庚烷、2-甲基庚烷、3-甲基庚烷、異庚烷、第三庚烷、1-甲基辛烷、異辛烷、第三辛烷、環丙烷、環丁烷、環戊烷、環己烷、環庚烷、2,4-二甲基環丁 烷、4-甲基環己烷等基經Z1及Z2取代之二價的基,脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-或組合該等而成之基,所謂組合該等而成之基,例如表示-COO-O-、-COO-S-、-O-OCO-、-S-OCO-、-CO-NH-、-NH-CO-等,其中,較佳為經-COO-、-O-、-OCO-、-NHCO-、-NH-、-CONH-、-O-CONH-或-NHCO-O-取代者,作為X1所表示之二價之碳原子數3~35之脂環式烴基,可列舉:環戊基、環己基、環庚基、環辛基、環癸基、1-金剛烷基、2-金剛烷基、降金剛烷基、2-甲基金剛烷基、降基、異降基、全氫萘基、全氫蒽基、二環[1.1.0]丁基、二環[1.1.1]戊基、二環[2.1.0]戊基、二環[3.1.0]己基、二環[2.1.1]己基、二環[2.2.0]己基、二環[4.1.0]庚基、二環[3.2.0]庚基、二環[3.1.1]庚基、二環[2.2.1]庚基、二環[5.1.0]辛基、二環[4.2.0]辛基、二環[4.1.1]辛基、二環[3.3.0]辛基、二環[3.2.1]辛基、二環[2.2.2]辛基、螺[4,4]壬基、螺[4,5]癸基、十氫萘、三環癸基、四環十二烷基、雪松醇基、環十二烷基等基經Z1及Z2取代之二價的基等,作為X1所表示之二價之碳原子數6~35之含芳香環烴基,可列舉:苯基、萘基、聯苯基等基經Z1及Z2取代之二價之基等,作為X1所表示之二價之碳原子數2~35之含雜環之基,可列舉:吡啶、吡、哌啶、哌、嘧啶、嗒、三、六氫三、呋喃、四氫呋喃、苯并二氫哌喃、二苯并吡喃、噻吩、硫雜環戊烷等基經Z1及Z2取代之二價之基。 Examples of the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by X 1 in the above formula (3) include methane, ethane, propane, isopropane, butane, and second butane. Tributane, isobutane, hexane, 2-methylhexane, 3-methylhexane, heptane, 2-methylheptane, 3-methylheptane, isoheptane, third heptane , 1-methyloctane, isooctane, third octane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, 2,4-dimethylcyclobutane, 4-methyl a divalent group in which a group such as cyclohexane is substituted with Z 1 and Z 2 , and a methylene group in the aliphatic hydrocarbon group may be substituted with -O-, -S-, -CO-, -COO-, -OCO- , -NH- or a combination of these, the so-called combination of these groups, for example, -COO-O-, -COO-S-, -O-OCO-, -S-OCO-, -CO -NH-, -NH-CO-, etc., wherein -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO- are preferred. The O-substituent, which is a divalent carbon atom having 3 to 35 carbon atoms represented by X 1 , may, for example, be a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group or a cyclodecyl group. Adamantyl, 2-adamantyl, norantantyl 2-methyladamantyl, descending Base , all-hydronaphthyl, perhydroindolyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[3.1.0]hexyl Bicyclo[2.1.1]hexyl, bicyclo[2.2.0]hexyl, bicyclo[4.1.0]heptyl, bicyclo[3.2.0]heptyl, bicyclo[3.1.1]heptyl, Ring [2.2.1] heptyl, bicyclo[5.1.0]octyl, bicyclo[4.2.0]octyl, bicyclo[4.1.1]octyl, bicyclo[3.3.0]octyl, Ring [3.2.1] octyl, bicyclo[2.2.2]octyl, spiro[4,4]decyl, spiro[4,5]decyl, decahydronaphthalene, tricyclodecyl, tetracyclic a divalent group substituted with Z 1 and Z 2 such as an alkyl group, a cedaryl group or a cyclododecyl group, and the divalent carbon group having 6 to 35 carbon atoms represented by X 1 may be used. a divalent group in which a group such as a phenyl group, a naphthyl group or a biphenyl group is substituted by Z 1 or Z 2 , and the like, and a divalent ring-containing group having 2 to 35 carbon atoms represented by X 1 may be used. List: pyridine, pyr Piperidine, piperazine Pyrimidine ,three Hexahydrogen a divalent group substituted with Z 1 and Z 2 such as furan, tetrahydrofuran, benzohydropyran, dibenzopyran, thiophene or thiolane.
該等基亦可進而經鹵素原子、氰基、硝基或碳原子數1~8之烷氧基取代。 These groups may be further substituted by a halogen atom, a cyano group, a nitro group or an alkoxy group having 1 to 8 carbon atoms.
作為R13及R14所表示之碳原子數1~8之烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數1~40之烷基所例 示之基中滿足特定之碳數的基,作為R13及R14所表示之碳原子數6~20之芳基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數6~20之芳基所例示之基,作為R13及R14所表示之碳原子數7~20之芳烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數7~20之芳烷基所例示之基,作為可取代R13及R14所表示之烷基、芳基及芳烷基之鹵素原子,可列舉:作為R01、R02、R03、R04及R05所表示之鹵素原子所例示之基。 Examples of the alkyl group having 1 to 8 carbon atoms represented by R 13 and R 14 include a carbon number of 1 to 40 represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . The group which satisfies a specific carbon number in the group exemplified for the alkyl group, and the aryl group having 6 to 20 carbon atoms represented by R 13 and R 14 may be exemplified as R 01 , R 02 , R 03 , R 04 and Examples of the aryl group having 6 to 20 carbon atoms represented by R 5 and R 1 and the aralkyl group having 7 to 20 carbon atoms represented by R 13 and R 14 may be exemplified as R 01 and R. 02 , R 03 , R 04 and R 05 and the group represented by R 1 represented by an aralkyl group having 7 to 20 carbon atoms, as an alkyl group, an aryl group and an aralkyl group which may be substituted for R 13 and R 14 The halogen atom of the group is exemplified as the halogen atom represented by R 01 , R 02 , R 03 , R 04 and R 05 .
於上述(3-1)所表示之取代基中,作為可取代R21所表示之苯基及碳原子數3~10之環烷基之碳原子數1~10之烷基以及R22所表示之碳原子數1~10之烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數1~40之烷基所例示之基中滿足特定之碳數的基等,作為可取代R21所表示之苯基及碳原子數3~10之環烷基之碳原子數1~10之烷氧基以及R22所表示之碳原子數1~10之烷氧基,可列舉:作為可取代A所表示之苯環、萘環及蒽之碳原子數1~8之烷氧基及R5所表示之碳原子數1~8之烷氧基所例示的基等,作為R21所表示之碳原子數3~10之環烷基,可列舉:環丙基、環丁基、環戊基、環庚基、環辛基等及該等基經上述碳原子數1~10之烷基或碳原子數1~10之烷氧基取代之基等,作為R22所表示之碳原子數2~10之烯基,可列舉:乙烯基、烯丙基、1-丙烯基、異丙烯基、2-丁烯基、1,3-丁二烯基、2-戊烯基、2-辛烯基等,作為R22所表示之鹵素原子、以及可取代R21及R22所表示之烷 基、烷氧基及烯基之鹵素原子,可列舉:作為R01、R02、R03、R04及R05所表示之鹵素原子所例示之基。 In the substituent represented by the above (3-1), the alkyl group having 1 to 10 carbon atoms and R 22 represented by a substituent of R 21 and a cycloalkyl group having 3 to 10 carbon atoms; The alkyl group having 1 to 10 carbon atoms is exemplified as the base exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . specific group of carbon number such as the number of carbon may be substituted and the phenyl group represented by R 21 carbon atoms, a cycloalkyl group of 3 to 10 atoms of the alkoxy group having 1 to 10 and represents a number of carbon atoms in R 22 Examples of the alkoxy group of ~10 include an alkoxy group having 1 to 8 carbon atoms and a alkoxy group having 1 to 8 carbon atoms represented by R 5 as a substitutable benzene ring, a naphthalene ring and an anthracene. Examples of the group and the like, and examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 21 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cycloheptyl group, a cyclooctyl group, and the like. The base substituted by the above-mentioned alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, and the alkenyl group having 2 to 10 carbon atoms represented by R 22 may, for example, be a vinyl group. Allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3- Dienyl, 2-pentenyl, 2-octenyl and the like, the halogen atom represented by R 22, and a substituted alkyl group represented by the R 21 and R 22, alkoxy and alkenyl group of a halogen atom, The group exemplified as the halogen atom represented by R 01 , R 02 , R 03 , R 04 and R 05 can be mentioned.
再者,可取代R22所表示之烷基、烷氧基及烯基之鹵素原子之取代位置並無限制。 Further, the substitution position of the halogen atom which may be substituted for the alkyl group, the alkoxy group and the alkenyl group represented by R 22 is not limited.
於上述(3-3)所表示之取代基中,作為R23及R24所表示之碳原子數1~10之烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數1~40之烷基所例示之基中滿足特定碳數的基等,作為R23及R24所表示之碳原子數6~20之芳基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數6~20之芳基所例示之基等,作為R23及R24所表示之碳原子數6~20之芳氧基,可列舉:苯氧基、萘氧基、2-甲基苯氧基、3-甲基苯氧基、4-甲基苯氧基、4-乙烯基苯基二氧基、3-異丙基苯氧基、4-異丙基苯氧基、4-丁基苯氧基、4-第三丁基苯氧基、4-己基苯氧基、4-環己基苯氧基、4-辛基苯氧基、4-(2-乙基己基)苯氧基、2,3-二甲基苯氧基、2,4-二甲基苯氧基、2,5-二甲基苯氧基、2,6-而甲基苯氧基、3,4-二甲基苯氧基、3,5-二甲基苯氧基、2,4-二-第三丁基苯氧基、2,5-二-第三丁基苯氧基、2,6-二-第三丁基苯氧基、2,4-二-第三戊基苯氧基、2,5-第三戊基苯氧基、4-環己基苯氧基、2,4,5-三甲基苯氧基、二茂鐵基氧基等基及該等基經鹵素原子取代之基等,作為R23及R24所表示之碳原子數6~20之芳硫基,可列舉:將可經上述鹵素原子取代之碳原子數6~20之芳氧基之氧原子取代為硫原子之基等,作為R23及R24所表示之碳原子數8~20之芳基烯基,可列舉:將可經上述鹵素原子取代之碳原子數6~20之芳氧基之氧原子取代為乙烯基、烯丙基、1-丙烯基、異丙烯基、2-丁烯基、1,3-丁二烯基、2- 戊烯基、2-辛烯基等烯基之基等,作為R23及R24所表示之碳原子數7~20之芳烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數7~20之芳烷基所例示之基等。 In the substituent represented by the above (3-3), examples of the alkyl group having 1 to 10 carbon atoms represented by R 23 and R 24 include R 01 , R 02 , R 03 , R 04 and R. 05 and the group represented by the alkyl group having 1 to 40 carbon atoms represented by R 1 , which are a group having a specific carbon number, and the aryl group having 6 to 20 carbon atoms represented by R 23 and R 24 may be mentioned. : a group exemplified as an aryl group having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 , and 6 as a carbon atom represented by R 23 and R 24 Examples of the aryloxy group of ~20 include a phenoxy group, a naphthyloxy group, a 2-methylphenoxy group, a 3-methylphenoxy group, a 4-methylphenoxy group, and a 4-vinylphenyldioxy group. , 3-isopropylphenoxy, 4-isopropylphenoxy, 4-butylphenoxy, 4-tert-butylphenoxy, 4-hexylphenoxy, 4-cyclohexylbenzene Oxyl, 4-octylphenoxy, 4-(2-ethylhexyl)phenoxy, 2,3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5- Dimethylphenoxy, 2,6-methylphenoxy, 3,4-dimethylphenoxy, 3,5-dimethylphenoxy, 2,4-di-t-butyl Phenoxy, 2,5-di-t-butylphenoxy Base, 2,6-di-t-butylphenoxy, 2,4-di-p-pentylphenoxy, 2,5-tripentylphenoxy, 4-cyclohexylphenoxy, a group such as 2,4,5-trimethylphenoxy or a ferrocenyloxy group, and a group substituted by a halogen atom, etc., as a group having 6 to 20 carbon atoms represented by R 23 and R 24 The thio group may be a group in which an oxygen atom of an aryloxy group having 6 to 20 carbon atoms which may be substituted by the above halogen atom is substituted with a sulfur atom, and the number of carbon atoms represented by R 23 and R 24 is 8 to 20 The arylalkenyl group may be an epoxy group substituted with an aryloxy group having 6 to 20 carbon atoms which may be substituted by the above halogen atom, and substituted with a vinyl group, an allyl group, a 1-propenyl group, an isopropenyl group, or a 2- An alkenyl group such as a butenyl group, a 1,3-butadienyl group, a 2-pentenyl group or a 2-octenyl group, or the like, and an aralkyl group having 7 to 20 carbon atoms represented by R 23 and R 24 Examples of the aralkyl group having 7 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 are exemplified.
作為R23及R24所表示之碳原子數2~20之含雜環之基,可列舉:吡啶、吡、哌啶、哌、嘧啶、嗒、三、六氫三、呋喃、四氫呋喃、苯并二氫吡喃、二苯并吡喃、噻吩、硫醇等基及該等基經鹵素原子取代之基等。 Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R 23 and R 24 include pyridine and pyrrol. Piperidine, piperazine Pyrimidine ,three Hexahydrogen a group such as furan, tetrahydrofuran, chroman, dibenzopyran, thiophene or thiol, and a group substituted by a halogen atom.
作為可取代R13及R14所表示之烷基、芳基、芳氧基、芳硫基、芳基烯基、芳烷基及含雜環之基之鹵素原子,可列舉:作為R01、R02、R03、R04及R05所表示之鹵素原子所例示之基。 Examples of the halogen atom which may be substituted for the alkyl group, the aryl group, the aryloxy group, the arylthio group, the arylalkenyl group, the aralkyl group and the hetero ring-containing group represented by R 13 and R 14 include R 01 . The group represented by the halogen atom represented by R 02 , R 03 , R 04 and R 05 .
作為上述通式(4)中之X2所表示之三價之碳原子數1~35之脂肪族烴基,可列舉:上述通式(3)中之X1之說明中所例示之脂肪族烴基經Z1、Z2及Z3取代之三價的基等,脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-NH-或組合該等而成之基,所謂組合該等而成之基,例如表示-COO-O-、-COO-S-、-O-OCO-、-S-OCO-、-CO-NH-、-NH-CO-等,其中,較佳為經-COO-、-O-、-OCO-、-NHCO-、-NH-、-CONH-、-O-CONH-或-NHCO-O-取代者,作為X2所表示之三價之碳原子數3~35之脂環式烴基,可列舉:上述通式(3)中之X1之說明中所例示之脂環式烴基經Z1、Z2及Z3取代之三價的基等,作為X2所表示之三價之碳原子數6~35之含芳香環烴基,可列舉:上述通式(3)中之X1之說明中所例示之含芳香環烴基經Z1、Z2及Z3取代之三價的基等,作為X2所表示之三價之碳原子數2~35之含雜環之基,可列舉:上述通式(3)中之X1之說明中所例示之含雜環之基經Z1、Z2及Z3取代之 三價的基等。 The aliphatic hydrocarbon group having a trivalent carbon number of 1 to 35 represented by X 2 in the above formula (4) may, for example, be an aliphatic hydrocarbon group exemplified in the description of X 1 in the above formula (3). The trimethyl group substituted by Z 1 , Z 2 and Z 3 , etc., the methylene group in the aliphatic hydrocarbon group may be substituted with -O-, -S-, -CO-, -CO-O-, -O- CO-, -SO 2 -, -NH- or a combination of these groups, the so-called combination of these groups, for example, -COO-O-, -COO-S-, -O-OCO-, - S-OCO-, -CO-NH-, -NH-CO-, etc., among which -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O are preferred. The -CONH- or -NHCO-O-substituent, as the trivalent carbon atom having 3 to 35 carbon atoms represented by X 2 , may be exemplified by the description of X 1 in the above formula (3). The trivalent group substituted with Z 1 , Z 2 and Z 3 in the alicyclic hydrocarbon group, and the trivalent carbon group having 6 to 35 carbon atoms represented by X 2 may be exemplified by the above formula. (3) The trivalent group of the aromatic ring-containing hydrocarbon group substituted by Z 1 , Z 2 and Z 3 as exemplified in the description of X 1 , and the trivalent carbon atom represented by X 2 is 2 to 35 a group containing a hetero ring, which can be enumerated And a trivalent group substituted with Z 1 , Z 2 and Z 3 as exemplified in the description of X 1 in the above formula (3).
又,作為R25所表示之碳原子數1~8之烷基、碳原子數6~20之芳基或碳原子數7~20之芳烷基,可列舉:與R13及R14所表示之碳原子數1~8之烷基、碳原子數6~20之芳基或碳原子數7~20之芳烷基相同之基等。 Further, the alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 20 carbon atoms or the aralkyl group having 7 to 20 carbon atoms represented by R 25 may be represented by R 13 and R 14 . The alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 20 carbon atoms or the same aralkyl group having 7 to 20 carbon atoms.
作為上述通式(5)中之X3所表示之四價之碳原子數1~35之脂肪族烴基,可列舉:上述通式(3)中之X1之說明中所例示之脂肪族烴基經Z1、Z2、Z3及Z4取代之四價之基等,脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-NH-或組合該等而成之基,所謂組合該等而成之基,例如表示-COO-O-、-COO-S-、-O-OCO-、-S-OCO-、-CO-NH-、-NH-CO-等,其中,較佳為經-COO-、-O-、-OCO-、-NHCO-、-NH-、-CONH-、-O-CONH-或-NHCO-O-取代者,作為X3所表示之四價之碳原子數3~35之脂環式烴基,可列舉:上述通式(3)中之X1之說明中所例示之脂環式烴基經Z1、Z2、Z3及Z4取代之三價之基等,作為X3所表示之四價之碳原子數6~35之含芳香環烴基,可列舉:上述通式(3)中之X1之說明中所例示之含芳香環烴基經Z1、Z2、Z3及Z4取代之四價之基等,作為X3所表示之四價之碳原子數2~35之含雜環之基,可列舉:上述通式(3)中之X1之說明中所例示之含雜環之基經Z1、Z2、Z3及Z4取代之四價之基等。 The aliphatic hydrocarbon group having a tetravalent carbon number of 1 to 35 represented by X 3 in the above formula (5) may, for example, be an aliphatic hydrocarbon group exemplified in the description of X 1 in the above formula (3). The tetramethyl group substituted by Z 1 , Z 2 , Z 3 and Z 4 , etc., the methylene group in the aliphatic hydrocarbon group may be substituted with -O-, -S-, -CO-, -COO-, -OCO -, -NH- or a combination of these, the so-called combination of these groups, for example, -COO-O-, -COO-S-, -O-OCO-, -S-OCO-, - CO-NH-, -NH-CO-, etc., among which are preferably -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO The -O-substituent, as the quaternary hydrocarbon group having a tetravalent carbon number of 3 to 35 represented by X 3 , an alicyclic hydrocarbon group exemplified in the description of X 1 in the above formula (3) The trivalent group substituted by Z 1 , Z 2 , Z 3 and Z 4 , and the tetravalent carbon atom-containing aromatic hydrocarbon group represented by X 3 may be exemplified by the above formula (3). The tetravalent group of the aromatic ring-containing hydrocarbon group substituted by Z 1 , Z 2 , Z 3 and Z 4 as exemplified in the description of X 1 , and the tetravalent carbon atom represented by X 3 is 2 to 35 a heterocyclic group, The tetravalent group in which the heterocyclic group-containing group exemplified in the description of X 1 in the above formula (3) is substituted with Z 1 , Z 2 , Z 3 and Z 4 may, for example, be mentioned.
作為上述通式(6)中之X4所表示之五價之碳原子數2~35之脂肪族烴基,可列舉:上述通式(3)中之X1之說明中所例示之脂肪族烴基經Z1、Z2、Z3、Z4及Z5取代之五價之基等,脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-CO-O-、-O-CO-、-SO2-、-NH-或組合該等而成之基,所謂組合該等而成之基,例如表示-COO-O-、-COO-S-、- O-OCO-、-S-OCO-、-CO-NH-、-NH-CO-等,其中,較佳為經-COO-、-O-、-OCO-、-NHCO-、-NH-、-CONH-、-O-CONH-或-NHCO-O-取代者,作為X4所表示之五價之碳原子數3~35之脂環式烴基,可列舉:上述通式(3)中之X1之說明中所例示之脂環式烴基經Z1、Z2、Z3、Z4及Z5取代之五價的基等,作為X4所表示之五價之碳原子數6~35之含芳香環烴基,可列舉:上述通式(3)中之X1之說明中所例示之含芳香環烴基經Z1、Z2、Z3、Z4及Z5取代之五價的基等,作為X4所表示之五價之碳原子數2~35之含雜環之基,可列舉:上述通式(12)中之X1之說明中所例示之含雜環之基經Z1、Z2、Z3、Z4及Z5取代之五價的基等。 The aliphatic hydrocarbon group having a pentavalent carbon number of 2 to 35 represented by X 4 in the above formula (6) may, for example, be an aliphatic hydrocarbon group exemplified in the description of X 1 in the above formula (3). The methylene group in the aliphatic hydrocarbon group may be substituted with -O-, -S-, -CO-, -CO- by a pentavalent group substituted by Z 1 , Z 2 , Z 3 , Z 4 and Z 5 . O-, -O-CO-, -SO 2 -, -NH- or a combination of these groups, the so-called combination of these groups, for example, -COO-O-, -COO-S-, - O-OCO-, -S-OCO-, -CO-NH-, -NH-CO-, etc., among which, preferably -COO-, -O-, -OCO-, -NHCO-, -NH-, -CONH-, -O-CONH- or -NHCO-O-, the alicyclic hydrocarbon group having 5 to 35 carbon atoms represented by X 4 may be exemplified by the above formula (3) a pentavalent group in which the alicyclic hydrocarbon group exemplified in X 1 is substituted by Z 1 , Z 2 , Z 3 , Z 4 and Z 5 , and the like, and the pentavalent carbon atom represented by X 4 is 6 to 35 Examples of the aromatic ring-containing hydrocarbon group include a pentavalent group in which the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the above formula (3) is substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 . Etc., as the five-valent carbon represented by X 4 The heterocyclic group having 2 to 35 atomic atoms, the heterocyclic group exemplified in the description of X 1 in the above formula (12), is Z 1 , Z 2 , Z 3 , Z 4 and Z. 5 substituted five-valent base and the like.
作為上述通式(7)中之X5所表示之六價之碳原子數2~35之脂肪族烴基,可列舉:上述通式(3)中之X1之說明中所例示之脂肪族烴基經Z1、Z2、Z3、Z4、Z5及Z6取代之六價的基等,脂肪族烴基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-或組合該等而成之基,所謂組合該等而成之基,例如表示-COO-O-、-COO-S-、-O-OCO-、-S-OCO-、-CO-NH-、-NH-CO-等,其中,較佳為經-COO-、-O-、-OCO-、-NHCO-、-NH-、-CONH-、-O-CONH-或-NHCO-O-取代者,作為X5所表示之六價之碳原子數3~35之脂環式烴基,可列舉:上述通式(3)中之X1之說明中所例示之脂環式烴基經Z1、Z2、Z3、Z4、Z5及Z6取代之五價的基等,作為X5所表示之六價之碳原子數6~35之含芳香環烴基,可列舉:上述通式(3)中之X1之說明中所例示之含芳香環烴基經Z1、Z2、Z3、Z4、Z5及Z6取代之六價的基等, 作為X5所表示之六價之碳原子數2~35之含雜環之基,可列舉:上述通式(3)中之X1之說明中所例示之含雜環之基經Z1、Z2、Z3、Z4、Z5及Z6取代之六價的基等。 The aliphatic hydrocarbon group having a hexavalent carbon number of 2 to 35 represented by X 5 in the above formula (7) may, for example, be an aliphatic hydrocarbon group exemplified in the description of X 1 in the above formula (3). a hexavalent group substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , etc., the methylene group in the aliphatic hydrocarbon group may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -SO 2 -, -NH- or a combination of these, the so-called combination of such groups, for example, -COO-O-, -COO-S-, -O -OCO-, -S-OCO-, -CO-NH-, -NH-CO-, etc., among which -COO-, -O-, -OCO-, -NHCO-, -NH-, - The alicyclic hydrocarbon group having a hexavalent carbon number of 3 to 35 represented by X 5 as a substitution of CONH-, -O-CONH- or -NHCO-O-, may be exemplified by X in the above formula (3) The pentavalent group in which the alicyclic hydrocarbon group exemplified in the description of 1 is substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 , etc., as the hexavalent carbon atom represented by X 5 The aromatic ring-containing hydrocarbon group of ~35, wherein the aromatic ring-containing hydrocarbon group exemplified in the description of X 1 in the above formula (3) is substituted by Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 the hexavalent group, as X 5 Suo Hexavalent of carbon atoms of 2 to 35 illustrate the of the heterocyclic group include: the above general formula (3) in the description of X 1 as exemplified by the heterocyclic group of Z 1, Z 2, Z 3 , Z 4 , Z 5 and Z 6 substituted hexavalent groups and the like.
上述通式(2)所表示之化合物中,A為苯環者;R5為氫原子者;R6、R7或R8具有上述通式(1)所表示之取代基者;m為2時,X由上述通式(3)表示,式(3)中之X1為選自下述群1之基者;m為3時,X由上述通式(4)表示,式(4)中之X2為選自下述群2之基者;m為4時,X由上述通式(5)表示,式(5)中之X3為選自群3之基者;m為5時,X由上述通式(6)表示,式(6)中之X4為選自下述群4之基者;m為6時,X由上述通式(7)表示,式(7)中之X5為選自下述群5之基者因原料之獲取或製造容易,且耐熱性較高,故而較佳。 In the compound represented by the above formula (2), A is a benzene ring; R 5 is a hydrogen atom; and R 6 , R 7 or R 8 has a substituent represented by the above formula (1); m is 2 When X is represented by the above formula (3), X 1 in the formula (3) is a group selected from the group 1 below; when m is 3, X is represented by the above formula (4), and the formula (4) X 2 is a group selected from the group 2 below; when m is 4, X is represented by the above formula (5), and X 3 in the formula (5) is selected from the group of the group 3; m is 5 When X is represented by the above formula (6), X 4 in the formula (6) is a group selected from the group 4 below; when m is 6, X is represented by the above formula (7), and the formula (7) Among them, X 5 is a group selected from the group 5 below, and is preferable because it is easy to obtain or manufacture a raw material and has high heat resistance.
[化11]
(式中,R5為與上述通式(1)中之R5相同之基,於基中為兩個以上之情形時,可相同亦可不同,p表示1~3之整數,q表示0~3之整數,r表示0~19之整數)。 (wherein R 5 is the same group as R 5 in the above formula (1), and when it is two or more in the group, it may be the same or different, p represents an integer of 1 to 3, and q represents 0. An integer of ~3, r represents an integer from 0 to 19).
[化12]
[化15]
作為上述通式(1)所表示之化合物之具體例,可列舉:下述[化16]~[化18]所表示之化合物,但本發明並不受該等化合物限制。 Specific examples of the compound represented by the above formula (1) include the compounds represented by the following [Chemistries 16] to [Chem. 18], but the present invention is not limited by these compounds.
[化17]
[化18B]
上述三芳基甲烷化合物中,就合成之容易性及分子設計之方面而言,較佳為下述通式(8)所表示者。 Among the above triarylmethane compounds, those represented by the following formula (8) are preferred in terms of ease of synthesis and molecular design.
[化19]
(式中,R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41及R42分別獨立表示氫原子、鹵素原子、氰基、硝基、羥基、碳原子數1~8之烷基、碳原子數6~12之芳基、碳原子數7~20之芳烷基或-X11-Y11,X11表示氧原子或硫原子,Y11表示碳原子數1~8之烷基、碳原子數6~12之芳基、碳原子數7~20之芳烷基,R31~R42及Y11所表示之烷基、芳基或芳烷基可經鹵素原子取代或者未經取代,R32與R43、R33與R44、R36與R45、R37與R46、R40與R47、R41與R48、R31與R32、R33與R34、R35與R36、R37與R38、R39與R40及R41與R42可連結而形成6員環,R31與R42、R34與R35及R38與R39可經由單鍵、氧原子、硫原子、硒原子、CR49R50、CO、NR51、PR52或SO2連結而形成環,R43、R44、R45、R46、R47及R48分別獨立表示碳原子數1~8之烷基、苯基或苄基,R43~R48所表示之烷基可經羥基、鹵素原子、氰基或硝基取代或者未經取代,R43~R48所表示之苯基及苄基可經碳原子數1~4之烷基、鹵素原 子、氰基或乙烯基取代或者未經取代,R43與R44、R45與R46、及R47與R48可連結而形成3~6員環,Anq-表示q價之陰離子,q表示1或2,p表示將電荷保持為中性之係數,於分子內具有至少1個上述通式(1)所表示之取代基)。 (wherein R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 and R 42 each independently represent a hydrogen atom, a halogen atom, or a cyano group. a nitro group, a hydroxyl group, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 20 carbon atoms or -X 11 -Y 11 , and X 11 represents an oxygen atom or Sulfur atom, Y 11 represents an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and an alkyl group represented by R 31 to R 42 and Y 11 , aryl or aralkyl may be substituted or unsubstituted with a halogen atom, R 32 and R 43 , R 33 and R 44 , R 36 and R 45 , R 37 and R 46 , R 40 and R 47 , R 41 and R 48 , R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R 38 , R 39 and R 40 and R 41 and R 42 may be bonded to form a 6-membered ring, R 31 and R 42 , R 34 and R 35 and R 38 and R 39 may be bonded via a single bond, an oxygen atom, a sulfur atom, a selenium atom, CR 49 R 50 , CO, NR 51 , PR 52 or SO 2 to form a ring, R 43 , R 44 , R 45 , R 46 , R 47 and R 48 each independently represent an alkyl group having 1 to 8 carbon atoms, a phenyl group or a benzyl group, and an alkyl group represented by R 43 to R 48 may be used. Substituted or unsubstituted by a hydroxyl group, a halogen atom, a cyano group or a nitro group, the phenyl group and the benzyl group represented by R 43 to R 48 may be an alkyl group having 1 to 4 carbon atoms, a halogen atom, a cyano group or a vinyl group. Substituted or unsubstituted, R 43 and R 44 , R 45 and R 46 , and R 47 and R 48 may be bonded to form a 3 to 6 membered ring, An q- represents a q-valent anion, and q represents 1 or 2, p. The coefficient indicating that the charge is kept neutral is at least one substituent represented by the above formula (1) in the molecule.
於上述通式(8)中,作為R31~R42所表示之鹵素原子、可取代R31~R42及Y11所表示之烷基、芳基或芳烷基之鹵素原子、可取代R43~R48所表示之烷基、苯基及苄基之鹵素原子,可列舉:作為R01、R02、R03、R04及R05所表示之鹵素原子所例示之基。 In the above general formula (8), examples of the halogen atom represented by the R 31 ~ R 42, R 31 ~ may be a substituted alkyl group represented by the R 42, and Y 11, an aryl group or aralkyl group of a halogen atom, may be substituted with R Examples of the halogen atom of the alkyl group, the phenyl group and the benzyl group represented by 43 to R 48 include the groups exemplified as the halogen atom represented by R 01 , R 02 , R 03 , R 04 and R 05 .
作為R31~R48及Y11所表示之碳原子數1~8之烷基以及可取代R43~R48所表示之苯基及苄基之碳原子數1~4之烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數1~40之烷基所例示之基中滿足特定之碳數的基等,作為R31~R42及Y11所表示之碳原子數6~12之芳基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數6~20之芳基所例示之基中滿足特定之碳數的基等,作為R31~R42及Y11所表示之碳原子數7~20之芳烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數7~20之芳烷基所例示之基等,作為R32與R43、R33與R44、R36與R45、R37與R46、R40與R47、R41與R48、R31與R32、R33與R34、R35與R36、R37與R38、R39與R40及R41與R42連結而可形成之6員環,可列舉:哌啶環、吡啶環、嘧啶環、喹啉環、異喹啉環、咯啶環等,作為R31與R42、R34與R35及R38與R39經由單鍵、氧原子、硫原子、硒原子、CR49R50、CO、NR51、PR52或SO2連結而可形成之環,可列舉:二氫蒽環、吖啶環、二苯并吡喃環、硫環等, 作為R43與R44、R45與R46、及R47與R48連結而可形成之3~6員環之雜環,可列舉:哌啶環、哌環、吡咯啶環、嗎啉環、硫代嗎啉環、吡啶環、吡環、嘧啶環、喹啉環、異喹啉環、咪唑環、唑環、咪唑啶環、吡唑啶環、異唑啶環、異四氫噻唑環等,該等環可與其他環縮合,或者被取代。 The alkyl group having 1 to 8 carbon atoms represented by R 31 to R 48 and Y 11 and the alkyl group having 1 to 4 carbon atoms which may be substituted by a phenyl group and a benzyl group represented by R 43 to R 48 may be mentioned. : as a group exemplified by R 01 , R 02 , R 03 , R 04 and R 05 and an alkyl group having 1 to 40 carbon atoms represented by R 1 , which satisfies a specific carbon number, etc., as R 31 to R The aryl group having 6 to 12 carbon atoms represented by 42 and Y 11 may, for example, be an aryl group having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . In the exemplified group, the arylalkyl group having 7 to 20 carbon atoms represented by R 31 to R 42 and Y 11 is exemplified as R 01 , R 02 , R 03 , and the like. R 04 and R 05 and R 1 represent a group represented by an aralkyl group having 7 to 20 carbon atoms, and as R 32 and R 43 , R 33 and R 44 , R 36 and R 45 , R 37 and R 46 , R 40 and R 47 , R 41 and R 48 , R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R 38 , R 39 and R 40 and R 41 and R 42 are bonded. The 6-membered ring which can be formed includes a piperidine ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a pyridyl ring or the like as R 31 and R 42 , R 34 and R 35 and R 38 and R 39 via a single bond, an oxygen atom, a sulfur atom, a selenium atom, CR 49 R 50 , CO, NR 51 , PR 52 or SO 2 Rings which can be formed by linking include dihydroindole ring, acridine ring, dibenzopyran ring, sulfur A heterocyclic ring of 3 to 6 membered rings which may be formed by linking R 43 and R 44 , R 45 and R 46 , and R 47 and R 48 may, for example, be a piperidine ring or a piperidine. Ring, pyrrolidine ring, morpholine ring, thiomorpholine ring, pyridine ring, pyridyl Ring, pyrimidine ring, quinoline ring, isoquinoline ring, imidazole ring, Oxazole ring, imidazolidinium ring, pyrazolidine ring, different Azortidine ring, isotetrahydrothiazole ring, etc., which may be condensed with other rings or substituted.
上述通式(8)中,作為Anq-所表示之陰離子,例如,作為一價者,可列舉:氯化物離子、溴化物離子、碘化物離子、氟化物離子等鹵化物離子;過氯酸根離子、氯酸根離子、硫氰酸根離子、六氟磷酸根離子、六氟銻酸根離子、四氟硼酸根離子等無機系陰離子;甲磺酸根離子、十二烷基磺酸根離子、苯磺酸根離子、甲苯磺酸根離子、三氟甲磺酸根離子、萘磺酸根離子、二苯胺-4-磺酸根離子、2-胺基-4-甲基-5-氯苯磺酸根離子、2-胺基-5-硝基苯磺酸根離子、酞菁磺酸根離子、具有聚合性取代基之磺酸根離子、日本專利特開平10-235999、日本專利特開平10-337959、日本專利特開平11-102088、日本專利特開2000-108510、日本專利特開2000-168223、日本專利特開2001-209969、日本專利特開2001-322354、日本專利特開2006-248180、日本專利特開2006-297907、日本專利特開平8-253705號公報、特表2004-503379號公報、日本專利特開2005-336150號公報、國際公開2006/28006號公報等所記載之磺酸根離子等有機磺酸系陰離子;辛基磷酸根離子、十二烷基磷酸根離子、十八烷基磷酸根離子、苯基磷酸根離子、壬基苯基磷酸根離子、2,2'-亞甲基雙(4,6-二-第三丁基苯基)磺酸根離子等有機磷酸系陰離子、雙三氟甲磺醯基醯亞胺離子、雙全氟丁磺醯基醯亞胺離子、全氟4-乙基環己烷磺酸根離子、四(五氟苯基)硼酸根離子、三(氟烷基磺醯基)羧酸根陰離子等,作為二價者,例如可列舉;苯二磺酸根離子、萘二磺酸根離子等。又,亦可視需要而使用具有使處於激發狀態之活性分子脫激發(淬滅)之功能 之淬滅陰離子或於環戊二烯基環具有羧基或膦酸基、磺酸基等陰離子性基之二茂鐵、二茂釕等茂金屬化合物陰離子等。又,p係以於分子整體中電荷成為中性之方式進行選擇。 In the above formula (8), examples of the anion represented by An q- include, for example, a halide ion such as a chloride ion, a bromide ion, an iodide ion or a fluoride ion; and a perchlorate; Inorganic anions such as ions, chlorate ions, thiocyanate ions, hexafluorophosphate ions, hexafluoroantimonate ions, tetrafluoroborate ions; mesylate ions, dodecylsulfonate ions, benzenesulfonate ions , tosylate ion, triflate ion, naphthalene sulfonate ion, diphenylamine-4-sulfonate ion, 2-amino-4-methyl-5-chlorobenzenesulfonate ion, 2-amino group- 5-nitrobenzenesulfonate ion, phthalocyanine sulfonate ion, sulfonate ion having a polymerizable substituent, Japanese Patent Laid-Open No. Hei 10-235999, Japanese Patent Laid-Open No. Hei 10-337959, Japanese Patent Laid-Open No. 11-102088, Japan Patent Laid-Open No. 2000-108510, Japanese Patent Laid-Open No. 2000-168223, Japanese Patent Laid-Open No. 2001-209969, Japanese Patent Laid-Open No. 2001-322354, Japanese Patent Laid-Open No. Hei No. 2006-248180, Japanese Patent Laid-Open No. 2006-297907, Japanese Patent No. Kaiping No. 8-253705, special An organic sulfonic acid anion such as a sulfonate ion described in, for example, Japanese Patent Publication No. 2005-336150, and International Publication No. 2006/28006; octyl phosphate ion, dodecyl phosphate ion , octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis(4,6-di-t-butylphenyl)sulfonate ion, etc. Organic phosphate anion, bistrifluoromethanesulfonyl ruthenium ion, bisperfluorobutylsulfonyl quinone imine ion, perfluoro 4-ethylcyclohexane sulfonate ion, tetrakis(pentafluorophenyl)borate Examples of the divalent ones include an ion, a tris(fluoroalkylsulfonyl)carboxylate anion, and the like; and a benzenedisulfonate ion or a naphthalene disulfonate ion. Further, a quenching anion having a function of de-exciting (quenching) an active molecule in an excited state or an anionic group having a carboxyl group or a phosphonic acid group or a sulfonic acid group in the cyclopentadienyl ring may be used as needed. Metallocene compound anions such as ferrocene and ferrocene. Further, p is selected such that the charge in the entire molecule becomes neutral.
上述通式(8)中,Anq-所表示之陰離子亦可具有1~10個上述通式(1)所表示之取代基,作為此種陰離子,例如可列舉:下述[化19A]所表示之陰離子,但本發明並不受該等陰離子限制。 In the above formula (8), the anion represented by An q- may have 1 to 10 substituents represented by the above formula (1), and examples of such an anion include the following [Chemistry 19A]. Anions are indicated, but the invention is not limited by such anions.
作為上述之淬滅陰離子,例如可列舉:如日本專利特開昭60-234892號公報、日本專利特開平5-43814號公報、日本專利特開平5-305770號公報、日本專利特開平6-239028號公報、日本專利特開平9-309886號公報、日本專利特開平9-323478號公報、日本專利特開平10-45767號公報、日本專利特開平11-208118號公報、日本專利特開2000-168237號公報、日本專利特開2002-201373號公報、日本專利特開2002-206061號公報、日本專利特開2005-297407號公報、日本專利特公平7-96334號公報、國際公開98/29257號公報等所記載之陰離子。 The above-mentioned quenching anion is exemplified by, for example, Japanese Laid-Open Patent Publication No. SHO-60-234892, Japanese Patent Laid-Open No. Hei 5-43814, Japanese Patent Laid-Open No. Hei 5-305770, and Japanese Patent Laid-Open No. Hei 6-239028 Japanese Laid-Open Patent Publication No. Hei 9-309886, Japanese Patent Laid-Open No. Hei 9-323478, Japanese Patent Laid-Open No. Hei 10-45767, Japanese Patent Laid-Open No. Hei 11-208118, and Japanese Patent Laid-Open No. 2000-168237 Japanese Laid-Open Patent Publication No. 2002-201373, Japanese Patent Laid-Open Publication No. 2002-206061, Japanese Patent Laid-Open No. Hei No. Hei No. Hei. No. Hei. No. Hei. No. Hei. The anions described herein.
作為上述通式(I)中之Anq-所表示之陰離子,就耐熱性之方面而言,較佳為一價之有機磺酸系陰離子、雙三氟甲磺醯基醯亞胺離子、雙全氟丁磺醯基醯亞胺離子、全氟4-乙基環己烷磺酸根離子、苯二磺酸根離子、萘二磺酸根離子,進而較佳為雙三氟甲磺醯基醯亞胺離子。 The anion represented by An q- in the above formula (I) is preferably a monovalent organic sulfonic acid anion, bistrifluoromethanesulfonyl quinone imine ion, or both in terms of heat resistance. Fluorine sulfonyl quinone imine ion, perfluoro 4-ethylcyclohexane sulfonate ion, benzenedisulfonate ion, naphthalene disulfonate ion, and further preferably bistrifluoromethanesulfonyl quinone imide ion .
作為上述通式(8)所表示之化合物之具體例,可列舉:下述[化20A]及[化20B]所表示之化合物,但本發明並不受該等化合物限制。 Specific examples of the compound represented by the above formula (8) include the compounds represented by the following [Chemical Formula 20A] and [Chemical 20B], but the present invention is not limited by these compounds.
上述花青化合物中,就合成之容易性及分子設計之方面而言,較佳為下述通式(9)~(12)中之任一者所表示者。 Among the above cyanine compounds, those which are represented by any one of the following general formulae (9) to (12) are preferable in terms of easiness of synthesis and molecular design.
[化21]
(式中,D表示選自下述之群I之(a)~(m)之基,D'表示選自下述之群II之(a')~(m')之基,Q表示構成碳原子數1~9之次甲基鏈,且亦可於鏈中含有環結構之連結基,該次甲基鏈中之氫原子可經羥基、鹵素原子、氰基、-NR51R52、碳原子數6~12之芳基、碳原子數7~12之芳烷基或碳原子數1~8之烷基取代,該-NR51R52、芳基、芳烷基及烷基可進而經羥基、鹵素原子、氰基或-NR51R52取代,-NR51R52、芳基、芳烷基及烷基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-,R51及R52表示碳原子數6~12之芳基、碳原子數7~12之芳烷基或碳原子數1~8之烷基,Anq-表示q價之陰離子,q表示1或2,p表示保持電荷為中性之係數,於分子內具有至少一個上述通式(1)所表示之取代基)。 (wherein D represents a group selected from the group (a) to (m) of the group I below, and D' represents a group selected from the group (a') to (m') of the following group II, and Q represents a constitution. a methine chain having 1 to 9 carbon atoms, and may also have a linking group having a ring structure in the chain, and the hydrogen atom in the methine chain may pass through a hydroxyl group, a halogen atom, a cyano group, -NR 51 R 52 , An aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms or an alkyl group having 1 to 8 carbon atoms, and the -NR 51 R 52 , an aryl group, an aralkyl group and an alkyl group may be further Substituted by a hydroxyl group, a halogen atom, a cyano group or -NR 51 R 52 , a methylene group in -NR 51 R 52 , an aryl group, an aralkyl group and an alkyl group may be substituted with -O-, -S-, -CO -, -COO-, -OCO-, -SO 2 -, -NH-, -CONH-, -NHCO-, -N=CH- or -CH=CH-, R 51 and R 52 represent a carbon number of 6~ An aryl group of 12, an aralkyl group having 7 to 12 carbon atoms or an alkyl group having 1 to 8 carbon atoms, An q- represents an anion of q valence, q represents 1 or 2, and p represents a coefficient which maintains a neutral charge. And having at least one substituent represented by the above formula (1) in the molecule).
(式中,D表示選自下述之群I之(a)~(m)之基,D'表示選自下述之群II之(a')~(m')之基)。 (wherein D represents a group selected from the group (a) to (m) of the group I below, and D' represents a group selected from the group (a') to (m') of the following group II).
[化23]
(式中,環G及環G'表示苯環、萘環、菲環或吡啶環,R53及R53'表示羥基、鹵素原子、硝基、氰基、-SO3H、羧基、胺基、醯胺基、二茂鐵基、碳原子數6~30之芳基、碳原子數7~30之芳烷基或碳原子數1~8之烷基,R53及R53'所表示之芳基、芳烷基及烷基可經羥基、鹵素原子、硝基、氰基、-SO3H、羧基、胺基、醯胺基或二茂鐵基取代, R53及R53'所表示之芳基、芳烷基及烷基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-,R54~R61及R54'~R61'表示與R53及R53'相同之基或氫原子,X12、X12'、X13及X13'表示氧原子、硫原子、硒原子、-CR62R63-、碳原子數3~6之環烷-1,1-二基、-NH-或-NY13-,R62及R63表示與R53及R53'相同之基或氫原子,Y12、Y12'及Y13表示碳原子數1~20之烷基、碳原子數6~30之芳基或碳原子數7~30之芳烷基,Y12、Y12'及Y13所表示之烷基、芳基及芳烷基可經羥基、鹵素原子、氰基、羧基、胺基、醯胺基、二茂鐵基、-SO3H或硝基取代或者未經取代,Y12、Y12'及Y13所表示之烷基、芳基及芳烷基中之亞甲基可被取代為-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-,r及r'表示0或於(a)~(e)、(g)~(j)、(l)、(m)、(a')~(e')、(g')~(j')、(l')及(m')中可取代之數)。 (wherein ring G and ring G' represent a benzene ring, a naphthalene ring, a phenanthrene ring or a pyridine ring, and R 53 and R 53' represent a hydroxyl group, a halogen atom, a nitro group, a cyano group, -SO 3 H, a carboxyl group, an amine group. , amidino group, ferrocenyl group, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or an alkyl group having 1 to 8 carbon atoms, represented by R 53 and R 53 ' The aryl, aralkyl and alkyl groups may be substituted by a hydroxyl group, a halogen atom, a nitro group, a cyano group, a -SO 3 H group, a carboxyl group, an amine group, a decylamino group or a ferrocenyl group, represented by R 53 and R 53 ' The methylene group in the aryl group, the aralkyl group and the alkyl group may be substituted into -O-, -S-, -CO-, -COO-, -OCO-, -SO 2 -, -NH-, -CONH -, -NHCO-, -N=CH- or -CH=CH-, R 54 to R 61 and R 54' to R 61 ' represent the same or hydrogen atom as R 53 and R 53 ' , X 12 , X 12' , X 13 and X 13' represent an oxygen atom, a sulfur atom, a selenium atom, -CR 62 R 63 -, a cycloalkane-1,1-diyl group having a carbon number of 3 to 6, -NH- or -NY 13 -, R 62 and R 63 represent the same group or a hydrogen atom as R 53 and R 53 ' , and Y 12 , Y 12' and Y 13 represent an alkyl group having 1 to 20 carbon atoms and a carbon number of 6 to 30 aryl groups. Alkyl group having 7 to 30 carbon atoms, Y 12 , Y 12' And the alkyl, aryl and aralkyl groups represented by Y 13 may be substituted by a hydroxyl group, a halogen atom, a cyano group, a carboxyl group, an amine group, a decyl group, a ferrocenyl group, a -SO 3 H or a nitro group or Substituted, the methylene groups in the alkyl, aryl and aralkyl groups represented by Y 12 , Y 12 ' and Y 13 may be substituted with -O-, -S-, -CO-, -COO-, -OCO -, -SO 2 -, -NH-, -CONH-, -NHCO-, -N=CH- or -CH=CH-, r and r' represent 0 or (a)~(e), (g) ~(j), (l), (m), (a')~(e'), (g')~(j'), (l'), and (m') can be replaced.
上述通式(9)中,關於Q,作為構成碳原子數1~9之次甲基鏈,且亦可於鏈中含有環結構之連結基,下述(Q-1)~(Q-11)中之任一者所表示之基因製造容易故而較佳。對於碳原子數1~9之次甲基鏈中之碳原子數而言,不包括表示次甲基鏈及亦可於鏈中含有環結構之連結基,且進而取代該連結基之基(例如下述R62~R67、Z')的碳原子(例如,連結基(Q-1)中之兩末端之碳原子)。 In the above formula (9), Q is a methine chain constituting a carbon number of 1 to 9, and may have a linking group having a ring structure in the chain, and the following (Q-1) to (Q-11) The gene production represented by any of them is easy to manufacture. The number of carbon atoms in the methine chain having 1 to 9 carbon atoms does not include a group which represents a methine chain and may also have a ring structure in the chain, and further replaces the group of the linker (for example) The following carbon atoms of R 62 to R 67 and Z') (for example, carbon atoms at both ends of the linking group (Q-1)).
[化23A]
(式中,R62、R63、R64、R65、R66、R67及Z'各自獨立表示氫原子、羥基、鹵素原子、氰基、-NRR'、碳原子數6~12之芳基、碳原子數7~12之芳烷基或碳原子數1~8之烷基,R62~R67及Z'所表示之-NRR'、芳基、芳烷基及烷基可經羥基、鹵素原子、氰基或-NRR'取代,亦可被-O-、-S-、-CO-、-COO-、-OCO-、-SO2-、-NH-、-CONH-、-NHCO-、-N=CH-或-CH=CH-切斷,R及R'表示碳原子數6~12之芳基、碳原子數7~12之芳烷基或碳原子數1~8之烷基)。 (wherein R 62 , R 63 , R 64 , R 65 , R 66 , R 67 and Z' each independently represent a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, -NRR', and a carbon number of 6 to 12 a group, an aralkyl group having 7 to 12 carbon atoms or an alkyl group having 1 to 8 carbon atoms, and -NRR', an aryl group, an aralkyl group and an alkyl group represented by R 62 to R 67 and Z' may have a hydroxyl group. , halogen atom, cyano group or -NRR' substituted, may also be -O-, -S-, -CO-, -COO-, -OCO-, -SO 2 -, -NH-, -CONH-, -NHCO -, -N=CH- or -CH=CH-cut, R and R' represent an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms or an alkane having 1 to 8 carbon atoms base).
作為上述之R62~R67及Z'所表示之鹵素原子,可列舉:作為R01、R02、R03、R04及R05所表示之鹵素原子所例示之基。 The halogen atom represented by the above R 62 to R 67 and Z' may be exemplified as the halogen atom represented by R 01 , R 02 , R 03 , R 04 and R 05 .
作為上述之R62~R67、Z'、R及R'所表示之碳原子數6~12之芳基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數6~20之芳基所例示之基中滿足特定碳數的基等,作為上述之R62~R67、Z'、R及R'所表示之碳原子數7~12之芳烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數 6~20之芳基所例示之基中滿足特定碳數的基等。 Examples of the aryl group having 6 to 12 carbon atoms represented by R 62 to R 67 , Z′, R and R′ described above include R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . The group exemplified in the aryl group having 6 to 20 carbon atoms represented by the group, and the like, and the number of carbon atoms represented by the above R 62 to R 67 , Z′, R and R′ is 7 to 12 Examples of the aralkyl group include a group satisfying a specific carbon number, such as an aryl group having 6 to 20 carbon atoms represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . .
上述通式(9)中,作為Anq-所表示之陰離子,可列舉:作為上述通式(8)中之Anq-所表示之陰離子所例示之基等。 In the general formula (9), as the anion represented by An q-, include: An q- in the general formula (. 8) in the represented embodiment of the anions of the group shown.
作為上述通式(10)中之2個D以及上述通式(11)、(12)中之D及D',係以作為化合物電荷成為中性之方式選擇1個非離子性基與1個陽離子性基。 As the two D in the above formula (10) and D and D' in the above formulas (11) and (12), one nonionic group and one one are selected so that the charge of the compound becomes neutral. Cationic group.
作為上述通式(10)~(12)中之R53~R63及R53'~R63'所表示之鹵素原子、可取代R53及R53'所表示之芳基、芳烷基及烷基之鹵素原子、以及可取代Y12、Y12'及Y13所表示之烷基、芳基及芳烷基之鹵素原子,可列舉:作為R01、R02、R03、R04及R05所表示之鹵素原子所例示之基。 The halogen atom represented by R 53 to R 63 and R 53 ' to R 63 ' in the above formulas (10) to (12), the aryl group and the aralkyl group which may be substituted by R 53 and R 53 ' and The halogen atom of the alkyl group and the halogen atom which can substitute the alkyl group, the aryl group and the aralkyl group represented by Y 12 , Y 12 ' and Y 13 include R 01 , R 02 , R 03 and R 04 and The group represented by the halogen atom represented by R 05 .
作為R53~R63及R53'~R63'以及Y12、Y12'及Y13所表示之碳原子數6~30之芳基,可列舉:苯基、萘基、2-甲基苯基、3-甲基苯基、4-甲基苯基、4-乙烯基苯基、3-異丙基苯基、4-異丙基苯基、4-丁基苯基、4-異丁基苯基、4-第三丁基苯基、4-己基苯基、4-環己基苯基、4-辛基苯基、4-(2-乙基己基)苯基、4-硬脂基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4-二-第三丁基苯基、2,5-二-第三丁基苯基、2,6-二-第三丁基苯基、2,4-二-第三戊基苯基、2,5-二-第三戊基苯基、2,5-二-第三辛基苯基、2,4-二異丙苯基苯基、4-環己基苯基、(1,1'-聯苯)-4-基、2,4,5-三甲基苯基、二茂鐵基等,作為R53~R63及R53'-~R63'以及Y12、Y12'及Y13所表示之碳原子數7~30之芳烷基,可列舉:苄基、苯乙基、2-苯基丙烷-2-基、二苯基甲基、三苯基甲基、苯乙烯基、苯烯丙基、二茂鐵基甲基、二茂鐵基丙基等,作為R53~R63及R53'~R63'所表示之碳原子數1~8之烷基、以及 Y12、Y12'及Y13所表示之碳原子數1~20之烷基,可列舉:作為R01、R02、R03、R04及R05以及R1所表示之碳原子數1~40之烷基所例示之基中滿足特定碳數的基等。 Examples of the aryl group having 6 to 30 carbon atoms represented by R 53 to R 63 and R 53 ' to R 63 ' and Y 12 , Y 12 ' and Y 13 include a phenyl group, a naphthyl group and a 2-methyl group. Phenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-iso Butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, 4-stearyl Phenylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethyl Phenylphenyl, 3,5-dimethylphenyl, 2,4-di-t-butylphenyl, 2,5-di-t-butylphenyl, 2,6-di-t-butyl Phenyl, 2,4-di-third amylphenyl, 2,5-di-third amylphenyl, 2,5-di-t-octylphenyl, 2,4-diisopropylbenzene Phenylphenyl, 4-cyclohexylphenyl, (1,1'-biphenyl)-4-yl, 2,4,5-trimethylphenyl, ferrocene, etc., as R 53 ~ R 63 and R 53 ' -~R 63 ' and the aralkyl group having 7 to 30 carbon atoms represented by Y 12 , Y 12 ' and Y 13 may, for example, be a benzyl group, a phenethyl group or a 2-phenylpropane-2- Base, diphenylmethyl, triphenyl As R 53 ~ R 63 R 53, and the number '~ R 63' represents the carbon atom of the methyl group, a styryl group, an allyl benzene, methyl ferrocene, propyl ferrocene group having 1 to 8 The alkyl group and the alkyl group having 1 to 20 carbon atoms represented by Y 12 , Y 12 ' and Y 13 may be represented by R 01 , R 02 , R 03 , R 04 and R 05 and R 1 . A group satisfying a specific carbon number among the groups exemplified by the alkyl group having 1 to 40 carbon atoms.
上述通式(10)~(12)中,作為X12、X12'、X13及X13'所表示之碳原子數3~6之環烷-1,1-二基,可列舉:環丙烷-1,1-二基、環丁烷-1,1-二基、2,4-二甲基環丁烷-1,1-二基、3,3-二甲基環丁烷-1,1-二基、環丁烷-1,1-二基、環己烷-1,1-二基等。 In the above formulae (10) to (12), examples of the cycloalkane-1,1-diyl group having 3 to 6 carbon atoms represented by X 12 , X 12 ' , X 13 and X 13' include a ring. Propane-1,1-diyl, cyclobutane-1,1-diyl, 2,4-dimethylcyclobutane-1,1-diyl, 3,3-dimethylcyclobutane-1 , 1-diyl, cyclobutane-1,1-diyl, cyclohexane-1,1-diyl and the like.
作為上述通式(9)~(12)所表示之化合物之具體例,可列舉:下述[化24]所表示之化合物,但本發明並不受該等化合物限制。 Specific examples of the compound represented by the above formulas (9) to (12) include the compounds represented by the following [Chem. 24], but the present invention is not limited by these compounds.
本發明之化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有至少一個上述通式(1)所表示之結構者,該化合物之製造方法並無特別限定,例如可列舉藉由如下方式而獲得之方法,即藉由公知之方法而製造作為於自紫外至近紅外之波長 區域具有吸收極大值之有機色素之氰基苯乙烯化合物、三芳基甲烷化合物、花青化合物後,使其與醯氯化物、Boc化試劑、烷基鹵化物化合物、矽基氯化物化合物、烯丙醚化合物等進行反應,而導入上述通式(1)所表示之結構。 The compound of the present invention is an organic dye having an absorption maximum value in a wavelength region from the ultraviolet to the near-infrared, and has at least one structure represented by the above formula (1) in the molecule, and the method for producing the compound is not particularly limited. For example, a method obtained by a known method for producing a wavelength from the ultraviolet to the near infrared by a known method can be cited. a cyanostyrene compound, a triarylmethane compound, or a cyanine compound having an absorption of an organic dye having a maximum value, and then reacting with a ruthenium chloride, a Boc reagent, an alkyl halide compound, a sulfhydryl chloride compound, an allylic acid The ether compound or the like is reacted to introduce a structure represented by the above formula (1).
本發明之化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有至少一個上述通式(1)所表示之結構者,該化合物除可作為染料用於以下所說明之著色感光性組合物外,亦可用於顯示器或光學透鏡所使用之光學濾光片、銀鹽照片用感光材料、染物、塗料、油墨、電子照片感光體、增色劑、感熱記錄紙、轉印色帶、光學記錄色素、太陽電池、有機半導體、臨床檢測試劑、雷射治療用色素、染色等。 The compound of the present invention is an organic dye having an absorption maximum value in a wavelength region from ultraviolet to near-infrared, and has at least one structure represented by the above formula (1) in the molecule, and the compound can be used as a dye in the following In addition to the color-sensitive composition described, it can also be used for optical filters used in displays or optical lenses, photosensitive materials for silver salt photos, dyes, paints, inks, electrophotographic photoreceptors, toners, thermal recording papers, and Printing ribbons, optical recording pigments, solar cells, organic semiconductors, clinical testing reagents, pigments for laser treatment, dyeing, etc.
又,除可作為抗氧化劑用於光硬化性組合物、熱硬化性組合物或聚合性組合物外,亦可作為顯色劑用於感熱材料。 Further, in addition to being used as an antioxidant, the photocurable composition, the thermosetting composition, or the polymerizable composition may be used as a coloring agent for a heat sensitive material.
本發明之化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有至少一個上述通式(1)所表示之結構者,該化合物於上述通式(1)中R1並非氫原子之情形時,亦可用作潛伏性添加劑。 The compound of the present invention is an organic dye having an absorption maximum value in a wavelength region from ultraviolet to near-infrared, and has at least one structure represented by the above formula (1) in the molecule, and the compound is in the above formula (1). When R 1 is not a hydrogen atom, it can also be used as a latent additive.
所謂潛伏性添加劑,係於常溫或150℃以下之預烤步驟中為惰性,且藉由於100~250℃下進行加熱、或者於酸/鹼觸媒存在下於80~200℃下進行加熱,從而保護基脫離而成為活性者,具體而言,可列舉:潛伏性抗氧化劑、潛伏性紫外線吸收劑等潛伏性樹脂添加劑;感熱紙用潛伏性顯色劑;感熱紙用潛伏性保存穩定劑;潛伏性硬化劑等。 The latent additive is inert in a pre-bake step at normal temperature or below 150 ° C, and is heated at 100 to 250 ° C or at 80 to 200 ° C in the presence of an acid/base catalyst. The protective group is deactivated and becomes active, and specific examples thereof include latent resin additives such as latent antioxidants and latent ultraviolet absorbers; latent developers for thermal paper; latent storage stabilizers for thermal paper; Sclerosing agent, etc.
繼而,對含有本發明之化合物之組合物進行說明,本發明之化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有至少一個上述通式(1)所表示之結構者。 Next, the composition containing the compound of the present invention is described. The compound of the present invention is an organic dye having an absorption maximum value in a wavelength range from ultraviolet to near-infrared, and has at least one of the above formula (1) in the molecule. The structure of the person.
含有本發明之化合物之組合物除可用作著色感光性組合物外,亦可用作聚合性組合物,本發明之化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有至少一個上述通式(1)所表示之結構者。 The composition containing the compound of the present invention can be used as a polymerizable composition in addition to a coloring photosensitive composition, and the compound of the present invention is an organic dye having an absorption maximum value in a wavelength region from ultraviolet to near-infrared, and It has at least one structure represented by the above formula (1) in the molecule.
於用作上述著色感光性組合物之情形時,本發明之化合物之含量較佳為0.01~50質量%,更佳為0.1~30質量%,本發明之化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有至少一個上述通式(1)所表示之結構者。 When used as the coloring photosensitive composition, the content of the compound of the present invention is preferably from 0.01 to 50% by mass, more preferably from 0.1 to 30% by mass, and the compound of the present invention is in the wavelength range from ultraviolet to near-infrared. An organic dye having an absorption maximum value and having at least one structure represented by the above formula (1) in the molecule.
上述著色感光性組合物係藉由光照射而硬化者,可為光陽離子硬化性、光陰離子硬化性或光自由基硬化性中之任一者,但較佳為光自由基硬化性。 The colored photosensitive composition is cured by light irradiation, and may be any of photocationic curability, photoanionic curability, and photoradical hardenability, but is preferably photoradical hardenability.
於上述著色感光性組合物為光自由基硬化性之情形時,著色感光性組合物除以本發明之化合物為必須成分外,亦以具有酸值之具有乙烯性不飽和鍵之聚合性化合物及光自由基聚合起始劑為必須成分,本發明之化合物係於自紫外至近紅外之波長區域具有吸收極大值之有機色素,且於分子內具有至少一個上述通式(1)所表示之結構者。以下,將該著色感光性組合物亦稱為本發明之著色感光性組合物。 When the coloring photosensitive composition is photo-radically curable, the coloring photosensitive composition is a polymerizable compound having an acid value and having an ethylenically unsaturated bond, in addition to the compound of the present invention as an essential component. The photoradical polymerization initiator is an essential component, and the compound of the present invention is an organic pigment having an absorption maximum value in a wavelength region from ultraviolet to near-infrared, and has at least one structure represented by the above formula (1) in the molecule. . Hereinafter, the colored photosensitive composition is also referred to as the colored photosensitive composition of the present invention.
作為上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物,可列舉:(甲基)丙烯酸、α-氯丙烯酸、伊康酸、馬來酸、檸康酸、富馬酸、雙環庚烯二甲酸、丁烯酸、異丁烯酸、乙烯基乙酸、烯丙基乙酸、肉桂酸、山梨酸、中康酸、琥珀酸單[2-(甲基)丙烯醯氧基乙基]酯、鄰苯二甲酸單[2-(甲基)丙烯醯氧基乙基]酯、ω-羧基聚己內酯單(甲基)丙烯酸酯等兩末端具有羧基與羥基之聚合物之單(甲基)丙烯酸酯、(甲基)丙烯酸羥基乙酯.馬來酸酯、(甲基)丙烯酸羥基丙酯.馬來酸酯、二環戊二烯.馬來酸酯或者具有1個羧基與2個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯等不飽和多元酸;苯酚及/或甲酚酚醛 清漆環氧樹脂、具有聯苯骨架、萘骨架之酚醛清漆環氧樹脂、雙酚A酚醛清漆型環氧化合物、二環戊二烯酚醛清漆型環氧化合物等酚醛清漆型環氧化合物、具有多官能環氧基之聚苯甲烷型環氧樹脂、使不飽和一元酸作用於下述通式(13)所表示之環氧化合物等之環氧樹脂之環氧基,進而使多元酸酐作用而獲得之樹脂、季戊四醇三丙烯酸酯、二季戊四醇五丙烯酸酯等含羥基之多官能丙烯酸酯與琥珀酸酐、鄰苯二甲酸酐、四氫鄰苯二甲酸酐等二元酸酐之反應物,即具有酸值之多官能丙烯酸酯等聚合物。 Examples of the polymerizable compound having an ethylenic unsaturated bond having an acid value include (meth)acrylic acid, α-chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, and bicycloheptene. Dicarboxylic acid, crotonic acid, methacrylic acid, vinyl acetic acid, allyl acetic acid, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2-(methyl) propylene methoxyethyl] ester, o-benzene Mono(meth)acrylic acid having a polymer of a carboxyl group and a hydroxyl group at both terminals, such as mono[2-(methyl)acryloxyethyl)dicarboxylate or ω-carboxypolycaprolactone mono(meth)acrylate Ester, hydroxyethyl (meth) acrylate. Maleate, hydroxypropyl (meth)acrylate. Maleate, dicyclopentadiene. Maleic acid ester or unsaturated polybasic acid such as polyfunctional (meth) acrylate having one carboxyl group and two or more (meth) acrylonitrile groups; phenol and/or cresol novolac Varnish epoxy resin, novolak epoxy resin with biphenyl skeleton, naphthalene skeleton, bisphenol A novolak epoxy compound, dicyclopentadiene novolac epoxy compound, etc. A polyphenylene type epoxy resin having a functional epoxy group, an epoxy group of an epoxy resin such as an epoxy compound represented by the following formula (13), and an aromatic acid anhydride; a reactant of a hydroxyl group-containing polyfunctional acrylate such as a resin, pentaerythritol triacrylate or dipentaerythritol pentaacrylate, and a dibasic acid anhydride such as succinic anhydride, phthalic anhydride or tetrahydrophthalic anhydride, which has an acid value A polymer such as a polyfunctional acrylate.
(式中,X41表示直接鍵、亞甲基、碳原子數1~4之亞烷基、碳原子數3~20之脂環式烴基、-O-、-S-、-SO2-、-SS-、-SO-、-CO-、-OCO-或上述(3-1)~(3-3)所表示之取代基,該亞烷基可經鹵素原子取代,R68、R69、R70及R71分別獨立表示氫原子、碳原子數1~5之烷基、碳原子數1~8之烷氧基、碳原子數2~5之烯基或鹵素原子,上述烷基、烷氧基及烯基可經鹵素原子取代,s為0~10之整數)。 (wherein X 41 represents a direct bond, a methylene group, an alkylene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, -O-, -S-, -SO 2 -, -SS-, -SO-, -CO-, -OCO- or a substituent represented by the above (3-1) to (3-3), which may be substituted by a halogen atom, R 68 , R 69 , R 70 and R 71 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or a halogen atom, and the above alkyl group and alkane. The oxy group and the alkenyl group may be substituted by a halogen atom, and s is an integer of 0 to 10).
該等聚合性化合物可單獨或混合2種以上使用,又,可與不具有酸值之具有乙烯性不飽和鍵之聚合性化合物組合使用。於混合2種以上使用之情形時,亦可事先使該等共聚合而以共聚物之形態使用。 These polymerizable compounds may be used singly or in combination of two or more kinds, and may be used in combination with a polymerizable compound having an ethylenically unsaturated bond having no acid value. When two or more types are used in combination, the copolymerization may be carried out in advance in the form of a copolymer.
作為上述不具有酸值之具有乙烯性不飽和鍵之聚合性化合物,例如可列舉:(甲基)丙烯酸-2-羥基乙酯、(甲基)丙烯酸-2-羥基丙酯、(甲基)丙烯酸縮水甘油酯、下述化合物No.A1~No.A4、(甲基)丙烯酸 甲酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸二甲胺基甲酯、(甲基)丙烯酸二甲胺基乙酯、(甲基)丙烯酸胺基丙酯、(甲基)丙烯酸二甲胺基丙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸聚(乙氧基)乙酯、(甲基)丙烯酸丁氧基乙氧基乙酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸四氫呋喃酯、(甲基)丙烯酸乙烯酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸苄酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、三羥甲基乙烷三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、二氫芳樟醇二(甲基)丙烯酸酯、異氰尿酸三[(甲基)丙烯醯基乙基]酯、(甲基)丙烯酸聚酯低聚物等不飽和一元酸及多元醇或多酚之酯;(甲基)丙烯酸鋅、(甲基)丙烯酸鎂等不飽和多元酸之金屬鹽;馬來酸酐、伊康酸酐、檸康酸酐、甲基四氫鄰苯二甲酸酐、四氫鄰苯二甲酸酐、三烷基四氫鄰苯二甲酸酐、5-(2,5-二側氧四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、三烷基四氫鄰苯二甲酸酐-馬來酸酐加成物、十二烯基琥珀酸酐、甲基雙環庚烯二甲酸酐等不飽和多元酸之酸酐;(甲基)丙烯醯胺、亞甲基雙-(甲基)丙烯醯胺、二伸乙基三胺三(甲基)丙烯醯胺、苯二甲基雙(甲基)丙烯醯胺、α-氯丙烯醯胺、N-2-羥基乙基(甲基)丙烯醯胺等不飽和一元酸及多價胺之醯胺;丙烯醛等不飽和醛;(甲基)丙烯腈、α-氯丙烯腈、二氰亞乙烯、烯丙基氰等不飽和腈;苯乙烯、4-甲基苯乙烯、4-乙基 苯乙烯、4-甲氧基苯乙烯、4-羥基苯乙烯、4-氯苯乙烯、二乙烯苯、乙烯基甲苯、苯甲酸、乙烯酚、磺酸乙烯酯、4-乙烯基苯磺酸、乙烯基苄基甲醚、乙烯基苄基縮水甘油醚等不飽和芳香族化合物;甲基乙烯基酮等不飽和酮;乙烯胺、烯丙胺、N-乙烯基吡咯啶酮、乙烯基哌啶等不飽和胺化合物;乙烯基甲醚、乙烯基乙醚、正丁基乙烯醚、異丁基乙烯醚、烯丙基縮水甘油醚等乙烯醚;馬來醯亞胺、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺等不飽和醯亞胺類;茚、1-甲基茚等茚類;1,3-丁二烯、異戊二烯、氯丁二烯等脂肪族共軛二烯類;聚苯乙烯、聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸正丁酯、聚矽氧烷等聚合物分子鏈之末端具有單(甲基)丙烯醯基之巨單體類;(甲基)丙烯腈、乙烯、丙烯、丁烯、氯乙烯、乙酸乙烯酯等其他乙烯系化合物、及聚甲基丙烯酸甲酯巨單體、聚苯乙烯巨單體等巨單體類、三環癸烷骨架之單甲基丙烯酸酯、N-苯基馬來醯亞胺、甲基丙烯醯氧基甲基-3-乙基氧雜環丁烷等、與(甲基)丙烯酸之共聚物及使該等與如昭和電工(股)公司製造之Karenz MOI、AOI之具有不飽和鍵之異氰酸酯化合物反應而成的(甲基)丙烯酸之共聚物、或氯乙烯、偏二氯乙烯、二乙烯基琥珀醯、鄰苯二甲酸二烯丙酯、磷酸三烯丙酯、異氰尿酸三烯丙酯、乙烯基硫醚、乙烯基咪唑、乙烯基唑啉、乙烯基咔唑、乙烯基吡咯啶酮、乙烯基吡啶、含羥基之乙烯基單體及聚異氰酸酯化合物之乙烯基胺基甲酸酯化合物、含羥基之乙烯基單體及聚環氧化合物之乙烯系環氧化合物、季戊四醇三丙烯酸酯、二季戊四醇五丙烯酸酯等含羥基之多官能丙烯酸酯與甲苯二異氰酸酯、六亞甲基二異氰酸酯等多官能異氰酸酯之反應物等。 Examples of the polymerizable compound having an ethylenically unsaturated bond having no acid value include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and (methyl). Glycidyl acrylate, the following compounds No. A1 to No. A4, methyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate , cyclohexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isodecyl (meth)acrylate, stearyl (meth)acrylate, (methyl) Lauryl acrylate, methoxyethyl (meth)acrylate, dimethylaminomethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, aminopropyl (meth)acrylate, ( Methyl) dimethylaminopropyl acrylate, ethoxyethyl (meth) acrylate, poly(ethoxy)ethyl (meth) acrylate, butoxyethoxyethyl (meth) acrylate, Ethylhexyl (meth)acrylate, phenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, vinyl (meth)acrylate, allyl (meth)acrylate, (methyl) Benzyl acrylate Ester, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol Di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, trimethylolethane tri(meth)acrylic acid Ester, trimethylolpropane tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (methyl) Unsaturated monobasic acid and polybasic acid such as acrylate, dihydrolinarol di(meth)acrylate, tris(meth)propenylethyl]isocyanurate, (meth)acrylic polyester oligomer An alcohol or a polyphenol ester; a metal salt of an unsaturated polybasic acid such as zinc (meth)acrylate or magnesium (meth)acrylate; maleic anhydride, itaconic anhydride, citraconic anhydride, methyltetrahydrophthalic anhydride , tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5-(2,5-di-oxo-tetrahydrofuranyl)-3-methyl-3-cyclohexene-1,2-di Carboxylic anhydride, trialkyltetrahydroortho An anhydride of an unsaturated polybasic acid such as a dicarboxylic anhydride-maleic anhydride adduct, dodecenyl succinic anhydride, methyl biscycloheptylene anhydride; (meth) acrylamide, methylene bis-(methyl Ethylene decylamine, di-ethyltriamine tris(meth) acrylamide, benzyldimethylbis(methyl) decylamine, α-chloropropenylamine, N-2-hydroxyethyl (methyl) An unsaturated monobasic acid such as acrylamide or a polyamine of a polyvalent amine; an unsaturated aldehyde such as acrolein; an unsaturated nitrile such as (meth)acrylonitrile, α-chloroacrylonitrile, dicyandiethylene or allyl cyanide; Styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, benzoic acid, ethylene Unsaturated aromatic compounds such as phenol, vinyl sulfonate, 4-vinylbenzenesulfonic acid, vinylbenzyl methyl ether, vinylbenzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; vinylamine, olefin An unsaturated amine compound such as propylamine, N-vinylpyrrolidone or vinylpiperidine; vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, allyl condensation a vinyl ether such as glyceryl ether; an unsaturated quinone imine such as maleic imine, N-phenyl maleimide or N-cyclohexylmaleimide; anthracene such as hydrazine or 1-methylhydrazine; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene, chloroprene; polystyrene, poly(methyl) acrylate, n-butyl poly(meth) acrylate, poly a macromonomer having a mono(meth)acrylonitrile group at the end of a polymer molecular chain such as a siloxane; a vinyl compound such as (meth)acrylonitrile, ethylene, propylene, butylene, vinyl chloride or vinyl acetate And macromonomers such as polymethyl methacrylate macromonomers, polystyrene macromonomers, monomethacrylates of tricyclodecane skeleton, N-phenylmaleimide, methacrylium oxime a copolymer of (meth)acrylic acid, such as oxymethyl-3-ethyloxetane, and an isocyanate having an unsaturated bond, such as Karenz MOI and AOI manufactured by Showa Denko Co., Ltd. a copolymer of (meth)acrylic acid obtained by reacting a compound, or vinyl chloride, vinylidene chloride, divinylarene, diallyl phthalate, triallyl phosphate, Triallyl cyanurate, divinyl sulfide, vinyl imidazole, vinyl Oxazoline, vinyl carbazole, vinyl pyrrolidone, vinyl pyridine, hydroxyl group-containing vinyl monomer and vinyl urethane compound of polyisocyanate compound, hydroxyl group-containing vinyl monomer and polyepoxy A reaction product of a hydroxyl group-containing polyfunctional acrylate such as a vinyl epoxy compound, pentaerythritol triacrylate or dipentaerythritol pentaacrylate, a polyfunctional isocyanate such as toluene diisocyanate or hexamethylene diisocyanate, or the like.
[化26]
為了進行酸值調整而改良本發明之著色感光性組合物之顯影性,可與上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物一起進而使用單官能或多官能環氧化合物。上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物較佳為固形物成分之酸值為5~120mgKOH/g之範圍,單官能或多官能環氧化合物之使用量較佳為以滿足上述酸值之方式進行選擇。 In order to improve the developability of the coloring photosensitive composition of the present invention in order to adjust the acid value, a monofunctional or polyfunctional epoxy compound may be further used together with the above polymerizable compound having an acid value and an ethylenically unsaturated bond. The polymerizable compound having an acid value and having an ethylenically unsaturated bond preferably has an acid value of a solid content of 5 to 120 mgKOH/g, and a monofunctional or polyfunctional epoxy compound is preferably used to satisfy the above. The way of acid value is chosen.
作為上述單官能環氧化合物,可列舉:甲基丙烯酸縮水甘油 酯、甲基縮水甘油醚、乙基縮水甘油醚、丙基縮水甘油醚、異丙基縮水甘油醚、丁基縮水甘油醚、異丁基縮水甘油醚、第三丁基縮水甘油醚、戊基縮水甘油醚、己基縮水甘油醚、庚基縮水甘油醚、辛基縮水甘油醚、壬基縮水甘油醚、癸基縮水甘油醚、十一烷基縮水甘油醚、十二烷基縮水甘油醚、十三烷基縮水甘油醚、十四烷基縮水甘油醚、十五烷基縮水甘油醚、十六烷基縮水甘油醚、2-乙基己基縮水甘油醚、烯丙基縮水甘油醚、炔丙基縮水甘油醚、對甲氧基乙基縮水甘油醚、苯基縮水甘油醚、對甲氧基縮水甘油醚、對丁基苯酚縮水甘油醚、甲苯基縮水甘油醚、2-甲基甲苯基縮水甘油醚、4-壬基苯基縮水甘油醚、苄基縮水甘油醚、對異丙苯基苯基縮水甘油醚、三苯甲基縮水甘油醚、甲基丙烯酸2,3-環氧丙酯、環氧化大豆油、環氧化亞麻仁油、丁酸縮水甘油酯、一氧化乙烯基環己烷、1,2-環氧-4-乙烯基環己烷、環氧苯乙烷、氧化蒎烯、甲基環氧苯乙烷、環氧環己烷、環氧丙烷等。 As the above monofunctional epoxy compound, glycidyl methacrylate is exemplified. Ester, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, tert-butyl glycidyl ether, pentyl Glycidyl ether, hexyl glycidyl ether, heptyl glycidyl ether, octyl glycidyl ether, decyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, ten Trialkyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, propargyl Glycidyl ether, p-methoxyethyl glycidyl ether, phenyl glycidyl ether, p-methoxyglycidyl ether, p-butyl phenol glycidyl ether, cresyl glycidyl ether, 2-methyltolyl glycidol Ether, 4-mercaptophenyl glycidyl ether, benzyl glycidyl ether, p-cumyl phenyl glycidyl ether, trityl glycidyl ether, 2,3-epoxypropyl methacrylate, ring Oxidized soybean oil, epoxidized linseed oil, butyric acid Oleate, vinyl cyclohexane oxide, 1,2-epoxy-4-vinylcyclohexane, styrene oxide, decene oxide, methyl epoxide, epoxy cyclohexane, Propylene oxide and the like.
作為上述多官能環氧化合物,若使用選自由雙酚型環氧化合物及縮水甘油醚類所組成之群中之一種以上,則可獲得特性進一步良好之著色感光性組合物,故而較佳。作為該雙酚型環氧化合物,除可使用上述通式(13)所表示之環氧化合物外,例如亦可使用氫化雙酚型環氧化合物等雙酚型環氧化合物。作為該縮水甘油醚類,可列舉:乙二醇二縮水甘油醚、丙二醇二縮水甘油醚、1,4-丁二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、1,8-辛二醇二縮水甘油醚、1,10-癸二醇二縮水甘油醚、2,2-二甲基-1,3-丙二醇二縮水甘油醚、二乙二醇二縮水甘油醚、三乙二醇二縮水甘油醚、四乙二醇二縮水甘油醚、六乙二醇二縮水甘油醚、1,4-環己烷二甲醇二縮水甘油醚、1,1,1-三(縮水甘油氧基甲基)丙烷、1,1,1-三(縮水甘油氧基甲基)乙烷、1,1,1-三(縮水甘油氧基甲基)甲烷、1,1,1,1-四(縮水甘油氧基甲基)甲烷。 When one or more selected from the group consisting of a bisphenol type epoxy compound and a glycidyl ether is used as the polyfunctional epoxy compound, a coloring photosensitive composition having further excellent properties can be obtained, which is preferable. In addition to the epoxy compound represented by the above formula (13), a bisphenol epoxy compound such as a hydrogenated bisphenol epoxy compound can be used as the bisphenol epoxy compound. Examples of the glycidyl ethers include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, and 1,6-hexanediol diglycidyl ether. 8-octanediol diglycidyl ether, 1,10-nonanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, three Ethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether, 1,4-cyclohexane dimethanol diglycidyl ether, 1,1,1-tris (glycidol) Oxymethyl)propane, 1,1,1-tris(glycidoxymethyl)ethane, 1,1,1-tris(glycidoxymethyl)methane, 1,1,1,1- Tetrakis(glycidoxymethyl)methane.
除上述以外,亦可使用酚系酚醛清漆型環氧化合物、聯苯酚醛清漆型環氧化合物、甲酚酚醛清漆型環氧化合物、雙酚A酚醛清漆型環氧化合物、二環戊二烯酚醛清漆型環氧化合物等酚醛清漆型環氧化合物;3,4-環氧-6-甲基環己基甲基-3,4-環氧-6-甲基環己烷羧酸酯、3,4-環氧環己基甲基-3,4-環氧環己烷羧酸酯、1-環氧乙基-3,4-環氧環己烷等脂環式環氧化合物;鄰苯二甲酸二縮水甘油酯、四氫鄰苯二甲酸二縮水甘油酯、二聚酸縮水甘油酯等縮水甘油酯類;四縮水甘油基二胺基二苯甲烷、三縮水甘油基-對胺基苯酚、N,N-二縮水甘油基苯胺等縮水甘油胺類;1,3-二縮水甘油基-5,5-二甲尿囊素、三縮水甘油基異氰尿酸酯等雜環式環氧化合物;二氧化二環戊二烯等二氧化物化合物;萘型環氧化合物、三苯甲烷型環氧化合物、二環戊二烯型環氧化合物等。 In addition to the above, a phenol novolak type epoxy compound, a biphenol novolak type epoxy compound, a cresol novolak type epoxy compound, a bisphenol A novolac type epoxy compound, a dicyclopentadiene phenol aldehyde can also be used. A novolac type epoxy compound such as a varnish type epoxy compound; 3,4-epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4 - an alicyclic epoxy compound such as epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate or 1-epoxyethyl-3,4-epoxycyclohexane; Glycidyl esters such as glycidyl ester, tetrahydrophthalic acid diglycidyl ester, dimer acid glycidyl ester; tetraglycidyl diaminodiphenylmethane, triglycidyl-p-aminophenol, N, a glycidylamine such as N-diglycidylaniline; a heterocyclic epoxy compound such as 1,3-diglycidyl-5,5-dimethyl allantoin or triglycidyl isocyanurate; A dioxide compound such as dicyclopentadiene oxide; a naphthalene type epoxy compound, a triphenylmethane type epoxy compound, a dicyclopentadiene type epoxy compound, or the like.
於本發明之著色感光性組合物中,上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物之含量於本發明之著色感光性組合物中較佳為1~95質量%,尤佳為10~80質量%。 In the coloring photosensitive composition of the present invention, the content of the polymerizable compound having an acid value and having an ethylenically unsaturated bond is preferably from 1 to 95% by mass, more preferably from 1 to 95% by mass, based on the coloring photosensitive composition of the present invention. 10~80% by mass.
又,於使用上述不具有酸值之具有乙烯性不飽和鍵之聚合性化合物之情形時,其含量相對於上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物100質量份,較佳為設為10~1000質量份。 In the case where the above polymerizable compound having an ethylenic unsaturated bond having no acid value is used, the content thereof is preferably 100 parts by mass based on 100 parts by mass of the above-mentioned polymerizable compound having an ethylenically unsaturated bond having an acid value. Set to 10 to 1000 parts by mass.
上述光自由基聚合起始劑只要為可藉由受到光照射而開始自由基聚合之化合物即可,例如,可例示苯乙酮系化合物、苯偶醯系化合物、二苯甲酮系化合物、肟系化合物、9-氧硫系化合物等酮系化合物等作為較佳者。 The photo-radical polymerization initiator may be a compound which can be subjected to radical polymerization by light irradiation, and examples thereof include an acetophenone-based compound, a benzoin-based compound, a benzophenone-based compound, and an anthracene. Compound, 9-oxosulfur A ketone compound such as a compound is preferable.
作為上述苯乙酮系化合物,例如可列舉:二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、4'-異丙基-2-羥基-2-甲基苯丙酮、2-羥基甲基-2-甲基苯丙酮、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、對二甲胺基苯乙酮、對第三丁基二氯苯乙酮、對第三丁基三氯苯乙酮、對疊氮苯 亞甲基苯乙酮、1-羥基環己基苯基酮、2-甲基-1-[4-(甲硫基)苯基]-2-嗎啉基丙酮-1、2-苄基-2-二甲胺基-1-(4-嗎啉基苯基)-丁酮-1、安息香、安息香甲醚、安息香乙醚、安息香異丙醚、安息香正丁醚、安息香異丁醚、1-[4-(2-羥基乙氧基)-苯基]-2-羥基-2-甲基-1-丙烷-1-酮等。 Examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 4'-isopropyl-2-hydroxy- 2-methylpropiophenone, 2-hydroxymethyl-2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethane-1-one, p-dimethylaminophenyl Ketone, p-tert-butyldichloroacetophenone, p-tert-butyltrichloroacetophenone, p-azidobenzene Methylene acetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylacetone-1, 2-benzyl-2 -dimethylamino-1-(4-morpholinylphenyl)-butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, 1-[ 4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one and the like.
作為上述苯偶醯系化合物,可列舉:苯偶醯、茴香偶醯等。 Examples of the benzoin-based compound include benzoin, fentanyl and the like.
作為上述二苯甲酮系化合物,例如可列舉:二苯甲酮、鄰苯甲醯基苯甲酸甲酯、米其勒酮、4,4'-雙二乙基胺基二苯甲酮、4,4'-二氯二苯甲酮、4-苯甲醯基-4'-甲基二苯硫醚等。 Examples of the benzophenone-based compound include benzophenone, methyl ortho-benzoylbenzoate, mischrone, and 4,4'-bisdiethylaminobenzophenone. , 4'-dichlorobenzophenone, 4-benzylidene-4'-methyldiphenyl sulfide, and the like.
作為上述肟系化合物,可列舉:1,2-辛二酮,1-[4-(苯硫基)-,2-(O-苯甲醯基肟)]、乙酮,1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-,1-(0-乙醯基肟)、甲酮,(2-甲基苯基)[6-硝基-9-[3-(三甲基矽基)丙基]-9H-咔唑-3-基]-,1-O-乙醯基肟)、甲酮,(9-乙基-6-硝基-9H-咔唑-3-基)(2-甲基苯基),O-乙醯基肟、甲酮,(9-乙基-6-硝基-9H-咔唑-3-基)[2-甲基-4-(4-嗎啉基)苯基),O-乙醯基肟、甲酮,(3,5-二硝基苯基)(9-乙基-6-硝基-9H-咔唑-3-基)(2-甲基苯基),O-乙醯基肟、甲酮,(9-乙基-6-硝基-9H-咔唑-3-基)(3-硝基苯基),O-乙醯基肟、1,3,5-三-2,4,6(1H,3H,5H)-三酮、1,3,5-三[2-(乙醯氧基)-3-[3-[(1E)-1-[(乙醯氧基)亞胺基乙基]-6-硝基-9H-咔唑-9-基]丙基]-、1,2-丁二酮、1-[4-(苯硫基)苯基]-、2-(O-乙醯基肟)、1,2-丁二酮、1-[4-[[4-(2-羥基乙氧基)苯基]硫基]苯基]-、2-(O-乙醯基肟)、1,2-丁二酮、1,1'-(硫代二-4,1-伸苯基)雙-、2,2-雙(O-乙醯基肟)、1,2-丁二酮、1-[4-(苯硫基)苯基]-、2-[0-(4-甲基苯甲醯基)肟]等。 Examples of the above oxime-based compound include 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzylidenehydrazide), ethyl ketone, 1-[9- Ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]-, 1-(0-ethylindenyl), ketone, (2-methylphenyl) [ 6-Nitro-9-[3-(trimethylsulfonyl)propyl]-9H-indazol-3-yl]-, 1-O-ethylindenyl), ketone, (9-ethyl) -6-nitro-9H-indazol-3-yl)(2-methylphenyl), O-acetamidoxime, ketone, (9-ethyl-6-nitro-9H-carbazole- 3-yl)[2-methyl-4-(4-morpholinyl)phenyl), O-acetylindenyl, ketone, (3,5-dinitrophenyl)(9-ethyl- 6-nitro-9H-indazol-3-yl)(2-methylphenyl), O-acetamidoxime, ketone, (9-ethyl-6-nitro-9H-carbazole-3 -yl)(3-nitrophenyl), O-acetylindenyl, 1,3,5-three -2,4,6(1H,3H,5H)-trione, 1,3,5-tri[2-(ethyloxy)-3-[3-[(1E)-1-[( Oxy)iminoethyl]-6-nitro-9H-carbazol-9-yl]propyl]-, 1,2-butanedione, 1-[4-(phenylthio)phenyl] -, 2-(O-ethylindenyl), 1,2-butanedione, 1-[4-[[4-(2-hydroxyethoxy)phenyl]thio]phenyl]-, 2 -(O-acetylhydrazine), 1,2-butanedione, 1,1'-(thiodi-4,1-phenylene)bis-, 2,2-bis(O-ethenyl)肟), 1,2-butanedione, 1-[4-(phenylthio)phenyl]-, 2-[0-(4-methylbenzhydryl)fluorene, and the like.
作為上述9-氧硫系化合物,可列舉:9-氧硫、2-甲基9-氧硫、2-乙基9-氧硫、2-氯9-氧硫、2-異丙基9-氧硫、2,4-二乙基9-氧硫等。 As the above 9-oxygen sulfur a compound, which can be exemplified by 9-oxosulfur 2-methyl 9-oxosulfur 2-ethyl 9-oxosulfur 2-chloro 9-oxosulfur 2-isopropyl 9-oxosulfur 2,4-diethyl 9-oxosulfur Wait.
作為其他光自由基聚合起始劑,可列舉:2,4,6-三甲基苯甲醯基二苯基氧化膦、雙(環戊二烯基)-雙[2,6-二氟-3-(吡咯-1-基)]鈦等。 As other photoradical polymerization initiators, 2,4,6-trimethylbenzimidyldiphenylphosphine oxide, bis(cyclopentadienyl)-bis[2,6-difluoro- 3-(pyrrol-1-yl)]titanium or the like.
該等光自由基聚合起始劑可視所需之性能而調配1種或2種以上者使用。 These photo-radical polymerization initiators may be used in combination of one or more kinds depending on the desired properties.
如以上之光自由基聚合起始劑只要相對於自由基聚合性有機物質(上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物、不具有酸值之具有乙烯性不飽和鍵之聚合性化合物、單官能或多官能環氧化合物),使用化學計量必需量即可,但較佳為相對於自由基聚合性有機物質,可調配0.05~10質量份,進而較佳為可調配0.1~10質量份。若高於該範圍,則有未獲得具有充分強度之硬化物之情形,若低於該範圍,則有樹脂未充分硬化之情形。 The photoradical polymerization initiator as described above is only required to be polymerizable with a radically polymerizable organic substance (the above-mentioned polymerizable compound having an ethylenic unsaturated bond having an acid value and having an acid value and having an ethylenically unsaturated bond) The compound, the monofunctional or polyfunctional epoxy compound may be a stoichiometrically necessary amount, but preferably it is 0.05 to 10 parts by mass, and more preferably 0.1 to 10, with respect to the radically polymerizable organic substance. Parts by mass. If it is higher than this range, there is a case where a cured product having sufficient strength is not obtained, and if it is less than this range, the resin may not be sufficiently cured.
於本發明之著色感光性組合物中,上述光自由基聚合起始劑之含量於本發明之著色感光性組合物中較佳為0.1~30質量%,尤佳為0.5~10質量%。若上述光聚合起始劑之含量小於0.1質量%,則有利用曝光之硬化變得不充分之情形,若上述光聚合起始劑之含量大於30質量%,則有於著色感光性組合物中起始劑析出之情形。 In the coloring photosensitive composition of the present invention, the content of the photoradical polymerization initiator is preferably from 0.1 to 30% by mass, particularly preferably from 0.5 to 10% by mass, based on the coloring photosensitive composition of the present invention. When the content of the photopolymerization initiator is less than 0.1% by mass, the curing by exposure may be insufficient, and if the content of the photopolymerization initiator is more than 30% by mass, it may be in the coloring photosensitive composition. The case where the initiator is precipitated.
本發明之著色感光性組合物可視需要而溶解或分散於有機溶劑中,利用旋轉塗佈機、輥式塗佈機、棒式塗佈機、模嘴塗佈機、簾幕式塗佈機、各種印刷、浸漬等公知之機構,將所獲得之塗液塗佈於鈉玻璃、石英玻璃、半導體基板、金屬、紙、塑膠等支持基體上,進行光照射而進行硬化。 The colored photosensitive composition of the present invention may be dissolved or dispersed in an organic solvent as needed, and may be a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, or the like. Various known mechanisms such as printing and immersion apply the obtained coating liquid to a supporting substrate such as soda glass, quartz glass, a semiconductor substrate, metal, paper, or plastic, and perform light irradiation to be cured.
作為上述有機溶劑,可列舉通常視需要而可溶解或分散上述各成分之溶劑,例如甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環己酮、2-庚酮等酮類;乙醚、二烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲醚等醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸 正丁酯、乙酸環己酯、乳酸乙酯、琥珀酸二甲酯、TEXANOL等酯系溶劑;乙二醇單甲醚、乙二醇單乙醚等溶纖素系溶劑;甲醇、乙醇、異或正丙醇、異或正丁醇、戊醇等醇系溶劑;乙二醇單乙酸甲酯、乙二醇單乙酸乙酯、丙二醇-1-單甲醚-2-乙酸酯(PGMEA)、二丙二醇單甲醚乙酸酯、乙酸3-甲氧基丁酯、丙酸乙氧基乙酯等醚酯系溶劑;苯、甲苯、二甲苯等BTX系溶劑;己烷、庚烷、辛烷、環己烷等脂肪族烴系溶劑;松節油、D-檸檬烯、蒎烯等萜烯系烴油;礦油精、Swazol # 310(科斯莫松山石油(股))、Solvesso # 100(Exxon Chemical(股))等石蠟系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷、1,2-二氯乙烷等鹵化脂肪族烴系溶劑;氯苯等鹵化含芳香環烴系溶劑;卡必醇系溶劑、苯胺、三乙胺、吡啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸、水等,該等溶劑可使用1種或作為2種以上之混合溶劑使用。該等中,酮類、醚酯系溶劑等、尤其是丙二醇-1-單甲醚-2-乙酸酯、環己酮等因於感光性組合物中抗蝕劑與光聚合起始劑之相溶性良好,故而較佳。 Examples of the organic solvent include solvents which can be usually dissolved or dispersed as needed, such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, and methyl group. Ketones such as isobutyl ketone, cyclohexanone, and 2-heptanone; diethyl ether, An ether solvent such as an alkane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, n-propyl acetate, acetic acid Ester ester, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, ester solvent such as TEXANOL; cellulose solvent such as ethylene glycol monomethyl ether or ethylene glycol monoethyl ether; methanol Alcohol solvent such as ethanol, iso- or n-propanol, iso- or n-butanol or pentanol; ethylene glycol monoacetate, ethylene glycol monoacetate, propylene glycol-1-monomethyl ether-2-acetic acid An ester ester solvent such as ester (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate or ethoxyethyl propionate; BTX solvent such as benzene, toluene or xylene; hexane, An aliphatic hydrocarbon solvent such as heptane, octane or cyclohexane; a terpene hydrocarbon oil such as turpentine, D-limonene or decene; mineral spirits, Swazol #310 (Cosmosone oil (share)), Solvesso # Paraffinic solvent such as 100 (Exxon Chemical); halogenated aliphatic hydrocarbon solvent such as carbon tetrachloride, chloroform, trichloroethylene, dichloromethane, 1,2-dichloroethane; halogenated chlorobenzene Aromatic cyclic hydrocarbon solvent; carbitol solvent, aniline, triethylamine, pyridine, acetic acid, acetonitrile, carbon disulfide, N,N-dimethylformamide, N,N-dimethylacetamide, N- Methylpyrrolidone, dimethyl hydrazine, water, and the like may be used alone or as a mixed solvent of two or more kinds. Among these, ketones, ether ester solvents, etc., especially propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, etc., are used in the photosensitive composition in the resist and the photopolymerization initiator. It is preferred because it has good compatibility.
於本發明之著色感光性組合物中,可進而添加著色劑,作為該著色劑,可列舉:染料或顏料。 A coloring agent may be further added to the coloring photosensitive composition of the present invention, and examples of the coloring agent include a dye or a pigment.
作為上述染料,只要為於380~1200nm具有吸收之化合物,則無特別限定,例如可列舉:偶氮化合物、蒽醌化合物、靛藍類化合物、三芳基甲烷化合物、二苯并吡喃化合物、茜素化合物、吖啶化合物、茋化合物、噻唑化合物、萘酚化合物、喹啉化合物、硝基化合物、吲達胺化合物、化合物、酞菁化合物、花青化合物、二亞銨化合物、氰基乙烯基化合物、二氰基苯乙烯化合物、玫瑰紅化合物、苝化合物、多烯萘內醯胺化合物、香豆素化合物、方酸鎓化合物、克酮鎓化合物、螺吡喃化合物、螺化合物、部花青化合物、氧喏化 合物、苯乙烯基化合物、吡喃鎓化合物、繞丹寧化合物、唑啉酮化合物、鄰苯二甲醯亞胺化合物、啉化合物、萘醌化合物、氮雜蒽醌化合物、卟啉化合物、氮雜卟啉化合物、吡咯亞甲基化合物、喹吖啶酮化合物、二酮基吡咯并吡咯化合物、靛藍化合物、吖啶化合物、吖化合物、甲亞胺化合物、苯胺化合物、喹吖啶酮化合物、喹酞酮化合物、醌亞胺化合物、銥錯合物化合物、銪錯合物化合物等染料等,該等亦可混合複數種使用。 The dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm, and examples thereof include an azo compound, an anthraquinone compound, an indigo compound, a triarylmethane compound, a dibenzopyran compound, and a halogen. a compound, an acridine compound, an anthraquinone compound, a thiazole compound, a naphthol compound, a quinoline compound, a nitro compound, an indamine compound, a compound, a phthalocyanine compound, a cyanine compound, a diimmonium compound, a cyanovinyl compound, a dicyanostyrene compound, a rose red compound, an anthraquinone compound, a polyenolamine compound, a coumarin compound, a squaric acid Bismuth compound, ketone oxime compound, spiropyran compound, snail a compound, a merocyanine compound, an oxonium compound, a styryl compound, a pyrylium compound, a rhodanine compound, Oxazolinone compound, phthalimide compound, a porphyrin compound, a naphthoquinone compound, an azaindole compound, a porphyrin compound, an azaporphyrin compound, a pyrrolemethylene compound, a quinacridone compound, a diketopyrrolopyrrole compound, an indigo compound, an acridine compound,吖 A dye such as a compound, a methylimine compound, an aniline compound, a quinacridone compound, a quinophthalone compound, a quinone imine compound, a ruthenium complex compound, or a ruthenium complex compound may be used in combination.
作為上述顏料,可使用無機顏料或有機顏料,例如可使用亞硝基化合物、硝基化合物、偶氮化合物、二偶氮化合物、二苯并吡喃化合物、喹啉化合物、蒽醌化合物、香豆素化合物、酞菁化合物、異吲哚啉酮化合物、異吲哚啉化合物、喹吖啶酮化合物、蒽締蒽酮化合物、芘化合物、苝化合物、二酮基吡咯并吡咯化合物、硫靛藍化合物、二化合物、三苯甲烷化合物、喹酞酮化合物、萘四羧酸;偶氮染料、花青染料之金屬錯合物化合物;色澱顏料;藉由爐法、導槽法、加熱法而獲得之碳黑、或者乙炔黑、科琴黑或燈黑等碳黑;利用環氧樹脂對上述碳黑進行調整、被覆而成者、事先於溶劑中利用樹脂對上述碳黑進行分散處理而吸附有20~200mg/g之樹脂者、對上述碳黑進行酸性或鹼性表面處理者、平均粒徑為8nm以上且DBP吸油量為90ml/100g以下者、自950℃下之揮發分中之CO、CO2算出之總氧量每碳黑之表面積100m2為9mg以上者;石墨、石墨化碳黑、活性碳、碳纖維、奈米碳管、螺旋碳纖維、碳奈米角、碳氣凝膠、富勒烯;苯胺黑、顏料黑7、鈦黑;疏水性樹脂、氧化鉻緑、米洛麗藍、鈷綠、鈷藍、錳系、亞鐵氰化物、磷酸鹽群青、鐵藍、群青、天藍、濃綠色、翡翠綠、硫酸鉛、黃丹、鋅黃、鐵丹(紅色氧化鐵(III))、鎘紅、合成鐵黑、棕土等無機顏料或有機顏料。該等顏料可單獨使用,或者混合複數種使用。 As the above pigment, an inorganic pigment or an organic pigment can be used, and for example, a nitroso compound, a nitro compound, an azo compound, a diazo compound, a dibenzopyran compound, a quinoline compound, an anthraquinone compound, or a couma bean can be used. Compound, phthalocyanine compound, isoindolinone compound, isoporphyrin compound, quinacridone compound, indolinone compound, anthraquinone compound, anthraquinone compound, diketopyrrolopyrrole compound, thioindigo compound, two Compound, triphenylmethane compound, quinophthalone compound, naphthalenetetracarboxylic acid; azo dye, metal complex compound of cyanine dye; lake pigment; carbon black obtained by furnace method, channel method, heating method Or carbon black such as acetylene black, ketjen black or lamp black; the carbon black is adjusted and coated with an epoxy resin, and the carbon black is dispersed in a solvent in advance to adsorb 20 to 200 mg of the carbon black. /g of the resin, the carbon black is subjected to an acidic or alkaline surface treatment, the average particle diameter is 8 nm or more, and the DBP oil absorption is 90 ml/100 g or less, and the CO and CO 2 in the volatile matter at 950 ° C are calculated. The total oxygen content per surface area of 100 m 2 of carbon black is 9 mg or more; graphite, graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, spiral carbon fiber, carbon nanohorn, carbon aerogel, fullerene; Aniline black, pigment black 7, titanium black; hydrophobic resin, chrome oxide green, milorie blue, cobalt green, cobalt blue, manganese, ferrocyanide, phosphate green, iron blue, ultramarine blue, sky blue, dark green , emerald green, lead sulfate, yellow dan, zinc yellow, iron dan (red Iron (III)), cadmium red, synthetic iron black, umber inorganic or organic pigment. These pigments may be used singly or in combination of plural kinds.
作為上述無機顏料或有機顏料,亦可使用市售之顏料,例如可列舉:顏料紅1、2、3、9、10、14、17、22、23、31、38、41、48、49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、228、240、254;顏料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、71;顏料黃1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180、185;顏料綠7、10、36;顏料藍15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;顏料紫1、19、23、27、29、30、32、37、40、50等。 As the above inorganic pigment or organic pigment, commercially available pigments can also be used, and examples thereof include pigment red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49. 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; pigment yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; Pigment green 7, 10, 36; pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50, and the like.
於本發明之著色感光性組合物中,上述著色劑之含量於本發明之著色感光性組合物中較佳為0~99質量%,尤佳為0~80質量%。 In the coloring photosensitive composition of the present invention, the content of the coloring agent is preferably from 0 to 99% by mass, particularly preferably from 0 to 80% by mass, based on the coloring photosensitive composition of the present invention.
於本發明之著色感光性組合物中,可進而含有無機化合物。作為該無機化合物,例如可列舉:氧化鎳、氧化鐵、氧化銥、氧化鈦、氧化鋅、氧化鎂、氧化鈣、氧化鉀、二氧化矽、氧化鋁等金屬氧化物;層狀黏土礦物、米洛麗藍、碳酸鈣、碳酸鎂、鈷系、錳系、玻璃粉末、雲母、滑石、高嶺土、亞鐵氰化物、各種金屬硫酸鹽、硫化物、硒化物、矽酸鋁、矽酸鈣、氫氧化鋁、鉑、金、銀、銅等。 The colored photosensitive composition of the present invention may further contain an inorganic compound. Examples of the inorganic compound include metal oxides such as nickel oxide, iron oxide, cerium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, cerium oxide, and aluminum oxide; layered clay minerals and rice. Lolita Blue, calcium carbonate, magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum citrate, calcium citrate, hydrogen Alumina, platinum, gold, silver, copper, etc.
於上述著色感光性組合物中使用顏料及/或無機化合物之情形時,可添加分散劑。作為該分散劑,只要為可使顏料、無機化合物分散、穩定者,則可任意,可使用市售之分散劑,例如BYK-Chemie公司製造之BYK系列等,可較佳地使用包含具有鹼性官能基之聚酯、聚醚、聚胺基甲酸酯之高分子分散劑、具有作為鹼性官能基之氮原子且 具有氮原子之官能基為胺、及/或其四級鹽,並且胺值為1~100mgKOH/g者。 When a pigment and/or an inorganic compound is used for the coloring photosensitive composition, a dispersing agent may be added. As the dispersing agent, a pigment or an inorganic compound may be dispersed or stabilized, and a commercially available dispersing agent such as BYK series manufactured by BYK-Chemie Co., Ltd. may be used, and it is preferable to use an alkaline agent. a functional group of a polyester, a polyether, a polymeric dispersant of a polyurethane, having a nitrogen atom as a basic functional group The functional group having a nitrogen atom is an amine, and/or a quaternary salt thereof, and the amine value is from 1 to 100 mgKOH/g.
於本發明之著色感光性組合物中,可視需要而添加對苯甲醚、對苯二酚、鄰苯二酚、第三丁基兒茶酚、啡噻嗪等熱聚合抑制劑;塑化劑;接著促進劑;填充劑;消泡劑;調平劑;表面調整劑;酚系抗氧化劑、亞磷酸酯系抗氧化劑、硫醚系抗氧化劑等抗氧化劑;紫外線吸收劑;分散助劑;抗凝集劑;觸媒;效果促進劑;交聯劑;增黏劑等慣用之添加物。 In the coloring photosensitive composition of the present invention, a thermal polymerization inhibitor such as p-anisole, hydroquinone, catechol, t-butyl catechol, and phenothiazine may be added as needed; plasticizer Adhesive; filler; defoamer; leveling agent; surface conditioner; phenolic antioxidant, phosphite antioxidant, thioether antioxidant, etc.; ultraviolet absorber; Agglomerating agent; catalyst; effect promoter; crosslinking agent; tackifier and other conventional additives.
又,藉由與上述具有酸值之具有乙烯性不飽和鍵之聚合性化合物一起使用其他有機聚合物,而亦可改善本發明之著色感光性組合物之硬化物之特性。作為上述有機聚合物,例如可列舉:聚苯乙烯、聚甲基丙烯酸甲酯、甲基丙烯酸甲酯-丙烯酸乙酯共聚物、聚(甲基)丙烯酸、苯乙烯-(甲基)丙烯酸共聚物、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、乙烯-氯乙烯共聚物、乙烯-乙烯系共聚物、聚氯乙烯樹脂、ABS樹脂、尼龍6、尼龍66、尼龍12、胺基甲酸酯樹脂、聚碳酸酯聚乙烯丁醛、纖維素酯、聚丙烯醯胺、飽和聚酯、酚樹脂、苯氧基樹脂、聚醯胺醯亞胺樹脂、聚醯胺酸樹脂、環氧樹脂等,該等中,較佳為聚苯乙烯、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、環氧樹脂。 Further, by using another organic polymer together with the above polymerizable compound having an ethylenically unsaturated bond having an acid value, the properties of the cured product of the colored photosensitive composition of the present invention can be improved. Examples of the above organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly(meth)acrylic acid, and styrene-(meth)acrylic acid copolymer. , (meth)acrylic acid-methyl methacrylate copolymer, ethylene-vinyl chloride copolymer, ethylene-ethylene copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane Ester resin, polycarbonate polyvinyl butyral, cellulose ester, polypropylene decylamine, saturated polyester, phenol resin, phenoxy resin, polyamidamine resin, polyamine resin, epoxy resin, etc. Among these, polystyrene, (meth)acrylic acid-methyl methacrylate copolymer, and epoxy resin are preferable.
於本發明之著色感光性組合物中,可進而併用熱自由基聚合起始劑、鏈轉移劑、增感劑、界面活性劑、矽烷偶合劑、三聚氰胺化合物等。 In the coloring photosensitive composition of the present invention, a thermal radical polymerization initiator, a chain transfer agent, a sensitizer, a surfactant, a decane coupling agent, a melamine compound or the like can be used in combination.
作為上述熱自由基聚合起始劑,可列舉:2,2'-偶氮雙異丁腈、2,2'-偶氮雙(甲基異丁酸酯)、2,2'-偶氮雙-2,4-二甲基戊腈、1,1'-偶氮雙(1-乙醯氧基-1-苯乙烷)等偶氮系起始劑;過氧化苯甲醯、過氧化苯甲醯二-第三丁基、過氧化特戊酸第三丁酯、過氧化二碳酸二(4-第三丁基環己基)酯等過氧化物系起始劑、過硫酸銨、過硫酸鈉、過硫酸 鉀等過硫酸鹽等。該等可使用一種或混合兩種以上使用。 Examples of the above thermal radical polymerization initiator include 2,2'-azobisisobutyronitrile, 2,2'-azobis(methylisobutyrate), and 2,2'-azobis. -2,4-dimethylvaleronitrile, 1,1'-azobis(1-ethenyloxy-1-phenylethane) and other azo initiators; benzamidine peroxide, benzoyl peroxide Peroxic initiators such as formazan di-t-butyl, tert-butyl peroxypivalate, di(4-tert-butylcyclohexyl) peroxydicarbonate, ammonium persulfate, persulfate Sodium, persulfate Persulfate such as potassium. These may be used alone or in combination of two or more.
作為上述鏈轉移劑、增感劑,通常可使用含硫原子之化合物。例如可列舉:硫代乙醇酸、硫代蘋果酸、硫代水楊酸、2-巰基丙酸、3-巰基丙酸、3-巰基丁酸、N-(2-巰基丙醯基)甘胺酸、2-巰基菸鹼酸、3-[N-(2-巰基乙基)胺甲醯基]丙酸、3-[N-(2-巰基乙基)胺基]丙酸、N-(3-巰基丙醯基)丙胺酸、2-巰基乙磺酸、3-巰基丙磺酸、4-巰基丁磺酸、十二烷基(4-甲硫基)苯基醚、2-巰基乙醇、3-巰基-1,2-丙二醇、1-巰基-2-丙醇、3-巰基-2-丁醇、巰基苯酚、2-巰基乙基胺、2-巰基咪唑、2-巰基苯并咪唑、2-巰基-3-羥基吡啶、2-巰基苯并噻唑、巰基乙酸、三羥甲基丙烷三(3-巰基丙酸酯)、季戊四醇四(3-巰基丙酸酯)等巰基化合物、使該巰基化合物氧化而獲得之二硫化物化合物、碘乙酸、碘丙酸、2-碘乙醇、2-碘乙磺酸、3-碘丙磺酸等碘化烷基化合物、三羥甲基丙烷三(3-巰基異丁酸酯)、丁二醇雙(3-巰基異丁酸酯)、己二硫醇、癸二硫醇、1,4-二甲基巰基苯、丁二醇雙硫代丙酸酯、丁二醇雙硫代乙醇酸酯、乙二醇雙硫代乙醇酸酯、三羥甲基丙烷三硫代乙醇酸酯、丁二醇雙硫代丙酸酯、三羥甲基丙烷三硫代丙酸酯、三羥甲基丙烷三硫代乙醇酸酯、季戊四醇四硫代丙酸酯、季戊四醇四硫代乙醇酸酯、三羥基乙基三硫代丙酸酯、下述化合物No.C1、三巰基丙酸異氰尿酸三(2-羥基乙基)酯等脂肪族多官能硫醇化合物、昭和電工公司製造之Karenz MT BD1、PE1、NR1等。 As the chain transfer agent or the sensitizer, a compound containing a sulfur atom can be usually used. For example, thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N-(2-amidinopropyl)glycolamine Acid, 2-mercaptonicotinic acid, 3-[N-(2-mercaptoethyl)amine-methylhydrazine]propionic acid, 3-[N-(2-mercaptoethyl)amino]propionic acid, N-( 3-mercaptopropyl)alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl(4-methylthio)phenyl ether, 2-mercaptoethanol , 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, nonylphenol, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole a mercapto compound such as 2-mercapto-3-hydroxypyridine, 2-mercaptobenzothiazole, thioglycolic acid, trimethylolpropane tris(3-mercaptopropionate) or pentaerythritol tetrakis(3-mercaptopropionate), The disulfide compound obtained by oxidizing the mercapto compound, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid, etc., alkyl iodide compound, trimethylolpropane tri (3-mercaptoisobutyrate), butanediol bis(3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4-dimethylnonylbenzene Butanediol dithiopropionate, butanediol dithioglycolate, ethylene glycol dithioglycolate, trimethylolpropane trithioglycolate, butanediol dithiopropionic acid Ester, trimethylolpropane trithiopropionate, trimethylolpropane trithioglycolate, pentaerythritol tetrathiopropionate, pentaerythritol tetrathioglycolate, trihydroxyethyl trithiopropane An acid ester, an aliphatic polyfunctional thiol compound such as the following compound No. C1, tris-propionic acid isocyanuric acid tris(2-hydroxyethyl) ester, Karenz MT BD1, PE1, NR1 manufactured by Showa Denko Co., Ltd., and the like.
[化30]
作為上述界面活性劑,可使用全氟烷基磷酸酯、全氟烷基羧酸鹽等氟界面活性劑、高級脂肪酸鹼鹽、烷基磺酸鹽、烷基硫酸鹽等陰離子系界面活性劑、高級胺氫鹵酸鹽、四級胺鹽等陽離子系界面活性劑、聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨醇酐脂肪酸酯、脂肪酸單甘油酯等非離子界面活性劑、兩性界面活性劑、聚矽氧系界面活性劑等界面活性劑,該等亦可組合使用。 As the surfactant, an anionic surfactant such as a perfluoroalkyl phosphate or a perfluoroalkyl carboxylate such as a fluorosurfactant, a higher fatty acid alkali salt, an alkylsulfonate or an alkyl sulfate can be used. Nonionic interfaces such as cationic surfactants such as higher amine hydrohalides and quaternary amine salts, polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters, and fatty acid monoglycerides Surfactants such as an active agent, an amphoteric surfactant, and a polyoxonated surfactant may be used in combination.
作為上述矽烷偶合劑,例如可使用信越化學公司製造之矽烷偶合劑,其中,可較佳地使用KBE-9007、KBM-502、KBE-403等具有異氰酸酯基、甲基丙烯醯基、環氧基之矽烷偶合劑。 As the decane coupling agent, for example, a decane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. may be used. Among them, KBE-9007, KBM-502, KBE-403 and the like having an isocyanate group, a methacryl fluorenyl group, and an epoxy group can be preferably used. A decane coupling agent.
作為上述三聚氰胺化合物,可列舉:(聚)羥甲基三聚氰胺、(聚)羥甲基甘脲、(聚)羥甲基苯胍、(聚)羥甲基脲等氮化合物中之活性羥甲基(CH2OH基)之全部或一部分(至少2個)經烷基醚化之化合物。此處,作為構成烷基醚之烷基,可列舉:甲基、乙基或丁基,且相互可相同亦可不同。又,未烷基醚化之羥甲基可於一分子內自縮合,亦可於二分子間進行縮合,其結果形成低聚物成分。具體而言,可使用六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺、四甲氧基甲基甘脲、四丁氧基甲基甘脲等。該等中,較佳為六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺等經烷基醚化之三聚氰胺。 As the above melamine compound, (poly)methylol melamine, (poly)methylol glycoluril, (poly)hydroxymethylphenylhydrazine A compound in which all or a part (at least 2) of the active methylol groups (CH 2 OH groups) in the nitrogen compound such as (poly)hydroxymethyl urea are alkylated. Here, examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, and they may be the same or different from each other. Further, the methylol group which is not alkyl etherified can be self-condensed in one molecule, or can be condensed between two molecules, and as a result, an oligomer component is formed. Specifically, hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril or the like can be used. Among these, melamine which is alkyl etherified, such as hexamethoxymethyl melamine or hexabutoxymethyl melamine, is preferable.
又,作為使本發明之著色感光性組合物硬化時所使用之活性光之光源,可使用發出波長300~450nm之光者,例如可使用超高壓水 銀、水銀蒸汽電弧、碳弧、氙弧等。 Further, as the light source for the active light used for curing the colored photosensitive composition of the present invention, those emitting light having a wavelength of 300 to 450 nm can be used, for example, ultrahigh pressure water can be used. Silver, mercury steam arc, carbon arc, xenon arc, etc.
進而,就不僅謀求生產性之提高,亦謀求解像性或位置精度等之提高之方面而言,雷射直接刻寫法有用,該雷射直接刻寫法係藉由將雷射光用於曝光光源,從而不使用遮罩而根據電腦等之數位資訊而直接形成圖像,作為上述雷射光,可較佳地使用340~430nm之波長之光,亦可使用氬離子雷射、氦氖雷射、YAG雷射、及半導體雷射等發出自可見至紅外區域之光者。於使用該等雷射之情形時,可添加於自可見至紅外之區域吸收之增感色素色素。 Furthermore, laser direct writing is useful for not only improving productivity, but also improving the image quality or positional accuracy. The laser direct writing method uses laser light for an exposure light source. The image is directly formed from the digital information such as a computer without using a mask. As the laser light, light of a wavelength of 340 to 430 nm can be preferably used, and an argon ion laser, a krypton laser, or a YAG can also be used. Lasers, semiconductor lasers, etc. that emit light from the visible to the infrared region. In the case of using such lasers, it is possible to add a sensitizing pigment dye which is absorbed from the visible to the infrared region.
本發明之著色感光性組合物(或其硬化物)可用於光硬化性塗料或清漆、光硬化性接著劑、印刷基板、或彩色電視機、PC監視器、攜帶型資訊終端、數位相機等彩色顯示之液晶顯示面板中之彩色濾光片、CCD影像傳感器之彩色濾光片、電漿顯示面板用之電極材料、粉末塗層、印刷油墨、印刷版、接著劑、牙科用組合物、光造形用樹脂、凝膠塗層、電子工學用之光阻劑、電鍍阻劑、蝕刻阻劑、液狀及乾燥膜兩者、焊接阻劑、用以製造各種顯示用途用之彩色濾光片或於電漿顯示面板、電發光顯示裝置、及LCD之製造步驟中用以形成構造之抗蝕劑、用以封入電氣及電子零件之組合物、阻焊劑、磁性記錄材料、微小機械零件、光波導路、光開關、鍍敷用遮罩、蝕刻遮罩、彩色試驗系、玻璃纖維纜線塗層、網版印刷用模板、用以藉由立體光刻而製造三維物體之材料、全像術記錄用材料、圖像記錄材料、微細電子電路、脫色材料、用以圖像記錄材料之脫色材料、使用微膠囊之圖像記錄材料用之脫色材料、印刷佈線板用光阻材料、UV及可見雷射直接圖像系統用之光阻材料、印刷電路基板之逐次積層中之介電體層形成所使用之光阻材料或保護膜等各種用途,其用途並無特別限制。 The colored photosensitive composition of the present invention (or a cured product thereof) can be used for a color curable coating or varnish, a photocurable adhesive, a printed substrate, or a color television, a PC monitor, a portable information terminal, a digital camera, or the like. Color filter in liquid crystal display panel, color filter of CCD image sensor, electrode material for plasma display panel, powder coating, printing ink, printing plate, adhesive, dental composition, light shaping Resins, gel coats, photoresists for electro-technical applications, plating resists, etch resists, liquid and dry films, solder resists, color filters for various display applications or a resist for forming a structure, a composition for enclosing electrical and electronic parts, a solder resist, a magnetic recording material, a micro mechanical part, an optical waveguide in a manufacturing process of a plasma display panel, an electroluminescence display device, and an LCD Road, optical switch, plating mask, etching mask, color test system, fiberglass cable coating, screen printing template, material for manufacturing three-dimensional object by stereolithography, All-image recording material, image recording material, fine electronic circuit, decolorizing material, decolorizing material for image recording material, decolorizing material for image recording material using microcapsule, photoresist material for printed wiring board, There are no particular limitations on the use of a photoresist material for a UV and visible laser direct image system, or a photoresist material or a protective film used for forming a dielectric layer in a successive layer of a printed circuit board.
本發明之著色感光性組合物係為了形成彩色濾光片之像素而使用,尤其是作為用以形成液晶顯示面板等圖像顯示裝置用之顯示裝置 用彩色濾光片之感光性組合物有用。 The colored photosensitive composition of the present invention is used for forming a pixel of a color filter, particularly as a display device for forming an image display device such as a liquid crystal display panel. A photosensitive composition using a color filter is useful.
上述顯示裝置用彩色濾光片較佳為藉由如下步驟形成:(1)將上述著色感光性組合物之塗膜形成於基板上之步驟、(2)針對該塗膜,經由具有特定圖案形狀之遮罩照射活性光之步驟、(3)利用顯影液使曝光後之被膜顯影之步驟、(4)對顯影後之該被膜進行加熱之步驟。又,本發明之著色感光性組合物作為無顯影步驟之噴墨方式之著色感光性組合物亦有用。 The color filter for a display device is preferably formed by (1) a step of forming a coating film of the colored photosensitive composition on a substrate, and (2) having a specific pattern shape for the coating film. The step of irradiating the active light with the mask, (3) the step of developing the film after the exposure with the developer, and (4) the step of heating the film after the development. Further, the colored photosensitive composition of the present invention is also useful as a coloring photosensitive composition for an inkjet method without a developing step.
以下,列舉實施例等,對本發明進一步詳細地進行說明,但本發明並不限定於該等實施例等。 Hereinafter, the present invention will be described in further detail by way of examples and the like, but the invention is not limited to the examples and the like.
<步驟1>化合物4之合成 <Step 1> Synthesis of Compound 4
於上述方案中,將化合物3之1當量及吡啶2.42g進行混合,添加化合物2之2.5當量及4-二甲胺基吡啶2.42g,於冰浴下攪拌30分鐘,添加EDC鹽酸鹽(1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride,1-乙基-(3-二甲基胺基丙基)碳醯二亞胺鹽酸鹽)之4.5等量,於氮氣氛圍下,於室溫下攪拌5小時。利用乙酸乙酯/水進行油水分離後,進行水洗、乾燥,將溶劑蒸餾去除而獲得化合物4。 In the above scheme, 1 equivalent of the compound 3 and 2.42 g of the pyridine were mixed, 2.5 equivalent of the compound 2 and 2.42 g of 4-dimethylaminopyridine were added, and the mixture was stirred for 30 minutes in an ice bath, and EDC hydrochloride was added. -(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-ethyl-(3-dimethylaminopropyl)carbonium diimine hydrochloride) 4.5 equivalents, under nitrogen atmosphere at room temperature Stir under 5 hours. After separating the oil and water with ethyl acetate/water, the mixture was washed with water, dried, and the solvent was distilled off to obtain a compound 4.
<步驟2>化合物No.1之合成 <Step 2> Synthesis of Compound No. 1
將步驟1中所獲得之化合物4之1當量及吡啶2.05g進行混合,添加4-二甲胺基吡啶0.1當量並進行攪拌後,於10℃以下滴加二碳酸第三丁酯之12當量,於室溫下攪拌20小時。利用乙酸乙酯/水進行油水分離後,進行水洗、乾燥,將溶劑蒸餾去除。藉由管柱層析法(乙酸乙酯:己烷=1:1)進行精製,自甲醇進行晶析,以產率24%獲得化合物No.1。利用1H-NMR(nuclear magnetic resonance,核磁共振)、IR(infrared radiation,紅外線)確認所獲得之化合物為目標物。又,對吸收波長特性進行測定。將結果示於[表1]及[表2]。 1 equivalent of the compound 4 obtained in the step 1 and 2.05 g of pyridine were mixed, 0.1 equivalent of 4-dimethylaminopyridine was added and stirred, and then 12 equivalents of the third butyl dicarbonate were added dropwise at 10 ° C or lower. Stir at room temperature for 20 hours. After separating the oil and water with ethyl acetate/water, the mixture was washed with water, dried, and the solvent was distilled off. Purification by column chromatography (ethyl acetate:hexane = 1:1) and crystallization from methanol afforded Compound No. 1 in a yield of 24%. The obtained compound was confirmed to be a target by 1 H-NMR (nuclear magnetic resonance) or IR (infrared radiation). Further, the absorption wavelength characteristics were measured. The results are shown in [Table 1] and [Table 2].
[化31B]
<步驟1>化合物6之合成 <Step 1> Synthesis of Compound 6
於上述方案中,將化合物5之1當量及吡啶3.12g進行混合,添加4-二甲胺基吡啶0.1當量並進行攪拌後,於10℃以下滴加二氧化第三丁酯之3當量,於室溫下攪拌3小時。利用乙酸乙酯/水進行油水分離後,進行水洗、乾燥,將溶劑蒸餾去除而獲得化合物6。 In the above embodiment, 1 equivalent of the compound 5 and 3.12 g of pyridine are mixed, 0.1 equivalent of 4-dimethylaminopyridine is added and stirred, and then 3 equivalents of the third butyl dioxide are added dropwise at 10 ° C or lower. Stir at room temperature for 3 hours. After separating the oil and water with ethyl acetate/water, washing with water, drying, and distilling off the solvent to obtain a compound 6.
<步驟2>化合物No.2之合成 <Step 2> Synthesis of Compound No. 2
將化合物7之1當量及乙酸乙酯10g、水10g進行混合,添加步驟1中所獲得之化合物6之1當量並進行攪拌後,分出乙酸乙酯層並進行乾燥,進行濃縮直至理論產量之5倍。使濃縮之乙酸乙酯溶液分散於己烷,進行晶析,以產率70%獲得化合物No.2。利用1H-NMR、IR確認所獲得之化合物為目標物。又,對吸收波長特性進行測定。將結果示於[表1]及[表2]。 One equivalent of the compound 7 and 10 g of ethyl acetate and 10 g of water were mixed, and one equivalent of the compound 6 obtained in the step 1 was added and stirred, and then the ethyl acetate layer was separated, dried, and concentrated until the theoretical yield. 5 times. The concentrated ethyl acetate solution was dispersed in hexane to carry out crystallization to obtain Compound No. 2 in a yield of 70%. The compound obtained was confirmed to be a target by 1 H-NMR and IR. Further, the absorption wavelength characteristics were measured. The results are shown in [Table 1] and [Table 2].
[化31C]
<步驟1>化合物9之合成 <Step 1> Synthesis of Compound 9
於上述方案中,將化合物8之1當量、氫氧化鈉2eq.水2g、及甲苯2g進行混合,於室溫下進行攪拌。其後,於冰浴冷卻下,添加1N鹽酸水溶液2mL而製成酸性溶液,進行油水分離,而獲得包含化合物9之甲苯溶液。 In the above scheme, 1 equivalent of the compound 8, 2 eq of sodium hydroxide, 2 g of water, and 2 g of toluene were mixed and stirred at room temperature. Thereafter, 2 mL of a 1 N aqueous hydrochloric acid solution was added thereto under ice cooling to prepare an acidic solution, and oil-water separation was carried out to obtain a toluene solution containing the compound 9.
<步驟2>化合物No.3之合成 <Step 2> Synthesis of Compound No. 3
向包含步驟1中所獲得之化合物9之1當量之甲苯溶液添加氯仿4g、化合物6之1eq.並進行攪拌,進行油水分離後,分散於己烷,進行晶析,以產率80%獲得化合物No.3。利用1H-NMR、IR確認所獲得之化合物為目標物。又,對吸收波長特性進行測定。將結果示於[表1] 及[表2]。 4 g of chloroform and 1 eq of the compound 6 were added to the toluene solution containing the compound 9 obtained in the step 1 and stirred, and the mixture was stirred in oil and water, and then dispersed in hexane to carry out crystallization to obtain a compound in a yield of 80%. No. 3. The compound obtained was confirmed to be a target by 1 H-NMR and IR. Further, the absorption wavelength characteristics were measured. The results are shown in [Table 1] and [Table 2].
<步驟1>感光性組合物No.1之製備 <Step 1> Preparation of Photosensitive Composition No. 1
將作為具有酸值之具有乙烯性不飽和鍵之聚合性化合物成分之ACA Z250(Daicel-Cytec公司製造)30.3g、作為不具有酸值之具有乙烯性不飽和鍵之聚合性化合物成分之ARONIX M-450(東亞合成公司製造)11.04g、作為光自由基聚合起始劑成分之Irgacure 907(BASF公司製造)1.93g、作為溶劑之PGMEA 36.60g以及環己酮20.08g、及作為其他成分之FZ2122(Dow Corning Toray公司製造)0.01g進行混合,進行攪拌直至不溶物消失,而獲得感光性組合物No.1。 30.3 g of ACA Z250 (manufactured by Daicel-Cytec Co., Ltd.) which is a polymerizable compound component having an ethylenic unsaturated bond having an acid value, and ARONIX M which is a polymerizable compound component having an ethylenic unsaturated bond having no acid value. -450 (manufactured by Toagosei Co., Ltd.): 11.04 g, Irgacure 907 (manufactured by BASF Corporation) as a photoradical polymerization initiator, 1.93 g of PGMEA as solvent, 36.60 g of cyclohexanone, and 20.08 g of cyclohexanone, and FZ2122 as other components (manufactured by Dow Corning Toray Co., Ltd.) 0.01 g of the mixture was stirred and the insoluble matter disappeared to obtain the photosensitive composition No. 1.
<步驟2>染料液No.1~No.3之製備 <Step 2> Preparation of Dye Liquid No. 1 to No. 3
向上述中所獲得之化合物No.1~No.3之0.10g添加二甲基乙醯胺1.90g,進行攪拌並使之溶解,而分別製備染料液No.1~No.3。 To 0.10 g of the compound No. 1 to No. 3 obtained above, 1.90 g of dimethylacetamide was added, and the mixture was stirred and dissolved to prepare dye liquids No. 1 to No. 3, respectively.
<步驟3>著色感光性組合物No.1~No.3之製備 <Step 3> Preparation of Colored Photosensitive Composition No. 1 to No. 3
將步驟1中所獲得之感光性組合物No.1之5.0g與步驟2中所獲得之染料液No.1~No.3之1.0g分別進行混合,進行攪拌直至變均勻,分別獲得本發明之著色感光性組合物No.1~No.3。 5.0 g of the photosensitive composition No. 1 obtained in the step 1 and 1.0 g of the dye liquid No. 1 to No. 3 obtained in the step 2 were respectively mixed and stirred until uniform, and the present invention was obtained. Colored photosensitive compositions No. 1 to No. 3.
將實施例2之步驟2中之化合物No.1變更為下述之比較化合物No.1~No.3中之任一者,除此以外,利用與實施例2-1相同之方法,獲得比較著色感光性組合物No.1~No.3。 The compound No. 1 in the second step of the second embodiment was changed to the following comparative compound No. 1 to No. 3, and the same method as in Example 2-1 was used to obtain a comparison. Coloring photosensitive compositions No. 1 to No. 3.
[化32]
向比較著色性感光性組合物No.1~No.3添加作為抗氧化劑之下述化合物α,除此以外,利用與實施例2-1相同之方法,獲得比較著色感光性組合物No.1A~No.3A。 A comparative coloring photosensitive composition No. 1A was obtained by the same method as Example 2-1 except that the following compound α as an antioxidant was added to the comparatively colored photosensitive composition No. 1 to No. 3 ~No.3A.
於410rpm×7sec之條件下,將上述中所獲得之著色感光性組合物No.1~No.3以及比較著色感光性組合物No.1~No.3分別塗佈於玻璃基板,利用加熱板進行乾燥(90℃、90sec)。利用超高壓水銀燈,對所獲得之塗膜進行曝光(150mJ/cm2)。於230℃×30min之條件下焙燒曝光後之塗膜。對所使用之化合物之最大吸收波長(λmax)下之焙燒前(曝光後)的塗膜之吸光度與焙燒後之塗膜之吸光度進行測定,並以將焙燒前(曝光後)之塗膜之吸光度設為100時之相對強度進行評價。再者,焙燒後之塗膜之吸光度越接近100,表示耐熱性越高。又,調查焙燒前後之色差(△Eab*)。將結果示於[表3]。 The colored photosensitive compositions No. 1 to No. 3 and the comparative colored photosensitive compositions No. 1 to No. 3 obtained in the above were applied to a glass substrate at 410 rpm × 7 sec, respectively, using a hot plate. Drying (90 ° C, 90 sec) was carried out. The obtained coating film was exposed (150 mJ/cm 2 ) using an ultrahigh pressure mercury lamp. The exposed coating film was baked at 230 ° C × 30 min. The absorbance of the coating film before calcination (after exposure) and the absorbance of the coating film after calcination at the maximum absorption wavelength (λmax) of the compound to be used are measured, and the absorbance of the coating film before baking (after exposure) is measured. The relative intensity at 100 was evaluated. Further, the closer the absorbance of the coating film after baking is to 100, the higher the heat resistance. Further, the color difference (ΔE ab* ) before and after the baking was investigated. The results are shown in [Table 3].
自上述結果可明確,本發明之著色感光性組合物之耐熱性較高。 From the above results, it is clear that the colored photosensitive composition of the present invention has high heat resistance.
首先,向著色感光性組合物No.1~No.3添加比較化合物No.1,除此以外,利用與實施例2-1相同之方法,分別獲得著色感光性組合物No.1A~No.3A。 First, the coloring photosensitive composition No. 1A to No. 1 was obtained by the same method as that of Example 2-1 except that Comparative Compound No. 1 was added to the colored photosensitive compositions No. 1 to No. 3. 3A.
將上述中所獲得之著色感光性組合物No.1A~No.3A以及比較例 2-1~2-3中所獲得之比較著色感光性組合物No.1A~No.3A於410rpm×7sec之條件下分別塗佈於玻璃基板,利用加熱板進行乾燥(90℃、90sec)。利用超高壓水銀燈對所獲得之塗膜進行曝光(150mJ/cm2)。 The comparative coloring photosensitive compositions No. 1A to No. 3A obtained in the coloring photosensitive compositions No. 1A to No. 3A obtained in the above and Comparative Examples 2-1 to 2-3 were at 410 rpm × 7 sec. Each was applied to a glass substrate under the conditions, and dried by a hot plate (90 ° C, 90 sec). The obtained coating film was exposed (150 mJ/cm 2 ) using an ultrahigh pressure mercury lamp.
於230℃×30min之條件下焙燒曝光後之塗膜。對所使用之化合物之最大吸收波長(λmax)下之焙燒前(曝光後)的塗膜之吸光度與焙燒後之塗膜之吸光度進行測定,並以將焙燒前(曝光後)之塗膜之吸光度設為100時之相對強度進行評價。又,調查焙燒前後之色差(△Eab*)。將結果示於[表4]。 The exposed coating film was baked at 230 ° C × 30 min. The absorbance of the coating film before calcination (after exposure) and the absorbance of the coating film after calcination at the maximum absorption wavelength (λmax) of the compound to be used are measured, and the absorbance of the coating film before baking (after exposure) is measured. The relative intensity at 100 was evaluated. Further, the color difference (ΔE ab* ) before and after the baking was investigated. The results are shown in [Table 4].
自上述結果可明確,向先前之色素添加了本發明之化合物之著色感光性組合物的耐熱性高於向先前之色素添加了抗氧化劑之比較著色感光性組合物。因此,其表示本發明之化合物具有較高之抗氧化功能。 From the above results, it is clear that the color-sensitive photosensitive composition to which the compound of the present invention is added to the previous dye has higher heat resistance than the comparatively colored photosensitive composition to which the antioxidant is added to the previous dye. Therefore, it means that the compound of the present invention has a high antioxidant function.
自以上之結果可明確,使用本發明之新穎化合物之著色感光性組合物及其硬化物之耐熱性較高。因此,本發明之染料及著色感光性組合物對顯示裝置用彩色濾光片及使用其而成之液晶顯示面板有用。 From the above results, it is clear that the color-sensitive photosensitive composition using the novel compound of the present invention and the cured product thereof have high heat resistance. Therefore, the dye and the coloring photosensitive composition of the present invention are useful for a color filter for a display device and a liquid crystal display panel using the same.
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