TW200839444A - Radiation sensitive composition, color filter, black matrix and liquid crystal display device - Google Patents
Radiation sensitive composition, color filter, black matrix and liquid crystal display device Download PDFInfo
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- TW200839444A TW200839444A TW096150887A TW96150887A TW200839444A TW 200839444 A TW200839444 A TW 200839444A TW 096150887 A TW096150887 A TW 096150887A TW 96150887 A TW96150887 A TW 96150887A TW 200839444 A TW200839444 A TW 200839444A
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
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- 230000001953 sensory effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
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- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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- 239000001052 yellow pigment Substances 0.000 description 1
- 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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- 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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Crystal (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
200839444 九、發明說明 【發明所屬之技術領域】 本發明有關用以形成著色層之輻射敏感性組成物,此 著色層係使用於彩色液晶顯示器、攝像管裝置及諸如此類 者,亦有關濾色器、黑基質及液晶顯示裝置。詳言之,其 有關一種用以形成著色層之輻射敏感性組成物,此組成物 可輕易製造包括塗膜物性之各種性質優異且具有優異顯影 性的著色層,有關具有自該組成物形成之著色層的濾色器 、包含自該組成物形成之著色層的黑基質及包含該濾色器 或黑基質之液晶顯示裝置。 質具 基成 黑形 或先 器預 色已 濾或 成上 形板 物基 成於 組加 性施 感物 敏成 射組. 輻m' 用感 使敏 1 當 射 術,輻 技前該 前目將 先 , [ 時 有所需圖案之遮光層的基板上,移除溶劑,使所得塗膜曝 光並顯影成所需圖案,以得到包含各個色彩之像素陣列或 係爲黑基質的著色層。所形成之著色層具有著色層在顯影 時易於基板之未曝光區域或在阻光層上具有殘留物或浮渣 、曝光區中所形成之著色層對基板或阻光層之黏著性不足 及顯影後之著色層後烘烤顯示較差之塗膜物性的缺點。 曰本專利公開申請案編號1 1 〇 5 7 7/1 9 9 5揭示一種光可 聚合組成物,其含有(1 )感光聚合起始劑,(2 )具有乙 烯型不飽和雙鍵之可加成聚合單體及(3 )鹼可溶性樹脂 ,其係藉由苯乙烯或其環經取代衍生物及順丁烯二酸酐之 -6 - 200839444 共聚物與具有一級胺基之芳烷基胺進行反應而製得’此樹 脂具有鹼溶解性且可形成耐顯影劑性質、耐鹼性、基板黏 著性及諸如此類性質優異之濾色器。然而,近年來因爲需 要可形成具有高色彩純度之濾色器及具有高遮光能力之黑 基質的輻射敏感性組成物,故變成需要增加組成物中顏料 濃度。結果,發生更容物在組成物顯影時殘留殘留物及基 板與著色層間黏著性不足的問題,期望解決此等問題。 此外,近年來在濾色器領域中,主要是藉由減低曝光 量來縮短節拍時間,加上用以形成濾色器之基板的尺寸曰 益增加,故以低曝光量形成之像素及黑基質的圖案形狀及 對基板黏著性需極優異。然而,使用習知著色輻射敏感性 組成物難以在縮節拍時間之同時得到具有良好圖案形狀之 像素及黑基質,因爲使用低曝光量條件時,圖案中易產生 缺損及側飩或圖案易因對基板黏著性不足而自基板脫落。 目前已知並沒有任一,種輻射敏感性組成物可形成具有 高色彩純度之濾色器及具有高遮光能力之黑基質而不產生 前述問題。 【發明內容】 本發明係基於前述情況所構思。本發明之目的係提供 一種用以形成顯示優異顯影性之著色層的輻射敏感性組成 物’詳言之,一種用以形成著色層之新穎輻射敏感性組成 物,其即使於低曝光量下亦不會有圖案邊緣缺損或側蝕, 可在顯影時形成精細圖案而不會在圖案邊緣具有未溶解材 200839444 料及浮渣,且可形成具有高色彩純度之濾色器及具有高遮 光能力之黑基質。 本發明另一目的係提供一種具有自前述輻射敏感性組 成物形成之著色層及自前述輻射敏感性組成物形成之黑基 質的濾色器及包含該濾色器或黑基質之液晶顯示裝置。 由以下描述可明瞭本發明其他目的及優點。200839444 IX. INSTRUCTIONS OF THE INVENTION [Technical Field] The present invention relates to a radiation-sensitive composition for forming a coloring layer for use in a color liquid crystal display, a camera tube device, and the like, and also relates to a color filter, Black matrix and liquid crystal display device. In particular, it relates to a radiation-sensitive composition for forming a coloring layer which can easily produce a coloring layer which is excellent in various properties including coating film properties and has excellent developability, and has a composition from the composition. A color filter of a colored layer, a black matrix containing a coloring layer formed from the composition, and a liquid crystal display device including the color filter or the black matrix. The base of the tool is black or the pre-color of the precursor has been filtered or formed into a super-shaped plate. The group is added to the group and the sensory substance is formed into a group. The spoke m' is used to sense the sensitivity. [On the substrate with the desired pattern of the light-shielding layer, the solvent is removed, and the resulting coating film is exposed and developed into a desired pattern to obtain a coloring layer comprising a pixel array of each color or a black matrix. The coloring layer formed has a colored layer which is easy to have an unexposed area of the substrate during development or has residue or scum on the light blocking layer, and the adhesion of the colored layer formed in the exposed area to the substrate or the light blocking layer is insufficient and developed Post-color layer post-baking shows the disadvantage of poor film properties. The present patent application publication No. 1 1 〇 5 7 7/1 9 9 5 discloses a photopolymerizable composition containing (1) a photopolymerization initiator, and (2) an ethylenically unsaturated double bond. a polymerizable monomer and (3) an alkali-soluble resin which is reacted with a styrene or a cyclic substituted derivative thereof and a maleic anhydride -6 - 200839444 copolymer with an arylalkylamine having a primary amine group Further, it is produced that the resin has alkali solubility and can form a color filter excellent in developer resistance, alkali resistance, substrate adhesion, and the like. However, in recent years, it has become necessary to increase the concentration of the pigment in the composition because of the need to form a radiation-sensitive composition having a color filter having high color purity and a black matrix having high light-shielding ability. As a result, there is a problem that the residue remains in the residue during development of the composition and the adhesion between the substrate and the colored layer is insufficient, and it is desired to solve such problems. In addition, in recent years, in the field of color filters, pixels and black substrates formed with low exposure amount are mainly shortened by reducing the exposure amount, and the size of the substrate for forming a color filter is increased. The shape of the pattern and the adhesion to the substrate are extremely excellent. However, it is difficult to obtain a pixel and a black matrix having a good pattern shape while using a conventional color-sensitive radiation-sensitive composition, because when a low exposure amount condition is used, defects are easily generated in the pattern, and side defects or patterns are easily caused. The substrate has insufficient adhesion and is detached from the substrate. It is known that none of the radiation-sensitive compositions can form a color filter having high color purity and a black matrix having high light-shielding ability without causing the aforementioned problems. SUMMARY OF THE INVENTION The present invention has been conceived based on the foregoing circumstances. SUMMARY OF THE INVENTION It is an object of the present invention to provide a radiation-sensitive composition for forming a coloring layer exhibiting excellent developability. In particular, a novel radiation-sensitive composition for forming a colored layer, even at low exposure levels There will be no pattern edge defects or side etching, which can form a fine pattern during development without having undissolved material 200839444 material and scum at the edge of the pattern, and can form a color filter with high color purity and black with high light blocking ability. Matrix. Another object of the present invention is to provide a color filter having a coloring layer formed from the above radiation-sensitive composition and a black matrix formed from the radiation-sensitive composition, and a liquid crystal display device comprising the color filter or the black matrix. Other objects and advantages of the invention will be apparent from the description.
根據本發明,首先係藉由一種輻射敏感性組成物達成 前述本發明目的及優點,該組成物係包含: (A )著色劑, (B)鹼可溶性樹脂, (C )多官能性單體,及 (D)感光聚合起始劑,According to the present invention, the above objects and advantages of the present invention are first achieved by a radiation-sensitive composition comprising: (A) a colorant, (B) an alkali-soluble resin, (C) a polyfunctional monomer, And (D) a photopolymerization initiator,
其中鹼可溶性樹脂(B )具有下式(B-1 )所示之結構:The alkali-soluble resin (B) has a structure represented by the following formula (B-1):
(其中Rl、r2及R3各獨立地表示氫原子或具有1至10 個碳原子之烷基’ X係表示具有丙烯醯基或甲基丙烯醯基 、乙烯基或1_甲基乙烯基之單價有機基團,γ係表示二價 有機基團’且h係爲1至5之整數)且該組成物係用以形 成著色層。 • 8- 200839444 其次’藉由具有自前述輻射敏感性組成物形 層的濾色器或包含自前述自由基形成之著色層的 成前述本發明目的及優點。第三,藉由包含前述 黑基質之液晶顯示裝置達成前述目的及優點。 本發明中’ 「輻射」係包括可見光、紫外線 紫外線輻射、電子束及X _射線,且「著色層」 含構成濾色器之像素陣列之層或本身係爲黑基質: 此外,本發明「濾色器」包含至少一基板及 基板上具有各種顏色(著色層)之像素陣列且亦 基質、透明導電性膜、薄膜電晶體、保護膜、間 如此類者。 較佳具體實施態樣詳述 以下詳細描述本發明。 本發明輻射敏感性組成物包含(A )著色劑, 可溶性樹脂,(C )多官能性單體及(D )感光聚 (A)著色劑 本發明輻射敏感性組成物中所含之著色劑( 別限制顏色且係根據目標著色層之應用而適當地 外,其可爲有機著色劑或無機著色劑。 有機著色劑之說明例包括有機顏料及天然顏 著色劑之說明例係包括無機顏料及體質顏料。 成之著色 黑基質達 濾色器或 輻射、遠 係表7K包 :層。 形成於該 可包含黑 隔器及諸 (B )鹼 合起始劑 A)不特 選擇。此 料。無機 200839444 前述有機顏料之說明例包括在色彩索引(C.I.;染色 工作者協會(The Society of Dyers and Colourists)公布 )中歸類爲「顏料」之化合物,詳言之,爲具有以下色彩 索引(C.I.)編號之化合物: C.I·顏料黃12、C.I·顏料黃13、C.I.顏料黃14、C.I. 顏料黃17、C.I·顏料黃20、C.I·顏料黃24、C.I.顏料黃31 、(:·Ι·顏料黃55、C.I·顏料黃83、C.I.顏料黃93、C.I.顏 料黃109、C.I·顏料黃110、C.I·顏料黃138、C.I·顏料黃 139、C.I·顏料黃 150、C.I·顏料黃 153、C.I·顏料黃 154、 C.I.顏料黃166、C.I.顏料黃168及C.I·顏料黃c.i.顏料黃 180 ; C.I.顏料橙36、C.I·顏料橙43及C.I·顏料橙51 ; C.I·顏料紅9、C.I·顏料紅97、C.I·顏料紅122、C.I. 顏料紅123、C.I·顏料紅149、C.I·顏料紅176、C.I.顏料紅 177、C.I·顏料紅180、C.I·顏料紅215、C.I.顏料紅242及 C.I.顏料紅254 ; C.I·顏料紫19、C.I.顏料紫23及C.I·顏料紫29 ; C.I.顏料藍15、C.I.顏料藍15:3、C.I·顏料藍15:6 ; C.I·顏料綠7、C.I·顏料綠36及C.I·顏料綠58 ; C.I·顏料棕23及C.I.顏料棕25 ;及 C.I·顏料黑!及cj.顏料黑7。 前述無機顏料之實例係包括硫酸鉛、黃鉛、鋅黃、胭 脂(紅色氧化鐵(III ))、鎘紅、群青、鐵藍、氧化鉻綠 、鈷錄、琥珀、鈦黑、合成鐵黑及碳黑。前述體質顏料之 -10- 200839444 說明例包括氧化鈦、硫酸鋇、氧化鋅及碳酸鈣。 前述碳黑的說明實例係包括爐黑、熱碳黑及乙炔黑。 爐黑之特定實例係包括SAF、SAF-HS、ISAF、ISAF-LS、 ISAF-HS、HAF、HAF-LS、HAF-HS、MAF、FEF、FEF-HS 、SRF、SRF-LM、SRF-LS、G P F、E C F、N - 3 3 9 及 N-35 1 。熱碳黑之特定實例係包括FT及MT。(wherein R1, r2 and R3 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms' X represents a unit price having an acrylonitrile group or a methacryl group, a vinyl group or a 1-methyl group The organic group, γ represents a divalent organic group 'and h is an integer from 1 to 5) and the composition is used to form a colored layer. • 8-200839444 Next, the objects and advantages of the present invention are achieved by a color filter having a layer formed from the aforementioned radiation-sensitive composition or a coloring layer formed from the aforementioned radical. Third, the above objects and advantages are achieved by a liquid crystal display device including the aforementioned black matrix. In the present invention, "radiation" includes visible light, ultraviolet ultraviolet radiation, electron beam, and X-ray, and the "colored layer" includes a layer of a pixel array constituting the color filter or is itself a black matrix: Further, the present invention "filters" The color filter includes at least one substrate and a pixel array having various colors (colored layers) on the substrate, and is also a matrix, a transparent conductive film, a thin film transistor, a protective film, and the like. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention is described in detail below. The radiation-sensitive composition of the present invention comprises (A) a colorant, a soluble resin, (C) a polyfunctional monomer, and (D) a photosensitive poly(A) colorant. The coloring agent contained in the radiation-sensitive composition of the present invention ( The color is not limited and is appropriately selected according to the application of the target colored layer, and may be an organic colorant or an inorganic colorant. Illustrative examples of the organic colorant include organic pigments and natural pigments, including inorganic pigments and constitutions. Pigment. The colored black matrix reaches the color filter or the radiation, and the far surface is 7K package: layer. The formation of the black separator and the (B) alkali start initiator A) is not particularly selected. This material. Inorganic 200839444 The illustrative examples of the aforementioned organic pigments include compounds classified as "pigments" in the Color Index (CI; published by The Society of Dyers and Colourists), in particular, having the following color index (CI) ) Numbered compound: CI·Pigment Yellow 12, CI·Pig Yellow 13, CI Pigment Yellow 14, CI Pigment Yellow 17, CI·Pig Yellow 20, CI·Pig Yellow 24, CI Pigment Yellow 31, (:·Ι·Pigment Huang 55, CI·Pigment Yellow 83, CI Pigment Yellow 93, CI Pigment Yellow 109, CI·Pig Yellow 110, CI·Pig Yellow 138, CI·Pig Yellow 139, CI·Pig Yellow 150, CI·Pig Yellow 153, CI · Pigment Yellow 154, CI Pigment Yellow 166, CI Pigment Yellow 168 and CI·Pigment Yellow ci Pigment Yellow 180; CI Pigment Orange 36, CI·Pigment Orange 43 and CI·Pigment Orange 51; CI·Pigment Red 9, CI·Pigment Red 97, CI·Pigment Red 122, CI Pigment Red 123, CI·Pigment Red 149, CI·Pigment Red 176, CI Pigment Red 177, CI·Pigment Red 180, CI·Pigment Red 215, CI Pigment Red 242, and CI Pigment Red 254; CI·Pigment Violet 19, CI Pigment Violet 23 and CI·Pigment Violet 29; CI Material Blue 15, CI Pigment Blue 15:3, CI·Pigment Blue 15:6; CI·Pigment Green 7, CI·Pigment Green 36 and CI·Pig Green 58; CI·Pigment Brown 23 and CI Pigment Brown 25; and CI · Pigment black! and cj. Pigment black 7. Examples of the aforementioned inorganic pigments include lead sulfate, yellow lead, zinc yellow, rouge (red iron oxide (III)), cadmium red, ultramarine blue, iron blue, chromium oxide green, cobalt Recording, amber, titanium black, synthetic iron black and carbon black. The above-mentioned constitutional pigments -10- 200839444 illustrative examples include titanium oxide, barium sulfate, zinc oxide and calcium carbonate. Examples of the aforementioned carbon black include furnace black, hot carbon Black and acetylene black. Specific examples of furnace black include SAF, SAF-HS, ISAF, ISAF-LS, ISAF-HS, HAF, HAF-LS, HAF-HS, MAF, FEF, FEF-HS, SRF, SRF- LM, SRF-LS, GPF, ECF, N-3 3 9 and N-35 1. Specific examples of thermal carbon black include FT and MT.
其市售產品之說明例係包括SAF型之DIABLACK A (Mitsubishi Chemical Corporation 之產品)及 SEAST 9 (Tokai Carbon Co·,Ltd.之產品);SAF-HS 型之 DIABLACK SA (Mitsubishi Chemical Corporation 之產 品)及 SEAST 9Η ( Tokai Carbon Co·,Ltd·之產品); ISAF 型之 DIABLACK I ( Mitsubishi Chemical Corporation 之產品)及 SEAST 6 ( Tokai Carbon Co.,Illustrative examples of the commercially available products include DIABLACK A of SAF type (product of Mitsubishi Chemical Corporation) and SEAST 9 (product of Tokai Carbon Co., Ltd.); DIABLACK SA of SAF-HS type (product of Mitsubishi Chemical Corporation) And SEAST 9Η (product of Tokai Carbon Co., Ltd.); ISAF type DIABLACK I (product of Mitsubishi Chemical Corporation) and SEAST 6 (Tokai Carbon Co.,
Ltd·之產品);ISAF-LS 型之 DIABLACK LI ( Mitsubishi Chemical Corporation 之產品)及 SEAST 600 ( TokaiLtd.'s product); ISABL-LS type DIABLACK LI (product of Mitsubishi Chemical Corporation) and SEAST 600 (Tokai
Carbon Co·,Ltd·之產品);ISAF-HS 型之 DIABLACK N 2 3 4 ( Mitsubishi Chemical Corporation 之產品)及 SEAST 7HM ( Tokai Carbon Co·,L t d ·之產品);H AF 型 之 DIABLACK H ( Mitsubishi Chemical Corporation 之產 品)及 SEAST 3 ( Tokai Carbon Co·,Ltd·之產品); HAF-LS 型之 DIABLACK LH ( Mitsubishi Chemical Corporation 之產品)及 SEAST 300 ( Tokai Carbon Co.,Carbon Co·, Ltd.); ISABL-HS type DIABLACK N 2 3 4 (product of Mitsubishi Chemical Corporation) and SEAST 7HM (product of Tokai Carbon Co·, L td ·); DIABLACK H of H AF type ( Products of Mitsubishi Chemical Corporation) and SEAST 3 (products of Tokai Carbon Co., Ltd.); DIABLACK LH (product of Mitsubishi Chemical Corporation) of HAF-LS type and SEAST 300 (Tokai Carbon Co.,
Ltd·之產品);HAF-HS 型之 DIABLACK SH ( Mitsubishi Chemical Corporation 之產品)及 SEAST KH ( Tokai -11 - 200839444Ltd.'s product); HAF-HS type DIABLACK SH (product of Mitsubishi Chemical Corporation) and SEAST KH ( Tokai -11 - 200839444
Carbon Co.,Ltd.之產品);MAF 型之 DIABLACK N5 50M (Mitsubishi Chemical Corporation 之產品)及 SEAST 116 ( Tokai Carbon Co·,Ltd·之產品);FEF 型之 DIABLACK E ( Mitsubishi Chemical Corporation 之產品 )及 SEAST SO、SEAST F 及 SEAST FM ( Tokai Carbon Co·,Ltd·之產品);SRF-LM 型之 DIABLACK N760M (Product of Carbon Co., Ltd.; DIABLACK N5 50M of MAF type (product of Mitsubishi Chemical Corporation) and SEAST 116 (product of Tokai Carbon Co., Ltd.); DIABLACK E of FEF type (product of Mitsubishi Chemical Corporation) And SEAST SO, SEAST F and SEAST FM (products of Tokai Carbon Co., Ltd.); DIABLACK N760M of SRF-LM type (
Mitsubishi Chemical Corporation 之產品)及 HTC#SL ( Nippon Steel Chemical Co ·, Ltd.之產品);及 GPF 型之 DIABLACK G ( Mitsubishi Chemical Corporation 之產品 )及 SEASTV (Tokai Car bonCo.,Ltd·之產品)。 此等著色劑可視需要以聚合物修飾粒子表面而使用。 以聚合物塗覆碳黑表面之方法係揭示於例如日本專利公開 申請案編號 7 1 73 3/1 997、95625/1 997 及 1 24969/1 997 中。 前述著色劑可單獨或二或更多種摻合使用。 .使用本發明輻射敏感性組成物形成濾色器時,著色劑 (A )較佳係爲具有高顯色性及高耐熱性之著色劑,尤其 是具有高耐熱分解性之著色劑,詳言之,有機著色劑較佳 ,尤其是使用有機顏料,因爲濾色器需展現高明晰度顯色 性及耐熱性。 同時,當使用本發明輻射敏感性組成物形成黑基質時 ,較佳係使用有機顏料或碳黑作爲著色劑(.A ),因爲黑 基質需具有高度遮光能力。 本發明著色劑可視需要與分散劑或分散助劑組合使用 -12- 200839444 作爲前述分散劑,可使用各種界面活性劑,諸如陽離 子性、陰離子性、非離子性及兩性界面活性劑,或適當之 分散劑,諸如聚合物分散劑。其中以聚合物分散劑較佳。 其特定實例係包括丙烯酸共聚物、經修飾之丙烯酸共聚物 、聚胺基甲酸酯聚酯、共聚物之烷基銨鹽或磷酸鹽及陽離 子性梳狀接枝聚合物。該陽離子性梳狀接枝聚合物係爲具 有其中兩個或更多個分子之分支鏈聚合物接枝於一分子具 有複數個鹼性基團(陽離子性官能基)之主幹聚合物上的 結構之聚合物。該種聚合物之實例係包含聚伸乙基亞胺作 爲主幹聚合物部分且ε -己內酯之開環聚合物作爲分支鏈 聚合物部分的聚合物。此等分散劑中,經修飾之丙烯酸共 聚物、聚胺基甲酸酯及陽離子性梳狀接枝聚合物較佳。 該等分散劑係市售品。經修飾丙烯酸共聚物的市售產 品之說明例包括 Disperbyk-2000 及 Disperbyk-200 1 ( BYK Japan KK之產品)。聚胺基甲酸酯市售產品之說明 例係包括 Disperbyk-161、 Disperbyk-162、 Disperbyk-165 、Disperbyk-1 67、Disperbyk-1 70 及 Disperbyk-1 82 ( BYK Japan KK之產品)。陽離子性梳狀接枝聚合物之市 售產品的說明例係包括Solsperse 24000 ( Lubrizol Japan L t d ·之產品)。 此等分散劑可單獨或二或更多種摻合使用。 分散劑之用量以1 00重量份數著色劑(A )計較佳不 高於50重量份數,更佳不高於30重量份數。 前述分散助劑之說明例係包括藍色顏料衍生物及黃色 -13- 200839444 顏料衍生物。其特定實例係包括銅酞花青衍生物。 (B)鹼可溶性樹脂 本發明輻射敏感性組成物所含之鹼可溶性樹脂(B ) 具有前述式(B-1)所示之結構。 前述式(B-1)中,R1及R2較佳係爲氫原子。R3較 佳係爲氫原子或甲基,更佳爲氫原子。較佳h係爲1。 前述式(B-1)中X較佳係爲下式(X-1)所示之單價 基團: ch2=c-^-0 十 ch2·)^- (x-1) (其中R係表示氫原子或甲基,i係爲2至5之整數,且 j係爲〇至10之整數)。前述式(X-1)中,i較佳係爲2 或5,且j較佳係爲〇至4之整數。 前述式(X-1)中Y較佳係爲亞甲基、具有2至6個 碳原子之伸烷基或伸烯基(此等伸烷基或伸烯基中間可間 雜氧原子)、環己烷二基、環己烯二基或具有6至12個 碳原子之伸芳基(此伸芳基可具有羧基或酸酐基),更佳 爲亞甲基、伸乙基、1,3-伸丙基、1,2-伸乙烯基、1,2-伸丙 烯基、1,3-伸丙烯基、2,3-伸丙烯基、環己烷-1,2-二基、 4-環己烯-1,2·二基、1,2-伸苯基、聯苯·2,2’_二基或式-CH2-0-CH2-所示之二價基團。Products of Mitsubishi Chemical Corporation) and HTC#SL (products of Nippon Steel Chemical Co., Ltd.); and DIABLACK G (product of Mitsubishi Chemical Corporation) and SEASTV (product of Tokai Car bonCo., Ltd.) of GPF type. These colorants can be used to modify the surface of the particles with a polymer as desired. A method of coating a carbon black surface with a polymer is disclosed in, for example, Japanese Patent Application Laid-Open No. 7 1 73 3/1 997, 95625/1 997, and 1 24969/1 997. The foregoing colorants may be used singly or in combination of two or more. When the color filter is formed using the radiation-sensitive composition of the present invention, the colorant (A) is preferably a coloring agent having high color rendering property and high heat resistance, especially a coloring agent having high heat decomposition resistance, Organic colorants are preferred, especially organic pigments, because color filters exhibit high definition color rendering and heat resistance. Meanwhile, when a black matrix is formed using the radiation-sensitive composition of the present invention, it is preferred to use an organic pigment or carbon black as a colorant (.A) because the black matrix is required to have a high light-shielding ability. The coloring agent of the present invention may optionally be used in combination with a dispersing agent or a dispersing aid. -12-200839444 As the aforementioned dispersing agent, various surfactants such as cationic, anionic, nonionic and amphoteric surfactants may be used, or suitable A dispersant such as a polymeric dispersant. Among them, a polymer dispersant is preferred. Specific examples thereof include an acrylic copolymer, a modified acrylic copolymer, a polyurethane polyester, an alkylammonium salt of a copolymer or a phosphate, and a cationic comb-graft polymer. The cationic comb-like graft polymer is a structure having a branched polymer in which two or more molecules are grafted onto one molecule of a backbone polymer having a plurality of basic groups (cationic functional groups) The polymer. An example of such a polymer is a polymer comprising a polyethylenimine as a main polymer portion and a ring-opening polymer of ε-caprolactone as a branched polymer portion. Among these dispersants, modified acrylic copolymers, polyurethanes and cationic comb-like graft polymers are preferred. These dispersants are commercially available products. Commercial examples of modified acrylic copolymers include Disperbyk-2000 and Disperbyk-200 1 (products of BYK Japan KK). Descriptions of commercially available products of polyurethanes include Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-1 67, Disperbyk-1 70 and Disperbyk-1 82 (products of BYK Japan KK). An illustrative example of a commercially available product of a cationic comb-like graft polymer includes Solsperse 24000 (product of Lubrizol Japan L td). These dispersants may be used singly or in combination of two or more. The dispersant is preferably used in an amount of not more than 50 parts by weight, more preferably not more than 30 parts by weight, based on 100 parts by weight of the coloring agent (A). Illustrative examples of the aforementioned dispersing aids include blue pigment derivatives and yellow-13-200839444 pigment derivatives. A specific example thereof includes a copper phthalocyanine derivative. (B) Alkali-soluble resin The alkali-soluble resin (B) contained in the radiation-sensitive composition of the present invention has a structure represented by the above formula (B-1). In the above formula (B-1), R1 and R2 are preferably a hydrogen atom. R3 is preferably a hydrogen atom or a methyl group, more preferably a hydrogen atom. Preferably, h is 1. In the above formula (B-1), X is preferably a monovalent group represented by the following formula (X-1): ch2=c-^-0 ten ch2·)^- (x-1) (wherein R represents A hydrogen atom or a methyl group, i is an integer of 2 to 5, and j is an integer of 〇 to 10). In the above formula (X-1), i is preferably 2 or 5, and j is preferably an integer of 〇 to 4. In the above formula (X-1), Y is preferably a methylene group, an alkyl group having 2 to 6 carbon atoms or an alkenyl group (such an alkyl group or an alkenyl group intermediate hetero atom); a hexanediyl group, a cyclohexenediyl group or a aryl group having 6 to 12 carbon atoms (the aryl group may have a carboxyl group or an acid anhydride group), more preferably a methylene group, an ethyl group, or a 1,3-ethyl group. Propyl, 1,2-vinyl, 1,2-extenylene, 1,3-propenyl, 2,3-extenylene, cyclohexane-1,2-diyl, 4-ring Hexene-1,2.diyl, 1,2-phenylene, biphenyl-2,2'-diyl or a divalent group of the formula -CH2-0-CH2-.
本發明輻射敏感性組成物中所含之鹼可溶性樹脂(B -14- 200839444 )除了前式(B -1 )所示之結構外’較佳係另外具有至少 一個選自以下之結構:下式(B -2 )所示之結構:The alkali-soluble resin (B-14-200839444) contained in the radiation-sensitive composition of the present invention, in addition to the structure represented by the former formula (B-1), preferably has at least one structure selected from the group consisting of (B-2) structure shown:
(其中R4係表示具有6至10個碳原子之芳基或具有3至 10個碳原子之脂環族基團),及 下式(B-3 )所示之結構:(wherein R4 represents an aryl group having 6 to 10 carbon atoms or an alicyclic group having 3 to 10 carbon atoms), and a structure represented by the following formula (B-3):
基甲基或羧基) 作爲前式(B-2)中R4之具有6至10個碳原子的芳 基之說明例係包括苯基、鄰-羥基苯基、間-羥基苯基、對-羥基苯基、鄰-甲苯基、間-甲苯基、對-甲苯基、鄰-甲氧 苯基、間-甲氧苯基、對-甲氧苯基及萘基。作爲前式(B-2 )中R4之具有3至1 〇個碳原子的脂環族基團之說明例係 包括環己基。作爲前式(B_2 )中R4,以苯基較佳。 作爲前式(B-3 )中R5至RiQ之鹵原子的說明例係包 括氯原子、溴原子及碘原子。以氯原子較佳。 -15- 200839444 前式(B-3)中,較佳係所有R5至R1G皆爲氫原子或 R7爲氯原子、羥基或羥基甲基,而所有R5、R6及R8至 R1G皆爲氫原子,更佳係所有R5至R1G皆爲氫原子或R7 爲羥基,而所有R5、R6及R8至R1G皆爲氫原子。 本發明輻射敏感性組成物所含之鹼可溶性樹脂(B ) 中,前式(B -1 )所示之結構以驗可溶性樹脂(B )之總量 計較佳係爲5至8 0重量%,更佳係爲1 0至6 0重量°/〇。當 式(Β-1)所示之結構於鹼可溶性樹脂(Β)中之含量介於 前述範圍內時,含有該鹼可溶性樹脂(Β )之輻射敏感性 組成物的顯影性得到改善’且對於在顯影時產生殘留物之 抑制變得更爲有效。 本發明輻射敏感性組成物中所含之鹼可溶性樹脂(Β )具有以鹼可溶性樹脂(Β )總量計較佳不高於5 0重量% ,更佳係5至4 5重量%之前式(Β - 2 )所示結構。此外’ 鹼可溶性樹脂(Β )具有具有以鹼可溶性樹脂(Β )總量計 較佳不高於60重量%,更佳係5至40重量%之前式(Β-3 )所示結構。此外,鹼可溶性樹脂(Β )可兼具有前式( Β-2 )所示結構及前式(Β·3 )所示之結構’此情況下’此 等結構之總含量較佳係以鹼可溶性樹脂(Β )總量計不高 於8 0重量%,更佳係1 〇至7 0重量%。此情況下’前式( Β - 2 )所示結構及前式(Β ·3 )所示結構之個別含量較佳係 個別介於前述範圍內。 當前式(Β-2)所示結構及前式(Β**3)所示結構於鹼 可溶性樹脂(Β )中之含量介於前述範圍內時’得到有益 -16- 200839444 地進一步改善待形成之著色層對基板之黏著性白 本發明輻射敏感性組成物中所含鹼可溶性 藉凝膠滲透層析(GPC )測量相對於聚苯乙少 2,000至100, 〇〇〇之重量平均分子量Mw,更佳 5 0,000。鹼可溶性樹脂(B)之重量平均分子: 圍內時,得到鹼可溶性樹脂於溶劑或顯影劑中 一步改善的優點。鹼可溶性樹脂(B)之重量 M w對數量平均分子量(藉Gp c測量相對於聚 比Mw/Mn較佳係1 ·〇至4.0,更佳係1.0至3 溶性樹脂(B )之Mw/Mn介於前述範圍時,得 善待製得之輻射敏感性組成物的解析度及待形 對基板之黏著性的優點。 鹼可溶性樹脂(B )可藉由例如將下式( 化合物(以下稱爲「不飽和單羧酸(a 1 )」: X—COOH (a1 ) 勺優點。 樹脂(B ) 希具有較佳 爲3,0 0 0至 量介於此範 之溶解度進 平均分子量 苯乙烯)之 ί.ο。當鹼可 到進一步改 成之著色層 al )所示之Illustrative examples of the aryl group having 6 to 10 carbon atoms as R4 in the above formula (B-2) include a phenyl group, an o-hydroxyphenyl group, a m-hydroxyphenyl group, a p-hydroxy group. Phenyl, o-tolyl, m-tolyl, p-tolyl, o-methoxyphenyl, m-methoxyphenyl, p-methoxyphenyl and naphthyl. An illustrative example of an alicyclic group having 3 to 1 carbon atoms of R4 in the above formula (B-2) includes a cyclohexyl group. As R4 in the above formula (B_2), a phenyl group is preferred. The illustrative examples of the halogen atom of R5 to RiQ in the above formula (B-3) include a chlorine atom, a bromine atom and an iodine atom. It is preferred to use a chlorine atom. -15- 200839444 In the above formula (B-3), preferably all of R5 to R1G are a hydrogen atom or R7 is a chlorine atom, a hydroxyl group or a hydroxymethyl group, and all of R5, R6 and R8 to R1G are a hydrogen atom. More preferably, all of R5 to R1G are hydrogen atoms or R7 is a hydroxyl group, and all of R5, R6 and R8 to R1G are hydrogen atoms. In the alkali-soluble resin (B) contained in the radiation-sensitive composition of the present invention, the structure represented by the former formula (B-1) is preferably from 5 to 80% by weight based on the total amount of the soluble resin (B). More preferably, it is from 10 to 60 weights / 〇. When the content of the structure represented by the formula (Β-1) in the alkali-soluble resin (Β) is within the above range, the developability of the radiation-sensitive composition containing the alkali-soluble resin (Β) is improved' The suppression of residue generated during development becomes more effective. The alkali-soluble resin (Β) contained in the radiation-sensitive composition of the present invention has preferably not more than 50% by weight, more preferably 5 to 45% by weight, based on the total amount of the alkali-soluble resin (Β). - 2) The structure shown. Further, the alkali-soluble resin (Β) has a structure represented by the formula (Β-3) which is preferably not more than 60% by weight, more preferably 5 to 40% by weight based on the total of the alkali-soluble resin (Β). Further, the alkali-soluble resin (Β) may have both a structure represented by the former formula (Β-2) and a structure represented by the former formula (Β·3). In this case, the total content of such structures is preferably a base. The total amount of the soluble resin (Β) is not more than 80% by weight, more preferably 1% to 70% by weight. In this case, the individual contents of the structure represented by the former formula ((-2) and the structure of the former formula (Β3) are preferably within the above range. When the content of the structure represented by the present formula (Β-2) and the structure represented by the former formula (Β**3) in the alkali-soluble resin (Β) is within the above range, it is further improved to be formed by the benefit of -16-394444. Adhesion of the color layer to the substrate The alkali solubility contained in the radiation-sensitive composition of the present invention is measured by gel permeation chromatography (GPC) with respect to polystyrene of 2,000 to 100, and the weight average molecular weight of ruthenium Mw, better 50,000. The weight average molecular weight of the alkali-soluble resin (B): When it is enclosed, the advantage that the alkali-soluble resin is improved in one step in a solvent or a developer is obtained. The weight Mw of the alkali-soluble resin (B) is a number average molecular weight (measured by Gp c with respect to the poly ratio Mw/Mn, preferably from 1 to 4.0 to 4.0, more preferably from 1.0 to 3, Mw/Mn of the soluble resin (B)) In the above range, the resolution of the radiation-sensitive composition to be prepared and the adhesiveness to be formed on the substrate are obtained. The alkali-soluble resin (B) can be, for example, a compound (hereinafter referred to as " Unsaturated monocarboxylic acid (a 1 )": the advantage of X-COOH (a1). The resin (B) preferably has a solubility of 3,0 0 to an amount corresponding to the average molecular weight of styrene. ο. When the base can be further changed into the color layer a)
(其中X係如同前式(B-1)所定義) 下稱爲「苯 添加於具有下式(Β-Γ )所示結構之樹脂(以 乙烯環氧樹脂」):(where X is as defined in the former formula (B-1)) is referred to as "benzene added to a resin having the structure shown by the following formula (Β-Γ) (with ethylene epoxy resin):
(其中R1、R2、R3及h係如同前式(B-1 )所 -17- 義), 200839444 較佳係具有由前式(B-Ρ)所示之結構及至少一個選自由 前式(B-2 )所示之結構及由前式(B_3 )所示之結構所構 成之基團的樹脂,之後將由下式(a2 )所示之化合物(以 下稱爲「多元酸酐(a2)」): 0 I!(wherein R1, R2, R3 and h are as defined in the above formula (B-1) -17-), and 200839444 preferably has a structure represented by the former formula (B-Ρ) and at least one selected from the former formula ( a resin represented by the structure represented by B-2) and a group represented by the structure represented by the above formula (B_3), and then a compound represented by the following formula (a2) (hereinafter referred to as "polybasic acid anhydride (a2)") : 0 I!
A \/〇 (a2)A \/〇 (a2)
CC
IIII
0 (其中γ係如同前式(B-1)所定義) 添加於不飽和單羧酸(a 1 )與苯乙烯環氧樹脂(B ·1 f)之 反應產物中而製得。 前述苯乙烯環氧樹脂較佳係爲下式(b 1 )所示之化合 物(以下稱爲「化合物(b 1 )」):0 (wherein γ is as defined in the above formula (B-1)) is added to a reaction product of an unsaturated monocarboxylic acid (a 1 ) and a styrene epoxy resin (B·1 f). The styrene epoxy resin is preferably a compound represented by the following formula (b 1 ) (hereinafter referred to as "compound (b 1 )"):
(其中R1、R2、R3及h係如同前式(B-1 )所定義) 的聚合物,或爲化合物(b 1 )與其他自由基可聚合之化合 物的共聚物。 化合物(b 1 )之特定實例係包括鄰-乙烯基苄基縮水 甘油基醚、間-乙烯基苄基縮水甘油基醚、對-乙烯基苄基 縮水甘油基醚、α -甲基-鄰-乙烯基苄基縮水甘油基醚、 -18- 200839444 α -甲基-間-乙稀基节基縮水甘油基醚、α -甲基-對-乙火希 基苄基縮水甘油基醚、2,3-二縮水甘油氧基甲基苯乙烯、 2,4-二縮水甘油氧基甲基苯乙烯、2,5-二縮水甘油氧基甲 基苯乙烯、2,6-二縮水甘油氧基甲基苯乙烯、2,3,4-三縮水 甘油氧基甲基苯乙烯'2,3,5-三縮水甘油氧基甲基苯乙烯 、2,3,6-三縮水甘油氧基甲基苯乙嫌、2,4,5 -三縮水甘油氧 基甲基苯乙烯及2,4,6-三縮水甘油氧基甲基苯乙烯。其中 ,鄰-乙烯基苄基縮水甘油基醚、間-乙烯基苄基縮水甘油 基醚、對-乙烯基苄基縮水甘油基醚較佳。此等化合物可 二或更多種組合使用。 前述其他自由基可聚合之化合物的說明例係包括下式 (b2)所示之化合物(以下稱爲「化合物(b2)」):(a polymer in which R1, R2, R3 and h are as defined in the above formula (B-1)) or a copolymer of the compound (b1) and another radical polymerizable compound. Specific examples of the compound (b 1 ) include o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o- Vinylbenzyl glycidyl ether, -18- 200839444 α-methyl-m-ethyl benzyl glycidyl ether, α-methyl-p-ethylsulfonyl benzyl glycidyl ether, 2, 3-diglycidoxymethylstyrene, 2,4-diglycidoxymethylstyrene, 2,5-diglycidoxymethylstyrene, 2,6-diglycidyloxy Styrene, 2,3,4-triglycidoxymethylstyrene '2,3,5-triglycidoxymethylstyrene, 2,3,6-triglycidoxymethylbenzene B, 2,4,5-triglycidoxymethylstyrene and 2,4,6-triglycidoxymethylstyrene. Among them, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p-vinylbenzyl glycidyl ether are preferred. These compounds may be used in combination of two or more. The above-mentioned other examples of the radical polymerizable compound include a compound represented by the following formula (b2) (hereinafter referred to as "compound (b2)"):
(其中R4係如同前式(B-2 )所定義), 下式(b3 )所示之化合物(以下稱爲「化合物(b3 )」)(wherein R4 is as defined in the above formula (B-2)), a compound represented by the following formula (b3) (hereinafter referred to as "compound (b3)")
(其中R5至rig如同前式(B-3 )所定義), -19- 200839444 及除化合物(b 1 ) 、( b2 )及(b3 )以外之自由基可聚合 之化合物(以下稱爲「化合物(b 4 )」)。 前述化合物(b2 )將前式(B-2 )所示之結構導入鹼 _ 可溶性樹脂(B )內。化合物(b2 )之特定實例係包括N- 苯基順丁烯二醯亞胺、N -鄰-羥基苯基順丁烯二醯亞胺、 N -間-經基苯基順丁嫌二醯亞胺、N ·對-經基苯基順丁燒二 醯亞胺、N-鄰-甲基苯基順丁烯二醯亞胺、N-間-甲基苯基 馨順丁烯二醯亞胺、N -對-甲基苯基順丁嫌二醯亞胺、N _鄰-甲氧基苯基順丁烯二醯亞胺、N -間-甲氧基苯基順丁嫌二 醯亞胺、N -對-甲氧基苯基順丁燦二醯亞胺及N —環己基順 丁烯二醯亞胺。其中,N-苯基順丁烯二醯亞胺較佳。 前述化合物(b3)將前式(B-3)所示之結構導入驗 可溶性樹脂(B )內。化合物(.b3 )之特定實例係包括苊 、5 -氯危、5 -經基甲基危及5 -經基危。其中危及5 -經基苊 較佳。 • 前述化合物(b4 )之說明例包括芳族乙儲基化合物, 諸如本乙嫌、α-甲基苯乙嫌、鄰-乙嫌基甲苯、間-乙嫌基 甲苯、對-乙烯基甲苯、對-氯苯乙燒、鄰-甲氧基苯乙矯、 ^ 間·甲氧基苯乙烯、對-甲氧基苯乙烯、茚及對_乙燃基节基 甲基醚;不飽和羧酸酯,諸如丙烯酸甲酯、甲基丙嫌酸甲 醋、丙細酸乙醋、甲基丙矯酸乙醋、丙燦酸正丙酯、甲基 丙烯酸正丙酯、丙烯酸異丙酯、甲基丙烯酸異丙酯、丙燒 酸正丁酯、甲基丙烯酸正丁酯、丙烯酸異丁酯、甲基丙燦 酸異丁酯、丙烯酸第二丁酯、甲基丙烯酸第二丁酯、丙燃 -20- 200839444 酸第三丁酯、甲基丙烯酸第三丁酯、丙烯酸2-羥基乙酯、 甲基丙烯酸2-羥基乙酯、丙烯酸2-羥基丙酯、甲基丙烯酸 2- 羥基丙酯、丙烯酸3-羥基丙酯、甲基丙烯酸3-羥基丙酯 、丙烯酸2-羥基丁酯、甲基丙烯酸2-羥基丁酯、丙烯酸 3- 羥基丁酯、甲基丙烯酸3-羥基丁酯、丙烯酸4-羥基丁酯 、甲基丙烯酸4-羥基丁酯、丙烯酸烯丙酯、甲基丙烯酸烯 丙酯、丙烯酸苄酯、甲基丙烯酸苄酯、丙烯酸苯酯、甲基 丙烯酸苯酯、甲氧基三乙二醇丙烯酸酯、甲氧基三乙二醇 甲基丙烯酸酯及甘油單甲基丙烯酸酯;不飽和羧酸胺基烷 基酯,諸如丙烯酸2-胺基乙酯、甲基丙烯酸2-胺基乙酯、 丙烯酸2-胺基丙酯、甲基丙烯酸2-胺基丙酯、丙烯酸3-胺基丙酯及甲基丙烯酸3-胺基丙酯;羧酸乙烯酯,諸如乙 酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯及苯甲酸乙烯酯;不 飽和醚,諸如乙烯基甲基醚、乙烯基乙基醚、烯丙基縮水 甘油醚及甲基烯丙基縮水甘油醚;乙烯基氰化合物,諸如 丙烯腈、甲基丙烯腈、α-氯丙烯腈及亞乙烯基二氰;不 飽和醯胺,諸如丙烯醯胺、甲基丙燒醯胺、α -氯丙燒酿 胺、Ν -經基乙基丙烯醯胺及Ν -經基乙基甲基丙烯醯胺; 脂族共軛二烯,諸如1,3-丁二烯、異戊間二烯及氯丁二烯 ;及聚合物分子鏈末端具有單丙烯醯基或單甲基丙烯醯基 之巨單體,諸如聚苯乙烯、聚丙烯酸甲酯、聚甲基丙烯酸 甲酯、聚丙烯酸正丁酯、聚甲基丙烯酸正丁酯及聚矽酮烷 此等化合物(b4 )可單獨或二或更多種摻合使用 -21 - 200839444 當苯乙烯環氧樹脂係爲化合物(bl)與其他自由基可 聚合化合物之共聚物時,就鹼可溶性樹脂(B )之合成簡 易性而言,化合物(b 1 )與待共聚之其他自由基可聚合化 合物的比例可根據鹼可溶性樹脂(B )中所需之前式(B -1 )所示結構、前式(B-2 )所示結構及前式(B-3 )所示結 構的比例適當地設定。 例如,待共聚之化合物(b 1 )的比例較佳係爲5至8 0 重量%,更佳係爲1 〇至80重量%。當待共聚之化合物( bl )的比例高於80重量%時,易於下文所述之不單羧基( al )加成反應中發生膠凝化,某些情況下可能難以製得鹼 可溶性樹脂(B )。同時,當待共聚之化合物(b 1 )的比 例低於5重量%時,自苯乙烯環氧樹脂、不飽和單羧酸( al )及多元酸酐(a2 )之加成反應形成的樹脂之鹼溶解度 無法令人滿意,故當使用含有該樹脂之輻射敏感性組成物 形成著色層時,可能於基板之未曝光區域或於遮光層上產 生殘留物或浮渣。 待共聚之化合物(b2 )的比例較佳不高於5 0重量%, 更佳係5至45重量%。待共聚之化合物(b3 )的比例較佳 不高於60重量%,更佳係5至40重量%。化合物(b2 ) 及(b3 )可一起使用於共聚,此情況下,其可於化合物( b2 )及(b3 )之總量較佳不大於80重量%之量下共聚,更 佳係5至70重量%。化合物(b2 )及(b3 )在組合使用時 ,其量較佳係介於前述個別範圍內。 苯乙烯環氧樹脂特佳係以下化合物之共聚物: -22- 200839444 (1 )化合物(b 1 ) ’ (2 )化合物(b2 )及(b3 )中至少一種,及 (3 )化合物(b4 )。此情況下’化合物(b 1 )於共聚物 中之量較佳係爲1〇至60重量%,化合物(b2)及(b;3) 中至少一種於共聚物中之量(或當組合使用時係爲化合物 (b 2 )及(b 3 )之總量)較佳係爲5至60重量%,而化合 物(b4 )於共聚物中之量較佳係不高於5 0重量%。 苯乙烯環氧樹脂之重量平均分子量Mw及重量平均分 子量對數量平均分子量之比例Mw/Mn可根據鹼可溶性樹 脂(B )所需之Mw及Mw/Mn而適當地設定。 前述苯乙烯環氧樹脂可藉著使前述化合物或前述化合 物之混合物於適當之溶劑在適當之自由基聚合起始劑存在 下進行聚合而製得。作爲可使用於製造苯乙烯環氧樹脂之 溶劑,可使用例如與下文所述作爲本發明輻射敏感性組成 物所使用溶劑相同的溶劑。自由基聚合起始劑的說明例係 包括2,2’-偶氮基異丁腈、2,2’·偶氮基雙(2,4·二甲基戊腈 )及2,2’-偶氮基雙(4 -甲氧基- 2,4 -二甲基戊腈)。 前述不飽和殘酸(al)可根據前式(B-i)中所需之 X類型而適當地選擇。不飽和羧酸(al )之較佳實例係包 括丙烯酸、甲基丙烯酸、羧基_聚己內酯單丙儲酸酯、 ω·羧基-聚己內酯單甲基丙烯酸酯、2-丙烯醯氧乙基琥珀 酸及2-甲基丙烯醯氧乙基琥珀酸。前述ω -羧基-聚己內酯 單丙稀酸酯及ω-竣基-聚己內酯單甲基丙嫌酸酯中,聚己 內酯之重現單元數目較佳係爲丨至10,更佳爲2至4。前 -23- 200839444 述不飽和羧酸(al)中,丙烯酸及甲基丙烯酸特佳,因爲 其係高反應性。此等化合物可單獨或二或更多種摻合使用 〇 不飽和單羧酸(al )對前述苯乙烯環氧樹脂之加成反 應可根據已知方法進行。例如,加成反應可較佳地於溶劑 及酯化觸媒存在下,於5 0至1 5 0 °C溫度進行6至2 4小時 。可作爲溶劑之溶劑的說明例包括丙二醇單甲基醚乙酸酯 、乙二醇單甲基醚乙酸酯、丙二醇單甲基醚乙酸酯、丙二 醇單乙基醚乙酸酯、雙乙二醇二甲基醚、雙乙二醇甲基乙 基醚、環己酮、2-庚酮、3-庚酮、2-羥基丙酸乙酯、3 -甲 氧基丙酸乙酯、3 -乙氧基丙酸甲酯、3 -乙氧基丙酸乙酯、 丙酸3-甲基-3-甲氧基丁酯、乙酸正丁酯、乙酸異丁酯、 甲酸正戊酯、乙酸異戊酯、丙酸正丁酯、丁酸乙酯、丁酸 異丙酯、丁酸正丁酯及丙酮酸乙酯。 作爲酯化觸媒,可使用例如三級胺,諸如三乙基胺、 三甲基胺、苄基甲基胺及苄基二乙基胺;及四級銨鹽,諸 如氯化四甲基銨、氯化四乙基銨、氯化苄基三乙基銨、氯 化十二碳基三甲基銨及溴化四丁基銨。若需要,則可使用 聚合抑制劑,諸如對-甲氧基酚或甲基氫醌。酯化觸媒用 量以苯乙烯環氧樹脂中所含之環氧基計較佳不大於〇·5當 量,更佳爲0.0 1至0.1當量。聚合抑制劑用量以反應溶液 總量計較佳不大於5,0 0 0 ppm,更佳係5 0 0至3,0 0 0 ppm。 不飽和單羧酸(al )之用量較佳係苯乙烯環氧樹脂中 每當量環氧基有0·7至1.3當量,更佳係〇·9至1.2當量 -24 - 200839444 前述多元酸酐(a2 )可根據前式(Β·1 )中所需 類型而適當地選擇。多元酸酐(a2)之較佳實例係包 二酸酐、順丁烯二酸酐、檸康酸酐、琥珀酸酐、戊二 、戊烯二酸酐、衣康酸酐、二甘醇酸酐、苯二甲酸酐 己酮-1,2-二甲酸酐、4-環己烯-1,2-二甲酸酐及聯苯酸 其中,琥珀酸酐、戊二酸酐、苯二甲酸酐及4_環己烯 二甲酸酐特佳,因其係高反應性。 多元酸酐(a2 )對苯乙烯環氧樹脂之加成反應可 同前述不飽和單羧酸(al)對苯乙烯環氧樹脂之加成 的條件下進行。亦可在不飽和單羧酸(a 1 )對苯乙烯 樹脂之加成反應之後,將多元酸酐(a2)添加於反應 物中,並持續加成反應。 多元酸酐(a2)用量較佳苯乙燃環氧樹脂中每當 氧基有0.2至1.0當量,更佳係〇·4至〇·9當量。 本發明輻射敏感性組成物含有以1 0 0重量份數著 (Α)計較佳爲10至200重量份數之量的前述鹼可溶 脂(Β),更佳爲2 0至1 5 0重量份數。當此値小於 量份數時,可能因爲敏感性不足而使待形成之著色層 度不足,而當其大於20G重量份數時,所得到之濾色 色彩純度或所得到之黑基質的遮光能力可能不足° (C)多官能性單體 本發明輻射敏感性組成物中多官能性單體(C ) 之Y 括丙 酸酐 、環 酐。 -1,2- 在如 反應 環氧 混合 量環 色劑 性樹 10重 的硬 器的 之說 -25- 200839444 明例包括烷二醇,諸如乙二醇及丙二醇之二丙烯酸酯 甲基丙烯酸酯;聚烷二醇,諸如聚乙二醇及聚丙二醇 丙烯酸酯或二甲基丙烯酸酯;具有三或更多個官能基 羥基醇諸如甘油、三羥甲基丙烷、異戊四醇及二異戊 的多丙烯酸酯或多甲基丙烯酸酯;具有三或更多個官 之經二羧酸修飾的多羥基醇之多丙烯酸酯或多甲基丙 酯;聚酯、環氧樹脂、胺基甲酸酯樹脂、醇酸樹脂、 酮樹脂、螺烷樹脂及諸如此類者之寡丙烯酸酯或寡甲 烯酸酯;兩末端皆羥基化之聚合物諸如兩末端皆羥基 聚丁二烯、兩末端皆羥基化之聚異戊間二烯及兩末端 基化之聚己內酯的二丙烯酸酯或二甲基丙烯酸酯;及 三-丙烯醯氧基乙酯及磷酸三-甲基丙烯醯氧基乙基酯。 前述多官能性單體中,「具有三或更多個官能基 二羧酸修飾的多羥基醇之多丙烯酸酯或多甲基丙烯酸 係表示自將一個二羧酸加成於具有三或更多個官能基 羥基醇所形成的單酯化合物之多丙烯酸酯或多甲基丙 酯。 此等多官能性單體中,具有三或更多個官能基之 基醇之多丙烯酸酯或多甲基丙烯酸酯及具有三或更多 能基之經二羧酸修飾的多羥基醇之多丙烯酸酯或多甲 烯酸酯較佳。其特定實例包括三羥甲基丙烷三丙烯酸 三羥甲基丙烷三甲基丙烯酸酯、異戊四醇三丙烯酸酯 戊四醇三甲基丙烯酸酯、經琥珀酸修飾之異戊四醇三 酸酯、經琥珀酸修飾之異戊四醇三甲基丙烯酸酯、異 或二 之二 之多 四醇 能基 烯酸 聚矽 基丙 化之 皆羥 磷酸 之經 酯」 之多 烯酸 多羥 個官 基丙 酯、 、異 丙烯 戊四 -26- 200839444 醇四丙烯酸酯、異戊四醇四甲基丙烯酸酯、二異戊四醇六 丙烯酸酯及二異戊四醇六甲基丙烯酸酯。前述化合物中, 經琥珀酸修飾之異戊四醇三丙烯酸酯及經琥珀酸修飾之異 戊四醇三甲基丙烯酸酯係下式所示之化合物:(wherein R5 to rig are as defined in the above formula (B-3)), -19- 200839444 and a radical polymerizable compound other than the compounds (b 1 ), (b2) and (b3) (hereinafter referred to as "compounds" (b 4 )"). The compound (b2) described above introduces the structure represented by the above formula (B-2) into the alkali-soluble resin (B). Specific examples of the compound (b2) include N-phenyl maleimide, N-o-hydroxyphenyl maleimide, N-meta-phenyl-phenyl-butane Amine, N · p-paraphenyl cis-butadiene diimide, N-o-methylphenyl maleimide, N-m-methylphenyl succinimide , N-p-methylphenyl cis-butane diimine, N-o-methoxyphenyl maleimide, N-m-methoxyphenyl cis-butane diimine , N-p-methoxyphenyl cis-butyl bis-imide and N-cyclohexyl maleimide. Among them, N-phenyl maleimide is preferred. The above compound (b3) is introduced into the test soluble resin (B) by the structure represented by the above formula (B-3). Specific examples of the compound (.b3) include hydrazine, 5-chloro-risk, 5-aminomethyl-containing methyl group and 5-amino group. It is preferable to endanger the 5 - basis. • An illustrative example of the aforementioned compound (b4) includes an aromatic ethyl storage compound such as the present invention, α-methylphenylethyl, o-ethyl-toluene, m-ethyl-toluene, p-vinyltoluene, p-Chlorobenzopyrene, o-methoxyphenethyl, ^-methoxystyrene, p-methoxystyrene, hydrazine and p-ethane hydroxy benzyl methyl ether; unsaturated carboxylic acid Ester, such as methyl acrylate, methyl propyl methacrylate, ethyl acetoacetate, methyl propyl acetonate, n-propyl propyl acrylate, n-propyl methacrylate, isopropyl acrylate, methyl Isopropyl acrylate, n-butyl propyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, second butyl acrylate, second butyl methacrylate, propionate - 20- 200839444 Tert-butyl acid ester, tert-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, acrylic acid 3-hydroxypropyl ester, 3-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxy acrylate Butyl ester, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, Phenyl acrylate, phenyl methacrylate, methoxy triethylene glycol acrylate, methoxy triethylene glycol methacrylate and glycerol monomethacrylate; unsaturated carboxylic acid aminoalkyl ester, such as 2-Aminoethyl acrylate, 2-Aminoethyl methacrylate, 2-Aminopropyl acrylate, 2-Aminopropyl methacrylate, 3-Aminopropyl acrylate and 3-amine methacrylate Propyl acrylate; vinyl acetate such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, allyl shrinkage Glycidyl ether and methallyl glycidyl ether; vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile and vinylidene cyanide; unsaturated decylamines such as acrylamide, methyl Propylene amide, α-chloropropanol, hydrazine-ylethyl acrylamide and hydrazine - phenylethyl methacrylamide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; and polymer molecular chain ends having a mono propylene group or Monomethicone-based macromonomers such as polystyrene, polymethyl acrylate, polymethyl methacrylate, polybutyl acrylate, polybutyl methacrylate, and polyfluorenone. B4) may be used alone or in combination of two or more. -200839444 When a styrene epoxy resin is a copolymer of a compound (bl) and another radical polymerizable compound, the synthesis of the alkali-soluble resin (B) In terms of simplicity, the ratio of the compound (b 1 ) to the other radical polymerizable compound to be copolymerized may be according to the structure of the formula (B-1) required in the alkali-soluble resin (B), and the former formula (B-2) The ratio of the structure shown and the structure shown in the former formula (B-3) is appropriately set. For example, the proportion of the compound (b 1 ) to be copolymerized is preferably from 5 to 80% by weight, more preferably from 1 to 80% by weight. When the proportion of the compound ( bl ) to be copolymerized is more than 80% by weight, it is easy to gel in a non-monocarboxy ( al ) addition reaction described below, and in some cases, it may be difficult to obtain an alkali-soluble resin (B). . Meanwhile, when the ratio of the compound (b 1 ) to be copolymerized is less than 5% by weight, a base of a resin formed by an addition reaction of a styrene epoxy resin, an unsaturated monocarboxylic acid (al ), and a polybasic acid anhydride (a2 ) Solubility is unsatisfactory, so when a colored layer is formed using a radiation-sensitive composition containing the resin, residue or scum may be generated on the unexposed or exposed portion of the substrate. The proportion of the compound (b2) to be copolymerized is preferably not more than 50% by weight, more preferably 5 to 45% by weight. The proportion of the compound (b3) to be copolymerized is preferably not more than 60% by weight, more preferably 5 to 40% by weight. The compounds (b2) and (b3) may be used together for copolymerization, in which case they may be copolymerized in an amount of preferably not more than 80% by weight based on the total amount of the compounds (b2) and (b3), more preferably 5 to 70. weight%. When the compounds (b2) and (b3) are used in combination, the amount thereof is preferably within the aforementioned individual ranges. A styrene epoxy resin is preferably a copolymer of the following compounds: -22- 200839444 (1) Compound (b 1 ) ' (2) at least one of compounds (b2) and (b3), and (3) compound (b4) . In this case, the amount of the compound (b 1 ) in the copolymer is preferably from 1 to 60% by weight, and the amount of at least one of the compounds (b2) and (b; 3) in the copolymer (or when used in combination) The amount of the compound (b 2 ) and (b 3 ) is preferably from 5 to 60% by weight, and the amount of the compound (b4) in the copolymer is preferably not more than 50% by weight. The weight average molecular weight Mw of the styrene epoxy resin and the ratio of the weight average molecular weight to the number average molecular weight Mw/Mn can be appropriately set depending on the Mw and Mw/Mn required for the alkali-soluble resin (B). The styrene epoxy resin can be obtained by polymerizing a mixture of the above compound or the above compound in a suitable solvent in the presence of a suitable radical polymerization initiator. As the solvent which can be used for the production of the styrene epoxy resin, for example, the same solvent as that used hereinafter as the radiation-sensitive composition of the present invention can be used. Illustrative examples of the radical polymerization initiator include 2,2'-azoisobutyronitrile, 2,2'-azobis(2,4.dimethylpentanenitrile), and 2,2'-couple. Nitrogen bis(4-methoxy-2,4-dimethylvaleronitrile). The aforementioned unsaturated residual acid (al) can be appropriately selected depending on the type of X required in the above formula (B-i). Preferred examples of the unsaturated carboxylic acid (al) include acrylic acid, methacrylic acid, carboxy-polycaprolactone monopropionate, ω·carboxy-polycaprolactone monomethacrylate, 2-propene oxime Ethyl succinic acid and 2-methylpropenyl oxyethyl succinic acid. In the aforementioned ω-carboxy-polycaprolactone monoacrylic acid ester and ω-mercapto-polycaprolactone monomethyl propyl acrylate, the number of reproducing units of polycaprolactone is preferably from 10 to 10, More preferably 2 to 4. -23-200839444 Among the unsaturated carboxylic acids (al), acrylic acid and methacrylic acid are particularly preferred because of their high reactivity. These compounds may be used singly or in combination of two or more. The addition reaction of the unsaturated monocarboxylic acid (al) with the aforementioned styrene epoxy resin can be carried out according to a known method. For example, the addition reaction may preferably be carried out at a temperature of from 50 to 150 ° C for 6 to 24 hours in the presence of a solvent and an esterification catalyst. Illustrative examples of the solvent which can be used as a solvent include propylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and diethylene glycol. Alcohol dimethyl ether, bisethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, ethyl 2-hydroxypropionate, ethyl 3-methoxypropionate, 3- Methyl ethoxypropionate, ethyl 3-ethoxypropionate, 3-methyl-3-methoxybutyl propionate, n-butyl acetate, isobutyl acetate, n-amyl formate, acetic acid Amyl ester, n-butyl propionate, ethyl butyrate, isopropyl butyrate, n-butyl butyrate and ethyl pyruvate. As the esterification catalyst, for example, tertiary amines such as triethylamine, trimethylamine, benzylmethylamine and benzyldiethylamine; and quaternary ammonium salts such as tetramethylammonium chloride can be used. , tetraethylammonium chloride, benzyltriethylammonium chloride, dodecyltrimethylammonium chloride and tetrabutylammonium bromide. If necessary, a polymerization inhibitor such as p-methoxyphenol or methylhydroquinone can be used. The amount of the esterification catalyst is preferably not more than 〇·5 equivalent, more preferably 0.01 to 0.1 equivalent, based on the epoxy group contained in the styrene epoxy resin. The polymerization inhibitor is preferably used in an amount of not more than 5,000 ppm, more preferably from 50,000 to 3,000 ppm, based on the total amount of the reaction solution. The amount of the unsaturated monocarboxylic acid (al ) is preferably from 0.7 to 1.3 equivalents per equivalent of the epoxy group in the styrene epoxy resin, more preferably from 9 to 1.2 equivalents from 24 to 200839444. ) It can be appropriately selected according to the type required in the former formula (Β·1). Preferred examples of the polybasic acid anhydride (a2) are dianhydride, maleic anhydride, citraconic anhydride, succinic anhydride, pentane, glutaconic anhydride, itaconic anhydride, diglycolic anhydride, phthalic anhydride ketone -1,2-Dicarboxylic anhydride, 4-cyclohexene-1,2-dicarboxylic anhydride and biphenyl acid, of which succinic anhydride, glutaric anhydride, phthalic anhydride and 4-cyclohexene dicarboxylic anhydride are particularly preferred. Because of its high reactivity. The addition reaction of the polybasic acid anhydride (a2) to the styrene epoxy resin can be carried out under the conditions of addition of the above unsaturated monocarboxylic acid (al) to styrene epoxy resin. Further, after the addition reaction of the unsaturated monocarboxylic acid (a 1 ) to the styrene resin, the polybasic acid anhydride (a2) may be added to the reactant and the addition reaction may be continued. The amount of the polybasic acid anhydride (a2) is preferably from 0.2 to 1.0 equivalent per equivalent of the oxyethylene oxide epoxy resin, more preferably from 44 to 〇·9 equivalent. The radiation-sensitive composition of the present invention contains the aforementioned alkali-soluble fat (Β) in an amount of preferably 10 to 200 parts by weight based on 100 parts by weight, more preferably 20 to 150% by weight. Number of copies. When the enthalpy is less than the number of parts, the coloring layer to be formed may be insufficient due to insufficient sensitivity, and when it is more than 20 G parts by weight, the color purity of the obtained color filter or the shading ability of the obtained black matrix may be obtained. It may be insufficient. (C) Polyfunctional monomer The Y of the polyfunctional monomer (C) in the radiation-sensitive composition of the present invention includes propionic anhydride and cyclic anhydride. -1,2- In the case of a reaction-epoxy compounding amount of a 10-color hardener, -25-200839444 The example includes an alkanediol, such as ethylene glycol and propylene glycol diacrylate methacrylate Polyalkylene glycols such as polyethylene glycol and polypropylene glycol acrylate or dimethacrylate; having three or more functional hydroxyl alcohols such as glycerol, trimethylolpropane, pentaerythritol and diisoamyl Polyacrylate or polymethacrylate; polyacrylate or polymethyl propyl ester having three or more dicarboxylic acid modified polyhydric alcohols; polyester, epoxy resin, urethane An ester resin, an alkyd resin, a ketone resin, a spiro resin, and the like, an oligoacrylate or oligoenoate; a polymer which is hydroxylated at both ends, such as a hydroxyl terminated polybutadiene at both ends, and hydroxylated at both ends a polyisoprene or a di-capped polycaprolactone diacrylate or dimethacrylate; and a tri-acryloxyethyl ester and a tri-methyl propylene methoxyethyl phosphate . In the above polyfunctional monomer, "polyacrylate or polymethacrylic acid having three or more functional dicarboxylic acid-modified polyhydric alcohols is represented by addition of one dicarboxylic acid to have three or more a polyacrylate or polymethyl propyl ester of a monoester compound formed by a functional hydroxy alcohol. Among these polyfunctional monomers, a polyacrylate or polymethyl group having a base alcohol having three or more functional groups A polyacrylate or polymethacrylate of an acrylate and a dicarboxylic acid-modified polyhydric alcohol having three or more energy groups is preferred. Specific examples thereof include trimethylolpropane trimethylolpropane triacrylate. Methacrylate, pentaerythritol triacrylate pentaerythritol trimethacrylate, succinic acid-modified pentaerythritol triester, succinic acid-modified pentaerythritol trimethacrylate, different Or two or more of the tetradecyl olefinic acid polydecyl propylated hydroxyphosphoric acid esters of polyhydroxyl sulphate, isopropenyl pentylene -26-200839444 alcohol tetraacrylate , pentaerythritol tetramethacrylate, diisoamyl Tetraol hexaacrylate and diisopentaerythritol hexamethacrylate. Among the above compounds, succinic acid-modified isovaerythritol triacrylate and succinic acid-modified pentaerythritol trimethacrylate are compounds represented by the following formula:
(其中R係表示氫原子或甲基)。 φ 此等多官能性單體中,三羥甲基丙烷三丙烯酸酯、異 戊四醇三丙烯酸酯及二異戊四醇六丙烯酸酯特佳,因得到 ^ 具有高強度及優異之表面光滑性的著色層,且極少於形成 ^ 著色層圖案之區域以外的區域中產生浮渣及膜殘留物。 前述多官能性單體可單獨使用或二或更多種摻合使用 〇 多官能性單體(C )於本發明輻射敏感性組成物中之 用量以1 〇〇重量份數該鹼可溶性樹脂(B )計較佳係爲5 至500重量份數,更佳係爲2〇至300重量份數。當該多 -27- 200839444 官能性單體(c )之量低於5重量份數時,著色層之強度 及表面光滑性可能降低,而當該量高於500重量份數時, 對鹼顯影劑之顯影性可能不足或可能易於形成著色層圖案 之區域以外的區域中產生浮渣及膜殘留物。 本發明輻射敏感性組成物中,前述多官能性單體可部 分由單官能性單體取代。 該等單官能性單體之特定實例係包括ω -羧基·聚己內 酯單丙烯酸酯、ω-羧基-聚己內酯單甲基丙烯酸酯、甲氧 基三乙二醇丙烯酸酯、甲氧基三乙二醇甲基丙烯酸酯、甲 氧基雙丙二醇丙烯酸酯、甲氧基雙丙二醇甲基丙烯酸酯、 丙烯酸2-羥基-3-苯氧基丙酯、甲基丙烯酸2-羥基-3-苯氧 基丙酯、單琥珀酸2-丙烯醯氧乙酯及單琥珀酸2-甲基丙烯 醯氧乙酯。其市售產品之說明例包括 Μ-5 3 00 ( TOAGOSEI CO·,LTD.)。 此等單官能性單體可單獨使用或二或更多種摻合使用 〇 前述單官能性單體之量以多官能性單體及單官能性單 體之總里3十較佳係爲不大於9 0重量%,更佳係不大於5 0 重量%。 (D )感光聚合起始劑 本發明輻射敏感性組成物所含之感光聚合起始劑係爲 可藉著暴露於輻射(諸如可見光、紫外線輻射、遠紫外線 輻射、電子束或X-射線)產生自由基之化合物,此自由 -28- 200839444(wherein R represents a hydrogen atom or a methyl group). φ Among these polyfunctional monomers, trimethylolpropane triacrylate, pentaerythritol triacrylate and diisopentaerythritol hexaacrylate are particularly preferable because of high strength and excellent surface smoothness. The colored layer and the scum and film residue are generated in a region other than the region where the colored layer pattern is formed. The foregoing polyfunctional monomer may be used singly or in combination of two or more, using the fluorene-sensitive monomer (C) in the radiation-sensitive composition of the present invention in an amount of 1 part by weight based on the alkali-soluble resin ( B) is preferably from 5 to 500 parts by weight, more preferably from 2 to 300 parts by weight. When the amount of the poly--27-200839444 functional monomer (c) is less than 5 parts by weight, the strength and surface smoothness of the colored layer may be lowered, and when the amount is more than 500 parts by weight, the alkali development is performed. The developability of the agent may be insufficient or scum and film residue may be generated in a region other than the region where the pattern of the color layer may be easily formed. In the radiation-sensitive composition of the present invention, the aforementioned polyfunctional monomer may be partially substituted by a monofunctional monomer. Specific examples of such monofunctional monomers include ω-carboxy-polycaprolactone monoacrylate, ω-carboxy-polycaprolactone monomethacrylate, methoxytriethylene glycol acrylate, methoxy Triethylene glycol methacrylate, methoxybispropanediol acrylate, methoxybispropanediol methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-methacrylate Phenoxypropyl ester, 2-propenyloxyethyl monosuccinate and 2-methylpropenyloxyethyl monosuccinate. Examples of commercially available products include Μ-5 3 00 (TOAGOSEI CO·, LTD.). These monofunctional monomers may be used singly or in combination of two or more. The amount of the aforementioned monofunctional monomer is preferably not more than 30% of the total of the polyfunctional monomer and the monofunctional monomer. More than 90% by weight, more preferably no more than 50% by weight. (D) Photosensitive polymerization initiator The photopolymerization initiator contained in the radiation-sensitive composition of the present invention can be produced by exposure to radiation such as visible light, ultraviolet radiation, far ultraviolet radiation, electron beam or X-ray. Free radical compound, this freedom -28- 200839444
基可起始前述多官能性單體(C )與在某些情況下使用之 單官能性單體的聚合。作爲感光聚合起始劑,可適當地使 用肟化合物、聯咪唑化合物、安息香化合物、乙醯基苯化 合物、二苯基甲酮化合物、α -二酮化合物、多環醌化合 物、咕噸酮化合物、膦化合物、三嗪化合物、重氮化合物 、鑰鹽、醯亞胺磺酸酯化合物或諸如此類者。 前述肟化合物包括咔唑化合物及其他膀化合物。 味唑化合物之實例有下式(D_n所示之化合物:The base may initiate the polymerization of the aforementioned polyfunctional monomer (C) with the monofunctional monomer used in some cases. As the photopolymerization initiator, a ruthenium compound, a biimidazole compound, a benzoin compound, an ethoxybenzene compound, a diphenyl ketone compound, an α-diketone compound, a polycyclic guanidine compound, a xanthone compound, or the like can be suitably used. A phosphine compound, a triazine compound, a diazonium compound, a key salt, a quinone sulfinate compound or the like. The aforementioned hydrazine compounds include carbazole compounds and other bladder compounds. Examples of the oxazole compound are compounds of the formula (D_n:
(其中R係表示具有1至20個碳原子之烷基、具有3 至8個碳原子之環烷基或苯基, R12及R13各獨JLL地表不氫原子、具有〗至20個碳原 子之烷基、具有3至8個碳原子之環烷基、可經取代之苯 基或具有7至20個碳原子之單價脂環族基團(不包括前 述環院基), R14係表示具有1至12個碳原子之烷基、具有3至8 個碳原子之環烷基、具有1至12個碳原子之烷氧基或具 有3至8個碳原子之環烷氧基,當存有複數個rM時,其 -29- 200839444 可彼此相同或相異, R15係表示具有4至20個碳原子之單價含氧雜環基、 具有4至20個碳原子之單價含氮雜環基或具有4至20個 碳原子之單價含硫雜環基,當存有複數個R15時,其可、彼 此相同或相異, P係爲〇至6之整數,q係爲·〇或l,n係爲〇至5之 整數,m係爲0至5之整數,其限制條件爲(n + m ) $ 5 ) 〇 作爲式(D-1)中R11的具有1至20個碳原子之烷基 的說明例包括甲基、乙基、正丙基、異丙基、正丁基、第 二丁基、第三丁基、正戊基、正己基、正庚基、正辛基、 正壬基、正癸基、正十一碳基及正十二碳基。作爲R11的 具有3至8個碳原子之環烷基的說明例包括環戊基及環己 基。式(D-1)中R11之較佳實例係包括甲基及乙基。 作爲式(D-1)中R12及R13的具有1至20個碳原子 之烷基的說明例包括甲基、乙基、正丙基、異丙基、正丁 基、第二丁基、第三丁基、正戊基、正己基、正庚基、正 辛基、正壬基、正癸基、正十一碳基及正十二碳基。作爲 R12及R13的具有3至8個碳原子之環烷基的說明例包括 環戊基及環己基。作爲R12及R13的苯基之取代基的說明 例係包括具有1至6個碳原子之烷基,諸如甲基、乙基、 正丙基、異丙基、正丁基、第二丁基、第三丁基、正戊基 及正己基;具有3至6個碳原子之環烷基,諸如環戊基及 環己基;具有1至6個碳原子之烷氧基,諸如甲氧基、乙 -30- 200839444 氧基、正丙氧基、異丙氧基、正丁氧基及第三丁氧基;具 有3至6個碳原子之環烷氧基,諸如環戊氧基及環己氧基 ;苯基;及鹵原子,諸如氟及氯原子。作爲R12及R13的 苯基之取代基的數目較佳係〇至4個,更佳係0或1個。 此外,作爲R12及R13之具有7至20個碳原子的單價 脂環族基團(不包括前述環烷基)之說明例係包括具有1 -烷基環烷結構之基團、具有三環烷結構之基團、具有螺烷 結構之基團、具有 烯結構之基團及具有金剛烷結構之基 團。作爲式(D-1)中之R12及R13,氫原子、甲基及乙基 較佳。 作爲式(D-1 )中R14之具有1至12個碳原子的烷基 之說明例係包括甲基、乙基、正丙基、異丙基、正丁基、 第二丁基、第三丁基、正戊基、正己基、正庚基、正辛基 、正壬基、正癸基、正十一碳基及正十二碳基。作爲R14 之具有3至8個碳原子的環烷基之說明例係包括環戊基及 環己基。作爲R14之具有1至12個碳原子的烷氧基之說 明例係包括甲氧基、乙氧基、正丙氧基、異丙氧基、正丁 氧基、第三丁氧基、正戊氧基、正己氧基、正庚氧基、正 辛氧基、正壬氧基、正癸氧基、正十一碳氧基及正十二碳 氧基。作爲R14之具有3至8個碳原子的環烷氧基之說明 例係包括環戊氧基及環己氧基。作爲式(D-1)中R14,以 甲基、乙基、正丙基、異丙基、正丁基、甲氧基及乙氧基 較佳。 作爲式(D-1)中R15之具有4至20個碳原子之單價 -31 - 200839444 含氧雜環基、具有4至20個碳原子之單價含氮雜環基及 具有4至20個碳原子之單價含硫雜環基的說明例係包括 硫嗦基、氮呼基、二氫氮呼基、二氧戊環基、三曉基、氧 硫環己烷基、噻唑基、噁二嗪基、二氧雜氫茚基、二噻烷 萘基、呋喃基、噻吩基、吡咯基、噁唑基、異噁唑基、噻 唑基、異噻唑基、吡唑基、呋咱基、哌喃基、吡啶基、嗒 嗪基、嘧啶基、吡嗪基、吡咯啉基、嗎弗基(morphonyl )、哌嗪基、崐啶基、吲哚基、異吲哚基、苯并呋喃基、 苯幷噻吩基、·吲哚嗪基、色烯基、喹啉基、異喹啉基、嘌 呤基、喹唑啉基、啐啉基、酞嗪基、喋啶基、味唑基、吖 Π疋基、菲D定基、噻噸基、吩嗪基、吩噻曉基、氧硫雜蒽基 、吩噁嗪基、噻蒽基、四氫呋喃基及四氫哌喃基。作爲式 (D-1)中Ri5,二氧戊環基、四氫呋喃基及四氫哌喃基較 佳。 式(D - 1 )中之p較佳係爲〇、1或2,尤其是1。 式(D - 1 )中之n較佳係爲〇、1或2,尤其是〗,且 式(D-1 )中之m較佳係爲〇或i。 則式(D · 1 )所示之化合物中,其中q爲〇之化合物 (以下稱爲「咔唑化合物(1)」)及其中4爲1且㈤爲 1之化合物(以下稱爲「咔唑化合物(2 )」)較佳。 前述咔唑化合物(1 )之特定實例係包括 卜〔%乙基·6_苯甲醯-9·η·-咔唑-3·基〕-U2-壬烷-2-肟-◦〜 苯甲酸酯, 1-〔9.乙基-6_苯甲醯_911-咔唑-3-基〕-1,2_壬烷-2_肟-〇_ -32- 200839444 乙酸酯, 1-〔9-乙基-6-苯甲醯-9.11.-昨唑-3-基〕-1,2-戊烷-2-肟-0- 乙酸酯, 1-〔9-乙基-6-苯甲醯·9·Η._咔唑-3-基〕-辛烷-1-酮肟-0-乙 酸酯, 1-〔9-乙基-6-(2-甲基苯甲醯)-9.11.-味唑-3-基〕-乙烷-1-酮肟-〇-苯甲酸酯, 1-〔9-乙基-6-(2-甲基苯甲醯)-9.11.-咔唑-3-基〕-乙烷-1-酮肟-〇-乙酸酯, 1-〔9 -正丁基-6- ( 2 -乙基苯甲醯)-9.Η. -味唑-3-基〕-乙 烷-1-酮肟-〇-苯甲酸酯, 乙酮-1-〔 9-乙基-6- ( 2-甲基-4-四氫呋喃基苯甲醯)-9·Η·-咔唑-3-基〕-1- (Ο-乙醯肟), 乙酮-1-〔 9-乙基-6- ( 2-甲基-4-四氫哌喃基苯甲醯)-9·Η·- 味唑-3-基〕-1- (Ο-乙醯肟), 乙酮-1-〔 9-乙基-6- ( 2-甲基-5-四氫呋喃基苯甲醯)-9·Η·-味唑-3-基〕-1- ( 〇-乙醯肟), 乙酮-1-〔 9-乙基-6- ( 2-甲基-5-四氫哌喃基苯甲醯)-9·Η·- 咔唑-3-基〕-1- (Ο-乙醯肟),及 乙丽-1-〔 9 -乙基-6- { 2 -甲基-4- ( 2,2 - 一·甲基-1,3 - 一*氧戊 環基)苯甲醯} -9.Η·-味唑-3-基〕-1- ( 0-乙醯肟)。 前述咔唑化合物(2 )之特定實例係包括乙酮-1 -〔 9-乙基-6- (2 -甲基-4-四氫呋喃基甲氧基苯甲醯)-9.Η.-咔 唑-3-基〕-1- ( 0-乙醯肟), -33- 200839444 乙酮-1-〔 9-乙基-6- (2_甲基-4_四氫哌喃基甲氧基苯甲醯 )-9.11.-咔唑-3-基〕-1-(0-乙醯肟), 乙酮-1-〔 9-乙基-6- (2-甲基-5-四氫呋喃基甲氧基苯甲醯 )·9·Η·-咔唑-3-基〕-1- ( 0-乙醯肟), 乙酮-1-〔 9-乙基-6- (2-甲基-5_四氫哌喃基甲氧基苯甲醯 )-9·Η·-咔唑-3-基〕-1-(0-乙醯肟),及 乙酮-1-〔 9-乙基-6- { 2-甲基-4- (2,2-二甲基-1,3-二氧戊 環基)甲氧基苯甲醯} -9·Η·-咔唑-3-基〕-1-(0-乙醯肟) 〇 其中,在咔唑化合物(1)中之1-〔 9-乙基- 6-(2-甲 基苯甲醯)味唑-3-基〕-乙烷-1-酮肟-0-乙酸酯及在 味H坐化合物(2)中之乙酬-1-〔 9 -乙基-6- ( 2 -甲基-4-四氨 呋喃基甲氧基苯甲醯)咔唑-3-基〕-1- ( 0-乙醯肟) 及乙丽-1-〔 9 -乙基-6- { 2 -甲基-4- ( 2,2 - _^甲基-1,3 - 一^氧 戊環基)甲氧基苯甲醯} 咔唑-3-基〕-1-(0-乙醯肟 )較佳。特佳係咔唑化合物(2 )中之乙酮-1-〔 9-乙基-6-{ 2-甲基-4- ( 2,2-二甲基-1,3-二氧戊環基)甲氧基苯甲醯 } -9.H·-咔唑-3-基〕-1- ( 0-乙醯肟)。 前述其他肟化合物之說明例係包括 1,2 -羊—嗣-1-〔4-(苯硫基)本基〕-2·(0 -本甲酸基胎) 1,2-丁二酮-1-〔 4-(苯硫基)苯基〕-2- ( 0-苯甲醯基肟) 1,2-丁二酮-1-〔 4-(苯硫基)苯基〕-2- ( 0-乙醯基肟), -34- 200839444 1,2·辛二酮-1-〔 4-(甲硫基)苯基〕-2- ( 0-苯甲醯基肟) ,及 1,2 -辛二嗣-1-〔 4-(苯硫基)苯基〕-2- (0-(4 -甲基苯甲 醯基肟))。其中,1,2-辛二酮-1-〔 4-(苯硫基)苯基〕-2- ( 〇-苯甲醯基肟)特佳。 前述聯咪唑化合物之說明例係包括 2,2’-雙(2·氯苯基)-4,4’,5,5’-四(4-乙氧基羰基苯基)-1,2、聯咪唑, 2,2’-雙(2-溴苯基)-4,4、5,5’-四(4乙氧基羰基苯基)-1,2’-聯咪唑, 2,2’-雙(2-氯苯基)-4,4f,5,5’-四苯基-1,2’-聯咪唑, 2,2’-雙(2,4-二氯苯基)-4,4’,5,5’-四苯基-1,2’-聯咪唑, 2,2’-雙(2,4,6-三氯苯基)-4,4’,5,5’-四苯基-1,2’-聯咪唑, 2,2’-雙(2-溴苯基)-4,4’,5,5’-四苯基-1,2·聯咪唑, 2,2’-雙(2,4-二溴苯基)-4,4\5,5’-四苯基-1,2’聯咪唑,及 2,2’-雙(2,4,6-三溴苯基)-4,4’,5,5’-四苯基-1,2’-聯咪唑。 當聯咪唑化合物於本發明輻射敏感性組成物中作爲感 光聚合起始劑(D)時,較佳係與氫供體組合使用,因可 進一步改善敏感性。「氫供體」係表示可提供氫原子給藉 曝光自聯咪唑化合物產生之自由基的化合物。作爲氫供體 ’硫醇化合物、胺化合物及諸如此類者較佳。 前述硫醇化合物係爲具有苯環或雜環性環及一或多個 (較佳一至三個,更佳一或兩個)直接鍵結於環之巯基的 化合物。硫醇化合物之特定實例係包括2-锍基苯并噻唑、 -35- 200839444 2 -锍基苯并噁唑、2 -锍基苯并咪唑、2,5 -二巯基-1,3,4 -噻 二唑及2-锍基-2,5-二甲基胺基吡啶。 前述胺化合物係爲具有苯環或雜環性環及一或多個( 較佳一至三個’更佳一或兩個)直接鍵結於環之胺基的化 合物。胺化合物之特定實例係包括4,4’-雙(二甲基胺基) 二苯基甲酮,4,4’-雙(二乙基胺基)二苯基甲酮,4-二乙 基胺基乙醯基苯,4-二甲基胺基丙醯基苯,4-二甲基胺基 苯甲酸乙酯,4-二甲基胺基苯甲酸異戊酯,4-二甲基胺基 苯甲酸及4-二甲基胺基苄腈。 當使用聯咪唑化合物作爲本發明輻射敏感性組成物中 感光聚合起始劑(D )時,較佳係同時使用硫醇化合物及 胺化合物兩者作爲氫供體,因爲輻射敏感性組成物之敏感 性高,所形成之著色層幾乎不會在顯影期間自基板脫落, 且著色層之強度亦高。 前述安息香化合物之說明例係包括安息香、安息香甲 基醚、安息香乙基醚、安息香異丙基醚、安息香丁基醚及 甲基2-安息香苯甲酸酯。 前述乙醯基苯化合物之說明例係包括2,2-二甲氧基乙 醯苯、2,2-二乙氧基乙醯苯、2,2-二甲氧-2-苯基基乙醯苯 、2-羥基-2-甲基-1-苯基丙-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙-1-酮、2-甲基-(4-甲硫基苯基-2-嗎啉-1-丙-1-酮、4- ( 2-羥基乙氧基)苯基-2-(羥基-2_丙基)酮 、2-苄基-2-二甲基胺基-1- ( 4-嗎啉苯基)丁 -1-酮、1-羥 基環己基苯基酮及2,2-二甲氧基-1,2-二苯基乙-1-酮。 -36- 200839444 甲 酮 苯 醌 及 基 膦 化 雙 ) 基 嗪 甲 - S - 量 前述二苯基甲酮化合物之說明例係包括4,4’-雙(二 基胺基)二苯基甲酮及4,4’-雙(二乙基胺基)二苯基甲 〇 前述α -二酮化合物之說明例係包括二乙醯基、二 甲醯基及苯甲醯基甲酸甲酯。 前述多環醌化合物之說明例係包括蒽醌、2-乙基蒽 、2-第三丁基蒽醌及1,4_萘醌。 前述咕噸酮化合物之說明例係包括咕噸酮、噻噸酮 2 -氯咕噸酮。 前述膦化合物之說明例係包括氧化雙(2,4,6-三甲 苯甲醯基)苯基膦及氧化2,4,6 -三甲基苯甲醯基二苯基 〇 前述三嗪化合物之說明例係包括具有鹵甲基之三嗪 合物,諸如2,4,6-三(三氯甲基)-s-三嗪、2-甲基-4,6-(三氯甲基)-s-三嗪、2-〔 2·(呋喃-2-基)乙烯基〕 4,6·雙(三氯甲基)-s-三嗪、2-〔 2- ( 5 -甲基呋喃-2-基 乙烯基〕-4,6 -雙(三氯甲基)-s-三嗪、2-〔 2-(4 -二乙 胺基-2 -甲基苯基)乙烯基〕-4,6 -雙(三氯甲基)-s -三 、2-〔2-(3,4-二甲氧基苯基)乙烯基〕_4,6-雙(三氯 基)-s-三嗪、2- (4_甲氧基苯基)-4,6-雙(三氯甲基) 三嗪、2-(4-乙氧基苯乙烯基)_4,6-雙(三氯甲基)-S· 嗪及2-(4-正丁氧基苯基)_4,6-雙(三氯甲基)-s三嗪 此等感光聚合起始劑可單獨或二或更多種摻合使用 本發明中,該感光聚合起始劑(D)之量以1〇〇重 -37- 200839444 份數之多官能性單體(C )單官能性單體之總量計較佳係 爲0.01至500重量份數,更佳1至300重量份數,尤其 是10至200重量份數。當該感光聚合起始劑(D )之量低 於0.0 1重量份數時,藉由曝光進行之固化不足,可能變 成難以得到具有根據既定配置排列之著色層圖案的圖案陣 列,而當該量高於5 00重量份數時,所形成之染色層易在 顯影期間自基板脫落,且易形成浮渣並易在基板未曝光區 域或在遮光層上殘留膜殘留物。 本發明輻射敏感性組成物所含之感光聚合起始劑(D )較佳係含有肟化合物,更佳係含有前式(D-1 )所示之 化合物。當感光聚合起始劑(D )含有肟化合物及其他感 光聚合起始劑時,與該肟化合物組合使用之其他感光聚合 起始劑較佳係爲聯咪唑化合物、乙醯基苯化合物、三嗪化 合物、安息香化合物、二苯基甲酮化合物、α -二酮化合 物、多環醌化合物、咕噸酮化合物、重氮化合物、鑰鹽及 醯亞胺磺酸酯化合物,而乙醯基苯化合物特佳。 本發明中,肟化合物用量以感光聚合起始劑(D )之 總量計較佳係至少2 0重量%,更佳至少5 0重量%。 其他添加劑 除了前述著色劑(A )、鹼可溶性樹脂(Β )、多官能 性單體(C )及感光聚合起始劑(D )之外,本發明輻射敏 感性組成物可視需要含有各種其他添加劑。 該等其他添加劑之說明例係包括塡充劑、界面活性劑 38· 200839444 、黏著促進劑、抗氧化劑、紫外線吸收劑、凝結抑制劑及 顯影性調節劑。 前述塡充劑之特定實例係包括玻璃及氧化鋁。前述界 面活性劑之特定實例係包括非離子性界面活性劑、陽離子 性界面活性劑及陰離子性界面活性劑。前述黏著促進劑之 特定實例係包括乙烯基三甲氧基矽烷、乙烯基三乙氧基矽 烷、乙烯基三(2-甲氧基乙氧基)矽烷、N-(2-胺基乙基 )-3-胺基丙基甲基二甲氧基矽烷、N- (2-胺基乙基)-3-胺基丙基甲基三甲氧基矽烷、3-胺基丙.基三乙氧基矽烷、 3-縮水甘油基三甲氧基矽烷、3-縮水甘油基丙基甲基二甲 氧基矽烷、2-(3,4-環氧基環己基)乙基三甲氧基矽烷、 3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯氧丙基三甲氧基矽烷及3_锍基丙基三甲氧基矽 烷。前述抗氧化劑之特定實例係包括2,2-硫雙(4-甲基-6-第三丁基酚)及2,6-二-第三丁基酚。前述紫外線吸收劑 之特定實例包括2-(3-第三丁基-5-甲基-2-羥基苯基)-5-氯苯并三唑及烷氧基二苯基甲酮。前述凝結抑制劑之特定 實例係包括聚丙烯酸鈉。 可添加前述顯影性調節劑,以進一步改善自本發明輻 射敏感性組成物形成之塗膜於鹼顯影劑中之溶解度,且進 一步抑制在顯影之後的未溶解物質殘留。顯影性調節劑之 實例係爲有機酸。作爲該種有機酸,以具有不高於1,000 之分子量的脂族羧酸或含苯環羧酸較佳。 前述脂族羧酸之特定實例係包括單羧酸,諸如甲酸、 -39 - 200839444 乙酸、丙酸、丁酸、戊酸、特戊酸、己酸、二乙基乙酸、 庚酸及辛酸;二羧酸,諸如草酸、丙二酸、琥珀酸、戊二 酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、巴西基 _ 酸、甲基丙二酸、乙基丙二酸、二甲基丙二酸、甲基琥珀 酸、四甲基號_酸、環己院二甲酸、衣康酸、檸康酸、順 丁烯二酸、反丁烯二酸及中康酸·,及三羧酸,諸如丙三羧 酸、烏頭酸及樟腦酮酸。 φ 前述含苯環羧酸之說明例係包括羧基直接鍵結於苯基 之芳族羧酸及羧基經由碳鏈鍵結於苯基之羧酸。其特定實 例係包括芳族單羧酸,諸如苯甲酸、甲苯酸、枯茗酸、苯 連三酸及 林酸;芳族二羧酸,諸如苯二甲酸、異苯二甲 酸及對苯二甲酸;具有三或更多個官能基之芳族多羧酸, 諸如苯偏三酸、苯三甲酸、苯偏四酸及苯四甲酸;及苯基 乙酸、氫化阿托酸、氫化肉桂酸、扁桃酸、苯基琥珀酸、 阿托菱、肉桂酸、亞肉桂酸、香豆酸及繳形酸。 • 此等有機酸中,就鹼溶解度、於下文所述之溶劑的溶 劑及防止形成著色層部分以外之區域中的浮渣及膜殘留物 ^ 之觀點而言,脂族二羧酸及芳族二羧酸諸如丙二酸、己二 ^ 酸、衣康酸、檸康酸、順丁烯二酸、中康酸及苯二甲酸較 佳。 前述有機酸可單獨或二或更多種摻合使用。 本發明中,顯影性調節劑用量以整體輻射敏感性組成 物計較佳不大於10重量%,更佳爲0.001至10重量%,再 更佳爲0.0 1至1重量%。當顯影性調節劑之量大於10重 -40- 200839444 量%時’所形成之著色層對基板之黏著性在某些情況下可 能不足。 溶劑 本1發明輻射敏感性組成物包含前述著色劑(A )、鹼 可溶性樹脂(B )、多官能性單體(C )及感光聚合起始劑 (D )作爲必要組份且視需要包含前述其他添加劑。然而 ,該輻射敏感性組成物較佳係製備成除著色劑(A )以外 之組份溶解於適當溶劑中且著色劑(A )均勻分散之液體 組成物。 作爲溶劑,可選擇且適當地使用任何溶劑,其限制條 件爲其分散或溶解著色劑(A )、鹼可溶性樹脂(B )、多 官能性單體(C )及感光聚合起始劑(D )及其他添加劑’ 不與此等組份反應且具有適當之揮發性。 溶劑之說明例包括(聚)烷二醇單烷基醚’諸如乙二 醇單甲基醚、乙二醇單乙基醚、雙乙二醇單甲基醚、雙乙 二醇單乙基醚、雙乙二醇單正丙基醚、雙乙二醇單正丁基 醚、三乙二醇單甲基醚、三乙二醇單乙基醚、丙二醇單甲 基醚、丙二醇單乙基醚、雙丙二醇單甲基醚、雙丙二醇單 乙基醚、雙丙二醇單正丙基醚、雙丙二醇單正丁基釀、二 丙二醇單甲基醚及三丙二醇單乙基醚;(聚)院二醇單院 基醚乙酸酯,諸如乙二醇單甲基醚乙酸酯、乙二醇單乙基 醚乙酸酯、丙二醇單甲基醚乙酸酯及丙二醇單乙基釀乙酸 酯;乙酸3 -甲氧基丁酯;其他醚類,諸如雙乙二醇二甲基 -41 - 200839444 醚、雙乙二醇甲基乙基醚、雙乙二醇二乙基醚及四氫呋喃 ;酮類,諸如甲基乙基酮、環己酮、2_庚酮及3 -庚酮;乳 酸烷酯,諸如2-羥基丙酸甲酯及2-羥基丙酸乙酯;其他酯 〃 類,諸如2-羥基-2_甲基丙酸甲酯、2_羥基-2-甲基丙酸乙 酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3_乙氧基丙 酸甲酯、3-乙氧基丙酸乙酯、乙氧基乙酸乙酯、經基乙酸 乙酯、2 -經基-3-甲基丁酸甲酯、乙酸3 -甲基-3-甲氧基丁 • 酯、丙酸3 -甲基-3-甲氧基丁酯、乙酸乙酯、乙酸正丙酯 、乙酸異丙酯.、乙酸正丁酯、乙酸異丁酯、乙酸正戊酯、 乙酸異戊酯、丙酸正丁酯、丁酸乙酯、丁酸正丙酯、丁酸 異丙酯、丁酸正丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸 正丙酯、乙醯基乙酸甲酯、乙醯基乙酸乙酯及2_合氧基丁 酸乙酯;芳族烴,諸如甲苯及二甲苯;及竣醯胺,諸如 N -甲基Π比略陡酮、Ν,Ν·二甲基甲醯胺及n,N -二甲基乙醯 胺。 • 此等溶劑可單獨或二或更多種摻合使用。 此外,此等溶劑可與高沸點溶劑諸如苄基乙基醚、二 己基醚、丙酮基丙酮、異佛爾酮、己酸、辛酸、1-辛醇、 ^ 1-壬醇、苄醇、乙酸苄酯、苯甲酸乙酯、草酸二乙酯、順 丁烯二酸二乙酯、丁內酯、乙二醇碳酸酯、丙二醇碳 酸酯或乙二醇單苯基醚乙酸酯一起使用。 此等高沸點溶劑可單獨或二或更多種摻合使用。 前述溶劑中,就溶解度、顏料分散性、塗覆性及諸如 此類觀點而言,乙二醇單甲基醚乙酸酯、丙二醇單甲基醚 -42 - 200839444 乙酸酯、丙二醇單乙基醚乙酸酯、乙酸3 -甲氧基丁酯 乙一醇一甲基醚、環己酮、2 -庚酮、3 -庚酮、2_羥基 乙醋、丙酸3-甲基甲氧基丁酯、3-甲氧基丙酸乙酯 乙氧基丙酸甲酯、3_乙氧基丙酸乙酯、乙酸正丁酯' 異丁醋、乙酸正戊酯、乙酸異戊酯、丙酸正丁酯、丁 醋、丁酸異丙酯、丁酸正丁酯、丙酮酸乙酯及諸如此 較佳。作爲高沸點溶劑,以7 -丁內酯及諸如此類者 〇 、溶齊[[於本發明輻射敏感性組成物中之用量(溶劑 沸點溶劑之總量)以i 00重量份數鹼可溶性樹脂(B 較佳係爲100至1〇,〇〇〇重量份數,更佳5〇〇至5,〇〇〇 份數。當高沸點溶劑與溶劑一起使用於本發明輻射敏 組成物中時,其用量以溶劑總量計不大於2 0重量%, 係不大於1 0重量%。 形成著色層之方法 其次,描述使用本發明輻射敏感性組成物形成著 之方法。首先,描述著色層係爲包含構成濾色器之像 列的情況,接著描述著色層係爲黑基質之情況。 〔用以形成包含像素陣列之著色層的方法〕 首先,形成遮光層(黑基質)以於基板表面上分 成像素之區域。於此基板上施加其中分散有(例如) 顏料之液體輻射敏感性組成物,基板進行熱處理(預 、雙 丙酸 > 3- 乙酸 酸乙 類者 較佳 及高 )計 重量 感性 更佳 色層 素陣 隔形 紅色 烘烤 -43- 200839444 )以蒸發移除溶劑,而形成塗膜。之後,在此塗膜之一區 域照射輻射之後,以鹼顯影劑將塗膜顯影,溶解並移除未 曝光區域之塗膜,之後熱處理(後烘烤)以形成具有排列 _ 成預定圖案之紅色像素的像素陣列。 之後’施加其中個別分散有綠色顏料及藍色顏料之液 體輻射敏感性組成物,預烘烤,曝照輻射,以如同前述方 式顯影._,依序於同一基板上形成綠色像素陣列及藍色像素 Φ 陣列。因而可得到具有排列於基板上之紅色、綠色及藍色 像素陣列(著色層)的濾色器。然而,本發明中,形成前 述三顏色之像素陣列的順序不特別限制。 用以形成著色層之基板的說明例係包括玻璃、矽、聚 9 碳酸酯、聚酯、芳族聚醯胺、聚醯胺醯亞胺及聚醯亞胺。 此等基板可視需要進行適當之預處理,諸如使用矽烷偶聯 劑或諸如此類者進行化學處理、電漿處理、離子電鍍、濺 鍍、氣相反應方法或真空沈積。 φ 將輻射敏感性組成物施加於基板上之方法不特別限制 。該方法之說明例係包括使用狹縫噴嘴之方法(以下稱爲 p 「狹縫噴嘴塗覆方法」),諸如狹縫-及-旋轉塗覆法及狹 ^ 縫塑模塗覆法。 狹縫噴嘴塗覆方法中之塗覆條件在狹縫-及-旋轉塗覆 法時與在狹縫塑模塗覆法時不同,且視待塗覆基板之尺寸 或諸如此類者而改變。例如藉狹縫塑模塗覆法塗覆第五代 玻璃基板(1,100毫米xl,250毫米)時,自狹縫噴嘴送出 輻射敏感性組成物的量較佳係爲500至2,000微升/秒,更 -44- 200839444 佳係爲800至1,5 00微升/秒,塗覆速度較佳爲500至 1,500毫米/秒,更佳係爲700至1,200毫米/秒。 使用於狹縫噴嘴塗覆方法中之輻射敏感性組成物的固 體含量(組成物中除溶劑以外之組份的總重於組成物總重 中之比例)較佳係爲1 〇至2 0重量%,更佳係爲1 3至1 8 重量%。 當採用狹縫噴嘴塗覆方法時,預烘烤較佳係爲於減壓 下進行之「真空烘烤」。至於此種真空烘烤之條件,真空 度較佳約1 〇至1 5 0 P a,更佳約2 5至7 5 P a,溫度較佳約 6 0至1 2 0 °C,更佳約7 0至1 1 0 °C,烘烤時間較佳約1至5 分鐘,更佳約2至4分鐘。 移除溶劑後所形成之塗膜的厚度較佳係爲0.1至10 微米,更佳爲0.2至8.0微米,特佳係0.2至6.0微米。 之後,所形成之塗膜至少一部分進行曝光。此可如經 由具有適當之圖案的光罩進行照射輻射達成。 作爲使用於曝照之輻射,可使用例如可見光輻射、紫 外線輻射、遠紫外線輻射、電子束、X-射線或諸如此類者 。其中,具有190至450奈米波長之輻射較佳。 輻射曝光係例如約1 0至1 0,0 0 0焦耳/米2。 之後,塗膜以顯影劑顯影,以溶解並移除塗膜之未曝 光區域。 作爲前述顯影劑,較佳係爲包含碳酸鈉、氫氧化鈉、 氫氧化鉀、氫氧化四甲基銨、膽鹼、1,8_二氮雜雙環-〔 5·4·〇〕-7-十一碳烯、1,5_二氮雜雙環-〔4.3.0〕-5-壬烯或 -45- 200839444 諸如此類者之水溶液的鹼顯影劑。 可將適量之水溶性有機溶劑(諸如甲醇或乙醇)、界 面活性劑或諸如此類者添加於前述鹼顯影劑中。經顯影之 塗膜較佳係以水加以潤洗。 作爲顯影方法,可採用例如噴淋式顯影、噴霧式顯影 、浸漬式顯影、攪煉顯影或諸如此類者。 顯影較佳係於常溫進行約5至3 00秒。 之後,經顯影之塗膜進行後烘烤,以於基板上形成著 色層。 後烘烤較佳係於180至23 0 °C進行約20至40分鐘。 藉由依所示順序以其中個別分散有紅、綠及藍顏料之 著色層形成組成物重複前述步驟,可得到形成於同一基板 上之具有紅色像素陣列、綠色像素陣列及藍色像素陣列( 著色層)的濾色器。 〔用以形成作爲黑基質之著色層的方法〕 在前述「用以形成包含像素陣列之著色層的方法」中 ,藉由使用其中分散有黑色顏料或紅色、黃色及藍色顏料 之混合物的輻射敏感性組成物依序地進行前述步驟,可製 得具有排列成預定配置之黑基質圖案的基板。 所形成之具有著色層或含著色層之黑基質的濾色器極 適用於例如彩色液晶顯示器、彩色攝像管裝置、彩色感應 器及諸如此類者。 -46- 200839444 液晶顯示裝置 本發明液晶顯示裝置包含具有自本發明輻射敏感性組 成物形成之著色層的濾色器或包含自本發明輻射敏感性組 _ 成物形成之著色層的黑基質。 本發明液晶顯示裝置可具有任何適當之結構。例如, 其可具有其中在異於在表面上形成有薄膜電晶體(TFT ) 之驅動用基板的基板上形成濾色器,驅動用基板及具有濾 φ 色器之基板係彼此面對而其間放置液晶層之結構,或其中 在表層配置有薄膜電晶體(TFT )之驅動用基板表面上形 成濾色器,此基板與表層上形成由ITO (摻有錫之氧化 銦)製得之電極的基板係彼此面對而其間放置液晶層之結 構。後一種結構具有可大幅改善開口率且製得明亮、高明 晰度彩色液晶顯示裝置之優點。 熟習此技術者應可自己明瞭前述液晶顯示裝置之其他 特定具體實施態樣。 # 本發明液晶顯示裝置之色彩純度優異 ^ 【實施方式】 〃 實施例 以下參考實施例進一步描述本發明。然而,本發明應 不受限於以下實施例。 以下實施例中,以聚苯乙烯計之重量平均分子量( Mw)係藉凝膠滲透層析(GPC)使用 Tosoh Corporation 之GPC管柱(包含串連之兩G2000HXL、一 G3000HXL及 -47- 200839444 一 G4 00 0HXL )且以四氫呋喃作爲溶離溶劑,於丨.〇毫升/ 分鐘流速及40 °C管柱溫度下,使用單分散性聚苯乙烯作爲 標準物進行測量。 <苯乙烯環氧樹脂之合成例> 合成例1 於裝置有冷凝器及攪動器之燒瓶中,將4 〇 . 0克對-乙 烯基苄基縮水甘油基醚、27· 0克N-苯基順丁烯二醯亞胺 、17.0克苯乙烯及16.0克甲基丙烯酸苄酯溶解於300克 丙二醇單甲基醚乙酸酯中。之後,將4.0克2,2’-偶氮基雙 異丁腈及6 · 0克α -甲基苯乙燦二聚物添加於該混合物中, 之後以氮沖洗1 5分鐘。之後,反應器於攪動下加熱至8〇 °C,混合物反應5小時,以得到含有2 5重量%苯乙烯環氧 樹脂〔A-1〕之溶液。此苯乙儲環氧樹脂〔A-1〕以聚苯乙 烯計之重量平均分子量(Mw)係爲6,000。 合成例2至8 以如同前述合成例1之方式製得含有2 5重量%苯乙烯 環氧樹脂〔A-2〕至〔A-8〕之溶液,不同處係單體類型及 用量及2,2’-偶氮基雙異丁腈及甲基苯乙燒二聚物之量 係如表1所示般地改變。表1中組份之量係以重量(克) 表示。 此等合成例所得之苯乙烯環氧樹脂以聚苯乙烯計之重 量平均分子量(Mw)係列於表1中。 -48- 200839444 £ S.Ex.8 1 A-8 | 34.0 1 43.0 | 1 〇 16.0 | 1 〇 00 〇 〇6 5,500 1 S.Ex.7 A-7 40.0 1 1 40.0 | 1 20.0 1 P 〇 VO ο 1 S.Ex.6 A-6 1 44.0 40.0 1 16.0 1 1 I 1 P 寸 p ο ο οο" S.Ex.5 < 40.0 | 27.0 1 1 L祉―丨 〇 10.0 〇 in ο vd 5,000 S.Ex.4 A-4 1 44.0 1 40.0 | 1 1 1 16.0 | I P ο ν〇 6?000 S.Ex.3 _ Μ」 50.0 1 27.0 | 1 「―17·0— 1 〇 νο 1 ο rn ο ¥ 15,000 S.Ex.2 A-2 ο | 38.0 1 1 1 28.0 1 30.0 1 Ο rn ο to ο ο ri S.Ex.l A-l 40.0 | 27.0 | 1 丨 17·0 I 16.0 1 Ο — Ο ο I 樹脂名稱_ 1 對-乙烯基苄基縮水甘油基醚 | Ν-苯基順丁烯二醯亞胺 蹈 I 苯乙烯 1 甲基丙烯酸苄酯 | 甲基丙烯酸2-羥基乙酯 1 2,2’·偶氮基雙異丁腈 1 α-甲基苯乙烯二聚物 1 重量平均分子量(Mw) 屡怪4Π: .xws(wherein R represents an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms or a phenyl group, and R12 and R13 each independently form a JLL surface having no hydrogen atom and having from -20 to 20 carbon atoms. An alkyl group, a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group which may be substituted or a monovalent alicyclic group having 7 to 20 carbon atoms (excluding the aforementioned ring-based group), and R14 is represented by 1 An alkyl group of 12 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 12 carbon atoms or a cycloalkoxy group having 3 to 8 carbon atoms, when plural When rM, -29-200839444 may be the same or different from each other, and R15 represents a monovalent oxygen-containing heterocyclic group having 4 to 20 carbon atoms, a monovalent nitrogen-containing heterocyclic group having 4 to 20 carbon atoms or A monovalent sulfur-containing heterocyclic group of 4 to 20 carbon atoms. When a plurality of R15 are present, they may be the same or different from each other, P is an integer from 〇 to 6, and q is 〇 or l, n is m is an integer from 0 to 5, and the constraint is (n + m ) $ 5 ) 〇 as an alkyl group having 1 to 20 carbon atoms of R11 in the formula (D-1) Description Including methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n- Base, n-decyl and n-dodecyl. Illustrative examples of the cycloalkyl group having 3 to 8 carbon atoms as R11 include a cyclopentyl group and a cyclohexyl group. Preferred examples of R11 in the formula (D-1) include a methyl group and an ethyl group. Illustrative examples of the alkyl group having 1 to 20 carbon atoms of R12 and R13 in the formula (D-1) include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, and Tributyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-decyl, n-undecyl and n-dodecyl. Illustrative examples of the cycloalkyl group having 3 to 8 carbon atoms of R12 and R13 include a cyclopentyl group and a cyclohexyl group. Illustrative examples of the substituent of the phenyl group of R12 and R13 include an alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, a third butyl group, a n-pentyl group and a n-hexyl group; a cycloalkyl group having 3 to 6 carbon atoms, such as a cyclopentyl group and a cyclohexyl group; an alkoxy group having 1 to 6 carbon atoms, such as a methoxy group, B -30- 200839444 oxy, n-propoxy, isopropoxy, n-butoxy and tert-butoxy; cycloalkoxy having 3 to 6 carbon atoms, such as cyclopentyloxy and cyclohexyloxy a phenyl group; and a halogen atom such as a fluorine atom and a chlorine atom. The number of substituents as the phenyl group of R12 and R13 is preferably from 4 to 1, more preferably 0 or 1. Further, illustrative examples of the monovalent alicyclic group having 7 to 20 carbon atoms of R12 and R13 (excluding the aforementioned cycloalkyl group) include a group having a 1-alkylcycloalkane structure and having a tricycloalkane. a group of a structure, a group having a spiro structure, a group having an olefin structure, and a group having an adamantane structure. As R12 and R13 in the formula (D-1), a hydrogen atom, a methyl group and an ethyl group are preferred. Illustrative examples of the alkyl group having 1 to 12 carbon atoms of R14 in the formula (D-1) include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, second butyl group, and third group. Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-decyl, n-undecyl and n-dodecyl. Illustrative examples of the cycloalkyl group having 3 to 8 carbon atoms as R14 include a cyclopentyl group and a cyclohexyl group. Illustrative examples of the alkoxy group having 1 to 12 carbon atoms as R14 include a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, a third butoxy group, and a n-pentyl group. Oxy, n-hexyloxy, n-heptyloxy, n-octyloxy, n-decyloxy, n-decyloxy, n-undecyloxy and n-dodecyloxy. The illustrative examples of the cycloalkoxy group having 3 to 8 carbon atoms of R14 include a cyclopentyloxy group and a cyclohexyloxy group. As R14 in the formula (D-1), methyl, ethyl, n-propyl, isopropyl, n-butyl, methoxy and ethoxy groups are preferred. Monovalent having 4 to 20 carbon atoms as R15 in the formula (D-1) -31 - 200839444 oxygen-containing heterocyclic group, monovalent nitrogen-containing heterocyclic group having 4 to 20 carbon atoms, and having 4 to 20 carbons Illustrative examples of monovalent sulfur-containing heterocyclic groups of atoms include thioindolyl, azirretyl, dihydroazetyl, dioxolanyl, triamyl, oxathiocyclohexane, thiazolyl, dioxadiazine , oxahydroindenyl, dithylnaphthyl, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, furazolyl, piperazine Base, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolinyl, morphonyl, piperazinyl, quinacridyl, fluorenyl, isodecyl, benzofuranyl, benzene幷Thienyl, pyridazinyl, chromenyl, quinolyl, isoquinolyl, fluorenyl, quinazolinyl, porphyrinyl, pyridazinyl, acridinyl, oxazolyl, anthracene Base, phenanthrene D, thioxanthyl, phenazinyl, phenothiaphthyl, oxathiazide, phenoxazinyl, thioxyl, tetrahydrofuranyl and tetrahydropyranyl. As the Ri5, dioxolane group, tetrahydrofuranyl group and tetrahydropyranyl group in the formula (D-1), it is preferred. The p in the formula (D-1) is preferably 〇, 1 or 2, especially 1. n in the formula (D-1) is preferably 〇, 1 or 2, especially, and m in the formula (D-1) is preferably 〇 or i. In the compound of the formula (D · 1 ), the compound wherein q is ruthenium (hereinafter referred to as "carbazole compound (1)") and the compound wherein 4 is 1 and (5) is 1 (hereinafter referred to as "carbazole" Compound (2)") is preferred. Specific examples of the aforementioned carbazole compound (1) include b [% ethyl·6_benzamide-9·η·-carbazole-3·yl]-U2-decane-2-肟-◦~benzol Acid ester, 1-[9.ethyl-6-benzhydryl-911-oxazol-3-yl]-1,2-decane-2_肟-〇_-32- 200839444 acetate, 1- [9-ethyl-6-benzamide-9.11.-n-oxazol-3-yl]-1,2-pentane-2-indole-0-acetate, 1-[9-ethyl-6- Benzamidine·9·Η._oxazol-3-yl]-octane-1-one oxime-0-acetate, 1-[9-ethyl-6-(2-methylbenzamide) -9.11.-Acoxazol-3-yl]-ethane-1-one oxime-indole-benzoate, 1-[9-ethyl-6-(2-methylbenzamide)-9.11.- Oxazol-3-yl]-ethane-1-one oxime-indole-acetate, 1-[9-n-butyl-6-(2-ethylbenzylformamidine)-9.Η.-isoxazole 3-yl]-ethane-1-one oxime-indole-benzoate, ethyl ketone-1-[9-ethyl-6-(2-methyl-4-tetrahydrofurylbenzophenone)-9 ·Η·-oxazol-3-yl]-1-(Ο-acetamidine), Ethyl-1-(9-ethyl-6-(2-methyl-4-tetrahydropyranylbenzene)醯)-9·Η·- oxazol-3-yl]-1-(Ο-acetamidine), ethyl ketone-1-[ 9-ethyl-6-( 2-methyl-5-tetrahydrofuranylbenzene Hyperthyroidism)-9·Η ·- oxazol-3-yl]-1-( 〇-acetamidine), ethyl ketone-1-[ 9-ethyl-6- ( 2-methyl-5-tetrahydropyranyl benzamidine) -9·Η·-oxazol-3-yl]-1-(Ο-acetamidine), and 乙--1-[9-ethyl-6- { 2 -methyl-4- ( 2,2 - monomethyl-1,3-mono-oxopentyl)benzamide}-9.Η·-oxazol-3-yl]-1-(0-acetamidine). Specific examples of the aforementioned carbazole compound (2) include ethyl ketone-1-[9-ethyl-6-(2-methyl-4-tetrahydrofurylmethoxybenzylammonium)-9.Η.-carbazole 3-yl]-1-(0-acetamidine), -33- 200839444 ethyl ketone-1-[9-ethyl-6-(2-methyl-4_tetrahydropyranyl methoxybenzene Formamidine)-9.11.-carbazol-3-yl]-1-(0-acetamidine), ethyl ketone-1-[9-ethyl-6-(2-methyl-5-tetrahydrofuranylmethoxy) Benzobenzidine··9·Η·-carbazol-3-yl]-1-(0-acetamidine), ethyl ketone-1-[9-ethyl-6- (2-methyl-5_ Tetrahydropyranomethoxybenzyl hydrazide)-9·Η·-oxazol-3-yl]-1-(0-acetamidine), and ethyl ketone-1-[9-ethyl-6- { 2-Methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzimid}-9-Η--oxazol-3-yl]-1- (0-acetamidine) wherein 1-[9-ethyl-6-(2-methylbenzimidoxime)oxazol-3-yl]-ethane-1 is used in the carbazole compound (1) -Ketone oxime-0-acetate and the hexa-(9-ethyl-6-(2-methyl-4-tetramethylenefuranyl methoxybenzoate) in the compound (2)醯)carbazol-3-yl]-1-(0-acetamidine) and ethene-1-[9-ethyl-6- {2-A -4- ( 2,2 - _^methyl-1,3 -monooxypenta) methoxybenzimid} oxazol-3-yl]-1-(0-acetamidine) is preferred . Ethyl ketone-1-[ 9-ethyl-6-{ 2-methyl-4-( 2,2-dimethyl-1,3-dioxolanyl) in the carbazole compound (2) ) methoxybenzimid} -9.H--oxazol-3-yl]-1-(0-acetamidine). The above-mentioned other examples of the ruthenium compound include 1,2-anthracene-l-[4-(phenylthio)benyl]-2·(0-pretylated carbenazole) 1,2-butanedione-1 -[4-(phenylthio)phenyl]-2-(0-benzylidenehydrazide) 1,2-butanedione-1-[4-(phenylthio)phenyl]-2- (0 - 乙醯基肟), -34- 200839444 1,2· octodione-1-[ 4-(methylthio)phenyl]-2-( 0-benzylidene fluorenyl), and 1,2 - Octapressin-1-[4-(phenylthio)phenyl]-2-(0-(4-methylbenzhydrylhydrazine)). Among them, 1,2-octanedione-1-[4-(phenylthio)phenyl]-2-(indenyl-benzhydrylhydrazine) is particularly preferred. Illustrative examples of the biimidazole compound include 2,2'-bis(2.chlorophenyl)-4,4',5,5'-tetrakis(4-ethoxycarbonylphenyl)-1,2. Imidazole, 2,2'-bis(2-bromophenyl)-4,4,5,5'-tetrakis(4ethoxycarbonylphenyl)-1,2'-biimidazole, 2,2'-double (2-Chlorophenyl)-4,4f,5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4' ,5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis(2,4,6-trichlorophenyl)-4,4',5,5'-tetraphenyl -1,2'-biimidazole, 2,2'-bis(2-bromophenyl)-4,4',5,5'-tetraphenyl-1,2.biimidazole, 2,2'-double (2,4-dibromophenyl)-4,4\5,5'-tetraphenyl-1,2'biimidazole, and 2,2'-bis(2,4,6-tribromophenyl) -4,4',5,5'-tetraphenyl-1,2'-biimidazole. When the biimidazole compound is used as the photosensitive polymerization initiator (D) in the radiation-sensitive composition of the present invention, it is preferably used in combination with a hydrogen donor because the sensitivity can be further improved. "Hydrogen donor" means a compound which provides a hydrogen atom to a radical which is exposed from a biimidazole compound. Preferred as the hydrogen donor 'thiol compound, amine compound and the like. The aforementioned thiol compound is a compound having a benzene ring or a heterocyclic ring and one or more (preferably one to three, more preferably one or two) groups bonded directly to the fluorenyl group of the ring. Specific examples of the thiol compound include 2-mercaptobenzothiazole, -35-200839444 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2,5-dimercapto-1,3,4- Thiadiazole and 2-mercapto-2,5-dimethylaminopyridine. The above amine compound is a compound having a benzene ring or a heterocyclic ring and one or more (preferably one to three 'more preferably one or two) amine groups directly bonded to the ring. Specific examples of the amine compound include 4,4'-bis(dimethylamino)diphenyl ketone, 4,4'-bis(diethylamino)diphenyl ketone, 4-diethyl Aminoethyl phenyl benzene, 4-dimethylamino propyl phenyl benzene, ethyl 4-dimethylamino benzoate, isoamyl 4-dimethylaminobenzoate, 4-dimethylamine Benzoic acid and 4-dimethylaminobenzonitrile. When a bisimidazole compound is used as the photopolymerization initiator (D) in the radiation-sensitive composition of the present invention, it is preferred to use both a thiol compound and an amine compound as a hydrogen donor because of sensitivity of the radiation-sensitive composition. The color is high, and the formed color layer hardly falls off from the substrate during development, and the strength of the colored layer is also high. Illustrative examples of the aforementioned benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin butyl ether, and methyl 2-benzoin benzoate. Illustrative examples of the aforementioned acetylated benzene compound include 2,2-dimethoxyacetamidine, 2,2-diethoxyethyl benzene, and 2,2-dimethoxy-2-phenyl acetylene. Benzene, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 2-methyl Base-(4-methylthiophenyl-2-morpholine-1-propan-1-one, 4-(2-hydroxyethoxy)phenyl-2-(hydroxy-2-propyl)one, 2 -benzyl-2-dimethylamino-1-(4-morpholinylphenyl)butan-1-one, 1-hydroxycyclohexyl phenyl ketone and 2,2-dimethoxy-1,2- Diphenylethan-1-one. -36- 200839444 Methotone benzoquinone and phosphinated bis) oxazine A-S - The illustrative examples of the aforementioned diphenyl ketone compound include 4,4'-bis (two Illustrative examples of the aforementioned α-diketone compounds of the above-mentioned α-diketone compounds include bis-indenyl, dimethylhydrazine and benzene. Methyl carbazate. Illustrative examples of the aforementioned polycyclic guanidine compound include hydrazine, 2-ethyl hydrazine, 2-tert-butyl fluorene, and 1,4-naphthoquinone. Illustrative examples of the aforementioned xanthone compounds include xanthone and thioxanthone 2-chloroxanthone. Illustrative examples of the aforementioned phosphine compound include bis(2,4,6-trimethylmethylindenyl)phenylphosphine oxide and oxidized 2,4,6-trimethylbenzimidyldiphenylphosphonium. Illustrative examples include triazine compounds having a halomethyl group such as 2,4,6-tris(trichloromethyl)-s-triazine, 2-methyl-4,6-(trichloromethyl)- S-triazine, 2-[2((furan-2-yl)vinyl] 4,6-bis(trichloromethyl)-s-triazine, 2-[2-(5-methylfuran-2) -ylvinyl]-4,6-bis(trichloromethyl)-s-triazine, 2-[2-(4-diethylamino-2-methylphenyl)vinyl]-4,6 - bis(trichloromethyl)-s-tris(2-(2-(3,4-dimethoxyphenyl)vinyl]_4,6-bis(trichloro)-s-triazine, 2 - (4-methoxyphenyl)-4,6-bis(trichloromethyl)triazine, 2-(4-ethoxystyryl)_4,6-bis(trichloromethyl)-S · azine and 2-(4-n-butoxyphenyl)_4,6-bis(trichloromethyl)-s-triazine These photopolymerization initiators can be used alone or in combination of two or more. Wherein the amount of the photopolymerization initiator (D) is from 1 to 30 - 200839444 parts of the polyfunctional monomer C) The total amount of the monofunctional monomer is preferably from 0.01 to 500 parts by weight, more preferably from 1 to 300 parts by weight, especially from 10 to 200 parts by weight. When the photosensitive polymerization initiator (D) is used When the amount is less than 0.01 part by weight, the curing by exposure is insufficient, and it may become difficult to obtain a pattern array having a coloring layer pattern arranged according to a predetermined arrangement, and when the amount is more than 500 parts by weight, the formation is performed. The dyed layer is easily detached from the substrate during development, and is easy to form scum and is liable to remain in the unexposed area of the substrate or on the light-shielding layer. The photosensitive polymerization initiator contained in the radiation-sensitive composition of the present invention (D) It is preferred to contain a ruthenium compound, and more preferably a compound represented by the above formula (D-1). When the photopolymerization initiator (D) contains a ruthenium compound and other photopolymerization initiator, it is combined with the ruthenium compound. Other photosensitive polymerization initiators used are preferably a biimidazole compound, an ethenylbenzene compound, a triazine compound, a benzoin compound, a diphenyl ketone compound, an α-diketone compound, a polycyclic guanidine compound, and a xanthone. Compound The diazonium compound, the key salt and the sulfhydryl sulfonate compound, and the ethoxylated benzene compound is particularly preferred. In the present invention, the cerium compound is preferably used in an amount of at least 20% by weight based on the total amount of the photosensitive polymerization initiator (D). %, more preferably at least 50% by weight. Other additives In addition to the aforementioned coloring agent (A), alkali-soluble resin (Β), polyfunctional monomer (C), and photopolymerization initiator (D), the radiation of the present invention The sensitive composition may contain various other additives as needed. Examples of such other additives include chelating agents, surfactants 38·200839444, adhesion promoters, antioxidants, ultraviolet absorbers, coagulation inhibitors, and developability modifiers. . Specific examples of the aforementioned chelating agents include glass and alumina. Specific examples of the aforementioned surfactant include nonionic surfactants, cationic surfactants, and anionic surfactants. Specific examples of the aforementioned adhesion promoter include vinyl trimethoxy decane, vinyl triethoxy decane, vinyl tris(2-methoxyethoxy) decane, N-(2-aminoethyl)- 3-aminopropylmethyldimethoxydecane, N-(2-aminoethyl)-3-aminopropylmethyltrimethoxydecane, 3-aminopropylpropyltriethoxydecane , 3-glycidyltrimethoxydecane, 3-glycidylpropylmethyldimethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, 3-chloropropane Methyldimethoxydecane, 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, and 3-mercaptopropyltrimethoxydecane. Specific examples of the aforementioned antioxidant include 2,2-thiobis(4-methyl-6-tert-butylphenol) and 2,6-di-t-butylphenol. Specific examples of the aforementioned ultraviolet absorber include 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole and alkoxydiphenylmethanone. Specific examples of the aforementioned coagulation inhibitors include sodium polyacrylate. The aforementioned developability adjuster may be added to further improve the solubility of the coating film formed from the radiation-sensitive composition of the present invention in an alkali developer, and further suppress the residue of undissolved substances after development. An example of the developability modifier is an organic acid. As such an organic acid, an aliphatic carboxylic acid or a benzene-containing carboxylic acid having a molecular weight of not more than 1,000 is preferred. Specific examples of the aforementioned aliphatic carboxylic acid include monocarboxylic acids such as formic acid, -39 - 200839444 acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, diethyl acetic acid, heptanoic acid, and octanoic acid; Carboxylic acids, such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, basal acid, methylmalonic acid, ethyl Malonic acid, dimethylmalonic acid, methyl succinic acid, tetramethyl carboxylic acid, cyclohexan dicarboxylic acid, itaconic acid, citraconic acid, maleic acid, fumaric acid and medium Kang acid, and tricarboxylic acids such as glycerol tricarboxylic acid, aconitic acid and camphorone acid. φ The above-mentioned illustrative examples of the benzene-containing carboxylic acid include an aromatic carboxylic acid in which a carboxyl group is directly bonded to a phenyl group, and a carboxylic acid in which a carboxyl group is bonded to a phenyl group via a carbon chain. Specific examples thereof include aromatic monocarboxylic acids such as benzoic acid, toluic acid, lauric acid, benzotricarboxylic acid and linonic acid; aromatic dicarboxylic acids such as phthalic acid, isophthalic acid and terephthalic acid An aromatic polycarboxylic acid having three or more functional groups, such as trimellitic acid, trimellitic acid, pyromellitic acid, and pyromellitic acid; and phenylacetic acid, hydrogenated atropic acid, hydrogenated cinnamic acid, almond Acid, phenyl succinic acid, atropine, cinnamic acid, cinnamic acid, coumaric acid and chelating acid. • Among these organic acids, aliphatic dicarboxylic acids and aromatics are used in view of alkali solubility, solvent of the solvent described below, and scum and film residues in areas other than the formation of the coloring layer portion. Dicarboxylic acids such as malonic acid, hexanedioic acid, itaconic acid, citraconic acid, maleic acid, mesaconic acid and phthalic acid are preferred. The aforementioned organic acids may be used singly or in combination of two or more. In the present invention, the developer adjuster is preferably used in an amount of not more than 10% by weight, more preferably 0.001 to 10% by weight, still more preferably 0.01 to 1% by weight based on the total radiation-sensitive composition. When the amount of the developability adjuster is more than 10% -40 - 200839444% by mass, the adhesion of the formed color layer to the substrate may be insufficient in some cases. Solvent The radiation-sensitive composition of the present invention comprises the above-mentioned coloring agent (A), alkali-soluble resin (B), polyfunctional monomer (C), and photopolymerization initiator (D) as essential components and, if necessary, the aforementioned Other additives. However, the radiation-sensitive composition is preferably prepared as a liquid composition in which components other than the colorant (A) are dissolved in a suitable solvent and the colorant (A) is uniformly dispersed. As the solvent, any solvent may be selected and suitably used, which is limited to dispersing or dissolving the colorant (A), the alkali-soluble resin (B), the polyfunctional monomer (C), and the photopolymerization initiator (D). And other additives' do not react with these components and have appropriate volatility. Illustrative examples of the solvent include (poly)alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, bisethylene glycol monomethyl ether, and diethylene glycol monoethyl ether. , bisethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether , dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl brewing, dipropylene glycol monomethyl ether and tripropylene glycol monoethyl ether; (poly) hospital II Alcohol monoether ether acetates, such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl acetate; 3-methoxybutyl acetate; other ethers such as bisethylene glycol dimethyl-41 - 200839444 ether, bisethylene glycol methyl ethyl ether, diethylene glycol diethyl ether and tetrahydrofuran; ketones , such as methyl ethyl ketone, cyclohexanone, 2 - heptanone and 3-heptanone; alkyl lactate, such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate; other esters , such as methyl 2-hydroxy-2-methylpropanoate, ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3_ Methyl ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl acetate, 2-methyl-methyl 3-methylbutanoate, 3-methyl acetate -3-methoxybutyl ester, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, N-amyl acetate, isoamyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, acetone N-propyl acrylate, methyl acetoxyacetate, ethyl acetoxyacetate and ethyl 2- oxybutyrate; aromatic hydrocarbons such as toluene and xylene; and decylamines such as N-methyl hydrazine Slightly ketone, hydrazine, hydrazine dimethylformamide and n,N-dimethylacetamide. • These solvents may be used alone or in combination of two or more. In addition, such solvents may be combined with high boiling solvents such as benzyl ethyl ether, dihexyl ether, acetonyl acetone, isophorone, caproic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, acetic acid. Benzyl ester, ethyl benzoate, diethyl oxalate, diethyl maleate, butyrolactone, ethylene glycol carbonate, propylene glycol carbonate or ethylene glycol monophenyl ether acetate are used together. These high boiling solvents may be used singly or in combination of two or more. Among the foregoing solvents, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether-42 - 200839444 acetate, propylene glycol monoethyl ether B, in terms of solubility, pigment dispersibility, coatability, and the like Acid ester, 3-methoxybutyl acetate, ethyl alcohol monomethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 2-hydroxyethyl vinegar, 3-methylmethoxybutyl propionate, Ethyl 3-methoxypropionate methyl ethoxy propionate, ethyl 3-ethoxypropionate, n-butyl acetate 'isobutyl vinegar, n-amyl acetate, isoamyl acetate, n-butyl propionate Esters, butyl vinegar, isopropyl butyrate, n-butyl butyrate, ethyl pyruvate and the like are preferred. As a high-boiling solvent, 7-butyrolactone and the like, dissolved, [[The amount of the radiation-sensitive composition of the present invention (the total amount of the solvent boiling solvent) is i 00 parts by weight of the alkali-soluble resin (B) It is preferably 100 to 1 Torr, 〇〇〇 part by weight, more preferably 5 〇〇 to 5, 〇〇〇 part. When a high boiling point solvent is used together with a solvent in the radiation sensitive composition of the present invention, the amount thereof is used. Not more than 20% by weight, based on the total amount of the solvent, is not more than 10% by weight. Method of forming a coloring layer Next, a method of forming a radiation-sensitive composition using the present invention will be described. First, the coloring layer is described as comprising In the case of the image column of the color filter, the case where the colored layer is a black matrix will be described. [Method for forming a coloring layer including a pixel array] First, a light shielding layer (black matrix) is formed to be divided into pixels on the surface of the substrate. a liquid radiation sensitive composition in which, for example, a pigment is dispersed, and the substrate is subjected to heat treatment (pre-, dipropionic acid > 3-acetic acid, B is preferred and high) weight sensitivity Better color layer matrix array red baking -43- 200839444 ) The solvent is removed by evaporation to form a coating film. Thereafter, after irradiating the radiation to a region of the coating film, the coating film is developed with an alkali developer, and the coating film of the unexposed region is dissolved and removed, followed by heat treatment (post-baking) to form a red color having a predetermined pattern A pixel array of pixels. Then 'applying a liquid radiation-sensitive composition in which individual green pigments and blue pigments are dispersed, pre-baked, exposed to radiation, developed as described above. _, forming a green pixel array and blue on the same substrate in sequence Pixel Φ array. Thus, a color filter having red, green, and blue pixel arrays (colored layers) arranged on the substrate can be obtained. However, in the present invention, the order in which the pixel array of the above three colors is formed is not particularly limited. Illustrative examples of the substrate used to form the colored layer include glass, ruthenium, poly 9 carbonate, polyester, aromatic polyamine, polyamidimide, and polyimine. Such substrates may be suitably pretreated as desired, such as by chemical treatment, plasma treatment, ion plating, sputtering, gas phase reaction methods or vacuum deposition using a decane coupling agent or the like. φ The method of applying the radiation-sensitive composition to the substrate is not particularly limited. The illustrative examples of the method include a method of using a slit nozzle (hereinafter referred to as p "slit nozzle coating method") such as a slit-and-spin coating method and a slit coating method. The coating conditions in the slit nozzle coating method are different in the slit-and-spin coating method than in the slit molding method, and vary depending on the size of the substrate to be coated or the like. For example, when a fifth-generation glass substrate (1,100 mm x 1,250 mm) is applied by a slit molding method, the amount of the radiation-sensitive composition sent from the slit nozzle is preferably 500 to 2,000 μm. l / sec, more -44 - 200839444 better than 800 to 1,500 liters / sec, coating speed is preferably 500 to 1,500 mm / sec, more preferably 700 to 1,200 mm / sec . The solid content of the radiation-sensitive composition used in the slit nozzle coating method (the ratio of the total weight of the components other than the solvent in the composition to the total weight of the composition) is preferably from 1 Torr to 20% by weight. %, more preferably from 1 3 to 18% by weight. When the slit nozzle coating method is employed, the prebaking is preferably "vacuum baking" under reduced pressure. As for the vacuum baking condition, the degree of vacuum is preferably from about 1 Torr to 150 Å, more preferably from about 25 to 7 5 P a, and the temperature is preferably from about 60 to 120 ° C, more preferably about The baking time is preferably from about 1 to 5 minutes, more preferably from about 2 to 4 minutes, from 70 to 110 °C. The thickness of the coating film formed after removing the solvent is preferably from 0.1 to 10 μm, more preferably from 0.2 to 8.0 μm, particularly preferably from 0.2 to 6.0 μm. Thereafter, at least a part of the formed coating film is exposed. This can be achieved by irradiating radiation through a reticle having a suitable pattern. As the radiation to be used for exposure, for example, visible light radiation, ultraviolet radiation, far ultraviolet radiation, electron beam, X-ray or the like can be used. Among them, radiation having a wavelength of 190 to 450 nm is preferred. The radiation exposure is, for example, about 10 to 10,0 0 joules per square meter. Thereafter, the coating film is developed with a developer to dissolve and remove the unexposed areas of the coating film. As the developer, it is preferred to contain sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo-[5·4·〇]-7- An alkali developer of an undecene, 1,5-diazabicyclo-[4.3.0]-5-decene or -45-200839444 aqueous solution such as those. An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, an surfactant or the like may be added to the aforementioned alkali developer. The developed coating film is preferably rinsed with water. As the developing method, for example, spray development, spray development, immersion development, smelting development or the like can be employed. Development is preferably carried out at room temperature for about 5 to 300 seconds. Thereafter, the developed coating film is post-baked to form a colored layer on the substrate. The post-baking is preferably carried out at 180 to 23 ° C for about 20 to 40 minutes. By repeating the foregoing steps in a coloring layer forming composition in which red, green, and blue pigments are individually dispersed in the order shown, a red pixel array, a green pixel array, and a blue pixel array (colored layer) formed on the same substrate can be obtained. Color filter. [Method for forming a coloring layer as a black matrix] In the above "method for forming a coloring layer including a pixel array", by using radiation in which a black pigment or a mixture of red, yellow, and blue pigments is dispersed The sensitive composition is sequentially subjected to the foregoing steps, and a substrate having a black matrix pattern arranged in a predetermined configuration can be obtained. The color filter formed with a colored layer or a black matrix containing a colored layer is extremely suitable for use in, for example, a color liquid crystal display, a color camera tube device, a color sensor, and the like. -46- 200839444 Liquid Crystal Display Device The liquid crystal display device of the present invention comprises a color filter having a coloring layer formed from the radiation-sensitive composition of the present invention or a black matrix comprising a coloring layer formed from the radiation-sensitive composition of the present invention. The liquid crystal display device of the present invention can have any suitable structure. For example, it may have a color filter formed on a substrate different from a driving substrate on which a thin film transistor (TFT) is formed on the surface, and the substrate for driving and the substrate having the filter chrominator face each other with a space therebetween a structure of a liquid crystal layer, or a color filter formed on a surface of a driving substrate on which a thin film transistor (TFT) is disposed on a surface layer, and a substrate on which an electrode made of ITO (indium oxide doped with tin) is formed on the substrate and the surface layer A structure in which a liquid crystal layer is placed facing each other. The latter structure has the advantage of greatly improving the aperture ratio and producing a bright, high-definition color liquid crystal display device. Those skilled in the art should be able to clarify other specific embodiments of the foregoing liquid crystal display device. # The liquid crystal display device of the present invention is excellent in color purity. [Embodiment] 实施 Embodiments The present invention will be further described below with reference to examples. However, the invention should not be limited to the following examples. In the following examples, the weight average molecular weight (Mw) in terms of polystyrene was determined by gel permeation chromatography (GPC) using a GPC column from Tosoh Corporation (including two G2000HXL, one G3000HXL, and -47-200839444 in series). G4 00 0HXL) was measured using tetrahydrofuran as the dissolution solvent at a flow rate of 〇.〇ml/min and a column temperature of 40 °C using monodisperse polystyrene as a standard. <Synthesis Example of Styrene Epoxy Resin> Synthesis Example 1 In a flask equipped with a condenser and an agitator, 4 g of p-vinylbenzyl glycidyl ether and 27.0 g of N- Phenyl maleimide, 17.0 g of styrene and 16.0 g of benzyl methacrylate were dissolved in 300 g of propylene glycol monomethyl ether acetate. Thereafter, 4.0 g of 2,2'-azobisisobutyronitrile and 6.0 g of α-methylphenethyl dimer were added to the mixture, followed by rinsing with nitrogen for 15 minutes. Thereafter, the reactor was heated to 8 ° C under agitation, and the mixture was reacted for 5 hours to obtain a solution containing 25 wt% of styrene epoxy resin [A-1]. The weight average molecular weight (Mw) of the phenylethylene storage epoxy resin [A-1] based on polystyrene was 6,000. Synthesis Examples 2 to 8 A solution containing 25 wt% of styrene epoxy resins [A-2] to [A-8] was obtained in the same manner as in the above Synthesis Example 1, except that the monomer type and amount were 2, The amounts of 2'-azobisisobutyronitrile and methylphenidene dimer were changed as shown in Table 1. The amounts of the components in Table 1 are expressed by weight (grams). The weight average molecular weight (Mw) of the styrene epoxy resin obtained in these synthesis examples in terms of polystyrene is shown in Table 1. -48- 200839444 £ S.Ex.8 1 A-8 | 34.0 1 43.0 | 1 〇16.0 | 1 〇00 〇〇6 5,500 1 S.Ex.7 A-7 40.0 1 1 40.0 | 1 20.0 1 P 〇VO ο 1 S.Ex.6 A-6 1 44.0 40.0 1 16.0 1 1 I 1 P inch p ο ο οο" S.Ex.5 < 40.0 | 27.0 1 1 L祉―丨〇10.0 〇in ο vd 5,000 S .Ex.4 A-4 1 44.0 1 40.0 | 1 1 1 16.0 | IP ο ν〇6?000 S.Ex.3 _ Μ" 50.0 1 27.0 | 1 "―17·0-1 〇νο 1 ο rn ο ¥ 15,000 S.Ex.2 A-2 ο | 38.0 1 1 1 28.0 1 30.0 1 Ο rn ο to ο ο ri S.Ex.l Al 40.0 | 27.0 | 1 丨17·0 I 16.0 1 Ο — Ο ο I Resin name _ 1 p-vinylbenzyl glycidyl ether | Ν-phenyl maleimide amide I styrene 1 benzyl methacrylate | 2-hydroxyethyl methacrylate 1 2, 2' ·Azobisisobutyronitrile 1 α-methylstyrene dimer 1 Weight average molecular weight (Mw) Frequently weird 4Π: .xws
-49- 200839444 <式(1 )所示之鹼可溶性樹脂的合成> 合成例9 200克含有前述合成例1製得之苯乙烯環氧樹脂〔A-_ 1〕、10.0克作爲不飽和單羧酸之甲基丙烯酸、0·2克對- 甲氧基酚、〇·2克溴化四丁基銨及300克丙二醇單甲基醚 乙酸酯之溶液置入燒瓶中,於120 °C溫度下反應9小時。 使得於苯乙烯環氧樹脂之每當量環氧基有1當量丙烯酸之 φ 情況下進行反應。另外,添加16.0克作爲多元酸酐之4-環己烯-1,2 -二甲酸酐,混合物於8 0 °C反應6小時。此反 應混合物以水潤洗兩次,在溶液溫度保持80°C下進行真空 濃縮。結果,得到含有20重量%鹼可溶性樹脂〔B-1〕之 溶液。鹼可溶性樹脂〔B-1〕以聚苯乙烯計之重量平均分 子量(Mw)係爲7,800。 合成例1 〇至1 8 # 依如同前述合成例9之方式製得含有20重量%鹼可溶 性樹脂〔B-2〕至〔B-10〕之溶液,不同處係苯乙烯環氧 ^ 樹脂溶液之類型、不飽和單羧酸之類型及用量及多元酸酐 〃 之類型及用量係如表2所示般變化。 此等合成例所製得之鹼可溶性樹脂以聚苯乙烯計之重 量平均分子量(Mw )係列於表2中。 -50- 200839444-49- 200839444 <Synthesis of alkali-soluble resin represented by formula (1)> Synthesis Example 9 200 g of the styrene epoxy resin [A-1] obtained in the above Synthesis Example 1 and 10.0 g as an unsaturated A solution of monocarboxylic acid methacrylic acid, 0.2 gram of p-methoxyphenol, 〇 2 g of tetrabutylammonium bromide and 300 g of propylene glycol monomethyl ether acetate was placed in a flask at 120 ° The reaction was carried out at C temperature for 9 hours. The reaction is carried out in the case where the equivalent epoxy group of the styrene epoxy resin has 1 equivalent of φ of acrylic acid. Separately, 16.0 g of 4-cyclohexene-1,2-dicarboxylic anhydride as a polybasic acid anhydride was added, and the mixture was reacted at 80 ° C for 6 hours. The reaction mixture was rinsed twice with water and concentrated under vacuum at a solution temperature of 80 °C. As a result, a solution containing 20% by weight of the alkali-soluble resin [B-1] was obtained. The alkali-soluble resin [B-1] had a weight average molecular weight (Mw) of 7,800 in terms of polystyrene. Synthesis Example 1 〇 to 18 8 A solution containing 20% by weight of an alkali-soluble resin [B-2] to [B-10] was obtained in the same manner as in the above Synthesis Example 9, except that a styrene epoxy resin solution was used. The type and amount of the unsaturated monocarboxylic acid and the type and amount of the polybasic acid anhydride are as shown in Table 2. The weight average molecular weight (Mw) of the alkali-soluble resin obtained by these synthesis examples in terms of polystyrene is shown in Table 2. -50- 200839444
oo τ-Η >< ω ζ/i B-10 | Α-8 1 00 1 1 〇\ 1 (N 〇 (N 〇 7,200 | S.Ex.17 B-9 Α-7 1 寸 οό 1 霧 1 12.0 1 (N 〇 (N c> 〇 S.Ex.16 B-8 Α-6 11.0 I 1 12.8 1 1 1 (N 〇 (N 〇 〇 t-H S.Ex.15 —Bi; Α-5 10.0 I 16.0 1 1 (N 〇 CN 〇 7,000 S.Ex.l4| B-6 Α-4 ρ r—Η r-H 1 λ r-H 1 1 ( 1 〇 (N 〇 〇 〇 〇〇 S.Ex.13 B-5 Α-1 10.0 1 I 1 〇\ <0 (N 〇 〇 〇 ϊ> S.Ex.12 B-4 Α-3 1 20.0 1 1 (N 〇 <N Ο 17,000 S.Ex.l! cn ώ Α-2 O rmmmi I ΓΠ τ—Η 1 1 (N 〇 Ο ο ο 寸。 rmmi S.Ex.10 B-2 1—( < 1 寸 οό ΟΟ 寸· 1 I (N 〇 (N Ο ο S.Ex.9 r—4 ώ τ—Η < 10.0 1 16.0 1 1 (N 〇 CN Ο 7,800 1 鹼可溶性樹脂之名稱 1 苯乙烯環氧樹脂之類型 I 甲基丙烯酸(克) 1 丙烯酸(克) 1 4-環己烯-1,2-二甲酸酐(克) 1 琥珀酸酐(克) 1 戊二酸酐(克) I 對-甲基酚(克) l 溴化四丁基銨(克) 1 重量平均分子量(Mw) 匡链啦:.xars -51 - 200839444 <鹼可溶性樹脂之對照合成例> 對照合成例1 於裝置有冷凝器及攪動器之燒瓶中,將30.0克苯乙 烯、45.0克甲基丙烯酸苄酯及15.0克甲基丙烯酸溶解於 2 00克丙二醇單甲基醚乙酸酯中。之後,將4·0克2,2’·偶 氮基雙異丁腈及6.0克α -甲基苯乙烯二聚物添加於該混合 物中,之後以氮沖洗1 5分鐘。之後,反應器於攪動下加 熱至80 °C,混合物反應5小時,以得到含有33重量%苯 乙烯環氧樹脂〔R-1〕之溶液。此鹼可溶性樹脂〔:^-1〕以 聚苯乙烯計之重量平均分子量(Mw)係爲6,000。 對照合成例2 於裝置有冷凝器及攪動器之燒瓶中,將30.0克N-苯 基順丁烯二醯亞胺、20.0克苯乙烯、35.0克甲基丙烯酸苄 酯及15.0克甲基丙烯酸溶解於200克丙二醇單甲基醚乙 酸酯中。之後,將3.0克2,2’-偶氮基雙異丁腈及5.0克 α -甲基苯乙烯二聚物添加於該混合物中,之後以氮沖洗 1 5分鐘。之後,反應器於攪動下加熱至8 0 °C,混合物反 應5小時,以得到含有33重量%苯乙烯環氧樹脂〔R-2〕 之溶液。此鹼可溶性樹脂〔R-2〕以聚苯乙烯計之重量平 均分子量(Mw)係爲12,000。 <輻射敏感性組成物之製備及評估> 實施例1 -52- 200839444 1 5重量份數包含8 0重量% C . I.顏料紅2 5 4及2 0重量 % C.I.顏料紅177之作爲著色劑(Α)的混合物、4重量份 數-以固體含量(除溶劑外之重量)計-之作爲分散劑的 Disperbyk-2000 (商標,BYK-Chemie GmbH 之產品)及 81重量份數作爲顏料用分散介質之丙二醇單甲基醚乙酸酯 係、藉珠磨機加工,製備顏料分散液。Oo τ-Η >< ω ζ/i B-10 | Α-8 1 00 1 1 〇\ 1 (N 〇(N 〇7,200 | S.Ex.17 B-9 Α-7 1 inch οό 1 fog 1 12.0 1 (N &(N c> 〇S.Ex.16 B-8 Α-6 11.0 I 1 12.8 1 1 1 (N 〇(N 〇〇tH S.Ex.15 —Bi; Α-5 10.0 I 16.0 1 1 (N 〇CN 〇 7,000 S.Ex.l4| B-6 Α-4 ρ r—Η rH 1 λ rH 1 1 ( 1 〇(N 〇〇〇〇〇S.Ex.13 B-5 Α -1 10.0 1 I 1 〇\ <0 (N 〇〇〇ϊ> S.Ex.12 B-4 Α-3 1 20.0 1 1 (N 〇<N Ο 17,000 S.Ex.l! cn ώ Α -2 O rmmmi I ΓΠ τ—Η 1 1 (N 〇Ο ο ο inch. rmmi S.Ex.10 B-2 1—( < 1 inch οό ΟΟ inch · 1 I (N 〇(N Ο ο S. Ex.9 r—4 ώ τ—Η < 10.0 1 16.0 1 1 (N 〇CN Ο 7,800 1 Name of alkali-soluble resin 1 Type of styrene epoxy resin I methacrylic acid (g) 1 Acrylic acid (g) 1 4-cyclohexene-1,2-dicarboxylic anhydride (g) 1 succinic anhydride (g) 1 glutaric anhydride (g) I p-methylphenol (g) l tetrabutylammonium bromide (g) 1 weight Average molecular weight (Mw) 匡 chain: .xars -51 - 200839444 <alkali soluble resin Comparative Synthesis Example> Comparative Synthesis Example 1 In a flask equipped with a condenser and an agitator, 30.0 g of styrene, 45.0 g of benzyl methacrylate, and 15.0 g of methacrylic acid were dissolved in 200 g of propylene glycol monomethyl ether. In the acetate, 4,0 g of 2,2'-azobisisobutyronitrile and 6.0 g of α-methylstyrene dimer were added to the mixture, followed by nitrogen purge for 15 minutes. Thereafter, the reactor was heated to 80 ° C under agitation, and the mixture was reacted for 5 hours to obtain a solution containing 33% by weight of a styrene epoxy resin [R-1]. The alkali-soluble resin [:^-1] was polyphenylene. The weight average molecular weight (Mw) of ethylene was 6,000. Comparative Synthesis Example 2 In a flask equipped with a condenser and an agitator, 30.0 g of N-phenyl maleimide, 20.0 g of styrene, 35.0 was used. Benzyl methacrylate and 15.0 g of methacrylic acid were dissolved in 200 g of propylene glycol monomethyl ether acetate. Thereafter, 3.0 g of 2,2'-azobisisobutyronitrile and 5.0 g of α-methylstyrene dimer were added to the mixture, followed by rinsing with nitrogen for 15 minutes. Thereafter, the reactor was heated to 80 ° C under agitation, and the mixture was reacted for 5 hours to obtain a solution containing 33% by weight of a styrene epoxy resin [R-2]. The alkali-soluble resin [R-2] had a weight average molecular weight (Mw) of 12,000 in terms of polystyrene. <Preparation and evaluation of radiation-sensitive composition> Example 1 - 52 - 200839444 1 5 parts by weight including 80% by weight C. I. Pigment red 2 5 4 and 20% by weight CI Pigment Red 177 Mixture of colorant (Α), 4 parts by weight - based on solid content (by weight other than solvent) - Disperbyk-2000 (trademark, product of BYK-Chemie GmbH) and 81 parts by weight as pigment A pigment dispersion liquid was prepared by a propylene glycol monomethyl ether acetate system in a dispersion medium and processed by a bead mill.
之後,100重量份數前文所製備之顏料分散液、65重 量份數作爲鹼可溶性樹脂(B )之含有鹼可溶性樹脂〔B-1 〕的溶液(樹脂濃度:20重量% ) 、1 3重量份數作爲多官 能性單體(C )之二異戊四醇六丙烯酸酯、4.3重量份數作 爲感光聚合起始劑(D)之2-甲基-(4-甲基噻吩基)-2-嗎琳-1_丙院-1-嗣及63重量份數作爲溶劑之3 -乙氧基丙酸 估 評 法 方 下 。 以 物依 成係 組物 用成 成組 形用 層成 色形。 著層 3 備色表 製著於 以之示 合得出 混所係 酯 果 乙結 估 評 輻射敏感性組成物之評估 所得之著色層形成用組成物藉旋塗器塗覆於鈉玻璃基 板上,此基板上已形成用以防止鈉離子溶離之Si02薄膜 ,基板於90°c熱板上預烘烤2分鐘,以形成具有1 .7微米 厚度之塗膜。 此具有塗膜之基板冷卻至室溫後,經由具有5至5 0 微米之不同寬度的狹縫之光罩利用高壓汞燈於1,000焦耳/ 米2曝光量下使塗膜曝照包括3 65奈米、405奈米及436 -53- 200839444 奈米波長的紫外線輻射。 之後’具有經曝光塗膜之基板使用23。(:之〇.〇4重量 %氫氧化鉀水溶液噴淋顯影1分鐘,以超純水潤洗且隨之 風乾。此外,基板於220 °C無塵烘箱中後烘烤30分鐘,以 得到具有排列於基板上之紅色條紋像素圖案的像素陣列。 耒昔光學顯微鏡觀察基板形成有像素陣列之表面,依以 下三級評級評估像素圖案邊緣是否缺損及基板上非像素圖 案之區域中是否殘留有顏料殘留物。 〔像素圖案之缺損〕 〇:寬度30微米之像素圖案中未發現缺損 △:寬度3 〇微米之像素圖案中發現某些缺損 X :寬度3 0微米之像素圖案中發現許多缺損 〔除像素圖案以外之區域中的顏料殘留物〕 〇:未發現殘留物 △:發現某些殘留物 X :發現許多殘留物。 此外,完全不脫落且完全保持原樣之最小像素圖案寬 度係評估爲可形成之最小圖案寬度(微米)。 結果顯示於表3。 實施例2及對照例1 -54- 200839444 依如同實施例1之方式製備顏料分散液,不同處係著 色劑(A )、分散劑及用於顏料之分散介質係如表3所示 般變化。 依如同實施例1之方式製備並評估著色層形成用組成 物,不同處係使用前述製備之顏料分散液且鹼可溶性樹脂 (B)、感光聚合起始劑(D)及溶劑之類型及用量及作爲 多官能性單體之二異戊四醇六丙烯酸酯的量係如表3所示 般變化。結果出示於表3。Then, 100 parts by weight of the pigment dispersion prepared above, and 65 parts by weight of the alkali-soluble resin (B) containing the alkali-soluble resin [B-1] (resin concentration: 20% by weight), 13 parts by weight a number of diisopentyl alcohol hexaacrylate as a polyfunctional monomer (C), and 4.3 parts by weight of 2-methyl-(4-methylthienyl)-2- as a photopolymerization initiator (D)琳琳-1_丙院-1-嗣 and 63 parts by weight as a solvent for the 3-ethoxypropionic acid evaluation method. The object-forming group is formed into a group forming layer. The layer 3 color setting table is formed on the soda glass substrate by using a spin coater to evaluate the composition of the radiation sensitive composition. A SiO 2 film for preventing sodium ions from being dissolved is formed on the substrate, and the substrate is prebaked on a 90 ° C hot plate for 2 minutes to form a coating film having a thickness of 0.7 μm. After the substrate with the coating film is cooled to room temperature, the coating film is exposed by a high pressure mercury lamp at a exposure angle of 1,000 J/m 2 via a mask having slits having different widths of 5 to 50 μm. 65 nm, 405 nm and 436-53-200839444 Ultraviolet radiation at nanometer wavelengths. Thereafter, the substrate having the exposed coating film was used 23. (: 〇. 〇 4% by weight aqueous potassium hydroxide solution for 1 minute, rinsed with ultrapure water and air dried. In addition, the substrate was baked in a dust-free oven at 220 ° C for 30 minutes to obtain A pixel array of red stripe pixel patterns arranged on the substrate. The surface of the substrate is formed with a pixel array, and the edge of the pixel pattern is evaluated according to the following three-level rating, and whether the pigment remains in the non-pixel pattern area on the substrate Residues [Defects in Pixel Patterns] 〇: No defects were found in the pixel pattern of width 30 μm. △: Some defects were found in the pixel pattern of width 3 〇 micron. X: Many defects were found in the pixel pattern of width of 30 μm. Pigment residue in areas other than the pixel pattern 〇: No residue found △: Some residue X was found: Many residues were found. In addition, the minimum pixel pattern width which did not fall off completely and remained intact was evaluated as being formed. The minimum pattern width (micrometer). The results are shown in Table 3. Example 2 and Comparative Example 1 - 54 - 200839444 Prepared in the same manner as in Example 1. The pigment dispersion liquid, the coloring agent (A) at different points, the dispersing agent, and the dispersion medium for the pigment were changed as shown in Table 3. The composition for forming a colored layer was prepared and evaluated in the same manner as in Example 1, and the difference was obtained. The pigment dispersion liquid prepared as described above and the type and amount of the alkali-soluble resin (B), the photosensitive polymerization initiator (D) and the solvent, and the amount of diisoprolol hexaacrylate as the polyfunctional monomer are as follows. The changes are shown in Table 3. The results are shown in Table 3.
-55- 200839444 e漱 C.Ex.l | 紅色顏料 1 BYK-2000 | PGMEA | r-H ώ 〇 起始劑A 1 寸 3MBA 1 00 00 X X Ex.2 綠色顏料 BYK-2001 3MBA Β-4 〇 寸 r—ί 起始劑B 〇 r4 3EPE On 〇 〇 Ex.l 紅色顏料 BYK-2000 PGMEA ι-Ή ώ yn vo cn Η 起始劑A cn 3EPE cn Ό 〇 <] 00 著色劑(A)之類型 分散液之類型 用於顔料之分散介質的類型 類型 用量 用量 類型 用量 類型 用量 殘留物存在或不存在 邊緣之缺損存在或不存在 可形成之圖案尺寸(微米) 鹼可溶性樹S旨(Β) 多官能性單體(C) 感光聚合起始劑 (D) 溶劑 顏料分散液 輻射敏感性組成物 評估結果 -56- 200839444 表3中組份之縮寫係表示下列者。 (A )著色劑: 紅色顏料:8〇重量% C.I·顏料紅254及20重量% C.I. 顏料紅177之混合物 綠色顏料:60重量% C.I.顏料綠36及40重量% C.I. 顏料黃1 5 0之混合物 分散劑: BYK-2000 : Disperbyk-2000 ( BYK-Chemie GmbH 之 產品商標) BYK-200 1 : Disperbyk-2001 (BYK-Chemie GmbH 之 產品商標) 顏料用之分散介質: PGMEA :丙二醇單甲基醚乙酸酯 3MBA :乙酸3-甲氧基丁酯 (D )感光聚合起始劑: 起始劑 A : 2-甲基-(4_甲基噻吩基)-2-嗎啉-11-丙 院-1 -嗣 起始劑B ·乙嗣-1 -〔 9 -乙基-6 -〔 2 -甲基-4 - ( 2,2 - 一·甲 基-1,3-二氧戊環)甲氧基苯甲醯基〕-9.H·-味唑-3-基〕-1-(〇-乙醯肟) 溶劑= 3EPE : 3-乙氧基丙酸乙酯 3MBA :乙酸3-甲氧基丁酯 表3中組份之量係以重量份數表示。 -57- 200839444 製備顏料分散液之分散劑係以溶液形式添加,表3中 分散劑之量係以固體含量(除溶劑外之重量)表示。 鹼可溶性樹脂(B )係以含有前述合成例所製備之鹼 可溶性樹脂的溶液形式添加,而表3中鹼可溶性樹脂之量 係溶液之量。 實施例3 φ 2 0重量份數作爲著色劑(A )的碳黑' 4重量份數作 爲分散劑的 Disperbyk-167 (商標,BYK-Chemie GmbΗ 之產品)及76重量份數作爲顏料用分散介質之乙酸3 -甲 氧基丁酯係藉珠磨機加工,製備顏料分散液。 之後’ 100重量份數前文所製備之顏料分散液、52.5 重量份數作爲鹼可溶性樹脂(Β )之含有驗可溶性樹脂〔 Β · 2〕的溶液(樹脂濃度:2 0重量% )、作爲多官能性單 體(C)之5.6重量份數異戊四醇四丙燒酸酯及2.4重量份 • 數二異戊四醇六丙烯酸酯、3.7重量份數作爲感光聚合起 始劑(D)之乙酬-1-〔 9 -乙基-6-〔 6 -甲基·4- ( 2,2 -二甲 • 基-1,3-二氧戊環)甲氧基苯甲醯基〕-9.Η·-咔唑-3-基〕-卜 一 (0 -乙醯肟)及76重量份數作爲溶劑之丙二醇單甲基醚 乙酸酯混合以製備著色層形成用組成物。 所得之著色層形成用組成物依實施例1方法進行評估 ,不同處係所形成之塗膜的厚度係爲1 .〇微米。評估結果 出示於表4。 -58- 200839444 實施例4至10及對照例2 於實施例4至6、8至10及對照例2中,顏料分散液 係依如同實施例1之方式製備。實施例7中,依如同眚施 例3之方式製備顏料分散液,不同處係使用丙二醇單甲基 醚乙酸酯作爲顏料用之分散介質。 依如同實施例3之方式製備並評估著色層形成用組成 物,不同處係使用前述製備之顏料分散液且鹼可溶性樹脂 (B )及溶劑之類型及用量係如表4所示般變化且使用表 4所示之量之表4所示多官能性單體及感光聚合起始劑作 爲多官能性單體(C )及感光聚合起始劑(D )。結果出示 於表4。-55- 200839444 e漱C.Ex.l | Red Pigment 1 BYK-2000 | PGMEA | rH ώ 〇 Starter A 1 inch 3MBA 1 00 00 XX Ex.2 Green Pigment BYK-2001 3MBA Β-4 〇 inch r —ί Initiator B 〇r4 3EPE On 〇〇Ex.l Red pigment BYK-2000 PGMEA ι-Ή ώ yn vo cn Η Starting agent A cn 3EPE cn Ό 〇<] 00 Colorant (A) type dispersion Type of liquid Type of dispersing medium used for pigments Types Dosage Type Dosage Type Dosage Residues Presence or absence of edge defects Exist or absence of formable size (micron) Alkali soluble tree S (Β) Polyfunctional Monomer (C) Photopolymerization Initiator (D) Solvent Pigment Dispersion Radiation Sensitive Composition Evaluation Results -56- 200839444 The abbreviations of the components in Table 3 indicate the following. (A) Colorant: Red pigment: 8 〇 wt% CI·Pigment red 254 and 20% by weight CI Pigment red 177 mixture Green pigment: 60% by weight CI pigment green 36 and 40% by weight CI Pigment yellow 1 50 mixture Dispersant: BYK-2000 : Disperbyk-2000 (trademark of BYK-Chemie GmbH) BYK-200 1 : Disperbyk-2001 (trademark of BYK-Chemie GmbH) Dispersion medium for pigments: PGMEA : propylene glycol monomethyl ether B Acid ester 3MBA: 3-methoxybutyl acetate (D) photopolymerization initiator: initiator A: 2-methyl-(4-methylthienyl)-2-morpholine-11-propyl- 1 -嗣 starter B · acetam-1 -[ 9 -ethyl-6 -[ 2 -methyl-4 - ( 2,2 - monomethyl-1,3-dioxolan) methoxy Benzobenzyl]-9.H--oxazol-3-yl]-1-(anthracene-ethene) Solvent = 3EPE: 3-Ethyloxypropanoate 3MBA: 3-methoxyacetic acid The amount of the components in the butyl ester table 3 is expressed in parts by weight. -57- 200839444 The dispersant for preparing the pigment dispersion is added as a solution, and the amount of the dispersant in Table 3 is expressed as a solid content (weight other than the solvent). The alkali-soluble resin (B) was added as a solution containing the alkali-soluble resin prepared in the above Synthesis Example, and the amount of the alkali-soluble resin in Table 3 was the amount of the solution. Example 3 φ 20 parts by weight as carbon black of the colorant (A) '4 parts by weight Disperbyk-167 (trademark, product of BYK-Chemie Gmb®) and 76 parts by weight as a dispersing agent as a dispersion medium for pigments The 3-methoxybutyl acetate was processed by a bead mill to prepare a pigment dispersion. Then, '100 parts by weight of the pigment dispersion prepared above, 52.5 parts by weight as a solution of the alkali-soluble resin (Β) containing the soluble resin [Β · 2] (resin concentration: 20% by weight), as a polyfunctional 5.6 parts by weight of the monomer (C), isopentitol tetrapropionate, 2.4 parts by weight, diisopentaerythritol hexaacrylate, and 3.7 parts by weight as the photopolymerization initiator (D) Revenue-1-[9-ethyl-6-[6-methyl·4-(2,2-dimethyl-l-1,3-dioxolan)methoxybenzylidene]-9. Η·-carbazol-3-yl]-b-(0-acetamidine) and 76 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a composition for forming a colored layer. The obtained composition for forming a color layer was evaluated by the method of Example 1, and the thickness of the coating film formed at different points was 1. 〇 micrometer. The results of the evaluation are shown in Table 4. -58- 200839444 Examples 4 to 10 and Comparative Example 2 In Examples 4 to 6, 8 to 10 and Comparative Example 2, a pigment dispersion liquid was prepared in the same manner as in Example 1. In Example 7, a pigment dispersion liquid was prepared in the same manner as in Example 3, except that propylene glycol monomethyl ether acetate was used as a dispersion medium for the pigment. The composition for forming a colored layer was prepared and evaluated in the same manner as in Example 3, except that the pigment dispersion prepared above was used, and the type and amount of the alkali-soluble resin (B) and the solvent were changed as shown in Table 4 and used. The polyfunctional monomer and the photopolymerization initiator shown in Table 4 in the amounts shown in Table 4 were used as the polyfunctional monomer (C) and the photopolymerization initiator (D). The results are shown in Table 4.
-59- 200839444 寸撇 1 C.Ex.2 1 | 32.0 | 寸 (N 1 卜 cn 3EPE j <] X Ex. 10 B-10 61.7 CN 1 1 卜 ΓΠ 3MBA 68.6 〇 〇 Ex.9 B-3 1 52,5 j 寸 (N VO in 1 〇 rn 3MBA 〇 <1 Ex. 8 B-9 52.5 寸 (N 1 卜 cn 3MBA 〇 〇 Ex.7 B-8 52.5 1 Ο 00 麵 卜 rn 3MBA VO 〇 〇 Ex. 6 1 B^7 寸 (N VO 〇 r—Η <Ν 3EPE VO 〇 〇 Ex.5 B-6 |46·5」 m cK 1 1 卜 rn 1 3MBA 1 T—Η 00 〇 〇 Εχ·4 _1 ώ 1 52.5 1 寸 ri Ό … 1 卜 ΓΛ Imba 1_ VO 〇 〇 卜 | Ex.3 1 B-2 ] 1 52.5 1 寸 (N νο 1 卜 rn 1 3MBA 1 vo 〇 〇 類型 用量 多官能性單體(c) 二異戊四醇六丙烯酸酯之量 ! 異戊四醇六丙烯酸酯之量 感光聚合起始劑(D) 起始劑Α之量 起始劑B之量 丨類型 用量 殘留物存在或不存在 ί 邊緣缺損存在或不存在 可形成之圖案尺寸(微米) 鹼可溶性樹脂(B) 溶劑 輻射敏感 性組成物 評估結果 f-義1 : ΘΗϋ 二政㈣*..·Χ3 -60 - 200839444 表4中感光聚合起始劑(D )及溶劑之縮寫係表示如 同表3所示者。 此外,表4中之組份的量係以重量份數表示。 鹼可溶性樹脂(B )係以前述合成例所製備含有鹼可 溶性樹脂之溶液的形式添加,表4中鹼可溶性樹脂之量係 爲溶液之量。 如前文所述,本發明輻射敏感性組成物可形成即使在 低曝光下圖案邊緣仍不缺損且無側蝕之精細圖案,且可適 用於形成包含構成濾色器之像素的著色層或係爲黑基質之 著色層,因爲顯影時不會殘留不溶物且圖案邊緣不形成浮 渣0-59- 200839444 inch 撇 1 C.Ex.2 1 | 32.0 | inch (N 1 卜 3EPE j <] X Ex. 10 B-10 61.7 CN 1 1 ΓΠ 3MBA 68.6 〇〇Ex.9 B-3 1 52,5 j inches (N VO in 1 〇rn 3MBA 〇<1 Ex. 8 B-9 52.5 inches (N 1 卜 3MBA 〇〇Ex.7 B-8 52.5 1 Ο 00 face rn 3MBA VO 〇 〇Ex. 6 1 B^7 inch (N VO 〇r—Η <Ν 3EPE VO 〇〇Ex.5 B-6 |46·5” m cK 1 1 卜 rn 1 3MBA 1 T—Η 00 〇〇Εχ · 4 _1 ώ 1 52.5 1 inch ri Ό ... 1 ΓΛ Imba 1_ VO 〇〇 | | Ex.3 1 B-2 ] 1 52.5 1 inch (N νο 1 rb 1 3MBA 1 vo 〇〇 type usage polyfunctionality Monomer (c) Amount of diisopentyltetraol hexaacrylate! Amount of pentaerythritol hexaacrylate photosensitive polymerization initiator (D) Starting agent Α amount of initiator B amount 丨 type amount residue Presence or absence ί Edge defect presence or absence of pattern size that can be formed (micron) Alkali-soluble resin (B) Solvent radiation sensitivity composition evaluation result f-yi 1 : ΘΗϋ II (4) *..·Χ3 -60 - 200839444 Photosensitive polymerization in Table 4 The abbreviations of the initiator (D) and the solvent are shown in Table 3. In addition, the amounts of the components in Table 4 are expressed in parts by weight. The alkali-soluble resin (B) is prepared by the above-mentioned synthesis example. In the form of a solution of an alkali-soluble resin, the amount of the alkali-soluble resin in Table 4 is the amount of the solution. As described above, the radiation-sensitive composition of the present invention can form a pattern edge without defects and no side even under low exposure. a fine pattern of etching, and is applicable to forming a coloring layer containing a pixel constituting a color filter or a coloring layer which is a black matrix because no insoluble matter remains during development and no scum is formed at the edge of the pattern.
-61 --61 -
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JP5326420B2 (en) * | 2008-08-12 | 2013-10-30 | Jsr株式会社 | Radiation-sensitive composition for forming light-shielding film, light-shielding film for solid-state image sensor, and solid-state image sensor |
JP5644992B2 (en) * | 2008-09-05 | 2014-12-24 | Jsr株式会社 | Colored radiation-sensitive composition, color filter, and color liquid crystal display element |
JP2010145857A (en) * | 2008-12-19 | 2010-07-01 | Mitsubishi Chemicals Corp | Colored resin composition for color filter, color filter, liquid crystal display, and organic el display |
JP2010145858A (en) * | 2008-12-19 | 2010-07-01 | Mitsubishi Chemicals Corp | Colored resin composition for color filter, color filter, liquid crystal display, and organic el display |
JP2010191119A (en) * | 2009-02-17 | 2010-09-02 | Jsr Corp | Radiation-sensitive composition for forming color layer, color filter and solid-state imaging device |
JP5482996B2 (en) * | 2009-09-17 | 2014-05-07 | Jsr株式会社 | Coloring composition, color filter and color liquid crystal display element |
CN103149799A (en) * | 2011-12-07 | 2013-06-12 | 三菱化学株式会社 | Colored resin composition, color filter, liquid crystal display and organic el display device |
KR102006751B1 (en) * | 2012-12-11 | 2019-08-02 | 제이에스알 가부시끼가이샤 | Radiation-sensitive resin composition, cured film for display device, method for forming the cured film for display device, and display device |
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JP4496818B2 (en) * | 2004-03-30 | 2010-07-07 | Jsr株式会社 | Radiation sensitive composition for color filter, color filter, and color liquid crystal display device |
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