TWI764041B - Compound, colorant composition, photoresist, color filter and display device - Google Patents
Compound, colorant composition, photoresist, color filter and display deviceInfo
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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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
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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Abstract
Description
本申請案主張於2018年09月06日提交至韓國智慧財產局的韓國專利申請案第10-2018-0106491號的申請日的利益,其內容全部包含於本說明書。 This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0106491 filed with the Korea Intellectual Property Office on September 6, 2018, the entire contents of which are included in this specification.
本說明書是有關於一種化合物、著色劑組成物、光阻、彩色濾光片以及顯示裝置。 This specification is about a compound, a colorant composition, a photoresist, a color filter, and a display device.
目前,為了實現彩色濾光片,通常應用將顏料用作著色劑的顏料分散法。但是顏料分散液的情況,顏料以粒子狀態存在而不僅使光散射,而且因顏料的微細化而使顏料表面積急劇地增加,因藉此引起的分散穩定性的惡化而生成不均勻的顏料粒子。因此,為了達成最近要求的高亮度、高對比度及高解析度,最近研究了使用染料代替顏料作為著色劑。 Currently, in order to realize a color filter, a pigment dispersion method using a pigment as a colorant is generally applied. However, in the case of a pigment dispersion liquid, the pigment exists in a particle state and not only scatters light, but also rapidly increases the surface area of the pigment due to the miniaturization of the pigment, and the resulting deterioration of the dispersion stability results in the generation of non-uniform pigment particles. Therefore, in order to achieve the high brightness, high contrast, and high resolution recently required, the use of dyes as colorants instead of pigments has recently been studied.
通常,染料與顏料相比具有透射度高的優點。但是與顏料相比具有耐熱性不足的缺點。另外,與現有顏料相比,對有機 溶劑的溶解度佳,因而具有耐化學性不足的缺點。 Generally, dyes have the advantage of high transmittance compared to pigments. However, it has the disadvantage of insufficient heat resistance compared with pigments. In addition, compared with existing pigments, organic The solubility of the solvent is good, so it has the disadvantage of insufficient chemical resistance.
[專利文獻1]日本公開文獻 特開平9-87534 [Patent Document 1] Japanese Patent Publication No. Hei 9-87534
本說明書欲提供一種化合物、著色劑組成物、光阻、彩色濾光片以及顯示裝置。 This specification intends to provide a compound, a colorant composition, a photoresist, a color filter, and a display device.
本說明書的一實施形態提供一種化合物,包含:三芳基甲烷染料單體;(甲基)丙烯酸單體;以及由下述化學式1表示的結構。 One embodiment of the present specification provides a compound comprising: a triarylmethane dye monomer; a (meth)acrylic monomer; and a structure represented by the following Chemical Formula 1.
在所述化學式1中,意指與其他單體或鍵結部連接的部分,X'為O或NH,L1及L2彼此相同或不同,分別獨立地為直接鍵結、經取代或未經取代的伸烷基、-C(=O)-、或-L3-O(C=O)-, L3為經取代或未經取代的伸烷基,R1至R3彼此相同或不同,分別獨立地為氫、羥基、經取代或未經取代的烷基,r2為0至4的整數,在r2為2或大於2的情況下,R2彼此相同或不同,r3為0至5的整數,在r3為2或大於2的情況下,R3彼此相同或不同。 In the chemical formula 1, Means a moiety connected to other monomers or linkages, X' is O or NH, L1 and L2 are the same or different from each other, and are each independently a direct bond, substituted or unsubstituted alkylene, -C (=O)-, or -L3-O(C=O)-, L3 is a substituted or unsubstituted alkylene, R1 to R3 are the same or different from each other, and are independently hydrogen, hydroxyl, substituted or Unsubstituted alkyl, r2 is an integer from 0 to 4, where r2 is 2 or greater, R2 is the same or different from each other, r3 is an integer from 0 to 5, where r3 is 2 or greater , R3 are the same or different from each other.
本說明書的一實施形態提供一種著色劑組成物,包含:所述化合物;黏合劑樹脂;多官能性單體;光起始劑;以及溶劑。 An embodiment of the present specification provides a colorant composition comprising: the compound; a binder resin; a multifunctional monomer; a photoinitiator; and a solvent.
本說明書的一實施形態提供一種利用所述著色劑組成物製備而成的光阻。 An embodiment of the present specification provides a photoresist prepared using the colorant composition.
本說明書的一實施形態提供一種包含所述光阻的彩色濾光片。 An embodiment of the present specification provides a color filter including the photoresist.
本說明書的一實施形態提供一種包含所述彩色濾光片的顯示裝置。 An embodiment of the present specification provides a display device including the color filter.
根據本說明書的一實施形態的化合物在著色劑組成物中可用作顏色材料,在利用所述著色劑組成物製備彩色濾光片的情況下,耐化學特性及耐熱性優異。 The compound according to one embodiment of the present specification can be used as a color material in a colorant composition, and when a color filter is produced using the colorant composition, it is excellent in chemical resistance and heat resistance.
以下,針對本說明書,更詳細地進行說明。 Hereinafter, this specification will be described in more detail.
在本說明書中,在記載為某部件位於其他部件「上」時,該情況不僅包含某部件與其他部件相接的情況,而且亦包含兩部件之間存在又一部件的情況。 In this specification, when a certain member is described as being "on" another member, the case includes not only the case where a certain member is in contact with the other member, but also the case where another member exists between the two members.
在本說明書中,在記載為某部分「包含」某構成要素時,只要無特別相反的記載,則該情況意指並不排除其他構成要素,可更包含其他構成要素。 In this specification, when it is described that a part "includes" a certain component, unless otherwise stated, this does not mean that other components are not excluded, and other components may be further included.
在本說明書中,意指與其他單體、其他取代基或鍵結部連接的部分。 In this manual, Means moieties linked to other monomers, other substituents or linkages.
在本說明書中,意指與其他鍵結部連接的部分。 In this manual, Means a part that is connected to other bond parts.
在本說明書中,所述連接的部分的「連接」可意指原子間以單鍵或雙鍵連接。 In the present specification, the "connection" of the connected moiety may mean that atoms are connected by a single bond or a double bond.
所述鍵結部意指化學式或化學結構間連接的部分。 The bond means a part of a link between chemical formulas or chemical structures.
在本說明書中,「單體」為單量體或單位體,且意指形成高分子的單位分子或重覆結構。 In this specification, a "monomer" is a monomer or a unit, and means a unit molecule or a repeating structure that forms a polymer.
在本說明書中,由化學式1表示的結構可意指具有由化學式1表示的結構的單體。 In the present specification, the structure represented by Chemical Formula 1 may mean a monomer having the structure represented by Chemical Formula 1.
根據本說明書的一實施形態,提供一種包含由所述化學式1表示的結構的化合物。 According to an aspect of this specification, the compound containing the structure represented by the said chemical formula 1 is provided.
根據本說明書的一實施形態的化合物藉由包含三芳基甲烷染料單體、(甲基)丙烯酸單體、以及由所述化學式1表示的結構,從而可提高耐熱性及耐化學性。具體而言,在向三芳基甲烷染料投入由所述化學式1表示的結構的情況,在進行曝光製程時由所述化學式1表示的結構促進自由基(Radical)反應,與未投入由所述化學式1表示的結構時相比,可使著色組成物內的黏合劑樹脂、所述化合物、多官能性單體的鍵結更活化,膜的硬化度變高,從而耐熱性及耐化學性得到提高。 The compound according to one embodiment of the present specification can improve heat resistance and chemical resistance by including a triarylmethane dye monomer, a (meth)acrylic monomer, and the structure represented by the chemical formula 1. Specifically, when the structure represented by the chemical formula 1 is added to the triarylmethane dye, the structure represented by the chemical formula 1 promotes a radical (Radical) reaction during the exposure process, and the structure represented by the chemical formula 1 is not added to the chemical formula. Compared with the structure represented by 1, the bond between the binder resin, the compound, and the multifunctional monomer in the coloring composition can be more activated, the degree of hardening of the film can be increased, and the heat resistance and chemical resistance can be improved. .
由所述化學式1表示的結構具體而言較佳為二苯甲酮甲基丙烯酸酯(benzophenone methacrylate,BPMA)單體,但並不限定於此。 Specifically, the structure represented by the chemical formula 1 is preferably, but not limited to, a benzophenone methacrylate (BPMA) monomer.
由所述化學式1表示的化合物的取代基的例示在下文中說明,但並不限定於此。 Examples of substituents of the compound represented by the chemical formula 1 are described below, but are not limited thereto.
在本說明書中,「經取代或未經取代」的用語意指被選自包含氘、鹵素基、腈基、硝基、羥基(-OH)、羰基、酯基、羧基(-COOH)、醯亞胺基、醯胺基、陰離子性基、烷氧基、烷基、環烷基、烯基、環烯基、芳烷基、膦基、磺酸鹽基、胺基、芳基、雜芳基、矽基、硼基、丙烯醯基、丙烯酸酯基、醚基、包含N、O、S或P原子中的一個以上的雜環基及陰離子性基的群組中的一個以上的取代基取代、或者不具有任何取代基。 In this specification, the term "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxyl (-OH), carbonyl, ester, carboxyl (-COOH), acyl Imino, amide, anionic, alkoxy, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aralkyl, phosphino, sulfonate, amine, aryl, heteroaryl One or more substituents in the group of a group, a silicon group, a boron group, an acryl group, an acrylate group, an ether group, a heterocyclic group containing one or more of N, O, S, or P atoms, and an anionic group substituted or without any substituent.
在本說明書中,作為鹵素基的例子,有氟、氯、溴或碘。 In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
在本說明書中,所述烷基可為直鏈或分支鏈,碳個數並 不特別限定,所述烷基的碳個數可為1至30。根據又一實施形態,所述烷基的碳個數為1至20。根據又一實施形態,所述烷基的碳個數為1至10。作為烷基的具體例子,有甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、正己基、正庚基、及正辛基等,但並不限定於此。 In this specification, the alkyl group can be straight or branched, and the number of carbons is different. Not particularly limited, the carbon number of the alkyl group may be 1 to 30. According to yet another embodiment, the number of carbons in the alkyl group is 1 to 20. According to yet another embodiment, the number of carbons in the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl etc., but not limited to this.
在本說明書中,環烷基並不特別限定,但較佳為碳個數為3至30,特別是較佳為環戊基、環己基,但並不限定於此。 In the present specification, the cycloalkyl group is not particularly limited, but preferably has a carbon number of 3 to 30, and particularly preferably is a cyclopentyl group and a cyclohexyl group, but is not limited thereto.
在本說明書中,伸烷基意指在烷烴(alkane)中有兩個鍵結位置的基團。所述烷烴適用對上述的烷基的說明。所述伸烷基可為直鏈、分支鏈或環狀鏈。伸烷基的碳個數並不特別限定,例如碳個數可為1至30。另外,碳個數可為1至20,且碳個數可為1至10。 In this specification, an alkylene group means a group having two bonding positions in an alkane. For the alkane, the description for the above-mentioned alkyl group applies. The alkylene group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkylene group is not particularly limited, and for example, the number of carbon atoms may be 1 to 30. In addition, the number of carbons may be 1 to 20, and the number of carbons may be 1 to 10.
在本說明書中,環烷基並不特別限定,但根據一實施形態,所述環烷基的碳個數為3至30。根據又一實施形態,所述環烷基的碳個數為3至20。根據又一實施形態,所述環烷基的碳個數為3至6。具體而言,有環丙基、環丁基、環戊基、環己基、環庚基、環辛基等,但並不限定於此。 In this specification, the cycloalkyl group is not particularly limited, but according to one embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 30. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, although there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., it is not limited to these.
在本說明書中,芳基並不特別限定,但較佳為其碳個數為6至60,且可為單環式芳基或多環式芳基。根據一實施形態,所述芳基的碳個數為6至30。根據一實施形態,所述芳基的碳個數為6至20。作為單環式芳基,所述芳基可為苯基、聯苯基、聯三苯基等,但不限定於此。作為所述多環式芳基,可為萘基、蒽 基、茚基、菲基、芘基、苝基、三苯基、基、芴基等,但不限定於此。 In this specification, the aryl group is not particularly limited, but preferably has a carbon number of 6 to 60, and may be a monocyclic aryl group or a polycyclic aryl group. According to an embodiment, the carbon number of the aryl group is 6 to 30. According to an embodiment, the carbon number of the aryl group is 6 to 20. As the monocyclic aryl group, the aryl group may be phenyl, biphenyl, triphenyl, etc., but is not limited thereto. As the polycyclic aryl group, there may be naphthyl, anthracenyl, indenyl, phenanthryl, pyrenyl, perylene, triphenyl, group, fluorene group, etc., but not limited to this.
在本說明書中,所述雜環基是包含O、N或S作為異種原子的雜環基,碳個數並不特別限定,但碳個數為2至30,具體而言碳個數為2至20。作為雜環基的例子,有噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、聯吡啶基、三嗪基、吖啶基(acridyl)、噠嗪基、喹啉基、異喹啉基、吲哚基、哢唑基、苯並噁唑基、苯並咪唑基、苯並噻唑基、苯並哢唑基、苯並噻吩基、二苯並噻吩基、苯並呋喃基及二苯並呋喃基等,但並不僅限定於此。 In this specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the number of carbons is not particularly limited, but the number of carbons is 2 to 30, specifically, the number of carbons is 2 to 20. As examples of the heterocyclic group, there are thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridinyl (acridyl), pyridazinyl, quinolinyl, isoquinolinyl, indolyl, oxazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzothiophene group, dibenzothienyl group, benzofuranyl group, dibenzofuranyl group, etc., but not limited thereto.
在本說明書中,除雜芳基為芳香族以外,可應用有關於上述的雜環基的說明。 In this specification, the description about the above-mentioned heterocyclic group is applicable except that the heteroaryl group is aromatic.
在本說明書中,「三芳基甲烷染料」的「芳基」意指可應用對所述芳基的說明及/或對所述雜環基的說明。 In this specification, the "aryl group" of the "triarylmethane dye" means that the description of the aryl group and/or the description of the heterocyclic group can be applied.
在本說明書中,所述烷氧基可為直鏈或分支鏈,碳個數並不特別限定,但可為1至30,具體而言可為1至20,更具體而言可為1至10。 In this specification, the alkoxy group may be a straight chain or a branched chain, and the number of carbons is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 20. 10.
在本說明書中,胺基可選自由-NH2、烷基胺基、N-烷基芳基胺基、芳基胺基、N-芳基雜芳基胺基、N-烷基雜芳基胺基及雜芳基胺基所組成的群組中,且碳個數並不特別限制,但較佳為1至30個。作為所述胺基的追加的例子,有甲胺基、二甲胺基、乙胺基、二乙胺基、苯胺基、萘胺基、聯苯胺基、蒽基胺基、9-甲 基-蒽基胺基、二苯胺基、N-苯基萘胺基、二甲苯基胺基、N-苯基甲苯基胺基、三苯胺基、N-苯基聯苯胺基、N-苯基萘胺基、N-聯苯基萘胺基、N-萘芴基胺基、N-苯基菲胺基、N-聯苯基菲胺基、N-苯基芴基胺基、N-苯基三聯苯胺基、N-菲基芴基胺基、N-聯苯基芴基胺基等,但並不限定於此。 In this specification, the amine group can be selected from -NH 2 , alkylamine group, N-alkylarylamine group, arylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group In the group formed by the amino group and the heteroarylamine group, the number of carbons is not particularly limited, but preferably 1 to 30. Examples of the addition of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, aniline, naphthylamino, benzidine, anthracenylamino, 9-methyl- Anthracenylamine, diphenylamine, N-phenylnaphthylamine, xylylamine, N-phenyltolylamine, triphenylamine, N-phenylbenzidine, N-phenylnaphthylamine base, N-biphenyl naphthylamino, N-naphthyl fluorenyl amino, N-phenylphenanthrene amino, N-biphenyl phenanthrene amino, N-phenylfluorenyl amino, N-phenyl triple Anilino group, N-phenanthrenylfluorenylamino group, N-biphenylfluorenylamino group, etc., but not limited thereto.
在本說明書中,陰離子性基與所述三芳基甲烷染料單體具有化學鍵,且所述化學鍵可意指離子鍵。所述陰離子性基並不特別限定,例如,可應用在美國專利第7,939,644號、日本特開第2006-003080號、日本特開第2006-001917號、日本特開第2005-159926號、日本特開第2007-7028897號、日本特開第2005-071680號、韓國申請公開第2007-7000693號、日本特開第2005-111696號、日本特開第2008-249663號、及日本特開第2014-199436中所記載的陰離子。 In the present specification, an anionic group has a chemical bond with the triarylmethane dye monomer, and the chemical bond may mean an ionic bond. The anionic group is not particularly limited, for example, it can be applied to US Patent No. 7,939,644, Japanese Patent Laid-Open No. 2006-003080, Japanese Patent Laid-Open No. 2006-001917, Japanese Patent Laid-Open No. 2005-159926, Japanese Patent Laid-Open No. 2005-159926 Laid-Open No. 2007-7028897, Japanese Laid-Open No. 2005-071680, Korean Application Laid-Open No. 2007-7000693, Japanese Laid-Open No. 2005-111696, Japanese Laid-Open No. 2008-249663, and Japanese Laid-Open No. 2014- Anions described in 199436.
作為所述陰離子性基的具體例子,有三氟甲烷磺酸根陰離子、雙(三氟甲基磺醯基)醯胺陰離子、雙三氟甲烷磺醯亞胺陰離子、雙全氟乙基磺醯亞胺陰離子、四苯基硼酸根陰離子、四(4-氟苯基)硼酸鹽、四(五氟苯基)硼酸鹽、三三氟甲烷磺醯基甲基化物、SO3 -、CO2 -、SO2N-SO2CF3、SO2N-SO2CF2CF3、鹵素基例如氟基、碘基、氯基等,但並不僅限定於此。 Specific examples of the anionic group include trifluoromethanesulfonate anion, bis(trifluoromethylsulfonyl)imide anion, bistrifluoromethanesulfonimide anion, and bisperfluoroethylsulfonimide anion , tetraphenyl borate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, trifluoromethanesulfonyl methide, SO 3 - , CO 2 - , SO 2 N - SO 2 CF 3 , SO 2 N - SO 2 CF 2 CF 3 , halogen groups such as fluorine group, iodine group, chlorine group, etc., but not limited thereto.
在本說明書中,陰離子性基可以其自身具有陰離子,或者可與其他陽離子一併以錯合化合物的形態存在。因此,根據經取代的陰離子性基的個數,本發明的化合物的分子整體的電荷之 和可不同。在本發明的化合物的一個胺基中具有陽離子,因此,分子整體的電荷之和可具有從自經取代的陰離子性基的個數減去1所得的值的陰離子至0的值。 In the present specification, the anionic group may have an anion by itself, or may exist in the form of a complex compound together with other cations. Therefore, depending on the number of substituted anionic groups, the total molecular charge of the compound of the present invention is and can be different. Since the compound of the present invention has a cation in one amine group, the sum of the charges of the entire molecule can have a value from an anion to 0 from a value obtained by subtracting 1 from the number of substituted anionic groups.
在本說明書中,「(甲基)丙烯酸((meth)acrylic acid)」表示選自由丙烯酸及甲基丙烯酸所組成的群組中的至少一種。「(甲基)丙烯酸((metha)acrylic acid)」的表述也具有相同的含義。 In this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The expression "(meth)acrylic acid" also has the same meaning.
在本說明書中,(甲基)丙烯酸((meth)acrylic acid)或(甲基)丙烯酸((metha)acrylic acid)可由甲基丙烯酸(methacrylic acid)表示。 In this specification, (meth)acrylic acid or (meth)acrylic acid may be represented by methacrylic acid.
本說明書的一實施形態提供一種化合物,包含:三芳基甲烷染料單體;(甲基)丙烯酸單體;以及由下述化學式1表示的結構。 One embodiment of the present specification provides a compound comprising: a triarylmethane dye monomer; a (meth)acrylic monomer; and a structure represented by the following Chemical Formula 1.
在所述化學式1中,意指與其他單體或鍵結部連接的部分,X'為O或NH,L1及L2彼此相同或不同,分別獨立地為直接鍵結、經取代或未經取代的伸烷基、-C(=O)-、或-L3-O(C=O)-, L3為經取代或未經取代的伸烷基,R1至R3彼此相同或不同,分別獨立地為氫、羥基、經取代或未經取代的烷基,r2為0至4的整數,在r2為2或大於2的情況下,R2彼此相同或不同,r3為0至5的整數,在r3為2或大於2的情況下,R3彼此相同或不同。 In the chemical formula 1, Means a moiety connected to other monomers or linkages, X' is O or NH, L1 and L2 are the same or different from each other, and are each independently a direct bond, substituted or unsubstituted alkylene, -C (=O)-, or -L3-O(C=O)-, L3 is a substituted or unsubstituted alkylene, R1 to R3 are the same or different from each other, and are independently hydrogen, hydroxyl, substituted or Unsubstituted alkyl, r2 is an integer from 0 to 4, where r2 is 2 or greater, R2 is the same or different from each other, r3 is an integer from 0 to 5, where r3 is 2 or greater , R3 are the same or different from each other.
在本說明書的一實施形態中,X'為O。 In one embodiment of this specification, X' is O.
在本說明書的一實施形態中,X'為NH。 In one embodiment of this specification, X' is NH.
在本說明書的一實施形態中,L1為直接鍵結、經取代或未經取代的伸烷基、或-C(=O)-。 In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted alkylene, or -C(=O)-.
在本說明書的一實施形態中,L1為直接鍵結、碳個數為1至30的經取代或未經取代的伸烷基、或-C(=O)-。 In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted alkylene having 1 to 30 carbon atoms, or -C(=O)-.
在本說明書的一實施形態中,L1為直接鍵結、碳個數為1至20的經取代或未經取代的伸烷基、或-C(=O)-。 In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, or -C(=O)-.
在本說明書的一實施形態中,L1為直接鍵結、碳個數為1至10的經取代或未經取代的伸烷基、或-C(=O)-。 In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted alkylene having 1 to 10 carbon atoms, or -C(=O)-.
在本說明書的一實施形態中,L1為直接鍵結。 In one embodiment of this specification, L1 is a direct bond.
在本說明書的一實施形態中,L1為經取代或未經取代的亞甲基、經取代或未經取代的伸乙基、或者經取代或未經取代的伸丙基。 In one embodiment of the present specification, L1 is a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylidene group, or a substituted or unsubstituted propylidene group.
在本說明書的一實施形態中,L1為亞甲基、伸乙基、或伸丙 基。 In one embodiment of this specification, L1 is methylene, ethylidene, or propyleneidene base.
在本說明書的一實施形態中,L1為-C(=O)-。 In one embodiment of this specification, L1 is -C(=O)-.
在本說明書的一實施形態中,L2為直接鍵結、-C(=O)-、或-L3-O(C=O)-。 In one embodiment of this specification, L2 is a direct bond, -C(=O)-, or -L3-O(C=O)-.
在本說明書的一實施形態中,L2為直接鍵結。 In one embodiment of this specification, L2 is a direct bond.
在本說明書的一實施形態中,L2為-C(=O)-。 In one embodiment of this specification, L2 is -C(=O)-.
在本說明書的一實施形態中,L2為-L3-O(C=O)-。 In one embodiment of this specification, L2 is -L3-O(C=O)-.
在本說明書的一實施形態中,L3為碳個數為1至30的經取代或未經取代的伸烷基。 In one embodiment of the present specification, L3 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.
在本說明書的一實施形態中,L3為碳個數為1至20的經取代或未經取代的伸烷基。 In one embodiment of the present specification, L3 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.
在本說明書的一實施形態中,L3為碳個數為1至10的經取代或未經取代的伸烷基。 In one embodiment of the present specification, L3 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.
在本說明書的一實施形態中,L3為經取代或未經取代的亞甲基。 In one embodiment of the present specification, L3 is a substituted or unsubstituted methylene group.
在本說明書的一實施形態中,L3為亞甲基。 In one embodiment of this specification, L3 is a methylene group.
在本說明書的一實施形態中,R1至R3彼此相同或不同,分別獨立地為氫、羥基、碳個數為1至30的經取代或未經取代的烷基。 In one embodiment of the present specification, R1 to R3 are the same or different from each other, and are independently hydrogen, hydroxyl, and substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms.
在本說明書的一實施形態中,R1至R3彼此相同或不同,分別獨立地為氫、羥基、碳個數為1至20的經取代或未經取代的烷基。 In one embodiment of the present specification, R1 to R3 are the same or different from each other, and are independently hydrogen, hydroxyl, and substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms.
在本說明書的一實施形態中,R1至R3彼此相同或不同,分別獨立地為氫、羥基、碳個數為1至10的經取代或未經取代的烷基。 In one embodiment of the present specification, R1 to R3 are the same or different from each other, and are independently hydrogen, hydroxyl, and substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms.
在本說明書的一實施形態中,R1至R3彼此相同或不同,分別獨立地為氫、羥基、經取代或未經取代的甲基。 In one embodiment of the present specification, R1 to R3 are the same or different from each other, and are each independently hydrogen, hydroxyl, substituted or unsubstituted methyl.
在本說明書的一實施形態中,R1為氫或甲基。 In one embodiment of the present specification, R1 is hydrogen or methyl.
在本說明書的一實施形態中,R2為氫。 In one embodiment of the present specification, R2 is hydrogen.
在本說明書的一實施形態中,R3為氫、羥基、或者由胺基取代的甲基。 In one embodiment of the present specification, R3 is hydrogen, a hydroxyl group, or a methyl group substituted with an amino group.
根據本說明書的一實施形態,所述化學式1可由下述化學式1-1表示。 According to an embodiment of the present specification, the chemical formula 1 can be represented by the following chemical formula 1-1.
在所述化學式1-1中,意指與其他單體或鍵結部連接的部分,X'、L1、L2、R1至R3、r2及r3與在所述化學式1中定義的內容相同。 In the chemical formula 1-1, Means a moiety linked to other monomers or linkages, X', L1, L2, R1 to R3, r2 and r3 are the same as those defined in the Chemical Formula 1.
在本說明書的一實施形態中,所述化學式1可由下述結構中的任一者表示,但並不限定於此。所述化學式1形成由下述結構中的任一者聚合的部分。 In one embodiment of the present specification, the chemical formula 1 can be represented by any one of the following structures, but is not limited to this. The Chemical Formula 1 forms a moiety polymerized from any one of the following structures.
本說明書的一實施形態提供一種所述三芳基甲烷染料單體為由下述化學式2表示的化合物。 One embodiment of the present specification provides that the triarylmethane dye monomer is a compound represented by the following chemical formula 2.
在所述化學式2中,R11至R14彼此相同或不同,分別獨立地為經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、或者經取代或未經取代的烷氧基,X1及X2彼此相同或不同,分別獨立地為氫、氘、鹵素基、羥基、-COOH、經取代或未經取代的烷氧基、經取代或未經取代
的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、或者經取代或未經取代的雜芳基,x1及x2為0至4的整數,在x1為2或大於2的情況下,X1彼此相同或不同,在x2為2或大於2的情況下,X2彼此相同或不同,A由下述化學式A-1至下述化學式A-3中的任一者表示,
[A-3]
在所述化學式A-1至下述化學式A-3中,意指與其他單體或鍵結部連接的部分,意指與所述化學式2的A連接的部分,Z為N或CR,所述R為氫、或者經取代或未經取代的烷基,R4至R6彼此相同或不同,分別獨立地為氫、氘、或者經取代或未經取代的烷基,R15及R16彼此相同或不同,分別獨立地為氫、氘、經取代或未經取代的烷基、或者經取代或未經取代的芳基,X為陰離子性基,X3至X6彼此相同或不同,分別獨立地為氫、氘、鹵素基、羥基、-COOH、經取代或未經取代的烷氧基、經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、或者經取代或未經取代的雜芳基,x3為0至3的整數,在x3為2或大於2的情況下,X3彼此 相同或不同,x4為0至10的整數,在x4為2或大於2的情況下,X4彼此相同或不同,x5為0至4的整數,在x5為2或大於2的情況下,X5彼此相同或不同,x6為0至4的整數,在x6為2或大於2的情況下,X6彼此相同或不同,B為經取代或未經取代的芳基,或者經取代或未經取代的烷基。 In the chemical formula A-1 to the following chemical formula A-3, means a moiety linked to other monomers or linkages, means a moiety connected to A of the Chemical Formula 2, Z is N or CR, the R is hydrogen, or a substituted or unsubstituted alkyl group, R4 to R6 are the same or different from each other, and are independently hydrogen, Deuterium, or substituted or unsubstituted alkyl, R15 and R16 being the same or different from each other, each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, X is an anionic group, X3 to X6 are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, hydroxyl, -COOH, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl , substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, x3 is an integer from 0 to 3, where x3 is 2 or more In the case where X3 is the same or different from each other, x4 is an integer from 0 to 10, in the case where x4 is 2 or more, X4 is the same or different from each other, x5 is an integer from 0 to 4, and x5 is 2 or more than 2 where X5 is the same or different from each other, x6 is an integer from 0 to 4, where x6 is 2 or more, X6 is the same or different from each other, B is substituted or unsubstituted aryl, or substituted or unsubstituted alkyl.
在本說明書的一實施形態中,R11至R14彼此相同或不同,分別獨立地為經取代或未經取代的烷基、或者經取代或未經取代的芳基。 In one embodiment of the present specification, R11 to R14 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
在本說明書的一實施形態中,R11至R14彼此相同或不同,分別獨立地為碳個數為1至30的經取代或未經取代的烷基、或者碳個數為6至30的經取代或未經取代的芳基。 In one embodiment of the present specification, R11 to R14 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbons, or a substituted alkyl group having 6 to 30 carbons. or unsubstituted aryl.
在本說明書的一實施形態中,R11至R14彼此相同或不同,分別獨立地為碳個數為1至20的經取代或未經取代的烷基、或者碳個數為6至20的經取代或未經取代的芳基。 In one embodiment of the present specification, R11 to R14 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbons, or a substituted alkyl group having 6 to 20 carbons. or unsubstituted aryl.
在本說明書的一實施形態中,R11至R14彼此相同或不同,分別獨立地為碳個數為1至10的經取代或未經取代的烷基、或者碳個數為6至12的經取代或未經取代的芳基。 In one embodiment of the present specification, R11 to R14 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbons, or a substituted alkyl group having 6 to 12 carbons. or unsubstituted aryl.
在本說明書的一實施形態中,R11至R14彼此相同或不同, 分別獨立地為經取代或未經取代的甲基、經取代或未經取代的乙基、經取代或未經取代的丙基、或者經取代或未經取代的苯基。 In one embodiment of the present specification, R11 to R14 are the same or different from each other, are each independently substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, or substituted or unsubstituted phenyl.
在本說明書的一實施形態中,R11至R14彼此相同或不同,分別獨立地為甲基、乙基、由烷氧基取代的乙基、異丙基、正丙基、苯基、或者由甲基取代的苯基。 In one embodiment of the present specification, R11 to R14 are the same or different from each other, and are each independently methyl, ethyl, ethyl substituted by alkoxy, isopropyl, n-propyl, phenyl, or methyl substituted phenyl.
在本說明書的一實施形態中,Z為N。 In one embodiment of this specification, Z is N.
在本說明書的一實施形態中,Z為CR。 In one embodiment of the present specification, Z is CR.
在本說明書的一實施形態中,R為氫、或者經取代或未經取代的烷基。 In one embodiment of the present specification, R is hydrogen, or a substituted or unsubstituted alkyl group.
在本說明書的一實施形態中,R為氫、或者碳個數為1至30的經取代或未經取代的烷基。 In one embodiment of the present specification, R is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
在本說明書的一實施形態中,R為氫、或者碳個數為1至20的經取代或未經取代的烷基。 In one embodiment of the present specification, R is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
在本說明書的一實施形態中,R為氫、或者碳個數為1至10的經取代或未經取代的烷基。 In one embodiment of the present specification, R is hydrogen, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
在本說明書的一實施形態中,R為氫。 In one embodiment of the present specification, R is hydrogen.
在本說明書的一實施形態中,R4至R6彼此相同或不同,分別獨立地為氫、氘、或者經取代或未經取代的烷基。 In one embodiment of the present specification, R4 to R6 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group.
在本說明書的一實施形態中,R4至R6彼此相同或不同,分別獨立地為氫、氘、或者碳個數為1至30的經取代或未經取代的烷基。 In one embodiment of the present specification, R4 to R6 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
在本說明書的一實施形態中,R4至R6彼此相同或不同,分 別獨立地為氫、氘、或者碳個數為1至20的經取代或未經取代的烷基。 In an embodiment of the present specification, R4 to R6 are the same or different from each other, respectively Each is independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 20 carbons.
在本說明書的一實施形態中,R4至R6彼此相同或不同,分別獨立地為氫、氘、或者碳個數為1至10的經取代或未經取代的烷基。 In one embodiment of the present specification, R4 to R6 are the same or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 10 carbons.
在本說明書的一實施形態中,R4至R6為經取代或未經取代的甲基。 In one embodiment of the present specification, R4 to R6 are substituted or unsubstituted methyl groups.
在本說明書的一實施形態中,R4至R6為甲基。 In one embodiment of the present specification, R4 to R6 are methyl groups.
在本說明書的一實施形態中,R15及R16彼此相同或不同,分別獨立地為氫、氘、經取代或未經取代的烷基、或者經取代或未經取代的芳基。 In one embodiment of the present specification, R15 and R16 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.
在本說明書的一實施形態中,R15及R16彼此相同或不同,分別獨立地為氫、氘、碳個數為1至30的經取代或未經取代的烷基、或者碳個數為6至30的經取代或未經取代的芳基。 In one embodiment of the present specification, R15 and R16 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbons, or 6 to 6 carbons. 30 of substituted or unsubstituted aryl.
在本說明書的一實施形態中,R15及R16彼此相同或不同,分別獨立地為氫、氘、碳個數為1至20的經取代或未經取代的烷基、或者碳個數為6至20的經取代或未經取代的芳基。 In one embodiment of the present specification, R15 and R16 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbons, or 6 to 6 carbons. 20 substituted or unsubstituted aryl.
在本說明書的一實施形態中,R15及R16彼此相同或不同,分別獨立地為氫、氘、碳個數為1至10的經取代或未經取代的烷基、或者碳個數為6至12的經取代或未經取代的芳基。 In one embodiment of the present specification, R15 and R16 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 10 carbons, or 6 to 6 carbons. The substituted or unsubstituted aryl of 12.
在本說明書的一實施形態中,R15為經取代或未經取代的乙基。 In one embodiment of the present specification, R15 is a substituted or unsubstituted ethyl group.
在本說明書的一實施形態中,R15為乙基。 In one embodiment of the present specification, R15 is an ethyl group.
在本說明書的一實施形態中,R16為經取代或未經取代的苯基。 In one embodiment of the present specification, R16 is a substituted or unsubstituted phenyl group.
在本說明書的一實施形態中,R16為由鹵素基取代或未經取代的苯基。 In one embodiment of the present specification, R16 is a phenyl group substituted or unsubstituted with a halogen group.
在本說明書的一實施形態中,R16為由氟取代或未經取代的苯基。 In one embodiment of the present specification, R16 is a fluorine-substituted or unsubstituted phenyl group.
在本說明書的一實施形態中,X可為雙三氟甲烷磺醯亞胺陰離子。 In one embodiment of the present specification, X may be a bistrifluoromethanesulfonimide anion.
在本說明書的一實施形態中,X1及X2彼此相同或不同,分別獨立地為氫、氘、鹵素基、羥基、-COOH、經取代或未經取代的烷氧基、經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、或者經取代或未經取代的雜芳基。 In one embodiment of this specification, X1 and X2 are the same or different from each other, and are independently hydrogen, deuterium, halogen, hydroxyl, -COOH, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
在本說明書的一實施形態中,X1及X2彼此相同或不同,分別獨立地為氫、鹵素基、或者經取代或未經取代的烷基。 In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently hydrogen, a halogen group, or a substituted or unsubstituted alkyl group.
在本說明書的一實施形態中,X1及X2彼此相同或不同,分別獨立地為氫、鹵素基、或者碳個數為1至30的經取代或未經取代的烷基。 In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently hydrogen, a halogen group, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
在本說明書的一實施形態中,X1及X2彼此相同或不同,分別獨立地為氫、鹵素基、或者碳個數為1至20的經取代或未經取代的烷基。 In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently hydrogen, a halogen group, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
在本說明書的一實施形態中,X1及X2彼此相同或不同,分別獨立地為氫、鹵素基、或者碳個數為1至10的經取代或未經取代的烷基。 In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently hydrogen, a halogen group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
在本說明書的一實施形態中,X1及X2彼此相同或不同,分別獨立地為氫、鹵素基、或者經取代或未經取代的甲基。 In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently hydrogen, a halogen group, or a substituted or unsubstituted methyl group.
在本說明書的一實施形態中,X1及X2彼此相同或不同,分別獨立地為氫、氟、氯、或甲基。 In one embodiment of the present specification, X1 and X2 are the same or different from each other, and are each independently hydrogen, fluorine, chlorine, or methyl.
在本說明書的一實施形態中,X3至X6彼此相同或不同,分別獨立地為氫、氘、鹵素基、羥基、-COOH、經取代或未經取代的烷氧基、經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、或者經取代或未經取代的雜芳基。 In one embodiment of this specification, X3 to X6 are the same or different from each other, and are independently hydrogen, deuterium, halogen, hydroxyl, -COOH, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
在本說明書的一實施形態中,X3至X6彼此相同或不同,分別獨立地為氫、-COOH、或者經取代或未經取代的烷基。 In one embodiment of the present specification, X3 to X6 are the same or different from each other, and are each independently hydrogen, -COOH, or a substituted or unsubstituted alkyl group.
在本說明書的一實施形態中,X3至X6彼此相同或不同,分別獨立地為氫、-COOH、或者碳個數為1至30的經取代或未經取代的烷基。 In one embodiment of the present specification, X3 to X6 are the same or different from each other, and are each independently hydrogen, -COOH, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
在本說明書的一實施形態中,X3至X6彼此相同或不同,分別獨立地為氫、-COOH、或者碳個數為1至20的經取代或未經取代的烷基。 In one embodiment of the present specification, X3 to X6 are the same or different from each other, and are each independently hydrogen, -COOH, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
在本說明書的一實施形態中,X3至X6彼此相同或不同,分別獨立地為氫、-COOH、或者碳個數為1至10的經取代或未經取 代的烷基。 In one embodiment of the present specification, X3 to X6 are the same or different from each other, and are independently hydrogen, -COOH, or substituted or unsubstituted carbons having 1 to 10 carbons. substituted alkyl.
在本說明書的一實施形態中,X3至X6彼此相同或不同,分別獨立地為氫、-COOH、或者經取代或未經取代的甲基。 In one embodiment of the present specification, X3 to X6 are the same or different from each other, and are each independently hydrogen, -COOH, or a substituted or unsubstituted methyl group.
在本說明書的一實施形態中,X3至X6彼此相同或不同,分別獨立地為氫、-COOH、或甲基。 In one embodiment of the present specification, X3 to X6 are the same as or different from each other, and are each independently hydrogen, -COOH, or methyl.
在本說明書的一實施形態中,B為碳個數為6至30的經取代或未經取代的芳基、或者碳個數為1至30的經取代或未經取代的烷基。 In one embodiment of the present specification, B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
在本說明書的一實施形態中,B為碳個數為6至20的經取代或未經取代的芳基、或者碳個數為1至20的經取代或未經取代的烷基。 In one embodiment of the present specification, B is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
在本說明書的一實施形態中,B為碳個數為6至12的經取代或未經取代的芳基、或者碳個數為1至10的烷基。 In one embodiment of the present specification, B is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or an alkyl group having 1 to 10 carbon atoms.
在本說明書的一實施形態中,B為經取代或未經取代的苯基。 In one embodiment of the present specification, B is a substituted or unsubstituted phenyl group.
在本說明書的一實施形態中,B為苯基。 In one embodiment of the present specification, B is a phenyl group.
在本說明書的一實施形態中,所述化學式2可由下述化學式2-1至下述化學式2-3中的任一者表示。 In one embodiment of the present specification, the chemical formula 2 can be represented by any one of the following chemical formula 2-1 to the following chemical formula 2-3.
[化學式2-1]
[化學式2-3]
在所述化學式2-1至化學式2-3中,R11至R16、R4至R6、X1至X6、x1至x6、Z、X及B與在所述化學式2中定義的內容相同。 In the Chemical Formulas 2-1 to 2-3, R11 to R16, R4 to R6, X1 to X6, x1 to x6, Z, X, and B are the same as those defined in the Chemical Formula 2.
在本說明書的一實施形態中,所述化學式2-1可由下述化學式2-1-1表示。 In one embodiment of the present specification, the chemical formula 2-1 can be represented by the following chemical formula 2-1-1.
[化學式2-1-1]
在所述化學式2-1-1中,R11至R14、R4、X1至X4、x1至x4、Z及X與在所述化學式2中定義的內容相同。 In the Chemical Formula 2-1-1, R11 to R14, R4, X1 to X4, x1 to x4, Z and X are the same as those defined in the Chemical Formula 2.
在本說明書的一實施形態中,所述化學式2-2可由下述化學式2-2-1表示。 In one embodiment of the present specification, the chemical formula 2-2 can be represented by the following chemical formula 2-2-1.
[化學式2-2-1]
在所述化學式2-2-1中,R11至R14、R5、X1、X2、X5、x1、x2、x5、X及B與在所述化學式2中定義的內容相同。 In the Chemical Formula 2-2-1, R11 to R14, R5, X1, X2, X5, x1, x2, x5, X and B are the same as those defined in the Chemical Formula 2.
在本說明書的一實施形態中,所述化學式2-3可由下述化學式2-3-1表示。 In one embodiment of the present specification, the chemical formula 2-3 can be represented by the following chemical formula 2-3-1.
在所述化學式2-3-1中,R11至R16、R6、X1、X2、X6、x1、x2、x6及X與在所述化學式2中定義的內容相同。 In the Chemical Formula 2-3-1, R11 to R16, R6, X1, X2, X6, x1, x2, x6 and X are the same as those defined in the Chemical Formula 2.
在本說明書的一實施形態中,所述化學式2可由下述結構中的任一者表示,但並不限定於此。 In one embodiment of the present specification, the chemical formula 2 can be represented by any one of the following structures, but is not limited to this.
在所述結構中,X與在所述化學式2中定義的內容相同。具體而言,X與在所述化學式A-1至化學式A-3中定義的內容相同。 In the structure, X is the same as that defined in the Chemical Formula 2. Specifically, X is the same as that defined in the Chemical Formulas A-1 to A-3.
在本說明書中,(甲基)丙烯酸單體可由下述化學式B表示。 In the present specification, the (meth)acrylic monomer may be represented by the following Chemical Formula B.
[化學式B]
在所述化學式B中,T1為氫、-COOH、經取代或未經取代的烷基、或者經取代或未經取代的烷氧基,T2為氫、或者經取代或未經取代的烷基,M為直接鍵結、或者經取代或未經取代的伸烷基。 In the chemical formula B, T1 is hydrogen, -COOH, substituted or unsubstituted alkyl, or substituted or unsubstituted alkoxy, T2 is hydrogen, or substituted or unsubstituted alkyl , M is a direct bond, or a substituted or unsubstituted alkylene.
在本說明書的一實施形態中,T1為氫、-COOH、碳個數為1至30的經取代或未經取代的烷基、或者碳個數為1至30的經取代或未經取代的烷氧基。 In one embodiment of this specification, T1 is hydrogen, -COOH, substituted or unsubstituted alkyl with 1 to 30 carbons, or substituted or unsubstituted with 1 to 30 carbons alkoxy.
在本說明書的一實施形態中,T1為氫、-COOH、碳個數為1至20的經取代或未經取代的烷基、或者碳個數為1至20的經取代或未經取代的烷氧基。 In one embodiment of this specification, T1 is hydrogen, -COOH, substituted or unsubstituted alkyl with 1 to 20 carbons, or substituted or unsubstituted with 1 to 20 carbons alkoxy.
在本說明書的一實施形態中,T1為氫、-COOH、碳個數為1至10的經取代或未經取代的烷基、或者碳個數為1至10的經取代或未經取代的烷氧基。 In one embodiment of this specification, T1 is hydrogen, -COOH, substituted or unsubstituted alkyl with 1 to 10 carbons, or substituted or unsubstituted with 1 to 10 carbons alkoxy.
在本說明書的一實施形態中,T1可為氫、-COOH、或者下述結構中的任一者。 In one embodiment of the present specification, T1 may be hydrogen, -COOH, or any one of the following structures.
在本說明書的一實施形態中,由所述化學式B表示的結 構可由下述結構中的任一者表示,但並不限定於此。 In one embodiment of the present specification, the structure represented by the chemical formula B The structure can be represented by any of the following structures, but is not limited to this.
本說明書的一實施形態提供一種化合物,以所述化合物的總重量為基準,包含55重量%至98重量%的所述三芳基甲烷染料單體、1重量%至30重量%的所述(甲基)丙烯酸單體、以及1重量%至20重量%的由所述化學式1表示的結構。 An embodiment of the present specification provides a compound, based on the total weight of the compound, comprising 55% to 98% by weight of the triarylmethane dye monomer, 1% to 30% by weight of the (methyl methane) base) an acrylic monomer, and 1 wt % to 20 wt % of the structure represented by the Chemical Formula 1.
較佳為,以所述化合物的總重量為基準,包含70重量%的所述三芳基甲烷染料單體、20重量%的所述(甲基)丙烯酸單體、以及5重量%的由所述化學式1表示的結構。 Preferably, based on the total weight of the compound, it comprises 70% by weight of the triarylmethane dye monomer, 20% by weight of the (meth)acrylic monomer, and 5% by weight of the The structure represented by Chemical Formula 1.
所述三芳基甲烷系高分子染料可由三芳基甲烷系染料與另一單體的鍵結來形成。三芳基甲烷系染料的含量應大於50重量%以上才會表現出足夠的顏色,較佳為在70重量%以上時可藉由少的含量表現出適當的顏色(color)。 The triarylmethane-based polymer dye can be formed by bonding the triarylmethane-based dye with another monomer. The content of the triarylmethane-based dye should be more than 50% by weight to express sufficient color, and preferably, when the content is more than 70% by weight, a suitable color can be expressed with a small content.
在本說明書的一實施形態中,所述化合物的重量平均分子量為5,000g/mol至35,000g/mol。較佳可為15,000g/mol至30,000g/mol。 In one embodiment of the present specification, the weight average molecular weight of the compound is 5,000 g/mol to 35,000 g/mol. It is preferably 15,000 g/mol to 30,000 g/mol.
藉由使所述化合物滿足所述重量平均分子量的範圍,從而可具有適當的顯影時間與耐熱性。 Appropriate development time and heat resistance can be obtained by making the compound satisfy the range of the weight average molecular weight.
在所述化合物的重量平均分子量小於5,000g/mol的情況,會使藉由顯影液去除顏色材料的量變多,因熱引起的顏色變化變大。在所述化合物的重量平均分子量大於35,000g/mol的情況,會使顯影時間增加。 When the weight-average molecular weight of the compound is less than 5,000 g/mol, the amount of the color material removed by the developer increases, and the color change due to heat increases. In the case where the weight average molecular weight of the compound is greater than 35,000 g/mol, the development time may be increased.
所述重量平均分子量是分子量不均勻且以某種高分子物質的分子量為基準使用的平均分子量中的一種,且是藉由利用重量百分比對存在分子量分佈的高分子化合物的成分分子物種的分子量進行平均而得到的值。 The weight average molecular weight is one of the average molecular weights that are not uniform in molecular weight and used on the basis of the molecular weight of a certain macromolecular substance, and is calculated by using the weight percentage to determine the molecular weight of the component molecular species of the macromolecular compound having a molecular weight distribution. averaged value.
所述重量平均分子量可藉由高效液相層析(High Performance Liquid Chromatography,HPLC)分析來測定。 The weight average molecular weight can be determined by High Performance Liquid Chromatography (HPLC) analysis.
在本說明書的一實施形態中,所述化合物的數平均分子量可為20至32。藉由使所述化合物滿足所述數平均分子量的範圍,從而可具有適當的顯影時間與耐熱性。 In one embodiment of the present specification, the number average molecular weight of the compound may be 20 to 32. Appropriate development time and heat resistance can be obtained by making the compound satisfy the range of the number average molecular weight.
所述數平均分子量意指藉由利用數百分比或莫耳百分比對具有分子量分佈的高分子化合物的成分分子物種的分子量進行平均而獲得的平均分子量。 The number average molecular weight means an average molecular weight obtained by averaging molecular weights of constituent molecular species of a high molecular compound having a molecular weight distribution by number percentage or molar percentage.
所述數平均分子量可藉由高效液相層析(High Performance Liquid Chromatography,HPLC)分析來測定。 The number average molecular weight can be determined by High Performance Liquid Chromatography (HPLC) analysis.
在本說明書的一實施形態中,所述化合物的分散度可為2至3。具體而言,所述分散度可為2.28至2.97。 In one embodiment of the present specification, the dispersity of the compound may be 2 to 3. Specifically, the degree of dispersion may be 2.28 to 2.97.
所述分散度為多分散指數(Poly Dispersity Index,PDI),表示為重量平均分子量值除以數平均分子量的值。 The degree of dispersity is the polydispersity index (Poly Dispersity Index, PDI), expressed as the value of the weight average molecular weight divided by the number average molecular weight.
在本說明書的一實施形態中,所述化合物可包含一種以上的三芳基甲烷染料單體。 In one embodiment of the present specification, the compound may contain one or more triarylmethane dye monomers.
在本說明書的一實施形態中,所述(甲基)丙烯酸單體可包含一種以上的(甲基)丙烯酸單體。 In one embodiment of the present specification, the (meth)acrylic monomer may contain one or more (meth)acrylic monomers.
在本說明書的一實施形態中,所述化合物可更包含熱硬化性單體。 In one embodiment of the present specification, the compound may further contain a thermosetting monomer.
所述熱硬化性單體可為甲基丙烯酸縮水甘油酯、氧環丁烷或M-100,但並不限定於此。 The thermosetting monomer may be, but not limited to, glycidyl methacrylate, oxetane or M-100.
所述甲基丙烯酸縮水甘油酯可由下述結構表示。 The glycidyl methacrylate can be represented by the following structure.
所述氧環丁烷可由下述結構表示。 The oxetane can be represented by the following structure.
所述M-100可由下述結構表示。 The M-100 can be represented by the following structure.
在本說明書的一實施形態中,所述化合物視需要可更包含苯乙烯單體。 In one embodiment of the present specification, the compound may further contain a styrene monomer if necessary.
本說明書的一實施形態提供一種著色劑組成物,包含所述化合物、黏合劑樹脂、多官能性單體、光起始劑、以及溶劑。 One embodiment of the present specification provides a colorant composition including the compound, a binder resin, a multifunctional monomer, a photoinitiator, and a solvent.
在本說明書的一實施形態中,所述著色劑組成物可更包含顏料及染料中的一種以上。 In one embodiment of the present specification, the colorant composition may further include at least one of a pigment and a dye.
例如,所述著色劑組成物亦可包含僅所述化學式1的化合物,但亦可包含所述化學式1的化合物與一種以上的染料、或者包含所述化學式1的化合物與一種以上的顏料、或者包含所述化學式1的化合物、一種以上的染料及一種以上的顏料。 For example, the colorant composition may include only the compound of the chemical formula 1, but may also include the compound of the chemical formula 1 and one or more dyes, or the compound of the chemical formula 1 and more than one pigment, or The compound of Chemical Formula 1, one or more dyes, and one or more pigments are included.
所述染料及顏料可選自由以下所組成的群組中的一種以上:金屬錯合物(metal-complex)系列化合物;偶氮(azo)系列化合物;金屬偶氮(metal azo)系列化合物;喹酞酮(quinophthalone)系列化合物;異吲哚啉(isoindoline)系列化合物;次甲基(Methine)系列化合物;酞青(phthalocyanine)系列化合物;金屬酞青(metal phthalocyanine)系列化合物;卟啉(porphyrin)系列化合物;金屬卟啉(metal porphyrin)系列化合物;四氮雜卟啉(tetra aza porphyrin)系列化合物;金屬四氮雜卟啉(metal tetra aza porphyrin)系列化合物;花青(Cyanine)系列化合物;二苯並哌喃(Xanthene)系列化合物;金屬二吡咯亞甲基(metal dipyrromethene)系列化合物;硼二吡咯亞甲基(boron dipyrromethene)系列化合物;金屬二吡咯亞甲基(metal dipyrromethene)系列化合物;蒽醌(anthraquinone)系列化合物;二酮基吡咯並吡咯(diketopyrrolopyrrole)系列化合物;三芳基甲烷(triarylmethane)系列化合物;以及苝(perylene)系列化合物。 The dyes and pigments can be selected from one or more of the following groups: metal-complex series compounds; azo (azo) series compounds; metal azo (metal azo) series compounds; quinophthalone series compounds; isoindoline series compounds; methine series compounds; phthalocyanine series compounds; metal phthalocyanine series compounds; porphyrins series compounds; metal porphyrin series compounds; tetra aza porphyrin (tetra aza) porphyrin) series compounds; metal tetra aza porphyrin series compounds; cyanine (Cyanine) series compounds; dibenzopyran (Xanthene) series compounds; metal dipyrromethene series Compounds; Boron dipyrromethene series compounds; Metal dipyrromethene series compounds; Anthraquinone series compounds; Diketopyrrolopyrrole series compounds; Triaryl groups Methane (triarylmethane) series compounds; and perylene (perylene) series compounds.
具體而言,所述顏料可為酞青(phthalocyanine)系列化合物,可為B15:6、G7、G58、G59或G36。 Specifically, the pigment can be a phthalocyanine series compound, which can be B15:6, G7, G58, G59 or G36.
具體而言,所述染料可為二苯並哌喃(Xanthene)系列化合物、金屬錯合物(metal-complex)系列化合物或喹酞酮(quinophthalone)系列化合物。 Specifically, the dyes may be Xanthene series compounds, metal-complex series compounds or quinophthalone series compounds.
所述黏合劑樹脂若為可顯示出由著色劑組成物所製造的膜的強度、顯影性等物性者,則並無特別限定。 The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of the film produced from the colorant composition.
所述黏合劑樹脂可使用賦予機械強度的多官能性單體與賦予鹼溶解性的單體的共聚樹脂,亦可更包含本技術領域中通常所使用的黏合劑。 The binder resin may use a copolymer resin of a multifunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility, or may further include a binder commonly used in this technical field.
賦予所述膜的機械強度的多官能性單體可為不飽和羧酸酯類、芳香族乙烯基類、不飽和醚類、不飽和醯亞胺類及酸酐中的任一者以上。 The polyfunctional monomer that imparts mechanical strength to the film may be any or more of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated imides, and acid anhydrides.
作為所述不飽和羧酸酯類的具體例,可選自由(甲基)丙烯酸 苄酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸2-苯氧基乙酯、(甲基)丙烯酸四氫糠酯、(甲基)丙烯酸羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基-3-氯丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸醯基辛基氧基-2-羥基丙酯、丙三醇(甲基)丙烯酸酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸3-甲氧基丁酯、乙氧基二乙二醇(甲基)丙烯酸酯、甲氧基三乙二醇(甲基)丙烯酸酯、甲氧基三丙二醇(甲基)丙烯酸酯、聚(乙二醇)甲醚(甲基)丙烯酸酯、苯氧基二乙二醇(甲基)丙烯酸酯、對壬基苯氧基聚乙二醇(甲基)丙烯酸酯、對壬基苯氧基聚丙二醇(甲基)丙烯酸酯、(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸四氟丙酯、(甲基)丙烯酸1,1,1,3,3,3-六氟異丙酯、(甲基)丙烯酸八氟戊酯、(甲基)丙烯酸十七氟癸酯、(甲基)丙烯酸三溴苯酯、α-羥基甲基丙烯酸甲酯、α-羥基甲基丙烯酸乙酯、α-羥基甲基丙烯酸丙酯及α-羥基甲基丙烯酸丁酯所組成的群組中,但並不僅限定於該些。 As a specific example of the unsaturated carboxylic acid esters, (meth)acrylic acid can be selected Benzyl ester, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, isobutyl (meth)acrylate, ( 3-butyl meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, Tetrahydrofurfuryl (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, (meth)acrylic acid 4-Hydroxybutyl, (meth)acryloyl octyloxy-2-hydroxypropyl, glycerol (meth)acrylate, (meth)acrylate 2-methoxyethyl, (meth)acrylate ) 3-methoxybutyl acrylate, ethoxydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, Poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, p-nonylphenoxy polyethylene glycol (meth)acrylate, p-nonylbenzene Oxypolypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroiso (meth)acrylate Propyl, Octafluoropentyl (Meth)acrylate, Heptafluorodecyl (Meth)acrylate, Tribromophenyl (Meth)acrylate, α-Hydroxymethyl Methacrylate, Ethyl α-Hydroxymethacrylate ester, α-hydroxypropyl methacrylate and α-hydroxy butyl methacrylate, but not limited to these.
作為所述芳香族乙烯基單量體類的具體例,可選自由苯乙烯、α-甲基苯乙烯、(鄰、間、對)-乙烯基甲苯、(鄰、間、對)-甲氧基苯乙烯及(鄰、間、對)-氯苯乙烯所組成的群組中,但並不僅限定於該些。 Specific examples of the aromatic vinyl monomers can be selected from styrene, α-methylstyrene, (o, m, p)-vinyltoluene, (o, m, p)-methoxy In the group consisting of styrene and (o-, m-, p-)-chlorostyrene, but not limited to these.
作為所述不飽和醚類的具體例,可選自由乙烯基甲醚、乙烯 基乙醚及烯丙基縮水甘油醚所組成的群組中,但並不僅限定於該些。 Specific examples of the unsaturated ethers can be selected from vinyl methyl ether, ethylene In the group consisting of ethyl ether and allyl glycidyl ether, it is not limited to these.
作為所述不飽和醯亞胺類的具體例,可選自由N-苯基馬來醯亞胺、N-(4-氯苯基)馬來醯亞胺、N-(4-羥基苯基)馬來醯亞胺及N-環己基馬來醯亞胺所組成的群組中,但並不僅限定於該些。 Specific examples of the unsaturated imides include N-phenylmaleimide, N-(4-chlorophenyl)maleimide, and N-(4-hydroxyphenyl) In the group consisting of maleimide and N-cyclohexylmaleimide, it is not limited to these.
作為所述酸酐,有馬來酸酐、甲基馬來酸酐、四氫鄰苯二甲酸酐等,但並不僅限定於該些。 The acid anhydride includes maleic anhydride, methylmaleic anhydride, tetrahydrophthalic anhydride, and the like, but is not limited to these.
賦予鹼溶解性的所述單體若為包含酸基者,則並無特別限定,例如較佳為使用選自由(甲基)丙烯酸、巴豆酸、衣康酸、馬來酸、富馬酸、單甲基馬來酸、5-降冰片烯-2-羧酸、鄰苯二甲酸單-2-((甲基)丙烯醯氧基)乙酯、琥珀酸單-2-((甲基)丙烯醯氧基)乙酯、ω-羧基聚己內酯單(甲基)丙烯酸酯所組成的群組中的一種以上,但並不僅限定於該些。 The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group. Monomethylmaleic acid, 5-norbornene-2-carboxylic acid, mono-2-((meth)acryloyloxy)ethyl phthalate, mono-2-((methyl) succinate One or more of the group consisting of acryloxy) ethyl ester and ω-carboxy polycaprolactone mono(meth)acrylate, but not limited to these.
在本說明書的一實施形態中,所述多官能性單體具體而言可為二季戊四醇六丙烯酸酯。 In one embodiment of the present specification, the polyfunctional monomer may specifically be dipentaerythritol hexaacrylate.
根據本說明書的一實施形態,所述黏合劑樹脂的酸價為50KOH mg/g至130KOH mg/g,重量平均分子量為1,000g/mol至50,000g/mol。 According to an embodiment of the present specification, the acid value of the binder resin is 50KOH mg/g to 130KOH mg/g, and the weight average molecular weight is 1,000g/mol to 50,000g/mol.
所述黏合劑樹脂的酸價可利用0.1N濃度的氫氧化鉀(KOH)甲醇溶液滴定來測定。 The acid value of the binder resin can be determined by titration with 0.1N concentration of potassium hydroxide (KOH) methanol solution.
在本說明書的一實施形態中,黏合劑樹脂可為選自由甲基丙烯酸、縮水甘油基甲基丙烯酸、苯乙烯、甲基丙烯酸環己酯 及甲基丙烯酸酯所組成的群組中的一種以上的單體的共聚樹脂(共聚物)。 In one embodiment of this specification, the binder resin may be selected from methacrylic acid, glycidyl methacrylic acid, styrene, and cyclohexyl methacrylate A copolymer resin (copolymer) of one or more monomers in the group consisting of methacrylate.
具體而言,所述黏合劑樹脂可為如下共聚物:以共聚物總重量為基準,甲基丙烯酸、縮水甘油基甲基丙烯酸及苯乙烯可分別為13重量%、52重量%、35重量%。 Specifically, the binder resin can be the following copolymer: based on the total weight of the copolymer, methacrylic acid, glycidyl methacrylic acid and styrene can be 13% by weight, 52% by weight, and 35% by weight, respectively .
另外,所述黏合劑樹脂中,以共聚物總重量為基準,甲基丙烯酸環己酯、甲基丙烯酸酯及甲基丙烯酸可分別為45重量%、30重量%、25重量%。 In addition, in the binder resin, based on the total weight of the copolymer, cyclohexyl methacrylate, methacrylate and methacrylic acid may be respectively 45% by weight, 30% by weight, and 25% by weight.
所述光起始劑若為藉由光而產生自由基來引發交聯的起始劑,則並不特別限定,例如可為選自由苯乙酮系化合物、聯咪唑系化合物、三嗪系化合物及肟系化合物所組成的群組中的一種以上。 The photoinitiator is not particularly limited as long as it is an initiator that generates free radicals by light to initiate crosslinking, and for example, it can be selected from acetophenone-based compounds, biimidazole-based compounds, and triazine-based compounds. and one or more of the group consisting of oxime-based compounds.
所述苯乙酮系化合物有2-羥基-2-甲基-1-苯基丙烷-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、4-(2-羥基乙氧基)-苯基-(2-羥基-2-丙基)酮、1-羥基環己基苯基酮、安息香甲醚、安息香乙醚、安息香異丁醚、安息香丁醚、2,2-二甲氧基-2-苯基苯乙酮、2-甲基-(4-甲硫基)苯基-2-嗎啉基-1-丙烷-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-丁烷-1-酮、2-4-溴-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-丁烷-1-酮或2-甲基-1-[4-(甲硫基)苯基]-2-嗎啉基丙烷-1-酮等,並不限定於此。 The acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1 - ketone, 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Butyl benzoin, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-Benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-4-bromo-benzyl-2-dimethylamino-1 -(4-Morpholinylphenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, etc., and It is not limited to this.
作為所述聯咪唑系化合物,有2,2-雙(2-氯苯基)-4,4',5,5'-四苯基聯咪唑、2,2'-雙(鄰氯苯基)-4,4',5,5'-四(3,4,5-三甲氧基苯 基)-1,2'-聯咪唑、2,2'-雙(2,3-二氯苯基)-4,4',5,5'-四苯基聯咪唑、2,2'-雙(鄰氯苯基)-4,4,5,5'-四苯基-1,2'-聯咪唑等,並不限定於此。 As the biimidazole-based compound, there are 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl) -4,4',5,5'-Tetrakis(3,4,5-trimethoxybenzene base)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole etc. are not limited to this.
所述三嗪系化合物有3-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}丙酸、3-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}丙酸1,1,1,3,3,3-六氟異丙酯、2-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}乙酸乙酯、2-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}乙酸2-環氧基乙酯、2-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}乙酸環己酯、2-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}乙酸苄酯、3-{氯-4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}丙酸、3-{4-[2,4-雙(三氯甲基)-均三嗪-6-基]苯硫基}丙醯胺、2,4-雙(三氯甲基)-6-對甲氧基苯乙烯基-均三嗪、2,4-雙(三氯甲基)-6-(1-對二甲基胺基苯基)-1,3-丁二烯基-均三嗪、2-三氯甲基-4-胺基-6-對甲氧基苯乙烯基-均三嗪等,並不限定於此。 The triazine compounds include 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4- 1,1,1,3,3,3-hexafluoroisopropyl bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propanoate, 2-{4-[2,4- ethyl bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl] Phenylthio}acetic acid 2-epoxyethyl ester, 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetic acid cyclohexyl ester, 2- Benzyl {4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl) )-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionamide , 2,4-bis(trichloromethyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylamino) Phenyl)-1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, etc., are not limited thereto.
所述肟系化合物有1,2-辛二酮-1-(4-苯硫基)苯基-2-(鄰苯甲醯基肟)(汽巴-嘉基(Ciba-Geigy)公司,CGI-124)、乙酮-1-(9-乙基)-6-(2-甲基苯甲醯基-3-基)-1-(O-乙醯基肟)(CGI-242)、N-1919(艾迪科(Adeka)公司)等,並不限定於此。 The oxime series compounds include 1,2-octanedione-1-(4-phenylthio) phenyl-2-(o-benzyl oxime) (Ciba-Geigy), CGI -124), Ethanone-1-(9-ethyl)-6-(2-methylbenzyl-3-yl)-1-(O-acetyloxime) (CGI-242), N -1919 (Adeka), etc., but not limited to this.
在本說明書的一實施形態中,所述光起始劑具體而言可為SPI-03,但並不限定於此。 In one embodiment of the present specification, the photoinitiator may specifically be SPI-03, but it is not limited thereto.
所述溶劑可為選自由丙酮、甲基乙基酮、甲基異丁基酮、甲基溶纖劑、乙基溶纖劑、四氫呋喃、1,4-二噁烷、乙二醇二甲醚、乙二醇二乙醚、丙二醇二甲醚、丙二醇二乙醚、二乙二醇二甲醚、 二乙二醇二乙醚、二乙二醇甲基乙基醚、氯仿、二氯甲烷、1,2-二氯乙烷、1,1,1-三氯乙烷、1,1,2-三氯乙烷、1,1,2-三氯乙烯、己烷、庚烷、辛烷、環己烷、苯、甲苯、二甲苯、甲醇、乙醇、異丙醇、丙醇、丁醇、第三丁醇、2-乙氧基丙醇、2-甲氧基丙醇、3-甲氧基丁醇、環己酮、環戊酮、丙二醇甲醚乙酸酯、丙二醇乙醚乙酸酯、3-甲氧基丁基乙酸酯、3-乙氧基丙酸乙酯、乙基溶纖劑乙酸酯、甲基溶纖劑乙酸酯、乙酸丁酯、丙二醇單甲醚及二丙二醇單甲醚所組成的群組中的一種以上,但並不僅限定於此。 The solvent may be selected from acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether , ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, Diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, dichloromethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane Ethyl chloride, 1,1,2-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, third Butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3- Methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether One or more of the group consisting of ethers, but not limited to this.
具體而言,所述溶劑可為丙二醇單甲醚乙酸酯或二丙酮醇。 Specifically, the solvent may be propylene glycol monomethyl ether acetate or diacetone alcohol.
本說明書的一實施形態提供一種著色劑組成物,其中以所述著色劑組成物的總重量為基準,所述化合物的含量為1重量%至50重量%,所述黏合劑樹脂的含量為5重量%至40重量%,所述多官能性單體的含量為5重量%至40重量%,所述光起始劑的含量為1重量%至10重量%以及所述溶劑的含量為30重量%至80重量%。 An embodiment of the present specification provides a colorant composition, wherein based on the total weight of the colorant composition, the content of the compound is 1% by weight to 50% by weight, and the content of the binder resin is 5% by weight. % to 40% by weight, the content of the multifunctional monomer is 5% to 40% by weight, the content of the photoinitiator is 1% to 10% by weight, and the content of the solvent is 30% by weight % to 80% by weight.
本說明書的一實施形態提供一種著色劑組成物,其中以所述著色劑組成物中固體成分的總重量為基準,所述化合物的含量為1重量%至50重量%,所述黏合劑樹脂的含量為5重量%至40重量%,所述多官能性單體的含量為5重量%至40重量%,所述光起始劑的含量為1重量%至10重量%。 An embodiment of the present specification provides a colorant composition, wherein based on the total weight of solids in the colorant composition, the content of the compound is 1% by weight to 50% by weight, and the content of the binder resin is 1 to 50% by weight. The content is 5% to 40% by weight, the content of the multifunctional monomer is 5% to 40% by weight, and the content of the photoinitiator is 1% to 10% by weight.
在所述著色劑組成物所包含的各構成要素滿足所述範圍的情況,著色劑組成物內的化合物、黏合劑樹脂及多官能性單 體可藉由自由基聚合而彼此鍵結,從而可形成結實的膜。 When each component contained in the colorant composition satisfies the above-mentioned range, the compound, the binder resin, and the polyfunctional monomer in the colorant composition The bodies can be bonded to each other by free radical polymerization, so that a strong film can be formed.
所謂所述固體成分的總重量,意指著色劑組成物中除溶劑以外的成分的總重量之和。固體成分及各成分的以固體成分為基準的重量%的基準可藉由液相層析法或氣相層析法等本領域中所使用的通常的分析手段進行測定。 The total weight of the solid content means the sum of the total weight of the components other than the solvent in the colorant composition. The solid content and the basis of the weight % based on the solid content of each component can be measured by ordinary analytical means used in the art, such as liquid chromatography or gas chromatography.
根據本說明書的一實施形態,所述著色劑組成物可更包含選自由調平劑、抗氧化劑、接著助劑及界面活性劑所組成的群組中的一種以上。 According to one embodiment of the present specification, the colorant composition may further include at least one selected from the group consisting of a leveling agent, an antioxidant, an adjuvant, and a surfactant.
根據本說明書的一實施形態,所述著色劑組成物可更包含抗氧化劑。 According to an embodiment of the present specification, the colorant composition may further contain an antioxidant.
根據本說明書的一實施形態,以所述著色劑組成物中固體成分的總重量為基準,所述抗氧化劑的含量為0.1重量%至20重量%。 According to an embodiment of the present specification, the content of the antioxidant is 0.1% by weight to 20% by weight based on the total weight of the solid content in the colorant composition.
根據本說明書的一實施形態,所述著色劑組成物進一步包含選自由光交聯增感劑、硬化促進劑、接著助劑、密著促進劑、界面活性劑、熱聚合防止劑、紫外線吸收劑、分散劑及調平劑所組成的群組中的一種或兩種以上的添加劑。 According to one aspect of the present specification, the colorant composition further contains a photocrosslinking sensitizer, a curing accelerator, an adhesive adjuvant, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, and an ultraviolet absorber. One or more additives in the group consisting of , dispersant and leveling agent.
根據本說明書的一實施形態,以所述著色劑組成物中的固體成分的總重量為基準,所述添加劑的含量為0.1重量%至20重量%。 According to an embodiment of the present specification, the content of the additive is 0.1% by weight to 20% by weight based on the total weight of the solid content in the colorant composition.
所述光交聯增感劑可使用選自由以下化合物所組成的群組中的一種以上:二苯甲酮、4,4-雙(二甲基胺基)二苯甲酮、4,4- 雙(二乙基胺基)二苯甲酮、2,4,6-三甲基胺基二苯甲酮、鄰苯甲醯基苯甲酸甲酯、3,3-二甲基-4-甲氧基二苯甲酮、3,3,4,4-四(第三丁基過氧化羰基)二苯甲酮等二苯甲酮系化合物;9-芴酮、2-氯-9-芴酮、2-甲基-9-芴酮等芴酮系化合物;硫雜蒽酮、2,4-二乙基硫雜蒽酮、2-氯硫雜蒽酮、1-氯-4-丙基氧基硫雜蒽酮、異丙基硫雜蒽酮、二異丙基硫雜蒽酮等硫雜蒽酮系化合物;氧雜蒽酮、2-甲基氧雜蒽酮等氧雜蒽酮系化合物;蒽醌、2-甲基蒽醌、2-乙基蒽醌、第三丁基蒽醌、2,6-二氯-9,10-蒽醌等蒽醌系化合物;9-苯基吖啶、1,7-雙(9-吖啶基)庚烷、1,5-雙(9-吖啶基戊烷)、1,3-雙(9-吖啶基)丙烷等吖啶系化合物;苄基、1,7,7-三甲基-雙環[2,2,1]庚烷-2,3-二酮、9,10-菲醌等二羰基化合物;2,4,6-三甲基苯甲醯基二苯基氧化膦、雙(2,6-二甲氧基苯甲醯基)-2,4,4-三甲基戊基氧化膦等氧化膦系化合物;4-(二甲基胺基)苯甲酸甲酯、4-(二甲基胺基)苯甲酸乙酯、2-正丁氧基乙基-4-(二甲基胺基)苯甲酸酯等苯甲酸酯系化合物;2,5-雙(4-二乙基胺基亞苄基)環戊酮、2,6-雙(4-二乙基胺基亞苄基)環己酮、2,6-雙(4-二乙基胺基亞苄基)-4-甲基-環戊酮等胺基增效劑;3,3-羰基乙烯基-7-(二乙基胺基)香豆素、3-(2-苯並噻唑基)-7-(二乙基胺基)香豆素、3-苯甲醯基-7-(二乙基胺基)香豆素、3-苯甲醯基-7-甲氧基-香豆素、10,10-羰基雙[1,1,7,7-四甲基-2,3,6,7-四氫-1H,5H,11H-C1]-苯並吡喃並[6,7,8-ij]-喹嗪-11-酮等香豆素系化合物;4-二乙基胺基查耳酮、4-疊氮基亞苄基苯乙酮等查耳酮化合物;2-苯甲醯基亞甲基、3-甲基-b-萘並噻唑啉。 The photocrosslinking sensitizer can use one or more selected from the group consisting of the following compounds: benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4- Bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl o-benzoylbenzoate, 3,3-dimethyl-4-methyl Oxybenzophenone, 3,3,4,4-tetrakis(tert-butylcarbonyl peroxide)benzophenone and other benzophenone compounds; 9-fluorenone, 2-chloro-9-fluorenone , Fluorenone compounds such as 2-methyl-9-fluorenone; thioxanthone-based compounds such as thioxanthone, isopropylthioxanthone, and diisopropylthioxanthone; xanthone-based compounds such as xanthone and 2-methylxanthone ;Anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tert-butylanthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine , 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridylpentane), 1,3-bis(9-acridinyl)propane and other acridine-based compounds; Benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, 9,10-phenanthrenequinone and other dicarbonyl compounds; 2,4,6-trimethyl Phosphine oxide compounds such as benzalkonium diphenylphosphine oxide and bis(2,6-dimethoxybenzyl)-2,4,4-trimethylpentylphosphine oxide; Benzoic acids such as methylamino)benzoate, ethyl 4-(dimethylamino)benzoate, 2-n-butoxyethyl-4-(dimethylamino)benzoate Ester compounds; 2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylidene)cyclohexanone, 2,6- Amine synergists such as bis(4-diethylaminobenzylidene)-4-methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzyl-7-(diethylamino)coumarin, 3-benzylamino)coumarin -7-Methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]- Coumarin-based compounds such as benzopyrano[6,7,8-ij]-quinazin-11-one; 4-diethylaminochalcone, 4-azidobenzylidene acetophenone and other chalcone compounds; 2-benzyl methylene, 3-methyl-b-naphthothiazoline.
所述硬化促進劑用於提高硬化及機械強度,具體而言,可使用選自由2-巰基苯並咪唑、2-巰基苯並噻唑、2-巰基苯並噁唑、2,5-二巰基-1,3,4-噻二唑、2-巰基-4,6-二甲基胺基吡啶、季戊四醇-四(3-巰基丙酸酯)、季戊四醇-三(3-巰基丙酸酯)、季戊四醇-四(2-巰基乙酸酯)、季戊四醇-三(2-巰基乙酸酯)、三羥甲基丙烷-三(2-巰基乙酸酯)及三羥甲基丙烷-三(3-巰基丙酸酯)所組成的群組中的一種以上。 The hardening accelerator is used to improve hardening and mechanical strength. Specifically, it can be selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis(3-mercaptopropionate), pentaerythritol-tris(3-mercaptopropionate), pentaerythritol -Tetrakis(2-mercaptoacetate), Pentaerythritol-tris(2-mercaptoacetate), Trimethylolpropane-tris(2-mercaptoacetate) and Trimethylolpropane-tris(3-mercaptoacetate) one or more of the group consisting of propionate).
作為本說明書中所使用的密著促進劑,可使用選自甲基丙烯醯氧基丙基三甲氧基矽烷、甲基丙烯醯氧基丙基二甲氧基矽烷、甲基丙烯醯氧基丙基三乙氧基矽烷、甲基丙烯醯氧基丙基二甲氧基矽烷等甲基丙烯醯基矽烷偶合劑中的一種以上,作為烷基三甲氧基矽烷,可使用選自辛基三甲氧基矽烷、十二烷基三甲氧基矽烷、十八烷基三甲氧基矽烷等中的一種以上。 As the adhesion promoter used in this specification, one selected from the group consisting of methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, and methacryloyloxypropyl can be used. One or more of methacryloyl silane coupling agents such as methacrylotriethoxysilane, methacryloyloxypropyldimethoxysilane, etc. As the alkyltrimethoxysilane, one selected from the group consisting of octyltrimethoxysilane can be used. One or more of alkoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc.
所述界面活性劑為矽系界面活性劑或氟系界面活性劑,具體而言,矽系界面活性劑可使用畢克化學(BYK-Chemie)公司的畢克(BYK)-077、畢克(BYK)-085、畢克(BYK)-300、畢克(BYK)-301、畢克(BYK)-302、畢克(BYK)-306、畢克(BYK)-307、畢克(BYK)-310、畢克(BYK)-320、畢克(BYK)-322、畢克(BYK)-323、畢克(BYK)-325、畢克(BYK)-330、畢克(BYK)-331、畢克(BYK)-333、畢克(BYK)-335、畢克(BYK)-341v344、畢克(BYK)-345v346、畢克(BYK)-348、畢克(BYK)-354、畢克(BYK)-355、畢克(BYK)-356、畢克 (BYK)-358、畢克(BYK)-361、畢克(BYK)-370、畢克(BYK)-371、畢克(BYK)-375、畢克(BYK)-380、畢克(BYK)-390等,作為氟系界面活性劑,可使用迪愛生(DIC)(大日本油墨化學工業股份有限公司(DaiNippon Ink & Chemicals))公司的F-114、F-177、F-410、F-411、F-450、F-493、F-494、F-443、F-444、F-445、F-446、F-470、F-471、F-472SF、F-474、F-475、F-477、F-478、F-479、F-480SF、F-482、F-483、F-484、F-486、F-487、F-172D、MCF-350SF、TF-1025SF、TF-1117SF、TF-1026SF、TF-1128、TF-1127、TF-1129、TF-1126、TF-1130、TF-1116SF、TF-1131、TF1132、TF1027SF、TF-1441、TF-1442等,但並不僅限定於此。 The surfactant is a silicon-based surfactant or a fluorine-based surfactant. Specifically, the silicon-based surfactant can be BYK-077 and BYK-077 from BYK-Chemie. BYK)-085, BYK(BYK)-300, BYK(BYK)-301, BYK(BYK)-302, BYK(BYK)-306, BYK(BYK)-307, BYK(BYK) -310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331 , BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK Gram (BYK)-355, Peak (BYK)-356, Peak (BYK)-358, BYK(BYK)-361, BYK(BYK)-370, BYK(BYK)-371, BYK(BYK)-375, BYK(BYK)-380, BYK(BYK) ) -390, as a fluoride interface active agent, can use F-114, F-177, F-410, F of DIC Erison (DIC) Ink Chemical Industry Co., Ltd. (DIC). -411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475 , F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF -1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc., but not Not limited to this.
作為所述抗氧化劑,可為選自由受阻酚(Hindered phenol)系抗氧化劑、胺系抗氧化劑、硫系抗氧化劑及膦系抗氧化劑所組成的群組中的一種以上,但並不僅限定於此。 The antioxidant may be one or more selected from the group consisting of hindered phenol-based antioxidants, amine-based antioxidants, sulfur-based antioxidants, and phosphine-based antioxidants, but is not limited thereto .
作為所述抗氧化劑的具體例,可列舉:如磷酸、磷酸三甲酯或磷酸三乙酯等磷酸系熱穩定劑;如2,6-二-第三丁基-對甲酚、十八烷基-3-(4-羥基-3,5-二-第三丁基苯基)丙酸酯、四雙[亞甲基-3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]甲烷、1,3,5-三甲基-2,4,6-三(3,5-二-第三丁基-4-羥基苄基)苯、3,5-二-第三丁基-4-羥基苄基亞磷酸二乙酯、2,2-硫代雙(4-甲基-6-第三丁基苯酚)、2,6-g,t-丁基苯酚4,4'-亞丁基-雙(3-甲基-6-第三丁基苯酚)、4,4'-硫代雙(3-甲基-6-第三丁基苯酚)或雙[3,3-雙-(4'-羥基-3'-第三丁基苯 基)丁酸]二醇酯(Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol ester)等受阻酚(Hindered phenol)系一次抗氧化劑;如苯基-α-萘基胺、苯基-β-萘基胺、N,N'-二苯基-對苯二胺或N,N'-二-β-萘基-對苯二胺等胺系二次抗氧化劑;二月桂基二硫化物、二月桂基硫代丙酸酯、二硬脂基硫代丙酸酯、巰基苯並噻唑或四甲基秋蘭姆二硫化物四雙[亞甲基-3-(月桂基硫代)丙酸酯]甲烷等硫(Thio)系二次抗氧化劑;或者如三苯基亞磷酸酯、三(壬基苯基)亞磷酸酯、三異癸基亞磷酸酯、雙(2,4-二丁基苯基)季戊四醇二亞磷酸酯(Bis(2,4-ditbutylphenyl)Pentaerythritol Diphosphite)或(1,1'-聯苯基)-4,4'-二基雙亞膦酸四[2,4-雙(1,1-二甲基乙基)苯基]酯((1,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl]ester)等亞磷酸酯系二次抗氧化劑。 Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate, and triethyl phosphate; yl-3-(4-hydroxy-3,5-di-tert-butylphenyl)propionate, tetrabis[methylene-3-(3,5-di-tert-butyl-4-hydroxyl) phenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 3,5- Di-tert-butyl-4-hydroxybenzyl diethyl phosphite, 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-g,t-butyl Phenol 4,4'-butylene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or bis[ 3,3-bis-(4'-hydroxy-3'-tert-butylbenzene Hindered phenols such as Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol ester are primary antioxidants; such as phenyl - Amines such as α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-di-β-naphthyl-p-phenylenediamine Secondary antioxidants; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene -3-(lauryl thio) propionate] methane and other sulfur (Thio) secondary antioxidants; or triphenyl phosphite, tris(nonylphenyl) phosphite, triisodecyl phosphite Phosphate, Bis(2,4-dibutylphenyl)Pentaerythritol Diphosphite, or (1,1'-biphenyl)-4,4'-diphosphite (1,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis[2,4- Phosphite-based secondary antioxidants such as bis(1,1-dimethylethyl)phenyl]ester).
具體而言,作為所述抗氧化劑可使用松諾科(Songnox)1010,但並不限定於此。 Specifically, as the antioxidant, Songnox 1010 can be used, but it is not limited to this.
作為所述紫外線吸收劑,可使用2-(3-第三丁基-5-甲基-2-羥基苯基)-5-氯-苯並三唑、烷氧基二苯甲酮等,並不限定於此,本領域中通常所使用者均能夠使用。 As the ultraviolet absorber, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, etc. can be used, and It is not limited to this, and it can be used by the user normally in this field.
作為所述熱聚合防止劑,例如可包含選自由對苯甲醚、對苯二酚、鄰苯二酚(pyrocatechol)、第三丁基兒茶酚(t-butyl catechol)、N-亞硝基苯基羥基胺銨鹽、N-亞硝基苯基羥基胺鋁鹽、 對甲氧基苯酚、二-第三丁基-對甲酚、鄰苯三酚、苯醌、4,4-硫代雙(3-甲基-6-第三丁基酚)、2,2-亞甲基雙(4-甲基-6-第三丁基苯酚)、2-巰基咪唑及啡噻嗪(phenothiazine)所組成的群組中的一種以上,但並不僅限定於該些,亦可包含本技術領域中通常已知者。 The thermal polymerization inhibitor may contain, for example, a group selected from p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitroso Phenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis(3-methyl-6-tert-butylphenol), 2,2 - One or more of the group consisting of methylene bis(4-methyl-6-tert-butylphenol), 2-mercaptoimidazole and phenothiazine, but not limited to these, but also Those commonly known in the art may be included.
所述分散劑可以以下方法來使用:以預先對顏料進行表面處理的形態內部添加於顏料中的方法或者外部添加於顏料中的方法。作為所述分散劑,可使用化合物型、非離子性、陰離子性或陽離子性分散劑,可列舉氟系、酯系、陽離子系、陰離子系、非離子系、兩性界面活性劑等。該些可分別使用或將兩種以上組合使用。 The dispersing agent can be used by a method of adding it internally to a pigment in a form in which the pigment is surface-treated in advance, or a method of adding it externally to a pigment. As the dispersing agent, compound-type, nonionic, anionic or cationic dispersing agents can be used, and examples thereof include fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, and amphoteric surfactants. These may be used individually or in combination of two or more.
具體而言,所述分散劑可有選自由聚烷二醇及其酯、聚氧伸烷基多元醇、酯環氧烷加成物、醇環氧烷加成物、磺酸酯、磺酸鹽、羧酸酯、羧酸鹽、烷基醯胺環氧烷加成物及烷基胺所組成的群組中的一種以上,但並不限定於此。 Specifically, the dispersing agent may be selected from polyalkylene glycols and their esters, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid One or more of the group consisting of salt, carboxylate, carboxylate, alkylamide alkylene oxide adduct and alkylamine, but not limited to this.
所述調平劑可為聚合物性或非聚合物性。作為聚合物性的調平劑的具體例,可列舉聚乙烯亞胺、聚醯胺胺、胺與環氧化物的反應產物,作為非聚合物性的調平劑的具體例,包含非聚合物含硫化合物及非聚合物含氮化合物,但不限定於此,本領域中通常所使用者均能夠使用。 The leveling agent can be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamide amines, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-containing Compounds and non-polymer nitrogen-containing compounds are not limited to these, and can be used by any user in the art.
所述調平劑具體而言可為F-554,但並不限定於此。 Specifically, the leveling agent may be F-554, but is not limited thereto.
作為所述接著助劑,可使用KBM-503,但並不限定於 此,本領域中通常所使用者均能夠使用。 As the adhesive agent, KBM-503 can be used, but it is not limited to Therefore, it can be used by any general user in this field.
根據本說明書的一實施形態,提供一種由所述著色劑組成物製備而成的光阻。 According to one embodiment of the present specification, there is provided a photoresist prepared from the colorant composition.
更詳細而言,可利用適當的方法將本說明書的著色劑組成物塗佈至基材上來形成薄膜或圖案形態的光阻。 In more detail, the coloring agent composition of this specification can be apply|coated to a base material by an appropriate method, and the photoresist of a film or pattern form can be formed.
作為所述塗佈方法,雖並不特別限定,但可使用噴霧法、輥塗法、旋塗法等,通常廣泛使用旋塗法。另外,於形成塗佈膜之後,視情況,亦可於減壓下去除一部分殘留溶劑。 Although the coating method is not particularly limited, a spray method, a roll coating method, a spin coating method, or the like can be used, and generally, a spin coating method is widely used. In addition, after forming the coating film, a part of residual solvent may be removed under reduced pressure as the case may be.
作為用於對本說明書的著色劑組成物進行硬化的光源,例如有使波長為250nm至450nm的光發散的水銀蒸汽弧(arc)、碳弧、氙(Xe)弧等,但未必侷限於此。 Examples of light sources for curing the colorant composition of the present specification include, but are not necessarily limited to, mercury vapor arc (arc), carbon arc, and xenon (Xe) arc that emit light having a wavelength of 250 nm to 450 nm.
本說明書的著色劑組成物可用於薄膜電晶體液晶顯示裝置(Thin Film Transistor Liquid Crystal Display,TFT LCD)彩色濾光片製造用顏料分散型光阻、薄膜電晶體液晶顯示裝置(TFT LCD)或有機發光二極體的黑色矩陣形成用光阻、外塗層形成用光阻、柱狀間隔物(colomn spacer)光阻、光硬化型塗料、光硬化性墨水、光硬化性接著劑、印刷版、印刷配線板用光阻、電漿顯示器面板(Plasma Display Panel,PDP)用光阻等,其用途並無特別限制。 The colorant composition of the present specification can be used in a pigment dispersion type photoresist for the manufacture of a thin film transistor liquid crystal display (TFT LCD) color filter, a thin film transistor liquid crystal display (TFT LCD) or an organic Photoresist for black matrix formation of light-emitting diode, photoresist for overcoat layer formation, photoresist for column spacer, photocurable paint, photocurable ink, photocurable adhesive, printing plate, The photoresist for printed wiring boards, the photoresist for plasma display panels (PDP), and the like are not particularly limited in use.
根據本說明書的一實施形態,提供一種包含所述光阻的彩色濾光片。 According to an embodiment of the present specification, a color filter including the photoresist is provided.
所述彩色濾光片可利用包含含有所述三芳基甲烷染料單體、 (甲基)丙烯酸單體、由下述化學式1表示的結構的化合物的著色劑組成物製備而成。將所述著色劑組成物塗佈於基板上,形成塗佈(coating)膜,對所述塗佈膜進行曝光、顯影及硬化,藉此可形成彩色濾光片。 The color filter can utilize the dye monomer containing the triarylmethane, The (meth)acrylic monomer is prepared from a colorant composition of a compound having a structure represented by the following chemical formula 1. A color filter can be formed by applying the colorant composition on a substrate to form a coating film, and exposing, developing, and curing the coating film.
所述基板可為玻璃板、矽晶圓及聚醚碸(Polyethersulfone,PES)、聚碳酸酯(Polycarbonate,PC)等塑膠基材的板等,其種類並無特別限制。 The substrate may be a glass plate, a silicon wafer, a plastic substrate such as polyethersulfone (PES), polycarbonate (PC) or the like, and the types thereof are not particularly limited.
所述彩色濾光片可包含紅色圖案、綠色圖案、藍色圖案、黑色矩陣。 The color filter may include a red pattern, a green pattern, a blue pattern, a black matrix.
根據又一實施形態,所述彩色濾光片可更包含外塗層。 According to yet another embodiment, the color filter may further include an overcoat.
於彩色濾光片的彩色畫素之間,為了提升對比度,可配置被稱為黑色矩陣的格子狀的黑色圖案。作為黑色矩陣的材料,可使用鉻。該情況下,可利用以下方式:使鉻蒸鍍於玻璃基板整體上,並藉由蝕刻處理來形成圖案。但是,考慮到製程上的高成本、鉻的高反射率、由鉻的廢液引起的環境污染,亦可使用利用能夠進行微細加工的顏料分散法的樹脂黑色矩陣。 Between the color pixels of the color filter, a lattice-like black pattern called a black matrix can be arranged in order to improve the contrast. As the material of the black matrix, chrome can be used. In this case, it is possible to use a method in which chromium is vapor-deposited on the entire glass substrate, and a pattern is formed by etching. However, considering the high cost in the manufacturing process, the high reflectivity of chromium, and the environmental pollution caused by the waste liquid of chromium, a resin black matrix using a pigment dispersion method capable of fine processing can also be used.
本說明書的一實施形態的黑色矩陣可使用黑色顏料或黑色染料作為顏色材料。例如可單獨使用碳黑,或者將碳黑與著色顏料混合使用,此時,由於將遮光性不足的著色顏料加以混合,故而有如下優點:即使顏色材料的量相對增加,膜的強度或者對基板的密著性亦不會降低。 The black matrix of one Embodiment of this specification can use a black pigment or a black dye as a color material. For example, carbon black may be used alone, or carbon black may be used in combination with a coloring pigment. In this case, since the coloring pigment having insufficient light-shielding properties is mixed, there are the following advantages. The adhesion will not be reduced.
本說明書提供一種包含本說明書的彩色濾光片的顯示 裝置。 This specification provides a display including the color filter of this specification device.
所述顯示裝置可為電漿顯示器面板(Plasma Display Panel,PDP)、發光二極體(Light Emitting Diode,LED)、有機發光元件(Organic Light Emitting Diode,OLED)、液晶顯示裝置(Liquid Crystal Display,LCD)、薄膜電晶體液晶顯示裝置(Thin Film Transistor-Liquid Crystal Display,LCD-TFT)以及陰極射線管(Cathode Ray Tube,CRT)中的任一者。 The display device can be a Plasma Display Panel (PDP), a Light Emitting Diode (LED), an Organic Light Emitting Diode (OLED), a Liquid Crystal Display (Liquid Crystal Display, Any of LCD), Thin Film Transistor-Liquid Crystal Display (LCD-TFT) and Cathode Ray Tube (CRT).
以下,為了對本說明書進行具體說明,列舉實施例來詳細地說明。但是,本說明書的實施例可變形為各種其他形態,本說明書的範圍並不解釋為限定於以下記述的實施例。本說明書的實施例是為了對本領域中有平均知識者更完整地說明本說明書而提供的。 Hereinafter, in order to demonstrate this specification concretely, an Example is given and demonstrated in detail. However, the examples of the present specification can be modified into various other forms, and the scope of the present specification should not be interpreted as being limited to the examples described below. The examples in this specification are provided to more completely explain this specification to those of ordinary skill in the art.
<實施例> <Example>
<化合物的合成實施例> <Synthesis Examples of Compounds>
1.中間體化合物的合成 1. Synthesis of intermediate compounds
(1)[化學式1-1]化合物的合成 (1) Synthesis of compound of [Chemical formula 1-1]
向0.220mol(53g,1eq)的N-(4-羥基環己基)-1-萘胺、0.242mol(1.1eq)的三乙基胺添加50mL的二氯甲烷,攪拌並溶解。 此後,添加0.242mol(20.8g,1.1eq)甲基丙烯酸酐,升溫至40℃並保持。攪拌約6小時的持續時間後,添加蒸餾水來分離有機層。進一步添加20mL飽和氯化鈉溶液攪拌後,攪拌30分鐘的持續時間。層分離後對有機層進行減壓乾燥,進行精製得到0.17mol、53g的[化學式1-1](產率77%)。 To 0.220 mol (53 g, 1 eq) of N-(4-hydroxycyclohexyl)-1-naphthylamine and 0.242 mol (1.1 eq) of triethylamine was added 50 mL of dichloromethane, stirred and dissolved. Thereafter, 0.242 mol (20.8 g, 1.1 eq) of methacrylic anhydride was added, and the temperature was raised to 40°C and maintained. After stirring for a duration of about 6 hours, distilled water was added to separate the organic layer. After stirring a further 20 mL of saturated sodium chloride solution, stirring was carried out for a duration of 30 minutes. After layer separation, the organic layer was dried under reduced pressure and purified to obtain 0.17 mol and 53 g of [Chemical Formula 1-1] (yield: 77%).
(2)[化學式1-2]化合物的製備 (2) Preparation of compound of [Chemical formula 1-2]
使用0.220mol(53g,1eq)的4-(異喹啉-5-基胺基)環己-1-醇與0.242mol(20.8g,1.1eq)的甲基丙烯酸酐,以與[化學式1-1]相同的方法進行製備,得到0.15mol,46.5g的[化學式1-2]化合物(產率68%)。 Use 0.220mol (53g, 1eq) of 4-(isoquinolin-5-ylamino)cyclohexan-1-ol and 0.242mol (20.8g, 1.1eq) of methacrylic anhydride to react with [chemical formula 1- 1] The same method was carried out to obtain 0.15 mol, 46.5 g of the compound of [Chemical formula 1-2] (yield 68%).
離子化模式:大氣壓化學遊離(Atmospheric Pressure Chemical Ionization,APCI)+:m/z=308[M+H]+,準確質量(Exact Mass):308 Ionization mode: Atmospheric Pressure Chemical Ionization (APCI)+: m/z=308[M+H]+, Exact Mass: 308
(3)[化學式1-3]化合物的製備 (3) Preparation of compound of [Chemical formula 1-3]
在氮環境下,向燒瓶加入0.06mol(15g,1eq)的4,4-二氟 二苯甲酮與0.29mol(40g,5eq)的N-異丙基苯胺,並在常溫下攪拌約48小時的持續時間。反應完成後加入蒸餾水並添加50mL飽和氯化鈉溶液來分離有機層。層分離後對有機層進行減壓乾燥,利用管柱層析法進行精製得到15g(0.03mol)的(二氯甲烷:甲醇=15:1)[化學式1-3](產率50%)。 Under nitrogen, add 0.06 mol (15 g, 1 eq) of 4,4-difluoro to the flask Benzophenone with 0.29 mol (40 g, 5 eq) of N-isopropylaniline and stirred at ambient temperature for a duration of about 48 hours. After completion of the reaction, distilled water was added and 50 mL of saturated sodium chloride solution was added to separate the organic layer. After layer separation, the organic layer was dried under reduced pressure and purified by column chromatography to obtain 15 g (0.03 mol) of (dichloromethane:methanol=15:1) [chemical formula 1-3] (yield 50%).
離子化模式:APCI+:m/z=448[M+H]+,準確質量(Exact Mass):448 Ionization mode: APCI+: m/z=448[M+H]+, Exact Mass: 448
(4)[化學式1-4]化合物的製備 (4) Preparation of compound of [Chemical formula 1-4]
向100g甲苯添加0.249mol(48g,1eq)的N,N-二乙胺基苯甲酸並攪拌。此後,滴加0.4mol(47g,1.6eq)亞硫醯氯後,升溫至80℃後,反應1小時。反應後,進行減壓蒸餾去除亞硫醯氯與甲苯,得到N,N-二乙基胺基苯甲醯氯。將0.31mmol(0.04g)的無水氯化鋁與120g的二氯乙烷攪拌,冷卻並保持為5℃以下。將前文得到的N,N-二乙基胺基苯甲醯氯溶解於120g的二氯乙烷,並於滴加之後攪拌30分鐘。將0.249mol(40.6g)的N,N-二乙基甲基甲苯胺滴加至反應溶液後,於常溫下攪拌4小時。投入冰水完成反應後,投入氫氧化鈉溶液至pH11以上,之後藉由矽藻土(celite)過濾並去除不溶成分。對層分離得到的有機層進行 減壓濃縮並利用管柱層析法精製,得到0.075mol(25.4g)的(二氯甲烷:甲醇=10:1)[化學式1-4](產率30%)。 To 100 g of toluene was added 0.249 mol (48 g, 1 eq) of N,N-diethylaminobenzoic acid and stirred. Then, after adding dropwise 0.4 mol (47 g, 1.6 eq) of thionium chloride, the temperature was raised to 80°C, and the reaction was carried out for 1 hour. After the reaction, thionite chloride and toluene were removed by distillation under reduced pressure to obtain N,N-diethylaminobenzyl chloride. 0.31 mmol (0.04 g) of anhydrous aluminum chloride was stirred with 120 g of dichloroethane, cooled and kept at 5°C or lower. The N,N-diethylaminobenzyl chloride obtained above was dissolved in 120 g of dichloroethane, and after the dropwise addition, the mixture was stirred for 30 minutes. 0.249 mol (40.6 g) of N,N-diethylmethyltoluidine was added dropwise to the reaction solution, followed by stirring at normal temperature for 4 hours. After adding ice water to complete the reaction, adding sodium hydroxide solution to pH 11 or higher, and then filtering through celite to remove insoluble components. The organic layer obtained by layer separation was subjected to It was concentrated under reduced pressure and purified by column chromatography to obtain 0.075 mol (25.4 g) of (dichloromethane:methanol=10:1) [Chemical formula 1-4] (yield 30%).
離子化模式:APCI+:m/z=338[M+H]+,準確質量(Exact Mass):338 Ionization mode: APCI+: m/z=338[M+H]+, Exact Mass: 338
(5)[化學式1-5]化合物的製備 (5) Preparation of compound of [Chemical formula 1-5]
向140g氯仿添加0.03mol(13.4g,1eq)的[化學式1-3]化合物並攪拌。之後添加0.045mol(6.9g,1.5eq)的氧氯化磷,並攪拌約15分鐘。投入0.001mol的4-甲氧基苯酚(4-Methoxy phenol)與0.03mol(9.3g,1eq)的[化學式1-1],並將溫度升至60℃並回流4小時。反應完成後,冷卻至常溫並進一步添加蒸餾水後進行攪拌。層分離後進行減壓濃縮,並利用管柱層析法對所得的化合物進行精製,得到0.025mol、19.4g的(二氯甲烷:甲醇:乙酸乙酯=6:1:2)[化學式1-5](產率83%)。 To 140 g of chloroform, 0.03 mol (13.4 g, 1 eq) of the compound of [Chemical formula 1-3] was added and stirred. Then 0.045 mol (6.9 g, 1.5 eq) of phosphorus oxychloride was added and stirred for about 15 minutes. 0.001 mol of 4-Methoxy phenol and 0.03 mol (9.3 g, 1 eq) of [Chemical formula 1-1] were put in, and the temperature was raised to 60° C. and refluxed for 4 hours. After completion of the reaction, the mixture was cooled to normal temperature and further added with distilled water, followed by stirring. The layers were separated and concentrated under reduced pressure, and the resulting compound was purified by column chromatography to obtain 0.025 mol, 19.4 g of (dichloromethane:methanol:ethyl acetate=6:1:2) [chemical formula 1- 5] (83% yield).
離子化模式:APCI+:m/z=740[M+H]+,準確質量(Exact Mass):740 Ionization mode: APCI+: m/z=740[M+H]+, Exact Mass: 740
(6)[化學式1-6]化合物的製備 (6) Preparation of compound of [Chemical formula 1-6]
除添加0.03mol(13.4g,1eq)的[化學式1-3]與0.03mol(9.3g,1eq)的[化學式1-2]之外,以與[化學式1-5]相同的方法進行製備,得到0.02mol、15.5g的[化學式1-6](產率66.7%)。 Prepared in the same manner as [Chemical formula 1-5] except adding 0.03 mol (13.4 g, 1 eq) of [Chemical formula 1-3] and 0.03 mol (9.3 g, 1 eq) of [Chemical formula 1-2], 0.02 mol, 15.5 g of [Chemical Formula 1-6] were obtained (yield 66.7%).
離子化模式:APCI+:m/z=741[M+H]+,準確質量(Exact Mass):741 Ionization mode: APCI+: m/z=741[M+H]+, Exact Mass: 741
(7)[化學式1-7]化合物的製備 (7) Preparation of compound of [Chemical formula 1-7]
除添加0.03mol(10.1g,1eq)的[化學式1-4]與0.03mol(9.3g,1eq)的[化學式1-1]之外,以與[化學式1-5]相同的方法進行製備,得到0.023mol、15.3g的[化學式1-7](產率76.7%)。 Prepared in the same manner as [Chemical formula 1-5] except adding 0.03 mol (10.1 g, 1 eq) of [Chemical formula 1-4] and 0.03 mol (9.3 g, 1 eq) of [Chemical formula 1-1], 0.023 mol, 15.3 g of [Chemical formula 1-7] were obtained (yield 76.7%).
離子化模式:APCI+:m/z=630[M+H]+,準確質量(Exact Mass):630 Ionization mode: APCI+: m/z=630[M+H]+, Exact Mass: 630
2.三芳基甲烷藍色染料化合物的合成 2. Synthesis of triarylmethane blue dye compounds
(1)合成例1:[化學式I]的合成 (1) Synthesis Example 1: Synthesis of [Chemical Formula I]
將0.01mol(7.8g)的[化學式1-5]化合物溶解於50g的甲醇(MeOH)後,將0.011mol的雙三氟甲烷磺醯亞胺鋰添加到20%水溶液來取代鹽。過濾後,將所得到的化合物溶解於氯仿後,利用水進行清洗並減壓濃縮得到0.009mol、9.2g的[化學式I](產率90%)。 After dissolving 0.01 mol (7.8 g) of the compound of [Chemical formula 1-5] in 50 g of methanol (MeOH), 0.011 mol of lithium bistrifluoromethanesulfonimide was added to a 20% aqueous solution to replace the salt. After filtration, the obtained compound was dissolved in chloroform, washed with water, and concentrated under reduced pressure to obtain 0.009 mol, 9.2 g of [chemical formula I] (yield 90%).
離子化模式:APCI+:m/z=740[M+H]+,準確質量(Exact Mass):740 Ionization mode: APCI+: m/z=740[M+H]+, Exact Mass: 740
(2)合成例2:[化學式II]的合成 (2) Synthesis Example 2: Synthesis of [Chemical Formula II]
添加0.01mol、7.7g的[化學式1-6]化合物,以與合成例1相同的方式進行製備,得到0.008mol、10.2g的[化學式II](產率80%)。 0.01 mol, 7.7 g of the compound of [Chemical formula 1-6] was added, and the preparation was carried out in the same manner as in Synthesis Example 1 to obtain 0.008 mol, 10.2 g of [Chemical formula II] (yield 80%).
離子化模式:APCI+:m/z=741[M+H]+,準確質量(Exact Mass):741 Ionization mode: APCI+: m/z=741[M+H]+, exact mass (Exact Mass): 741
(3)化學式3:[化學式III]的合成 (3) Chemical formula 3: Synthesis of [Chemical formula III]
添加0.01mol、6.7g的[化學式1-7]化合物,以與合成例1相同的方式進行製備,得到0.0082mol、7.5g的[化學式III](產率82%)。 0.01 mol, 6.7 g of the compound of [Chemical formula 1-7] was added, and the preparation was carried out in the same manner as in Synthesis Example 1 to obtain 0.0082 mol, 7.5 g of [Chemical formula III] (yield 82%).
離子化模式:APCI+:m/z=630[M+H]+,準確質量(Exact Mass):630 Ionization mode: APCI+: m/z=630[M+H]+, Exact Mass: 630
3.三芳基甲烷高分子化合物的合成 3. Synthesis of triarylmethane polymer compounds
(合成例1)化合物A的合成 (Synthesis Example 1) Synthesis of Compound A
在50mL燒瓶中設置回流冷卻裝置,並在氮氣下,以要製備的化合物的總重量為基準分別以5重量%、20重量%、75重量%投入由化學式A-1結構表示的二苯甲酮甲基丙烯酸酯、甲基丙烯酸、以及由化學式I表示的染料後,使其與溶劑丙二醇單甲醚乙 酸酯與二丙酮醇1:1的混合液混合,並升溫至60℃。此後,以高分子總重量為基準,投入10重量份的熱聚合起始劑V-65(2,2-偶氮雙(2,4-二甲基戊腈)(2,2-Azobis(2,4-dimethylvaleronitrile))),回流16小時,完成聚合反應。得到數平均分子量為26,546、分散度為2.57的三芳基甲烷染料高分子化合物A。 A reflux cooling device was set in a 50 mL flask, and under nitrogen, the benzophenone represented by the structure of Chemical Formula A-1 was charged at 5 wt %, 20 wt %, and 75 wt % based on the total weight of the compound to be prepared, respectively. After methacrylate, methacrylic acid, and the dye represented by chemical formula I, make it with the solvent propylene glycol monomethyl ether ethyl A 1:1 mixture of acid ester and diacetone alcohol was mixed, and the temperature was raised to 60°C. Thereafter, 10 parts by weight of the thermal polymerization initiator V-65 (2,2-azobis(2,4-dimethylvaleronitrile)(2,2-Azobis(2,2-Azobis(2,2-Azobis(2,2-Azobis(2,2-Azobis(2,2-Azobis(2,2- ,4-dimethylvaleronitrile))), refluxed for 16 hours to complete the polymerization. A triarylmethane dye polymer compound A having a number average molecular weight of 26,546 and a dispersity of 2.57 was obtained.
(合成例2)化合物B的合成 (Synthesis Example 2) Synthesis of Compound B
以要製備的化合物的總重量為基準分別以10重量%、15重量%、75重量%投入由化學式A-1結構表示的二苯甲酮甲基丙烯酸酯、甲基丙烯酸、以及由化學式I表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為20,911、分散度為2.35的染料高分子化合物B。 Based on the total weight of the compound to be prepared, benzophenone methacrylate represented by the structure of Chemical Formula A-1, methacrylic acid, and benzophenone methacrylate represented by Chemical Formula The dye was prepared in the same manner as in Synthesis Example 1 to obtain a dye polymer compound B with a number-average molecular weight of 20,911 and a dispersity of 2.35.
(合成例3)化合物C的合成 (Synthesis Example 3) Synthesis of Compound C
以要製備的化合物的總重量為基準分別以5重量%、20重量%、75重量%投入由化學式A-2結構表示的苯甲醯苯基甲基丙烯醯胺、甲基丙烯酸、以及由化學式I表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為22,350、分散度為2.28的三芳基甲烷染料高分子化合物C。 Based on the total weight of the compound to be prepared, benzyl phenyl methacrylamide, methacrylic acid, and compounds represented by the chemical formula After the dye represented by I, it was prepared in the same manner as in Synthesis Example 1 to obtain a triarylmethane dye polymer compound C having a number average molecular weight of 22,350 and a dispersity of 2.28.
(合成例4)化合物D的合成 (Synthesis Example 4) Synthesis of Compound D
以要製備的化合物的總重量為基準分別以5重量%、20重量%、75重量%投入由化學式A-1結構表示的二苯甲酮甲基丙烯酸酯、甲基丙烯酸、以及由化學式II表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為26,879、分散度為2.69 的染料高分子化合物D。 Based on the total weight of the compound to be prepared, benzophenone methacrylate represented by the structure of Chemical Formula A-1, methacrylic acid, and benzophenone methacrylate represented by Chemical Formula The dye was prepared in the same manner as in Synthesis Example 1 to obtain a number-average molecular weight of 26,879 and a degree of dispersion of 2.69. The dye polymer compound D.
(合成例5)化合物E的合成 (Synthesis Example 5) Synthesis of Compound E
以要製備的化合物的總重量為基準分別以5重量%、20重量%、75重量%投入由化學式A-1結構表示的二苯甲酮甲基丙烯酸酯、甲基丙烯酸、以及由化學式III表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為24,369、分散度為2.55的染料高分子化合物E。 Based on the total weight of the compound to be prepared, benzophenone methacrylate represented by the structure of Chemical Formula A-1, methacrylic acid, and benzophenone methacrylate represented by Chemical Formula After the dye was obtained, it was prepared in the same manner as in Synthesis Example 1 to obtain a dye polymer compound E with a number average molecular weight of 24,369 and a dispersity of 2.55.
(合成例6)化合物F的合成 (Synthesis Example 6) Synthesis of Compound F
以要製備的化合物的總重量為基準分別以10重量%、25重量%、65重量%投入由化學式A-2結構表示的苯甲醯苯基甲基丙烯醯胺、甲基丙烯酸、以及由化學式II表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為31,250、分散度為2.97的三芳基甲烷染料高分子化合物F。 Based on the total weight of the compound to be prepared, 10% by weight, 25% by weight, 65% by weight of benzyl phenyl methacrylamide represented by the structure of Chemical Formula A-2, methacrylic acid, and chemical formula After the dye represented by II, it was prepared in the same manner as in Synthesis Example 1 to obtain a triarylmethane dye polymer compound F having a number average molecular weight of 31,250 and a dispersity of 2.97.
(合成例7)化合物G的合成 (Synthesis Example 7) Synthesis of Compound G
以要製備的化合物的總重量為基準分別以15重量%、25重量%、55重量%投入由化學式A-1結構表示的二苯甲酮甲基丙烯酸酯、甲基丙烯酸、以及由化學式III表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為30,956、分散度為2.88的三芳基甲烷染料高分子化合物G。 Based on the total weight of the compound to be prepared, benzophenone methacrylate represented by the structure of Chemical Formula A-1, methacrylic acid, and benzophenone methacrylate represented by Chemical Formula The dye was prepared in the same manner as in Synthesis Example 1 to obtain a triarylmethane dye polymer compound G with a number average molecular weight of 30,956 and a dispersity of 2.88.
(合成例8)化合物H的合成 (Synthesis Example 8) Synthesis of Compound H
以要製備的化合物的總重量為基準分別以5重量%、15重量%、15重量%、75重量%投入由化學式A-1結構表示的二苯甲酮 甲基丙烯酸酯、甲基丙烯酸、苯乙烯、以及由化學式II表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為21,287、分散度為2.39的染料高分子化合物H。 Based on the total weight of the compound to be prepared, the benzophenone represented by the structure of Chemical Formula A-1 was put in at 5% by weight, 15% by weight, 15% by weight, 75% by weight, respectively After methacrylate, methacrylic acid, styrene, and the dye represented by Chemical Formula II, the same method as in Synthesis Example 1 was carried out to obtain a dye polymer compound H having a number average molecular weight of 21,287 and a dispersity of 2.39.
(合成例9)化合物I的合成 (Synthesis Example 9) Synthesis of Compound I
以要製備的化合物的總重量為基準分別以5重量%、15重量%、10重量%、5重量%、70重量%投入由化學式A-1結構表示的二苯甲酮甲基丙烯酸酯、甲基丙烯酸、苯乙烯、甲基丙烯酸縮水甘油酯以及由化學式I表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為30,257、分散度為2.89的染料高分子化合物I。 Based on the total weight of the compound to be prepared, benzophenone methacrylate, methyl methacrylate and methyl methacrylate represented by the chemical formula After adding acrylic acid, styrene, glycidyl methacrylate and the dye represented by Chemical Formula I, it was prepared in the same manner as in Synthesis Example 1 to obtain a dye polymer compound I with a number average molecular weight of 30,257 and a dispersity of 2.89.
(合成例10)化合物J的合成 (Synthesis Example 10) Synthesis of Compound J
以要製備的化合物的總重量為基準分別以15重量%、10重量%、15重量%、60重量%投入甲基丙烯酸、苯乙烯、甲基丙烯酸縮水甘油酯以及由化學式I表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為28,775、分散度為2.92的染料高分子化合物J。 After adding methacrylic acid, styrene, glycidyl methacrylate and the dye represented by Chemical Formula I at 15% by weight, 10% by weight, 15% by weight, 60% by weight, respectively, based on the total weight of the compound to be prepared, It was prepared in the same manner as in Synthesis Example 1 to obtain a dye polymer compound J having a number average molecular weight of 28,775 and a dispersity of 2.92.
(合成例11)化合物K的合成 (Synthesis Example 11) Synthesis of Compound K
以要製備的化合物的總重量為基準分別以25重量%、75重量%投入甲基丙烯酸、以及由化學式I表示的染料後,以與合成例1相同的方法進行製備,得到數平均分子量為21,584、分散度為2.21的染料高分子化合物K。 Based on the total weight of the compound to be prepared, 25% by weight and 75% by weight of methacrylic acid and the dye represented by Chemical Formula I were added, and prepared in the same manner as in Synthesis Example 1 to obtain a number average molecular weight of 21,584. , Dye polymer compound K with a dispersity of 2.21.
所述分散度為多分散指數(Poly Dispersity Index, PDI),表示為重量平均分子量值除以數平均分子量的值。所述重量平均分子量及數平均分子量藉由高效液相層析(High Performance Liquid Chromatography,HPLC)分析來測定。 The degree of dispersion is the polydispersity index (Poly Dispersity Index, PDI), expressed as the value of the weight average molecular weight divided by the number average molecular weight. The weight average molecular weight and number average molecular weight are determined by High Performance Liquid Chromatography (HPLC) analysis.
[著色劑組成物實施例1的製備] [Preparation of Colorant Composition Example 1]
以著色劑組成物總重量100重量份為基準,將如下混合來製備實施例1:24.32重量份的所述化合物A、5.86重量份的黏合劑樹脂A、17.88重量份的黏合劑樹脂B、13.28重量份的多官能性單體二季戊四醇六丙烯酸酯、0.6重量份的調平劑F-554、0.07重量份的接著助劑KBM-503、0.88重量份的酚系抗氧化劑松諾科(Songnox)1010、0.87重量份的光起始劑SPI-03、22.87重量份的溶劑丙二醇單甲醚乙酸酯、以及13.37重量份的二丙酮醇。 Based on 100 parts by weight of the total weight of the colorant composition, Example 1 was prepared by mixing as follows: 24.32 parts by weight of the compound A, 5.86 parts by weight of the binder resin A, 17.88 parts by weight of the binder resin B, 13.28 parts by weight Parts by weight of multifunctional monomer dipentaerythritol hexaacrylate, 0.6 parts by weight of leveling agent F-554, 0.07 parts by weight of adhesive agent KBM-503, 0.88 parts by weight of phenolic antioxidant Songnox 1010, 0.87 parts by weight of photoinitiator SPI-03, 22.87 parts by weight of solvent propylene glycol monomethyl ether acetate, and 13.37 parts by weight of diacetone alcohol.
所述黏合劑樹脂A為如下共聚物:以黏合劑樹脂A的總重量為基準,甲基丙烯酸、縮水甘油基甲基丙烯酸、苯乙烯的含量分別為13重量%、52重量%、35重量%。 The binder resin A is the following copolymer: based on the total weight of the binder resin A, the contents of methacrylic acid, glycidyl methacrylic acid, and styrene are 13% by weight, 52% by weight, and 35% by weight, respectively. .
所述黏合劑樹脂B為如下共聚物:以黏合劑樹脂B的總重量為基準,甲基丙烯酸環己酯、甲基丙烯酸酯、甲基丙烯酸的含量分別為45重量%、30重量%、25重量%。 The binder resin B is the following copolymer: based on the total weight of the binder resin B, the contents of cyclohexyl methacrylate, methacrylate, and methacrylic acid are 45% by weight, 30% by weight, 25% by weight, respectively. weight%.
[著色劑組成物實施例2至實施例8的製備] [Preparation of Colorant Composition Examples 2 to 8]
除將著色劑組成物實施例1的化合物A分別應用為下述表1所記載的化合物之外,以與所述著色劑組成物實施例1相同的方法來製備著色劑組成物實施例2至實施例8。 The colorant composition examples 2 to 2 were prepared in the same manner as the colorant composition example 1 except that the compounds A of the colorant composition example 1 were respectively applied as the compounds described in the following table 1. Example 8.
[表1]
[著色劑組成物比較例1的製備] [Preparation of Colorant Composition Comparative Example 1]
除將著色劑組成物實施例1的化合物A改變為化合物J之外,以與著色劑組成物實施例1相同的方法來製備著色劑組成物比較例1。 Colorant Composition Comparative Example 1 was prepared in the same manner as in Colorant Composition Example 1, except that Compound A of Colorant Composition Example 1 was changed to Compound J.
[著色劑組成物比較例2的製備] [Preparation of Colorant Composition Comparative Example 2]
除將著色劑組成物實施例1的化合物A改變為化合物K之外,以與著色劑組成物實施例1相同的方法來製備著色劑組成物比較例2。 Colorant Composition Comparative Example 2 was prepared in the same manner as in Colorant Composition Example 1, except that Compound A of Colorant Composition Example 1 was changed to Compound K.
[著色劑組成物比較例3的製備] [Preparation of Colorant Composition Comparative Example 3]
除將著色劑組成物比較例2中的0.77重量份的起始劑SPI-03的含量改變為0.10重量份的由化學式A-1結構表示的二苯甲酮甲基丙烯酸酯之外,以相同的方法進行製備,從而製備著色劑組成物比較例3。 Except changing the content of 0.77 parts by weight of the initiator SPI-03 in the colorant composition Comparative Example 2 to 0.10 parts by weight of the benzophenone methacrylate represented by the structure of Chemical Formula A-1, the same prepared by the method of 1 to 3 to prepare the colorant composition Comparative Example 3.
[著色劑組成物比較例4的製備] [Preparation of Colorant Composition Comparative Example 4]
除將著色劑組成物比較例2中的0.77重量份的起始劑SPI-03的含量改變為0.10重量份的由化學式A-2結構表示的苯甲醯苯基甲基丙烯醯胺之外,以相同的方法進行製備,從而製備著色劑組成物比較例4。 Except that the content of 0.77 parts by weight of the initiator SPI-03 in the colorant composition Comparative Example 2 was changed to 0.10 parts by weight of benzylphenyl methacrylamide represented by the structure of Chemical Formula A-2, The preparation was carried out in the same manner to prepare a colorant composition Comparative Example 4.
實驗例 Experimental example
[基板製作] [Substrate production]
將藉由所述實施例1至實施例8及比較例1至比較例4製備的著色劑組成物旋塗(spin coating)於玻璃(5cm×5cm)上,於105℃下實施70秒預熱處理(預烘(Prebake))而形成膜。利用光罩(photo mask)於高壓水銀燈下以40mJ/cm2的能量對所述膜進行曝光後,利用KOH鹼水溶液對圖案進行顯影,並用蒸餾水清洗。去除蒸餾水後以240℃實施20分鐘後熱處理(後烘(Postbake))而得到彩色圖案。 The colorant compositions prepared by the above-mentioned Examples 1 to 8 and Comparative Examples 1 to 4 were spin-coated on glass (5cm×5cm), and preheated at 105°C for 70 seconds Process (Prebake) to form a film. After exposing the film under a high pressure mercury lamp with an energy of 40 mJ/cm 2 using a photo mask, the pattern was developed with a KOH alkaline aqueous solution and washed with distilled water. After removing distilled water, post-heat treatment (postbake) was performed at 240° C. for 20 minutes to obtain a color pattern.
[耐熱性評估] [Evaluation of heat resistance]
針對在如上所述的條件下製備的經後熱處理(後烘(Postbake)一次)的基板,利用分光光度計(MCPD,大塚股份有限公司(Otsuka Co.,Ltd))得到380nm至780nm波長範圍的吸收光譜。 For the post-heat-treated (postbake once) substrate prepared under the conditions described above, a spectrophotometer (MCPD, Otsuka Co., Ltd.) was used to obtain a wavelength range of 380 nm to 780 nm. absorption spectrum.
另外,追加性地在240℃下對經後熱處理(後烘(Postbake)一次)的基板處理60分鐘,在相同的設備與相同的測定範圍下得到透射率光譜。 In addition, the substrate subjected to the post-heat treatment (postbake once) was additionally treated at 240° C. for 60 minutes, and the transmittance spectrum was obtained in the same equipment and in the same measurement range.
使用利用將C光源作為背光得到的吸收光譜得到的值E(L*,a*,b*),藉由下述算式1計算「△Eab(耐熱性)」,並示於下述表2。 Using the value E(L*, a*, b*) obtained by the absorption spectrum obtained by using the C light source as a backlight, "ΔEab (heat resistance)" was calculated by the following formula 1, and shown in the following Table 2.
[算式1]△Eab(L*,a*,b*)={(△L*)2+(△a*)2+(△b*)2}1/2 [Formula 1]△Eab(L*, a*, b*)={(△L*) 2 +(△a*) 2 +(△b*) 2 } 1/2
△Eab(耐熱性)值小為顏色變化小的含義,表示耐熱性優異。 A small value of ΔEab (heat resistance) means that the color change is small, and indicates that the heat resistance is excellent.
[耐化學性評估] [Chemical Resistance Evaluation]
將進行一次後熱處理的基板剪為1cm×5cm後,利用分光光 度計(MCPD,大塚股份有限公司(Otsuka Co.,Ltd))得到380nm至780nm波長範圍的吸收光譜。 After cutting the substrate subjected to one post-heat treatment to 1 cm × 5 cm, use the spectroscopic light A spectrometer (MCPD, Otsuka Co., Ltd) obtained an absorption spectrum in the wavelength range of 380 nm to 780 nm.
得到光譜後,將其浸漬於16g的N-甲基-2-吡咯啶酮(N-methyl-2-pyrrolidone)溶劑,之後在常溫下放置10分鐘後,利用蒸餾水乾淨地清洗。在相同的設備與相同的測定範圍下得到透射率光譜。 After obtaining a spectrum, it was immersed in 16 g of N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone) solvent, left at room temperature for 10 minutes, and then washed cleanly with distilled water. Transmittance spectra were obtained with the same equipment and the same measurement range.
利用浸漬前後的光譜應用所述[算式1]進行計算,將「△Eab(耐化學性)」示於下述表2。△Eab(耐化學性)值小為顏色變化小的含義,表示耐化學性優異。 The above-mentioned [Equation 1] was used for calculation from the spectra before and after immersion, and "ΔEab (chemical resistance)" is shown in Table 2 below. A small value of ΔEab (chemical resistance) means that the color change is small, and indicates that the chemical resistance is excellent.
根據所述表2確認,與比較例1至比較例4相比,實施例1至實施例8的△Eab(耐熱性)及△Eab(耐化學性)值小, 藉由利用本說明書的一實施形態的化合物,可得到耐熱性及耐化學性優異的著色劑組成物與彩色濾光片。 From Table 2, it was confirmed that the ΔEab (heat resistance) and ΔEab (chemical resistance) values of Examples 1 to 8 were smaller than those of Comparative Examples 1 to 4, and By using the compound of one Embodiment of this specification, the coloring agent composition and the color filter which are excellent in heat resistance and chemical resistance can be obtained.
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