TWI738984B - Colored curable resin composition, color filter and display device - Google Patents

Colored curable resin composition, color filter and display device Download PDF

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TWI738984B
TWI738984B TW107108454A TW107108454A TWI738984B TW I738984 B TWI738984 B TW I738984B TW 107108454 A TW107108454 A TW 107108454A TW 107108454 A TW107108454 A TW 107108454A TW I738984 B TWI738984 B TW I738984B
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芦田徹
鈴木智也
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南韓商東友精細化工有限公司
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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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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
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    • 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
    • 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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Abstract

本發明提供可形成對比度優異的彩色濾光片的著色固化性樹脂組合物、彩色濾光片和顯示裝置。本發明的著色固化性樹脂組合物的特徵在於：包含著色劑、樹脂、聚合性化合物和聚合引發劑，其中，著色劑包含由式(I)表示的化合物，

Figure 107108454-A0202-11-0001-1
式(I)中，R1和R2各自獨立地表示可具有取代基的碳數1~8的烴基，X1和X2各自獨立地表示氫原子、氰基或胺甲醯基，L1和L2各自獨立地表示可具有取代基的碳數1~8的2價的烴基，k表示0以上且4以下的整數，Mn+表示任意的陽離子，以及n表示1以上且5以下的整數。 The present invention provides a coloring curable resin composition, a color filter, and a display device that can form a color filter with excellent contrast. The colored curable resin composition of the present invention is characterized by containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the colorant contains a compound represented by formula (I),
Figure 107108454-A0202-11-0001-1
 In the formula (I), R 1 and R 2 each independently represent a hydrocarbon group having 1 to 8 carbon atoms that may have a substituent, X 1 and X 2 each independently represent a hydrogen atom, a cyano group or a carbamoyl group, and L 1 And L 2 each independently represent an optionally substituted divalent hydrocarbon group having 1 to 8 carbon atoms, k represents an integer from 0 to 4, M n+ represents any cation, and n represents an integer from 1 to 5 .

Description

著色固化性樹脂組合物、彩色濾光片和顯示裝置 Colored curable resin composition, color filter and display device

本發明涉及著色固化性樹脂組合物、彩色濾光片和顯示裝置。 The present invention relates to a coloring curable resin composition, a color filter and a display device.

液晶顯示裝置、電致發光顯示裝置和電漿顯示器等顯示裝置、CCD和CMOS感測器等固態成像元件中所使用的彩色濾光片由著色固化性樹脂組合物製造。作為這樣的著色固化性樹脂組合物，已知包含由式(3)表示的化合物作為著色劑(專利文獻1)，

Figure 107108454-A0202-12-0001-3
The color filters used in display devices such as liquid crystal display devices, electroluminescence display devices and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors are manufactured from a coloring curable resin composition. As such a colored curable resin composition, it is known that a compound represented by formula (3) is contained as a colorant (Patent Document 1),
Figure 107108454-A0202-12-0001-3

先前技術文獻 Prior art literature 專利文獻 Patent literature

專利文獻1：日本特開2009-235392號公報 Patent Document 1: Japanese Patent Application Publication No. 2009-235392

由目前為止已知的上述著色固化性樹脂組合物形成的彩色濾光片有時不能充分地滿足對比度。因此，本發明提供可形成對比度優異 的彩色濾光片的著色固化性樹脂組合物。 The color filter formed from the aforementioned colored curable resin composition known so far may not sufficiently satisfy the contrast. Therefore, the present invention provides a colored curable resin composition that can form a color filter with excellent contrast.

本發明包含以下的發明。 The present invention includes the following inventions.

[1]一種著色固化性樹脂組合物，其包含著色劑、樹脂、聚合性化合物和聚合引發劑，著色劑包含由式(I)表示的化合物，

Figure 107108454-A0202-12-0002-4
式(I)中，R1和R2各自獨立地表示可具有取代基的碳數1~8的烴基，X1和X2各自獨立地表示氫原子、氰基或胺甲醯基，L1和L2各自獨立地表示可具有取代基的碳數1~8的2價的烴基，k表示0以上且4以下的整數，Mn+表示任意的陽離子，以及n表示1以上且5以下的整數。 [1] A colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant comprising a compound represented by formula (I),
Figure 107108454-A0202-12-0002-4
 In the formula (I), R 1 and R 2 each independently represent a hydrocarbon group having 1 to 8 carbon atoms that may have a substituent, X 1 and X 2 each independently represent a hydrogen atom, a cyano group or a carbamoyl group, and L 1 And L 2 each independently represent an optionally substituted divalent hydrocarbon group having 1 to 8 carbon atoms, k represents an integer from 0 to 4, M n+ represents any cation, and n represents an integer from 1 to 5 .

[2]一種彩色濾光片，其由[1]所述的著色固化性樹脂組合物形成。 [2] A color filter formed of the coloring curable resin composition described in [1].

[3]一種顯示裝置，其包含[2]所述的彩色濾光片。 [3] A display device including the color filter described in [2].

根據本發明，提供可形成對比度優異的彩色濾光片的著色固化性樹脂組合物。 According to the present invention, there is provided a coloring curable resin composition that can form a color filter excellent in contrast.

<著色固化性樹脂組合物> <Colored curable resin composition>

本發明的著色固化性樹脂組合物包含著色劑(A)、樹脂(B)、聚合性化合物(C)和聚合引發劑(D)，其中著色劑(A)包含由式(I)表示的化合物。 The colored curable resin composition of the present invention includes a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D), wherein the colorant (A) includes a compound represented by formula (I) .

本發明的著色固化性樹脂組合物可進一步包含聚合引發助劑(D1)、溶劑(E)、平整劑(F)。 The colored curable resin composition of the present invention may further include a polymerization initiation aid (D1), a solvent (E), and a leveling agent (F).

本說明書中，作為各成分例示的化合物只要無特別說明，則能夠單獨使用或者將多種組合使用。 In this specification, the compound exemplified as each component can be used alone or in combination of multiple types unless otherwise specified.

<著色劑(A)> <Colorant (A)>

本發明的著色固化性樹脂組合物包含由式(I)表示的化合物(以下有時稱為化合物(I))作為著色劑(A)。 The coloring curable resin composition of the present invention contains a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) as a colorant (A).

Figure 107108454-A0202-12-0003-5
式(I)中，R1和R2各自獨立地表示可具有取代基的碳數1~8的烴基，X1和X2各自獨立地表示氫原子、氰基或胺甲醯基，L1和L2各自獨立地表示可具有取代基的碳數1~8的2價的烴基，k表示0以上且4以下的整數，Mn+表示任意的陽離子，以及 n表示1以上且5以下的整數。
Figure 107108454-A0202-12-0003-5
 In the formula (I), R 1 and R 2 each independently represent a hydrocarbon group having 1 to 8 carbon atoms that may have a substituent, X 1 and X 2 each independently represent a hydrogen atom, a cyano group or a carbamoyl group, and L 1 And L 2 each independently represent an optionally substituted divalent hydrocarbon group having 1 to 8 carbon atoms, k represents an integer from 0 to 4, M n+ represents any cation, and n represents an integer from 1 to 5 .

由R1和R2表示的可具有取代基的碳數1~8的烴基較佳為可具有取代基的碳數1~8的脂肪族烴基或可具有取代基的碳數6~8的芳香族烴基，更佳為可具有取代基的碳數1~8的脂肪族烴基。 The hydrocarbon group having 1 to 8 carbon atoms which may have a substituent represented by R 1 and R 2 is preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 8 carbon atoms which may have a substituent. The group hydrocarbon group is more preferably an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent.

作為R1和R2中的碳數1~8的脂肪族烴基，可以是直鏈狀、分支鏈狀和環狀的任一種。 The aliphatic hydrocarbon group having 1 to 8 carbon atoms in R 1 and R 2 may be any of linear, branched, and cyclic.

作為直鏈狀或分支鏈狀的脂肪族烴基，可列舉出甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基等直鏈狀脂肪族烴基；異丙基、異丁基、異戊基、新戊基、2-乙基己基等分支鏈狀脂肪族烴基等。該脂肪族烴基的碳數較佳為1~6，更佳為1~5，又更佳為1~4。 Examples of linear or branched aliphatic hydrocarbon groups include linear aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl; isopropyl, Branched chain aliphatic hydrocarbon groups such as isobutyl, isopentyl, neopentyl, 2-ethylhexyl, etc. The carbon number of the aliphatic hydrocarbon group is preferably 1 to 6, more preferably 1 to 5, and still more preferably 1 to 4.

環狀的脂肪族烴基可以為單環也可以為多環。作為該環狀的脂肪族烴基，可列舉出環丙基、環丁基、環戊基、環己基等。該環狀的脂肪族烴基的碳數較佳為3~8，更佳為3~6。 The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The carbon number of the cyclic aliphatic hydrocarbon group is preferably 3-8, more preferably 3-6.

作為R1和R2中的碳數6~8的芳香族烴基，可列舉出苯基、甲苯基、二甲苯基、苯乙基、α-甲基苄基等。該芳香族烴基的碳數較佳為6。 Examples of the aromatic hydrocarbon group having 6 to 8 carbon atoms in R 1 and R 2 include a phenyl group, a tolyl group, a xylyl group, a phenethyl group, and an α-methylbenzyl group. The carbon number of the aromatic hydrocarbon group is preferably 6.

由R1和R2表示的碳數1~8的烴基可具有取代基，作為該取代基，可列舉出氟原子、氯原子、碘原子、溴原子等鹵素原子；硝基；氰基；胺基；羥基；甲氧基、乙氧基等碳數1~6的烷氧基；氫硫基；甲硫基、乙硫基等碳數1~6的烷硫基；羧基；胺甲醯基；甲氧基羰基、乙氧基羰基等碳數1~6的烷氧基羰基；磺酸基；胺磺醯基；甲氧基磺醯基、乙氧基磺醯基等碳數1~6的烷氧基磺醯基等。該碳數1~8的烴基更佳不具有取代基。 The hydrocarbon group having 1 to 8 carbon atoms represented by R 1 and R 2 may have a substituent. Examples of the substituent include halogen atoms such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom; a nitro group; a cyano group; an amine group. Group; Hydroxy; Alkoxy with 1 to 6 carbons such as methoxy and ethoxy; Hydrosulfide; Alkyl with 1 to 6 carbons such as methylthio and ethylthio; Carboxy; Aminomethanyl ;Methoxycarbonyl, ethoxycarbonyl and other alkoxycarbonyl groups with carbon numbers of 1~6; sulfonic acid group; sulfamoyl; methoxysulfonyl, ethoxysulfonyl, etc., carbon number of 1~6 The alkoxysulfonyl and so on. The hydrocarbon group having 1 to 8 carbon atoms preferably does not have a substituent.

R1和R2各自獨立地較佳為甲基、乙基、丙基、三氟甲基或 苯基，更佳為甲基或乙基。再者，R1和R2可以相同也可不同，較佳R1和R2相同。 R 1 and R 2 are each independently preferably a methyl group, an ethyl group, a propyl group, a trifluoromethyl group or a phenyl group, and more preferably a methyl group or an ethyl group. Furthermore, R 1 and R 2 may be the same or different. Preferably, R 1 and R 2 are the same.

X1和X2各自獨立地較佳為胺甲醯基或氰基，更佳為氰基。再者，X1和X2可以相同也可不同，較佳X1和X2相同。 X 1 and X 2 are each independently preferably a carbamoyl group or a cyano group, more preferably a cyano group. Furthermore, X 1 and X 2 may be the same or different, preferably X 1 and X 2 are the same.

由L1和L2表示的碳數1~8的2價的烴基為經由從碳數1~8的烴中將2個任意的氫原子去除而衍生的2價的基團，可列舉出碳數1~8的2價的脂肪族烴基或碳數6~8的2價的芳香族烴基。 The divalent hydrocarbon group with 1 to 8 carbons represented by L 1 and L 2 is a divalent group derived by removing two arbitrary hydrogen atoms from a hydrocarbon with 1 to 8 carbons, and carbon can be mentioned. A divalent aliphatic hydrocarbon group with 1 to 8 or a divalent aromatic hydrocarbon group with 6 to 8 carbons.

作為上述2價的脂肪族烴基，可列舉出碳數1~8的2價的鏈式烴基或碳數3~8的2價的脂環式烴基。 Examples of the above-mentioned divalent aliphatic hydrocarbon group include a divalent chain hydrocarbon group having 1 to 8 carbon atoms or a divalent alicyclic hydrocarbon group having 3 to 8 carbon atoms.

2價的鏈式脂肪族烴基可列舉出伸甲基、伸乙基、丙烷-1,2-二基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基、庚烷-1,7-二基、辛烷-1,8-二基等伸烷基等。 Examples of divalent chain aliphatic hydrocarbon groups include methylidene, ethylidene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, and pentane- 1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl and other alkylene groups.

作為2價的脂環式烴基，可列舉出環丙烷-1,1-二基、環丙烷-1,2-二基、環丁烷-1,1-二基、環丁烷-1,2-二基、環丁烷-1,3-二基、環戊烷-1,1-二基、環戊烷-1,2-二基、環戊烷-1,3-二基、環己烷-1,1-二基、環己烷-1,2-二基、環己烷-1,3-二基、環己烷-1,4-二基和由式(L-a1)~式(L-a6)表示的基團等。 Examples of the bivalent alicyclic hydrocarbon group include cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1,1-diyl, and cyclobutane-1,2 -Diyl, cyclobutane-1,3-diyl, cyclopentane-1,1-diyl, cyclopentane-1,2-diyl, cyclopentane-1,3-diyl, cyclohexane Alkyl-1,1-diyl, cyclohexane-1,2-diyl, cyclohexane-1,3-diyl, cyclohexane-1,4-diyl and by the formula (L-a1)~ The group represented by formula (L-a6) and the like.

Figure 107108454-A0202-12-0005-6
Figure 107108454-A0202-12-0005-6

作為2價的芳香族單環烴基，可列舉出鄰伸苯基、間伸苯 基、對伸苯基和由式(L-b1)~式(L-b6)表示的基團等。 Examples of the divalent aromatic monocyclic hydrocarbon group include ortho-phenylene, meta-phenylene, para-phenylene, and groups represented by formulas (L-b1) to (L-b6).

Figure 107108454-A0202-12-0006-7
Figure 107108454-A0202-12-0006-7

由L1和L2表示的碳數1~8的2價的烴基較佳為碳數1~8的2價的脂肪族烴基，更佳為碳數1~8的2價的鏈式烴基，又更佳為碳數1~8的伸烷基，特別佳為碳數1~8的直鏈狀伸烷基。 The divalent hydrocarbon group having 1 to 8 carbon atoms represented by L 1 and L 2 is preferably a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms, and more preferably a divalent chain hydrocarbon group having 1 to 8 carbon atoms, More preferably, it is a C1-C8 alkylene group, Especially preferably, it is a C1-C8 linear alkylene group.

另外，該2價的烴基的碳數較佳為1~6，更佳為1~4。 In addition, the carbon number of the divalent hydrocarbon group is preferably 1 to 6, and more preferably 1 to 4.

L1和L2中的碳數1~8的2價的烴基可具有取代基，作為該取代基，與由R1和R2表示的碳數1~8的烴基可具有的取代基相同。該2價的烴基更佳不具有取代基。 The divalent hydrocarbon group having 1 to 8 carbon atoms in L 1 and L 2 may have a substituent, and the substituent is the same as the substituent that may have the hydrocarbon group having 1 to 8 carbon atoms represented by R 1 and R 2. It is more preferable that this divalent hydrocarbon group does not have a substituent.

L1和L2各自獨立地較佳為伸甲基、伸乙基、丙烷-1,3-二基、丁烷-1,4-二基或由式(L-b1)~式(L-b6)表示的基團，更佳為伸甲基、伸乙基、丙烷-1,3-二基或丁烷-1,4-二基。再者，L1和L2可相同也可不同，但較佳它們相同。 L 1 and L 2 are each independently preferably a methylidene group, an ethylidene group, a propane-1,3-diyl group, a butane-1,4-diyl group or a formula (L-b1) ~ formula (L- The group represented by b6) is more preferably methylidene, ethylidene, propane-1,3-diyl or butane-1,4-diyl. Furthermore, L 1 and L 2 may be the same or different, but preferably they are the same.

k較佳為3以下，更佳為2以下，又更佳為1。再者，式(I)中，箭頭s和t表示的碳-碳雙鍵可以是E配置或Z配置的任一種。即，式(I)包含箭頭s和t表示的碳-碳雙鍵所形成的全部的幾何異構體，

Figure 107108454-A0202-12-0006-8
k is preferably 3 or less, more preferably 2 or less, and still more preferably 1. Furthermore, in formula (I), the carbon-carbon double bonds represented by arrows s and t may be either E configuration or Z configuration. That is, formula (I) includes all geometric isomers formed by the carbon-carbon double bonds represented by arrows s and t,
Figure 107108454-A0202-12-0006-8

Mn+較佳為氫離子、n價的金屬離子或者取代或未取代的銨離子。 M n+ is preferably a hydrogen ion, an n-valent metal ion, or a substituted or unsubstituted ammonium ion.

作為由Mn+表示的n價的金屬離子，可列舉出鋰離子、鈉離子、鉀離子等鹼金屬離子；鎂離子、鈣離子、鍶離子、鋇離子等鹼土金屬離子；鈦離子、鋯離子、鉻離子、錳離子、鐵離子、鈷離子、鎳離子、銅離子等過渡金屬離子；鋅離子、鎘離子、鋁離子、銦離子、錫離子、鉛離子、鉍離子等典型金屬離子等。 Examples of the n-valent metal ion represented by Mn + include alkali metal ions such as lithium ion, sodium ion, and potassium ion; alkaline earth metal ions such as magnesium ion, calcium ion, strontium ion, and barium ion; titanium ion, zirconium ion, etc. Transition metal ions such as chromium ion, manganese ion, iron ion, cobalt ion, nickel ion and copper ion; typical metal ions such as zinc ion, cadmium ion, aluminum ion, indium ion, tin ion, lead ion, bismuth ion, etc.

另外，作為由Mn+表示的取代或未取代的銨離子，可列舉出四烷基銨離子等四級銨離子。 In addition, examples of the substituted or unsubstituted ammonium ion represented by M n+ include quaternary ammonium ions such as tetraalkylammonium ions.

n較佳為4以下，更佳為3以下，又更佳為1或2。 n is preferably 4 or less, more preferably 3 or less, and still more preferably 1 or 2.

Mn+的個數為比式(I)中存在的-SO3 -的個數之和少1的數。因此，化合物(I)的價數為0，即，成為電中性的化合物。 The number of M n+ is one less than the sum of the number of -SO 3 - existing in the formula (I). Therefore, the valence of the compound (I) is 0, that is, it becomes an electrically neutral compound.

Mn+較佳為氫離子或n價的金屬離子，更佳為氫離子、鹼金屬離子或鹼土金屬離子，又更佳為氫離子、鈉離子、鉀離子、鎂離子或鋇離子，再更佳為氫離子或鋇離子。 M n+ is preferably hydrogen ion or n-valent metal ion, more preferably hydrogen ion, alkali metal ion or alkaline earth metal ion, still more preferably hydrogen ion, sodium ion, potassium ion, magnesium ion or barium ion, and still more preferably It is hydrogen ion or barium ion.

作為化合物(I)，可列舉出表1~5中所示的、由式(I-1)~式(I-420)表示的化合物等。化合物(I)較佳為由式(I-1)~式(I-168)表示的化合物，更佳為由式(I-29)~式(I-56)表示的化合物或由式(I-113)~式(I-140)表示的化合物，又更佳為由式(I-33)~式(I-36)表示的化合物或由式(I-117)~式(I-120)表示的化合物。 As the compound (I), the compounds represented by formula (I-1) to formula (I-420) shown in Tables 1 to 5, and the like can be cited. Compound (I) is preferably a compound represented by formula (I-1) to formula (I-168), more preferably a compound represented by formula (I-29) to formula (I-56) or a compound represented by formula (I -113)~The compound represented by formula (I-140), more preferably the compound represented by formula (I-33)~formula (I-36) or the compound represented by formula (I-117)~formula (I-120) Represents the compound.

Figure 107108454-A0202-12-0008-9
Figure 107108454-A0202-12-0008-9

Figure 107108454-A0202-12-0009-10
Figure 107108454-A0202-12-0009-10

Figure 107108454-A0202-12-0010-11
Figure 107108454-A0202-12-0010-11

Figure 107108454-A0202-12-0011-12
Figure 107108454-A0202-12-0011-12

Figure 107108454-A0202-12-0012-13
Figure 107108454-A0202-12-0012-13

再者，表1~5中，Me表示甲基，Et表示乙基。另外，L1和L2表示由式(L-1)~(L-7)表示的2價的烴基。式(L-1)~(L-7)中，＊n意指與氮原子的鍵合端，＊s意指與硫原子的鍵合端。 In addition, in Tables 1 to 5, Me represents a methyl group, and Et represents an ethyl group. In addition, L 1 and L 2 represent divalent hydrocarbon groups represented by formulas (L-1) to (L-7). In the formulas (L-1) to (L-7), *n means a bonding terminal to a nitrogen atom, and *s means a bonding terminal to a sulfur atom.

Figure 107108454-A0202-12-0013-14
Figure 107108454-A0202-12-0013-14

在Mn+為氫離子的情況下，由式(Ia)表示的化合物能夠藉由在酸性或鹼性條件下使由式(pt1)表示的化合物與由式(pt2)表示的化合物反應而製造。本反應中，相對於由式(pt2)表示的化合物1莫耳，由式(pt1)表示的化合物的使用量較佳為1.5~2.5莫耳。 When Mn + is a hydrogen ion, the compound represented by formula (Ia) can be produced by reacting the compound represented by formula (pt1) with the compound represented by formula (pt2) under acidic or basic conditions. In this reaction, the usage amount of the compound represented by the formula (pt1) is preferably 1.5 to 2.5 mol relative to 1 mol of the compound represented by the formula (pt2).

在Mn+為氫離子以外的陽離子的情況下，由式(Ib)表示的化合物能夠藉由使由式(Ia)表示的化合物與含有n價的金屬離子或者取代或未取代的銨離子的鹵化物(較佳氯化物)、醋酸鹽、磷酸鹽、硫酸鹽、矽酸鹽或氰化物等反應而製造。 In the case where M n+ is a cation other than hydrogen ion, the compound represented by formula (Ib) can be halogenated by halogenating the compound represented by formula (Ia) with a metal ion containing n valence or a substituted or unsubstituted ammonium ion. It is produced by the reaction of compounds (preferably chloride), acetate, phosphate, sulfate, silicate, or cyanide.

Figure 107108454-A0202-12-0014-15
Figure 107108454-A0202-12-0014-15

式(pt1)中，R3與R1或R2相同，X3與X1或X2相同，L3與L1或L2相同，式(pt2)中，Rc為氫原子、硝基或鹵素原子。k與上述相同，式(Ia)和式(Ib)中，R1、R2、X1、X2、L1、L2、k、Mn+和n與上述相同。 In formula (pt1), R 3 is the same as R 1 or R 2 , X 3 is the same as X 1 or X 2 , and L 3 is the same as L 1 or L 2. In formula (pt2), R c is a hydrogen atom, a nitro group Or halogen atoms. k is the same as above, and in formula (Ia) and formula (Ib), R 1 , R 2 , X 1 , X 2 , L 1 , L 2 , k, M n+ and n are the same as above.

相對於樹脂(B)100質量份，化合物(I)的含量較佳為0.1~150質量份，更佳為1~100質量份，又更佳為5~80質量份。 Relative to 100 parts by mass of the resin (B), the content of the compound (I) is preferably 0.1 to 150 parts by mass, more preferably 1 to 100 parts by mass, and still more preferably 5 to 80 parts by mass.

本發明的著色固化性樹脂組合物中之著色劑(A)，除了包含化合物(I)以外，可另包含染料(A1)和顏料(A2)。 The coloring agent (A) in the coloring curable resin composition of the present invention may contain a dye (A1) and a pigment (A2) in addition to the compound (I).

對染料(A1)並無特別限定，能夠使用公知的染料，例如可列舉出溶劑染料、酸性染料、直接染料、媒染染料等。作為染料，例如 色指數(由The Society of Dyers and Colourists出版)中在顏料以外分類為具有色相化合物的化合物、在色染公司之染色筆記中記載的公知的染料。另外，根據化學結構，可列舉出偶氮染料、菁染料、三苯基甲烷染料、呫噸染料、酞菁染料、蒽醌染料、萘醌染料、醌亞胺染料、次甲基染料、偶氮甲鹼染料、方酸染料、吖啶染料、苯乙烯基染料、香豆素染料、喹啉染料和硝基染料等。這些中，較佳為有機溶劑可溶性染料。 The dye (A1) is not particularly limited, and well-known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. As the dye, for example, the color index (published by The Society of Dyers and Colourists) is classified as a compound having a hue compound other than the pigment, and the known dye described in the dyeing notes of the color dyeing company. In addition, according to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinonimine dyes, methine dyes, azo Methine dyes, squaraine dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes and nitro dyes. Among these, organic solvent-soluble dyes are preferred.

作為顏料(A2)，並無特別限定，能夠使用公知的顏料，例如色指數(由The Society of Dyers and Colourists出版)中分類為顏料的顏料。 The pigment (A2) is not particularly limited, and well-known pigments such as pigments classified as pigments in the color index (published by The Society of Dyers and Colourists) can be used.

作為顏料，例如可列舉出C.I.顏料黃1、3、12、13、14、15、16、17、20、24、31、53、83、86、93、94、109、110、117、125、128、137、138、139、147、148、150、153、154、166、173、194、214等黃色顏料；C.I.顏料橙13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等橙色顏料；C.I.顏料紅9、97、105、122、123、144、149、166、168、176、177、180、192、209、215、216、224、242、254、255、264、265等紅色顏料；C.I.顏料藍15、15：3、15：4、15：6、60等藍色顏料；C.I.顏料紫1、19、23、29、32、36、38等紫色顏料；C.I.顏料綠7、36、58等綠色顏料；C.I.顏料棕23、25等棕色顏料；C.I.顏料黑1、7等黑色顏料等。 Examples of pigments include CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214 and other yellow pigments; CI pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, Orange pigments such as 59, 61, 64, 65, 71, 73; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 and other red pigments; CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments; CI Pigment Violet 1, 19, 23, 29, 32 , 36, 38 and other purple pigments; CI Pigment Green 7, 36, 58 and other green pigments; CI Pigment Brown 23, 25 and other brown pigments; CI Pigment Black 1, 7 and other black pigments.

相對於固體成分的總量，著色劑(A)的含量較佳為0.1~70質量%，更佳為0.5~60質量%，又更佳為1~50質量%。 The content of the colorant (A) is preferably 0.1 to 70% by mass, more preferably 0.5 to 60% by mass, and still more preferably 1 to 50% by mass relative to the total amount of solid components.

在著色劑(A)的總量中，化合物(I)的含量較佳為50質量%以上，更佳為80質量%以上，又更佳為90質量%以上。 In the total amount of the colorant (A), the content of the compound (I) is preferably 50% by mass or more, more preferably 80% by mass or more, and still more preferably 90% by mass or more.

在此，本說明書中的“固體成分的總量”是指從著色固化性樹脂組合物的總量中除去了溶劑的含量之後的量。固體成分的總量和相對於其的各成分的含量例如能夠採用液相色譜或氣相色譜等公知的分析手段測定。 Here, the "total amount of solid content" in this specification means the amount after excluding the solvent content from the total amount of the colored curable resin composition. The total amount of solid content and the content of each component relative to it can be measured by a known analysis means such as liquid chromatography or gas chromatography, for example.

<樹脂(B)> <Resin (B)>

對樹脂(B)並無特別限定，較佳為鹼可溶性樹脂，更佳具有來自從不飽和羧酸和不飽和羧酸酐中選擇的至少1種(a)(以下有時稱為“(a)”)的結構單元的樹脂。樹脂(B)又更佳具有選自以下結構單元中的至少一種的結構單元：來自具有碳數2~4的環狀醚結構和烯屬不飽和鍵的單體(b)(以下有時稱為“(b)”)的結構單元、來自可與(a)共聚的單體(c)(不過，與(a)和(b)不同)(以下有時稱為“(c)”)的結構單元以及在側鏈中具有烯屬不飽和鍵的結構單元。 The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably has at least one selected from unsaturated carboxylic acid and unsaturated carboxylic anhydride (a) (hereinafter sometimes referred to as "(a)) ") The resin of the structural unit. The resin (B) further preferably has at least one structural unit selected from the following structural units: derived from a monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as It is a structural unit of "(b)") derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)") The structural unit and the structural unit having an ethylenically unsaturated bond in the side chain.

作為(a)，具體地，例如可列舉出丙烯酸、甲基丙烯酸、馬來酸酐、衣康酸酐、3,4,5,6-四氫鄰苯二甲酸酐、琥珀酸單[2-(甲基)丙烯醯氧基乙基]酯等，較佳為丙烯酸、甲基丙烯酸、馬來酸酐。 Specific examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and succinic acid mono[2-(formaldehyde). (Yl)acryloyloxyethyl]ester, etc., preferably acrylic acid, methacrylic acid, and maleic anhydride.

(b)較佳具有碳數2~4的環狀醚結構(例如選自環氧乙烷環、氧雜環丁烷環和四氫呋喃環中的至少1種)和(甲基)丙烯醯氧基的單體。 (b) It preferably has a cyclic ether structure with a carbon number of 2 to 4 (for example, at least one selected from an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and a (meth)acryloyloxy group The monomer.

應予說明，本說明書中，“(甲基)丙烯酸”表示選自丙烯酸和甲基丙烯酸中的至少1種。“(甲基)丙烯醯基”和“(甲基)丙烯酸酯”等表述也具有同樣的含義。 In addition, in this specification, "(meth)acrylic acid" means at least one selected from acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

作為(b)，例如可列舉出(甲基)丙烯酸縮水甘油酯、乙 烯基苄基縮水甘油基醚、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯、3-乙基-3-(甲基)丙烯醯氧基甲基氧雜環丁烷、(甲基)丙烯酸四氫糠酯等，較佳為(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸3,4-環氧三環[5.2.1.02,6]癸酯、3-乙基-3-(甲基)丙烯醯氧基甲基氧雜環丁烷。 Examples of (b) include glycidyl (meth)acrylate, vinyl benzyl glycidyl ether, and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate , 3-ethyl-3-(meth)acryloyloxymethyloxetane, tetrahydrofurfuryl (meth)acrylate, etc., preferably glycidyl (meth)acrylate, (methyl) ) 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane.

作為(c)，例如可列舉出(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-甲基環己酯、(甲基)丙烯酸三環[5.2.1.02,6]癸烷-8-基酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-羥基乙酯、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、苯乙烯、乙烯基甲苯等，較佳為苯乙烯、乙烯基甲苯、(甲基)丙烯酸2-羥基乙酯、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺等。 As (c), for example, methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, (methyl) ) Tricyclo [5.2.1.0 2,6 ]decane-8-yl acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N -Cyclohexyl maleimide, N-benzyl maleimide, styrene, vinyl toluene, etc., preferably styrene, vinyl toluene, 2-hydroxyethyl (meth)acrylate, N- Phenyl maleimide, N-cyclohexyl maleimide, N-benzyl maleimide and the like.

具有在側鏈具有烯屬不飽和鍵的結構單元的樹脂能夠藉由使(b)加成於(a)與(c)的共聚物或者使(a)加成於(b)與(c)的共聚物而製造。該樹脂可以是使(a)加成於(b)與(c)的共聚物、進而使羧酸酐反應而成的樹脂。 Resins having structural units with ethylenically unsaturated bonds in the side chain can be added to the copolymer of (a) and (c) by (b) or (a) to (b) and (c) The copolymer is manufactured. The resin may be a resin obtained by adding (a) to the copolymer of (b) and (c), and further reacting carboxylic anhydride.

樹脂(B)的聚苯乙烯換算的重均分子量較佳為3000~100000，更佳為5000~50000，又更佳為5000~30000。 The weight average molecular weight in terms of polystyrene of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000.

樹脂(B)的分散度(重均分子量(Mw)/數均分子量(Mn))較佳為1.1~6，更佳為1.2~4。 The degree of dispersion (weight average molecular weight (Mw)/number average molecular weight (Mn)) of the resin (B) is preferably 1.1-6, more preferably 1.2-4.

樹脂(B)的酸值以固體成分換算計，較佳為20~170mg-KOH/g，更佳為30~150mg-KOH/g，又更佳為40~135mg-KOH/g。其中，酸值是作為為了中和樹脂(B)1g所需的氫氧化鉀的量(mg)測定 的值，例如能夠藉由使用氫氧化鉀水溶液進行滴定而求出。 The acid value of the resin (B) is converted to solid content, and is preferably 20 to 170 mg-KOH/g, more preferably 30 to 150 mg-KOH/g, and still more preferably 40 to 135 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and it can be determined, for example, by titration using an aqueous potassium hydroxide solution.

相對於固體成分的總量，樹脂(B)的含量較佳為7~65質量%，更佳為13~60質量%，又更佳為17~55質量%。 The content of the resin (B) relative to the total solid content is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass.

<聚合性化合物(C)> <Polymerizable compound (C)>

聚合性化合物(C)是可利用由聚合引發劑(D)產生的活性自由基和/或酸進行聚合的化合物，例如具有聚合性的烯屬不飽和鍵的化合物等，較佳為(甲基)丙烯酸酯化合物。 The polymerizable compound (C) is a compound that can be polymerized using living radicals and/or acid generated by the polymerization initiator (D), such as a compound having a polymerizable ethylenic unsaturated bond, etc., preferably (methyl) ) Acrylate compound.

其中，聚合性化合物(C)較佳為具有3個以上的烯屬不飽和鍵的聚合性化合物。作為這樣的聚合性化合物，例如可列舉出三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯等。 Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol penta(meth)acrylate. Esters, dipentaerythritol hexa(meth)acrylate, etc.

聚合性化合物(C)的重均分子量較佳為150以上且2900以下，更佳為250以上且1500以下。 The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2900 or less, more preferably 250 or more and 1500 or less.

包含聚合性化合物(C)的情況下，相對於固體成分的總量，聚合性化合物(C)的含量較佳為7~65質量%，更佳為13~60質量%，又更佳為17~55質量%。 When the polymerizable compound (C) is included, the content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 relative to the total solid content. ~55 mass%.

<聚合引發劑(D)> <Polymerization initiator (D)>

聚合引發劑(D)只要是利用光、熱的作用而產生活性自由基、酸等並能引發聚合的化合物，則並無特別限定，能夠使用公知的聚合引發劑。作為產生活性自由基的聚合引發劑，例如可列舉出N-苯甲醯氧基-1-(4-苯硫基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯硫基苯基)辛 烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯硫基苯基)-3-環戊基丙烷-1-酮-2-亞胺、2-甲基-2-嗎啉代-1-(4-甲硫基苯基)丙烷-1-酮、2-二甲基胺基-1-(4-嗎啉代苯基)-2-苄基丁烷-1-酮、1-羥基環己基苯基酮、2,4-雙(三氯甲基)-6-向日葵基-1,3,5-三嗪、2,4,6-三甲基苯甲醯基二苯基氧化膦、2,2’-雙(2-氯苯基)-4,4’,5,5’-四苯基聯咪唑等。 The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating living radicals, acids, etc. by the action of light and heat, and a known polymerization initiator can be used. Examples of polymerization initiators that generate living radicals include N-benzyloxy-1-(4-phenylthiophenyl)butan-1-one-2-imine and N-benzyloxy-1-(4-phenylthiophenyl)butan-1-one-2-imine Oxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzyloxy-1-(4-phenylthiophenyl)-3-cyclopentan Propane-1-one-2-imine, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1- (4-morpholinophenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,4-bis(trichloromethyl)-6-sunflower-1,3 ,5-Triazine, 2,4,6-trimethylbenzyl diphenyl phosphine oxide, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra Phenylbiimidazole and so on.

包含聚合引發劑(D)的情況下，相對於樹脂(B)和聚合性化合物(C)的合計量100質量份，聚合引發劑(D)的含量較佳為0.1~30質量份，更佳為1~20質量份。如果聚合引發劑(D)的含量在上述的範圍內，則存在高感度化而使曝光時間縮短的傾向，因此彩色濾光片的生產率提高。 When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C), and more preferably It is 1-20 parts by mass. If the content of the polymerization initiator (D) is within the above-mentioned range, the sensitivity tends to be increased and the exposure time is shortened, so the productivity of the color filter is improved.

本發明的著色固化性樹脂組合物可包含聚合引發助劑(D1)。 The coloring curable resin composition of the present invention may contain a polymerization initiation assistant (D1).

<聚合引發助劑(D1)> <Polymerization initiator (D1)>

聚合引發助劑(D1)是為了促進利用聚合引發劑引發了聚合的聚合性化合物的聚合而使用的化合物或增感劑。包含聚合引發助劑(D1)的情況下，聚合引發助劑(D1)通常與聚合引發劑(D)組合使用。 The polymerization initiation adjuvant (D1) is a compound or sensitizer used in order to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator. When the polymerization initiator (D1) is included, the polymerization initiator (D1) is usually used in combination with the polymerization initiator (D).

作為聚合引發助劑(D1)，可列舉出4,4’-雙(二甲基胺基)二苯甲酮(通稱米氏酮)、4,4’-雙(二乙基胺基)二苯甲酮、9,10-二甲氧基蒽、2,4-二乙基噻噸酮、N-苯基甘胺酸等。 As the polymerization initiator (D1), 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler’s ketone), 4,4'-bis(diethylamino) two Benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, N-phenylglycine, etc.

使用這些聚合引發助劑(D1)的情況下，相對於樹脂(B)和聚合性化合物(C)的合計量100質量份，其含量較佳為0.1~30質量份，更佳為1~20質量份。如果聚合引發助劑(D1)的量在該範圍內，能夠進一步以高感度形成著色圖案，並提高彩色濾光片的生產率。 In the case of using these polymerization initiation aids (D1), the content is preferably 0.1-30 parts by mass, more preferably 1-20 parts by mass relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C) Mass parts. If the amount of the polymerization initiation aid (D1) is within this range, it is possible to further form a colored pattern with high sensitivity and improve the productivity of the color filter.

本發明的著色固化性樹脂組合物可含有溶劑(E)。 The colored curable resin composition of the present invention may contain a solvent (E).

<溶劑(E)> <Solvent (E)>

對溶劑(E)並無特別限定，能夠使用該領域中通常所使用的溶劑。例如可列舉出酯溶劑(在分子內含有-COO-且不含-O-的溶劑)、醚溶劑(在分子內含有-O-且不含-COO-的溶劑)、醚酯溶劑(在分子內含有-COO-和-O-的溶劑)、酮溶劑(在分子內含有-CO-且不含-COO-的溶劑)、醇溶劑(在分子內含有OH且不含-O-、-CO-和-COO-的溶劑)、芳香族烴溶劑、醯胺溶劑、二甲基亞碸等。 The solvent (E) is not particularly limited, and solvents generally used in this field can be used. For example, ester solvents (solvents containing -COO- and no -O- in the molecule), ether solvents (solvents containing -O- and no -COO- in the molecule), ether ester solvents (solvents that contain -O- and no -COO- in the molecule) Solvents containing -COO- and -O-), ketone solvents (solvents containing -CO- and no -COO- in the molecule), alcohol solvents (containing OH and no -O-, -CO in the molecule) -And -COO- solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfide, etc.

作為溶劑，可列舉出：乳酸乙酯、乳酸丁酯、2-羥基異丁酸甲酯、醋酸正丁酯、丁酸乙酯、丁酸丁酯、丙酮酸乙酯、乙醯乙酸甲酯、環己醇乙酸酯和γ-丁內酯等酯溶劑(在分子內含有-COO-且不含-O-的溶劑)；乙二醇單丁基醚、二乙二醇單甲基醚、丙二醇單甲基醚、3-甲氧基-1-丁醇、二乙二醇二甲基醚、二乙二醇甲基乙基醚等醚溶劑(在分子內含有-O-且不含-COO-的溶劑)；3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸3-甲氧基丁酯、丙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、二乙二醇單乙基醚乙酸酯等醚酯溶劑(在分子內含有-COO-和-O-的溶劑)；4-羥基-4-甲基-2-戊酮、庚酮、4-甲基-2-戊酮、環己酮等酮溶劑(在分子內含有-CO-且不含-COO-的溶劑)；丁醇、環己醇、丙二醇等醇溶劑(在分子內含有OH且不含-O-、-CO-和-COO-的溶劑)； N,N-二甲基甲醯胺、N,N-二甲基乙醯胺和N-甲基吡咯烷酮等醯胺溶劑等。 Examples of solvents include ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetylacetate, Ester solvents such as cyclohexanol acetate and γ-butyrolactone (solvents containing -COO- and no -O- in the molecule); ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, Propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and other ether solvents (contains -O- in the molecule and does not contain- COO- solvent); methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl Ether acetate, diethylene glycol monoethyl ether acetate and other ether ester solvents (solvents containing -COO- and -O- in the molecule); 4-hydroxy-4-methyl-2-pentanone, Ketone solvents such as heptanone, 4-methyl-2-pentanone, and cyclohexanone (solvents containing -CO- and no -COO- in the molecule); alcohol solvents such as butanol, cyclohexanol, and propylene glycol (in the Solvents containing OH in the molecule and not containing -O-, -CO- and -COO-); N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, etc. Amide solvents, etc.

作為溶劑，更佳丙二醇單甲基醚乙酸酯、丙二醇單甲基醚、乳酸乙酯和3-乙氧基丙酸乙酯。 As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and ethyl 3-ethoxypropionate are more preferable.

包含溶劑(E)的情況下，相對於本發明的著色固化性樹脂組合物的總量，溶劑(E)的含量較佳為70~95質量%，更佳為75~92質量%。換言之，著色固化性樹脂組合物的固體成分的總量較佳為5~30質量%，更佳為8~25質量%。如果溶劑(E)的含量在上述的範圍內，塗佈時的平坦性變得良好，另外形成了彩色濾光片時色濃度沒有不足，因此顯示特性變得良好。 When the solvent (E) is included, the content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass relative to the total amount of the colored curable resin composition of the present invention. In other words, the total solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. If the content of the solvent (E) is within the above-mentioned range, the flatness at the time of application becomes good, and the color density is not insufficient when the color filter is formed, so the display characteristics become good.

本發明的著色固化性樹脂組合物可包含平整劑(F)。 The colored curable resin composition of the present invention may contain a leveling agent (F).

<平整劑(F)> <Leveling agent (F)>

作為平整劑(F)，可列舉出有機矽系表面活性劑、氟系表面活性劑和具有氟原子的有機矽系表面活性劑等。它們在側鏈可具有聚合性基團。 As the leveling agent (F), organosilicon surfactants, fluorine surfactants, organosilicon surfactants having fluorine atoms, and the like can be cited. They may have a polymerizable group in the side chain.

作為有機矽系表面活性劑，可列舉出在分子內具有矽氧烷鍵的表面活性劑等。具體地可列舉出TORAY SILICONE DC3PA、SH7PA、DC11PA、SH21PA、SH28PA、SH29PA、SH30PA、SH8400(商品名：東麗-道康寧(股)製造)、KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化學工業(股)製造)、TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF-4446、TSF4452和TSF4460(邁圖高新材料日本有限責任公司製造)等。 Examples of the organosilicon-based surfactant include surfactants having siloxane bonds in the molecule, and the like. Specific examples include TORAY SILICONE DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: Toray-Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 ( Shin-Etsu Chemical Industry Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (manufactured by Momentive Advanced Materials Japan Co., Ltd.), etc.

作為上述的氟系表面活性劑，可列舉出在分子內具有氟碳鏈的表面活性劑等。具體地，可列舉出FLUORAD(註冊商標)FC430、FC431(住友3M(股)製造)、MEGAFAC(註冊商標)F142D、F171、F172、F173、F177、F183、F554、R30、RS-718-K(DIC(股)製造)、EFTOP(註冊商標)EF301、EF303、EF351、EF352(三菱綜合材料電子化成(股)製造)、SURFLON(註冊商標)S381、S382、SC101、SC105(旭硝子(股)製造)和E5844((股)大金精細化學研究所製造)等。 Examples of the above-mentioned fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule, and the like. Specifically, FLUORAD (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K ( DIC (Stock) Manufacturing), EFTOP (registered trademark) EF301, EF303, EF351, EF352 (Mitsubishi Materials Electronics Corporation), SURFLON (registered trademark) S381, S382, SC101, SC105 (Asahi Glass Co., Ltd.) And E5844 (made by Daikin Fine Chemical Research Institute), etc.

作為上述的具有氟原子的有機矽系表面活性劑，可列舉出在分子內具有矽氧烷鍵和氟碳鏈的表面活性劑等。具體地，可列舉出MEGAFAC(註冊商標)R08、BL20、F475、F477和F443(DIC(股)製造)等。 Examples of the above-mentioned organosilicon surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, MEGAFAC (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Co., Ltd.) and the like can be cited.

包含平整劑(F)的情況下，相對於著色固化性樹脂組合物的總量，平整劑(F)的含量較佳為0.001~0.2質量%，更佳為0.002~0.1質量%。應予說明，該含量中不含顏料分散劑的含量。如果平整劑(F)的含量在上述的範圍內，則能夠使彩色濾光片的平坦性變得良好。 When the leveling agent (F) is included, the content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, and more preferably 0.002 to 0.1% by mass relative to the total amount of the colored curable resin composition. It should be noted that the content of the pigment dispersant is not included in this content. If the content of the leveling agent (F) is within the above-mentioned range, the flatness of the color filter can be improved.

<其他成分> <Other ingredients>

本發明的著色固化性樹脂組合物根據需要可包含填充劑、其他高分子化合物、密合促進劑、抗氧化劑、光穩定劑、鏈轉移劑等該技術領域中公知的添加劑。 The colored curable resin composition of the present invention may contain fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and other additives known in the technical field as necessary.

<著色固化性樹脂組合物的製造方法> <Production method of colored curable resin composition>

本發明的著色固化性樹脂組合物能夠通過將著色劑(A)、樹脂(B)、聚合性化合物(C)和聚合引發劑(D)以及根據需要使用的聚合引發助劑(D1)、溶劑(E)、平整劑(F)和其他成分混合而製備。 The colored curable resin composition of the present invention can be obtained by combining the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), and the polymerization initiation auxiliary (D1) and solvent as needed. (E), the leveling agent (F) and other ingredients are mixed to prepare.

<彩色濾光片的製造方法> <Method of Manufacturing Color Filter>

作為由本發明的著色固化性樹脂組合物製造著色圖案的方法，可列舉出光刻法、噴墨法、印刷法等。其中較佳光刻法。 As a method of producing a colored pattern from the colored curable resin composition of the present invention, a photolithography method, an inkjet method, a printing method, and the like can be cited. Among them, photolithography is preferred.

通過著色固化性樹脂組合物包含化合物(I)作為著色劑，從而能夠製作對比度特別優異的彩色濾光片。該彩色濾光片可用作顯示裝置(例如液晶顯示裝置、有機電致發光裝置、電子紙等)和固態成像元件中使用的彩色濾光片。 When the colored curable resin composition contains the compound (I) as a colorant, a color filter having particularly excellent contrast can be produced. The color filter can be used as a color filter used in display devices (for example, liquid crystal display devices, organic electroluminescence devices, electronic paper, etc.) and solid-state imaging elements.

實施例 Example

以下藉由實施例對本發明的著色固化性樹脂組合物更詳細地說明。例中的“%”和“份”只要無特別說明，則為質量%和質量份。 Hereinafter, the coloring curable resin composition of the present invention will be described in more detail with examples. Unless otherwise specified, "%" and "parts" in the examples are mass% and mass parts.

實施例1 Example 1

將由式(1-1)表示的化合物12.9份和由式(1-2)表示的化合物5.5份加入醋酸酐18份中，在室溫下混合。接下來加入三乙胺8份後，在40。℃下攪拌了5小時。反應結束後，加入醋酸乙酯100份，使結晶析出，過濾。用醋酸乙酯80份清洗3次，在60℃下將結晶減壓乾燥，得到了由式(I-33)表示的化合物13.3份。 12.9 parts of the compound represented by the formula (1-1) and 5.5 parts of the compound represented by the formula (1-2) are added to 18 parts of acetic anhydride and mixed at room temperature. Next, add 8 parts of triethylamine, at 40. Stirred for 5 hours at °C. After the completion of the reaction, 100 parts of ethyl acetate was added to precipitate crystals and filtered. It was washed three times with 80 parts of ethyl acetate, and the crystals were dried under reduced pressure at 60°C to obtain 13.3 parts of the compound represented by formula (I-33).

Figure 107108454-A0305-02-0026-1
Figure 107108454-A0305-02-0026-1

實施例2 Example 2

將由式(I-33)表示的化合物11份加入水100份中，製備溶解了由式(I-33)表示的化合物的液體(水溶液1)。另外，製備使氯化鋇二水合物19.5份溶解於水80份中的液體(水溶液2)，在40℃下歷時2小時將水溶液2滴入水溶液1中，然後攪拌4小時。冷卻後，過濾，用離子交換水100份清洗2次，將結晶在100℃下減壓乾燥，得到了由式(I-117)表示的化合物20份。 11 parts of the compound represented by formula (I-33) was added to 100 parts of water to prepare a liquid (aqueous solution 1) in which the compound represented by formula (I-33) was dissolved. Separately, a liquid (aqueous solution 2) in which 19.5 parts of barium chloride dihydrate was dissolved in 80 parts of water was prepared, and the aqueous solution 2 was dropped into the aqueous solution 1 at 40° C. for 2 hours, and then stirred for 4 hours. After cooling, it was filtered, washed twice with 100 parts of ion-exchanged water, and the crystals were dried under reduced pressure at 100°C to obtain 20 parts of a compound represented by formula (I-117).

Figure 107108454-A0305-02-0026-2
Figure 107108454-A0305-02-0026-2

[合成例1] [Synthesis Example 1]

在具有回流冷凝器、滴液漏斗和攪拌器的燒瓶內使適量的氮氣流入而使其成為氮氣氣氛，裝入丙二醇單甲基醚乙酸酯280份，邊攪拌邊加熱至80℃。接下來，在該燒瓶內，使用滴液泵歷時約5小時滴入了將丙烯酸38份、丙烯酸3,4-環氧三環[5.2.1.02,6]癸烷-8-基酯和丙烯酸3,4-環氧三環[5.2.1.02,6]癸烷-9-基酯的混合物(商品名“E-DCPA”、(股)大賽璐製造)289份溶解於丙二醇單甲基醚乙酸酯125份中的溶液。另一方面，使用另外的滴液泵歷時約6小時將聚合引發劑2,2-偶氮雙(2,4-二甲基戊腈)33份溶解於丙二醇單甲基醚乙酸酯235份中的溶液滴入燒瓶內。滴入結束後，在相同溫度下保持4小時後，冷卻到室溫，得到了固體成分35.1%的共聚物(樹脂(B-2))。得到的共聚物的重均分子量Mw為9200，分散度為2.08，固體成分換算的酸值為77mg-KOH/g。樹脂(B-2)具有下述結構單元。 In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was introduced to make it into a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was charged, and the mixture was heated to 80°C while stirring. Next, in the flask, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl acrylic acid and acrylic acid were dropped into the flask for about 5 hours using a dropping pump. 289 parts of 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-9-yl ester mixture (trade name "E-DCPA", manufactured by Daicel) dissolved in propylene glycol monomethyl ether A solution in 125 parts of acetate. On the other hand, 33 parts of polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) was dissolved in 235 parts of propylene glycol monomethyl ether acetate for about 6 hours using another drip pump. The solution in the flask dripped into the flask. After the dripping was completed, it was kept at the same temperature for 4 hours, and then cooled to room temperature to obtain a copolymer (resin (B-2)) with a solid content of 35.1%. The weight average molecular weight Mw of the obtained copolymer was 9,200, the degree of dispersion was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g. The resin (B-2) has the following structural unit.

Figure 107108454-A0305-02-0027-3
Figure 107108454-A0305-02-0027-3

樹脂的聚苯乙烯換算的重均分子量(Mw)和數均分子量(Mn)的測定採用凝膠滲透色譜(GPC法)在以下的條件下進行。 The measurement of the weight average molecular weight (Mw) and number average molecular weight (Mn) in terms of polystyrene of the resin was carried out using gel permeation chromatography (GPC method) under the following conditions.

裝置：HLC-8120GPC(東曹(股)製造) Device: HLC-8120GPC (manufactured by Tosoh Corporation)

柱：TSK-GELG2000HXL Column: TSK-GELG2000HXL

柱溫度：40℃ Column temperature: 40℃

溶劑：THF Solvent: THF

流速：1.0mL/min Flow rate: 1.0mL/min

被檢測液固體成分濃度：0.001~0.01質量% Concentration of solid content of the tested liquid: 0.001~0.01% by mass

注入量：50μL Injection volume: 50μL

檢測器：RI Detector: RI

校正用標準物質：TSK標準聚苯乙烯F-40、F-4、F-288、A-2500、A-500(東曹(股)製造) Standard materials for calibration: TSK standard polystyrene F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

將上述得到的聚苯乙烯換算的重均分子量和數均分子量之比(Mw/Mn)設為分散度。 The ratio (Mw/Mn) of the weight average molecular weight in terms of polystyrene obtained above and the number average molecular weight (Mw/Mn) was defined as the degree of dispersion.

實施例3~4 Examples 3~4

[分散液(P-1)的製作] [Preparation of dispersion (P-1)]

將由式(I-33)表示的化合物10份、分散劑BYK-LP N6919(BYK公司製造)的固體成分4份、樹脂(B-2)溶液(固體成分35.0%)5份(以固體成分計)、丙二醇單甲基醚乙酸酯181份稱量後，放入0.4μm的氧化鋯珠粒300份，使用塗料調理器(LAU公司製造)振盪6小時，經由過濾將氧化鋯珠粒除去，製作了分散液(P-1)。 10 parts of the compound represented by the formula (I-33), 4 parts of the solid content of the dispersant BYK-LP N6919 (manufactured by BYK), and 5 parts of the resin (B-2) solution (solid content 35.0%) (in terms of solid content) ), 181 parts of propylene glycol monomethyl ether acetate were weighed, and 300 parts of 0.4 μm zirconia beads were put in, and shaken for 6 hours using a paint conditioner (manufactured by LAU), and the zirconia beads were removed by filtration. A dispersion liquid (P-1) was prepared.

[分散液(P-2)的製作] [Preparation of dispersion (P-2)]

除了將由式(I-33)表示的化合物代替為由式(I-117)表示的化合物以外，與分散液(P-1)同樣地製作了分散液(P-2)。 Except for replacing the compound represented by formula (I-33) with the compound represented by formula (I-117), a dispersion liquid (P-2) was produced in the same manner as the dispersion liquid (P-1).

[著色固化性樹脂組合物的製備] [Preparation of colored curable resin composition]

以成為表6中所示的組成的方式將各成分混合，得到了著色固化性樹脂組合物。 Each component was mixed so that it might become a composition shown in Table 6, and the colored curable resin composition was obtained.

比較例1 Comparative example 1

用與實施例3相同方式製備著色固化性樹脂組合物，但分散液(P-1)以著色劑(A-1)替代。 A colored curable resin composition was prepared in the same manner as in Example 3, except that the dispersion liquid (P-1) was replaced with the colorant (A-1).

Figure 107108454-A0305-02-0029-4
Figure 107108454-A0305-02-0029-4

表6中各成分表示以下的化合物。 Each component in Table 6 shows the following compound.

著色劑(A-1)：由式(3)表示的化合物 Coloring agent (A-1): compound represented by formula (3)

Figure 107108454-A0305-02-0029-5
Figure 107108454-A0305-02-0029-5

樹脂(B-2)：樹脂(B-2)(固體成分換算) Resin (B-2): Resin (B-2) (in terms of solid content)

聚合性化合物(C-1)：二季戊四醇六丙烯酸酯(KAYARAD(註冊商標)DPHA；日本化藥(股)製造) Polymerizable compound (C-1): Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

聚合引發劑(D-1)：N-苯甲醯氧基-1-(4-苯硫基苯基)辛烷-1-酮-2-亞胺(IRGACURE(註冊商標)OXE 01；BASF公司製造) Polymerization initiator (D-1): N-benzyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; BASF Corporation manufacture)

溶劑(E-1)：丙二醇單甲基醚乙酸酯 Solvent (E-1): propylene glycol monomethyl ether acetate

<著色圖案的製作> <Creation of Colored Patterns>

在5cm2的玻璃基板(Eagle 2000；康寧公司製造)上採用旋塗法將著色固化性樹脂組合物塗佈後，在100℃下預烘乾3分鐘，得到了著色組合物層。放冷後，使形成了著色組合物層的基板與石英玻璃製之光罩的間隔成為100μm，使用曝光機(TME-150RSK；拓普康(股)製造)在大氣氣氛下、用150mJ/cm2的曝光量(365nm基準)進行了光照射。所述光罩係具有100μm線和間隙之圖案。將光照射後的著色組合物層在包含非離子系表面活性劑0.12%和氫氧化鉀0.04%的水系顯影液中在24℃下浸漬顯影60秒，水洗後，在烘箱中、200℃下進行烘乾20分鐘，得到了著色圖案。 After coating the colored curable resin composition on a 5 cm 2 glass substrate (Eagle 2000; manufactured by Corning Corporation) by a spin coating method, it was pre-baked at 100° C. for 3 minutes to obtain a colored composition layer. After cooling, the distance between the substrate on which the coloring composition layer was formed and the quartz glass mask was 100 μm, and the exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used in an atmospheric atmosphere at 150 mJ/cm. The exposure amount of 2 (365nm standard) was irradiated with light. The photomask has a pattern of 100μm lines and gaps. The light-irradiated coloring composition layer is immersed and developed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 24°C for 60 seconds. After washing with water, it is carried out in an oven at 200°C. After drying for 20 minutes, a colored pattern was obtained.

<對比度評價> <Contrast Evaluation>

對於實施例3、4和比較例1中得到的著色圖案，使用對比度計(CT-1：壺阪電機股份有限公司製造，色彩色差計BM-5A：拓普康股份有限公司製造，光源：F-10，偏光膜：壺阪電機股份有限公司製造)，將空白值設為30000，測定了對比度。將結果示於表7中。 For the coloring patterns obtained in Examples 3 and 4 and Comparative Example 1, a contrast meter (CT-1: manufactured by Kosaka Electric Co., Ltd., color difference meter BM-5A: manufactured by Topcon Co., Ltd., light source: F- 10. Polarizing film: manufactured by Kosaka Electric Co., Ltd.), the blank value was set to 30000, and the contrast was measured. The results are shown in Table 7.

Figure 107108454-A0305-02-0030-6
Figure 107108454-A0305-02-0030-6

產業上的可利用性 Industrial availability

採用本發明的著色固化性樹脂組合物，能夠製作對比度優異的彩色濾光片。 With the coloring curable resin composition of the present invention, a color filter with excellent contrast can be produced.

Figure 107108454-A0202-11-0002-2
Figure 107108454-A0202-11-0002-2

Claims (3)

一種著色固化性樹脂組合物，其包含著色劑、樹脂、聚合性化合物和聚合引發劑，所述著色劑包含由式(I)表示的化合物，
Figure 107108454-A0202-13-0001-22
 式(I)中，R 1和R 2各自獨立地表示可具有取代基的碳數1~8的烴基，X 1和X 2各自獨立地表示氫原子、氰基或胺甲醯基，L 1和L 2各自獨立地表示可具有取代基的碳數1~8的2價的烴基，k表示0以上且4以下的整數，M n+表示任意的陽離子，n表示1以上且5以下的整數。 A colored curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant comprising a compound represented by formula (I),
Figure 107108454-A0202-13-0001-22
 In the formula (I), R 1 and R 2 each independently represent a hydrocarbon group having 1 to 8 carbon atoms that may have a substituent, X 1 and X 2 each independently represent a hydrogen atom, a cyano group or a carbamoyl group, and L 1 And L 2 each independently represent an optionally substituted divalent hydrocarbon group having 1 to 8 carbon atoms, k represents an integer of 0 or more and 4 or less, M n+ represents an arbitrary cation, and n represents an integer of 1 or more and 5 or less. 一種彩色濾光片，其由根據請求項1所述的著色固化性樹脂組合物形成。 A color filter formed of the coloring curable resin composition according to claim 1. 一種顯示裝置，其包含根據請求項2所述的彩色濾光片。 A display device comprising the color filter according to claim 2.
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