TW201823372A - Compound, colored resin composition, color filter, display device, and solid-state imaging element having aromatic hydrocarbon group, aromatic heterocyclic group, metal substituent to produce high contrast material - Google Patents

Compound, colored resin composition, color filter, display device, and solid-state imaging element having aromatic hydrocarbon group, aromatic heterocyclic group, metal substituent to produce high contrast material Download PDF

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TW201823372A
TW201823372A TW106143956A TW106143956A TW201823372A TW 201823372 A TW201823372 A TW 201823372A TW 106143956 A TW106143956 A TW 106143956A TW 106143956 A TW106143956 A TW 106143956A TW 201823372 A TW201823372 A TW 201823372A
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aromatic hydrocarbon
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森脇章太
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南韓商東友精細化工有限公司
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
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    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • 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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Abstract

The present invention relates to a compound, a colored resin composition, a color filter, a display device, and a solid-state imaging element. The contrast of the color filter formed of the colored resin composition of the present invention can be sufficiently satisfied. The compound structure contains aromatic hydrocarbon group, aromatic heterocyclic group and metal substituents.

Description

化合物、著色樹脂組合物、濾色器、顯示裝置及固體攝像元件    Compound, colored resin composition, color filter, display device, and solid-state imaging element   

本發明係關於一種化合物、著色樹脂組合物、濾色器、顯示裝置及固體攝像元件。 The present invention relates to a compound, a colored resin composition, a color filter, a display device, and a solid-state imaging element.

在液晶顯示裝置、電致發光顯示裝置及電漿顯示器等顯示裝置、與CCD、CMOS感測器等固體攝像元件中所使用的濾色器係由著色樹脂組合物所製造。作為這樣的著色樹脂組合物，已知有包含部分溴化酞菁鋅顏料作為著色劑的組合物(專利文獻1)。 Color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays, and solid-state imaging elements such as CCDs and CMOS sensors are manufactured from a colored resin composition. As such a colored resin composition, a composition containing a partially brominated zinc phthalocyanine pigment as a colorant is known (Patent Document 1).

先前技術文獻 Prior art literature

專利文獻     Patent literature    

專利文獻1：日本專利特開第2004-70342號公報 Patent Document 1: Japanese Patent Laid-Open No. 2004-70342

由以往已知的上述著色樹脂組合物所形成的濾色器係有時不能充分地滿足對比度。 The color filter system formed from the conventionally-known colored resin composition may not sufficiently satisfy the contrast.

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

[1]著色樹脂組合物，其包含著色劑及樹脂，上述著色劑包含由式(Ia)表示的化合物。 [1] A colored resin composition including a colorant and a resin, wherein the colorant includes a compound represented by formula (Ia).

[式(Ia)中，R1至R4各自獨立地表示可具有取代基的碳數6至20的芳香族烴基或者可具有取代基的碳數3至19的芳香族雜環基。R5至R12各自獨立地表示氫原子、鹵素原子、氰基、硝基、可具有取代基的碳數1至20的飽和烴基、可具有取代基的碳數6至20的芳香族烴基或者可具有取代基的碳數3至19的芳香族雜環基。R5與R6、R7與R8、R9與R10以及R11與R12可各自相互結合而形成可具有取代基的芳香族烴環。M表示2價的金屬原子或者具有取代基的3價或4價的金屬原子。] [In the formula (Ia), R 1 to R 4 each independently represent an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 3 to 19 carbon atoms which may have a substituent. R 5 to R 12 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or An aromatic heterocyclic group having 3 to 19 carbon atoms which may have a substituent. R 5 and R 6 , R 7 and R 8 , R 9 and R 10, and R 11 and R 12 may be bonded to each other to form an aromatic hydrocarbon ring which may have a substituent. M represents a divalent metal atom or a trivalent or tetravalent metal atom having a substituent. ]

[2]上述[1]所述的著色樹脂組合物，其還包含聚合性化合物及聚合引發劑。 [2] The colored resin composition according to the above [1], further comprising a polymerizable compound and a polymerization initiator.

[3]由上述[1]或[2]所述的著色樹脂組合物形成的濾色器。 [3] A color filter formed from the colored resin composition described in [1] or [2] above.

[4]顯示裝置，其包含上述[3]所述的濾色器。 [4] A display device including the color filter described in [3] above.

[5]固體攝像元件，其包含上述[3]所述的濾色器。 [5] A solid-state imaging device including the color filter according to the above [3].

[6]由式(Ib')表示的化合物。 [6] A compound represented by the formula (Ib ').

[式(Ib')中，環A1至A4各自獨立地表示可具有取代基的芳香族烴環。不過，環A1至A4中至少一個為具有取代基的芳香族烴環。R1至R4各自獨立地表示可具有取代基的碳數6至20的芳香族烴基或者可具有取代基的碳數3至19的芳香族雜環基。M表示2價的金屬原子或者具有取代基的3價或4價的金屬原子。] [In the formula (Ib '), the rings A 1 to A 4 each independently represent an aromatic hydrocarbon ring which may have a substituent. However, at least one of the rings A 1 to A 4 is an aromatic hydrocarbon ring having a substituent. R 1 to R 4 each independently represent an aromatic hydrocarbon group having 6 to 20 carbons which may have a substituent or an aromatic heterocyclic group having 3 to 19 carbons which may have a substituent. M represents a divalent metal atom or a trivalent or tetravalent metal atom having a substituent. ]

採用本發明的著色樹脂組合物，能夠製造對比度高的濾色器。 According to the colored resin composition of the present invention, a color filter with high contrast can be manufactured.

本發明的著色樹脂組合物包含著色劑及樹脂。以下，有時將著色劑稱為「著色劑(A)」，有時將樹脂稱為「樹脂(B)」。 The colored resin composition of the present invention contains a colorant and a resin. Hereinafter, the colorant is sometimes referred to as "colorant (A)", and the resin is sometimes referred to as "resin (B)".

<著色劑(A)> <Colorant (A)>

上述著色劑(A)包含由式(Ia)表示的化合物。以下，有時將由式(Ia)表示的化合物稱為「化合物(Ia)」。 The colorant (A) includes a compound represented by the formula (Ia). Hereinafter, the compound represented by formula (Ia) may be referred to as "compound (Ia)".

[式(Ia)中，R1至R4各自獨立地表示可具有取代基的碳數6至20的芳香族烴基或者可具有取代基的碳數3至19的芳香族雜環基。R5至R12各自獨立地表示氫原子、鹵素原子、氰基、硝基、可具有取代基的碳數1至20的飽和烴基、可具有取代基的碳數6至20的芳香族烴基或者可具有取代基的碳數3至19的芳香族雜環基。R5與R6、R7與R8、R9與R10以及R11與R12可各自相互結合而形成可具有取代基的芳香族烴環。M表示2價的金屬原子或者具有取代基的3價或4價的金屬原子。] [In the formula (Ia), R 1 to R 4 each independently represent an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 3 to 19 carbon atoms which may have a substituent. R 5 to R 12 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or An aromatic heterocyclic group having 3 to 19 carbon atoms which may have a substituent. R 5 and R 6 , R 7 and R 8 , R 9 and R 10, and R 11 and R 12 may be bonded to each other to form an aromatic hydrocarbon ring which may have a substituent. M represents a divalent metal atom or a trivalent or tetravalent metal atom having a substituent. ]

由R1至R4及R5至R12表示的芳香族烴基的碳數較佳為6至15，更佳為6至12。作為該芳香族烴基，可列舉出苯基、鄰-甲苯基、間-甲苯基、對-甲苯基、二甲苯基、4-正-丁基苯基、4-三級-丁基苯基、萘基、蒽基、菲基、聯苯基、三聯苯基等，較佳為苯基、鄰-甲苯基、間-甲苯基、對-甲苯基、4-正-丁基苯基、4-三級- 丁基苯基，特別佳為4-正-丁基苯基、苯基。 The number of carbon atoms of the aromatic hydrocarbon group represented by R 1 to R 4 and R 5 to R 12 is preferably 6 to 15, more preferably 6 to 12. Examples of the aromatic hydrocarbon group include phenyl, o-tolyl, m-tolyl, p-tolyl, xylyl, 4-n-butylphenyl, 4-tertiary-butylphenyl, Naphthyl, anthryl, phenanthryl, biphenyl, terphenyl, etc., preferably phenyl, o-tolyl, m-tolyl, p-tolyl, 4-n-butylphenyl, 4- Tertiary-butylphenyl, 4-n-butylphenyl and phenyl are particularly preferred.

由R1至R4及R5至R12表示的上述芳香族烴基可具有一個或二個以上的取代基。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；氯甲基、三氟甲基等碳數1至6的鹵代烷基；甲氧基、乙氧基等碳數1至6的烷氧基；羥基；甲磺醯基等碳數1至6的烷烴磺醯基；甲氧基羰基、乙氧基羰基等碳數1至6的烷氧基羰基等。作為具有取代基的芳香族烴基，例如可列舉出2-氟苯基、2-氯苯基、2-溴苯基、2-碘苯基、3-氟苯基、3-氯苯基、3-溴苯基、3-碘苯基、4-氟苯基、4-氯苯基、4-溴苯基、4-碘苯基、2,3-二氯苯基、2,4-二氯苯基、2,5-二氯苯基、2,6-二氯苯基、3,5-二氯苯基、2,6-二氟苯基、1,3,5-三氯苯基、2,3,4,5-四氯苯基、4-氯甲基苯基、2-三氟甲基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-羥基苯基、3-羥基苯基、4-羥基苯基、4-胺磺醯基苯基、2-甲磺醯基苯基等，較佳為2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基。 The above-mentioned aromatic hydrocarbon group represented by R 1 to R 4 and R 5 to R 12 may have one or two or more substituents. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom; a halogenated alkyl group having 1 to 6 carbon atoms, such as a chloromethyl group and a trifluoromethyl group; Alkoxy groups of 1 to 6; hydroxyl groups; alkanesulfonyl groups of 1 to 6 carbons such as methanesulfonyl; alkoxycarbonyl groups of 1 to 6 carbons such as methoxycarbonyl and ethoxycarbonyl. Examples of the aromatic hydrocarbon group having a substituent include 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-iodophenyl, 3-fluorophenyl, 3-chlorophenyl, and 3 -Bromophenyl, 3-iodophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 2,3-dichlorophenyl, 2,4-dichloro Phenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 3,5-dichlorophenyl, 2,6-difluorophenyl, 1,3,5-trichlorophenyl, 2,3,4,5-tetrachlorophenyl, 4-chloromethylphenyl, 2-trifluoromethyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxybenzene Group, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 4-aminosulfonylphenyl, 2-methanesulfonylphenyl, etc., preferably 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl.

由R1至R4及R5至R12表示的芳香族雜環基的碳數較佳為3至12，更佳為3至8。作為該芳香族雜環基，可列舉出噻吩基、甲基噻吩基、呋喃基、吡咯基、咪唑基、吡唑基、噻唑基、異噻唑基、吡啶基、吲哚基、異吲哚基、吲唑基等。 The carbon number of the aromatic heterocyclic group represented by R 1 to R 4 and R 5 to R 12 is preferably 3 to 12, and more preferably 3 to 8. Examples of the aromatic heterocyclic group include thienyl, methylthienyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, indolyl, and isoindolyl. , Indazolyl, etc.

由R1至R4及R5至R12表示的上述芳香族雜環基可具有一個或二個以上的取代基。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；氯甲基、三氟甲基等碳數1至 6的鹵代烷基；甲氧基、乙氧基等碳數1至6的烷氧基；羥基；甲磺醯基等碳數1至6的烷烴磺醯基；甲氧基羰基、乙氧基羰基等碳數1至6的烷氧基羰基等。作為具有取代基的芳香族雜環基，可列舉出噻吩基、呋喃基、吡咯基、噻唑基、噁唑基等。 The above-mentioned aromatic heterocyclic group represented by R 1 to R 4 and R 5 to R 12 may have one or two or more substituents. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom; a halogenated alkyl group having 1 to 6 carbon atoms such as a chloromethyl group and a trifluoromethyl group; and a carbon group such as a methoxy group and an ethoxy group. Alkoxy groups of 1 to 6; hydroxyl groups; alkanesulfonyl groups of 1 to 6 carbons such as methanesulfonyl; alkoxycarbonyl groups of 1 to 6 carbons such as methoxycarbonyl and ethoxycarbonyl. Examples of the aromatic heterocyclic group having a substituent include thienyl, furyl, pyrrolyl, thiazolyl, and oxazolyl.

由R5至R12表示的飽和烴基可為直鏈狀、分支鏈狀及環狀的任一種。作為直鏈狀、分支鏈狀或環狀的飽和烴基，可列舉出甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十二烷基、正十六烷基、正二十烷基等直鏈狀烷基；異丙基、異丁基、異戊基、新戊基、2-乙基己基等分支鏈狀烷基等；環己基等環烷基等。該飽和烴基的碳數較佳為1至10，更佳為1至8，進一步更佳為1至6。 The saturated hydrocarbon group represented by R 5 to R 12 may be any of linear, branched, and cyclic. Examples of the linear, branched, or cyclic saturated hydrocarbon group include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and n-nonyl. , N-decyl, n-dodecyl, n-hexadecyl, n-icosyl, etc. linear alkyl groups; isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl And other branched chain alkyl groups, etc .; cyclohexyl groups, and so on. The carbon number of the saturated hydrocarbon group is preferably from 1 to 10, more preferably from 1 to 8, and even more preferably from 1 to 6.

由R5至R12表示的上述飽和烴基可具有一個或二個以上的取代基。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；甲氧基、乙氧基等碳數1至6的烷氧基；羥基；氰基；乙醯基等醯基；甲磺醯基等碳數1至6的烷烴磺醯基；甲氧基羰基、乙氧基羰基等碳數1至6的烷氧基羰基等。作為具有取代基的飽和烴基，可列舉出氯甲基、三氟甲基、羥基乙基、乙氧基乙基、氰基丙基、乙醯基丙基等。 The aforementioned saturated hydrocarbon group represented by R 5 to R 12 may have one or two or more substituents. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom; an alkoxy group having 1 to 6 carbon atoms such as a methoxy group and an ethoxy group; a hydroxyl group; a cyano group; Alkyl groups; alkanesulfonyl groups having 1 to 6 carbons such as methanesulfonyl; alkoxycarbonyl groups having 1 to 6 carbons such as methoxycarbonyl and ethoxycarbonyl. Examples of the saturated hydrocarbon group having a substituent include chloromethyl, trifluoromethyl, hydroxyethyl, ethoxyethyl, cyanopropyl, and ethenylpropyl.

作為由R5至R12表示的鹵素原子，可列舉出氟原子、氯原子、溴原子、碘原子等，較佳為溴原子。 Examples of the halogen atom represented by R 5 to R 12 include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like, and a bromine atom is preferred.

R5與R6、R7與R8、R9與R10或者R11與R12可各自相互結合而形成芳香族烴環。作為該芳香族烴環，可列舉出苯。在該 苯上進一步稠合或結合碳數6至20的芳香族烴環而成的結構也包含在該芳香族烴環中。作為在苯上稠合或結合芳香族烴環而成的結構，可列舉出萘、蒽、菲、聯苯、三聯苯等。另外，在芳香族烴環上結合了碳數1至20的飽和烴基的結構也包含在芳香族烴環中。作為芳香族烴環，較佳為苯。 R 5 and R 6 , R 7 and R 8 , R 9 and R 10, or R 11 and R 12 may be bonded to each other to form an aromatic hydrocarbon ring. Examples of the aromatic hydrocarbon ring include benzene. A structure in which an aromatic hydrocarbon ring having 6 to 20 carbon atoms is further fused or bonded to the benzene is also included in the aromatic hydrocarbon ring. Examples of the structure in which aromatic hydrocarbon rings are fused or bonded to benzene include naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, and the like. A structure in which a saturated hydrocarbon group having 1 to 20 carbon atoms is bonded to an aromatic hydrocarbon ring is also included in the aromatic hydrocarbon ring. The aromatic hydrocarbon ring is preferably benzene.

R5與R6、R7與R8、R9與R10或者R11與R12形成的芳香族烴環可具有一個或二個以上的取代基。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；氯甲基、三氟甲基等碳數1至6的鹵代烷基；甲氧基、乙氧基等碳數1至6的烷氧基；羥基；甲磺醯基等碳數1至6的烷烴磺醯基；乙醯基等碳數2至6的醯基；羥基羰基；甲氧基羰基、乙氧基羰基等碳數1至6的烷氧基羰基等。作為具有取代基的芳香族烴環，例如可列舉出一氟苯、二氟苯、三氟苯、四氟苯、一氯苯、二氯苯、三氯苯、四氯苯、一溴苯、二溴苯、三溴苯、四溴苯、甲氧基苯、乙氧基苯、羥基苯、甲磺醯基苯、乙醯基苯、羥基羰基苯、甲氧基羰基苯、乙氧基羰基苯等，較佳為乙醯基苯、羥基羰基苯、乙氧基羰基苯、一氟苯、一氯苯、一溴苯、二氟苯、二氯苯、二溴苯，特別佳為一氯苯。 The aromatic hydrocarbon ring formed by R 5 and R 6 , R 7 and R 8 , R 9 and R 10, or R 11 and R 12 may have one or two or more substituents. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom; a halogenated alkyl group having 1 to 6 carbon atoms such as a chloromethyl group and a trifluoromethyl group; and a carbon group such as a methoxy group and an ethoxy group. Alkoxy groups of 1 to 6; hydroxyl groups; alkanesulfonyl groups of 1 to 6 carbons such as methylsulfonyl; fluorenyl groups of 2 to 6 carbons such as ethylsulfanyl; hydroxycarbonyl; methoxycarbonyl, ethoxy 1 to 6 carbon alkoxycarbonyl groups and the like. Examples of the aromatic hydrocarbon ring having a substituent include monofluorobenzene, difluorobenzene, trifluorobenzene, tetrafluorobenzene, monochlorobenzene, dichlorobenzene, trichlorobenzene, tetrachlorobenzene, monobromobenzene, Dibromobenzene, tribromobenzene, tetrabromobenzene, methoxybenzene, ethoxybenzene, hydroxybenzene, methanesulfonylbenzene, ethynylbenzene, hydroxycarbonylbenzene, methoxycarbonylbenzene, ethoxycarbonyl Benzene, etc., preferably ethylammonylbenzene, hydroxycarbonylbenzene, ethoxycarbonylbenzene, monofluorobenzene, monochlorobenzene, monobromobenzene, difluorobenzene, dichlorobenzene, dibromobenzene, particularly preferably monochloro benzene.

作為由上述M表示的2價至4價的金屬原子，可列舉出根據IUPAC 1990年規則的長週期型週期表中分類為第2族至第15族的金屬原子。在這些中，作為金屬元素，較佳為Mg、Ti、Zr、V、Nb、Ta、Cr、Mo、W、Mn、Fe、Co、Ni、Ru、Rh、Pd、Os、 Ir、Pt、Cu、Ag、Au、Zn、Cd、Hg、Al、Ga、In、Si、Ge、Sn、Pb、Sb、Bi等，更佳為Ti、Zr、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Hg、Al、Ga、Si、Ge、Sn等，進一步更佳為Ni、Zn、Hg，最佳為Zn。 Examples of the divalent to tetravalent metal atoms represented by the above-mentioned M include metal atoms classified into groups 2 to 15 in the long-period periodic table according to the IUPAC 1990 rule. Among these, as the metal element, Mg, Ti, Zr, V, Nb, Ta, Cr, Mo, W, Mn, Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, Cu are preferable. , Ag, Au, Zn, Cd, Hg, Al, Ga, In, Si, Ge, Sn, Pb, Sb, Bi, etc., more preferably Ti, Zr, V, Cr, Mn, Fe, Co, Ni, Cu , Zn, Hg, Al, Ga, Si, Ge, Sn, etc., more preferably Ni, Zn, Hg, and most preferably Zn.

上述金屬原子中3價或4價的金屬原子具有取代基。較佳為具有取代基的3價或4價的金屬原子係藉由與二個氮原子形成二個N-M鍵，從而使用二個原子價，用剩餘的原子價與取代基結合。作為3價或4價的金屬原子具有的取代基，可列舉出氯原子等鹵素原子；側氧基；羥基；乙醯氧基等醯氧基；甲磺醯氧基等烷烴磺醯氧基等。 Among the above metal atoms, a trivalent or tetravalent metal atom has a substituent. It is preferable that a trivalent or tetravalent metal atom having a substituent has two N-M bonds with two nitrogen atoms, and thus the two atomic valences are used, and the remaining atomic valence is combined with the substituent. Examples of the substituent possessed by a trivalent or tetravalent metal atom include a halogen atom such as a chlorine atom; a pendant oxygen group; a hydroxyl group; an alkoxy group such as an ethoxy group; an alkane sulfonyl group such as a methanesulfonyloxy group; .

作為具有鹵素原子的3價或4價的金屬原子，可列舉出AlCl、SiCl2、VCl、VCl2、VOCl、FeCl、GaCl、ZrCl等。 Examples of the trivalent or tetravalent metal atom having a halogen atom include AlCl, SiCl 2 , VCl, VCl 2 , VOCl, FeCl, GaCl, ZrCl, and the like.

作為具有側氧基的3價或4價的金屬原子，可列舉出VO、GeO等。 Examples of the trivalent or tetravalent metal atom having a pendant oxygen group include VO and GeO.

作為具有羥基的3價或4價的金屬原子，可列舉出Si(OH)2、Cr(OH)2、Sn(OH)2等。 Examples of the trivalent or tetravalent metal atom having a hydroxyl group include Si (OH) 2 , Cr (OH) 2 , and Sn (OH) 2 .

化合物(Ia)較佳係R5至R12的至少一個為碳數6至20的芳香族烴基或碳數3至19的芳香族雜環基，或者R5與R6、R7與R8、R9與R10、或R11與R12相互結合而形成了芳香族烴環，進一步更佳為由式(Ib)表示的化合物。以下，有時將由式(Ib)表示的化合物稱為「化合物(Ib)」。 The compound (Ia) is preferably at least one of R 5 to R 12 is an aromatic hydrocarbon group having 6 to 20 carbon atoms or an aromatic heterocyclic group having 3 to 19 carbon atoms, or R 5 and R 6 , R 7 and R 8 , R 9 and R 10 , or R 11 and R 12 are bonded to each other to form an aromatic hydrocarbon ring, and a compound represented by the formula (Ib) is more preferable. Hereinafter, the compound represented by formula (Ib) may be referred to as "compound (Ib)".

[式(Ib)中，環A1至A4各自獨立地表示可具有取代基的芳香族烴環。R1至R4及M與上述相同。] [In the formula (Ib), the rings A 1 to A 4 each independently represent an aromatic hydrocarbon ring which may have a substituent. R 1 to R 4 and M are the same as described above. ]

再有，由A1至A4表示的芳香族烴環的至少一個可為具有取代基的芳香族烴環。在化合物(Ib)中，有時將由A1至A4表示的芳香族烴環的至少一個為具有取代基的芳香族烴環的化合物稱為「化合物(Ib')」。 In addition, at least one of the aromatic hydrocarbon rings represented by A 1 to A 4 may be an aromatic hydrocarbon ring having a substituent. In the compound (Ib), a compound in which at least one of the aromatic hydrocarbon rings represented by A 1 to A 4 is an aromatic hydrocarbon ring having a substituent may be referred to as a "compound (Ib ')".

作為由A1至A4表示的芳香族烴環，可列舉出苯。在該苯上進一步稠合或結合了碳數6至20的芳香族烴環的結構也包含於上述芳香族烴環中。作為在苯上稠合或結合了芳香族烴環的結構，可列舉出萘、蒽、菲、聯苯、三聯苯等。另外，在芳香族烴環上結合了碳數1至20的飽和烴基的結構也包含在芳香族烴環中。作為芳香族烴環，較佳為苯。 Examples of the aromatic hydrocarbon ring represented by A 1 to A 4 include benzene. A structure in which an aromatic hydrocarbon ring having 6 to 20 carbon atoms is further fused or bonded to the benzene is also included in the aromatic hydrocarbon ring. Examples of the structure in which aromatic hydrocarbon rings are fused or bonded to benzene include naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, and the like. A structure in which a saturated hydrocarbon group having 1 to 20 carbon atoms is bonded to an aromatic hydrocarbon ring is also included in the aromatic hydrocarbon ring. The aromatic hydrocarbon ring is preferably benzene.

由A1至A4表示的上述芳香族烴環可具有一個或二個以上的取代基。作為該取代基，可列舉出碳數1至20的飽和烴基；碳數6至20的芳香族烴基；氟原子、氯原子、碘原子、溴原子等鹵素原子；氯甲基、三氟甲基等碳數1至6的鹵代烷基；甲氧基、乙氧基等碳數1至6的烷氧基；羥基；甲磺醯基等碳數1至6的烷烴磺 醯基；乙醯基等碳數2至6的醯基；羥基羰基；甲氧基羰基、乙氧基羰基等碳數1至6的烷氧基羰基等。作為具有取代基的芳香族烴環，例如可列舉出一氟苯、二氟苯、三氟苯、四氟苯、一氯苯、二氯苯、三氯苯、四氯苯、一溴苯、二溴苯、三溴苯、四溴苯、甲氧基苯、乙氧基苯、羥基苯、甲磺醯基苯、乙醯基苯、羥基羰基苯、甲氧基羰基苯、乙氧基羰基苯等，較佳為乙醯基苯、羥基羰基苯、乙氧基羰基苯、一氟苯、一氯苯、一溴苯、二氟苯、二氯苯、二溴苯，特別佳為一氯苯。 The aromatic hydrocarbon ring represented by A 1 to A 4 may have one or two or more substituents. Examples of the substituent include a saturated hydrocarbon group having 1 to 20 carbon atoms; an aromatic hydrocarbon group having 6 to 20 carbon atoms; a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom; and a chloromethyl group and a trifluoromethyl group. Haloalkyl groups having 1 to 6 carbon atoms; alkoxy groups having 1 to 6 carbon atoms such as methoxy and ethoxy; hydroxyl groups; alkanesulfonyl groups having 1 to 6 carbon atoms such as methylsulfonyl; A fluorenyl group having 2 to 6 carbons; a hydroxycarbonyl group; an alkoxycarbonyl group having 1 to 6 carbons such as a methoxycarbonyl group and an ethoxycarbonyl group; Examples of the aromatic hydrocarbon ring having a substituent include monofluorobenzene, difluorobenzene, trifluorobenzene, tetrafluorobenzene, monochlorobenzene, dichlorobenzene, trichlorobenzene, tetrachlorobenzene, monobromobenzene, Dibromobenzene, tribromobenzene, tetrabromobenzene, methoxybenzene, ethoxybenzene, hydroxybenzene, methanesulfonylbenzene, ethynylbenzene, hydroxycarbonylbenzene, methoxycarbonylbenzene, ethoxycarbonyl Benzene, etc., preferably ethylammonylbenzene, hydroxycarbonylbenzene, ethoxycarbonylbenzene, monofluorobenzene, monochlorobenzene, monobromobenzene, difluorobenzene, dichlorobenzene, dibromobenzene, particularly preferably monochloro benzene.

作為化合物(Ib)，較佳為由式(Ic)表示的化合物。以下，有時將由式(Ic)表示的化合物稱為「化合物(Ic)」。 The compound (Ib) is preferably a compound represented by the formula (Ic). Hereinafter, the compound represented by formula (Ic) may be referred to as "compound (Ic)".

[式(Ic)中，R21至R36各自獨立地表示氫原子、可具有取代基的碳數1至20的飽和烴基、可具有取代基的碳數6至20的芳香族烴基、鹵素原子、碳數1至6的鹵代烷基、碳數1至6的烷氧基、羥基、碳數1至6的烷烴磺醯基、碳數2至6的醯基、羥基羰基或碳數1至6的烷氧基羰基。R1至R4及M與上述相同。] [In the formula (Ic), R 21 to R 36 each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and a halogen atom , Haloalkyl having 1 to 6 carbons, alkoxy having 1 to 6 carbons, hydroxyl, alkanesulfonyl having 1 to 6 carbons, fluorenyl having 2 to 6 carbons, hydroxycarbonyl or 1 to 6 carbons Alkoxycarbonyl. R 1 to R 4 and M are the same as described above. ]

再有，R21至R36中的至少一個可為可具有取代基的碳數1至20的飽和烴基、可具有取代基的碳數6至20的芳香族烴基、鹵素原子、碳數1至6的鹵代烷基、碳數1至6的烷氧基、羥基、碳數1至6的烷烴磺醯基、碳數2至6的醯基、羥基羰基或碳數1至6的烷氧基羰基。 In addition, at least one of R 21 to R 36 may be a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a halogen atom, or 1 to 20 carbon atoms. 6 haloalkyl, 1 to 6 carbon alkoxy, hydroxy, 1 to 6 carbon alkanesulfonyl, 2 to 6 carbon fluorenyl, hydroxycarbonyl, or 1 to 6 alkoxycarbonyl .

由R21至R36表示的可具有取代基的飽和烴基係與由R5至R12表示的可具有取代基的飽和烴基相同。 The saturated hydrocarbon group which may have a substituent represented by R 21 to R 36 is the same as the saturated hydrocarbon group which may have a substituent represented by R 5 to R 12 .

由R21至R36表示的可具有取代基的芳香族烴基係與由R1至R4及R5至R12表示的可具有取代基的芳香族烴基相同。 The aromatic hydrocarbon group which may have a substituent represented by R 21 to R 36 is the same as the aromatic hydrocarbon group which may have a substituent represented by R 1 to R 4 and R 5 to R 12 .

作為由R21至R36表示的鹵素原子，可列舉出氟原子、氯原子、碘原子、溴原子等，作為由R21至R36表示的鹵代烷基，可列舉出氯甲基、三氟甲基等，作為由R21至R36表示的烷氧基，可列舉出甲氧基、乙氧基等，作為由R21至R36表示的烷烴磺醯基，可列舉出甲磺醯基等，作為由R21至R36表示的烷氧基羰基，可列舉出甲氧基羰基、乙氧基羰基等。 Examples of the halogen atom represented by R 21 to R 36 include a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom. Examples of the halogenated alkyl group represented by R 21 to R 36 include chloromethyl and trifluoromethyl. Examples of the alkoxy group represented by R 21 to R 36 include a methoxy group and an ethoxy group, and examples of the alkanesulfonyl group represented by R 21 to R 36 include a mesylsulfonyl group. Examples of the alkoxycarbonyl group represented by R 21 to R 36 include a methoxycarbonyl group and an ethoxycarbonyl group.

作為化合物(Ic)，較佳係由R21至R36表示的基團中的一個至八個為氯原子或溴原子、剩餘為氫原子的化合物以及由R21至R36表示的基團都為氫原子的化合物。更佳地，可列舉出由式(I-1)至(I-23)表示的化合物，特別佳地，可列舉出由式(I-1)至(I-6)表示的化合物。 As the compound (Ic), compounds in which one to eight of the groups represented by R 21 to R 36 are a chlorine atom or a bromine atom, and the remainder are hydrogen atoms, and the groups represented by R 21 to R 36 are preferred. A compound that is a hydrogen atom. More preferred examples include compounds represented by formulae (I-1) to (I-23), and particularly preferred examples include compounds represented by formulas (I-1) to (I-6).

化合物(Ia)例如能夠藉由使由式(II)表示的化合物與由式(III)表示的化合物反應，接下來與甲醯胺反應而合成由式(IV)表示的化合物，使該由式(IV)表示的化合物與由式(V)表示的化合物反應而製造。 The compound (Ia) can synthesize a compound represented by the formula (IV) by reacting a compound represented by the formula (II) with a compound represented by the formula (III) and then reacting with formamidine, for example, The compound represented by (IV) is produced by reacting with a compound represented by formula (V).

[式中，R1至R12及M與上述相同。X表示鹵素原子。 Zn-表示n價的陰離子，a、b表示自然數。不過，a×n與b×2相等。] [In the formula, R 1 to R 12 and M are the same as described above. X represents a halogen atom. Z n- represents an n-valent anion, and a and b represent natural numbers. However, a × n is equal to b × 2. ]

就化合物(Ia)的含有率而言，在著色劑(A)的總量中，例如，為1至100質量%，較佳為50至100質量%，更佳為80至100質量%，最佳為90至100質量%。 The content of the compound (Ia) is, for example, 1 to 100% by mass, preferably 50 to 100% by mass, and more preferably 80 to 100% by mass in the total amount of the colorant (A). It is preferably 90 to 100% by mass.

著色劑(A)可包含染料或顏料作為化合物(Ia)以外的著色劑。作為染料，可列舉出溶劑染料、酸性染料、直接染料、媒染染料等，例如可列舉出在色指數(The Society of Dyers and Colourists出版)中在色料(pigment)以外分類為具有色調的物質的化合物、以及染色筆記(色染社)中記載的習知的染料。作為顏料，並無特別限定，能夠使用習知的顏料，例如可列舉出在色指數(The Society of Dyers and Colourists出版)中分類為色料的顏料。 The colorant (A) may contain a dye or a pigment as a coloring agent other than the compound (Ia). Examples of the dye include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of the dye include those classified as having a color tone other than pigments in the color index (published by The Society of Dyers and Colourists). Compounds and conventional dyes described in Dyeing Notes (Seishinsha). The pigment is not particularly limited, and conventional pigments can be used, and examples thereof include pigments classified as colorants by the color index (published by The Society of Dyers and Colourists).

例如可列舉出：C.I.色料黃1(以下省略C.I.色料黃的記載，只記載序號)、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.色料橙13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等橙色顏料；C.I.色料紅9、97、105、122、123、144、149、166、168、175、176、177、180、192、209、215、216、224、242、254、255、264、265等紅色顏料； C.I.色料藍15、15：3、15：4、15：6、60、80等青色顏料；C.I.色料紫1、19、23、29、32、36、38等紫色顏料；C.I.色料綠7、36、58等綠色顏料等。 For example: CI Pigment Yellow 1 (hereinafter, the description of CI Pigment Yellow is omitted, and only the serial number), 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 colorants orange 13, 31, Orange pigments such as 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168 , 175, 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, 80 and other cyan pigments; CI pigments purple 1, 19, 23, 29, 32, 36, 38 and other purple pigments; CI pigments green 7, 36, 58 and other green pigments.

作為可使用的染料，可列舉出：C.I.溶劑黃4、14、15、23、24、38、62、63、68、82、94、98、99、162；C.I.溶劑紅45、49、125、130；C.I.溶劑橙2、7、11、15、26、56；C.I.溶劑藍4、5、37、67、70、90；C.I.溶劑綠1、4、5、7、34、35等C.I.溶劑染料，C.I.酸性黃1、3、7、9、11、17、23、25、29、34、36、38、40、42、54、65、72、73、76、79、98、99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、155、157、160、161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、212、214、220、221、228、230、232、235、238、240、242、243、251；C.I.酸性紅1、4、8、14、17、18、26、27、29、31、34、35、37、42、44、50、57、66、73、88、91、97、103、111、114、129、133、134、138、143、145、150、151、158、176、182、183、195、198、206、211、215、216、217、227、228、249、252、257、258、260、261、266、268、270、274、277、280、281、308、312、315、316、339、341、345、346、349、382、383、394、401、412、417、 418、422、426；C.I.酸性橙6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、169、173；C.I.酸性紫6B、7、17、19；C.I.酸性藍1、7、9、15、18、22、29、42、59、60、62、70、72、74、82、83、86、87、90、92、93、100、102、103、104、113、117、120、126、130、131、142、147、151、154、158、161、166、167、168、170、171、184、187、192、199、210、229、234、236、242、243、256、259、267、285、296、315、335；C.I.酸性綠1、3、5、9、16、50、58、63、65、80、104、105、106、109等C.I.酸性染料，C.I.直接黃2、33、34、35、38、39、43、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、136、138、141；C.I.直接紅79、82、83、84、91、92、96、97、98、99、105、106、107、172、173、176、177、179、181、182、184、204、207、211、213、218、220、221、222、232、233、234、241、243、246、250；C.I.直接橙26、34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106、107；C.I.直接紫47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103、104； C.I.直接藍1、2、6、8、15、22、25、41、57、71、76、78、80、81、84、85、86、90、93、94、95、97、98、99、100、101、106、107、108、109、113、114、115、117、119、120、137、149、150、153、155、156、158、159、160、161、162、163、164、165、166、167、168、170、171、172、173、188、189、190、192、193、194、195、196、198、199、200、201、202、203、207、209、210、212、213、214、222、225、226、228、229、236、237、238、242、243、244、245、246、247、248、249、250、251、252、256、257、259、260、268、274、275、293；C.I.直接綠25、27、31、32、34、37、63、65、66、67、68、69、72、77、79、82等C.I.直接染料，C.I.分散黃54、76等C.I.分散染料，C.I.鹼性藍1、3、5、7、9、19、24、25、26、28、29、40、41、54、58、59、64、65、66、67、68；C.I.鹼性綠1等C.I.鹼性染料，C.I.反應性黃2、76、116；C.I.反應性橙16等C.I.反應性染料，C.I.媒染黃5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65；C.I.媒染紅1、2、4、9、12、14、17、18、19、22、23、24、25、26、30、32、33、36、37、38、39、41、43、45、46、48、53、56、63、71、74、85、86、88、90、94、95； C.I.媒染橙3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47、48；C.I.媒染紫1、2、4、5、7、14、22、24、30、31、32、37、40、41、44、45、47、48、53、58；C.I.媒染藍1、2、3、7、9、12、13、15、16、19、20、21、22、26、30、31、39、40、41、43、44、49、53、61、74、77、83、84；C.I.媒染綠1、3、4、5、10、15、26、29、33、34、35、41、43、53等C.I.媒染染料，C.I.還原綠1等C.I.還原染料等。 Examples of usable dyes include: CI Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 162; CI Solvent Red 45, 49, 125, 130; CI solvent orange 2, 7, 11, 15, 26, 56; CI solvent blue 4, 5, 37, 67, 70, 90; CI solvent green 1, 4, 5, 7, 34, 35 and other CI solvent dyes , CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI acidity Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 57, 66, 73, 88, 91, 97, 103, 111, 114 , 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173 ; CI Acid Violet 6B, 7, 17, 19; CI Acid Blue 1, 7, 9, 15, 18, 22, 29, 42, 59, 60, 62, 70, 72, 74, 82, 83, 86, 87 , 90, 92, 93, 100, 102, 103, 104, 113, 117, 120, 126, 130, 131, 142, 147, 151, 154, 158, 161, 166, 167, 168, 170, 171, 184 , 187, 192, 199, 210, 229, 234, 236, 242, 243, 256, 259, 267, 285, 296, 315, 335; CI Acid Green 1, 3, 5, 9, 16, 50, 58, 63, 65, 80, 104, 105, 106, 109 and other CI acid dyes, CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71 , 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26 , 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Purple 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 6, 8, 15, 22, 25, 41, 57, 71, 76 , 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120 , 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192 , 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242 , 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Green 25, 27, 31, 32, 34 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI direct dyes, CI disperse yellow 54, 76 and other CI disperse dyes, CI basic blue 1, 3, 5, 7, 9 , 19, 24, 25, 26, 28, 29, 40, 41, 54, 58, 59, 64, 65, 66, 67, 68; CI basic dyes such as CI basic green 1, CI reactive yellow 2, 76, 116; CI reactive dyes such as CI reactive orange 16, CI mordant yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Mordant Red 1, 2, 4, 9, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45 , 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95; CI mordant orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Purple 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37 , 40, 41, 44, 45, 47, 48, 53, 58; CI Mordant Blue 1, 2, 3, 7, 9, 12, 13, 15, 16, 19, 20, 21, 22, 26, 30, 31, 39, 40, 41, 43, 44, 49, 53, 61, 74, 77, 83, 84 C.I. Mordant Green 1,3,4,5,10,15,26,29,33,34,35,41,43,53 like C.I. mordant dyes, C.I. C.I. Vat Green 1 etc. vat dyes and the like.

就著色劑(A)的含量而言，相對於樹脂(B)100質量份，較佳為0.1至100質量份，更佳為1至50質量份，進一步更佳為5至30質量份。 The content of the colorant (A) is preferably 0.1 to 100 parts by mass, more preferably 1 to 50 parts by mass, and still more preferably 5 to 30 parts by mass based on 100 parts by mass of the resin (B).

<樹脂(B)> <Resin (B)>

對樹脂(B)並無特別限定，較佳為鹼可溶性樹脂，更佳為具有來自從不飽和羧酸及不飽和羧酸酐所組成之群組中選擇的至少一種(a)(以下有時稱為「(a)」)的結構單元的樹脂。樹脂(B)較佳還具有從來自具有碳數2至4的環狀醚結構及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)及(b)不同)(以下有時稱為「(c)」)的結構單元以及側鏈具有烯屬不飽和鍵的結構單元所組成之群組中選擇的至少一種結構單元。 The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably has at least one (a) selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic anhydride (hereinafter sometimes referred to as "(A)"). The resin (B) preferably further has a structural unit derived from a monomer (b) (hereinafter, sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, (A) copolymerizable monomer (c) (however, it is different from (a) and (b)) (hereinafter sometimes referred to as "(c)") and a unit having an ethylenically unsaturated side chain At least one structural unit selected from the group consisting of structural units.

作為(a)，具體地，例如可列舉出丙烯酸、甲基丙烯酸、馬來酸酐、伊康酸酐、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). Group) acrylic acid, etc., preferably acrylic acid, methacrylic acid, and maleic anhydride.

(b)較佳為具有碳數2至4的環狀醚結構(例如選自環氧乙烷環、氧呾環及四氫呋喃環所組成之群組中的至少一種)及(甲基)丙烯醯氧基的單體。 (b) A cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an ethylene oxide ring, an oxo ring, and a tetrahydrofuran ring) and (meth) acrylic acid Oxy monomer.

應予說明，本說明書中，「(甲基)丙烯酸」表示選自丙烯酸及甲基丙烯酸所組成之群組中的至少一種。「(甲基)丙烯醯基」及「(甲基)丙烯酸酯」等的表記也具有同樣的含義。 In addition, in this specification, "(meth) acrylic acid" means at least 1 sort (s) chosen from the group which consists of acrylic acid and methacrylic acid. The expressions "(meth) acrylfluorenyl" 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)丙烯醯氧基甲基氧呾、(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)丙烯醯氧基甲基氧呾。 Examples of (b) include glycidyl (meth) acrylate, vinyl benzyl glycidyl ether, and 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl ester (meth) acrylate 3, 3-ethyl-3- (meth) acryloxymethyloxyfluorene, tetrahydrofurfuryl (meth) acrylate, etc., preferably glycidyl (meth) acrylate, (meth) acrylic acid 3 , 4-epoxytricyclo [5.2.1.0 2,6 ] decyl ester, 3-ethyl-3- (meth) propenyloxymethyloxyfluorene.

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、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。 Examples of (c) include methyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, and (methyl) ) Tricyclo [5.2.1.0 2,6 ] decane-8-yl acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N -Cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene, etc., preferably styrene, vinyltoluene, N-phenylmaleimide, N-ring Hexyl 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。 A resin having a structural unit having an ethylenically unsaturated bond in a side chain can be added to (b) and (c) a copolymer by adding (b) to (b) and (c) ) Copolymer. The resin may be a resin obtained by adding (a) to the copolymer of (b) and (c), and further reacting a carboxylic anhydride.

樹脂(B)的聚苯乙烯換算的重量平均分子量較佳為3,000至100,000，更佳為5,000至50,000，進一步更佳為5,000至30,000。 The polystyrene equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000.

樹脂(B)的分散度[重量平均分子量(Mw)/數量平均分子量(Mn)]較佳為1.1至6，更佳為1.2至4。 The dispersion [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

樹脂(B)的酸值以固體成分換算計，較佳為50至170毫克-KOH/公克，更佳為60至150毫克-KOH/公克，進一步更佳為70至135毫克-KOH/公克。在此，酸值是作為將樹脂(B)1公克中和所需的氫氧化鉀的量(毫克)而被測定的值，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) in terms of solid content is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 gram of the resin (B), and can be obtained, for example, by titration with an aqueous potassium hydroxide solution.

就樹脂(B)的含有率而言，相對於固體成分的總量，較佳為7至65質量%，更佳為13至60質量%，進一步更佳為17至55質量%。 The content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass with respect to the total amount of the solid content.

在此，本說明書中的「固體成分的總量」是指從著色樹脂組合物的總量中去除了溶劑的含量後的量。固體成分的總量及相對於其的各成分的含量係例如能夠採用液相色譜或氣相色譜等習知的分析手段來測定。 Here, the "total amount of solid content" in the present specification means an amount obtained by removing the content of the solvent from the total amount of the colored resin composition. The total amount of the solid component and the content of each component relative to the solid component can be measured by a known analysis means such as liquid chromatography or gas chromatography.

本發明的著色樹脂組合物可包含聚合性化合物及/或聚合引發劑。以下，有時將包含聚合性化合物及聚合引發劑的著色樹脂組合物稱為「著色固化性樹脂組合物」。另外以下，有時將聚合性化合物稱為「聚合性化合物(C)」，有時將聚合引發劑稱為「聚合引發劑(D)」。 The colored resin composition of the present invention may contain a polymerizable compound and / or a polymerization initiator. Hereinafter, a colored resin composition containing a polymerizable compound and a polymerization initiator may be referred to as a "colored curable resin composition". In addition, hereinafter, a polymerizable compound may be referred to as a "polymerizable compound (C)", and a polymerization initiator may be referred to as a "polymerization initiator (D)".

<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)產生的活性自由基及/或酸進行聚合的化合物，例如可列舉出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 acids generated by the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and the like is preferable. (Meth) acrylate compounds.

其中，聚合性化合物(C)較佳為具有三個以上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、新戊四醇三(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯等。 Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane tri (meth) acrylate, neopentaerythritol tri (meth) acrylate, neopentaerythritol tetra (meth) acrylate, and dioxin Pentaerythritol penta (meth) acrylate, dinepentaerythritol hexa (meth) acrylate, and the like.

聚合性化合物(C)的重量平均分子量較佳為150以上且2,900以下，更佳為250以上且1,500以下。 The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

在包含聚合性化合物(C)的情況下，就聚合性化合物(C)的含有率而言，相對於固體成分的總量，較佳為7至65質量%，更佳為13至60質量%，進一步更佳為17至55質量%。 When the polymerizable compound (C) is contained, the content rate of the polymerizable compound (C) is preferably 7 to 65% by mass, and more preferably 13 to 60% by mass relative to the total amount of the solid content. It is still more preferably 17 to 55 mass%.

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

聚合引發劑(D)只要是在光、熱的作用下產生活性 自由基、酸等且可引發聚合的化合物，則並無特別限定，能夠使用習知的聚合引發劑。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-苯基氫硫基苯基)丁烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯基氫硫基苯基)辛烷-1-酮-2-亞胺、N-苯甲醯氧基-1-(4-苯基氫硫基苯基)-3-環戊基丙烷-1-酮-2-亞胺、2-甲基-2-嗎福啉基-1-(4-甲基氫硫基苯基)丙烷-1-酮、2-二甲基胺基-1-(4-嗎福啉基苯基)-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 such as active radicals and acids under the action of light and heat, and conventional polymerization initiators can be used. Examples of the polymerization initiator that generates living radicals include N-benzyloxy-1- (4-phenylhydrothiophenyl) butane-1-one-2-imine, and N-benzene Methyloxy-1- (4-phenylhydrothiophenyl) octane-1-one-2-imine, N-benzyloxy-1- (4-phenylhydrothiophenyl) ) -3-cyclopentylpropane-1-one-2-imine, 2-methyl-2-morpholinyl-1- (4-methylhydrothiophenyl) propane-1-one, 2 -Dimethylamino-1- (4-morpholinylphenyl) -2-benzylbutane-1-one, 1-hydroxycyclohexylphenyl ketone, 2,4-bis (trichloromethyl) ) -6-Sunfloweryl-1,3,5-triazine, 2,4,6-trimethylbenzylidene diphenylphosphine oxide, 2,2'-bis (2-chlorophenyl) -4 , 4 ', 5,5'-tetraphenylbiimidazole and the like.

在包含聚合引發劑(D)的情況下，就聚合引發劑(D)的含量而言，相對於樹脂(B)及聚合性化合物(C)的合計量100質量份，較佳為0.1至30質量份，更佳為1至20質量份。如果聚合引發劑(D)的含量在上述的範圍內，則具有高感度化、使曝光時間縮短的傾向，因此濾色器的生產率提高。 When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Part by mass, more preferably 1 to 20 parts by mass. When the content of the polymerization initiator (D) is within the above-mentioned range, the sensitivity tends to increase and the exposure time tends to be shortened, so the productivity of the color filter is improved.

本發明的著色樹脂組合物可包含聚合引發助劑。以下，有時將聚合引發助劑稱為「聚合引發助劑(D1)」。 The colored resin composition of the present invention may contain a polymerization initiation aid. Hereinafter, a polymerization initiation adjuvant may be called "polymerization initiation adjuvant (D1)".

<聚合引發助劑(D1)> <Polymerization Initiation Auxiliary (D1)>

聚合引發助劑(D1)為用於促進由聚合引發劑引發了聚合的聚合性化合物的聚合的化合物或者增感劑。在包含聚合引發助劑(D1)的情況下，通常與聚合引發劑(D)組合使用。 The polymerization initiation aid (D1) is a compound or a sensitizer for accelerating the polymerization of the polymerizable compound in which the polymerization is initiated by the polymerization initiator. When a polymerization initiator (D1) is included, it is usually used in combination with a 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(通稱米其勒酮)、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。 Examples of the polymerization initiation aid (D1) include 4,4'-bis (dimethylamino) benzophenone (commonly known as Michelin), 4,4'-bis (diethylamino) Benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, N-phenylglycine and the like.

在使用這些聚合引發助劑(D1)的情況下，相對於樹脂(B)及聚合性化合物(C)的合計量100質量份，其含量較佳為0.1至30質量份，更佳為1至20質量份。如果聚合引發助劑(D1)的量在該範圍內，則能夠進一步以高感度形成著色圖案，濾色器的生產率有提高的傾向。 When using these polymerization initiation aids (D1), the content is preferably from 0.1 to 30 parts by mass, more preferably from 1 to 100 parts by mass based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). 20 parts by mass. When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be further formed with high sensitivity, and the productivity of the color filter tends to be improved.

本發明的著色樹脂組合物較佳包含溶劑。以下，有時將溶劑稱為「溶劑(E)」。 The colored resin composition of the present invention preferably contains a solvent. Hereinafter, the solvent is sometimes referred to as "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使用的溶劑。例如可列舉出酯溶劑(分子內含-COO-且不含-O-的溶劑)、醚溶劑(分子內含-O-且不含-COO-的溶劑)、醚酯溶劑(分子內含-COO-及-O-的溶劑)、酮溶劑(分子內含-CO-且不含-COO-的溶劑)、醇溶劑(分子內含OH且不含-O-、-CO-及-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 commonly used in this field can be used. For example, ester solvents (solvents containing -COO- and -O- free), ether solvents (solvents containing -O- and -COO- free), and ether ester solvents (molecular- COO- and -O- solvents), ketone solvents (solvents containing -CO- and no -COO- in the molecule), alcohol solvents (molecules containing OH and no -O-, -CO- and -COO- Solvents), aromatic hydrocarbon solvents, amidine solvents, dimethyl sulfene and the like.

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、環己醇乙酸酯及γ-丁內酯等酯溶劑(分子內含-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(分子內含-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(分子內含-COO-及-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(分子內含-CO-且不含-COO-的溶劑)；丁醇、環己醇、丙二醇等醇溶劑(分子內含OH且不含-O-、-CO-及-COO-的溶劑)；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺及N-甲基吡咯烷酮等醯胺溶劑等。 Examples of the solvent include ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetate, and Ester solvents such as hexanol acetate and γ-butyrolactone (solvents containing -COO- and no -O- in the molecule); ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, and propylene glycol mono Ether solvents such as methyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether (containing -O- in the molecule and -COO- Solvent); methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate Ether solvents such as esters, diethylene glycol monoethyl ether acetate (solvents containing -COO- and -O- in the molecule); 4-hydroxy-4-methyl-2-pentanone, heptone, 4 -Methyl-2-pentanone, cyclohexanone and other ketone solvents (solvents containing -CO- and -COO- free in the molecule); alcohol solvents such as butanol, cyclohexanol, and propylene glycol (containing OH in the molecule and not Solvents containing -O-, -CO- and -COO-); N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone solvents Wait.

作為溶劑，更佳為丙二醇單甲基醚乙酸酯、丙二醇單甲基醚、乳酸乙酯、N-甲基吡咯烷酮及3-乙氧基丙酸乙酯。 As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, N-methylpyrrolidone, and ethyl 3-ethoxypropionate are more preferable.

在包含溶劑(E)的情況下，就溶劑(E)的含有率而言，相對於本發明的著色樹脂組合物的總量，較佳為70至95質量%，更佳為75至92質量%。換言之，著色樹脂組合物的固體成分的總量較佳為5至30質量%，更佳為8至25質量%。如果溶劑(E)的含量在上述的範圍內，則塗布時的平坦性變得良好，另外在形成了濾色器時色濃度沒有不足，因此具有顯示特性變得良好的傾向。 When the solvent (E) is contained, the content of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass relative to the total amount of the colored resin composition of the present invention. %. In other words, the total amount of solid content of the colored resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass. When the content of the solvent (E) is within the above-mentioned range, the flatness at the time of coating is good, and the color density is not insufficient when the color filter is formed, so that the display characteristics tend to be good.

<其他成分> <Other ingredients>

本發明的著色樹脂組合物根據需要可包含流平劑、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習知的添加劑。 The colored resin composition of the present invention may contain additives known in this technical field, such as leveling agents, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as necessary.

<著色樹脂組合物的製造方法> <Manufacturing method of colored resin composition>

本發明的著色樹脂組合物能夠藉由將著色劑(A)、 樹脂(B)、以及根據需要使用的聚合性化合物(C)、聚合引發劑(D)、溶劑(E)及其他成分混合而製備。 The colored resin composition of the present invention can be mixed by mixing a colorant (A), a resin (B), and a polymerizable compound (C), a polymerization initiator (D), a solvent (E), and other components used as necessary. preparation.

<濾色器的製造方法> <Manufacturing Method of Color Filter>

作為由本發明的著色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，較佳為光刻法。 Examples of a method for producing a colored pattern from the colored resin composition of the present invention include a photolithography method, an inkjet method, and a printing method. Among them, photolithography is preferred.

採用本發明的著色樹脂組合物，能夠製作對比度高的濾色器。該濾色器可用作在液晶顯示裝置、有機EL裝置、電子紙等顯示裝置及固體攝像元件中使用的濾色器。 By using the colored resin composition of the present invention, a color filter with high contrast can be produced. This color filter can be used as a color filter used in display devices such as liquid crystal display devices, organic EL devices, electronic paper, and solid-state imaging devices.

實施例 Examples

以下藉由實施例對本發明更詳細地說明，但本發明並不受這些實施例限定。例中，表示含量或使用量的%及份，只要無特別說明，則為質量基準。 Hereinafter, the present invention will be described in more detail through examples, but the present invention is not limited by these examples. In the examples,% and parts indicating the content or the amount of use are based on quality unless otherwise specified.

以下，化合物的結構係經由質量分析(LC：Agilent製1200型，MAS：Agilent製LC/MSD型)而確認。 Hereinafter, the structure of the compound was confirmed by mass analysis (LC: Agilent 1200 type, MAS: Agilent LC / MSD type).

(合成例1) (Synthesis example 1)

使鄰苯二甲腈(東京化成股份有限公司製造)5.0份溶解於脫水二***(關東化學股份有限公司製造)40份中，冷卻到-20℃，將苯基溴化鎂的1M四氫呋喃溶液(關東化學股份有限公司製造)42.6份滴入。滴入後，升溫到室溫，攪拌了3小時。將得到的反應液濃縮後，加入預先加入硫酸鎂經脫水的甲醯胺(東京化成股份有限公司製造)280份，在140℃下攪拌了3小時。反應結束後冷卻到室溫，將析出的固體過濾。將得到的過濾物用甲醇/ 水混合液700份洗淨後，在60℃下減壓乾燥一晚，得到了由式(IV-1)表示的化合物1.7份。收率為22%。 5.0 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in 40 parts of dehydrated diethyl ether (manufactured by Kanto Chemical Co., Ltd.), cooled to -20 ° C, and a 1M tetrahydrofuran solution of phenylmagnesium bromide ( (Made by Kanto Chemical Co., Ltd.) 42.6 parts. After the dropwise addition, the temperature was raised to room temperature and stirred for 3 hours. After the obtained reaction solution was concentrated, 280 parts of formamide (made by Tokyo Chemical Industry Co., Ltd.) dehydrated with magnesium sulfate was added in advance, and the mixture was stirred at 140 ° C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the precipitated solid was filtered. The obtained filtrate was washed with 700 parts of a methanol / water mixed solution, and then dried under reduced pressure at 60 ° C. overnight to obtain 1.7 parts of a compound represented by formula (IV-1). The yield was 22%.

鑒定：(質量分析)離子化模式=ESI+：m/z=[M+H]+398.5 Identification: (mass analysis) ionization mode = ESI +: m / z = [M + H] + 398.5

確切質量：397.2 Exact mass: 397.2

(合成例2) (Synthesis example 2)

接下來，加入由式(IV-1)表示的化合物0.5份、醋酸鋅(和光純藥工業股份有限公司製造)0.3份、二異丙基乙基胺(東京化成股份有限公司製造)0.325份、1-丁醇(和光純藥工業股份有限公司製造)10份，在110℃下進行了加熱回流6小時。反應結束後冷卻到室溫，將析出的固體過濾。將得到的固體用氯仿50份邊加熱邊洗淨後，在60℃下減壓乾燥一晚，得到了由式(I-1)表示的化合物0.4份。收率為76%。 Next, 0.5 part of a compound represented by formula (IV-1), 0.3 part of zinc acetate (manufactured by Wako Pure Chemical Industries, Ltd.), 0.325 part of diisopropylethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 10 parts of 1-butanol (manufactured by Wako Pure Chemical Industries, Ltd.) was heated and refluxed at 110 ° C for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the precipitated solid was filtered. The obtained solid was washed with 50 parts of chloroform while heating, and then dried under reduced pressure at 60 ° C. overnight to obtain 0.4 part of the compound represented by the formula (I-1). The yield was 76%.

鑒定：(質量分析)離子化模式=ESI+：m/z=[M+H]+857.0 Identification: (mass analysis) ionization mode = ESI +: m / z = [M + H] + 857.0

確切質量：856.23 Exact mass: 856.23

(合成例3) (Synthesis example 3)

使3-氯鄰苯二甲腈(和光純藥工業股份有限公司製造)2.0份溶解於脫水二***(關東化學股份有限公司製造)28份中，冷卻到-20℃，將苯基溴化鎂的1M四氫呋喃溶液(關東化學股份有限公司製造)13.2份滴入。滴入後，升溫到室溫，攪拌了3小時。將得到的反應液濃縮後，加入預先加入硫酸鎂經脫水的甲醯胺(東京化成股份有限公司製造)75份，在140℃下攪拌了30分鐘。反應結束後冷卻到室溫，將析出的固體過濾。將得到的過濾物用甲醇/水混合液375份洗淨後，在60℃下減壓乾燥一晚，得到了由式(IV-2)表示的化合物1.2份。收率為43%。 2.0 parts of 3-chlorophthalphthalonitrile (manufactured by Wako Pure Chemical Industries, Ltd.) was dissolved in 28 parts of dehydrated diethyl ether (manufactured by Kanto Chemical Co., Ltd.), cooled to -20 ° C, and phenylmagnesium bromide 13.2 parts of a 1M tetrahydrofuran solution (manufactured by Kanto Chemical Co., Ltd.) was dropped. After the dropwise addition, the temperature was raised to room temperature and stirred for 3 hours. After the obtained reaction solution was concentrated, 75 parts of formamide (manufactured by Tokyo Chemical Industry Co., Ltd.) in which magnesium sulfate was dehydrated was added in advance, and the mixture was stirred at 140 ° C for 30 minutes. After the reaction was completed, the mixture was cooled to room temperature, and the precipitated solid was filtered. The obtained filtrate was washed with 375 parts of a methanol / water mixed solution, and then dried under reduced pressure at 60 ° C. overnight to obtain 1.2 parts of a compound represented by formula (IV-2). The yield was 43%.

鑒定：(質量分析)離子化模式=ESI+：m/z=[M+H]+466.5 Identification: (mass analysis) ionization mode = ESI +: m / z = [M + H] + 466.5

確切質量：465.1 Exact mass: 465.1

(合成例4) (Synthesis example 4)

接下來，加入由式(IV-2)表示的化合物4.0份、醋酸鋅(和光純藥工業股份有限公司製造)1.8份、二異丙基乙基胺 (東京化成股份有限公司製造)2.0份、1-丁醇(和光純藥工業股份有限公司製造)120份，在110℃下進行了3小時加熱回流。反應結束後冷卻到室溫，將析出的固體過濾。將得到的固體用氯仿、四氫呋喃加熱洗淨後，在60℃下減壓乾燥一晚，得到了由式(I-4)表示的化合物2.2份。收率為55%。 Next, 4.0 parts of a compound represented by formula (IV-2), 1.8 parts of zinc acetate (manufactured by Wako Pure Chemical Industries, Ltd.), 2.0 parts of diisopropylethylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 120 parts of 1-butanol (manufactured by Wako Pure Chemical Industries, Ltd.) was heated and refluxed at 110 ° C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the precipitated solid was filtered. The obtained solid was heated and washed with chloroform and tetrahydrofuran, and then dried under reduced pressure at 60 ° C. overnight to obtain 2.2 parts of a compound represented by the formula (I-4). The yield was 55%.

鑒定：(質量分析)離子化模式=ESI+：m/z=[M+H]+994.8 Identification: (mass analysis) ionization mode = ESI +: m / z = [M + H] + 994.8

確切質量：992.07 Exact mass: 992.07

(合成例5) (Synthesis example 5)

在具有回流冷凝器、滴液漏斗及攪拌機的燒瓶內使適量的氮氣流入而置換為氮氣氣氛，裝入乙酸1-甲氧基-2-丙酯371份，邊攪拌邊加熱至85℃。接下來，在該燒瓶內歷時4小時滴入丙烯酸54份、丙烯酸3,4-環氧三環[5.2.1.02,6]癸烷-8-基酯及丙烯酸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」、大賽璐股份有限公司製造)225份、乙烯基甲苯(異構體混合物)81份、乙酸1-甲氧基-2-丙酯80份的混合溶液。另一方面，歷時5小時滴入將聚合引發劑2,2-偶氮二(2,4-二甲基戊腈)30份溶解於乙 酸1-甲氧基-2-丙酯160份而成的溶液。引發劑溶液的滴入結束後，在相同溫度下保持了4小時後，冷卻到室溫，用B型黏度計(23℃)測定的黏度為246毫帕(mPas)。樹脂(B-1)溶液的固體成分為37.5%，固體成分換算的酸值為115毫克-KOH/公克。生成的共聚物的重量平均分子量Mw為10600，分散度[Mw/Mn]為2.01。樹脂(B-1)具有以下的結構單元。 In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was allowed to flow in and replaced with a nitrogen atmosphere. 371 parts of 1-methoxy-2-propyl acetate was charged and heated to 85 ° C. while stirring. Next, 54 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decane-8-yl acrylate, and 3,4-epoxytricyclic acrylic acid were dripped into the flask over 4 hours. [5.2.1.0 2,6 ] mixture of decane-9-yl ester (trade name "E-DCPA", manufactured by Daicel Corporation) 225 parts, 81 parts of vinyl toluene (isomer mixture), acetic acid 1 -A mixed solution of 80 parts of methoxy-2-propyl ester. On the other hand, 30 parts of the polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) was dissolved in 160 parts of 1-methoxy-2-propyl acetate dropwise over 5 hours. The solution. After the addition of the initiator solution was completed, the solution was maintained at the same temperature for 4 hours, and then cooled to room temperature. The viscosity measured by a B-type viscometer (23 ° C) was 246 milliPascals (mPas). The solid content of the resin (B-1) solution was 37.5%, and the acid value in terms of solid content was 115 mg-KOH / g. The weight average molecular weight Mw of the produced copolymer was 10600, and the degree of dispersion [Mw / Mn] was 2.01. The resin (B-1) has the following structural units.

樹脂的聚苯乙烯換算的重量平均分子量(Mw)及數量平均分子量(Mn)的測定係使用GPC法、在以下的條件下進行。 The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured using the GPC method under the following conditions.

裝置：HLC-8120GPC(東曹股份有限公司製造) Device: HLC-8120GPC (manufactured by Tosoh Corporation)

柱：TSK-GELG2000HXL Column: TSK-GELG2000HXL

柱溫度：40℃ Column temperature: 40 ° C

溶劑：THF Solvent: THF

流速：1.0毫升/分鐘(mL/min) Flow rate: 1.0 ml / min (mL / min)

被檢測液固體成分濃度；0.001至0.01質量% Solid content concentration of test liquid; 0.001 to 0.01% by mass

注入量：50微升 Injection volume: 50 μl

檢測器：RI Detector: RI

校正用標準物質：TSK標準聚苯乙烯(TSK STANDARD POLYSTYRENE) Calibration Standards: TSK STANDARD POLYSTYRENE

F-40、F-4、F-288、A-2500、A-500(東曹股份有限公司製造) 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量平均分子量及數量平均分子量之比(Mw/Mn)作為分散度。 The ratio of the weight-average molecular weight and the number-average molecular weight (Mw / Mn) in terms of polystyrene obtained as described above was taken as the degree of dispersion.

[實施例1至2、比較例1] [Examples 1 to 2 and Comparative Example 1]

[著色樹脂組合物的製備] [Preparation of colored resin composition]

按表1中所示的份數將各成分混合，得到了著色樹脂組合物。 The components were mixed in the parts shown in Table 1 to obtain a colored resin composition.

註1： Note 1:

註2：將表中的右邊成分混合，使用珠磨機使顏料充分地分散而成的液體 Note 2: A liquid in which the right ingredients in the table are mixed and the pigment is sufficiently dispersed using a bead mill.

註3：固體成分換算量 Note 3: Amount of solid content conversion

註4：在顏料分散液以外使用的溶劑 Note 4: Solvents used in addition to pigment dispersions

註5：採用日本專利特開第2004-70342號公報的合成實施例1中記載的方法製造 Note 5: Manufactured by the method described in Synthesis Example 1 of Japanese Patent Laid-Open No. 2004-70342

[著色圖案的製作] [Creation of colored patterns]

在5公分見方的玻璃基板(EAGLE 2000；康寧公司製造)上採用旋塗法塗布著色樹脂組合物後，在100℃下預烘焙3分鐘，得到了著色組合物層。放冷後，使形成有著色組合物層的基板與石英玻璃製光遮罩的間隔為100微米，使用曝光機(TME-150RSK；拓普康(TOPCON)股份有限公司製造)，在大氣氣氛下，用150毫焦耳/平方公分(mJ/cm2)的曝光量(365奈米基準)進行光照射。作為光遮罩，使用了形成有100微米線及間隙圖案的光遮罩。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%及氫氧化鉀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、150℃下進行20分鐘後烘焙，得到了著色圖案。 A colored resin composition was applied on a 5 cm square glass substrate (EAGLE 2000; manufactured by Corning) by a spin coating method, and then prebaked at 100 ° C for 3 minutes to obtain a colored composition layer. After leaving to cool, the distance between the substrate on which the colored composition layer was formed and the light mask made of quartz glass was 100 μm, and an exposure machine (TME-150RSK; manufactured by TOPCON Co., Ltd.) was used in an atmospheric atmosphere. The light was irradiated with an exposure amount (based on 365 nanometers) of 150 millijoules / cm 2 (mJ / cm 2 ). As the light mask, a light mask in which a 100 micron line and a gap pattern were formed was used. The coloring composition layer after light irradiation was immersed and developed at 24 ° C for 60 seconds in an aqueous developing solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide. After washing with water, it was performed in an oven at 150 ° C. After 20 minutes of baking, a colored pattern was obtained.

用光學顯微鏡觀察由實施例1及2的著色樹脂組合物得到的著色圖案，結果確認分辨出100微米線及間隙。 The coloring patterns obtained from the coloring resin compositions of Examples 1 and 2 were observed with an optical microscope. As a result, it was confirmed that 100 micron lines and gaps were resolved.

[膜厚測定] [Measurement of film thickness]

使用膜厚測定裝置(DEKTAK(註冊商標)3；日本真空技術股份有限公司製造)測定了得到的著色圖案的膜厚。將 結果示於表2中。 The film thickness of the obtained colored pattern was measured using a film thickness measuring device (DEKTAK (registered trademark) 3; manufactured by Japan Vacuum Technology Co., Ltd.). The results are shown in Table 2.

[著色塗膜的製作] [Production of colored coating film]

在5公分見方的玻璃基板(EAGLE 2000；康寧公司製造)上，採用旋塗法塗布著色樹脂組合物使得後烘焙後的膜厚成為與上述著色圖案相同的膜厚後，在100℃下預烘焙3分鐘。放冷後，使用曝光機(TME-150RSK；拓普康股份有限公司製造)，在大氣氣氛下、用150毫焦耳/平方公分的曝光量(365奈米基準)進行光照射。光照射後，在烘箱中、150℃下進行20分鐘後烘焙，得到了著色塗膜。 On a 5 cm square glass substrate (EAGLE 2000; manufactured by Corning), a colored resin composition was applied by spin coating so that the post-baking film thickness was the same as the above-mentioned colored pattern, and then pre-baked at 100 ° C. 3 minutes. After being allowed to cool, light exposure was performed using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) with an exposure amount (based on 365 nanometers) of 150 mJ / cm2 in the atmosphere. After light irradiation, it was baked in an oven at 150 ° C. for 20 minutes to obtain a colored coating film.

[對比度評價] [Contrast evaluation]

對於得到的著色塗膜，使用對比度計(CT-1；壺坂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；壺坂電機股份有限公司製造)測定對比度。應予說明，測定時的空白值為30000。將結果示於表2中。 For the obtained colored coating film, a contrast meter (CT-1; manufactured by Husaka Electric Co., Ltd., color difference meter BM-5A; manufactured by Topcon Corporation, light source; F-10, polarizing film; Husaka Electric Co., Ltd.) to measure the contrast. The blank value at the time of measurement was 30,000. The results are shown in Table 2.

以上確認了採用實施例的著色樹脂組合物得到的著 色塗膜的對比度高。由此可知，由本發明的著色樹脂組合物得到的著色塗膜、著色圖案作為濾色器是有用的，包含該濾色器的顯示裝置的顯示特性優異，包含該濾色器的固體攝像元件的攝像特性優異。 The above confirmed that the contrast of the colored coating film obtained by using the colored resin composition of the example was high. From this, it can be seen that the colored coating film and colored pattern obtained from the colored resin composition of the present invention are useful as color filters. The display device including the color filter is excellent in display characteristics. Excellent imaging characteristics.

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，能夠形成對比度高的濾色器。 According to the colored curable resin composition of the present invention, a color filter with high contrast can be formed.

Claims (6)

一種著色樹脂組合物，其包含著色劑及樹脂，該著色劑包含由式(Ia)表示的化合物， 式(Ia)中，R 1至R 4各自獨立地表示可具有取代基的碳數6至20的芳香族烴基或者可具有取代基的碳數3至19的芳香族雜環基；R 5至R 12各自獨立地表示氫原子、鹵素原子、氰基、硝基、可具有取代基的碳數1至20的飽和烴基、可具有取代基的碳數6至20的芳香族烴基或者可具有取代基的碳數3至19的芳香族雜環基，R 5與R 6、R 7與R 8、R 9與R 10以及R 11與R 12可各自相互結合而形成可具有取代基的芳香族烴環；以及M表示2價的金屬原子或者具有取代基的3價或4價的金屬原子。 A colored resin composition comprising a colorant and a resin, the colorant comprising a compound represented by formula (Ia), In Formula (Ia), R 1 to R 4 each independently represent an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 3 to 19 carbon atoms which may have a substituent; R 5 to R 12 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, or may have a substituent An aromatic heterocyclic group having 3 to 19 carbon atoms, R 5 and R 6 , R 7 and R 8 , R 9 and R 10, and R 11 and R 12 may be combined with each other to form an aromatic group which may have a substituent. A hydrocarbon ring; and M represents a divalent metal atom or a trivalent or tetravalent metal atom having a substituent. 如請求項1所述的著色樹脂組合物，其更包含聚合性化合物及聚合引發劑。     The colored resin composition according to claim 1, further comprising a polymerizable compound and a polymerization initiator.     一種由如請求項1或2所述的著色樹脂組合物形成的濾色器。     A color filter formed from the colored resin composition according to claim 1 or 2.     一種顯示裝置，其包含如請求項3所述的濾色器。     A display device including the color filter according to claim 3.     一種固體攝像元件，其包含如請求項3所述的濾色器。     A solid-state imaging element including the color filter according to claim 3.     一種由式(Ib')表示的化合物： 式(Ib')中，環A 1至A 4各自獨立地表示可具有取代基的芳香族烴環，不過，環A 1至A 4中至少一個為具有取代基的芳香族烴環；R 1至R 4各自獨立地表示可具有取代基的碳數6至20的芳香族烴基或者可具有取代基的碳數3至19的芳香族雜環基；以及M表示2價的金屬原子或者具有取代基的3價或4價的金屬原子。 A compound represented by the formula (Ib '): In the formula (Ib '), the rings A 1 to A 4 each independently represent an aromatic hydrocarbon ring which may have a substituent. However, at least one of the rings A 1 to A 4 is an aromatic hydrocarbon ring having a substituent; R 1 To R 4 each independently represent an aromatic hydrocarbon group having 6 to 20 carbons which may have a substituent or an aromatic heterocyclic group having 3 to 19 carbons which may have a substituent; and M represents a divalent metal atom or has a substituent A trivalent or tetravalent metal atom of a radical.
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