CN114230515A - Yellow-based compound, coloring composition containing the same, colorant for color filter, and color filter - Google Patents
Yellow-based compound, coloring composition containing the same, colorant for color filter, and color filter Download PDFInfo
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- CN114230515A CN114230515A CN202111040971.5A CN202111040971A CN114230515A CN 114230515 A CN114230515 A CN 114230515A CN 202111040971 A CN202111040971 A CN 202111040971A CN 114230515 A CN114230515 A CN 114230515A
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Abstract
提高黄色系化合物在有机溶剂(PGMEA等)中的溶解性及耐热性。提供色彩特性优异的着色组合物、滤色器用着色剂及滤色器。由下述通式(1)表示的化合物。[式(1)中，Q分别独立地为由式(2)表示的基团，n表示2～10的整数，L表示2～10价的基团。R1～R9分别独立地表示H、羟基、卤素原子、氨基、磺酰基、烷基、烯基、烷氧基、酰基、‑O‑、芳香族烃基、杂环基等，可在相邻的基团之间相互键合而形成环。Z分别独立地为2价基团或3价基团，表示氨基、亚烷基、包含‑O‑或单键的基团，有多个的Q经由L或Z相互键合。]
The solubility and heat resistance of yellow-based compounds in organic solvents (PGMEA, etc.) are improved. Provided are coloring compositions, colorants for color filters, and color filters excellent in color characteristics. A compound represented by the following general formula (1). 
[In the formula (1), Q is each independently a group represented by the formula (2), n represents an integer of 2 to 10, and L represents a 2 to 10-valent group. R 1 to R 9 each independently represent H, a hydroxyl group, a halogen atom, an amino group, a sulfonyl group, an alkyl group, an alkenyl group, an alkoxy group, an acyl group, -O-, an aromatic hydrocarbon group, a heterocyclic group, etc., and may be adjacent to each other. The groups are bonded to each other to form a ring. Z is each independently a divalent group or a trivalent group, and represents an amino group, an alkylene group, a group containing -O- or a single bond, and a plurality of Qs are bonded to each other via L or Z. ]
Description
Technical Field
The present invention relates to a yellow compound, a coloring composition containing the compound, a coloring agent for a color filter containing the coloring composition, and a color filter using the coloring composition.
Background
Many pigments such as quinophthalone pigments, azo pigments, diketopyrrolopyrrole pigments, and the like have been developed (patent documents 1 to 4). These pigments are used as colorants for color filters of liquid crystal and Electroluminescent (EL) display devices. The color filter is produced by laminating colored layers on a light-transmitting substrate such as glass by a dyeing method, a pigment dispersion method, a printing method, an electrodeposition method, or the like. Quinophthalone pigments are yellow compounds synthesized by condensation of quinaldine and phthalic anhydride, and are used as colorants for color filters because of their distinctiveness (patent documents 1, 2, 5, and 6, and non-patent document 1). However, as the display is improved in image quality, the performance required of the color filter is improved, and further improvement in the coloring power, brightness, and contrast is required.
The pigment is generally insoluble in a solvent, and therefore exists in fine particles in a color filter including a resin or the like. Thus, it is known that: in a color filter using a pigment, the transmitted light is reflected and scattered on the surface of the pigment particles, which affects the transparency and color purity, and the contrast of a color liquid crystal display device is lowered due to a depolarization effect by reflection.
In order to improve the problem of contrast reduction, a method of using only a dye as a colorant, a method of using a dye and a pigment in combination, or the like has been proposed. Since the dye is soluble in a solvent, a color filter using the dye is expected to have a reduced depolarization effect, superior spectral characteristics, and improved contrast, brightness, and the like, as compared with a color filter using only a pigment as a colorant.
Documents of the prior art
Patent document
Patent document 1: japanese examined patent publication No. 47-3476
Patent document 2: japanese patent laid-open publication No. 2012 and 193318
Patent document 3: japanese laid-open patent publication No. 2012-12498
Patent document 4: japanese patent laid-open No. 2001-220520
Patent document 5: japanese patent laid-open publication No. 2019-104897
Patent document 6: japanese patent laid-open publication No. 2019-123856
Non-patent document
Non-patent document 1: the Hongkong Ministry of the village in the market, the most advanced color filter technology and chemistry, CMC published by Kabushiki Kaisha, 2006, page 80
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made to solve the above problems, and an object of the present invention is to provide: a coloring composition which is improved in the solubility and heat resistance of a yellow compound in an organic solvent (propylene glycol monomethyl ether acetate (PGMEA), etc.) and which is excellent in color characteristics such as coloring power, vividness, hue, etc. when it is contained, a coloring agent for a color filter containing the coloring composition, and a color filter using the coloring agent.
Means for solving the problems
The present invention has been made in detail for the above purpose, and the gist thereof is as follows.
1. A compound represented by the following general formula (1).
[ CHEM 1]
[ in the formula (1), Q is each independently a group represented by the following general formula (2),
n represents an integer of 2 to 10,
l represents a 2-10 valent group. ]
[ CHEM 2]
[ in the formula (2), R1～R9Each independently represent
Hydrogen atom (-H), hydroxyl group (-OH), halogen atom, cyano group (-CN), nitro group (-NO)2)、
An amino group having 0 to 25 carbon atoms which may have a substituent,
A C0-25 sulfonyl group which may have a substituent,
A linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent,
A linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms which may have a substituent,
A linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms which may have a substituent,
An optionally substituted acyl group having 1 to 25 carbon atoms,
An ether group having 0 to 25 carbon atoms which may have a substituent,
An optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or
A heterocyclic group having 5 to 25 ring-forming atoms which may have a substituent,
R1～R9adjacent groups may be bonded to each other to form a ring.
Z is respectively and independently a 2-valent group or a 3-valent group and represents
An amino group having 0 to 25 carbon atoms which may have a substituent,
A linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent,
Containing 1 or 2 or more of ether groups or single bonds,
a plurality of Q's are bonded to each other via L or Z. ]
2. Wherein, in the above general formula (1), L is
An amino group having 0 to 25 carbon atoms which may have a substituent,
A linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent,
An ether group having 0 to 25 carbon atoms which may have a substituent,
An optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or
A heterocyclic group having 5 to 25 ring-forming atoms which may have a substituent.
3. In the general formula (2), Z is an amino group having 1 to 20 carbon atoms which may have a substituent.
4. In the compound represented by the general formula (2), Z represents a linear, branched or cyclic alkylene group having 1 to 20 carbon atoms which may have a substituent, or a group containing an ether group.
5. A compound wherein, in the above general formula (2), R2Or R6An amino group having 1 to 20 carbon atoms which may have a substituent.
6. A compound wherein, in the above general formula (2), R2Or R6An ether group having 1 to 20 carbon atoms which may have a substituent.
7. A coloring composition containing the above compound.
8. A colorant for color filters, which contains the coloring composition.
9. And a color filter using the colorant for color filter.
ADVANTAGEOUS EFFECTS OF INVENTION
The compound according to the present invention has excellent solubility in an organic solvent such as PGMEA and excellent heat resistance during film formation, compared to conventional yellow compounds, and therefore, a colored composition containing the compound according to the present invention can be used as a colorant for color filters.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail. The present invention is not limited to the following embodiments, and various modifications can be made within the scope of the present invention. First, the compound represented by the above general formula (1) will be described.
The compound of the present invention is represented by the following general formula (1) or [ Q]n-L represents. In the general formula (1), Q is a group represented by the following general formula (2), n represents an integer of 2 to 10, and L represents a group having a valence of 2 to 10. Q's may be the same or different from each other.
[ CHEM 3]
[ CHEM 4]
Therefore, the general formula (1) can be represented by the general formula (2) as shown in the following general formulae (1-2).
[ CHEM 5 ]
Wherein, in the general formula (1), when n is 2, a plurality of Q are represented as Q1And Q2In the case of (2), Q is represented by the following formula (1-3)1And Q2Via L as "Q1-L-Q2And bonded as such.
[ CHEM 6 ]
Q1-L-Q2 (1-3)
Further, in the general formula (1), when n is 3, a plurality of Q's are represented by Q1、Q2And Q3In the case of (2), Q is represented by the following formula (1-4)1～Q3Can be bonded via L, Q1～Q3May be directly bonded to each other or may be substituted for each other. Similarly, when n is 4 or more, a plurality of Q's can be bonded to each other through L as in the following formula (1-4).
[ CHEM 7 ]
Thus, in the general formula (1), n represents an integer of 2 to 10 even when Q is present1～Q10In the case of plural Q's, Q1～Q10Can be bonded via L, Q1～Q10May be directly bonded to each other or may be substituted for each other. Therefore, L and n represent a group having a valence of 2 to 10, respectively. n is preferably 2 to 6, and more preferably 2 to 4.
As R in the general formula (2)1～R9Examples of the "halogen atom" include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like. The "halogen atom" is preferably a fluorine atom or a chlorine atom.
In the general formula (2), by R1～R9The "amino group having 0 to 25 carbon atoms which may have a substituent" may or may not have a substituent, and when having a substituent, it includes a group represented by "-NR10R11"is" having a substituent R10And R11Examples of the "amino group" of (1) include unsubstituted amino (-NH)2) Mono-substituted amino, di-substituted amino, and the like. The number of carbon atoms in the mono-or di-substituted amino group is, for example, 1 to 25, 1 to 20, or 2 to 10. The "amino group having 0 to 25 carbon atoms which may have a substituent" may be a group in which a "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms", "aromatic hydrocarbon group having 6 to 25 carbon atoms", "acyl group having 0 to 25 carbon atoms" or a "heterocyclic group having 5 to 25 ring atoms" described later is bonded via-NH-, -N < or-N ═ CH-. Examples of the mono-substituted amino group include an ethylamino group, a butylamino group, an acetylamino group, an amino group,Phenylamino groups, and the like. Examples of the di-substituted amino group include a dialkylamino group having 2 to 25 carbon atoms such as a dimethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, or a dihexylamino group; a C4-25 dialkenylamino group such as a diallylamino group; diphenylamino, N-acetyl-N-phenylamino, (N-butyl) -N-phenylamino, and the like.
In the general formula (2), from R1～R9The "C0-25 sulfonyl group which may have a substituent" means "SO2-R100"(or" -S (═ O)2-R100") having a substituent R100A sulfonyl group of (a). "-SO2-R100"may be a group containing no carbon atoms, and may be, for example," -SO3H' or "-SO containing an alkali metal atom" M3M' is adopted. The alkali metal atom "M" in the present invention includes a lithium atom (Li), a sodium atom (Na), a potassium atom (K), a cesium atom (Cs), and the like, and Li, Na, or K is preferable, Li or Na is more preferable, and Na is particularly preferable. R100The number of carbon atoms of (B) is 0 to 25, and may be 1 to 20, or 1 to 10. The C0-25 sulfonyl group which may have a substituent(s) is not limited to the above-mentioned-SO3H、-SO3Examples of the other than M include a sulfonamide group (-S (═ O)2-NH2) Methanesulfonyl, toluenesulfonyl and the like.
In the general formula (2), as represented by R1～R9The "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms" in the "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent(s)" includes, specifically, a linear alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, isooctyl, and 2-ethylhexyl; cyclic alkyl groups (cycloalkyl groups) such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl, 1-adamantyl and 2-adamantyl.
In the general formula (2), as represented by R1～R9The "carbon atom which may have a substituent(s)" represents"the linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms" in the linear, branched or cyclic alkenyl groups having 2 to 25 subgroups includes, specifically, linear or branched alkenyl groups such as vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 1-pentenyl, 1-hexenyl, isopropenyl and isobutenyl; a cyclic alkenyl group (cycloalkenyl group) such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group, or a group in which a plurality of these linear, branched, or cyclic alkenyl groups are bonded.
In the general formula (2), as represented by R1～R9The "linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms" in the "linear, branched or cyclic alkoxy group having 1 to 25 carbon atoms which may have a substituent(s)" includes, specifically, a linear alkoxy group such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy or decyloxy; branched alkoxy groups such as isopropoxy, isobutoxy, sec-butoxy, tert-butoxy, and isooctyloxy; cyclic alkoxy groups (cycloalkoxy groups) such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, cyclononyloxy, and cyclodecyloxy; 1-adamantyloxy group, 2-adamantyloxy group and the like.
In the general formula (2), from R1～R9The "acyl group having 1 to 25 carbon atoms which may have a substituent" means an acyl group represented by "- (C ═ O) -R101"represents a group having a substituent R101A group of (1). Substituent R101Either a group containing carbon atoms or a group containing no carbon atoms. At the substituent R101In the case of a group containing carbon atoms, the substituent R101The number of carbon atoms of (A) may be, for example, 1 to 25, and may be 1 to 20. As substituents R101Examples thereof include-H and-CH3、-CH2CH2CH3、-CH＝CH2、-C6H5(phenyl), and the like. The "acyl group having 1 to 25 carbon atoms" in the "acyl group having 1 to 25 carbon atoms which may have a substituent(s)" includes, specifically, formyl group, acetyl group, propionyl groupAcryl, benzoyl, and the like.
In the general formula (2), from R1～R9The "ether group having 0 to 25 carbon atoms which may have a substituent" means a compound represented by "-O-R102"represents a group having a substituent R102An ether group of (a). Substituent R102Either a group containing carbon atoms or a group containing no carbon atoms. The "ether group having 0 to 25 carbon atoms" in the "ether group having 0 to 25 carbon atoms which may have a substituent(s)" may specifically include an aminooxy group, an ester group represented by "— O- (C ═ O) -R" (R is an arbitrary alkyl group or an aromatic hydrocarbon group, etc.), a phosphoric acid group, a phosphate group, and the like.
In the general formula (2), as represented by R1～R9The "aromatic hydrocarbon group having 6 to 25 carbon atoms" in the "aromatic hydrocarbon group having 6 to 25 carbon atoms which may have a substituent(s)" may specifically include phenyl, biphenyl, terphenyl, naphthyl, anthryl (アントリル group), phenanthryl, fluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, benzo [9,10] benzo]An aromatic hydrocarbon group such as a phenanthryl group (the "aromatic hydrocarbon group" in the present invention also includes an aryl group or a condensed polycyclic aromatic group).
In the general formula (2), as represented by R1～R9The "heterocyclic group having 5 to 25 ring atoms" in the "heterocyclic group having 5 to 25 ring atoms which may have a substituent" includes, specifically, a heterocyclic group (or a heteroaromatic hydrocarbon group) such as a pyridyl group, a pyrimidyl group, a triazinyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a thienyl group, a furyl group (フラニル group), a pyrrolyl group, a quinolyl group, an isoquinolyl group, a naphthyridinyl group, an indolyl group, an acridinyl group, a phenanthrolinyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbolinyl group and the like.
In the general formula (2), as represented by R1～R9Of the representation
An amino group having 0 to 25 carbon atoms and having a substituent,
A "C0-25 sulfonyl group having a substituent group
"a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms and having a substituent group"),
"a linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms and having a substituent group"),
"straight-chain, branched or cyclic alkoxy group having 1 to 25 carbon atoms and having a substituent group"),
An acyl group having 1 to 25 carbon atoms and a substituent,
An "ether group having 0 to 25 carbon atoms and a substituent group
An "substituted aromatic hydrocarbon group having 6 to 25 carbon atoms", or,
The "substituent" of the "heterocyclic group having 5 to 25 ring-forming atoms and having a substituent",
specifically, there may be mentioned heavy hydrogen atoms, hydroxyl groups, thiol groups, cyano groups, nitro groups;
halogen atoms such as fluorine atom, chlorine atom, bromine atom, and iodine atom;
an amino group having 0 to 20 carbon atoms;
a sulfonyl group having 0 to 20 carbon atoms;
a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms;
a linear, branched or cyclic alkenyl group having 2 to 20 carbon atoms;
a straight-chain, branched or cyclic alkoxy group having 1 to 20 carbon atoms;
an acyl group having 1 to 20 carbon atoms;
an ether group having 1 to 20 carbon atoms;
an aromatic hydrocarbon group or a condensed polycyclic aromatic group having 6 to 20 carbon atoms;
heterocyclic groups having 5 to 20 ring atoms, and the like. When the "substituent" includes a carbon atom, the carbon atom is not limited to "0 to 25 carbon atoms", "1 to 25 carbon atoms", "2 to 25 carbon atoms", "6 to 25 carbon atoms" and "5 to 25 ring atoms" described above. As far as these "substituents" are concerned, they may contain only oneThe plural may be contained, and when the plural are contained, they may be the same as or different from each other. These "substituents" may further have the substituents exemplified above. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom (-O-) or a sulfur atom (-S-) to form a ring. However, the above-mentioned R group1～R9The number of "substituents" in each group shown is 10 at the maximum, and the maximum number of carbon atoms in each group is 100.
The general formula (2) is as defined by R1～R9The "substituent" of the above-mentioned groups having "substituent" may be,
An amino group having 0 to 20 carbon atoms,
A "C0-20 sulfonyl group
"a straight-chain, branched or cyclic alkyl group having 1 to 20 carbon atoms"),
"a straight-chain, branched or cyclic alkenyl group having 2 to 20 carbon atoms"),
"straight-chain, branched or cyclic alkoxy group having 1 to 20 carbon atoms"),
An acyl group having 1 to 20 carbon atoms,
An "ether group having 1 to 20 carbon atoms"),
An "aromatic hydrocarbon group or condensed polycyclic aromatic group having 6 to 20 carbon atoms", or
Specific examples of the "heterocyclic group having 5 to 20 ring-forming atoms" include
An amino group; a mono-or di-substituted amino group having a straight-chain or branched alkyl group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms, such as a methylamino group, dimethylamino group, diethylamino group, ethylmethylamino group, dipropylamino group, di-tert-butylamino group, diphenylamino group, or the like;
sulfonamide (-S (═ O)2-NH2) A sulfonyl group having 0 to 20 carbon atoms (-S (═ O), such as a methylsulfonyl group, a toluenesulfonyl group or the like2-) of; -SO3 -、-SO3H、-SO3M (M is an alkali metal atom);
a straight-chain or branched alkyl group having 1 to 20 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, a 2-ethylhexyl group, a heptyl group, an octyl group, an isooctyl group, a nonyl group, or a decyl group; a cyclic alkyl group (cycloalkyl group) having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, or a cyclodecyl group; 1-adamantyl, 2-adamantyl;
a vinyl group, a 1-propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 1-pentenyl group, a 1-hexenyl group, an isopropenyl group, an isobutenyl group, or a straight-chain alkenyl group having 2 to 20 carbon atoms or a branched alkenyl group having 3 to 20 carbon atoms to which a plurality of these alkenyl groups are bonded; a cyclic alkenyl group (cycloalkenyl group) having 3 to 20 carbon atoms such as a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group;
a straight-chain or branched alkoxy group having 1 to 20 carbon atoms or 3 to 20 carbon atoms such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an isopropoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, or an isooctyloxy group; a cyclic alkoxy group (cycloalkoxy group) having 3 to 20 carbon atoms such as a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cyclononyloxy group, a cyclodecyloxy group and the like; 1-adamantyloxy group, 2-adamantyloxy group;
acyl groups having 1 to 20 carbon atoms such as formyl group, acetyl group, propionyl group, acryloyl group, and benzoyl group;
an ether group (-O-) containing group having 0 to 20 carbon atoms such as an ether group (-O-), an aminoxy group, an ester group represented by "— O- (C ═ O) -R" (R is an arbitrary alkyl group, an aromatic hydrocarbon group, or the like), a phosphoric acid group, or a phosphate group;
an aromatic hydrocarbon group or a condensed polycyclic aromatic group having 6 to 20 carbon atoms such as a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group (アントリル group), a phenanthryl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a benzo [9,10] phenanthryl group, and the like;
a heterocyclic group having 5 to 20 ring atoms such as a pyridyl group, a pyrimidyl group, a triazinyl group, a thienyl group, a furyl group (フラニル group), a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a quinolyl group, an isoquinolyl group, a naphthyridinyl group, an acridinyl group, a phenanthrolinyl group, a benzofuranyl group, a benzothiophenyl group, an oxazolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbolinyl group and the like;
and aryloxy groups having 6 to 19 carbon atoms such as phenoxy, tolyloxy, biphenyloxy, naphthyloxy, anthracenyloxy, phenanthrenyloxy, and the like.
In the general formula (2), R1～R9Adjacent groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom to form a ring.
In the general formula (2), as R1～R9Preference is given to
Hydrogen atom, hydroxyl group, halogen atom, nitro group, cyano group,
An amino group having 1 to 20 carbon atoms which may have a substituent,
A linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent(s),
A linear or branched alkenyl group having 2 to 20 carbon atoms which may have a substituent,
A linear or branched alkoxy group having 2 to 20 carbon atoms which may have a substituent(s),
An optionally substituted acyl group having 1 to 20 carbon atoms,
An ether group having 1 to 20 carbon atoms which may have a substituent, or
An optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
more preferably a hydrogen atom, an amino group having 1 to 20 carbon atoms which may have a substituent, or an ether group having 1 to 20 carbon atoms which may have a substituent. Further preferred is R2Or R6Is an amino group having 1 to 20 carbon atoms which may have a substituent, or a carbon atom which may have a substituentA sub-number of 1 to 20 ether groups.
In the general formula (1), n Q represented by the general formula (2) are contained. In the general formula (2), a plurality of (n) Z's may be the same or different and each Z's is a 2-valent group or a 3-valent group.
In the general formula (1), a plurality of Q's are bonded to each other via L or Z. In the case where Z is a 2-valent group, for example, in the above-mentioned general formula (1) such as "Q1-L-Q2"is expressed as the following formula (2-1). In this case, there are a plurality of R1～R9Each independently may be the same or different. In addition, in the following formula (2-1) cases, there are a plurality of Z any one or more can be a 3 valence group, Z can be suitable groups, for example with R12The 3-valent group of (3) can be specifically represented by the following formula (2-2). With a plurality of R12Each independently may be the same or different.
[ CHEM 8 ]
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In the general formula (1), when a plurality of Q are bonded via Z, each Q may be bonded to each other via a 2-valent group or a 3-valent group represented by Z, as in the following formula (2-3), for example.
[ CHEM 10]
In the general formula (1), the group represented by "L" represents a group having a valence of 2 to 10, and specific examples of L include groups having a valence of 2 to 10 formed by using any of the following groups. L and Q may be bonded to each other at a site of an arbitrary substituent of the following groups.
As these groups, there may be mentioned
"an amino group (or imino group) having 0 to 25 carbon atoms which may have a substituent(s)
A "C0-25 sulfonyl group which may have a substituent group"),
"optionally substituted straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms"),
"optionally substituted straight-chain, branched or cyclic alkenyl group having 2 to 25 carbon atoms"),
"optionally substituted straight-chain, branched or cyclic alkoxy group having 1 to 25 carbon atoms"),
An optionally substituted acyl group having 1 to 25 carbon atoms,
An "ether group having 0 to 25 carbon atoms which may have a substituent group"),
An "optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms", or
"a heterocyclic group having 5 to 25 ring-forming atoms which may have a substituent".
Specific examples of these groups include R in the general formula (2)1～R9The groups listed are the same. As the "substituent" which these "groups" may have, there may be mentioned1～R9The groups represented may have the same groups as the "substituents".
L represented by these groups can be a group having an arbitrary valence of 2 to 10 by the number (n) of Q or a bond with a plurality of Q of optional substituent-optionally substituted sites. For example, the "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent" may be "linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent", and the substituent may be bonded to a part of these "alkylene groups" and may have a valence of 3 or more. These "groups" or "substituents" may be contained in only 1 number, or may be contained in plural numbers, and in the case of containing plural numbers, they may be the same as or different from each other. In addition, these "groups" or "substituents" may further have the groups or substituents exemplified above. Further, these "groups" or "substituents" may form a ring by bonding to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. However, the number of the above-mentioned "groups" or "substituents" contained in L is 10 at most, and the maximum number of carbon atoms in each group is 100.
In the general formula (1), L is preferably
An amino group having 0 to 25 carbon atoms which may have a substituent,
A linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent,
An ether group having 0 to 25 carbon atoms which may have a substituent,
An optionally substituted aromatic hydrocarbon group having 6 to 25 carbon atoms, or
A heterocyclic group having 5 to 25 ring-forming atoms which may have a substituent,
more preferably a linear or branched alkylene group having 1 to 25 carbon atoms which may have a substituent.
In the general formula (2), the 2-valent group or the 3-valent group represented by Z
An amino group having 0 to 25 carbon atoms which may have a substituent,
A linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent,
The group containing 1 or 2 or more of ether groups or single bonds includes a group obtained by replacing these groups with a 2-valent group or a 3-valent group at an appropriate position. These amino, alkylene or ether groups may also contain a plurality of the same or different groups.
In Z in the general formula (2), examples of the "amino group having 0 to 25 carbon atoms" in the "amino group having 0 to 25 carbon atoms which may have a substituent" include a group which is bonded to-N < -, -N ═ CH-, or a group represented by R in the general formula (2)1～R9The same group as the "amino group having 0 to 25 carbon atoms which may have a substituent" as described above is a group wherein a 2-valent group or a 3-valent group is substituted at the site of any substituent,by the substituent R12Can be represented by-NR12-、＞N-R12-、-R12-NR12-R12-、-R12-NH-NR12-R12-and the like. With respect to substituent R12In addition, R is exemplified1～R9The same groups as the "substituents" in the "amino group having 0 to 25 carbon atoms which may have a substituent" are mentioned. Plural R12May be the same or different. In the general formula (2), when Z includes a plurality of "amino groups having 0 to 25 carbon atoms which may have a substituent", each Q may be bonded to a different Q via Z.
In the general formula (2), the "linear, branched or cyclic alkylene group having 1 to 25 carbon atoms which may have a substituent" represented by Z is exemplified by a group represented by R1～R9The 1-valent group having the same structure as the "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent" is a group in which a substituent at an arbitrary position is replaced with a 2-valent group. The "substituent" in the "optionally substituted linear, branched or cyclic alkylene group having 1 to 25 carbon atoms" may be exemplified by1～R9The same groups as the "substituent" in the "linear, branched or cyclic alkyl group having 1 to 25 carbon atoms which may have a substituent" are mentioned. These alkylene groups may be branched to form a 3-valent group.
In the general formula (2), Z is a 2-valent group or a 3-valent group, and is preferably an amino group having 1 to 20 carbon atoms which may have a substituent, a linear, branched or cyclic alkylene group having 1 to 20 carbon atoms which may have a substituent, or a group containing an ether group.
In the above, it is to be noted that, in the above,
the "C1-25 linear, branched or cyclic alkyl group" is preferably "C1-25 linear, or C3-25 branched or cyclic alkyl group".
The "linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms" is preferably a "linear, branched or cyclic alkenyl group having 2 to 25 carbon atoms" or a branched or cyclic alkenyl group having 3 to 25 carbon atoms ".
The "C1-25 linear, branched or cyclic alkoxy group" is preferably a "C1-25 linear, or C3-25 branched or cyclic alkoxy group".
The "linear, branched or cyclic alkylene group having 1 to 25 carbon atoms" is preferably a "linear, branched or cyclic alkylene group having 1 to 25 carbon atoms" or a branched or cyclic alkylene group having 3 to 25 carbon atoms ".
The compounds of the invention are prepared from
1 of 2 to 10-valent groups L [ is synonymous with L in the general formula (1). H,
n identical or different 1-valent groups R represented by the following general formula (3)0、
n identical or different radicals R having a valence of 112[ synonymous with the substituent in the general formula (2) or a hydrogen atom.]And, and
n identical or different 2-or 3-valent radicals Z [ are synonymous with Z in the formula (2). Consists of, or contains the above-mentioned groups,
n represents an integer of 2 to 10,
l is bonded to only Z and is,
R0is bonded only to the Z-bond,
R12is bonded only to the Z-bond,
z and R0Bonded to and selected from L, R12And 1 or 2 linkages in other Z.
[ CHEM 11 ]
[ in the formula (3), R1～R9Are synonymous with the above.]
The compound represented by the general formula (1) (hereinafter, simply referred to as compound (1)) includes all stereoisomers and tautomers that can be produced. Specific examples of the compound (1) are shown below, but the present invention is not limited to these. In the following structural formulae, a part of hydrogen atoms is omitted.
[ CHEM 12 ]
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The compound represented by the general formula (1) can be synthesized by the following method. In the following, n is 2 and R is shown in the general formula (1)6Is any of-NR10R11Z is an optional substituent R12Examples of the synthesis of the amino group of (1).
The following intermediate (X-1) having a corresponding substituent is obtained by subjecting an 8-amino-2-methylquinoline derivative having a corresponding substituent to dehydration condensation reaction with trimellitic anhydride in a suitable solvent at a suitable temperature.
[ CHEM 35 ]
Further, the compound of the present invention represented by the general formula (1) can be obtained by using a dehydration condensation agent in an appropriate solvent at an appropriate temperature together with the obtained intermediate (X-1) and a diamine having a corresponding substituent.
In the present invention, as a method for purifying the product, purification by column chromatography; adsorption refining with silica gel, active carbon, activated clay, etc.; known methods such as recrystallization from a solvent and crystallization are used. In the identification and analysis of these compounds, nuclear magnetic resonance analysis (NMR), absorbance measurement by a spectrophotometer, ultraviolet-visible absorption spectroscopy (UV-Vis) measurement, thermogravimetry-differential thermal analysis (TG-DTA), and the like can be performed. These analysis methods can also be used for the solubility, color evaluation, and heat resistance evaluation of the obtained compound.
The solubility of the compound of the present invention is expressed by solubility, which indicates the proportion of the maximum amount of a substance that can be dissolved in a specific solvent, and is expressed in units such as "mass% (solvent name, temperature)". The solubility is obtained by, for example, mixing a sample in a specific solvent, stirring the solvent at a certain temperature for a certain period of time, and measuring the concentration of the prepared saturated solution, and is also obtained by concentration measurement such as Liquid Chromatography (LC) and absorbance measurement using a dissolution part.
By performing thermogravimetry-differential thermal analysis (TG-DTA) of the compound of the present invention, the thermal decomposition temperature can be analyzed, and can be used as an index of heat resistance. In the coloring composition, the thermal decomposition temperature of the compound of the pigment part is preferably 250 ℃ or higher. In the case of application to color filters, the higher the thermal decomposition temperature, the more preferable.
The compound of the present invention can be mixed with various resin solutions and applied onto a glass substrate to form a coating film. The color of the obtained coating film was measured by a spectrocolorimeter to obtain a color value of the coating film, whereby the color characteristics could be evaluated. Color values are typically measured using CIE L*a*b*Color system, etc. Specifically, the color value L of the film sample was measured*、a*、b*According to the color difference (Delta E) of the color values before and after heating at an appropriate temperature* ab) The heat resistance can be judged. When applied to a color filter, color difference at a temperature of about 230 ℃ can be used as an index of heat resistance. Is related to Delta E* abIn addition, a smaller value means a smaller color change due to thermal decomposition than the comparison target, and therefore, is preferably 3 or less. The more the coloring compound is reduced in color change due to thermal decomposition, the more excellent the coloring properties such as coloring power, vividness and hue, the coloring composition and the coloring agent for color filter can be obtained.
In the coloring composition contained in the colorant for color filters, since the coloring compound needs to be well dissolved or dispersed in the resin and the organic solvent, the compound contained in the coloring composition preferably has high solubility in the organic solvent. Specific examples of the organic solvent include esters such as ethyl acetate and n-butyl acetate; ethers such as diethyl ether and Propylene Glycol Monomethyl Ether (PGME); ether esters such as Propylene Glycol Monomethyl Ether Acetate (PGMEA); ketones such as acetone and cyclohexanone; alcohols such as methanol and ethanol; diacetone alcohol (DAA), etc.; aromatic hydrocarbons such as benzene, toluene, and xylene; amides such as N, N-Dimethylformamide (DMF) and N-methylpyrrolidone (NMP); dimethyl sulfoxide (DMSO), and the like. These solvents may be used alone, or 2 or more of them may be used in combination. Among these, the compound according to the present invention is excellent in solubility in PGME and PGMEA, and for example, the solubility (mass%) in PGMEA (solvent PGMEA, 25 ± 2 ℃) at room temperature in a temperature range of 25 ± 2 ℃ (any temperature between 23 and 27 ℃) is preferably 0.1 mass% or more, more preferably 1 mass% or more, and particularly preferably 2 mass% or more.
The compound represented by the general formula (1) preferably has a maximum absorption wavelength in the visible light region, for example, in the range of 350 to 700nm, in the range of 400 to 500nm in a solution.
The coloring composition of the present invention contains the compound of the present invention represented by the general formula (1), and may contain 1 kind of structural compound, or may contain 2 or more kinds of structural compounds. In the present invention, the structure of the compound is preferably 1.
In the coloring composition of the present invention, in order to improve the performance as a coloring agent for color filters, a surfactant, a dispersant, an antifoaming agent, a leveling agent, an additive to be mixed in the production of another coloring agent for color filters, and the like can be added as components other than the compound. However, the content of these additives in the coloring composition is preferably an appropriate amount, and is preferably a content within a range that does not reduce the solubility of the coloring composition or excessively improve the solubility and does not affect the production of a color filter. These additives can be added at any timing in the preparation of the coloring composition.
The colorant for color filters of the present invention comprises: a colored composition containing a compound represented by the general formula (1), and a component generally used in the production of a color filter. In a general color filter, for example, in the case of a method using a photolithography process, a liquid prepared by mixing a dye such as a dye or a pigment with a resin component (including a monomer, an oligomer, a binder component, and a resist component) and a solvent is applied onto a substrate such as glass or resin, and the mixture is photopolymerized using a photomask to form a colored pattern of a dye-resin composite film soluble/insoluble in the solvent, and the colored pattern is cleaned and then heated to obtain the color filter. The compound of the present invention has excellent solubility and therefore excellent dispersibility in materials used for producing color filters, and therefore can be mixed with other materials and formed into films as needed to evaluate heat resistance and light absorption characteristics. In addition, in the electrodeposition method and the printing method, a colored pattern can be produced using a mixture of a pigment, a resin, and other components. Specific components in the colorant for color filters of the present invention include compounds represented by the general formula (1), other dyes, pigments such as pigments, resin components, organic solvents, and other additives such as photopolymerization initiators. Further, these components may be selected from them, or other components may be added as necessary.
When the colored composition of the present invention is used as a colorant for color filters, it can be used as a yellow color filter, and can also be mixed with a color filter for other colors such as red and green. The coloring composition of the present invention may be used alone, and other known coloring matters such as dyes and pigments may be mixed for adjusting the color tone. For example, basic dyes; an acid dye; a disperse dye; a spiroketone dye; azo-based, disazo-based, quinoline-based, stilbene-based, (poly) methine-based, cyanine-based, indigo-based, phthalocyanine-based, anthraquinone-based, acridine-based, triarylmethane-based, indanthrone-based, oxazine-based, dioxazine-based, naphthol AS-based, benzimidazolone-based, pyrazolone-based, perylene-based, peryleneketone-based, quinacridone-based, isoindolinone-based, xanthene-based, diketopyrrolopyrrole-based dyes or pigments.
The mixing ratio of the other pigments in the coloring composition and the coloring agent for color filters of the present invention is preferably 5 to 2000% by mass, more preferably 10 to 1000% by mass, based on the compound represented by the general formula (1). The mixing ratio of the coloring matter component such as dye in the liquid coloring agent for color filter is preferably 0.5 to 70% by mass, more preferably 1 to 50% by mass, based on the entire coloring agent.
As the resin component in the coloring composition and the colorant for color filters of the present invention, a known resin component can be used as long as it has properties required for the production method and use of a color filter resin film formed by using them. Examples thereof include acrylic resins, olefin resins, styrene resins, polyimide resins, urethane resins, polyester resins, epoxy resins, vinyl ether resins, phenol (novolac) resins, other transparent resins, photocurable resins, thermosetting resins, binder resins, and photoresist resins, and these resins can be used in combination as appropriate. In addition, copolymers of these resins may be used in combination. The content of the resin in the colorant for color filters is preferably 5 to 95% by mass, more preferably 10 to 50% by mass, in the case of a liquid colorant.
As other additives in the coloring composition and the color filter colorant of the present invention, components necessary for polymerization and curing of a resin such as a photopolymerization initiator and a crosslinking agent can be mentioned, and a surfactant, a dispersant and the like necessary for stabilizing the properties of components in a liquid color filter colorant can be mentioned. Any known substance can be used for these, and is not particularly limited. The mixing ratio of the total amount of these additives in the entire solid content of the colorant for color filters is preferably 5 to 60% by mass, and more preferably 10 to 40% by mass.
Examples
The embodiments of the present invention will be described specifically below with reference to examples, but the present invention is not limited to the examples below. It should be noted that, in the synthetic examples, with respect to the identification of the compounds, the identification was carried out by1H-NMR analysis (Ascend, manufactured by Bruker Co., Ltd.)TM400) To proceed with.
Synthesis example 1 Synthesis of Compound (A-3)
5.0g of 8-amino-2-methylquinoline, 23.3g of 1-iodobutane, 17.5g of potassium carbonate and 10 g of DMF10mL were placed in a reaction vessel and stirred at 80 ℃ for 17 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/heptane 1/3 (vol.%)) to give 8- (N, N-dibutylamino) quinaldine (7.6g, 89% yield).
Then, 7.1g of the 8- (N, N-dibutylamino) quinaldine obtained above, 3.9g of trimellitic anhydride, 2.5g of benzoic acid, and 16mL of 1, 2, 4-trichlorobenzene were put into a reaction vessel, and the mixture was stirred at 180 ℃ for 8 hours. After cooling to 25 ℃, 20mL of toluene was added to the reaction mixture, followed by filtration to obtain the following intermediate (100) (8.2g, yield 90%).
[ CHEM 36 ]
Subsequently, 5.7g of the intermediate (100) obtained above, 1.1g of N, N' -diethyl-1, 6-diaminohexane, 2.6g of triethylamine, DMF33mL, and 6.1g of 1- [ bis (dimethylamino) methylene ] -1H-1, 2, 3-triazolo [4, 5-b ] pyridinium 3-oxide Hexafluorophosphate (HATU) were placed in a reaction vessel, and the mixture was stirred at 25 ℃ for 5 hours. Water was added to the reaction solution, followed by extraction with methylene chloride. The extract was concentrated under reduced pressure, and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/ethyl acetate 3/1 (vol.%)) to give (a-3) as a yellow powder (5.2g, yield 79%).
The obtained yellow powder was subjected to NMR measurement, and the following 76 hydrogen signals were detected, and the structure of the compound represented by the following formula (a-3) was identified.
1H-NMR(400MHz、CDCl3)：δ(ppm)＝14.40(2H)、8.12(2H)、8.22(2H)、7.64-7.85(4H)、7.48-7.64(6H)、7.42(2H)、3.10-3.80(16H)、1.00-1.90(30H)、0.80-1.00(12H)。
[ CHEM 37 ]
Synthesis example 2 Synthesis of Compound (A-4)
8.0g of 8-amino-2-methylquinoline, 6.7g of triethylamine and 64mL of dichloromethane were placed in a reaction vessel, and the mixture was cooled to 5 ℃ or lower with an ice bath. 13.8g of 2, 4, 6-trimethylbenzoyl chloride was slowly charged and stirred at 25 ℃ for 7 hours. Water was added to the reaction solution, followed by extraction with methylene chloride. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: heptane/dichloromethane/ethyl acetate 10/3/1 (volume ratio)). Heptane was added to the reaction mixture, followed by filtration to give N- (2, 4, 6-trimethylbenzoyl) -8-aminoquinaldine (11.8g, yield 77%).
Subsequently, 2.5g of sodium hydride and dehydrated DMF48mL were placed in the reaction vessel 1, and cooled to 5 ℃ or lower with an ice bath. In a separate reaction vessel 2, a solution was prepared in which 9.5g of the above-described N- (2, 4, 6-trimethylbenzoyl) -8-aminoquinaldine was dissolved in dehydrated DMF48 mL. The solution in the reaction vessel 2 was slowly dropped into the reaction vessel 1, and stirred at 25 ℃ for 2 hours. 6.9g of 1-iodopropane was charged, and the mixture was stirred at 25 ℃ for 2 hours. 150mL of methylene chloride was added to the reaction mixture, and 150mL of water was slowly dropped, followed by extraction with methylene chloride. The extract was concentrated under reduced pressure and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/heptane 1/1 (vol.%)) to give N- (2, 4, 6-trimethylbenzoyl) -N-propyl-8-aminoquinaldine (10.0g, 93% yield).
Subsequently, 9.4g of N- (2, 4, 6-trimethylbenzoyl) -N-propyl-8-aminoquinaldine, 4.0g of trimellitic anhydride, 2.5g of benzoic acid, and 16mL of 1, 2, 4-trichlorobenzene were placed in a reaction vessel, and the mixture was stirred at 180 ℃ for 8 hours. After cooling to 25 ℃, 40mL of toluene was added to the reaction mixture, followed by filtration to obtain the following intermediate (101) (8.0g, yield 74%).
[ CHEM 38 ]
Subsequently, 4.5g of the intermediate (101), 0.8g of N, N' -diethyl-1, 6-diaminohexane, 1.8g of triethylamine, DMF23mL, and HATU4.1g were placed in a reaction vessel, and stirred at 25 ℃ for 6 hours. Water was added to the reaction solution, followed by extraction with methylene chloride. The extract was concentrated under reduced pressure, and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/ethyl acetate 3/1 (vol.%)) to give (a-4) as a yellow powder (4.4g, 92% yield).
The obtained yellow powder was subjected to NMR measurement, and the following 76 hydrogen signals were detected, and the structure of the compound represented by the following formula (a-4) was identified.
1H-NMR(400MHz、CDCl3)：δ(ppm)＝14.00-14.60(2H)、8.60-8.80(2H)、8.25-8.50(1H)、7.98-8.20(2H)、7.50-7.90(6H)、7.30-7.43(2H)、7.10-7.25(3H)、6.90-7.08(2H)、6.72(1H)、6.41(1H)、5.10(1H)、3.10-3.80(10H)、2.80(6H)、2.60-2.72(2H)、2.48(4H)、2.35(2H)、2.09(2H)0.95-2.05(24H)、0.80-0.90(1H)、0.81(2H)。
[ CHEM 39 ]
Synthesis example 3 Synthesis of Compound (B-1) of comparative example
2.0g of the following intermediate (102) obtained in the same manner as in Synthesis example 1 (the same manner was adopted except that the dibutylamino group of intermediate (100) was replaced with the dipropylamino group), 0.7g of N, N' -dibutylamine, 0.8g of triethylamine, 10 g of DMF10mL and 9g of HATU1.9 were placed in a reaction vessel, and the mixture was stirred at 25 ℃ for 2 hours. Water was added to the reaction solution, followed by extraction with methylene chloride. The extract was concentrated under reduced pressure, and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/ethyl acetate 3/1 (vol.%)) to give (B-1) as a yellow powder (1.7g, yield 70%).
[ CHEM 40 ]
The obtained yellow powder was subjected to NMR measurement, and the following 41 hydrogen signals were detected, and the compound was identified as the structure of the compound represented by the following formula (B-1).
1H-NMR(400MHz、CDCl3)：δ(ppm)＝14.00(1H)、8.76(1H)、8.12(1H)、7.67-7.81(2H)、7.50-7.60(3H)、7.43(1H)、3.52(2H)、3.10-3.30(6H)、1.62-1.75(2H)、1.40-1.58(8H)、1.16(2H)、1.01(3H)、0.88(6H)、0.80(3H)。
[ CHEM 41 ]
Synthesis example 4 Synthesis of Compound (B-2) of comparative example
5.0g of the above intermediate (101), 1.6g of N, N' -dibutylamine, 1.9g of triethylamine, 50 g of DMF50mL, and HATU4.8g were placed in a reaction vessel, and the mixture was stirred at 25 ℃ for 2 hours. Water was added to the reaction solution, followed by extraction with methylene chloride. The extract was concentrated under reduced pressure, and purified by column chromatography (carrier: silica gel, solvent: dichloromethane/ethyl acetate 3/1 (vol.%)) to give (B-2) as a yellow powder (5.0g, yield 83%).
The obtained yellow powder was subjected to NMR measurement, and the following 45 hydrogen signals were detected, and the structure of the compound represented by the following formula (B-2) was identified.
1H-NMR(400MHz、CDCl3)：δ(ppm)＝14.00-14.60(1H)、8.60-8.80(1H)、7.98-8.16(1H)、7.62-7.84(3H)、7.48-7.62(2H)、7.10-7.40(1H)、6.40-7.05(2H)、5.10(0.5H)、3.40-3.80(2.5H)、3.10-3.30(3H)、2.69(1H)、2.48(3H)、2.36(1H)、2.10(1H)、1.30-2.00(12H)、0.68-1.25(10H)。
[ CHEM 42 ]
[ example 1]
For the compound (A-3) obtained in Synthesis example 1, the solubility (% by mass) in a PGMEA solvent at room temperature was measured (solvent PGMEA, 25. + -. 2 ℃ C.). The solubility was evaluated on the basis of the measured solubility value by the following 4 grades. The results are shown in table 1.
"verygood": solubility of 2 mass% or more
". o": 1 to less than 2% by mass
". DELTA": 0.1% by mass or more and less than 1% by mass
"×": less than 0.1% by mass
5.0g of a 2 mass% DMF-PGMEA mixed solution of a copolymer of methacrylic acid, acrylic ester and styrene and 20mg of the compound (A-3) obtained in Synthesis example 1 were put in a sample bottle and mixed with stirring for 30 minutes. The obtained colored resin solution was applied to a glass substrate, and heated at 100 ℃ for 2 minutes to form a film. The color value of the obtained film was measured by a spectrophotometer (CM-5, manufactured by Konika Minnta K.K.). Then, the color value was measured in the same manner by heating at 230 ℃ for 2 times for 20 minutes. The difference in color value (Δ E) between before and after heating at 230 ℃ was measured* ab) The results are shown in Table 1 as an index of heat resistance.
[ example 2]
The solubility (mass%) in a PGMEA solvent at room temperature (solvent PGMEA, 25 ± 2 ℃) was measured by the same method as in example 1 except that the compound (a-4) obtained in synthesis example 2 was used instead of (a-3) as a compound, and a color difference (Δ E) of a color value before and after heating at 230 ℃ was measured with respect to a film formed thereon* ab) And evaluated. The results are summarized in table 1.
Comparative examples 1 and 2
The solubility (% by mass) in a PGMEA solvent (solvent PGMEA, 25. + -. 2 ℃ C.) at room temperature was measured in the same manner as in example 1 except that the compounds (B-1) and (B-2) obtained in Synthesis examples 3 and 4, which are dye compounds not belonging to the present invention, were used instead of (A-3) as the compounds. In addition, the color difference (Δ E) of the color value before and after heating at 230 ℃ was measured for the film formed* ab) And evaluated. The results are summarized in table 1.
[ TABLE 1]
| Compound (I) | Solubility in water | Color difference | |
| Example 1 | (A-3) | ◎ | 1.9 |
| Example 2 | (A-4) | ◎ | 2.2 |
| Comparative example 1 | (B-1) | ◎ | 2.7 |
| Comparative example 2 | (B-2) | ◎ | 3.8 |
As shown in table 1, the compounds of examples of the present invention exhibited high solubility in PGMEA and high heat resistance at the time of film formation, and the coloring compositions containing the compounds of the present invention had no problem in practical use as colorants for color filters. In addition, the film had higher heat resistance than the comparative example during film formation, and was excellent as a colorant for color filters.
Industrial applicability
The coloring composition containing the compound (yellow compound) according to the present invention is excellent in solubility in an organic solvent (PGMEA or the like) and excellent in heat resistance at the time of film formation, and therefore can be used as a coloring material for various applications such as a coloring agent for a color filter.
Claims (9)
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| KR20200136165A (en) * | 2019-05-27 | 2020-12-07 | 주식회사 엘지화학 | Compound, colorant composition comprising same, photosensitive resin composition, photosensitive material, color filter, display device comprising same |
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| JPS473476Y1 (en) | 1969-12-27 | 1972-02-05 | ||
| JP4785222B2 (en) | 2000-02-09 | 2011-10-05 | 東洋インキＳｃホールディングス株式会社 | Color filter pigment, process for producing the same, color filter coloring composition using the same, and color filter |
| JP5651389B2 (en) | 2010-06-30 | 2015-01-14 | 富士フイルム株式会社 | Pigment composition, ink for ink jet recording, coloring composition for color filter, and color filter |
| JP2012193318A (en) | 2011-03-18 | 2012-10-11 | Toyo Ink Sc Holdings Co Ltd | Method for producing pigment composition |
| JP7168417B2 (en) | 2017-12-11 | 2022-11-09 | 保土谷化学工業株式会社 | Yellow compound, coloring composition containing said compound, colorant for color filter and color filter |
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- 2021-08-02 TW TW110128290A patent/TW202222989A/en unknown
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| GB1357974A (en) * | 1970-12-16 | 1974-06-26 | Ciba Geigy Ag | Method for the photoelectrophoretic production of images using o'ganic pigments |
| US4279802A (en) * | 1978-08-01 | 1981-07-21 | Ciba-Geigy Corporation | Method for the production of a pigment preparation for coloring linear polyesters in the melt |
| US4458073A (en) * | 1982-01-18 | 1984-07-03 | Montefluos S.P.A. | Quinophthalonic dyes containing silane groups and process for preparing same |
| JP2012082337A (en) * | 2010-10-13 | 2012-04-26 | Yamamoto Chem Inc | Quinophthalone compound and coloring composition |
| CN110041254A (en) * | 2018-01-15 | 2019-07-23 | 保土谷化学工业株式会社 | Yellow based compound, the coloured composition containing the compound, colour filter colorant and colour filter |
| KR20200136165A (en) * | 2019-05-27 | 2020-12-07 | 주식회사 엘지화학 | Compound, colorant composition comprising same, photosensitive resin composition, photosensitive material, color filter, display device comprising same |
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