JP2021155712A - Compound, colorant, and colored resin composition - Google Patents

Abstract

To provide a colored resin composition capable of forming a color filter excellent in light fastness, a colorant contained in the colored resin composition, and a benzoperylene compound useful as a dye.SOLUTION: The colorant comprises at least two compounds represented by formula (I), where the two compounds represented by formula (I) differ from each other at least in R1 in the formula (I).SELECTED DRAWING: None

Description

The present invention relates to a benzoperylene compound useful as a dye, a colorant containing a benzoperylene compound, and a colored resin composition containing the benzoperylene compound as a colorant.

The colored resin composition is used in the manufacture of color filters used in display devices such as liquid crystal displays, electroluminescence display devices, and plasma displays. Such a colored resin composition contains a colorant in order to obtain a desired color tone and the like, and a perylene compound represented by the following formula (x) is known as the colorant (Non-Patent Document 1). ).

BASF Technical Report (Lumogen® F), BASF, November 1997, 2-6

However, as a result of studies by the present inventors, it has been found that a color filter formed from a colored resin composition using the above-mentioned perylene compound as a colorant, which is conventionally known, may not be sufficiently satisfactory in light resistance. bottom. Therefore, it is an object of the present invention to provide a colored resin composition capable of forming a color filter having excellent light resistance, a colorant contained in the colored resin composition, and a benzoperylene compound useful as a dye.

［式（Ｉ）中、
Ｒ¹及びＲ²は、互いに独立に、置換基を有してもよい炭素数１〜３０の炭化水素基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。
Ｒ³及びＲ⁸は、互いに独立に、置換基を有してもよい炭素数１〜３０の炭化水素基、置換基を有してもよい炭素数１〜３０の芳香族複素環基、又はこれらを組み合わせた基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。
Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁹及びＲ¹⁰は、互いに独立に、水素原子、−Ｒ¹¹、ハロゲン原子、ヒドロキシ基、カルボキシ基又はニトロ基を表す。
Ｒ⁴とＲ⁵、Ｒ⁵とＲ⁶及びＲ⁶とＲ⁷は、互いに結合して、−Ｒ¹²−ＣＯ−Ｏ−ＣＯ−Ｒ¹³−又は−Ｒ¹²−ＣＯ−Ｎ（Ｒ¹¹）−ＣＯ−Ｒ¹³−で表される基を形成してもよい。
Ｒ¹¹は、置換基を有してもよい炭素数１〜３０の炭化水素基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。Ｒ¹¹が複数ある場合、それらは互いに同じでも異なっていてもよい。
Ｒ¹²及びＲ¹³は、互いに独立に、単結合又は置換基を有してもよい炭素数１〜１５の２価の炭化水素基を表し、該２価の炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。Ｒ¹²が複数ある場合、それらは互いに同じでも異なっていてもよく、Ｒ¹³が複数ある場合、それらは互いに同じでも異なっていてもよい。］
［２］ 式（Ｉ）で表される化合物として、式（Ｉａ）で表される化合物、式（Ｉｂ）で表される化合物及び式（Ｉｃ）で表される化合物からなる群から選ばれる少なくとも２種の化合物を、少なくとも
（ｉ）式（Ｉａ）で表される化合物と式（Ｉｂ）で表される化合物となる組み合わせ、
（ｉｉ）式（Ｉａ）で表される化合物と式（Ｉｃ）で表される化合物となる組み合わせ又は
（ｉｉｉ）式（Ｉｂ）で表される化合物と式（Ｉｃ）で表される化合物となる組み合わせで含むことを特徴とする［１］に記載の着色剤。

［式（Ｉａ）、式（Ｉｂ）及び式（Ｉｃ）中、
Ｒ^1a、Ｒ^2a、Ｒ^1b及びＲ^1cは、互いに独立に、置換基を有してもよい炭素数１〜３０の炭化水素基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。ただし、Ｒ^1aとＲ^2aとが同じになることはなく、Ｒ^1bとＲ^1cとが同じになることはない。
Ｒ³〜Ｒ¹⁰は、前記と同じ意味を表す。］
［３］ 前記（ｉ）式（Ｉａ）で表される化合物と式（Ｉｂ）で表される化合物となる組み合わせ、及び前記（ｉｉ）式（Ｉａ）で表される化合物と式（Ｉｃ）で表される化合物となる組み合わせの少なくとも一方を満足し、
（ｉ）式（Ｉａ）で表される化合物と式（Ｉｂ）で表される化合物となる組み合わせを満足する場合、式（Ｉａ）のＲ^1aと式（Ｉｂ）のＲ^1bとが同じであり、
（ｉｉ）式（Ｉａ）で表される化合物と式（Ｉｃ）で表される化合物となる組み合わせを満足する場合、式（Ｉａ）のＲ^2aと式（Ｉｃ）のＲ^1cとが同じである［２］に記載の着色剤。
［４］ 式（Ｉａ）で表される化合物、式（Ｉｂ）で表される化合物及び式（Ｉｃ）で表される化合物を、それぞれ少なくとも１種以上含み、
式（Ｉａ）で表される化合物、式（Ｉｂ）で表される化合物及び式（Ｉｃ）で表される化合物の総量中、
前記式（Ｉａ）で表される化合物の含有率が３５モル％以上６５モル％以下であり、
前記式（Ｉｂ）で表される化合物の含有率が１５モル％以上３５モル％以下であり、
前記式（Ｉｃ）で表される化合物の含有率が１５モル％以上３５モル％以下である［２］又は［３］に記載の着色剤。
［５］ さらにペリレン化合物を含む［１］〜［４］のいずれかに記載の着色剤。
［６］ ［１］〜［５］のいずれかに記載の着色剤及び樹脂を含有する着色樹脂組成物。［７］ さらに重合性化合物及び重合開始剤を含有する［６］に記載の着色樹脂組成物。［８］ さらに溶剤を含有する［６］又は［７］に記載の着色樹脂組成物。
［９］ ［６］〜［８］のいずれかに記載の着色樹脂組成物から形成されるカラーフィルタ。
［１０］ ［９］に記載のカラーフィルタを含む表示装置。
［１１］ 式（Ｉａ）で表される化合物。

［式（Ｉａ）中、
Ｒ^1a及びＲ^2aは、互いに独立に、置換基を有してもよい炭素数１〜３０の炭化水素基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。ただし、Ｒ^1aとＲ^2aとが同じになることはない。
Ｒ³及びＲ⁸は、互いに独立に、置換基を有してもよい炭素数１〜３０の炭化水素基、置換基を有してもよい炭素数１〜３０の芳香族複素環基、又はこれらを組み合わせた基を表し、該炭化水素基に含まれる−ＣＨ₂−及び該組み合わせた基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。
Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁹及びＲ¹⁰は、互いに独立に、水素原子、−Ｒ¹¹、ハロゲン原子、ヒドロキシ基、カルボキシ基又はニトロ基を表す。
Ｒ⁴とＲ⁵、Ｒ⁵とＲ⁶及びＲ⁶とＲ⁷は、互いに結合して、−Ｒ¹²−ＣＯ−Ｏ−ＣＯ−Ｒ¹³−又は−Ｒ¹²−ＣＯ−Ｎ（Ｒ¹¹）−ＣＯ−Ｒ¹³−で表される基を形成してもよい。
Ｒ¹¹は、置換基を有してもよい炭素数１〜３０の炭化水素基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。Ｒ¹¹が複数ある場合、それらは互いに同じでも異なっていてもよい。
Ｒ¹²及びＲ¹³は、互いに独立に、単結合又は置換基を有してもよい炭素数１〜１５の２価の炭化水素基を表し、該２価の炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。Ｒ¹²が複数ある場合、それらは互いに同じでも異なっていてもよく、Ｒ¹³が複数ある場合、それらは互いに同じでも異なっていてもよい。］ The gist of the present invention is as follows.
[1] Containing at least two compounds represented by the formula (I),
The compounds represented by the two types of formulas (I) ^{are colorants in which at least R 1 of the} formula (I) is different from each other.

[In formula (I),
R ¹ and R ² represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent independently of each other, and −CH ₂ − contained in the hydrocarbon group is −O−, −CO. It may be replaced with −, −OCO− or −COO−.
R ³ and R ⁸ are independent of each other, a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent, or an aromatic heterocyclic group. Representing a group in which these are combined, -CH _2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -OCO- or -COO-.
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁹ and R ¹⁰ independently represent a hydrogen atom, −R ¹¹ , halogen atom, hydroxy group, carboxy group or nitro group.
R ⁴ and R ^5, R ⁵ and R ^6, and R ⁶ and R ⁷ are bonded to each ^{other, -R 12 -CO-O-CO} -R 13 - or ^{-R 12 -CO-N (R 11} ) - A group represented by CO-R ^{13-may be formed.}
R ¹¹ represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and −CH ₂ − contained in the hydrocarbon group is −O−, −CO−, −OCO− or −. It may be replaced with COO-. If there are a plurality of R ¹¹ s, they may be the same or different from each other.
R ¹² and R ¹³ represent divalent hydrocarbon groups having 1 to 15 carbon atoms which may have a single bond or a substituent independently of each other, and are contained in the divalent hydrocarbon group -CH _2. -May be replaced by -O-, -CO-, -OCO- or -COO-. If there are multiple R ¹² , they may be the same or different from each other, and if there ^{are multiple R 13} , they may be the same or different from each other. ]
[2] As the compound represented by the formula (I), at least selected from the group consisting of the compound represented by the formula (Ia), the compound represented by the formula (Ib) and the compound represented by the formula (Ic). A combination of two compounds, at least a compound represented by the formula (Ia) and a compound represented by the formula (Ib).
(Ii) A combination of a compound represented by the formula (Ia) and a compound represented by the formula (Ic) or a compound represented by the formula (Iii) formula (Ib) and a compound represented by the formula (Ic). The colorant according to [1], which is contained in combination.

[In formula (Ia), formula (Ib) and formula (Ic),
R ^1a , R ^2a , R ^1b and R ^1c represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent independently of each other, and −CH ₂ − contained in the hydrocarbon group is It may be replaced with −O−, −CO−, −OCO− or −COO−. However, R ^1a and R ^2a are never the same, and R ^{1 b and R 1 c} are never the same.
R ^{3 to} R ¹⁰ have the same meanings as described above. ]
[3] The combination of the compound represented by the formula (i) (Ia) and the compound represented by the formula (Ib), and the compound represented by the formula (Ia) and the formula (Ic). Satisfy at least one of the combinations that result in the compounds represented,
(I) When the combination of the compound represented by the formula (Ia) and the compound represented by the formula (Ib) is satisfied, R ^{1a of the formula (Ia) and R 1 b of the} formula (Ib) are the same. ,
(Ii) When the combination of the compound represented by the formula (Ia) and the compound represented by the formula (Ic) is satisfied, R ^2a of the formula (Ia) and R ^{1c of the} formula (Ic) are the same. The colorant according to [2].
[4] A compound represented by the formula (Ia), a compound represented by the formula (Ib), and a compound represented by the formula (Ic) are each contained at least one kind.
In the total amount of the compound represented by the formula (Ia), the compound represented by the formula (Ib) and the compound represented by the formula (Ic),
The content of the compound represented by the formula (Ia) is 35 mol% or more and 65 mol% or less.
The content of the compound represented by the formula (Ib) is 15 mol% or more and 35 mol% or less.
The colorant according to [2] or [3], wherein the content of the compound represented by the formula (Ic) is 15 mol% or more and 35 mol% or less.
[5] The colorant according to any one of [1] to [4], which further contains a perylene compound.
[6] A colored resin composition containing the colorant and resin according to any one of [1] to [5]. [7] The colored resin composition according to [6], which further contains a polymerizable compound and a polymerization initiator. [8] The colored resin composition according to [6] or [7], which further contains a solvent.
[9] A color filter formed from the colored resin composition according to any one of [6] to [8].
[10] A display device including the color filter according to [9].
[11] A compound represented by the formula (Ia).

[In formula (Ia),
R ^1a and R ^2a represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent independently of each other, and −CH ₂ − contained in the hydrocarbon group is −O−, −CO. It may be replaced with −, −OCO− or −COO−. However, R ^1a and R ^2a cannot be the same.
R ³ and R ⁸ are independent of each other, a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent, or an aromatic heterocyclic group. It represents a group comprising a combination thereof, -CH ₂ - contained in the hydrocarbon group is, -O - - -CH ₂ contained in and groups that combine the, - CO -, - OCO- or -COO- in replacing May be.
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁹ and R ¹⁰ independently represent a hydrogen atom, −R ¹¹ , halogen atom, hydroxy group, carboxy group or nitro group.
R ⁴ and R ^5, R ⁵ and R ^6, and R ⁶ and R ⁷ are bonded to each ^{other, -R 12 -CO-O-CO} -R 13 - or ^{-R 12 -CO-N (R 11} ) - A group represented by CO-R ^{13-may be formed.}
R ¹¹ represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and −CH ₂ − contained in the hydrocarbon group is −O−, −CO−, −OCO− or −. It may be replaced with COO-. If there are a plurality of R ¹¹ s, they may be the same or different from each other.
R ¹² and R ¹³ represent divalent hydrocarbon groups having 1 to 15 carbon atoms which may have a single bond or a substituent independently of each other, and are contained in the divalent hydrocarbon group -CH _2. -May be replaced by -O-, -CO-, -OCO- or -COO-. If there are multiple R ¹² , they may be the same or different from each other, and if there ^{are multiple R 13} , they may be the same or different from each other. ]

According to the present invention, there is provided a colored resin composition, a colorant and a compound that can be used for forming a color filter having more excellent light resistance as compared with a conventional colored resin composition containing a perylene compound as a colorant. NS.

The colorant of the present invention (hereinafter, may be referred to as a colorant (A)) contains at least two types of a compound represented by the formula (I) (hereinafter, may be referred to as a compound (I)), and the above two types are included. Compound (I) is a compound having at least R ^{1 of the} formula (I) different from each other.

［式（Ｉ）中、
Ｒ¹及びＲ²は、互いに独立に、置換基（Ａ１）を有してもよい炭素数１〜３０の炭化水素基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。
Ｒ³及びＲ⁸は、互いに独立に、置換基（Ａ１）を有してもよい炭素数１〜３０の炭化水素基、置換基（Ａ１）を有してもよい炭素数１〜３０の芳香族複素環基、又はこれらを組み合わせた基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。
Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁹及びＲ¹⁰は、互いに独立に、水素原子、−Ｒ¹¹、ハロゲン原子、ヒドロキシ基、カルボキシ基又はニトロ基を表す。
Ｒ⁴とＲ⁵、Ｒ⁵とＲ⁶及びＲ⁶とＲ⁷は、互いに結合して、−Ｒ¹²−ＣＯ−Ｏ−ＣＯ−Ｒ¹³−又は−Ｒ¹²−ＣＯ−Ｎ（Ｒ¹¹）−ＣＯ−Ｒ¹³−で表される基を形成してもよい。
Ｒ¹¹は、置換基（Ａ１）を有してもよい炭素数１〜３０の炭化水素基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。Ｒ¹¹が複数ある場合、それらは互いに同じでも異なっていてもよい。
Ｒ¹²及びＲ¹³は、互いに独立に、単結合又は置換基（Ａ１）を有してもよい炭素数１〜１５の２価の炭化水素基を表し、該２価の炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。Ｒ¹²が複数ある場合、それらは互いに同じでも異なっていてもよく、Ｒ¹³が複数ある場合、それらは互いに同じでも異なっていてもよい。］ <Compound (I)>

[In formula (I),
R ¹ and R ² represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1) independently of each other, and −CH ₂ − contained in the hydrocarbon group is −O−. , -CO-, -OCO- or -COO- may be replaced.
R ³ and R ⁸ are independent of each other, a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1), and an aromatic having 1 to 30 carbon atoms which may have a substituent (A1). It represents a group heterocyclic group or a group in which these are combined, and −CH ₂ − contained in the hydrocarbon group may be replaced with −O −, −CO−, −OCO− or −COO−.
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁹ and R ¹⁰ independently represent a hydrogen atom, −R ¹¹ , halogen atom, hydroxy group, carboxy group or nitro group.
R ⁴ and R ^5, R ⁵ and R ^6, and R ⁶ and R ⁷ are bonded to each ^{other, -R 12 -CO-O-CO} -R 13 - or ^{-R 12 -CO-N (R 11} ) - A group represented by CO-R ^{13-may be formed.}
R ¹¹ represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1), and −CH ₂ − contained in the hydrocarbon group is −O−, −CO−, −OCO. -Or -COO- may be replaced. If there are a plurality of R ¹¹ s, they may be the same or different from each other.
R ¹² and R ¹³ represent divalent hydrocarbon groups having 1 to 15 carbon atoms which may have a single bond or a substituent (A1) independently of each other, and are contained in the divalent hydrocarbon group. −CH ₂₋ may be replaced with −O−, −CO−, −OCO− or −COO−. If there are multiple R ¹² , they may be the same or different from each other, and if there ^{are multiple R 13} , they may be the same or different from each other. ]

Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ¹ , R ² , R ³ , R ⁸ and R ^{11 include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.} Aliphatic hydrocarbon groups may be saturated or unsaturated, and may be chain or alicyclic.

Saturated or unsaturated chain hydrocarbon groups represented by R ¹ , R ² , R ³ , R ⁸ and R ¹¹ include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group and heptyl group. , Octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecil group, icosyl group and other linear alkyl groups; isopropyl group, (1-Ethyl) propyl group, isobutyl group, sec-butyl group, tert-butyl group, (3-methyl) butyl group, (1-ethyl) butyl group, (2-ethyl) butyl group, (1-propyl) Butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl) pentyl group, (3-methyl) pentyl group, (1-ethyl) pentyl group, (2-ethyl) pentyl group, (3-ethyl) ) Pentyl group, (1-propyl) pentyl group, (1-butyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (1-ethyl) hexyl group, (2-ethyl) hexyl group, (1-ethyl) hexyl group Branched chains such as butyl) hexyl group, (1-pentyl) hexyl group, (3-ethyl) heptyl group, (1-hexyl) heptyl group, (1-heptyl) octyl group, (1-octyl) nonyl group, etc. Alkyl group; vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl) ethenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, Examples thereof include (1- (2-propenyl)) ethenyl groups, (1,2-dimethyl) propenyl groups, alkenyl groups such as 2-pentenyl groups; and the like. The number of carbon atoms of the saturated chain hydrocarbon group is preferably 1 to 25, more preferably 1 to 20, and even more preferably 1 to 15. The unsaturated chain hydrocarbon group preferably has 2 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, and even more preferably 2 to 15 carbon atoms.

Saturated or unsaturated alicyclic hydrocarbon groups represented by R ¹ , R ² , R ³ , R ⁸ and R ¹¹ include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl. Cycloalkyl groups such as groups; cycloalkenyl groups such as cyclohexenyl groups (eg, cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl groups, cyclooctenyl groups; norbornyl groups, adamantyl groups, bicyclos [2.2.2] Examples include octyl groups. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 25, more preferably 3 to 20, and even more preferably 3 to 15.

Examples of the aromatic hydrocarbon group represented by R ¹ , R ² , R ³ , R ⁸ and R ¹¹ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group and the like. Be done. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 25, more preferably 6 to 20, and even more preferably 6 to 15.

The ^{hydrocarbon groups represented by R 1} , R ² , R ³ , R ⁸ and R ¹¹ are the above-mentioned chain hydrocarbon groups and alicyclic hydrocarbon groups as long as the upper limit of the number of carbon atoms is 30 or less. , And a group in which two or more aromatic hydrocarbon groups are combined. Such a group may be, for example, a group in which an aromatic hydrocarbon group is combined with at least one of a group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group. In the hydrocarbon group by the combination, the chain hydrocarbon group may be combined as a divalent group (for example, an alcandiyl group). Examples of combined hydrocarbon groups include aralkyl groups such as benzyl group, phenethyl group, 1-methyl-1-phenylethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group; phenylethenyl group (phenylvinyl group). ) And other arylalkenyl groups; arylalkynyl groups such as phenylethynyl groups; o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2 , 3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4 , 6-trimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2,3-diisopropylphenyl group, 2,4-diisopropylphenyl group, 2,5 -Diisopropylphenyl group, 2,6-diisopropylphenyl group, 3,5-diisopropylphenyl group, 2,4,6-triisopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert- Butylphenyl group, p-tert-butylphenyl group, 2,6-di (tert-butyl) phenyl group, 3,5-di (tert-butyl) phenyl group, 3,6-di (tert-butyl) phenyl group , 4-tert-butyl-2,6-dimethylphenyl group, 4-pentylphenyl group, 4-octylphenyl group, 4- (2,4,4-trimethyl-2-pentyl) phenyl group, 2-dodecylphenyl group , 3-dodecylphenyl group, 4-dodecylphenyl group and other alkylaryl groups; 2,3-dihydro-4-indenyl group, 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 8-Methyl-1,2,3,5,6,7-Hexahydro-4-s-Indacenyl group, 5,6,7,8-Tetrahydro-1-naphthyl group, 5,6,7,8-Tetrahydro- 2-naphthyl group, 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group An aryl group to which an alcandiyl group such as, etc. is bonded; an aryl group to which one or more aryl groups such as a biphenylyl group and a terphenylyl group are bonded; a cyclohexylmethylphenyl group, a benzylphenyl group, a (dimethyl (phenyl) methyl) phenyl group, etc. Can be mentioned. Further, the above-mentioned hydrocarbon group may be, for example, a hydrocarbon group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include a 1-methylcyclopropyl group and a 2-methylcyclopentyl group. 1-Methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2, 3-Dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2- Dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group, 3,3,5,5 -Alicyclic hydrocarbon group to which one or more alkyl groups such as tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group are bonded; cyclopropylmethyl group, cyclopropylethyl group, One or more alicyclic hydrocarbon groups such as cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, and adamantylmethyl group were bonded. An alkyl group and the like can be mentioned. The carbon number of the group in which two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups are combined is preferably 4 to 28, more preferably 5 to 25, and even more preferably 6 to 20. ..

When _{-CH 2} − contained in the hydrocarbon group represented by ^{R 1} , R ² , R ³ , R ⁸ and R ¹¹ is replaced with −O −, −CO−, −OCO− or −COO− The number may be one or two or more. _{When −CH 2} − contained in the hydrocarbon group is replaced with −O−, −CO−, −OCO− or −COO−, the number of carbon atoms before the replacement is defined as the number of carbon atoms of the hydrocarbon group. As a _{group in which −CH 2} − contained in the hydrocarbon groups represented by ^{R 1} , R ² , R ³ , R ⁸ and R ¹¹ is replaced with −O −, −CO−, −OCO− or −COO−. Specifically, the groups represented by the following formulas (Y-1) to (Y-25) can be mentioned. * Represents a bond.

The divalent hydrocarbon groups having 1 to 15 carbon atoms represented by ^{R 12} and R ^{13 include the hydrocarbon groups represented by R 1} , R ² , R ³ , R ⁸ and R ¹¹ (however, the number of carbon atoms). Does not include examples where is 16 or more)
Examples thereof include a group having one hydrogen atom contained in the bond as a bond. The number of carbon atoms of the divalent hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 5. Further, as the divalent hydrocarbon group, a divalent saturated chain hydrocarbon group is preferable, and a linear or branched alkanediyl group is more preferable. Examples of the divalent hydrocarbon group include an alkanediyl group such as a methylene group, an ethylene group, a propylene group and a butylene group.

When _{-CH 2-} contained in the divalent hydrocarbon group represented by ^{R 12} and R ¹³ is replaced with -O-, -CO-, -OCO- or -COO-, the number may be one. There may be two or more. _{When −CH 2} − contained in the hydrocarbon group is replaced with −O−, −CO−, −OCO− or −COO−, the number of carbon atoms before the replacement is taken as the number of carbon atoms of the divalent hydrocarbon group. do. _{Specifically, as a group in which −CH 2} − contained in the divalent hydrocarbon group represented by R ¹² and R ¹³ is replaced with −O−, −CO−, −OCO− or −COO−, specifically. Examples thereof include a group having one hydrogen atom contained in the groups represented by the above formulas (Y-1) to (Y-25) as a bond.

Examples of the aromatic heterocyclic group having 1 to 30 carbon atoms represented by R ³ and R ⁸ include an aromatic heterocyclic group containing at least one hetero atom such as a nitrogen atom, an oxygen atom, and a sulfur atom. Specific examples of the aromatic heterocyclic group include a frill group, a pyrrolyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a thiazolyl group, a benzothiazolyl group and a carbazolyl group. The number of carbon atoms of the aromatic heterocyclic group is preferably 2 to 25, more preferably 3 to 20, and even more preferably 3 to 15.

As ^{the combined group formed by bonding the hydrocarbon group represented by R 3} and R ⁸ and the aromatic heterocyclic group, the above-mentioned hydrocarbon group and aromatic heterocyclic group are two. The group may be bonded as described above, and is, for example, a group in which at least one selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group is bonded to an aromatic heterocyclic group. In the group formed by the bond, the chain hydrocarbon group may be bonded as a divalent group (for example, an alcandiyl group). Examples of groups formed by bonding the hydrocarbon group and the aromatic heterocyclic group include 2-methylpyridinyl group, 4-ethyl-2-methylpyridinyl group, indole group, benzimidazole group, benzofuran group, and benzothiophene. The group and the like can be mentioned. The carbon number of the group combining the hydrocarbon group and the aromatic heterocyclic group is preferably 4 to 30, more preferably 6 to 30, and even more preferably 10 to 30.

A hydrocarbon group having 1 to 30 carbon atoms represented by R ¹ , R ² , R ³ , R ⁸ and R ¹¹ , an aromatic heterocyclic group having 1 to 30 carbon atoms represented by ^{R 3} and R ^{8, and an aromatic heterocyclic group having 1 to 30 carbon atoms.} Examples of the substituent (A1) that the divalent hydrocarbon group having 1 to 15 carbon atoms represented by R ¹² and R ^{13 may have include a halogen atom; a nitrile group; a nitro group; an amino group;} Hydroxyl group; thiol group; alkylthio group having 1 to 20 carbon atoms such as methylthio group and ethylthio group; allylthio group; arylthio group having 6 to 20 carbon atoms such as phenylthio group, 1-naphthylthio group and 2-naphthylthio group; sulfoxy group Alkyl sulfoxy groups having 1 to 20 carbon atoms such as methyl sulfoxy groups and ethyl sulfoxy groups; aryls having 6 to 20 carbon atoms such as phenyl sulfoxy groups, 1-naphthyl sulfoxy groups and 2-naphthyl sulfoxy groups Sulfoxy group; silyl group; boryl group; monomethylamino group, dimethylamino group, trimethylamino group, monoethylamino group, diethylamino group, triethylamino group and other alkylamino groups having 1 to 20 carbon atoms; monophenylamino group, Examples thereof include an arylamino group having 6 to 20 carbon atoms such as a diphenylamino group and a triphenylamino group; an aralkylamino group having 7 to 20 carbon atoms such as a benzylamino group; a carboxy group; a carbamoyl group and the like.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. From the viewpoint of synthesis, chlorine atom and bromine atom are preferable.

Specific examples of the hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1) represented by R ¹ , R ² , R ³ , R ⁸ and R ^{11 include the following formula (D).} -1) to the groups represented by the formulas (D-37) and the formulas (G-1) to the formulas (G-24) can be mentioned. * Represents a bond.

From the viewpoint of improving the light resistance of the obtained color filter, R ¹ and R ² have a saturated chain hydrocarbon group and a substituent (A1) which may have a substituent (A1) independently of each other. A group in which an aromatic hydrocarbon group and a chain hydrocarbon group may be combined, or a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group which may have a substituent (A1) are combined. It is preferable that −CH ₂ − contained in the hydrocarbon group is not replaced with −O −, −CO−, −OCO− or −COO− in any of the groups. R ¹ and R ² are independent of each other, a saturated chain hydrocarbon group having 1 to 15 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, and a chain hydrocarbon group having 1 to 10 carbon atoms. It is more preferable that the group is a combination of the above, or a chain hydrocarbon group having 1 to 10 carbon atoms and an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and is saturated with 3 to 13 carbon atoms. A chain hydrocarbon group, a group combining an aromatic hydrocarbon group having 6 to 10 carbon atoms and a chain hydrocarbon group having 1 to 5 carbon atoms, or a chain hydrocarbon group having 1 to 5 carbon atoms. It is more preferable that the group is a combination of an alicyclic hydrocarbon group having 5 to 10 carbon atoms. Specifically, R ¹ and R ² are preferably groups represented by any of the above formulas (D-1) to (D-37) independently of each other, and are preferably formulas (D-3). )-Formula (D-10) or a group represented by any of the formulas (D-12)-formula (D-37), more preferably formulas (D-4)-formulas (D-9). ), Or a group represented by any of the formulas (D-22) to (D-37), more preferably the formulas (D-5) to (D-8), formula (D-28). ) ~ Formula (D-33) or formula (D-36) is more preferable.
From the viewpoint of improving the solubility of compound (I) in a solvent, R ¹ and R ² are preferably saturated chain hydrocarbon groups having 1 to 15 carbon atoms independently of each other, and have 3 carbon atoms. It is more preferably a saturated chain hydrocarbon group of ~ 13, and even more preferably a linear alkyl group having 3 to 13 carbon atoms.
R ¹ and R ² may be the same or different, but are preferably different.

From the viewpoint of improving the light resistance of the obtained color filter, R ³ and R ⁸ have an aromatic hydrocarbon group or a substituent (A1) which may have a substituent (A1) independently of each other. It is preferable that the group is a combination of an aromatic hydrocarbon group and a chain hydrocarbon group, and a combination of an aromatic hydrocarbon group and a chain hydrocarbon group which may have a substituent (A1) is preferable. It is more preferable that the group is a combination of an aromatic hydrocarbon group and a chain hydrocarbon group, and more preferably a group in which an aromatic hydrocarbon group and a saturated chain hydrocarbon group are combined. It is even more preferable that the group is a combination of an aromatic hydrocarbon group having 6 to 12 carbon atoms and a saturated chain hydrocarbon group having 1 to 8 carbon atoms, and the two ortho positions of the phenyl group are more preferable. It is particularly preferable that the group has a saturated chain hydrocarbon group bonded thereto. Specifically, R ³ and R ⁸ are preferably groups represented by any of the above formulas (G-1) to (G-24) independently of each other, and are preferably formulas (G-1). ) To a group represented by any of the formulas (G-15), and further preferably a group represented by any of the formulas (G-5) to (G-15). , Formula (G-5) to formula (G-9), formula (G-12) or formula (G-14), more preferably, formula (G-8). It is particularly preferable that the group is represented by.
Further, R ³ and R ⁸ may be the same or different, but are preferably the same.

Examples of the halogen atom represented by R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁹ and R ¹⁰ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

R ⁴ and R ^5, R ⁵ and R ^6, and R ⁶ and R ⁷ are bonded to each other to ^{form, -R 12 -CO-O-CO} -R 13 - Examples of the group represented by, specifically, , Divalent groups represented by the following formulas (H-1) to (H-8) can be mentioned. * Represents a bond with the benzoperylene skeleton of ^{R 4} and R ⁵ , R ⁵ and R ^6, or R ⁶ and R ^7.

R ⁴ and R ^5, R ⁵ and R ^6, and R ⁶ and R ⁷ are bonded to each other to ^{form, -R 12 -CO-N (R} 11) -CO-R 13 - Examples of the group represented by, Specific examples thereof include divalent groups represented by the following formulas (H-9) to (H-16). * Represents a bond with the benzoperylene skeleton of ^{R 4} and R ⁵ , R ⁵ and R ^6, or R ⁶ and R ^7.

More specifically, examples of the group represented by the formula (H-9) include groups represented by the following formulas (H-9-1) to (H-9-16). * Represents a bond with the benzoperylene skeleton of ^{R 4} and R ⁵ , R ⁵ and R ^6, or R ⁶ and R ^7.

R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁹ and R ¹⁰ are preferably hydrogen atoms. R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁹ and R ¹⁰ may be appropriately combined to form a compound having a desired absorption wavelength or fluorescence wavelength.

Specific examples of the compound (I) include the compounds shown in Table 1 below.

In Table 1, H represents a hydrogen atom, D-5, D-6, D-7, D-8, D-29, D-30, D-31, D-33, D-36, G-8. Are the above formulas (D-5), formulas (D-6), formulas (D-7), formulas (D-8), formulas (D-29), formulas (D-30), and formulas (D), respectively. It means a group represented by −31), the formula (D-33), the formula (D-36), and the formula (G-8).

From the viewpoint of improving the light resistance of the obtained color filter, the compound (I) is preferably compound (I-1) to compound (I-45), and compound (I-2) to compound (I-9), compound. (I-11) to compound (I-17), compound (I-19) to compound (I-24), compound (I-26) to compound (I-30), compound (I-32) to compound ( I-35), compound (I-37) to compound (I-39), compound (I-41), compound (I-42) or compound (I-44) are more preferred.

<Colorant (A)>
The colorant (A) contains at least two compounds (I), and each of the two compounds (I) is a compound having at least R ^{1 of the} formula (I) different from each other. ^{R 2} of the formula (I) of the two compounds (I) may be the same as or different from each other. ^{Further, R 3 to} R ¹⁰ of the formula (I) of the two compounds (I) may be independently the same or different from each other, and 4 to 8 of ^{R 3 to} R ^{10 are mutually exclusive.} preferably the same, more preferably is one 6-8 is identical to each other among the R ³ to R ^10, it is preferable that all of R ³ to R ¹⁰ are the same to each other. The compound (I) contained as the colorant (A) is preferably 2 or more and 6 or less, more preferably 2 or more and 5 or less, and further preferably 2 or more and 4 or less. preferable.

The two or more compounds (I) contained as the colorant (A) are represented by the following formula (Ia) (hereinafter, may be referred to as compound (Ia)) and the following formula (Ib). At least two compounds selected from the group consisting of a compound (hereinafter, may be referred to as compound (Ib)) and a compound represented by the following formula (Ic) (hereinafter, may be referred to as compound (Ic)). At least a combination of a compound represented by the formula (Ia) and a compound represented by the formula (Ib) (hereinafter, may be referred to as a combination of (i)).
(Ii) A combination of a compound represented by the formula (Ia) and a compound represented by the formula (Ic) (hereinafter, may be referred to as a combination of (ii)) or represented by the formula (Iii) (Ib). It is preferably contained in a combination of the compound and the compound represented by the formula (Ic) (hereinafter, may be referred to as a combination of (iii)).

［式（Ｉａ）、式（Ｉｂ）及び式（Ｉｃ）中、
Ｒ^1a、Ｒ^2a、Ｒ^1b及びＲ^1cは、互いに独立に、置換基（Ａ５）を有してもよい炭素数１〜３０の炭化水素基を表し、該炭化水素基に含まれる−ＣＨ₂−は、−Ｏ−、−ＣＯ−、−ＯＣＯ−又は−ＣＯＯ−に置き換わっていてもよい。ただし、Ｒ^1aとＲ^2aとが同じになることはなく、Ｒ^1bとＲ^1cとが同じになることはない。
Ｒ³〜Ｒ¹⁰は、前記と同じ意味を表す。］ << Compound (Ia), Compound (Ib), Compound (Ic) >>

[In formula (Ia), formula (Ib) and formula (Ic),
R ^1a , R ^2a , R ^1b and R ^1c represent hydrocarbon groups having 1 to 30 carbon atoms which may have a substituent (A5) independently of each other, and are contained in the hydrocarbon group −CH ₂ -May be replaced by -O-, -CO-, -OCO- or -COO-. However, R ^1a and R ^2a are never the same, and R ^{1 b and R 1 c} are never the same.
R ^{3 to} R ¹⁰ have the same meanings as described above. ]

^{The two R 1b} in the formula (Ib) are the same group, and the two R ^1c in the formula (Ic) are the same group.

The hydrocarbon groups having 1 to 30 carbon atoms represented by R ^1a , R ^2a , R ^1b and R ^1c are the same as the hydrocarbon groups represented by ^{R 1} , R ² , R ³ , R ⁸ and R ^11. Examples are given, and so is the preferred range of carbon numbers.

When _{−CH 2} − contained in the hydrocarbon groups represented by ^{R 1a} , R ^2a , R ^1b and R ^1c is replaced with −O−, −CO−, −OCO− or −COO−, the number is 1. It may be one, or two or more. _{When −CH 2} − contained in the hydrocarbon group is replaced with −O−, −CO−, −OCO− or −COO−, the number of carbon atoms before the replacement is defined as the number of carbon atoms of the hydrocarbon group. The _{group in which −CH 2} − contained in the hydrocarbon groups represented by ^{R 1a} , R ^2a , R ^1b and R ^1c is replaced with −O−, −CO−, −OCO− or −COO− is R. _{-CH 2-} contained in the hydrocarbon groups represented by ¹ , R ² , R ³ , R ⁸ and R ¹¹ is the same as the group in which -O-, -CO-, -OCO- or -COO- is replaced. For example.

Substituents (A5) that the hydrocarbon groups having 1 to 30 carbon atoms represented by R ^1a , R ^2a , R ^1b and R ^{1c may have include R 1} , R ² , R ³ , and R ^8. And the same example as the substituent (A1) which the hydrocarbon group having 1 to 30 carbon atoms represented by R ^{11 may have.}

From the viewpoint of improving the light resistance of the obtained color filter, R ^1a , R ^2a , R ^1b and R ^1c are saturated chain hydrocarbon groups and substituents which may have a substituent (A5) independently of each other. A group combining an aromatic hydrocarbon group and a chain hydrocarbon group which may have (A5), or a chain hydrocarbon group and an alicyclic hydrocarbon group which may have a substituent (A5). It is preferable that the group is a combination of the above, and it is preferable that −CH ₂ − contained in the hydrocarbon group is not replaced with −O−, −CO−, −OCO− or −COO− in any of the groups. .. R ^1a , R ^2a , R ^1b and R ^1c are independent of each other, a saturated chain hydrocarbon group having 1 to 15 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms and 1 to 10 carbon atoms. It is more preferable that the group is a combination of a chain hydrocarbon group of 1 to 10 or a combination of a chain hydrocarbon group having 1 to 10 carbon atoms and an alicyclic hydrocarbon group having 3 to 12 carbon atoms. Saturated chain hydrocarbon groups of number 3 to 13, a group combining an aromatic hydrocarbon group of 6 to 10 carbon atoms and a chain hydrocarbon group of 1 to 5 carbon atoms, or a group of 1 to 5 carbon atoms. It is more preferable that the group is a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group having 5 to 10 carbon atoms. From the viewpoint of improving the solubility of compound (I) in a solvent, R ^1a , R ^2a , R ^1b and R ^1c may be saturated chain hydrocarbon groups having 1 to 15 carbon atoms independently of each other. It is more preferably a saturated chain hydrocarbon group having 3 to 13 carbon atoms, and even more preferably a linear alkyl group having 3 to 13 carbon atoms. Specifically, R ^1a , R ^2a , R ^1b and R ^1c are preferably groups represented by any of the above formulas (D-1) to (D-37) independently of each other. , Formula (D-3) to formula (D-10), or formula (D-12) to formula (D-37), more preferably, formula (D-4). It is more preferable that the group is represented by any of the formulas (D-9) or (D-22) to (D-37), and formulas (D-5) to (D-8). , The group represented by any of the formulas (D-28) to (D-33) or (D-36) is more preferable.

^{The distinction between R 1a} and R ^2a in the formula (Ia) is determined by the following discriminant criteria.
Write the number of -CH ₃ often; third priority determination criterion to whichever is R ^1a large number of - -CH _2; the second priority determination criterion to the expression amount is larger the R ^1a; first priority determination criterion for example, the R ^1a, when the compound (I-2), an R ^2a of formula (D-5) pentyl group is a group represented by formula (Ia), formula (D-6) It is assumed that the hexyl group represented is R ^{1a of the formula (Ia).}

^{The distinction between R 1b} and R ^{1c in} the formula (Ib) and the formula (Ic) is determined by the following discriminant criteria.
Write the number of -CH ₃ often; third priority determination criterion to whichever is R ^1b a large number of - -CH _2; the second priority determination criterion to whichever is R ^1b formula weight is large; first priority determination criterion is referred to as R ^1b for example, when the compound (I-1) and compound (I-10), formula (D-5) pentyl group is a group represented by the formula of compound (I-1) (Ic ) and R ^1c (ie compound (I-1) corresponds to the compound (Ic)), compound (I-10) of formula (hexyl formula a group represented by D-6) (Ib) and which is the R ^1b (i.e. corresponding to compound (I-10) the compound (Ib)).

As the colorant (A), at least two compounds selected from the group consisting of compound (Ia), compound (Ib) and compound (Ic) are used in the combination of the above (i) and at least the combination of the above (ii). when including to satisfy one is preferably the a R ^1b of R ^1a and formula (Ib) of the formula (Ia) are the same may include to satisfy a combination of (i), (ii ) Satisfyingly, it is preferable that ^{R 2a} of the formula (Ia) and R ^{1c of the formula (Ic) are the same.}
For example, if the compound (Ia) is the compound (I-2) and the colorant (A) contains a combination of the compound (Ia) and the compound (Ib), the compound (Ib) The above compound (I-10) is preferable. Further, for example, when the compound (Ia) is the compound (I-2) and the colorant (A) contains a combination of the compound (Ia) and the compound (Ic), the compound (Ic) The above compound (I-1) is preferable.

When the colorant (A) contains at least two compounds selected from the group consisting of the compound (Ia), the compound (Ib) and the compound (Ic) so as to satisfy the combination of the above (i), the compound ( The content of compound (Ia) in the total amount of Ia) and compound (Ib) is preferably 45 mol% or more and 85 mol% or less, more preferably 50 mol% or more and 80 mol% or less, 55. It is more preferably mol% or more and 75 mol% or less.
When the colorant (A) contains at least two compounds selected from the group consisting of the compound (Ia), the compound (Ib) and the compound (Ic) so as to satisfy the combination of the above (ii), the compound ( The content of compound (Ia) in the total amount of Ia) and compound (Ic) is preferably 45 mol% or more and 85 mol% or less, more preferably 50 mol% or more and 80 mol% or less, 55. It is more preferably mol% or more and 75 mol% or less.
When the colorant (A) contains at least two compounds selected from the group consisting of the compound (Ia), the compound (Ib) and the compound (Ic) so as to satisfy the combination of the above (iii), the compound ( The content of compound (Ib) in the total amount of Ib) and compound (Ic) is preferably 35 mol% or more and 65 mol% or less, more preferably 40 mol% or more and 60 mol% or less, and 45. It is more preferably mol% or more and 55 mol% or less.

As the colorant (A), from the viewpoint of colorant comprising the formula R ¹ is different from each other at least two compounds of (I) (I) to (A) can be easily produced, the compound (Ia), Compound (Ib) and the compound (Ic), preferably each comprise at least one more, and the R ^1b are the same in formula (Ia) R ^1a and formula (Ib), and R ^2a and of formula (Ia) (Ic ), It is more preferable that the compound (Ia), the compound (Ib) and the compound (Ic) are each contained at least one kind so as to be the same ^{as R 1c.}
Further, as the colorant (A), from the viewpoint of easily controlling the content of each compound (I) in the colorant (A), the compound (Ia) is not contained, and the compound (Ib) and the compound (Ic) are used. It is preferable to contain at least one of each.

When one or more of the compound (Ia), the compound (Ib) and the compound (Ic) are contained as the colorant (A), the content of the compound (Ia) is the compound (Ia), the compound (Ib) and the compound (Ia). The total amount of Ic) is preferably 35 mol% or more and 65 mol% or less, more preferably 40 mol% or more and 60 mol% or less, and further preferably 45 mol% or more and 55 mol% or less.

When one or more of the compound (Ia), the compound (Ib) and the compound (Ic) are contained as the colorant (A), the contents of the compound (Ib) and the compound (Ic) are independently determined by the compound (Ia). ), Compound (Ib) and compound (Ic), preferably 15 mol% or more and 35 mol% or less, more preferably 18 mol% or more and 32 mol% or less, and 20 mol% or more and 30 mol. It is more preferably less than or equal to%.
When one or more of the compound (Ia), the compound (Ib) and the compound (Ic) are contained as the colorant (A), the content ratio of the compound (Ib) to the compound (Ic) (compound (Ib) / Compound (Ic)) is preferably 0.80 or more and 1.20 or less, more preferably 0.85 or more and 1.15 or less, and 0.87 or more and 1.13 or less on a molar basis. Is even more preferable.

As the compound (I), the compound (Ia) is particularly preferable.

As compound (I), for example, a compound represented by the following formula (pt1) is produced by reacting a compound represented by the following formula (pt1) with maleic anhydride in the presence of a dehydrogenating agent to produce a compound represented by the following formula (pt1-1). In the solvent, the compounds represented by the following formulas (MAT1-1), formulas (MA1-2), formulas (MA2-1) and formulas (MA2-2) are added to the compounds represented by the formula (pt1-1). It can be produced by reacting in the presence of a base. When R ¹ and R ² in the following formula are different, they are represented by the compound represented by the formula (I), the compound represented by the formula (I)', and the compound represented by the formula (I)''. It is also possible to produce the compounds at the same time. For example, when ^{the formula amount of R 1} is larger than the formula amount of R ² , the compound represented by the formula (I) corresponds to the above-mentioned compound (Ia), and the compound represented by the formula (I)' Corresponds to the above-mentioned compound (Ib), and the compound represented by the formula (I)'' corresponds to the compound (Ic).

［式中、Ｒ¹〜Ｒ¹⁰は、上述の定義と同一である。Ｘ¹及びＸ²は、互いに独立に、ハロゲン原子を表す。］

[In the formula, R ^{1 to} R ¹⁰ are the same as the above definitions. X ¹ and X ² represent halogen atoms independently of each other. ]

Examples of the compound represented by formula (pt1), for example, N ^1, N ² - bis (2,6-diisopropylphenyl) perylene-3,4,9,10-tetracarboxylic acid diimide, and the like.

The amount of maleic anhydride used is usually 1 mol or more and 1,000 mol or less, preferably 1 mol or more and 800 mol or less, and more preferably 1 mol or less, based on 1 mol of the compound represented by the formula (pt1). It is 1 mol or more and 600 mol or less, and more preferably 1 mol or more and 400 mol or less.

The dehydrogenator is one that dehydrogenates the hydrogen of the 6-membered ring compound to aromatize it. Dehydrogenators include p-chloranil, p-benzoquinone, 2,5-dichloro-p-quinone, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tetramethyl-p-quinone, 2 , 5-Diphenyl-p-quinone, bromanil are preferred, and p-chloranil, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone are more preferred.

The reaction temperature when reacting maleic anhydride with the compound represented by the formula (pt1) is usually −100 ° C. or higher and 300 ° C. or lower. The reaction time for reacting maleic anhydride with the compound represented by the formula (pt1) is usually 0.5 hour to 500 hours.

Examples of the halogen atom represented by X ¹ and X ² include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a bromine atom or an iodine atom is preferable.

Examples of the compound represented by the formula (MA1-1) and the formula (MA2-1) include 1-pentanol, 1-hexanol, 2-ethylhexanol, 1-heptanol, 1-octanol, benzyl alcohol and cyclohexanemethanol. And so on.

Examples of the compound represented by the formula (MA1-2) and the formula (MA2-2) include 1-bromopentane, 1-iodopentane, 1-bromohexane, 1-iodohexane, and 1-bromo-2-ethyl. Examples thereof include hexane, 1-iodo-2-ethylhexane, 1-bromoheptane, 1-iodoheptane, 1-bromooctane, 1-iodooctane, benzyl bromide, benzyl iodide, cyclohexylmethyl bromide, cyclohexyl methyl iodide and the like. ..

The amounts of the compounds represented by the formulas (MA1-1), formula (MA1-2), formula (MA2-1) and formula (MA2-2) are independently represented by the formula (pt1-1). It is usually 1 mol or more and 20 mol or less, preferably 1 mol or more and 10 mol or less, with respect to 1 mol of the compound. The total amount of the compound represented by the formula (MA1-1), the formula (MA1-2), the formula (MA2-1) and the formula (MA2-2) is the compound represented by the formula (pt1-1). With respect to 1 mol, it is usually 5 mol or more and 50 mol or less, preferably 10 mol or more and 35 mol or less.

As a base in the reaction between the compound represented by the formula (pt1-1) and the compound represented by the formulas (MA1-1), formula (MA1-2), formula (MA2-1) and formula (MA2-2). Is an organic substance such as triethylamine, 4- (N, N-dimethylamino) pyridine, pyridine, piperidine, 1,8-diazabicyclo [5.4.0] undecene, 1,5-diazabicyclo [4.3.0] nonene. Metal alkoxides such as base, sodium methoxydo, sodium ethoxydo, sodium tert-butoxide, potassium tert-butoxide, organic metal compounds such as methyllithium, butyllithium, tert-butyllithium and phenyllithium, sodium hydrogencarbonate, potassium hydrogencarbonate. , Inorganic bases such as sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and the like, and organic bases are preferable.

The amount of the base used is usually 0.1 mol or more and 100 mol or less, preferably 1 mol or more and 40 mol or less, with respect to 1 mol of the compound represented by the formula (pt1-1).

As a solvent in the reaction between the compound represented by the formula (pt1-1) and the compounds represented by the formulas (MA1-1), formula (MA1-2), formula (MA2-1) and formula (MA2-2). Water; nitrile solvents such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol , Alcohol solvents such as phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene Halogenized hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethylsulfoxide, acetic acid, propionic acid, butyric acid and the like. Examples thereof include a carboxylic acid solvent and imidazole, and an amide solvent is preferable, and N, N-dimethylformamide is more preferable.

The amount of the solvent used is usually 0.1 to 1000 parts by mass with respect to 1 part by mass of the compound represented by the formula (pt1-1).

When the compound represented by the formula (pt1-1) is reacted with the compound represented by the formulas (MA1-1), the formula (MA1-2), the formula (MA2-1) and the formula (MA2-2). The reaction temperature is usually −100 ° C. or higher and 300 ° C. or lower. Further, when reacting the compound represented by the formula (pt1-1) with the compound represented by the formulas (MA1-1), the formula (MA1-2), the formula (MA2-1) and the formula (MA2-2). The reaction time of is usually 0.5 hour to 500 hours.

After completion of the reaction, the method for taking out the compound (I) is not particularly limited, and the compound (I) can be taken out by various known methods. After taking out, the obtained residue may be purified by column chromatography, recrystallization or the like. The chemical structure of the obtained compound can be analyzed by a known analysis method and its conditions. Such an analysis method is not particularly limited, and examples thereof include an X-ray crystal structure analysis method, a mass spectrometry method (LC), an NMR analysis method, and an elemental analysis method. X-ray crystallography can be described, for example, in Chemistry of Materials, 2012, Vol. 24, p. It can be done in accordance with 4647-4652.

Compound (I), especially mixtures of the formula R ¹ is different compound of (I) (I) a compound containing two or more (I) are propylene glycol monomethyl ether acetate, a solvent (especially propylene glycol monomethyl ether acetate and cyclohexanone ) Has high solubility and good solubility. For the solubility, a compound or a mixture of compounds whose solubility is to be measured (hereinafter, may be referred to as a solute) is weighed in a 20 mL screw tube in an amount of about 50 mg, about 500 mg of a solvent is added thereto, and the total amount of the solute and the solvent is weighed. Then, after stirring with a mix rotor for 30 minutes, if dissolution is visually confirmed, it can be calculated from the following formula (h) from the mass of the solute with respect to the total mass of the solute and the solvent. If dissolution was not visually confirmed, continue to add 500 mg of solvent until it was dissolved, and each time it was added, stir with a mix rotor for 30 minutes. The solubility can be obtained from the mass by the following formula (h).
Solubility (%) = (mass of solute) / (total mass of solute and solvent) x 100 (h)

The solubility of compound (I) in propylene glycol monomethyl ether acetate at 20 ° C. is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, and 1.5% by mass. The above is more preferable, and it may be 15% by mass or less. When two or more kinds of compounds (I) are contained as a colorant, the solubility of the compound (I) to be contained in a mixture is preferably in the above range.

The content of the compound (I) may be 100% by mass or more, and the lower limit may be, for example, 0.1% by mass or more, preferably 5% by mass or more, based on the total amount of the colorant (A). 10% by mass or more is more preferable, 20% by mass or more is further preferable, 30% by mass or more is further preferable, and 50% by mass or more is further preferable.

The colorant (A) may further contain one or more perylene compounds. As the perylene compound, a compound in which a substituent having a carbonyl group is bonded at the 3,4 and 9,10 positions is preferable. The carbonyl group of the substituents at the 3 and 4 positions is preferably bonded via an oxygen atom to form a lactone ring, or bonded via a nitrogen atom to form an imide ring. The carbonyl group of the substituent at the 9th and 10th positions is also preferably bonded via an oxygen atom to form a lactone ring or bonded via a nitrogen atom to form an imide ring. Further, as the perylene compound, a compound in which a substituent having an oxy group is bonded to the 1, 6, 7 and 12 positions independently of each other is preferable. The perylene compound is preferably a red fluorescent dye. From the viewpoint of improving the solubility in a solvent, the perylene compound is particularly preferably a compound represented by the formula (II) (hereinafter, may be referred to as a compound (II)).

［式（ＩＩ）中、
Ａｒ²¹〜Ａｒ²⁶は、互いに独立に、置換基（Ａ３）を有してもよい炭素数６〜２０のアリール基を表す。
Ｒ²¹〜Ｒ²⁴は、互いに独立に、水素原子、置換基（Ａ４）を有してもよい炭素数１〜２０の炭化水素基、ハロゲン原子又はニトロ基を表す。] << Compound (II) >>

[In formula (II),
Ar ^{21 to} Ar ²⁶ represent an aryl group having 6 to 20 carbon atoms which may have a substituent (A3) independently of each other.
R ^{21 to} R ²⁴ represent a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom or a nitro group, which may have a hydrogen atom and a substituent (A4) independently of each other. ]

Examples of the aryl group represented by Ar ^{21 to Ar 26} include a phenyl group, a naphthyl group and the like independently of each other, and a phenyl group is preferable.

The ^{substituent (A3) that the aryl group represented by Ar 21 to} Ar ²⁶ may have is a halogen atom; a nitrile group; a nitro group; an amino group; an amide group; a sulfonamide group; a hydroxy group; a methyl group. , An alkyl group having 1 to 10 carbon atoms such as an ethyl group, an isopropyl group and a tert-butyl group; a cycloalkyl group having 1 to 20 carbon atoms such as a cyclopropyl group and a cyclobutyl group; a carbon such as a vinyl group and a 1-propenyl group. Alkenyl group of 2 to 10; aryl group having 6 to 10 carbon atoms such as phenyl group and 1-naphthyl group; aralkyl group having 7 to 10 carbon atoms such as benzyl group and phenethyl group; phenylethenyl group (phenylvinyl group) ) Etc., arylalkenyl groups having 8 to 10 carbon atoms; alkoxy groups having 1 to 10 carbon atoms such as methoxy group and ethoxy group; 6 to 10 carbon atoms such as phenyloxy group, 1-naphthyloxy group and 2-naphthyloxy group. 10 aryloxy groups; thiol groups; alkylthio groups having 1 to 10 carbon atoms such as methylthio groups and ethylthio groups; allylthio groups; arylthio groups having 6 to 10 carbon atoms such as phenylthio groups, 1-naphthylthio groups and 2-naphthylthio groups. Sulfoxy group; Alkyl sulfoxy group having 1 to 10 carbon atoms such as methyl sulfoxy group and ethyl sulfoxy group; 6 to 10 carbon atoms such as phenyl sulfoxy group, 1-naphthyl sulfoxy group and 2-naphthyl sulfoxy group. 10 aryl sulfoxy group; silyl group; boryl group; monomethylamino group, dimethylamino group, trimethylamino group, monoethylamino group, diethylamino group, triethylamino group and other alkylamino groups having 1 to 10 carbon atoms; monophenyl An arylamino group having 6 to 10 carbon atoms such as an amino group; an aralkylamino group having 7 to 10 carbon atoms such as a benzylamino group; an N-methylaminosulfonyl group, an N, N-dimethylaminosulfonyl group, and an N-ethylaminosulfonyl group. Alkylaminosulfonyl group with 1 to 10 carbon atoms, carboxy group; carbamoyl group; alkylcarbonyl group with 2 to 10 carbon atoms such as acetyl group and propionyl group; arylcarbonyl group with 7 to 10 carbon atoms such as benzoyl group An alkoxycarbonyl group having 2 to 10 carbon atoms such as a methoxycarbonyl group and an ethoxycarbonyl group; an aryloxycarbonyl group having 7 to 20 carbon atoms such as a phenyloxycarbonyl group; ~ 20 heterocyclic groups; chloromethyl group, dichloromethyl group, fluoromethyl group, trifluoromethyl group , An alkyl group having 1 to 10 carbon atoms in which a part or all of hydrogen atoms such as a pentafluoroethyl group are substituted with a halogen atom; a pentafluorosulfanyl group; an acetylene group and the like. Of these, alkyl groups having 1 to 10 carbon atoms and halogen atoms are preferable.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. From the viewpoint of synthesis, fluorine atoms and chlorine atoms are preferable.
As the alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 6 carbon atoms is preferable, and an alkyl group having 1 to 4 carbon atoms is more preferable.

The ^{aryl groups represented by Ar 21 to} Ar ²⁶ may or may not have one or more substituents (A3).

Examples of Ar ^{21 to} Ar ²⁶ include groups represented by the following formulas (E-1) to (E-27). * Represents a bond.

From the viewpoint of improving the solubility in a solvent, Ar ²¹ and Ar ²² are preferably any of the formula (E-5), the formula (E-7), the formula (E-8) or the formula (E-11). It is a group represented by. From the viewpoint of improving the solubility in a solvent, Ar ^{23 to} Ar ²⁶ are preferably Formula (E-1), Formula (E-4), Formula (E-9), Formula (E-10), and Formula (E-10). It is a group represented by either E-17) or the formula (E-18).

Ar ^{21 to} Ar ²⁶ may all be the same or different.
It is preferable that Ar ²¹ and Ar ^{22 are the same.}

The hydrocarbon groups having 1 to 20 carbon atoms represented by R ^{21 to} R ^{24 are represented by R 3} , R ⁶ , R ⁸ and R ¹¹ above, except that the example in which the number of carbon atoms is 21 or more is not included. The same example as the hydrocarbon group to be given is given.

Examples of the substituent (A4) that the hydrocarbon group having 1 to 20 carbon atoms represented by R ^{21 to} R ^{24 may have are the same as the above-mentioned substituent (A1).}

Examples of the halogen atom represented by R ^{21 to} R ²⁴ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

R ^{21 to} R ²⁴ are preferably hydrogen atoms.

Specific examples of compound (II) include the compounds shown in Table 2 below.

In Table 2, H represents a hydrogen atom, and E-1, E-6, E-7, E-10, E-17, E-18, and E-19 are the above formulas (E-1), respectively. It means a group represented by the formula (E-6), the formula (E-7), the formula (E-10), the formula (E-17), the formula (E-18), and the formula (E-19).

As the compound (II), the compound (II-1) to the compound (II-24) are preferable, and the compound (II-1) to the compound (II-6), the compound (II-9), and the compound (II-10) are preferable. , Compound (II-15), Compound (II-16), Compound (II-21) or Compound (II-22) is more preferred, Compound (II-3), Compound (II-4), Compound (II-). 9), compound (II-10), compound (II-15) or compound (II-16) is more preferred.

Compound (II) is produced, for example, by reacting a compound represented by the following formula (pt3) with a compound represented by the following formula (AR1) and a compound represented by the following formula (AR2) in a solvent. be able to.

［式中、Ｒ²¹〜Ｒ²⁴は、上述の定義と同一である。］

[In the formula, R ^{21 to} R ²⁴ are the same as the above definitions. ]

Ar ^X- NH ₂ (AR1)
Ar ^X- OH (AR2)
[In the formula, Ar ^X is the same as the definition ^{of Ar 21 to} Ar ^{26 above.} ]

Examples of the compound represented by the formula (pt3) include 1,6,7,12-tetrachloroperylenetetracarboxylic dianhydride.

Examples of the compound represented by the formula (AR1) include 2,6-diisopropylaniline, aniline, 3,5-dimethylalinine, 3,5-di-tert-butylaniline and the like. The compound represented by the formula (AR1) may be used alone or in combination of two or more.

Examples of the compound represented by the formula (AR2) include phenol, 4-fluorophenol, 4-chlorophenol, 4-bromophenol and the like. The compound represented by the formula (AR2) may be used alone or in combination of two or more.

The total amount of the compound represented by the formula (AR1) and the compound represented by the formula (AR2) is usually 1 mol or more and 10 mol or less with respect to 1 mol of the compound represented by the formula (pt3). It is preferably 1 mol or more and 8 mol or less, more preferably 1 mol or more and 6 mol or less, and further preferably 1 mol or more and 4 mol or less.

Examples of the solvent include water; a nitrile solvent such as acetonitrile; methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, and the like. Alcohol solvents such as 1-octanol and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatics such as toluene Hydrocarbon solvents; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 1,2-dichlorobenzene; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethylsulfoxide, acetic acid, propionic acid. , Carobic acid solvent such as butyric acid, imidazole and the like. Preferably, it is N-methylpyrrolidone, imidazole or propionic acid.

The amount of the solvent used is usually 1 to 1000 parts by mass with respect to 1 part by mass of the compound represented by the formula (pt3).

The reaction temperature is usually −100 ° C. or higher and 300 ° C. or lower, preferably −90 ° C. or higher and 200 ° C. or lower, and more preferably −10 ° C. or higher and 150 ° C. or lower. The reaction time is usually 0.5 to 500 hours.

After completion of the reaction, the method for taking out compound (II) is not particularly limited, and it can be taken out by various known methods. Compound (II) can be taken out, for example, by distilling off the solvent. Further, after distilling off the solvent, the obtained residue may be purified by column chromatography, recrystallization or the like. In addition, after completion of the reaction, compound (II) can be taken out by filtration. Further, after filtration, the obtained residue may be purified by column chromatography, recrystallization or the like. The chemical structure of the obtained compound (II) can be analyzed by a known analysis method and its conditions. Such an analysis method is not particularly limited, and examples thereof include an X-ray crystal structure analysis method, a mass spectrometry method (LC), an NMR analysis method, and an elemental analysis method. X-ray crystallography can be described, for example, in Chemistry of Materials, 2012, Vol. 24, p. It can be done in accordance with 4647-4652.

When the colorant (A) contains a perylene compound, the content of the perylene compound is, for example, 0.1% by mass or more, preferably 1% by mass or more, more preferably 3% by mass, based on the total amount of the colorant (A). Above, more preferably 5% by mass or more, still more preferably 10% by mass or more, for example, 95% by mass or less, preferably 90% by mass or less, more preferably 85% by mass or less, still more preferably 80% by mass or less. , More preferably 75% by mass or less.

When the colorant (A) contains a perylene compound, the content of the perylene compound is, for example, 3% by mass or more, preferably 5% by mass or more, more preferably 10 in the total amount of the compound (I) and the perylene compound. It is 5% by mass or more, for example, 95% by mass or less, preferably 90% by mass or less, and more preferably 85% by mass or less.

When the colorant (A) contains the compound (I) and the perylene compound, the compound (I) can also be used as a sensitizer for the perylene compound.

<< Colorant (A1) >>
The colorant (A) of the present invention may be a dye other than the compound (I) and the perylene compound (hereinafter, may be referred to as a dye (A1-1)) and / or a pigment (hereinafter, may be referred to as a pigment (A1-2)). (A) may be contained (hereinafter, the dye (A1-1) and the pigment (A1-2) may be collectively referred to as a colorant (A1)). These may be used alone or in combination of two or more.

As the dye (A1-1), a known dye can be used without particular limitation as long as the compound (I) and the perylene compound are not included, and examples thereof include solvent dyes, acid dyes, direct dyes, and medium dyes. Be done. Examples of the dye include compounds classified as dyes by the Color Index (The Society of Dyers and Colorists Publishing) and known dyes described in Dyeing Note (Color Dyeing Co., Ltd.). According to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acrydin dyes, styryl dyes, coumarin dyes, quinoline. Dyes, nitro dyes, phthalocyanine dyes and the like can be mentioned. Of these, organic solvent-soluble dyes are preferred.

As the pigment (A1-2), a known pigment can be used without particular limitation as long as it does not include a perylene compound. For example, it is classified as a pigment by the Color Index (The Society of Dyers and Colorists Publishing). Pigments can be mentioned.
Pigments classified as pigments include, for example, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, 231;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, Red pigment such as 273;
C. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 32, 36, 38 and other violet color pigments;
C. I. Pigment Green 7, 36, 58, 59, 62, 63 and other green pigments;
C. I. Pigment brown 23, 25 and other brown pigments;
C. I. Pigment Black 1, 7 and other black pigments;
Can be mentioned.

When the colorant (A) further contains the colorant (A1), the lower limit of the total content of the compound (I) and the perylene compound in the colorant (A) is, for example, relative to the total amount of the colorant (A). 1, 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, still more preferably 25% by mass or more, and particularly preferably 50% by mass or more. On the other hand, when the colorant (A) further contains the colorant (A1), the upper limit of the total content of the compound (I) and the perylene compound in the colorant (A) is relative to the total amount of the colorant (A). For example, less than 100% by mass.

The colorant (A) may be treated with a rosin, a surface treatment using a derivative having an acidic group or a basic group introduced therein, a graft treatment on the surface of the colorant (A) with a polymer compound or the like, and sulfuric acid, if necessary. A micronization treatment by an atomization method or the like, a cleaning treatment with an organic solvent or water for removing impurities, a removal treatment of ionic impurities by an ion exchange method or the like may be performed. The particle size of the colorant (A) is preferably substantially uniform.

<Colored resin composition>
The colored resin composition of the present invention contains a colorant (A) and a resin (hereinafter, may be referred to as a resin (B)).
The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter, may be referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)). good.
The colored resin composition of the present invention may further contain a solvent (hereinafter, may be referred to as a solvent (E)).
The colored resin composition of the present invention may further contain a polymerization initiation aid (hereinafter, may be referred to as a polymerization initiation aid (D1)).
The colored resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as a leveling agent (F)).
In the present specification, the compounds exemplified as each component may be used alone or in combination of a plurality of types unless otherwise specified.

When the coloring resin composition contains a solvent (E), a coloring composition containing the coloring agent (A) and the solvent (E) (sometimes referred to as a coloring agent-containing liquid) is prepared in advance, and then the coloring composition is prepared. May be used to prepare a colored resin composition. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains the pigment (A1-2), the coloring composition uses the colorant (A) as the solvent (E). It can be prepared by dispersing and mixing in. The coloring composition may contain a part or all of the solvent (E) contained in the coloring resin composition.

The content of the colorant (A) in the coloring composition is preferably 0.001% by mass or more and 99% by mass or less, more preferably 0.01% by mass or more and 95% by mass or less, and further, based on the total amount of the coloring composition. It is preferably 0.1% by mass or more and 90% by mass or less, and even more preferably 0.1% by mass or more and 50% by mass or less.

The colorant (A) can be made into a state in which the colorant (A) is uniformly dispersed in the solution by carrying out the dispersion treatment by containing the dispersant. When two or more kinds of colorants (A) are used in combination, each of them may be dispersed individually, or a plurality of kinds may be mixed and dispersed.

Examples of the dispersant include surfactants and the like, and any of cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Dispersants include KP (manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark). (BASF), Ajispar (registered trademark) (Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (Big Chemie Co., Ltd.), BYK (registered trademark) (Big Chemie Co., Ltd.), etc. .. As the dispersant, the resin (B) described later may be used.

When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10000 parts by mass or less, preferably 5 parts by mass or more and 5000 parts by mass with respect to 100 parts by mass of the colorant (A). It is 10 parts by mass or more, more preferably 10 parts by mass or more and 3000 parts by mass or less, and further preferably 20 parts by mass or more and 1000 parts by mass or less. When the amount of the dispersant used is in the above range, a coloring composition in a more uniform dispersed state tends to be obtained.

The content of the colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, and more preferably 0.5% by mass or more and 40% by mass or less, based on the total solid content of the coloring resin composition. Yes, more preferably 1% by mass or more and 30% by mass or less. When the content of the colorant (A) is within the above range, the color density when used as a color filter is sufficient, and the required amount of the resin (B) can be contained in the composition, so that it is mechanical. It is preferable because a pattern having sufficient strength can be formed.
Here, the "total amount of solid content" in the present specification means an amount obtained by subtracting the content of the solvent from the total amount of the colored resin composition. The total amount of solids and the content of each component relative to the total amount can be measured by a known analytical means such as liquid chromatography or gas chromatography.

<Resin (B)>
The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and is at least one monomer selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter, "single". It is more preferable that the polymer has a structural unit derived from (sometimes referred to as "mer (a)").
The resin (B) is a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, may be referred to as “monomer (b)”), and a structural unit. / Or a copolymer having other structural units is preferable.
The other structural unit is a monomer copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b). Hereinafter, “monomer (c)) , A structural unit derived from (may be referred to as), a structural unit having an ethylenically unsaturated bond, and the like.

Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid and unsaturated monocarboxylic acids such as o-, m- and p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexendicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo A bicyclounsaturated compound containing a carboxy group such as [2.2.1] hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Carboxylic anhydrides such as the above unsaturated dicarboxylic acid anhydrides excluding fumaric acid and mesaconic acid;
Unsaturated mono-[(meth) acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as monosuccinate [2- (meth) acryloyloxyethyl] and mono [2- (meth) acryloyloxyethyl] phthalates. Kind;
Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid; and the like.
Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an alkaline aqueous solution.
In the present specification, "(meth) acrylic acid" represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.

When the resin (B) is a copolymer having a structural unit derived from the monomer (a), the ratio of the structural unit derived from the monomer (a) in the copolymer is the same. 2 to 60 mol% is preferable in all the constituent units of the polymer.

The monomer (b) has a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring (oxolan ring)) and an ethylenically unsaturated bond. A polymerizable compound having.
The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.

Examples of the monomer (b) include a monomer having an oxylanyl group and an ethylenically unsaturated bond (hereinafter, may be referred to as “monomer (b1)”), and an oxetanyl group and an ethylenically unsaturated bond. Monomer having (hereinafter, may be referred to as “monomer (b2)”), monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, referred to as “monomer (b3)”). In some cases), etc.

The monomer (b1) is, for example, a monomer having a structure in which a linear or branched unsaturated aliphatic hydrocarbon is epoxidized (hereinafter, referred to as “monomer (b1-1)”). (In some cases), a monomer having an epoxidized structure of an unsaturated alicyclic hydrocarbon (hereinafter, may be referred to as “monomer (b1-2)”) can be mentioned.

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable.
Examples of the monomer (b1-1) include glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, and m-vinyl. Benzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis ( Glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (glycidyloxymethyl) styrene, 2,3,4-tris ( Glycidyloxymethyl) styrene, 2,3,5-tris (glycidyloxymethyl) styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (glycidyloxymethyl) styrene, 2, Examples thereof include 4,6-tris (glycidyloxymethyl) styrene.

Examples of the monomer (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, celloxide (registered trademark) 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl. (Meta) acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel Co., Ltd.) , The compound represented by the formula (BI), the compound represented by the formula (BII), and the like.

［式（ＢＩ）及び式（ＢＩＩ）中、Ｒ^a及びＲ^bは、互いに独立に、水素原子、又は炭素数１〜４のアルキル基を表し、該アルキル基に含まれる水素原子は、ヒドロキシ基で置換されていてもよい。
Ｘ^a及びＸ^bは、互いに独立に、単結合、＊−Ｒ^c−、＊−Ｒ^c−Ｏ−、＊−Ｒ^c−Ｓ−又は＊−Ｒ^c−ＮＨ−を表す。
Ｒ^cは、炭素数１〜６のアルカンジイル基を表す。
＊は、Ｏとの結合手を表す。］

[In the formula (BI) and the formula (BII), ^Ra and R ^b independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group. It may be replaced with.
X ^a and X ^b are each independently a single ^{bond, * - R c -, *} - R c -O -, * - represents the R ^c -S- or * -R ^c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group and the like.

Examples of the alkyl group in which the hydrogen atom is substituted with hydroxy include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, and 1 Examples thereof include −hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.

Examples of R ^a and R ^b include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.

Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and the like. Examples thereof include a hexane-1,6-diyl group.

The X ^a and X ^b, preferably a single bond, a methylene group, an ethylene _{group, * - CH 2 -O -,} * - CH 2 CH 2 -O- and the like, more preferably a single bond, * - CH ₂ CH _2- O-can be mentioned (* represents a bond with O).

Examples of the compound represented by the formula (BI) include compounds represented by any of the formulas (BI-1) to (BI-15). Among them, the formula (BI-1), the formula (BI-3), the formula (BI-5), the formula (BI-7), the formula (BI-9) and the formulas (BI-11) to the formulas (BI-15). The compound represented by the formula (BI-1), the formula (BI-7), the formula (BI-9) and the compound represented by the formula (BI-15) are more preferable.

Examples of the compound represented by the formula (BII) include compounds represented by any of the formulas (BII-1) to (BII-15), and among them, the formula (BII-1) and the formula (BII-1) are preferable. (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and compounds represented by formulas (BII-11) to formulas (BII-15) can be mentioned. Preferred examples thereof include compounds represented by the formula (BII-1), the formula (BII-7), the formula (BII-9) and the formula (BII-15).

The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone or in combination of two or more. A compound represented by the formula (BI) and a compound represented by the formula (BII) may be used in combination. When a compound represented by the formula (BI) and a compound represented by the formula (BII) are used in combination, the content ratio thereof [the compound represented by the formula (BI): the compound represented by the formula (BII)] is On a molar basis, it is preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable.
Examples of the monomer (b2) include 3-methyl-3- (meth) acrylicloyloxymethyloxetane, 3-ethyl-3- (meth) acryloyloxymethyloxetane, and 3-methyl-3- (meth) acryloyl. Examples thereof include oxyethyl oxetane and 3-ethyl-3- (meth) acryloyl oxyethyl oxetane.

As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group is more preferable.
Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.

When the resin (B) is a copolymer having a structural unit derived from the monomer (b), the ratio of the structural unit derived from the monomer (b) in the copolymer is the same. 2 to 98 mol% is preferable in all the constituent units of the polymer.

Examples of the monomer (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl. (Meta) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2. 1.0 ^2,6 ] Decane-8-yl (meth) acrylate (In the art, it is commonly referred to as "dicyclopentanyl (meth) acrylate" and "tricyclodecyl (meth) acrylate". ”, Tricyclo [5.2.1.0 ^2,6 ] decane-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decene-8-yl (meth) ) Acrylate (in the art, commonly referred to as "dicyclopentenyl (meth) acrylate"), tricyclo [5.2.1.0 ^2,6 ] decene-9-yl (meth) acrylate, di. Cyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate and benzyl (meth) (Meta) acrylic acid ester such as acrylate;
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Halogen atom-containing (meth) acrylic acid ester such as 2,2,3,3,4,5,5-octafluoropentyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconic acid;
Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2] .1] Hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] Hept-2-ene, 5,6-di (2'-hydroxyethyl) bicyclo [2.2. 1] Hept-2-ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy -5-Methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2] .2.1] Hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-Phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene and 5,6-bis (cyclohexyl) Bicyclounsaturated compounds such as oxycarbonyl) bicyclo [2.2.1] hept-2-ene;
N-Phenylmaleimide, N-Cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3 -Maleimide propionate and dicarbonylimide derivatives such as N- (9-acridinyl) maleimide;
Vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole and p-methoxystyrene; vinyl group-containing nitriles such as (meth) acrylonitrile; chloride. Halogenized hydrocarbons such as vinyl and vinylidene chloride; vinyl group-containing amides such as (meth) acrylamide; esters such as vinyl acetate; dienes such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene ; Etc. can be mentioned.
Of these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo [5.2.1.0 ^2,6 ] decane-8-yl (meth) acrylate, tricyclo [5.2.1] .0 ^2,6 ] Decane-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] Decene-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^{2, 6} ] Decene-9-yl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene, benzyl (meth) acrylate and the like are preferable.

When the resin (B) is a copolymer having a structural unit derived from the monomer (c), the ratio of the structural unit derived from the monomer (c) in the copolymer is the same. 1 to 98 mol% is preferable in all the constituent units of the polymer.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer and 3,4-epoxytricyclo [5.2.1.0 ^2,6. ] Decyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid Copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth) acrylate copolymer, 3,4-epoxytricyclo [5] 2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / vinyl toluene copolymer, 3,4- ^{epoxytricyclo [5.2.1.0 2,6} ] decyl (meth) ) Acrylate / (meth) acrylic acid / benzyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / ( Meta) Acrylate / 2-ethylhexyl (meth) acrylate copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / tricyclo [5.2.1.0] ^2,6 ] Decenyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acrylic loyloxymethyloxetane / (meth) acrylic acid / styrene copolymer, Benzyl (meth) acrylate / (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer, and JP-A-9-106071, JP-A-2004-29518 and JP-A-2004-361455. Examples thereof include the resins described in each publication.
Among them, as the resin (B), a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b) is preferable.
In a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b), the ratio of the structural units derived from each monomer constitutes the copolymer. Within the structural unit, it is preferably in the following range.
Structural unit derived from monomer (a); 2-60 mol% (more preferably 10-50 mol%)
Structural unit derived from monomer (b); 40-98 mol% (more preferably 50-90 mol%)
When the ratio of the structural units derived from the monomers (a) and (b) is in the above range, the storage stability of the colored resin composition, the developability when forming the colored pattern, and the obtained color filter Tends to have excellent solvent resistance.

Two or more kinds of resin (B) may be combined, and in this case, at least the resin (B) is at least.
It is preferable to contain at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b).
It is more preferable to contain at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1).
It is more preferable to contain at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2).
3,4-Epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^{2] , 6} ] Decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth) acrylate copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Decyl (meth) acrylate / (meth) acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / It is even more preferable to contain one or more selected from 2-ethylhexyl (meth) acrylate copolymers.

The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably 1,000 or more and 100,000 or less, more preferably 2,000 or more and 50,000 or less, and further preferably 3,000 or more. It is 30,000 or less. When the weight average molecular weight is in the above range, the unexposed portion tends to have high solubility in a developing solution, and the residual film ratio and hardness of the obtained pattern tend to be high.

The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1 or more and 6 or less, more preferably 1 or more and 5 or less, and further preferably 1 or more and 4 or less. Is.

The acid value (solid content conversion value) of the resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, and more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less. It is more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, still more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 40 mg-KOH / g or more and 135 mg-KOH / g. It is less than or equal to g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be determined by titration using, for example, an aqueous potassium hydroxide solution.

The content of the resin (B) is preferably 5 to 80% by mass, more preferably 10 to 60% by mass, still more preferably 15 to 50% by mass, based on 100% by mass of the solid content of the colored resin composition. It is even more preferably 15 to 45% by mass. When the content of the resin (B) is in the above range, the unexposed portion tends to have high solubility in the developing solution.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, which is preferable. Is a (meth) acrylic acid ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. Etc., as well as the above-mentioned monomers (a), monomer (b) and monomer (c).

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di. Examples thereof include (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (dipentaerythritol hexa (). Meta) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl ) Isocyanurate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, Examples thereof include caprolactone-modified pentaerythritol tetra (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate, and preferably dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4000 or less, more preferably 70 or more and 3500 or less, still more preferably 100 or more and 3000 or less, and even more preferably 150 or more and 2900 or less. Yes, and particularly preferably 250 or more and 1500 or less.

When the polymerizable compound (C) is contained, the content of the polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass, based on the total solid content of the colored resin composition. % Or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, and further preferably 20% by mass or more and 70% by mass or less.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids and the like by the action of light or heat and initiating polymerization, and a known polymerization initiator can be used.

Examples of the polymerization initiator (D) include an oxime compound (for example, an O-acyloxime compound), an alkylphenone compound, a biimidazole compound, a triazine compound, and an acylphosphine oxide compound.

Examples of the O-acyloxym compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-. 1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl)- 3-Cyclopentylpropan-1-one-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1- [9-ethyl -6- (2-methylbenzoyl) -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl) -2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl)- 9H-carbazole-3-yl] -3-cyclopentylpropan-1-imine and N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] -3- Cyclopentylpropan-1-one-2-imine and the like can be mentioned. Further, as the O-acyloxime compound, commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (above, manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) may be used. Among them, as the O-acyloxym compound, N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- At least one selected from the group consisting of 1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyl is preferable. Oxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine is more preferred.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-. Examples thereof include on and 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one. As the alkylphenone compound, commercially available products such as Irgacure (registered trademark) 369, 907, 379 (all manufactured by BASF) may be used.
Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, Also included are 1-hydroxycyclohexylphenyl ketone, an oligomer of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α, α-diethoxyacetophenone and benzyl dimethyl ketal.

Examples of the biimidazole compound include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3-dichlorophenyl) -4. , 4', 5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (alkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2' -Bis (2-chlorophenyl) -4,4', 5,5'-tetra (trialkoxyphenyl) biimidazole (see, for example, JP-A-48-38403, JP-A-62-174204, etc.) and 4 , 4', 5,5'-position phenyl group is substituted with a carboalkoxy group, and a biimidazole compound (see, for example, Japanese Patent Application Laid-Open No. 7-10913) and the like can be mentioned.

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl). -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl)- 1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis ( Trichloromethyl) -6- [2- (fran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methyl) Phenyl) ethenyl] -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine and the like can be mentioned. ..

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may be used.

Further, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzophenone, o-benzoyl methyl benzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone and 2,4,6-trimethylbenzophenone; 9,10-phenanthrene quinone, Kinone compounds such as 2-ethylanthraquinone and benzophenone; 10-butyl-2-chloroacrydone, benzyl, methyl phenylglycoxylate, titanosen compounds and the like can be mentioned.
These are preferably used in combination with the polymerization initiation aid (D1) described later, particularly amines.

The polymerization initiator (D) is a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an oxime compound and a biimidazole compound, and more preferably an oxime compound. It is a polymerization initiator containing, and more preferably a polymerization initiator containing an O-acyloxime compound.

When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is based on 100 parts by mass of the total amount of the total resin (B) and the polymerizable compound (C) contained in the colored resin composition. It is preferably 0.01 part by mass or more and 30 parts by mass or less, and more preferably 0.1 part by mass or more and 20 parts by mass or less. When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

<Polymerization initiation aid (D1)>
The polymerization initiator (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D). When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4-. 2-Ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone and 4,4'-bis ( Ethylmethylamino) benzophenone and the like can be mentioned, preferably 4,4'-bis (diethylamino) benzophenone and the like. Further, as the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy. Examples thereof include anthracene and 2-ethyl-9,10-dibutoxyanthracene.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.

Examples of the carboxylic acid compound include phenylsulfanyl acetic acid, methylphenylsulfanyl acetic acid, ethylphenylsulfanyl acetic acid, methylethylphenylsulfanyl acetic acid, dimethylphenylsulfanyl acetic acid, methoxyphenylsulfanyl acetic acid, dimethoxyphenylsulfanyl acetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, and N. -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like can be mentioned.

When these polymerization initiators (D1) are used, the content thereof is preferably 0. With respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition. It is 01 parts by mass or more and 30 parts by mass or less, more preferably 0.1 parts by mass or more and 20 parts by mass or less.

<Solvent (E)>
The solvent (E) is not particularly limited, and a solvent usually used in the art can be used.
The solvent (E) includes, for example, an ester solvent (a solvent containing -CO-O- in the molecule and not containing -O-) and an ether solvent (a solvent containing -O- in the molecule and containing -CO-O-). No solvent), ether ester solvent (solvent containing -CO-O- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not -CO-O-), alcohol Examples thereof include solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -CO-O-), hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.

Ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone and the like.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether. , Propropylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples thereof include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenyletol, methyl anisole and the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. And so on.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.

Examples of the hydrocarbon solvent include benzene, toluene, xylene, cyclohexane, methylcyclohexane, ethylcyclohexane, normal hexane, styrene, mesitylene and the like.

Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.

Two or more of these solvents may be used in combination.

As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol, and cyclohexanone are preferable, propylene glycol monomethyl ether acetate and cyclohexanone are more preferable, and propylene glycol monomethyl ether acetate is further preferable.

When the solvent (E) is contained, the content of the solvent (E) is usually less than 100% by mass, preferably 99.99% by mass or less, and more preferably 1 with respect to the total amount of the colored resin composition. It is by mass% or more and 99.9% by mass or less, more preferably 10% by mass or more and 99% by mass or less, still more preferably 20% by mass or more and 97% by mass or less, and particularly preferably 30% by mass or more and 95% by mass or less. % Or less, more preferably 40% by mass or more and 95% by mass or less, and particularly preferably 50% by mass or more and 95% by mass or less. When the content of the solvent (E) is within the above range, the flatness at the time of coating is good, and the display characteristics tend to be good because the color density is not insufficient when the color filter is formed. ..

<Leveling agent (F)>
Examples of the leveling agent (F) include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in the side chain.

Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan GK) and the like. ..

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554. R30, RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include MegaFvck (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).

When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 3% by mass or less, more preferably 0.001% by mass, based on the total amount of the colored resin composition. % Or more and 1% by mass or less, more preferably 0.005% by mass or more and 0.5% by mass or less. The content of the pigment dispersant is not included in this content. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored resin composition contains, if necessary, additives known in the art such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, chain transfer agents and the like. It may be.

<Manufacturing method of colored resin composition>
The colored resin composition includes a colorant (A) and a resin (B), and a polymerizable compound (C), a polymerization initiator (D), a polymerization initiator (D1), and a solvent (E), which are used as needed. , Leveling agent (F) and / or other components can be mixed. Mixing can be carried out by known or conventional equipment and conditions.
The colorant (A) may be mixed with a part or all of the solvent (E) in advance and dispersed in a bead mill or the like until the average particle size becomes about 0.2 μm or less. At this time, if necessary, a part or all of the dispersant and the resin (B) may be blended.
The colorant (A) may be used in a state of being previously dissolved in a part or all of the solvent (E).
A target colored resin composition can be prepared by mixing the remaining components with the coloring composition (coloring-containing liquid) obtained as described above so as to have a predetermined concentration.

<Manufacturing method of color filter>
From the colored resin composition, a color filter which may be a color conversion layer can be formed.
A colored coating film can be formed by applying the colored resin composition to a substrate, removing volatile components such as a solvent, and drying the substrate. The colored coating film thus formed is included in the color filter of the present invention.
Examples of the method for forming the colored pattern include a photolithography method, an inkjet method, a printing method and the like. Above all, the photolithography method is preferable. The photolithography method is a method in which the colored resin composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film which is a cured product of the coloring composition layer can be formed by not using a photomask at the time of exposure and / or not developing. The colored pattern and the colored coating film thus formed are the color filters of the present invention.

The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application and the like. For example, it is preferably 30 μm or less, more preferably 20 μm or less, and 6 μm or less. It is more preferably 3 μm or less, and the lower limit is not particularly limited, but it is usually 0.1 μm or more.

The substrate includes a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is silica-coated, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate. Aluminum, silver, silver / copper / palladium alloy thin films, etc. are formed on the glass. Another color filter layer, resin layer, transistor, circuit, or the like may be formed on these substrates.

The formation of each color pixel by the photolithography method can be performed by a known or conventional device or condition. For example, it can be produced as follows.
First, the colored resin composition is applied onto a substrate and dried by heat drying (prebaking) and / or vacuum drying to remove volatile components such as a solvent to obtain a smooth colored composition layer.
Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
The temperature at the time of heat drying is preferably 30 ° C. or higher and 120 ° C. or lower, and more preferably 50 ° C. or higher and 110 ° C. or lower. The heating time is preferably 10 seconds or more and 60 minutes or less, and more preferably 30 seconds or more and 30 minutes or less.
When drying under reduced pressure, it is preferable to carry out drying under a pressure of 50 Pa or more and 150 Pa or less in a temperature range of 20 ° C. or more and 25 ° C. or less.
The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the target color filter.

The coloring composition layer is then exposed via a photomask to form the desired coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used. As the light source used for exposure, a light source that generates light having a wavelength of 250 nm or more and 450 nm or less is preferable. For example, light less than 350 nm is cut by using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm is selectively extracted by using a bandpass filter that extracts these wavelength ranges. You may do it. Specific examples thereof include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps and the like. In addition, since it is possible to uniformly irradiate the entire exposed surface with parallel rays and accurately align the photomask with the substrate on which the coloring composition layer is formed, a stepper (reduced projection exposure machine) and a proxy can be used. It is preferable to use an exposure apparatus (mask aligner) such as a Miti exposure machine.

A coloring pattern is formed on the substrate by developing the coloring composition layer after exposure by bringing it into contact with a developing solution. By development, the unexposed portion of the coloring composition layer is dissolved in a developing solution and removed. As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.03% by mass or more and 5% by mass or less. Further, the developer may contain a surfactant.
The developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development.
The developed substrate is preferably washed with water.

Further, it is preferable to post-bake the obtained coloring pattern. The post-baking temperature is preferably 100 ° C. or higher, more preferably 150 ° C. or higher, further preferably 160 ° C. or higher, preferably 250 ° C. or lower, and more preferably 240 ° C. or lower. The post-baking time is preferably 1 minute or more, more preferably 2 minutes or more, further preferably 10 minutes or more, preferably 120 minutes or less, and more preferably 60 minutes or less.
The colored pattern or the color filter which is the colored coating film thus obtained may be further subjected to a surface coating treatment in order to impart various characteristics.

<Display device>
The color filter is an organic EL display device using an OLED (Organic Light Emitting Node) or the like as a color filter used for a display device (for example, a liquid crystal display device, an organic EL display device, an electronic paper, etc.) and a solid-state imaging element. It is useful as a color filter used in. Since the organic EL display device does not require a backlight, it can be made lighter and thinner than a liquid crystal display device, etc., and can achieve high image quality such as fast response speed and high contrast. It is also used in various fields such as mobile phones, mobile information terminals, and televisions.

According to the colored resin composition containing the colorant (A) of the present invention, it is possible to form a color filter having excellent light resistance. In the present invention, good light resistance means that the change in color before and after the light irradiation test is small, or the change in fluorescence intensity before and after the light irradiation test is small (that is, the maintenance rate of fluorescence intensity is high). say. Further, according to the colored resin composition containing the colorant (A) of the present invention, a color filter having higher fluorescence intensity and excellent brightness is formed as compared with the conventional colored resin composition containing a perylene compound as a colorant. It is possible to do. Furthermore, according to the colored resin composition containing the colorant (A) of the present invention, it is possible to form a color filter having excellent heat resistance. In the present invention, good heat resistance means that the change in color before and after the heating test is small, or the change in fluorescence intensity before and after the heating test is small (that is, the maintenance rate of fluorescence intensity is high). The fluorescence intensity can be measured using, for example, a fluorescence spectrophotometer (FluoroMAX-3; manufactured by HORIBA, Ltd.).

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples as well as the present invention, and appropriate modifications are made to the extent that it can be adapted to the gist of the above and the following. Of course, it is possible to carry out, and all of them are included in the technical scope of the present invention. In the following, unless otherwise specified, "part" means "part by mass" and "%" means "% by mass".

In the following examples, the structure of the compound was confirmed by mass spectrometry (LC; Agilent 1200, MASS; Agilent LC / MSD6130).

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Equipment: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40 ° C
y: tetrahydrofuran Flow rate: 1.0 mL / min Solid content concentration of analytical sample: 0.001 to 0.01 mass%
Injection volume: 50 μL
Detector: RI
Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight and the number average molecular weight obtained above was defined as the degree of dispersion.

(Synthesis Example 1)
<Preparation of compound (IV)>
N ¹ , N ² -bis (2,6-diisopropylphenyl) perylene-3,4,9,10-tetracarboxylic dianimide (manufactured by Tokyo Chemical Industry Co., Ltd.) 20 parts, maleic anhydride (Tokyo Chemical Industry Co., Ltd.) ) And 12 parts of p-chloranyl (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 170 ° C. for 25 hours. When 800 parts of 1 mol / L hydrochloric acid (manufactured by Kanto Chemical Co., Inc.) and 300 parts of acetone (manufactured by Kanto Chemical Co., Inc.) prepared in advance were added while keeping the obtained mixture at 70 ° C. or lower, a yellow precipitate was added. Has occurred. The mixture containing the yellow precipitate was filtered, and the filtered residue was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. and N ¹ , N ² -bis (2,6-diisopropylphenyl) benzo [ghi] perylene-2,3,8,9, represented by the formula (IV). 15 parts of 11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride (hereinafter sometimes referred to as compound (IV)) were obtained (yield 75%).

<Identification of compound (IV)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 805
Exact Mass: 804

(Example 1)
<Compound (I-27), Compound (I-25) and Compound (I-36); Preparation of Colorant 1>
^{N 1} , N ² -bis (2,6-diisopropylphenyl) benzo [ghi] perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8, obtained in Synthesis Example 1 9-bisimide-11,12-acid anhydride 5.0 parts, 2-ethylhexanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.5 parts, 1-bromo-2-ethylhexane (manufactured by Tokyo Chemical Industry Co., Ltd.) ) 4.3 parts, 1-octanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.5 parts, 1-bromooctane (manufactured by Tokyo Chemical Industry Co., Ltd.) 4.3 parts, N, N-dimethylformamide (Kanto Kagaku) 70 parts (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 23 ° C. for 1 hour. Further, 4.6 parts of 1,8-diazabicyclo [5.4.0] -7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise, and the mixture was stirred at 70 ° C. for 6 hours. The resulting mixture was concentrated and 30 parts of methanol was added to give a yellow precipitate. The mixture containing the yellow precipitate was filtered and the filtered residue was washed with 5 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. and purified on a silica gel column (solvent: chloroform). As a result, the compounds represented by the formulas (I-27), (I-25) and (I-36) (I-36) were used. Hereinafter, the compound represented by the formula (I-27) is represented by the compound (I-27), and the compound represented by the formula (I-25) is represented by the compound (I-25) and the formula (I-36). 4.3 parts (yield 66%) of a mixture (colorant 1) of the compound (sometimes referred to as compound (I-36)) was obtained. ^{From the 1} H NMR spectrum, the ratio of compound (I-27), compound (I-25), and compound (I-36) was 53:23:24. In the colorant 1, the compound (I-27) is the compound (Ia) of the present invention, the compound (I-25) is the compound (Ib) of the present invention, and the compound (I-36) is the compound (Ic) of the present invention. ) Corresponds to.

<Identification of compound (I-27)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1047
Exact Mass: 1046
<Identification of compound (I-25)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1047
Exact Mass: 1046
<Identification of compound (I-36)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1047
Exact Mass: 1046

(Example 2)
<Compound (I-14), Compound (I-36) and Compound (I-10); Preparation of Colorant 2>
3.5 parts of 1-octanol is 2.7 parts of 1-hexanol (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and 4.3 parts of 1-bromooctane is 1-bromohexane (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 3.7 parts. Compounds represented by formulas (I-14), formulas (I-36) and formulas (I-10) (hereinafter, formulas (I-14)) are the same as in Example 1 except that the parts are replaced. 5.1 parts of a mixture (colorant 2) of a compound represented by (I-14) and a compound represented by the formula (I-10) may be referred to as compound (I-10) was obtained. (Yield 81%). ^{From the 1} H NMR spectrum, the ratio of compound (I-14), compound (I-36) and compound (I-10) was 47:28:25. In the colorant 2, the compound (I-14) is the compound (Ia) of the present invention, the compound (I-36) is the compound (Ib) of the present invention, and the compound (I-10) is the compound (Ic) of the present invention. ) Corresponds to.

<Identification of compound (I-14)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1019
Exact Mass: 1018

<Identification of compound (I-36)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1047
Exact Mass: 1046

<Identification of compound (I-10)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 991
Exact Mass: 990

(Example 3)
<Compound (I-3), Compound (I-18) and Compound (I-1); Preparation of Colorant 3>
3.5 parts of 2-ethylhexanol is 3.1 parts of 1-heptanol (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and 4.3 parts of 1-bromo-2-ethylhexane is 1-bromoheptane (manufactured by Tokyo Kasei Kogyo Co., Ltd.). 3.9 parts, 1-octanol 3.5 parts 1-pentanol (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 2.4 parts, 1-bromooctane 4.3 parts 1-bromopentan (Tokyo Kasei Kogyo Co., Ltd.) Compounds represented by formulas (I-3), formulas (I-18) and formulas (I-1) in the same manner as in Example 1 except that they were replaced with 3.4 parts (manufactured by Co., Ltd.). Hereinafter, the compound represented by the formula (I-3) is represented by the compound (I-3), and the compound represented by the formula (I-18) is represented by the compound (I-18) and the formula (I-1). 5.1 parts of a mixture (colorant 3) of the compound (sometimes referred to as compound (I-1)) was obtained (yield 83%). ^{From the 1} H NMR spectrum, the ratio of compound (I-3), compound (I-18) and compound (I-1) was 49:27:24. In the colorant 3, the compound (I-3) is the compound (Ia) of the present invention, and the compound (I-18) is the compound (Ib) of the present invention.
In addition, compound (I-1) corresponds to compound (Ic) of the present invention.

<Identification of compound (I-3)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 991
Exact Mass: 990

<Identification of compound (I-18)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1019
Exact Mass: 1018

<Identification of compound (I-1)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 963
Exact Mass: 962

(Example 4)
<Compound (I-4), Compound (I-25) and Compound (I-1); Preparation of Colorant 4>
3.5 parts of 2-ethylhexanol is 3.8 parts of 1-octanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.3 parts of 1-bromo-2-ethylhexane is 1-bromooctanol (manufactured by Tokyo Chemical Industry Co., Ltd.). 4.3 parts, 1-octanol 3.5 parts 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 2.4 parts, 1-bromooctanol 4.3 parts 1-bromopentanol (Tokyo Chemical Industry Co., Ltd.) Compounds represented by formulas (I-4), (I-25) and (I-1) in the same manner as in Example 1 except that the portion was replaced with 3.4 parts (manufactured by Tokyo Chemical Industry Co., Ltd.). Hereinafter, 5.1 parts of a mixture (colorant 4) of the compound (the compound represented by the formula (I-4) may be referred to as the compound (I-4)) was obtained (yield 85%). ^{From the 1} H NMR spectrum, the ratio of compound (I-4), compound (I-25), and compound (I-1) was 50:25:25. In the colorant 4, the compound (I-4) is the compound (Ia) of the present invention, the compound (I-25) is the compound (Ib) of the present invention, and the compound (I-1) is the compound (Ic) of the present invention. ) Corresponds to.

<Identification of compound (I-4)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1005
Exact Mass: 1004

<Identification of compound (I-25)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1047
Exact Mass: 1046

<Identification of compound (I-1)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 963
Exact Mass: 962

(Example 5)
<Compound (I-39), Compound (I-36) and Compound (I-45); Preparation of Colorant 5>
Except that 3.5 parts of 1-octanol was replaced with 2.9 parts of benzyl alcohol (manufactured by Aldrich) and 4.3 parts of 1-bromooctanol was replaced with 3.8 parts of benzyl bromide (manufactured by Tokyo Kasei Kogyo Co., Ltd.). In the same manner as in Example 1, the compound represented by the formula (I-39), the formula (I-36) and the formula (I-45) (hereinafter, the compound represented by the formula (I-39) is compounded (hereinafter, the compound represented by the formula (I-39)). 4.2 parts (yield 66%) of a mixture (colorant 5) of I-39) and the compound represented by the formula (I-45) may be referred to as compound (I-45) was obtained. ^{From the 1} H NMR spectrum, the ratio of compound (I-39), compound (I-36) and compound (I-45) was 47:28:25. In the colorant 5, the compound (I-39) is the compound (Ia) of the present invention, the compound (I-36) is the compound (Ib) of the present invention, and the compound (I-45) is the compound (Ic) of the present invention. ) Corresponds to.

<Identification of compound (I-39)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1025
Exact Mass: 1024

<Identification of compound (I-36)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1047
Exact Mass: 1046

<Identification of compound (I-45)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1003
Exact Mass: 1002

(Example 6)
<Compound (I-16), Compound (I-43) and Compound (I-10); Preparation of Colorant 6>
3.5 parts of 2-ethylhexanol is cyclohexanemethanol (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 3.0 parts, and 4.3 parts of 1-bromo-2-ethylhexane is (bromomethyl) cyclohexane (manufactured by Tokyo Kasei Kogyo Co., Ltd.) ) 3.9 parts, 1-octanol 3.5 parts 1-hexanol (manufactured by Tokyo Kasei Kogyo Co., Ltd.) 2.7 parts, 1-bromooctane 4.3 parts 1-bromohexane (Tokyo Kasei Kogyo Co., Ltd.) )) Compounds represented by formulas (I-16), formulas (I-43) and formulas (I-10) (hereinafter, formulas) in the same manner as in Example 1 except that they were replaced with 3.7 parts. A mixture (colorant 6) of a compound (I-16) may be referred to as a compound represented by (I-16) and a compound represented by the formula (I-43) may be referred to as a compound (I-43). .6 parts were obtained (yield 74%). ^{From the 1} H NMR spectrum, the ratio of compound (I-16), compound (I-43) and compound (I-10) was 50:24:26. In the colorant 6, the compound (I-16) is the compound (Ia) of the present invention, the compound (I-43) is the compound (Ib) of the present invention, and the compound (I-10) is the compound (Ic) of the present invention. ) Corresponds to.

<Identification of compound (I-16)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1003
Exact Mass: 1002

<Identification of compound (I-43)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1015
Exact Mass: 1014

<Identification of compound (I-10)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 991
Exact Mass: 990

(Example 7)
<Compound (I-43) and Compound (I-10); Preparation of Colorant 7>
^{N 1} , N ² -bis (2,6-diisopropylphenyl) benzo [ghi] perylene-2,3,8,9,11,12-hexacarboxylic acid-2,3,8, obtained in Synthesis Example 1 9-bisimide-11,12-acid anhydride 5.0 parts, cyclohexylmethyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) 7.8 parts, cyclohexylmethanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 6.1 parts, N , N-Dimethylformamide (manufactured by Kanto Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 23 ° C. for 1 hour. Further, 4.6 parts of 1,8-diazabicyclo [5.4.0] -7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise, and the mixture was stirred at 60 ° C. for 6 hours. The resulting mixture was concentrated and 30 parts of methanol was added to give a yellow precipitate. The mixture containing the yellow precipitate was filtered and the filtered residue was washed with 5 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. and purified by silica gel column (solvent: chloroform). As a result, N ¹ , N ² -bis (2,6-diisopropylphenyl) benzo represented by the formula (I-43) was obtained. [Ghi] Perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis (cyclohexylmethyl ester) was obtained in 4.1 parts (yield). Rate 66%).

^{N 1} , N ² -bis (2,6-diisopropylphenyl) benzo [ghi] perylene-2,3,8,9,11,12-hexacarboxylic acid-2,3,8, obtained in Synthesis Example 1 9-bisimide-11,12-acid anhydride 5.0 parts, 1-bromohexane (manufactured by Tokyo Chemical Industry Co., Ltd.) 7.3 parts, 1-hexanol (manufactured by Tokyo Chemical Industry Co., Ltd.) 4.0 parts , N, N-Dimethylformamide (manufactured by Kanto Chemical Industry Co., Ltd.) was added, and the mixture was stirred at 23 ° C. for 1 hour. Further, 4.6 parts of 1,8-diazabicyclo [5.4.0] -7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise, and the mixture was stirred at 60 ° C. for 6 hours. The resulting mixture was concentrated and 30 parts of methanol was added to give a yellow precipitate. The mixture containing the yellow precipitate was filtered and the filtered residue was washed with 5 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. and purified by silica gel column (solvent: chloroform). As a result, N ¹ , N ² -bis (2,6-diisopropylphenyl) benzo represented by the formula (I-10) was obtained. [Ghi] 4.3 parts of perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis (1-hexyl ester) was obtained (1). Yield 70%).

10 parts of compound (I-43), 10 parts of compound (I-10), and 200 parts of dichloromethane (manufactured by Kanto Chemical Co., Inc.) were added, and the mixture was stirred at 23 ° C. for 1 hour. The obtained solution was concentrated to obtain 20 parts of a mixture (colorant 7) of compound (I-43) and compound (I-10). In the colorant 7, the compound (I-43) corresponds to the compound (Ib) of the present invention, and the compound (I-10) corresponds to the compound (Ic) of the present invention.

<Identification of compound (I-43)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1015
Exact Mass: 1014

<Identification of compound (I-10)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 991
Exact Mass: 990

(Synthesis Example 2)
<Preparation of Lumogen® F Yellow083>
Lumogen® F Yellow083 represented by the following formula (x) was synthesized according to the description in JP-A-60-203650.

(Synthesis Example 3)
<Preparation of compound INT>

1,6,7,12-Tetrachloro-3,4,9,10-Perylene dianhydride (manufactured by Combichem Co., Ltd.) 10 parts, 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) 13 A portion and 188 parts of propionic acid were added, and the mixture was stirred under reflux for 20 hours. When 50 parts of water was added while keeping the obtained mixture at 20 ° C. or lower, an orange precipitate was formed. The mixture containing the orange precipitate was filtered, and the filtered residue was washed with 200 parts of water and 100 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 12 parts of an intermediate compound (hereinafter, may be referred to as compound INT) (yield 75%).

<Identification of compound INT>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 847
Exact Mass: 846

(Synthesis Example 4)
<Preparation of compound (II-16)>
Manufactured compound INT 5.0 parts, 4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) 1.5 parts, 4-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.1 parts, potassium carbonate ( 11 parts of Kanto Chemical Co., Ltd. and 295 parts of N-methylpyrrolidone (manufactured by Kanto Chemical Co., Ltd.) were added, and the mixture was stirred at 130 ° C. for 13 hours. When 29 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Inc.) and 142 parts of water prepared in advance were added while keeping the obtained mixture at 20 ° C. or lower, a dark red precipitate was formed. The mixture containing the dark red precipitate was filtered, and the filtered residue was washed with 300 parts of water and 150 parts of methanol. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 6.1 parts of a compound represented by the formula (II-16) (hereinafter, may be referred to as compound (II-16)) (yield 81%). ).

<Identification of compound (II-16)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 1237
Exact Mass: 1236

(Synthesis Example 5)
The compound represented by the following formula (II-3) (hereinafter, may be referred to as compound (II-3)) was obtained from Tokyo Chemical Industry Co., Ltd.

(Synthesis Example 6)
<Preparation of resin B1>
An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was placed therein, and the mixture was heated to 80 ° C. with stirring. Then 38 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2.1.0 ^{2, 6} ] A mixed solution of 289 parts of a mixture of decane-9-ylacrylate (content ratio: 1: 1 in molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a solution prepared by dissolving 33 parts of 2,2-azobis (2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropping, the mixture was held at 80 ° C. for 4 hours, cooled to room temperature, and a copolymer (resin B1) solution having a solid content of 35.1% and a viscosity of 125 mPa · s measured with a B-type viscometer (23 ° C.). Got The weight average molecular weight Mw of the resulting copolymer 9.2 × 10 ^3, the degree of dispersion 2.08, acid value on solid basis was 77mg-KOH / g. Resin B1 has the following structural units.

<Example 8>
(1) Solubility test of colorant in solvent (propylene glycol monomethyl ether acetate; hereinafter may be referred to as PGMEA) Approximately 50 mg of solute (colorant 1; compound (I-27), compound (I-25) and compound ( The mixture of I-36)) was weighed and placed in a 20 mL screw tube. About 500 mg of solvent (PGMEA) was added thereto, and the total amount of solute and solvent was weighed. When dissolution was visually confirmed after stirring with a mix rotor in a constant temperature bath at 20 ° C. for 30 minutes, the value calculated by the mass of the solute with respect to the total mass of the solute and the solvent was taken as the solubility. If it did not dissolve, continue to add 500 mg of solvent until it dissolves, and each time it is added, stir with a mix rotor in a constant temperature bath at 20 ° C. for 30 minutes with respect to the total mass of solute and solvent when dissolution is visually confirmed. The value calculated by the mass of the solute was defined as the solubility. The results are shown in Table 3.

(2) Preparation of Coloring Composition Each component was mixed at the following ratio to obtain Coloring Composition 1.
(A) Colorant: Colorant 1 2.6 parts (B) Resin: Resin B1 solution 58 parts (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts

(3) Preparation of Colored Resin Composition Next, each component was mixed at the following ratios to obtain a colored resin composition 1.
Coloring Composition 1 480.6 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzoyloxy- 1- (4-Phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) Part 2 (F) Leveling agent: Polyether-modified silicone oil (Tore Silicone SH8400: Toray)・ Dow Corning Co., Ltd.) 0.15 copies

(4) Preparation of colored coating film (color filter) A colored resin composition is placed on a 5 cm square glass substrate (Eagle XG; manufactured by Corning Inc.), and the film thickness after post-baking becomes 1.9 to 2.1 μm. After applying by the spin coating method as described above, a colored composition layer was formed by prebaking at 100 ° C. for 3 minutes. After allowing to cool, the colored composition layer formed on the substrate was exposed to light at an exposure amount of ^{80 mJ / cm 2} (365 nm standard) under an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). Irradiated. After light irradiation, post-baking was performed at 230 ° C. for 30 minutes in an oven to obtain a colored coating film.
The chromaticity of the colored coating film is evaluated by measuring the spectrum using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.) and using the characteristic function of the C light source in the XYZ color system of CIE. This was done by measuring the xy chromaticity coordinates (x, y) and Y.

(5) Fluorescence intensity measurement The fluorescence spectrum of the obtained colored coating film was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by HORIBA, Ltd.) (excitation side slit 5 nm, fluorescence side slit 10 nm, excitation wavelength 460 nm). The fluorescence intensity at the fluorescence wavelength was determined. Here, the fluorescence wavelength is the wavelength at which the intensity of the fluorescence spectrum is maximum (the peak top of the fluorescence spectrum). Further, the fluorescence intensity means the relative fluorescence intensity, and the fluorescence intensity in this test was evaluated with the fluorescence intensity of Comparative Example 1 as 100. When the fluorescence intensity is more than 100, it means that the fluorescence intensity is higher than that of the colored coating film of Comparative Example 1. The results are shown in Table 3.

(6) Heat resistance test The obtained colored coating film was heated at 230 ° C. for 180 minutes in an oven and in an atmospheric atmosphere. ^{The color difference ΔE *} ab was calculated from the xy chromaticity coordinates (x, y) and the Y measurement values before and after the test by the method described in JIS Z 8730: 2009 (7. Color difference calculation method). The color difference ΔE ^* ab means that the smaller the value, the smaller the color change ^{, and if ΔE *} ab is 3 or less, it can be said that the colored coating film has no practical problem as a color filter. Before and after the heat resistance test, the fluorescence spectrum was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by HORIBA, Ltd.) (excitation side slit 5 nm, fluorescence side slit 10 nm, excitation wavelength 460 nm), and the fluorescence spectrum was measured at the fluorescence wavelength. The fluorescence intensity maintenance rate was determined. The fluorescence intensity retention rate in this test is a value obtained by setting the fluorescence intensity of the colored coating film before the heat resistance test to 100%. The higher the fluorescence intensity retention rate, the better the heat resistance. Further, if the heat resistance of the colored coating film is good, it can be said that the colored pattern produced from the same colored resin composition also has good heat resistance. The results are shown in Table 3.

(7) Light resistance test An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya; cuts light of 380 nm or less) is placed on the obtained colored coating film, and a light resistance tester (SUNTEST CPS +: Toyo Seiki Co., Ltd.) is placed. The xenon lamp light was irradiated for 48 hours. ^{The color difference ΔE *} ab was calculated from the xy chromaticity coordinates (x, y) and the Y measurement values before and after the test by the method described in JIS Z 8730: 2009 (7. Color difference calculation method). The color difference ΔE ^* ab means that the smaller the value, the smaller the color change. If ΔE ^* ab is 3 or less, it can be said that the coating film has no practical problem as a color filter. Before and after the light resistance test, the fluorescence spectrum was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by HORIBA, Ltd.) (excitation side slit 5 nm, fluorescence side slit 10 nm, excitation wavelength 460 nm), and the fluorescence spectrum was measured at the fluorescence wavelength. The fluorescence intensity maintenance rate was determined. The fluorescence intensity retention rate in this test is a value obtained by setting the fluorescence intensity of the colored coating film before the light resistance test to 100%. The higher the fluorescence intensity retention rate, the better the light resistance. Further, if the light resistance of the colored coating film is good, it can be said that the colored pattern produced from the same colored resin composition also has good light resistance. The results are shown in Table 3.

<Examples 9 to 14 and Comparative Example 1>
Instead of 2.6 parts of colorant 1,
2.6 parts of colorant 2 (Example 9),
2.6 parts of colorant 3 (Example 10),
2.6 parts of colorant 4 (Example 11),
2.6 parts of colorant 5 (Example 12),
2.6 parts of colorant 6 (Example 13),
2.6 parts of colorant 7 (Example 14) or 2.6 parts of Lumogen® F Yellow083 (Comparative Example 1)
Was used as a colorant, and a colored resin composition was obtained in the same manner as in Example 8 to prepare a colored coating film. Table 3 shows the solubility of the compound used as the colorant in each example or the compound used in Comparative Example 1 in PGMEA, the fluorescence intensity measurement result, the heat resistance test result, and the light resistance test result in each colored coating film. ..

<Comparative example 2>
An attempt was made to prepare a colored resin composition and a colored coating film by using 2.6 parts of the compound (I-43) as a colorant instead of 2.6 parts of the colorant 1 of Example 8. (I-43) was poorly soluble in PGMEA, and its solubility in PGMEA could not be evaluated, and because it was poorly soluble in PGMEA, a colored coating film could not be obtained.

<Comparative example 3>
A colored resin composition was obtained in the same manner as in Example 8 except that 2.6 parts of the compound (I-10) was used as the colorant instead of 2.6 parts of the colorant 1. A membrane was prepared. The solubility of compound (I-10) in PGMEA and the light resistance test results of the obtained colored coating film are shown in Table 4 together with the results of Example 14 and Comparative Example 2.

Example 14, when the results of Comparative Examples 2 and 3, can not be obtained colored coating film having excellent light resistance in the case of using a colorant comprising one compound (I), R ¹ of formula (I) It has been found that a colored coating film having excellent light resistance can be obtained by using a colorant (A) containing at least two kinds of compounds (I) which are different from each other.

<Example 15>
Each component was mixed at the following ratios to obtain a coloring composition 1-2.
(A) Colorant: Colorant 1 1.3 parts
Compound (II-16) 2.6 parts (B) Resin: Resin B1 solution 54 parts (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts Coloring composition 1-2 was used instead of coloring composition 1. A colored resin composition was obtained in the same manner as in Example 8 except for the above, and a colored coating film was prepared. Table 5 shows the fluorescence intensity measurement results, heat resistance test results, and light resistance test results of the obtained colored coating film.

<Examples 16 to 21 and Comparative Example 4>
Instead of 1.3 parts of colorant 1,
1.3 parts of colorant 2 (Example 16),
1.3 parts of colorant 3 (Example 17),
1.3 parts of colorant 4 (Example 18),
1.3 parts of colorant 5 (Example 19),
1.3 parts of colorant 6 (Example 20),
1.3 parts of colorant 7 (Example 21) or 1.3 parts of Lumogen® F Yellow083 (Comparative Example 4)
A colored resin composition was obtained in the same manner as in Example 15 except that the above was used, and a colored coating film was prepared. Table 5 shows the fluorescence intensity measurement results, heat resistance test results, and light resistance test results for each colored coating film.

<Example 22>
Each component was mixed at the following ratios to obtain coloring compositions 1-3.
(A) Colorant: Colorant 1 1.3 parts
Compound (II-3) 2.6 parts (B) Resin: Resin B1 solution 54 parts (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts Coloring composition 1-3 was used instead of coloring composition 1. A colored resin composition was obtained in the same manner as in Example 8 except for the above, and a colored coating film was prepared. Table 5 shows the fluorescence intensity measurement results, heat resistance test results, and light resistance test results of the obtained colored coating film.

<Examples 23 to 24 and Comparative Example 5>
Instead of 1.3 parts of colorant 1,
1.3 parts of colorant 6 (Example 23),
1.3 parts of colorant 7 (Example 24) or 1.3 parts of Lumogen® F Yellow083 (Comparative Example 5)
A colored resin composition was obtained in the same manner as in Example 22 except that the above was used to prepare a colored coating film. Table 5 shows the fluorescence intensity measurement results, heat resistance test results, and light resistance test results for each colored coating film.

From the above results, it was found that the colored coating film formed from the colored resin composition containing the compound (Ia) or the colorant (A) of the present invention has excellent light resistance. Further, it was found that the compound (Ia) and the colorant (A) of the present invention have high solubility in a solvent (PGMEA) and good solubility. Further, it was found that the colored coating film formed from the colored resin composition containing the compound (Ia) or the colorant (A) of the present invention has high fluorescence intensity and excellent heat resistance.

Claims (11)

Containing at least two compounds represented by the formula (I),
The compounds represented by the two types of formulas (I) ^{are colorants in which at least R 1 of the} formula (I) is different from each other.

[In formula (I),
R ¹ and R ² represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent independently of each other, and −CH ₂ − contained in the hydrocarbon group is −O−, −CO. It may be replaced with −, −OCO− or −COO−.
R ³ and R ⁸ are independent of each other, a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent, or an aromatic heterocyclic group. Representing a group in which these are combined, -CH _2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -OCO- or -COO-.
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁹ and R ¹⁰ independently represent a hydrogen atom, −R ¹¹ , halogen atom, hydroxy group, carboxy group or nitro group.
R ⁴ and R ^5, R ⁵ and R ^6, and R ⁶ and R ⁷ are bonded to each ^{other, -R 12 -CO-O-CO} -R 13 - or ^{-R 12 -CO-N (R 11} ) - A group represented by CO-R ^{13-may be formed.}
R ¹¹ represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and −CH ₂ − contained in the hydrocarbon group is −O−, −CO−, −OCO− or −. It may be replaced with COO-. If there are a plurality of R ¹¹ s, they may be the same or different from each other.
R ¹² and R ¹³ represent divalent hydrocarbon groups having 1 to 15 carbon atoms which may have a single bond or a substituent independently of each other, and are contained in the divalent hydrocarbon group -CH _2. -May be replaced by -O-, -CO-, -OCO- or -COO-. If there are multiple R ¹² , they may be the same or different from each other, and if there ^{are multiple R 13} , they may be the same or different from each other. ] As the compound represented by the formula (I), at least two kinds selected from the group consisting of the compound represented by the formula (Ia), the compound represented by the formula (Ib) and the compound represented by the formula (Ic). A combination of the compound, which is at least a compound represented by the formula (Ia) and a compound represented by the formula (Ib).
(Ii) A combination of a compound represented by the formula (Ia) and a compound represented by the formula (Ic) or a compound represented by the formula (Iii) formula (Ib) and a compound represented by the formula (Ic). The colorant according to claim 1, wherein the colorant is contained in combination.

[In formula (Ia), formula (Ib) and formula (Ic),
R ^1a , R ^2a , R ^1b and R ^1c represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent independently of each other, and −CH ₂ − contained in the hydrocarbon group is It may be replaced with −O−, −CO−, −OCO− or −COO−. However, R ^1a and R ^2a are never the same, and R ^{1 b and R 1 c} are never the same.
R ^{3 to} R ¹⁰ have the same meanings as described above. ] The combination of the compound represented by the formula (Ia) and the compound represented by the formula (Ib), and the compound represented by the formula (Ia) and the formula (Ic). Satisfy at least one of the compounding combinations,
(I) When the combination of the compound represented by the formula (Ia) and the compound represented by the formula (Ib) is satisfied, R ^{1a of the formula (Ia) and R 1 b of the} formula (Ib) are the same. ,
(Ii) When the combination of the compound represented by the formula (Ia) and the compound represented by the formula (Ic) is satisfied, R ^2a of the formula (Ia) and R ^{1c of the} formula (Ic) are the same. The colorant according to claim 2. It contains at least one compound represented by the formula (Ia), a compound represented by the formula (Ib), and a compound represented by the formula (Ic).
In the total amount of the compound represented by the formula (Ia), the compound represented by the formula (Ib) and the compound represented by the formula (Ic),
The content of the compound represented by the formula (Ia) is 35 mol% or more and 65 mol% or less.
The content of the compound represented by the formula (Ib) is 15 mol% or more and 35 mol% or less.
The colorant according to claim 2 or 3, wherein the content of the compound represented by the formula (Ic) is 15 mol% or more and 35 mol% or less. The colorant according to any one of claims 1 to 4, further comprising a perylene compound. A colored resin composition containing the colorant and resin according to any one of claims 1 to 5. The colored resin composition according to claim 6, further containing a polymerizable compound and a polymerization initiator. The colored resin composition according to claim 6 or 7, further containing a solvent. A color filter formed from the colored resin composition according to any one of claims 6 to 8. A display device including the color filter according to claim 9. A compound represented by the formula (Ia).

[In formula (Ia),
R ^1a and R ^2a represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent independently of each other, and −CH ₂ − contained in the hydrocarbon group is −O−, −CO. It may be replaced with −, −OCO− or −COO−. However, R ^1a and R ^2a cannot be the same.
R ³ and R ⁸ are independent of each other, a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent, or an aromatic heterocyclic group. It represents a group comprising a combination thereof, -CH ₂ - contained in the hydrocarbon group is, -O - - -CH ₂ contained in and groups that combine the, - CO -, - OCO- or -COO- in replacing May be.
R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁹ and R ¹⁰ independently represent a hydrogen atom, −R ¹¹ , halogen atom, hydroxy group, carboxy group or nitro group.
R ⁴ and R ^5, R ⁵ and R ^6, and R ⁶ and R ⁷ are bonded to each ^{other, -R 12 -CO-O-CO} -R 13 - or ^{-R 12 -CO-N (R 11} ) - A group represented by CO-R ^{13-may be formed.}
R ¹¹ represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and −CH ₂ − contained in the hydrocarbon group is −O−, −CO−, −OCO− or −. It may be replaced with COO-. If there are a plurality of R ¹¹ s, they may be the same or different from each other.
R ¹² and R ¹³ represent divalent hydrocarbon groups having 1 to 15 carbon atoms which may have a single bond or a substituent independently of each other, and are contained in the divalent hydrocarbon group -CH _2. -May be replaced by -O-, -CO-, -OCO- or -COO-. If there are multiple R ¹² , they may be the same or different from each other, and if there ^{are multiple R 13} , they may be the same or different from each other. ]