KR20220035067A - Colored composition and compound - Google Patents

Abstract

Disclosed is a colored composition comprising: one or more compounds selected from a compound represented by chemical formula IZ1, a compound represented by chemical formula IZ2, a compound represented by chemical formula IZ3, a compound represented by chemical formula IZ4, a compound represented by chemical formula IZ5, and a compound represented by chemical formula IZ6; and at least one of a resin and a solvent.

Description

Coloring composition and compound {COLORED COMPOSITION AND COMPOUND}

The present invention relates to coloring compositions and compounds.

A colored curable composition is used for manufacture of the color filter used for display apparatuses, such as a liquid crystal display device and an electroluminescent display device. As a coloring agent contained in the said colored curable composition, C.I. Pigment Yellow 185 is known (Japanese Patent Laid-Open No. 2016-66020).

The present invention includes the following inventions.

[1] at least one selected from the compound represented by the formula IZ1, the compound represented by the formula IZ2, the compound represented by the formula IZ3, the compound represented by the formula IZ4, the compound represented by the formula IZ5, and the compound represented by the formula IZ6;

The coloring composition containing at least one of resin and a solvent.

[In formula IZ1, R ^O1Z1 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , and R ^7Z1 are, independently of each other, a hydrogen atom, -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO -R ^102Z1 , -OR ^102Z1 , -SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCO- N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown.

R ^2Z1 and R ^3Z1 , R ^3Z1 and R ^4Z1 , and R ^4Z1 and R ^5Z1 may be respectively bonded to each other to form a ring.

R ^101Z1 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102Z1 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M represents a hydrogen atom or an alkali metal atom.

When two or more R ^101Z1 , R ^102Z1 and M exist, they may be the same or different. The broken line indicates the E or Z body.]

[In formula IZ2, R ^CO1Z2 and R ^CO2Z2 each independently represent -OR ^O1Z2 or -NR ^N1Z2 R ^N2Z2 . R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , and R ^5Z2 are, independently of each other, a hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO -R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO- N(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown. R ^2Z2 and R ^3Z2 , R ^3Z2 and R ^4Z2 , and R ^4Z2 and R ^5Z2 may be respectively bonded to each other to form a ring.

R ^101Z2 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^O1Z2 and R ^102Z2 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^101Z2 , R ^102Z2 and M exist, they may be the same or different. The broken line indicates the E or Z body.]

[In formula IZ3, R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , and R ^7Z3 are, independently of each other, a hydrogen atom, -CO-R ^102Z3 , -COO-R ^101Z3 , -OCO- R ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , -SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, optionally substituted carbon number 1 to 40 hydrocarbon group or heterocyclic group which may have a substituent. R ^2Z3 and R ^3Z3 , R ^3Z3 and R ^4Z3 , and R ^4Z3 and R ^5Z3 may be respectively bonded to each other to form a ring. R ^101Z3 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z3 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^101Z3 , R ^102Z3 and M exist, they may be same or different. The broken line indicates the E or Z body.]

[In Formula IZ4, R ^N1Z4 and R ^N2Z4 are, independently of each other, -CO-R ^102Z4 , -COO-R ^101Z4 , -OCO-R ^102Z4 , -COCO-R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^101Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCO-N(R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON( R ^102Z4 ) ₂ , a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , and R ^7Z4 are, independently of each other, a hydrogen atom, -CO-R ^102Z4 , -COO-R ^101Z4 , -OCO-R ^102Z4 , -COCO -R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^101Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCO- N(R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON(R ^102Z4 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown. R ^2Z4 and R ^3Z4 , R ^3Z4 and R ^4Z4 , and R ^4Z4 and R ^5Z4 may be respectively bonded to each other to form a ring. R ^101Z4 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z4 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^101Z4 , R ^102Z4 and M exist, they may be same or different. The broken line indicates the E or Z body.]

[In formula IZ5, R ^N1Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO-N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , halogen atom , a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , and R ^7Z5 are, independently of each other, a hydrogen atom, -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO -R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO- N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and R ^4Z5 and R ^5Z5 may be bonded to each other to form a ring, R ^2Z5 , R ^3Z5 , R ^4Z5 and At least one of R ^5Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO-N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , halogen atom, cya a no group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and at least one set of R ^4Z5 and R ^5Z5 is bonded to form a ring.

R ^101Z5 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102Z5 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M represents a hydrogen atom or an alkali metal atom.

When two or more R ^101Z5 , R ^102Z5 and M exist, they may be same or different. The broken line indicates the E or Z body.]

[In formula IZ6, D represents a structure having an isoindoline skeleton. Z represents -SO ₃ ^- or -CO ₂ ^- . A ^c+ represents a c-valent metal cation. a represents the integer of 1-10.

b represents an integer of 1 or more. c represents the integer of 2-10. d represents an integer of 1 or more. When two or more D, Z, a, or A ^c+ exist, they may be same or different, respectively. Formulas I'Z6 and I"Z6 each represent a partial structure of Formula IZ6, and D, Z, A ^c+ , a, b, c and d represent the same thing as in Formula IZ6.

However, the absolute value of the negative valence of the partial structure represented by the formula I'Z6 and the positive valence of the partial structure represented by the formula I"Z6 are the same.]

[2] A colored curable composition comprising the colored composition according to the above [1] and a polymerizable compound.

[3] A color filter formed from the colored composition according to the above [1] or the colored curable composition according to the above [2].

[4] A liquid crystal display device comprising the color filter according to [3] above.

[5] A compound represented by the formula (IZ1-B).

[In formula IZ1-B, R ^O11Z1 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z1 , R ^21Z1 , R ^31Z1 , R ^41Z1 , R ^51Z1 , R ^61Z1 , and R ^71Z1 are, independently of each other, a hydrogen atom, -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO -R ^102Z1 , -OR ^102Z1 , -SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCO- N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown.

R ^21Z1 and R ^31Z1 , R ^31Z1 and R ^41Z1 , and R ^41Z1 and R ^51Z1 may be respectively bonded to each other to form a ring. provided that at least one of R ^21Z1 , R ^31Z1 , R ^41Z1 , and R ^51Z1 is -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO-R ^102Z1 , -OR ^102Z1 , -SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ₎₂ , -NHCO-R ^102Z1 , -NHCO-N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or At least one set of R ^21Z1 and R ^31Z1 , R ^31Z1 and R ^41Z1 , and R ^41Z1 and R ^51Z1 is bonded to form a ring. R ^101Z1 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102Z1 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom.

When two or more R ^101Z1 , R ^102Z1 and M exist, they may be the same or different.

The broken line indicates the E or Z body.]

[6] A compound represented by the formula IZ2-B.

[In formula IZ2-B, R ^CO11Z2 and R ^CO21Z2 independently represent -OR ^O1Z2 or -NR ^N1Z2 R ^N2Z2 , and at least one of R ^CO11Z2 and R ^CO21Z2 is -NR ^N1Z2 R ^N2Z2 .

R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^21Z2 , R ^31Z2 , R ^41Z2 and R ^51Z2 are, independently of each other, a hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO- R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N (R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or represents a heterocyclic group which may have a substituent, R ^21Z2 and R ^31Z2 , R ^31Z2 and R ^41Z2 , and R ^41Z2 and R ^51Z2 may be bonded to each other to form a ring, R ^21Z2 , R ^31Z2 , R ^41Z2 and R At least one of ^51Z2 is -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO-R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , halogen atom, cyano group , nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R ^21Z2 and R ^31Z2 , R ^31Z2 and R ^41Z2 , and At least one set of R ^41Z2 and R ^51Z2 is bonded to form a ring.

R ^101Z2 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^O1Z2 and R ^102Z2 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M represents a hydrogen atom or an alkali metal atom.

When two or more R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^101Z2 , R ^102Z2 and M exist, they may be the same or different. The broken line indicates the E or Z body.]

[7] A compound represented by the formula IZ3-B.

[In formula IZ3-B, R ^1Z3 , R ^21Z3 , R ^31Z3 , R ^41Z3 , R ^51Z3 , R ^61Z3 , and R ^71Z3 are, independently of each other, a hydrogen atom, -CO-R ^102Z3 , -COO-R ^101Z3 , - OCO-R ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , -SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO -R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, which may have a substituent It represents a C1-C40 hydrocarbon group or the heterocyclic group which may have a substituent.

R ^21Z3 and R ^31Z3 , R ^31Z3 and R ^41Z3 , and R ^41Z3 and R ^51Z3 may be respectively bonded to each other to form a ring.

provided that at least one of R ^21Z3 , R ^31Z3 , R ^41Z3 , and R ^51Z3 is -CO-R ^102Z3 , -COO-R ^101Z3 , -OCO-R ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , -SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or At least one set of R ^21Z3 and R ^31Z3 , R ^31Z3 and R ^41Z3 , and R ^41Z3 and R ^51Z3 is bonded to form a ring. R ^101Z3 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z3 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom.

When two or more R ^101Z3 , R ^102Z3 and M exist, they may be same or different. The broken line indicates the E or Z body.]

[8] A compound represented by formula IZ4.

[In Formula IZ4, R ^N1Z4 and R ^N2Z4 are, independently of each other, -CO-R ^102Z4 , -COO-R ^101Z4 , -OCO-R ^102Z4 , -COCO-R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^101Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCO-N(R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON( R ^102Z4 ) ₂ , a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , and R ^7Z4 are, independently of each other, a hydrogen atom, -CO-R ^102Z4 , -COO-R ^101Z4 , -OCO-R ^102Z4 , -COCO -R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^101Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCO- N(R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON(R ^102Z4 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown. R ^2Z4 and R ^3Z4 , R ^3Z4 and R ^4Z4 , and R ^4Z4 and R ^5Z4 may be respectively bonded to each other to form a ring. R ^101Z4 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z4 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^101Z4 , R ^102Z4 and M exist, they may be same or different. The broken line indicates the E or Z body.]

[9] A compound represented by formula IZ5.

[In formula IZ5, R ^N1Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO-N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , halogen atom , a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , and R ^7Z5 are, independently of each other, a hydrogen atom, -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO -R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO- N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and R ^4Z5 and R ^5Z5 may be bonded to each other to form a ring, R ^2Z5 , R ^3Z5 , R ^4Z5 and At least one of R ^5Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO-N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , halogen atom, cya a no group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and at least one set of R ^4Z5 and R ^5Z5 is bonded to form a ring.

R ^101Z5 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z5 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^101Z5 , R ^102Z5 and M exist, they may be same or different. The broken line indicates the E or Z body.]

[10] A compound represented by the formula IZ6.

[In formula IZ6, D represents a structure having an isoindoline skeleton. Z represents -SO ₃ ^- or -CO ₂ ^- . A ^c+ represents a c-valent metal cation. a represents the integer of 1-10.

b represents an integer of 1 or more. c represents the integer of 2-10.

d represents an integer of 1 or more. When two or more D, Z, a, or A ^c+ exist, they may be same or different, respectively. Formulas I'Z6 and I"Z6 each represent a partial structure of Formula IZ6, and D, Z, A ^c+ , a, b, c and d represent the same thing as in Formula IZ6.

However, the absolute value of the negative valence of the partial structure represented by the formula I'Z6 and the positive valence of the partial structure represented by the formula I"Z6 are the same.]

The coloring composition of this invention is a compound represented by Formula IZ1 (Hereinafter, it may be called compound IZ1.), A compound represented by Formula IZ2 (Hereinafter, it may be called compound IZ2.), A compound represented by Formula IZ3 (Hereinafter, it may be called compound IZ2.) , compound IZ3), a compound represented by formula IZ4 (hereinafter sometimes referred to as compound IZ4), a compound represented by formula IZ5 (hereinafter sometimes referred to as compound 1Z5), and a compound represented by formula IZ6 (hereinafter, may be referred to as compound IZ6) at least one selected from (hereinafter, may be referred to as compound Z), a resin (hereinafter may be referred to as a resin (B)) and a solvent (hereinafter referred to as a solvent) (E) may be referred to) at least one of.

Compound IZ1, compound IZ2, compound IZ3, compound IZ4, compound IZ5, and compound IZ6 include their tautomers and salts thereof, respectively.

Each can be used as a coloring agent.

In the coloring composition of this invention, 1 type or 2 or more types of compound IZ1 may be contained, 1 type or 2 or more types of compound IZ2 may be contained, 1 type or 2 or more types of compound 1Z3 may be contained, 1 Species or two or more types of compounds IZ4 may be contained, 1 type or 2 or more types of compounds IZ5 may be contained, and 1 type or 2 or more types of compounds IZ6 may be contained.

When the coloring composition of this invention contains 1 or more types chosen from compound IZ1, compound IZ2, and compound IZ3, it is preferable to necessarily contain resin (B).

When the coloring composition of this invention contains 1 or more types chosen from compound IZ4, compound IZ5, and compound IZ6, it is preferable to necessarily contain a solvent (E).

When the coloring composition of this invention contains a solvent, it is preferable that compound IZ1, compound IZ2, compound IZ3, compound IZ4, compound IZ5, and compound IZ6 are disperse|distributing with the solvent (E).

When the coloring composition of the present invention contains compound IZ1, the coloring composition is a coloring agent other than compound IZ1 (hereinafter sometimes referred to as coloring agent A1Z1. In the following, compound IZ1 and coloring agent A1Z1 are collectively referred to as “colorant AZ1” In some cases.) may be additionally included. The coloring agent A1Z1 may contain 1 type, or 2 or more types of coloring agents.

When the coloring composition of the present invention contains compound IZ2, the coloring composition is a coloring agent other than compound IZ2 (hereinafter sometimes referred to as coloring agent A1Z2. In the following, compound IZ2 and coloring agent A1Z2 are collectively referred to as “colorant AZ2” In some cases.) may be additionally included. The coloring agent A1Z2 may contain 1 type, or 2 or more types of coloring agents.

When the coloring composition of the present invention contains compound IZ3, the coloring composition is a coloring agent other than compound IZ3 (hereinafter sometimes referred to as coloring agent A1Z3. In the following, compound IZ3 and coloring agent A1Z3 are collectively referred to as “colorant AZ3” In some cases.) may be additionally included. The coloring agent A1Z3 may contain 1 type, or 2 or more types of coloring agents.

When the coloring composition of the present invention contains compound IZ4, the coloring composition is a coloring agent other than compound IZ4 (hereinafter sometimes referred to as coloring agent A1Z4. In the following, compound IZ4 and coloring agent A1Z4 are collectively referred to as “colorant AZ4” In some cases.) may be additionally included. The coloring agent A1Z4 may contain 1 type, or 2 or more types of coloring agents.

When the coloring composition of the present invention contains compound IZ5, the coloring composition is a coloring agent other than compound IZ5 (hereinafter sometimes referred to as coloring agent A1Z5. In the following, compound IZ5 and coloring agent A1Z5 are collectively referred to as “colorant AZ5” In some cases.) may be additionally included. The coloring agent A1Z5 may contain 1 type, or 2 or more types of coloring agents.

When the coloring composition of the present invention contains the compound IZ6, the coloring composition is a colorant other than the compound IZ6 (hereinafter sometimes referred to as colorant A1Z6. In the following, compound IZ6 and colorant A1Z6 are collectively referred to as “colorant AZ6” In some cases.) may be additionally included. The coloring agent A1Z6 may contain 1 type, or 2 or more types of coloring agents.

At least one selected from the colorant A1Z1, the colorant A1Z2, the colorant A1Z3, the colorant A1Z4, the colorant A1Z5, and the colorant A1Z6 is hereinafter collectively referred to as the colorant ZZ. It is preferable that the colorant ZZ contains a yellow colorant or a green colorant.

At least one selected from the colorant AZ1, the colorant AZ2, the colorant AZ3, the colorant AZ4, the colorant AZ5, and the colorant AZ6 is hereinafter collectively referred to as the colorant ZZZ.

It is preferable that the coloring composition of this invention contains both resin (B) and a solvent (E).

In addition, the colored curable composition of the present invention is one selected from the compound represented by the formula IZ1, the compound represented by the formula IZ2, the compound represented by the formula IZ3, the compound represented by the formula IZ4, the compound represented by the formula IZ5, and the compound represented by the formula IZ6 more than species,

At least one of a resin (B) and a solvent (E), and a polymeric compound (C) are included.

In other words, the epigenetic curable composition of the present invention contains a coloring composition and a polymerizable compound (C).

The colored curable composition of this invention may contain the polymerization initiator (D).

The colored curable composition of this invention may contain the polymerization initiation auxiliary|assistant (D1).

The coloring composition of this invention may also contain a leveling agent (F) and antioxidant further.

<Compound IZ1>

Compound IZ1 is a compound represented by Formula (IZ1).

[In formula (IZ1), R ^O1Z1 represents a hydrogen atom, a C1-C40 hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , and R ^7Z1 are, independently of each other, a hydrogen atom, -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO -R ^102Z1 , -OR ^102Z1 , -SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCO- N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown.

R ^2Z1 and R ^3Z1 , R ^3Z1 and R ^4Z1 , and R ^4Z1 and R ^5Z1 may be respectively bonded to each other to form a ring. R ^101Z1 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z1 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^101Z1 , R ^102Z1 and M exist, they may be the same or different. The broken line indicates the E or Z body.]

The hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 has 1 to 40 carbon atoms, preferably 1 to 30, More preferably, it is 1-20, More preferably, it is 1-15, Especially preferably, it is 1-10.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 include a methyl group, an ethyl group, a propyl group, a butyl group, straight-chain alkyl groups such as pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, heptadecyl group, octadecyl group, and icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl)pentyl group, (2- methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group and (3-ethyl) heptyl group branched chain alkyl groups and the like; Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-pro alkenyl groups such as phenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl; and the like. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, and particularly preferably 1 to 10 and still more preferably 1 to 8, and still more preferably 1 to 5. Especially, it is especially preferable that it is a C1-C10, More preferably, it is a C1-C8 linear or branched alkyl group, and a methyl group, an ethyl group, and a tert- butyl group are especially preferable.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 include cyclopropyl group, 1-methylcyclopropyl group , cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethyl Cyclohexyl 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-dimethylcyclo Hexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclo cycloalkyl groups such as a hexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; Cycloalkenyl groups, such as a cyclohexenyl group (For example, cyclohexa-2-ene, cyclohexa-3-ene), a cycloheptenyl group, and a cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane, etc. are mentioned. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, still more preferably 4 to 15, particularly More preferably, it is 5-15, Most preferably, it is 5-10. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

Examples of the aromatic hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , and R ^7Z1 , R ^101Z1 and R ^102Z1 include a phenyl group, an o-tolyl group, a m-tolyl group, and p -Tolyl 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, 4-vinylphenyl group , o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 4-ethylphenyl group, 4- Butylphenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-vinylphenyl group, 1-naphthyl group, 2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group and anthryl group, pyrethyl group aromatic hydrocarbon groups such as nyl group; and the like. Carbon number of an aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-15.

The hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 is the above-mentioned hydrocarbon group (for example, an aromatic hydrocarbon group, a chain hydrocarbon group group and at least one of an alicyclic hydrocarbon group) may be combined; arylalkenyl groups such as a phenylethenyl group (phenylvinyl group); Aryl alkynyl groups, such as a phenylethynyl group; a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; A cyclohexylmethylphenyl group, a benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. are mentioned.

The group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 is a hydrocarbon group (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group). ), for example, a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, The alkyl group to which one or more alicyclic hydrocarbon groups, such as an adamantylmethyl group, couple|bonded may be sufficient.

These carbon number becomes like this. Preferably it is 4-30, More preferably, it is 6-30, More preferably, it is 6-20, More preferably, it is 4-20, More preferably, it is 4-15, Especially Preferably it is 6-15.

The hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 may have a substituent. The substituent may be monovalent or divalent. The divalent substituent preferably has two bonds bonded to the same carbon atom to form a double bond.

As the monovalent substituent,

Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl)hexyloxy group, hep Tyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenyl ethoxy group, phenyloxy group, o-tolyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2,6-dicyanophenyloxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxy C1-C20, such as a phenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group, and groups represented by the following formulas (preferably a C1-C10 hydrocarbon group or its derivatized group (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably chlorine atom), a C1-C10 alkylsulfamoyl group (preferably) preferably an oxy group in which a group derivatized with an octylsulfamoyl group), etc.) is bound to one side;

Methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethyl)hexylthio group, heptylthio group, octylthio group, nonylthio group , a sulfanyl group to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a decylthio group, an undecylthio group, a dodecylthio group, an icosylthio group, a phenylthio group and an o-tolylthio group;

an epoxy group, an oxetanyl group, a tetrahydrofuryl group, a tetrahydropyranyl group;

formyl group;

Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the following formulas, such as a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivatized group thereof (for example, a carboxy group , a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) When it is set as a canoyl group, carbon number becomes like this. Preferably it is 2-12);

Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group , decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, icosyloxycarbonyl group, phenyloxycarbonyl group, o-tolyloxycarbonyl group, etc. to 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) ) a group derivatized with an oxycarbonyl group to which it is bonded;

amino group; N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diiso group Propylamino group, N-butylamino group, N,N-dibutylamino group, N-isobutylamino group, N,N-diisobutylamino group, N-sec-butylamino group, N,N-disec-butylamino group, N- tert-butylamino group, N,N-ditert-butylamino group, N-pentylamino group, N,N-dipentylamino group, N-(1-ethylpropyl)amino group, N,N-di(1-ethylpropyl)amino group , N-hexylamino group, N,N-dihexylamino group, N-(2-ethyl)hexylamino group, N,N-di(2-ethyl)hexylamino group, N-heptylamino group, N,N-diheptylamino group, N-octylamino group, N,N-dioctylamino group, N-nonylamino group, N,N-dinonylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N -Propylmethylamino group, N,N-isopropylmethylamino group, N,N-butylmethylamino group, N-decylamino group, N,N-decylmethylamino group, N-undecylamino group, N,N-undecylmethylamino group, N-dodecylamino group, N,N-dodecylmethylamino group, N-icosylamino group, N,N-icosylmethylamino group, N,N-tert-butylmethylamino group, N,N-phenylmethylamino group, and the like; One or two hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), such as a group represented by the following formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a preferably a chlorine atom), an amino group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

sulfamoyl group; N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N,N-diethylsulfamoyl group, N-propylsulfamoyl group, N,N-dipropylsulfamoyl group, N-isopropylsulfamoyl group, N,N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N,N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N,N-diiso Butylsulfamoyl group, N-sec-butylsulfamoyl group, N,N-disec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N-pentyl group sulfamoyl group, N,N-dipentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N, N-dihexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N,N-diheptylsulfamo Diyl, N-octylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-octylmethylsulfamoyl group, N-nonylsulfamoyl group, N,N-dinonylsulfamoyl group, N-phenylsulfa Moyl group, N,N-diphenylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-butylmethyl Sulfamoyl group, N-decylsulfamoyl group, N,N-decylmethylsulfamoyl group, N-undecylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N-dodecylsulfamoyl group, N, N-dodecylmethylsulfamoyl group, N-icosylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, etc. , and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a sulfamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms), such as amino groups, decanoylamino groups, undecanoylamino groups, dodecanoylamino groups, henicosanoylamino groups, benzoylamino groups, and groups represented by the following formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. a carbonylamino group to which the group) is bonded (when the carbonylamino group is an alkanoylamino group, the carbon number is preferably 1 to 12);

hydroxyl group; Halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;

a carboxyl group, -CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); a sulfo group, —SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium) nitro group; cyano group; formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, and the like, and groups having 1 to 20 carbon atoms (preferably 1 to carbon atoms) 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) a carbonyloxy group (when the carbonyloxy group is an alkanoyloxy group, the carbon number is preferably 1 to 10) to which a group derivatized with a derivatized group) is bonded;

Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl)hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, unde A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a silsulfonyl group, a dodecylsulfonyl group, an icosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, and a group represented by the following formula or a derivatized group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. ) is a sulfonyl group to which it is bonded;

carbamoyl group; N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N,N-diethylcarbamoyl group, N-propylcarbamoyl group, N,N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N,N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N,N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N,N-diiso Butylcarbamoyl group, N-sec-butylcarbamoyl group, N,N-disec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N-pentyl group Carbamoyl group, N,N-dipentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N, N-dihexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N,N-diheptylcarbamo group Diyl, N-octylcarbamoyl group, N,N-dioctylcarbamoyl group, N-nonylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-octylbutylcarbamoyl group, N,N- dinonylcarbamoyl group, N-phenylcarbamoyl group, N,N-diphenylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-isopropylmethyl Carbamoyl group, N,N-butylmethylcarbamoyl group, N-decylcarbamoyl group, N,N-decylmethylcarbamoyl group, N-undecylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N-dodecylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N-icosylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, One or two C1-C20 (preferably C1-C10) hydrocarbon groups, such as N,N-phenylmethylcarbamoyl group, and the group represented by the following formula, or its derivatized group (for example, a carboxy group , a carbamoyl group substituted with a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group);

Trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluoro All hydrogen atoms such as octyl group, perfluorononyl group, perfluorodecyl group, perfluorodecyl group, perfluorododecyl group, perfluoroicosyl group, perfluorocyclohexyl group and perfluorophenyl group a hydrocarbon group having 1 to 20 carbon atoms substituted with a fluorine atom;

Perfluoroethylmethyl group, perfluoropropylmethyl group, perfluoroisopropylmethyl group, perfluorobutylmethyl group, perfluoropentylmethyl group, perfluorohexylmethyl group, perfluoroheptylmethyl group, perfluorooctylmethyl group, purple A linear or branched chain having 1 to 20 carbon atoms in which all hydrogen atoms such as luoronylmethyl group, perfluorodecylmethyl group, perfluoroundecylmethyl group, perfluorododecylmethyl group, and perfluoroicosylmethyl group are substituted with fluorine atoms a hydrocarbon group having 1 to 20 carbon atoms substituted with an alkyl group of;

Some of the hydrogen atoms such as 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group and 2,4,6-trifluorophenyl group are substituted with fluorine having 1 to 20 carbon atoms (preferably from 1 to 20 carbon atoms) The hydrocarbon group of 10);

-CO-SH, -CO-S-CH ₃ , -CO-S-CH ₂ CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₂ a thiocarbonyl group bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as -CH ₃ , a thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms such as -CO-SC ₆ H ₅ ;

*-COCO-R represented by the following formula (wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms (for example, those having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or its a derivatized group (for example, a group derivatized with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) ) of the group;

*-NRCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those satisfying 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivative thereof a group (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), etc.); The R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those satisfying 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivative thereof a group (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), etc.); The R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-NHCOOR represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OP(O)(OR) ₂ such as *-OP(O)(OCH ₃ ) ₂ (wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms (for example, the hydrocarbon group mentioned above) one that satisfies 1 to 20 carbon atoms, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a chlorine atom) is a group derivatized with an octylsulfamoyl group), etc.), and the R groups may be the same or different from each other, and may be bonded to each other to form a ring);

*-SiR ₃ such as *-Si(CH ₃ ) ₃ , *-Si(CH ₂ CH ₃ ) ₃ , *-Si(CH ₅ ) ₃ and *-Si(CH(CH ₃ ) ₂ ) ₃ , where , R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group) , a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), wherein R may be the same as or different from each other, group may be bonded to form a ring); and the like.

Examples of the divalent substituent include an imino group substituted by an oxo group, a thioxo group, an imino group, an imino group substituted by an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted by an aryl group having 6 to 20 carbon atoms. can Examples of the imino group substituted by the alkyl group include CH ₃ -N=, CH ₃ -CH ₂ -N=, CH ₃ -(CH ₂ ) ₂ -N=, and CH ₃ -(CH ₂ ) ₃ -N=. there is. Examples of the imino group substituted by the aryl group include C ₆ H ₅ -N=.

As a substituent of a C1-C40 hydrocarbon group, Preferably, the substituent of group s1 is mentioned. The derivatized group shown below is preferably a group derivatized with a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) or the like. Do.

[group s1]

an oxy group in which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded to one side; a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; halogen atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom, a linear or branched alkyl group having 1 to 20 carbon atoms; a hydrocarbon group having 1 to 20 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo.

As a substituent of a C1-C40 hydrocarbon group, More preferably, the substituent of group s2 is mentioned.

[group s2]

an oxy group in which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms;

sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof;

a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

hydroxyl group; a fluorine atom, a chlorine atom, a bromine atom;

-CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms in which all of the hydrogen atoms are substituted with fluorine atoms;

a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo.

As the hydrocarbon group having 1 to 40 carbon atoms having a substituent represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 , a monovalent or divalent substituent is a hydrocarbon group having 1 to 40 carbon atoms, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms having a monovalent or divalent substituent, and 3 to 30 carbon atoms having a monovalent or divalent substituent A saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group having 6 to 30 carbon atoms having a monovalent or divalent substituent, or a group combining hydrocarbon groups include a group having 1 to 30 carbon atoms having a monovalent or divalent substituent;

More preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, and 6 carbon atoms having a substituent of group s1 As a group of ∼20 aromatic hydrocarbon group or a combination of hydrocarbon groups, it may be a group having 1 to 20 carbon atoms having a substituent of group s1,

Particularly preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, and 6 carbon atoms having a substituent of group s2 Examples of the aromatic hydrocarbon group of ∼15 or the group combining hydrocarbon groups include a group having 1 to 15 carbon atoms having a substituent of group s2.

The heterocyclic group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 may be monocyclic or polycyclic, preferably heterocyclic as a component of the ring. It is a heterocycle containing atoms. As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned.

The heterocyclic group preferably has 3 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, still more preferably 3 to 20 carbon atoms, still more preferably 3 to 18 carbon atoms, still more preferably 3 to 15 carbon atoms. and particularly preferably 3 to 14.

Examples of the heterocycle containing a nitrogen atom include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine;

pyrroles such as 2,5-dimethylpyrrole, pyrazoles such as 2-methylpyrazole and 3-methylpyrazole, and 5-membered rings such as imidazole, 1,2,3-triazole and 1,2,4-triazole systemic unsaturated heterocycle;

pyrimidines such as pyridine, pyridazine and 6-methylpyrimidine; 6-membered ring unsaturated heterocycles such as pyrazine and 1,3,5-triazine;

quinoxes such as imidazole, indoline, isoindoline, indole, indolizine, benzoimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, and 3-methylquinoxaline condensed bicyclic heterocycles such as saline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole and benzopiperidine;

condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and the like.

Examples of the heterocycle containing an oxygen atom include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane. ; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4,5]decane and 1,4-dioxaspiro[4,5]nonane; lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone;

5-membered ring unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran; Condensed bicyclic heterocycles, such as benzopyran, such as 1-benzofuran and 4-methylbenzopyran, benzodioxole, chroman, and isochroman; Condensed tricyclic heterocycles, such as xanthene and dibenzofuran; and the like.

As a heterocyclic ring containing a sulfur atom, 5-membered ring system saturated heterocycles, such as dithiolane; 6-membered ring-based saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl 1,3-dithiane; 5-membered ring unsaturated heterocycles, such as thiophene, such as 3-methylthiophene and 2-carboxythiophene, benzothiopyran, such as 4H-thiopyran and benzotetrahydrothiopyran; Condensed bicyclic heterocycles, such as benzothiophene;

condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.

Examples of the heterocycle containing a nitrogen atom and an oxygen atom include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone. Summons;

Monocyclic unsaturated heterocycles, such as isoxazole, such as oxazole, such as 4-methyloxazole, 2-methylisoxazole, and 3-methylisoxazole; Condensed bicyclic heterocyclic rings, such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline; condensed tricyclic heterocycles such as phenoxazine; and the like.

As a heterocyclic ring containing a nitrogen atom and a sulfur atom, Monocyclic heterocyclic rings, such as thiazole, such as 3-methylthiazole and 2, 4- dimethylthiazole; Condensed bicyclic heterocycles, such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine; and the like.

The heterocyclic ring may be a group combining the above-mentioned hydrocarbon groups, and examples thereof include a tetrahydrofurylmethyl group and the like.

In addition, the said heterocyclic ring may be represented by the following formula|equation.

The heterocyclic group may be a heterocyclic group formed by bonding two or more of R ^1Z1 to R ^5Z1 . Such a heterocyclic group has a ring structure of two or more rings together with the benzene ring to which R ^1Z1 to R ^5Z1 are bonded. As a ring structure of this two or more rings, the structure of the following formula is mentioned, for example.

The bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is removed.

The heterocyclic group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 may have a substituent. Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 may have. Moreover, when the said heterocyclic ring contains the nitrogen atom as its structural element, the hydrocarbon group mentioned above may couple|bond with the substituent to this nitrogen atom.

Preferred examples of the substituent include the same as preferred substituents which the hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 may have. can Examples of the heterocyclic group having a substituent represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 include a heterocyclic group having a monovalent or divalent substituent. and preferably a heterocyclic group having a substituent of group s1, more preferably a heterocyclic group having a substituent of group s2.

The number of substituents (1st substituent) which the said hydrocarbon group or heterocyclic group may have may be one, or two or more may be sufficient as them, and two or more substituents may mutually independently be the same or different. Moreover, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

Hereinafter, R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 of -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO-R ^102Z1 , -OR ^102Z1 , -SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCO-N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , a halogen atom, -SO ₃ M, and -CO ₂ M are demonstrated.

As -CO-R ^102Z1 , a formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the above formulas, such as a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxyl group, alcohol A carbonyl group (a group derivatized with an agar, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) bonded thereto (the carbonyl group is an acyl group) In the compound shown in Table 1Z1 to Table 7Z1 and Table 10Z1 to Table 13Z1, groups corresponding to -CO-R ^102Z1 are mentioned, preferably having 1 to 11 carbon atoms (more Preferably, a carbonyl group having 1 to 10 carbon atoms or a derivatized group thereof bonded thereto (when the carbonyl group is an alkanoyl group, the carbon number is more preferably 2 to 12) and Tables 1Z1 to 7Z1 and Tables 10Z1 to In the compound shown in Table 13Z1, the group corresponding to -CO-R ^102Z1 , etc. are mentioned.

-COO-R ^101Z1 is a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, Octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, etc. 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) and the group corresponding to -COO-R ^101Z1 in the compound shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1 and an oxycarbonyl group) to which a group derivatized with a diyl)) is bonded, and the like, preferably having 1 to carbon atoms. and the group corresponding to -COO-R ^102Z1 in the compound shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1 and the oxycarbonyl group to which the hydrocarbon group of 10 or a derivatized group thereof is bonded.

As -OCO-R ^102Z1 , a formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, etc., and groups represented by the above formulas having 1 to 40 carbon atoms (preferably from 1 to carbon atoms). 20) of a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) In the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1, -OCO in the carbonyloxy group to which a carbonyloxy group (a group derivatized with, etc.) is bonded (when the carbonyloxy group is an acyloxy group, the number of carbon atoms is 2 to 41) a group corresponding to -R ^102Z1 , etc., preferably a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a carbonyloxy group to which a derivatized group thereof is bonded (the carbonyloxy group is an acyl group). In the case of an oxy group, the number of carbon atoms is more preferably 2 to 12) and the group corresponding to -OCO-R ^102Z1 in the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1, and the like.

-COCO-R ^102Z1 is a methyloxalyl group, an ethyloxalyl group, a propyloxalyl group, a butyloxalyl group, a pentyloxalyl group, a hexyloxalyl group, a (2-ethyl)hexyloxalyl group, a heptyloxalyl group , octyloxalyl group, nonyloxalyl group, decyloxalyl group, undecyloxalyl group, dodecyloxalyl group, icosyloxalyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as a tolyloxalyl group and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen ( preferably a chlorine atom), an oxalyl group to which a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. is bonded, and Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1 In the compound shown, the group corresponding to -COCO-R ^102Z1 , etc. are mentioned.

-OR ^{102Z1 is} a hydroxyl group; Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group Group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2 ,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyl group Oxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyl Oxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-e A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof, such as a oxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, and a group represented by the above formula A group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) is bonded and a group corresponding to -OR ^102Z1 in the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1. The group corresponding to -OR ^102Z1 in the compound shown in the time period, Table 1Z1 - Table 7Z1, and Table 10Z1 - Table 13Z1, etc. are mentioned.

-SO ₂ -R ^{101Z1 is} a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl)hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, and a nonyl group. sulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc. A hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfa) sulfonyl group) to which a group derivatized with a moyl group)) is bonded, and a group corresponding to -SO ₂ -R ^101Z1 in the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1, preferably and the group corresponding to -SO ₂ -R ^101Z1 in the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1 and a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded.

As -SO ₂ N(R ^102Z1 ) ₂ , a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfa Moyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A sulfamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), etc. and Tables 1Z1 to 7Z1 and a group corresponding to -SO ₂ NH(R ^102Z1X ) (R ^102Z1X is the same as R ^102Z1 except that it does not form a hydrogen atom) in the compounds shown in Tables 10Z1 to 13Z1;

N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-dipropylsulfamoyl group, N ,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-disec -Butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group, N,N-dipentylsulfamoyl group, N, N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N,N-diheptylsulfamoyl group, N, N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decylmethylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N ,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, N,N-diphenylsulfamoyl group, etc., and groups represented by the above formulas, etc. of two C1 to C40 (preferably C1 to C20) hydrocarbon groups or derivatized groups thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), 1 to 10 carbon atoms) _A sulfamoyl group substituted with an alkylsulfamoyl group (preferably a group derivatized with an ^{octylsulfamoyl} group) of ) ₂ (provided that R ^102Z1X is the same as R ^102Z1 except that it does not become a hydrogen atom);

In the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1 and a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof preferably -SO ₂ N(R ^102Z1 ) ₂ and groups corresponding to .

-CON(R ^102Z1 ) ₂ is a carbamoyl group; N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarp Bamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group and N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z1 to 7Z1 and a group corresponding to -CONH(R ^102Z1X ) (provided that R ^102Z1X is the same as R ^102Z1 except that it does not form a hydrogen atom) in the compounds shown in Tables 10Z1 to 13Z1;

N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N ,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec -Butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-dibutylcarbamoyl group, N,N-butyloctylcarbamoyl group, N, N-dipentylcarbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N,N-dihexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N, N-diheptylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N,N-decylmethylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-phenylmethylcarbamoyl group and N,N-diphenylcarbamoyl group and two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably preferably chlorine atom), a carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), etc., and Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1. and groups corresponding to -CON(R ^102Z1X ) ₂ (provided that R ^102Z1X is the same as R ^102Z1 except that it does not become a hydrogen atom) in the compound;

Preferably, in the compound shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1 and a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, -CON(R ^102Z1 ) ₂ Corresponds to and the like.

-N(R ^102Z1 ) ₂ is an amino group; N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group , N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, N-dodecylamino group, N- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as an icosylamino group, N-phenylamino group, and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, An amino group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z1 to 7Z1 and Tables a group corresponding to -NH(R ^102Z1X ) (provided that R ^102Z1X is the same as R ^102Z1 except that it does not form a hydrogen atom) in the compounds shown in 10Z1 to Table 13Z1;

N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N, N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N-diisobutylamino group, N,N-disec-butylamino group, N,N-ditert-butylamino group, N,N- Butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, N,N-di(1-ethylpropyl)amino group, N,N-dihexylamino group, N,N-di(2-ethyl) ) hexylamino group, N,N-diheptylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N,N-decylmethylamino group, N,N-undecylmethylamino group, N,N-dode A sylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc., and groups represented by the above formulas, such as groups having 1 to 40 carbon atoms (preferably carbon atoms) 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) a group corresponding to -N(R ^102Z1X ) ₂ in the amino group substituted with a group derivatized with a diyl) and the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1;

Preferably, in the compound shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1, and an amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, a group corresponding to -N(R ^102Z1 ) ₂ and the like.

-NHCO-R ^{102Z1 is} a formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as amino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group, and groups represented by the above formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. group) to which the carbonylamino group is bonded (when the carbonylamino group is an acyl group, the number of carbon atoms is 1 to 40) and -NHCO-R ^102Z1 in the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1 Groups corresponding to the group to

Preferably, a carbonylamino group having 1 to 10 carbon atoms or a derivatized group thereof bonded thereto (when the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10) and Tables 1Z1 to 7Z1 and Tables The group corresponding to -NHCO-R ^102Z1 in the compound shown in 10Z1 - Table 13Z1, etc. are mentioned.

Examples of -NHCON(R ^102Z1 ) ₂ include the groups listed above, and groups corresponding to -NHCON(R ^102Z1 ) ₂ in the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1.

Examples of -NHCOOR ^102Z1 include the groups listed above, and groups corresponding to -NHCOOR ^102Z1 in the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1.

Examples of -OCON(R ^102Z1 ) ₂ include the groups listed above, and groups corresponding to -OCON(R ^102Z1 ) ₂ in the compounds shown in Tables 1Z1 to 7Z1 and Tables 10Z1 to 13Z1.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are preferable.

As M of -SO ₃ M and -CO ₂ M, a hydrogen atom; Alkali metal atoms, such as a lithium atom, a sodium atom, and a potassium atom, are mentioned, Preferably, a hydrogen atom, a sodium atom, and a potassium atom are mentioned.

The -CO-R ^102Z1 , -COO-R ^102Z1 , -OCO-R ^102Z1 , -COCO-R ^102Z1 , -OR ^102Z1 , -SO ₂ -R ^102Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCON(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ Substituents (first substituents) included in 2 are, Or two or more may be sufficient, and two or more substituents mutually independently may be same or different.

Moreover, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

The ring formed by R ^2Z1 and R ^3Z1 , R ^3Z1 and R ^4Z1 , and R ^4Z1 and R ^5Z1 is condensed with the benzene ring of the isoindoline skeleton of the compound represented by formula (IZ1). Examples of the condensed ring structure of the benzene ring and the ring formed by R ^2Z1 and R ^3Z1 , R ^3Z1 and R ^4Z1 , and R ^4Z1 and R ^5Z1 include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, and phenylene. nalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, N-methylphthalimide, N-(1-phenylethyl)phthalimide and tetracene hydrocarbon-based condensed ring structures and partial reduction products thereof (eg, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); Indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, perimidine, phenanthroline and phenazine, etc. of nitrogen-containing condensed heterocycles and partial reduction products thereof; and oxygen-containing condensed heterocycles such as 3-hydrobenzofuran 2-one, and partially reduced products thereof.

When R ^2Z1 and R ^3Z1 , R ^3Z1 and R ^4Z1 , and R ^4Z1 and R ^5Z1 form a ring, the ring may have a substituent. Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 may have. Preferred examples of the substituent include the same as preferred substituents that the hydrocarbon group represented by R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , R ^7Z1 , R ^101Z1 and R ^102Z1 may have. can

When R ^3Z1 and R ^4Z1 form a ring, it is preferable that R ^2Z1 and R ^5Z1 are each independently a hydrogen atom, an amino group and a hydroxyl group.

When R ^2Z1 and R ^3Z1 form a ring, R ^4Z1 and R ^5Z1 preferably do not form a ring, and more preferably R ^4Z1 and R ^5Z1 are hydrogen atoms.

Further, when R ^4Z1 and R ^5Z1 form a ring, R ^2Z1 and R ^3Z1 preferably do not form a ring, and more preferably R ^2Z1 and R ^3Z1 are hydrogen atoms.

In the present invention, R ^1Z1 , R ^6Z1 and R ^7Z1 are preferably a hydrogen atom.

In the present invention, R ^O1Z1 is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, a hydrogen atom or It is more preferably a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrocarbon group having 1 to 10 carbon atoms which may have a hydrogen atom or a substituent, and a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent. It is particularly more preferably a hydrocarbon group or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, particularly preferably a hydrogen atom, a methyl group, an ethyl group or a phenyl group, and most preferably a hydrogen atom, a methyl group or an ethyl group.

From the viewpoint that the retardation value of the color filter manufactured from the coloring composition becomes small, at least one of R ^2Z1 , R ^3Z1 , R ^4Z1 , and R ^5Z1 is -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO-R ^101Z1 , -OR ^102Z1 , -SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCO-N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, optionally having 1 to carbon atoms It is preferable that it is the hydrocarbon group of 40 or the heterocyclic group which may have a substituent,

A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N(R ^102Z1 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z1 , -OR ^102Z1 , -SO ₃ M or -CO ₂ M is more preferable, a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent is still more preferable, and it is even more preferably a nitro group or a tert-butyl group. desirable. Alternatively, at least one set of R ^2Z1 and R ^3Z1 , R ^3Z1 and R ^4Z1 or R ^4Z1 and R ^5Z1 preferably forms a ring.

Compound IZ1 is, wherein at least one of R ^2Z1 , R ^3Z1 , R ^4Z1 , and R ^5Z1 is -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO-R ^102Z1 , -OR ^102Z1 , - SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCO-N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent; , or a compound in which at least one set of R ^2Z1 and R ^3Z1 , R ^3Z1 and R ^4Z1 , and R ^4Z1 and R ^5Z1 is bonded to form a ring is preferable (hereinafter, the compound is referred to as “compound IZ1-B” there are cases). When compound IZ1 is compound IZ1-B, the retardation value of the color filter manufactured from the coloring composition becomes small.

At least one of R ^2Z1 , R ^3Z1 , R ^4Z1 and R ^5Z1 from the viewpoint that the retardation value of the color filter manufactured from the coloring composition becomes small,

A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N(R ^102Z1 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z1 , -OR ^102Z1 , -SO ₃ M or -CO ₂ M is preferred,

It is more preferable that it is a C1-C40 hydrocarbon group which may have a nitro group or a substituent, and it is still more preferable that it is a nitro group or a tert- butyl group. Particularly preferably, R ^3Z1 is a nitro group or a tert-butyl group, wherein R ^2Z1 , R ^4Z1 and R ^5Z1 are a hydrogen atom or R ^2Z1 , R ^3Z1 and R ^5Z1 are a hydrogen atom and R ^4Z1 is a nitro group or a tert-butyl group am.

When the compound IZ1-B is defined by the formula, it is as follows.

[In formula IZ1-B, R ^O11Z1 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. R ^1Z1 , R ^21Z1 , R ^31Z1 , R ^41Z1 , R ^51Z1 , R ^61Z1 , and R ^71Z1 are, independently of each other, a hydrogen atom, -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO -R ^102Z1 , -OR ^102Z1 , -SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCO- N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown.

R ^21Z1 and R ^31Z1 , R ^31Z1 and R ^41Z1 , and R ^41Z1 and R ^51Z1 may be respectively bonded to each other to form a ring.

provided that at least one of R ^21Z1 , R ^31Z1 , R ^41Z1 , and R ^51Z1 is -CO-R ^102Z1 , -COO-R ^101Z1 , -OCO-R ^102Z1 , -COCO-R ^102Z1 , -OR ^102Z1 , -SO ₂ -R ^101Z1 , -SO ₂ N(R ^102Z1 ) ₂ , -CON(R ^102Z1 ) ₂ , -N(R ^102Z1 ) ₂ , -NHCO-R ^102Z1 , -NHCO-N(R ^102Z1 ) ₂ , -NHCOOR ^102Z1 , -OCON(R ^102Z1 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or At least one set of R ^21Z1 and R ^31Z1 , R ^31Z1 and R ^41Z1 , and R ^41Z1 and R ^51Z1 is bonded to form a ring.

R ^101Z1 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z1 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^101Z1 , R ^102Z1 and M exist, they may be the same or different. The broken line indicates the E or Z body. ]

In Formula IZ1-B, R ^O11Z1 , R ^21Z1 , R ^31Z1 , R ^41Z1 , R ^51Z1 , R ^61Z1 , and R ^71Z1 are, respectively, R ^O1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 in Formula (IZ1) , R ^6Z1 , and R ^7Z1 .

In formula IZ1-B, preferred R ^O11Z1 , R ^21Z1 , R ^31Z1 , R ^41Z1 , R ^51Z1 , R ^61Z1 , and R ^71Z1 are, respectively, R ^O1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R in formula (IZ1) The same ones as preferred for ^5Z1 , R ^6Z1 , and R ^7Z1 can be mentioned.

In the formula IZ1-B, (Aspect 1) R ^1Z1 , R ^61Z1 and R ^71Z1 are preferably hydrogen atoms. Moreover, it is also preferable that (Aspect 2) R ^O11Z1 is a C1-C10 hydrocarbon group which may have a hydrogen atom or a substituent. Also (Mode 3), it is preferable that at least one of R ^21Z1 , R ^31Z1 , R ^41Z1 , and R ^51Z1 is a nitro group or a tert-butyl group. The said aspects 1 - 3 may be employ|adopted independently and may be combined suitably.

As a specific example of the compound IZ1, for example, in the formula IZ1-aa, in Table 1Z1, Table 2Z1, Table 3Z1, Table 4Z1, Table 5Z1, Table 6Z1, Table 7Z1, Table 10Z1, Table 11Z1, Table 12Z1, Table 13Z1 and compounds IZ1-1 to IZ1-529 having a substituent shown, or an alkali metal salt thereof.

B ^a1Z1 B ^a2Z1 is a formula (BB1) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1), a formula (BBO8), a formula (BBO10) , represents the partial structure of any of formulas (BBD1) and (BBJ2). As B ^a1Z1 B ^a2Z1 , Formula (BB1), Formula (BB6), Formula (BB8), Formula (BB11), Formula (BB14), Formula (BB19), Formula (BB37), Formula (BB58), Formula (BBJ2), Formulas (BBO8) and (BBO10) are preferable, and Formula (BB1), a formula (BB6), and a formula (BB19) are more preferable.

Each symbol in Table 1Z1, Table 2Z1, Table 3Z1, Table 4Z1, Table 5Z1, Table 6Z1, Table 7Z1, Table 10Z1, Table 11Z1, Table 12Z1, and Table 13Z1 indicates the following partial structures. In addition, in the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ" " represents a benzyl group, "NPR" represents a propyl group,

"IPR" represents an isopropyl group, "IBu" represents an isobutyl group, "EOE" represents -CH ₂ CH ₂ OCH ₂ CH ₃ , "ALL" represents an allyl group, and "HYE" represents 2-hydroxy represents an ethyl group, "COM" represents -CO-CH ₃ , "COE" represents -COO-CH ₂ CH ₃ , "OCM" represents -OCO-CH ₃ , and "OME" represents -O-CH ₃ is represented, "SOT" represents a tosyl group, "SNH" represents -SO ₂ NH-CH ₂ CH(CH ₂ CH ₃ )((CH ₂ ) ₃ CH ₃ ), "SN2" is -SO ₂ Represents N(CH ₃ )((CH ₂ ) ₇ CH ₃ ), "CNM" represents -CONHCH ₃ , "CN2" represents -CON(CH ₃ )C ₆ H ₅ , and "NPH" is -NHC ₆ H ₅ represents,

"NOT" represents -N((CH ₂ ) ₇ CH ₃ ) ₂ , "NCO" represents -NHCO((CH ₂ ) ₄ CH ₃ ), "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO2" represents a nitro group, "SUA" represents -SO ₃ H, and "CBA" represents -CO ₂ H represents, "CHO" represents -CHO, "OCH" represents -OCOH, "OH" represents -OH, "SFM" represents -SO ₂ NH ₂ , and "CBM" represents -CONH ₂ , "NH2" represents -NH2, "NCH" represents _-NHCOH , and * represents a bond.

B ^a1Z1 and B ^a2Z1 each represent a bond, and when B ^a1Z1 is a bond of the following B ¹ , B ^a2Z1 becomes a bond of the following B ² , and when B ^a1Z1 is a bond of the following B ² , B ^a2Z1 becomes ^a bond of the following B1.

[Table 1Z1]

[Table 2Z1]

[Table 3Z1]

[Table 4Z1]

[Table 5Z1]

[Table 6Z1]

[Table 7Z1]

[Table 10Z1]

[Table 11Z1]

[Table 12Z1]

[Table 13Z1]

For example, compound IZ1-1 is a compound represented by formula IZ1-1.

As compound IZ1,

Compound IZ1-1 to compound IZ1-171, compound IZ1-258 to compound IZ1-529 are preferable, and compound IZ1-1 to compound IZ1-171, and compound IZ1-258 to compound IZ1-471 are more preferable;

Compound IZ1-1 to compound IZ1-171 are more preferable, compound IZ1-1 to compound IZ1-111 are still more preferable, compound IZ1-1 to compound IZ1-54 are particularly preferable, and compound IZ1-2 to compound IZ1 -3, compound IZ1-20 to compound IZ1-21, and compound IZ1-38 to compound IZ1-39 are particularly preferred.

Specific examples of compound IZ1 include 1 to 3 hydrogen atoms contained in the compounds shown in Table 1Z1, Table 2Z1, Table 3Z1, Table 4Z1, Table 5Z1, Table 6Z1, Table 7Z1, Table 10Z1, Table 11Z1, Table 12Z1, and Table 13Z1 A compound in which -SO ₃ M or -CO ₂ M is substituted may also be mentioned. For example, a compound in which 1 to 3 sulfo groups are bonded to compound IZ1-1 of Table 1Z1 is represented by the following structure. However, in formula, -(SO ₃ H) shall mean that the hydrogen atom of any one of compound IZ1-1 of Table 1Z1 is substituted.

In the present invention, the compound IZ1-1 to the compound IZ1-171, the compound IZ1-258 to the compound IZ1-529 is preferably a compound in which one to three -SO ₃ M or -CO ₂ M is bonded to the compound IZ1- 1 to compound IZ1-171, compound IZ1-258 to compound IZ1-431 is more preferably a compound in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded;

It is more preferable that the compound IZ1-1 to the compound IZ1-171 is a compound in which one to three pieces of -SO ₃ M or -CO ₂ M are bonded,

It is more preferable that the compound IZ1-1 to the compound IZ1-111 is a compound in which one to three pieces of -SO ₃ M or -CO ₂ M are bonded,

It is particularly preferable that the compound IZ1-1 to the compound IZ1-54 is a compound in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded;

Compound IZ1-2 to compound IZ1-3, compound IZ1-20 to compound IZ1-21, and compound IZ1-38 to compound IZ1-39 are compounds in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded It is particularly preferred.

As the compound (IZ1), in the formula (IZ1), R ^O1Z1 is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, R ^1Z1 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, -SO ₃ M or -CO ₂ M, R ^2Z1 to R 2Z1 to R ^5Z1 is each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102Z1 ₎₂ , a nitro group, or a hydrocarbon having 1 to 20 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms a group, -NHCO-R ^102Z1 , -OR ^102Z1 , -SO ₃ M or -CO ₂ M,

R ^6Z1 and R ^7Z1 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, -SO ₃ M or -CO ₂ is M,

R ^102Z1 is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

M is preferably a hydrogen atom or an alkali metal atom,

R ^O1Z1 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

R ^1Z1 is a hydrogen atom,

R ^2Z1 to R ^5Z1 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102Z1 ) ₂ , a nitro group, or a fluorine atom having 1 carbon atom in which all or part of the hydrogen atoms are substituted A hydrocarbon group of -10, -NHCO-R ^102Z1 , -OR ^102Z1 , -SO ₃ M or -CO ₂ M,

R ^6Z1 and R ^7Z1 are the same group and are a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

R ^102Z1 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

M is more preferably a hydrogen atom or an alkali metal atom,

R ^O1Z1 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

R ^1Z1 is a hydrogen atom,

R ^2Z1 to R ^5Z1 are each, independently, a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102Z1 ) ₂ , a nitro group, a trifluoromethyl group, -OR ^102Z1 , -SO ₃ M or -CO ₂ M;

R ^6Z1 and R ^7Z1 are the same group and represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms;

R ^102Z1 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

M is more preferably a hydrogen atom or an alkali metal atom.

In the compound IZ1, when R ^1Z1 is a hydrogen atom, a compound represented by the formula pt1Z1 (hereinafter sometimes referred to as a phthalonitrile compound) is reacted with a compound represented by the formula pt2Z1 (hereinafter sometimes referred to as an alkoxide compound) After the reaction, it can be prepared by further reacting the compound represented by the formula pt3Z1 with the compound represented by the formula pt4Z1 in the presence of an acid. Further, when R ^1Z1 is other than a hydrogen atom, compound IZ1 can be produced by further reacting with a compound represented by the formula pt5Z1.

[In formula pt1Z1, formula pt2Z1, formula pt3Z1, formula pt4Z1, formula pt5Z1, and formula IZ1, R ^O1Z1 , R ^1Z1 , R ^2Z1 , R ^3Z1 , R ^4Z1 , R ^5Z1 , R ^6Z1 , and R ^7Z1 have the same meanings as above indicates R ^14Z1 represents an alkyl group having 1 to 20 carbon atoms. M ^1Z1 represents an alkali metal atom. LG represents a halogen atom, a methanesulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group.]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ^14Z1 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group, and preferably a C1 group. -6 alkyl groups are mentioned.

Examples of the alkali metal atom represented by M ^1Z1 include a lithium atom, a sodium atom and a potassium atom.

The usage-amount of an alkoxide compound is 0.1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 0.2-5 mol, More preferably, it is 0.3-3 mol, More preferably, it is 0.4-2 mol. it's a mall

The amount of the compound pt3Z1 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 2 moles, with respect to 1 mole of the phthalonitrile compound. am.

The amount of the compound pt4Z1 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 2 moles, with respect to 1 mole of the phthalonitrile compound. am.

Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; and carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid These are mentioned, More preferably, acetic acid is mentioned.

The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, still more preferably 1 to 6 moles with respect to 1 mole of the phthalonitrile compound.

The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z1, and the compound pt4Z1 is usually carried out in the presence of a solvent.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N ,N-dimethylformaldehyde, N-methylpyrrolidone and dimethyl sulfoxide, and more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1- octanol, acetone, methylene chloride, chloroform, N,N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide are exemplified, particularly preferably water, acetonitrile, methanol, ethanol and 2-propanol. can be heard

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of phthalonitrile compounds.

Reaction temperature is 0-200 degreeC normally, Preferably it is 0-100 degreeC, More preferably, it is 0-70 degreeC, More preferably, it is 0-50 degreeC. Reaction time is 0.5 to 300 hours normally.

The amount of compound pt5Z1 to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, further preferably 1 mole of compound IZ1 in which R ^1Z1 is a hydrogen atom. 1 to 2 moles.

In addition, when the compound pt5Z1 is reacted, it is preferable that a base coexist. Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; organometallic compounds such as butyllithium, tert-butyllithium and phenyllithium; Inorganic bases, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, are mentioned.

The amount of the base used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 10 moles, with respect to 1 mole of compound IZ1 in which R ^1Z1 is a hydrogen atom. 2 moles.

In addition, the reaction of compound pt5Z1 is usually carried out in the presence of a solvent. A solvent can be selected from the range similar to the above.

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of compound ^IZ1 in which R<1>Z1 is a hydrogen atom. The reaction temperature of the compound (pt5) is usually -90 to 200°C, preferably -80 to 100°C, more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

When compound IZ1 does not have a sulfo group or -SO ₃ M ²² , a sulfo group or -SO ₃ M ² can be introduced by reacting compound IZ1 with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid.

M ²² represents an alkali metal atom.

Examples of the alkali metal atom represented by M ²² include a lithium atom, a sodium atom and a potassium atom.

The amount of SO ₃ used in the fuming sulfuric acid is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, still more preferably 5 to 25 moles, with respect to 1 mole of compound IZ1. am.

The amount of sulfuric acid used in the fuming sulfuric acid is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, still more preferably 10 to 50 moles with respect to 1 mole of compound IZ1. .

The usage-amount of chlorosulfonic acid is 1-500 mol normally with respect to 1 mol of compound IZ1, Preferably it is 10-300 mol, More preferably, it is 10-200 mol, More preferably, it is 10-150 mol.

The reaction temperature for sulfonation is usually -20 to 200°C, preferably -10 to 100°C, and more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

The method for taking out compound IZ1 from the reaction mixture is not particularly limited, and can be taken out by various known methods. For example, after completion of the reaction, the compound IZ1 can be taken out by filtering the reaction mixture. After filtration, the obtained residue may be subjected to column chromatography, recrystallization, or the like. Further, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and then purified by column chromatography.

<Compound IZ2>

The compound IZ2 is a compound represented by the formula IZ2.

[of formula IZ2,

R ^CO1Z2 and R ^CO2Z2 represent, independently of each other, -OR ^O1Z2 or -NR ^N1Z2 R ^N2Z2 .

R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , and R ^5Z2 are, independently of each other, a hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO -R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO- N(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown.

R ^2Z2 and R ^3Z2 , R ^3Z2 and R ^4Z2 , and R ^4Z2 and R ^5Z2 may be respectively bonded to each other to form a ring. R ^101Z2 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^O1Z2 and R ^102Z2 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom.

When two or more R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^101Z2 , R ^102Z2 and M exist, they may be the same or different. The broken line indicates the E or Z body.]

The hydrocarbon group which may have a substituent represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 has 1 to 40 carbon atoms, preferably It is 1-30, More preferably, it is 1-20, More preferably, it is 1-15, Especially preferably, it is 1-10, Especially preferably, it is 1-5.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 include a methyl group, an ethyl group, a propyl group, a butyl group, straight-chain alkyl groups such as pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, heptadecyl group, octadecyl group, and icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl)pentyl group, (2- methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group and (3-ethyl) heptyl group branched chain alkyl groups and the like; Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-pro alkenyl groups such as phenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl; and the like. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and still more preferably Preferably it is 1-8, Especially more preferably, it is 1-5. Especially, it is especially preferable that it is a C1-C10, More preferably, it is a C1-C8 linear or branched alkyl group, and a methyl group, an ethyl group, and a tert- butyl group are especially preferable.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 include cyclopropyl group, 1-methylcyclopropyl group , cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethyl Cyclohexyl 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-dimethylcyclo Hexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclo cycloalkyl groups such as a hexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; Cycloalkenyl groups, such as a cyclohexenyl group (For example, cyclohexa-2-ene, cyclohexa-3-ene), a cycloheptenyl group, and a cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane, etc. are mentioned. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 4 to 20 carbon atoms, still more preferably 4 to 15 carbon atoms, and particularly More preferably, it is 5-15, Most preferably, it is 5-10. Among them, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group are particularly preferable.

Examples of the aromatic hydrocarbon group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 include a phenyl group, o-tolyl group, m-tolyl group, p- tolyl 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, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 4-ethylphenyl group, 4-butyl Phenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-vinylphenyl group, 1-naphthyl group, 2 -naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group and anthryl group, pyrenyl group aromatic hydrocarbon groups, such as; and the like. Carbon number of an aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-15.

The hydrocarbon group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 is the above-mentioned hydrocarbon group (for example, an aromatic hydrocarbon group, a chain hydrocarbon group group and at least one of an alicyclic hydrocarbon group) may be combined; Arylalkenyl groups, such as a phenylethenyl group (phenylvinyl group); Arylalkynyl groups, such as a phenylethynyl group; a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; A cyclohexylmethylphenyl group, a benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. are mentioned.

The group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 is a hydrocarbon group (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group) As a group combining The alkyl group to which one or more alicyclic hydrocarbon groups, such as a danthanylmethyl group, couple|bonded may be sufficient.

These carbon number becomes like this. Preferably it is 4-30, More preferably, it is 6-30, More preferably, it is 6-20, More preferably, it is 4-20, More preferably, it is 4-15, Especially Preferably it is 6-15.

The hydrocarbon group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 may have a substituent. The substituent may be monovalent or divalent. In the divalent substituent, it is preferable that two bonds are bonded to the same carbon atom to form a double bond.

Examples of the monovalent substituent include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, (2-ethyl ) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1 -Methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6 -Dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyano group Phenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyloxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group, etc. and groups represented by the following formulas, etc. A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) of an oxy group in which a sulfamoyl group (preferably a group derivatized with an octylsulfamoyl group) or the like) is bonded to one side;

Methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethyl)hexylthio group, heptylthio group, octylthio group, nonylthio group , a sulfanyl group to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a decylthio group, an undecylthio group, a dodecylthio group, an icosylthio group, a phenylthio group and an o-tolylthio group;

an epoxy group, an oxetanyl group, a tetrahydrofuryl group, a tetrahydropyranyl group;

formyl group;

Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the following formulas, such as a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivatized group thereof (for example, a carboxy group , a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) In the case of a canoyl group, the carbon number is preferably 2 to 12):

Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group , decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, icosyloxycarbonyl group, phenyloxycarbonyl group, o-tolyloxycarbonyl group, etc., and 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) represented by the following formulas. from a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. an oxycarbonyl group to which a derivatized group) is bonded;

amino group; N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diiso group Propylamino group, N-butylamino group, N,N-dibutylamino group, N-isobutylamino group, N,N-diisobutylamino group, N-sec-butylamino group, N,N-disec-butylamino group, N- tert-butylamino group, N,N-ditert-butylamino group, N-pentylamino group, N,N-dipentylamino group, N-(1-ethylpropyl)amino group, N,N-di(1-ethylpropyl)amino group , N-hexylamino group, N,N-dihexylamino group, N-(2-ethyl)hexylamino group, N,N-di(2-ethyl)hexylamino group, N-heptylamino group, N,N-diheptylamino group, N-octylamino group, N,N-dioctylamino group, N-nonylamino group, N,N-dinonylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N -Propylmethylamino group, N,N-isopropylmethylamino group, N,N-butylmethylamino group, N-decylamino group, N,N-decylmethylamino group, N-undecylamino group, N,N-undecylmethylamino group, N-dodecylamino group, N,N-dodecylmethylamino group, N-icosylamino group, N,N-icosylmethylamino group, N,N-tert-butylmethylamino group, N,N-phenylmethylamino group, and the like; One or two hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), such as a group represented by the following formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a preferably a chlorine atom), an amino group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

sulfamoyl group; N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N,N-diethylsulfamoyl group, N-propylsulfamoyl group, N,N-dipropylsulfamoyl group, N-isopropylsulfamoyl group, N,N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N,N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N,N-diiso Butylsulfamoyl group, N-sec-butylsulfamoyl group, N,N-disec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N-pentyl group sulfamoyl group, N,N-dipentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N, N-dihexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N,N-diheptylsulfamo Diyl, N-octylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-octylmethylsulfamoyl group, N-nonylsulfamoyl group, N,N-dinonylsulfamoyl group, N-phenylsulfa Moyl group, N,N-diphenylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-butylmethyl Sulfamoyl group, N-decylsulfamoyl group, N,N-decylmethylsulfamoyl group, N-undecylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N-dodecylsulfamoyl group, N, N-dodecylmethylsulfamoyl group, N-icosylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, etc. , and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a sulfamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms), such as amino groups, decanoylamino groups, undecanoylamino groups, dodecanoylamino groups, henicosanoylamino groups, benzoylamino groups, and groups represented by the following formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. a carbonylamino group to which the group) is bonded (when the carbonylamino group is an alkanoylamino group, the carbon number is preferably 1 to 12);

hydroxyl group; Halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;

carboxyl group; , —CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); a sulfo group, —SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); nitro group; cyano group;

formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, and the like, and groups having 1 to 20 carbon atoms (preferably 1 to carbon atoms) 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) a carbonyloxy group (when the carbonyloxy group is an alkanoyloxy group, the carbon number is preferably 1 to 10) to which a group derivatized with, etc.) is bonded;

Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl)hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, unde A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a silsulfonyl group, a dodecylsulfonyl group, an icosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, and a group represented by the following formula or a derivatized group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. ) is a sulfonyl group bonded;

carbamoyl group; N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N,N-diethylcarbamoyl group, N-propylcarbamoyl group, N,N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N,N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N,N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N,N-diiso Butylcarbamoyl group, N-sec-butylcarbamoyl group, N,N-disec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N-pentyl group Carbamoyl group, N,N-dipentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N, N-dihexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N,N-diheptylcarbamo group Diyl, N-octylcarbamoyl group, N,N-dioctylcarbamoyl group, N-nonylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-octylbutylcarbamoyl group, N,N- dinonylcarbamoyl group, N-phenylcarbamoyl group, N,N-diphenylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-isopropylmethyl Carbamoyl group, N,N-butylmethylcarbamoyl group, N-decylcarbamoyl group, N,N-decylmethylcarbamoyl group, N-undecylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N-dodecylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N-icosylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, One or two C1-C20 (preferably C1-C10) hydrocarbon groups, such as N,N-phenylmethylcarbamoyl group, and the group represented by the following formula, or its derivatized group (for example, a carboxy group , a carbamoyl group substituted with a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group);

Trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluoro All hydrogen atoms such as octyl group, perfluorononyl group, perfluorodecyl group, perfluorodecyl group, perfluorododecyl group, perfluoroicosyl group, perfluorocyclohexyl group and perfluorophenyl group a hydrocarbon group having 1 to 20 carbon atoms substituted with a fluorine atom;

Perfluoroethylmethyl group, perfluoropropylmethyl group, perfluoroisopropylmethyl group, perfluorobutylmethyl group, perfluoropentylmethyl group, perfluorohexylmethyl group, perfluoroheptylmethyl group, perfluorooctylmethyl group, purple A linear or branched chain having 1 to 20 carbon atoms in which all hydrogen atoms such as luoronylmethyl group, perfluorodecylmethyl group, perfluoroundecylmethyl group, perfluorododecylmethyl group and perfluoroicosylmethyl group are substituted with fluorine atoms a hydrocarbon group having 1 to 20 carbon atoms substituted with an alkyl group of;

Some of the hydrogen atoms such as 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group and 2,4,6-trifluorophenyl group are substituted with fluorine having 1 to 20 carbon atoms (preferably from 1 to 20 carbon atoms) The hydrocarbon group of 10);

-CO-SH, -CO-S-CH ₃ , -CO-S-CH ₂ CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₃ and -CO-S-CH ₂ -CH ₂ -CH ₂ a thiocarbonyl group bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as -CH ₃ , a thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms such as -CO-SC ₆ H ₅ ;

*-COCO-R represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those satisfying 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group (for example, a group derivatized with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) ) of the group;

*-NRCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivative thereof a group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.); The R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivative thereof a group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), etc.); The R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-NRCOOR represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octyl sulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OP(O)(OR) ₂ such as *-OP(O)(OCH ₃ ) ₂ (wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms (for example, the hydrocarbon group mentioned above) Those satisfying heavy carbon atoms of 1 to 20), or a derivatized group thereof (eg, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a chlorine atom) is a group derivatized with an octyl sulfamoyl group) or the like), and the R groups may be the same or different from each other, and may be bonded to each other to form a ring);

*-SiR ₃ (such as *-Si(CH ₃ ) ₃ , *-Si(CH ₂ CH ₃ ) ₃ , *-Si(C ₆ H ₅ ) ₃ and *-Si(CH(CH ₃ ) ₂ ) ₃ , etc. In the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (for example, a carboxy group or a sulfo group) , a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and R and may combine with each other to form a ring);

and the like.

Examples of the divalent substituent include an imino group substituted by an oxo group, a thioxo group, an imino group, an imino group substituted by an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted by an aryl group having 6 to 20 carbon atoms. can Examples of the imino group substituted by the alkyl group include CH ₃ -N=, CH ₃ -CH ₂ -N=, CH ₃ -(CH ₂ ) ₂ -N=, and CH ₃ -(CH ₂ ) ₃ -N=. there is. Examples of the imino group substituted by the aryl group include C ₆ H ₅ -N=.

As a substituent of a C1-C40 hydrocarbon group, Preferably, the substituent of group s1 is mentioned. The derivatized group shown below is preferably a group derivatized with a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) or the like. Do.

[group s1]

an oxy group in which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a carbonylamino group substituted with a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; halogen atom;

-CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms;

a hydrocarbon group having 1 to 20 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom; a hydrocarbon group having 1 to 20 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo.

As a substituent of a C1-C40 hydrocarbon group, More preferably, the substituent of group s2 is mentioned.

[group s2]

an oxy group in which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms;

sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof;

a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

hydroxyl group; a fluorine atom, a chlorine atom, a bromine atom;

-CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.);

-SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group;

a carbonyl-oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom; a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo.

As the hydrocarbon group having 1 to 40 carbon atoms having a substituent represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 , a monovalent or divalent substituent is and a hydrocarbon group having 1 to 40 carbon atoms, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms having a monovalent or divalent substituent, and 3 to 30 carbon atoms having a monovalent or divalent substituent. A saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group having 6 to 30 carbon atoms having a monovalent or divalent substituent, or a group combining hydrocarbon groups, and a group having 1 to 30 carbon atoms having a monovalent or divalent substituent;

More preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, and a carbon number having a substituent of group s1 It is a group combining 6-20 aromatic hydrocarbon groups or hydrocarbon groups, and a C1-C20 group which has a substituent of group s1 is mentioned,

Particularly preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, and a carbon number having a substituent of group s2 It is a group combining the aromatic hydrocarbon group or hydrocarbon group of 6-15, and the group of C1-C15 which has a substituent of group s2 is mentioned.

The heterocyclic group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 may be monocyclic or polycyclic, preferably heterocyclic as a component of the ring. It is a heterocycle containing atoms. As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned. The heterocyclic group preferably has 3 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, still more preferably 3 to 20 carbon atoms, still more preferably 3 to 18 carbon atoms, still more preferably 3 to 15, particularly preferably 3 to 14.

Examples of the heterocycle containing a nitrogen atom include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrroles such as 2,5-dimethylpyrrole, pyrazoles such as 2-methylpyrazole and 3-methylpyrazole, and 5-membered rings such as imidazole, 1,2,3-triazole and 1,2,4-triazole systemic unsaturated heterocycle;

pyrimidines such as pyridine, pyridazine and 6-methylpyrimidine; 6-membered ring unsaturated heterocycles such as pyrazine and 1,3,5-triazine;

Quinox such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline condensed bicyclic heterocycles such as saline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperizine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and the like.

Examples of the heterocycle containing an oxygen atom include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane. ; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; 5-membered ring unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran; Condensed bicyclic heterocycles, such as benzopyran, such as 1-benzofuran and 4-methylbenzopyran, benzodioxole, chroman, and isochroman; Condensed tricyclic heterocycles, such as xanthene and dibenzofuran; and the like.

As a heterocyclic ring containing a sulfur atom, 5-membered ring system saturated heterocycles, such as dithiolane;

6-membered ring-based saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl 1,3-dithiane;

5-membered ring unsaturated heterocycles, such as thiophene, such as 3-methylthiophene and 2-carboxythiophene, benzothiopyran, such as 4H-thiopyran and benzotetrahydrothiopyran;

Condensed bicyclic heterocycles, such as benzothiophene; condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.

Examples of the heterocycle containing a nitrogen atom and an oxygen atom include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone. Summons; Monocyclic unsaturated heterocycles, such as isoxazole, such as oxazole, such as 4-methyloxazole, 2-methylisoxazole, and 3-methylisoxazole;

Condensed bicyclic heterocyclic rings, such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline; condensed tricyclic heterocycles such as phenoxazine; and the like.

As a heterocyclic ring containing a nitrogen atom and a sulfur atom, Monocyclic heterocyclic rings, such as thiazole, such as 3-methylthiazole and 2, 4- dimethylthiazole; Condensed bicyclic heterocycles, such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine; and the like.

The said heterocyclic ring may be the group which combined the hydrocarbon groups mentioned above, and a tetrahydrofurylmethyl group etc. are mentioned.

In addition, the said heterocyclic ring may be represented by the following formula|equation.

The heterocyclic group may be a heterocyclic group formed by bonding two or more of R ^1Z2 to R ^5Z2 . Such a heterocyclic group has a ring structure of two or more rings together with the benzene ring to which R ^1Z2 to R ^5Z2 are bonded. As a ring structure of this two or more rings, the structure of the following formula is mentioned, for example.

The bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is removed.

The heterocyclic group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R O1Z2 , R ^{N1Z2 , R N2Z2 , R 1Z2 , R 2Z2 , R 3Z2 , R 4Z2 , R 5Z2 , R 101Z2 and R 102Z2 may have} . Moreover, when the said heterocyclic ring contains the nitrogen atom as its structural element, the hydrocarbon group mentioned above may couple|bond with this nitrogen atom as a substituent.

Preferred examples of the substituent include the same as preferred substituents which the hydrocarbon group represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 may have can Examples of the heterocyclic group having a substituent represented by R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 , R ^101Z2 and R ^102Z2 include a heterocyclic group having a monovalent or divalent substituent. and preferably a heterocyclic group having a substituent of group s1, more preferably a heterocyclic group having a substituent of group s2. The number of substituents (1st substituent) which the said hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents are mutually independent, and may be same or different. Moreover, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

Hereinafter, R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , R ^5Z2 of -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO-R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , a halogen atom, -SO ₃ M, and -CO ₂ M are demonstrated.

As -CO-R ^102Z2 , a formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the above formulas, such as a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxyl group, alcohol A carbonyl group (a group derivatized with an agar, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) In the case, the number of carbon atoms is 2 to 41) and the group corresponding to -CO-R ^102Z2 in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2, preferably having 1 to 11 carbon atoms (more Preferably, a hydrocarbon group having 1 to 10 carbon atoms or a carbonyl group to which a derivatized group thereof is bonded (when the carbonyl group is an alkanoyl group, the carbon number is more preferably 2 to 12) and Tables 1Z2 to 22Z2 and Tables 27Z2 to Tables In the compound represented by 37Z2, the group corresponding to -CO-R ^102Z2 , etc. are mentioned.

-COO-R ^101Z2 is a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, Octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, etc. 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) In the compound shown in Tables 1Z2 to Table 22Z2 and Table 27Z2 to Table 37Z2, and the group corresponding to -COO-R ^101Z2 in the group corresponding to -COO-R ^101Z2 , the group corresponding to -COO-R 101Z2, etc. and preferably an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded, and a group corresponding to -COO-R ^101Z2 in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2. can

As -OCO-R ^102Z2 , a formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, etc., and groups represented by the above formulas having 1 to 40 carbon atoms (preferably from 1 to carbon atoms). 20) of a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) A carbonyloxy group to which a group derivatized with, etc.) is bonded (when the carbonyloxy group is an acyloxy group, it has 2 to 41 carbon atoms)

and groups corresponding to -OCO-R ^102Z2 in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2, preferably having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms). A carbonyloxy group to which a hydrocarbon group or a derivatized group thereof is bonded (when the carbonyloxy group is an acyloxy group, more preferably 2 to 12 carbon atoms), and compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2 and groups corresponding to -OCO-R ^102Z2 .

-COCO-R ^102Z2 is methyloxalyl group, ethyloxalyl group, propyloxalyl group, butyloxalyl group, pentyloxalyl group, hexyloxalyl group, (2-ethyl)hexyloxalyl group, heptyloxalyl group group, octyloxalyl group, nonyloxalyl group, decyloxalyl group, undecyloxalyl group, dodecyloxalyl group, icosyloxalyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p - a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, Halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. bonded oxalyl group and Tables 1Z2 to 2 2Z2 and Tables 27Z2 to Tables In the compound represented by 37Z2, the group corresponding to -COCO-R ^102Z2 , etc. are mentioned.

Examples of the -OR ^102Z2 group include a hydroxy group; Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group Group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2 ,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyl group Oxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyl Oxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-e A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof, such as a oxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, and a group represented by the above formula A group (for example, a group derivatized with a carboxy group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) oxy groups and groups corresponding to -OR ^102Z2 in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2, preferably an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; The group corresponding to -OR ^102Z2 in the compound shown in Table 1Z2 - Table 22Z2 and Table 27Z2 - Table 37Z2, etc. are mentioned.

As -SO ₂ -R ^101Z2 , a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl)hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonyl group sulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc. A hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof (carboxy group, sulfo group, nitro group, hydroxy group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) In the compounds shown in the sulfonyl group and Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2, the group corresponding to -SO ₂ -R ^101Z2 ) to which a group derivatized with a sulfonyl group) is bonded, and the like, preferably having 1 to 10 carbon atoms. and a group corresponding to -SO ₂ -R ^101Z2 in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2 and a sulfonyl group to which a hydrocarbon group or a derivatized group thereof is bonded.

As -SO ₂ N(R ^102Z2 ) ₂ , a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfa Moyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A sulfamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z2 to 22Z2 and a group corresponding to -SO ₂ NH(R ^102Z2X ) (R ^102Z2X is the same as R ^102Z2 except that it does not form a hydrogen atom) in the compounds shown in Tables 27Z2 to 37Z2; N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-dipropylsulfamoyl group, N ,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-disec -Butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group, N,N-dipentylsulfamoyl group, N, N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N,N-diheptylsulfamoyl group, N, N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decylmethylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N ,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, N,N-diphenylsulfamoyl group, etc., and groups represented by the above formulas, etc. of two C1 to C40 (preferably C1 to C20) hydrocarbon groups or derivatized groups thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), 1 to 10 carbon atoms) _A sulfamoyl group substituted with an alkylsulfamoyl group (preferably a group derivatized with an ^{octylsulfamoyl} group), etc. of ) ₂ (provided that R ^102Z2X is the same as R ^102Z2 except that it does not become a hydrogen atom);

-SO ₂ N(R ^102Z2 ) ₂ in a sulfamoyl group substituted with preferably 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof and in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2 and groups corresponding to .

-CON(R ^102Z2 ) ₂ is a carbamoyl group; N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarp Bamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group and N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z2 to 22Z2 and a group corresponding to -CONH(R ^102Z2X ) (provided that R ^102Z2X is the same as R ^102Z2 except that it does not form a hydrogen atom) in the compounds shown in Tables 27Z2 to 37Z2;

N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N ,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec -Butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-dibutylcarbamoyl group, N,N-butyloctylcarbamoyl group, N, N-dipentylcarbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N,N-dihexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N, N-diheptylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N,N-decylmethylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-phenylmethylcarbamoyl group and N,N-diphenylcarbamoyl group and two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably preferably a chlorine atom), a carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), and the like shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2 and groups corresponding to -CON(R ^102Z2X ) ₂ (provided that R ^102Z2X is the same as R ^102Z2 except that it does not become a hydrogen atom) in the compound;

Preferably, in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2 and a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, -CON(R ^102Z2 ) ₂ Corresponds to and the like.

-N(R ^102Z2 ) ₂ is an amino group;

N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group , N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, N-dodecylamino group, N- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as an icosylamino group, N-phenylamino group, and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, An amino group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z2 to 22Z2 and Tables a group corresponding to -NH(R ^102Z2X ) (provided that R ^102Z2X is the same as R ^102Z2 except that it does not form a hydrogen atom) in the compounds shown in 27Z2 to Table 37Z2;

N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N, N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N-diisobutylamino group, N,N-disec-butylamino group, N,N-ditert-butylamino group, N,N- Butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, N,N-di(1-ethylpropyl)amino group, N,N-dihexylamino group, N,N-di(2-ethyl) ) hexylamino group, N,N-diheptylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N,N-decylmethylamino group, N,N-undecylmethylamino group, N,N-dode A sylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc., and groups represented by the above formulas, such as groups having 1 to 40 carbon atoms (preferably carbon atoms) 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) -N(R ^102Z2X ) ₂ (provided that R ^102Z2X is not a hydrogen atom, except that -N(R 102Z2X ) 2 in the compound shown in the amino group and Table 1Z2 to Table 22Z2 and Table 27Z2 to Table 37Z2) and a group corresponding to R ^102Z2 );

Preferably, in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2 and an amino group substituted with one or two C1 to C10 hydrocarbon groups or derivatized groups thereof, a group corresponding to -N(R ^102Z2 ) ₂ and the like.

-NHCO-R ^{102Z2 is} a formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as amino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group, and groups represented by the above formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. group) to which the carbonylamino group is bonded (when the carbonylamino group is an acylamino group, it has 1 to 40 carbon atoms) and -NHCO-R ^102Z2 in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2 such as to do,

Preferably, a carbonylamino group having 1 to 10 carbon atoms or a derivatized group thereof bonded thereto (when the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10) and Tables 1Z2 to 22Z2 and Tables In the compound shown in 27Z2 - Table 37Z2, the group corresponding to -NHCO-R ^102Z2 , etc. are mentioned.

Examples of -NHCON(R ^102Z2 ) ₂ include the groups listed above, and groups corresponding to -NHCON(R ^102Z2 ) ₂ in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2.

Examples of -NHCOOR ^102Z2 include the groups listed above and groups corresponding to -NHCOOR ^102Z2 in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2.

Examples of -OCON(R ^102Z2 ) ₂ include the groups listed above, and groups corresponding to -OCON(R ^102Z2 ) ₂ in the compounds shown in Tables 1Z2 to 22Z2 and Tables 27Z2 to 37Z2.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are preferable.

As M of -SO ₃ M and -CO ₂ M, a hydrogen atom; Alkali metal atoms, such as a lithium atom, a sodium atom, and a potassium atom, are mentioned, Preferably, a hydrogen atom, a sodium atom, and a potassium atom are mentioned.

The -CO-R ^102Z2 , -COO-R ^102Z2 , -OCO-R ^102Z2 , -COCO-R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^102Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCON(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ Substituents (first substituents) included in 2 are, Or two or more may be sufficient, and two or more substituents are mutually independent, and may be same or different.

In addition, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

The ring formed by R ^2Z2 and R ^3Z2 , R ^3Z2 and R ^4Z2 , and R ^4Z2 and R ^5Z2 is condensed with the benzene ring of the isoindoline skeleton of the compound represented by formula IZ2. Examples of the condensed ring structure of the benzene ring and the ring formed by R ^2Z2 and R ^3Z2 , R ^3Z2 and R ^4Z2 , and R ^4Z2 and R ^5Z2 include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, and phenylene. nalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, N-methylphthalimide, N-(1-phenylethyl)phthalimide and tetracene hydrocarbon-based condensed ring structures and partial reduction products thereof (eg, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); Indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, perimidine, phenanthroline and phenazine, etc. of nitrogen-containing condensed heterocycles and partial reduction products thereof; and oxygen-containing condensed heterocycles such as 3-hydrobenzofuran 2-one, and partially reduced products thereof.

When R ^2Z2 and R ^3Z2 , R ^3Z2 and R ^4Z2 , and R ^4Z2 and R ^5Z2 form a ring, the ring may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R O1Z2 , R ^{N1Z2 , R N2Z2 , R 1Z2 , R 2Z2 , R 3Z2 , R 4Z2 , R 5Z2 , R 101Z2 and R 102Z2 may have} . Preferred examples of the substituent include the same as preferred substituents that the hydrocarbon group represented by R ^{O1Z2 , R N1Z2 , R N2Z2 , R 1Z2 , R 2Z2 , R 3Z2 , R 4Z2 , R 5Z2 , R 101Z2 and R 102Z2 may have .} can

When R ^3Z2 and R ^4Z2 form a ring, it is preferable that R ^2Z2 and R ^5Z2 are each independently a hydrogen atom, an amino group and a hydroxyl group.

When R ^2Z2 and R ^3Z2 form a ring, R ^4Z2 and R ^5Z2 preferably do not form a ring, and more preferably R ^4Z2 and R ^5Z2 are hydrogen atoms.

When R ^4Z2 and R ^5Z2 form a ring, R ^2Z2 and R ^3Z2 preferably do not form a ring, and more preferably R ^2Z2 and R ^3Z2 are hydrogen atoms. R ^1Z2 is preferably a hydrogen atom. R ^O1Z2 is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, even if it has a hydrogen atom or a substituent It is more preferably a hydrocarbon group having 1 to 15 carbon atoms, particularly preferably a hydrocarbon group having 1 to 10 carbon atoms which may have a hydrogen atom or a substituent, and particularly preferably a hydrocarbon group having 1 to 5 carbon atoms or a hydrocarbon group which may have a hydrogen atom or a substituent. more preferably, a hydrogen atom, a methyl group, or an ethyl group is particularly preferable.

R ^N1Z2 and R ^N2Z2 are hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -CO ₂ M or carbon number 1 which may have a substituent It is preferably a hydrocarbon group of -40, more preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, hydrogen It is especially preferable that it is a C1-C15 hydrocarbon group which may have an atom or a substituent, It is especially more preferable that it is a C1-C10 hydrocarbon group which may have a hydrogen atom or a substituent, It is a C1 which may have a hydrogen atom or a substituent. It is especially preferable that it is a hydrocarbon group of -6 or a hydrocarbon group of 1 to 5 carbon atoms which may have a substituent, particularly preferably a hydrogen atom, a methyl group, an ethyl group, or a phenyl group, and most preferably a hydrogen atom, a methyl group, or an ethyl group Do. In addition, although R ^N1Z2 and R ^N2Z2 may be the same group or different groups, they are preferably the same group.

From the viewpoint that the phase difference value of the color filter formed from the coloring composition becomes small, at least one of R ^{2Z2 , R 3Z2 ,} R ^4Z2 , and R ^5Z2 is -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO-R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , - NHCO-N(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, optionally having 1 to 40 carbon atoms It is preferable that it is a hydrocarbon group or a heterocyclic group which may have a substituent, and all or part of a C1-C40 hydrocarbon group which may have a substituent, a halogen atom, -N(R ^102Z2 ) ₂ , a nitro group, and a hydrogen atom is fluorine A hydrocarbon group having 1 to 20 atoms substituted with a hydrocarbon group, -NHCO-R ^102Z2 , -OR ^102Z2 , -SO ₃ M or -CO ₂ M is more preferable, and a hydrocarbon group having 1 to 40 carbon atoms which may have a nitro group or a substituent It is more preferably a group, and even more preferably a nitro group or a tert-butyl group. Alternatively, at least one set of R ^2Z2 and R ^3Z2 , R ^3Z2 and R ^4Z2 , or R ^4Z2 and R ^5Z2 preferably forms a ring.

From a viewpoint that the retardation value of the color filter formed from the coloring composition becomes small, a C1-C40 hydrocarbon group which at least one of ^{R2Z2, R3Z2 , R4Z2} , ^R5Z2 may have a substituent, a halogen atom, -N (R ^102Z2 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z2 , -OR ^102Z2 , -SO ₃ M or -CO ₂ M is preferable. and a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Among them, R ^3Z2 is a nitro group or a tert-butyl group and R ^2Z2 , R ^4Z2 and R ^5Z2 are a hydrogen atom, or R ^2Z2 , R ^3Z2 and R ^5Z2 are a hydrogen atom and R ^4Z2 is a nitro group or tert-butyl It is more preferable to be a group.

The compound IZ2 is preferably a compound represented by the formula IZ2-B (hereinafter, sometimes referred to as compound IZ2-B). When compound IZ2 is compound IZ2-B, the phase difference value of the color filter formed from the coloring composition containing compound IZ2-B becomes smaller.

[In formula IZ2-B, R ^CO11Z2 and R ^CO21Z2 independently represent -OR ^O1Z2 or -NR ^N1Z2 R ^N2Z2 , and at least one of R ^CO11Z2 and R ^CO21Z2 is -NR ^N1Z2 R ^N2Z2 .

R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^21Z2 , R ^31Z2 , R ^41Z2 , R ^51Z2 are, independently of each other, a hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO- R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N (R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or represents a heterocyclic group which may have a substituent, R ^21Z2 and R ^31Z2 , R ^31Z2 and R ^41Z2 , and R ^41Z2 and R ^51Z2 may be bonded to each other to form a ring, R ^21Z2 , R ^31Z2 , R ^41Z2 and R At least one of ^51Z2 is -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO-R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , halogen atom, cyano group , nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R ^21Z2 and R ^31Z2 , R ^31Z2 and R ^41Z2 , and At least one set of R ^41Z2 and R ^51Z2 is bonded to form a ring.

R ^101Z2 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^O1Z2 and R ^102Z2 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom.

When two or more R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^101Z2 , R ^102Z2 and M exist, they may be the same or different. The broken line indicates the E or Z body.]

In formula IZ2-B, R ^CO11Z2 , R ^CO21Z2 , R ^21Z2 , R ^31Z2 , R ^41Z2 and R ^51Z2 include the same ones as R ^CO1Z2 , R CO2Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , and R ^5Z2 in formula ^IZ2 can

Preferred R ^CO11Z2 , R ^CO21Z2 , R ^21Z2 , R ^31Z2 , R ^41Z2 and R ^51Z2 in formula IZ2-B are those of R ^CO1Z2 , R ^CO2Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , and R ^5Z2 in formula IZ2 preferred the same can be mentioned.

From the viewpoint of synthesis easiness, in formula IZ2-B, R ^1Z2 is preferably a hydrogen atom.

In formula IZ2-B, R ^O1Z2 is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, hydrogen It is more preferably a C1-C15 hydrocarbon group which may have an atom or a substituent, It is especially preferable that it is a C1-C10 hydrocarbon group which may have a hydrogen atom or a substituent, It is a C1-C15 which may have a hydrogen atom or a substituent. It is especially more preferable that it is a hydrocarbon group of 5, and it is especially preferable that it is a hydrogen atom, a methyl group, or an ethyl group.

R ^N1Z2 and R ^N2Z2 are hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -CO ₂ M or carbon number 1 which may have a substituent It is preferably a hydrocarbon group of -40, more preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, hydrogen It is especially preferable that it is a C1-C15 hydrocarbon group which may have an atom or a substituent, It is especially more preferable that it is a C1-C10 hydrocarbon group which may have a hydrogen atom or a substituent, It is a C1 which may have a hydrogen atom or a substituent. It is especially preferable that it is a hydrocarbon group of -6 or a hydrocarbon group of 1 to 5 carbon atoms which may have a substituent, more particularly preferably a hydrogen atom, a methyl group, an ethyl group, or a phenyl group, and most preferably a hydrogen atom, a methyl group, or an ethyl group Do. In addition, although R ^N1Z2 and R ^N2Z2 may be the same group or different groups, they are preferably the same group.

At least one of R ^21Z2 , R ^31Z2 , R ^41Z2 , and R ^51Z2 in formula IZ2-B from the viewpoint that the retardation value of the color filter formed from the coloring composition becomes small is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent , a halogen atom, -N(R ^102Z2 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of a hydrogen atom is substituted with a fluorine atom, -NHCO-R ^102Z2 , -OR ^102Z2 , -SO ₃ M or - It is preferred that it is CO ₂ M,

It is more preferable that it is a C1-C40 hydrocarbon group which may have a nitro group or a substituent, and it is still more preferable that it is a nitro group or a tert- butyl group. Among them, R ^31Z2 is a nitro group or tert-butyl group and R ^21Z2 , R ^41Z2 and R ^51Z2 are a hydrogen atom, or R ^21Z2 , R ^31Z2 and R ^51Z2 are a hydrogen atom and R ^41Z2 is a nitro group or tert-butyl It is more preferable to be a group.

As a specific example of compound IZ2, for example,

In the formula IaZ2, the compound IaZ2-1 to the compound IaZ2-494 having a substituent shown in Table 1Z2, Table 2Z2, Table 3Z2, Table 4Z2, Table 5Z2, Table 6Z2, Table 27Z2, Table 28Z2, Table 29Z2 and Table 30Z2 or alkali metal salts;

For Formula IbZ2, in Table 7Z2, Table 8Z2, Table 9Z2, Table 10Z2, Table 11Z2, Table 12Z2, Table 13Z2, Table 14Z2, Table 31Z2, Table 32Z2, Table 33Z2, Table 34Z2, Table 35Z2, Table 36Z2 and Table 37Z2 Compounds IbZ2-1 to IbZ2-840 or alkali metal salts thereof having the substituents shown;

In formula IcZ2, compound IcZ2-1 to compound IcZ2-296 or an alkali metal salt thereof having a substituent shown in Table 15Z2, Table 16Z2, Table 17Z2, Table 18Z2, Table 19Z2, Table 20Z2, Table 21Z2, and Table 22Z2 are listed, respectively can

B ^a1Z2 B ^a2Z2 is a formula (BB1) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1), a formula (BBO8), a formula (BBO10) , any partial structure represented by the formulas (BBD1) and (BBJ2) is shown. Formula (BB1) to Formula (BB60), Formula (BBK2), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), Formula (BBO8), Formula (BBO10), Formula (BBD1) and Formula (BBJ2) is (BB1) to ( ^BB60 ), Formula ( ^BBK2 ), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), It is equivalent to formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2). B ^a1Z2 and B ^a2Z2 each represent a bond, and B ^a1Z2 is a formula (BB1) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1) , B ^a2Z2 is a bond of B ² when it is a bond of B ¹ in formulas (BBO8), (BBO10), (BBD1) and (BBJ2), B ^a1Z2 is a bond of formulas (BB1) to (BB60) ), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) ^of B2 In the case of a bond, B ^a2Z2 becomes a bond of B ¹ .

As B ^a1Z2 B ^a2Z2 , Formula (BB1), Formula (BB6), Formula (BB8), Formula (BB11), Formula (BB14), Formula (BB19), Formula (BB37), Formula (BB58), Formula (BBJ2) , the formulas (BBO8) and (BBO10) are preferable, and the formulas (BB1), (BB6) and (BB19) are more preferable.

Table 1Z2, Table 2Z2, Table 3Z2, Table 4Z2, Table 5Z2, Table 6Z2, Table 7Z2, Table 8Z2, Table 9Z2, Table 10Z2, Table 11Z2, Table 12Z2, Table 13Z2, Table 14Z2, Table 15Z2, Table 16Z2, Table 17Z2 , Table 18Z2, Table 19Z2, Table 20Z2, Table 21Z2, Table 22Z2, Table 27Z2, Table 28Z2, Table 29Z2, Table 30Z2, Table 31Z2, Table 32Z2, Table 33Z2, Table 34Z2, Table 35Z2, Table 36Z2, and Table 37Z2 Symbols show the following partial structures. In addition, in the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ"" represents a benzyl group, "NPR" represents a propyl group, "IPR" represents an isopropyl group, "IBu" represents an isobutyl group, "EOE" represents -CH ₂ CH ₂ OCH ₂ CH ₃ , "ALL " represents an allyl group, "HYE" represents a 2-hydroxyethyl group, "COM" represents -CO-CH ₃ , "COE" represents -COO-CH ₂ CH ₃ , and "CBA" represents -CO 2H is represented, "CBM" represents -CONH2 _, "NH2" represents -NH2 _, * represents _a bond.

In the table, partial structures represented by the following formulas are indicated by symbols.

[Table 1Z2]

[Table 2Z2]

[Table 3Z2]

[Table 4Z2]

[Table 5Z2]

[Table 6Z2]

[Table 7Z2]

[Table 8Z2]

[Table 9Z2]

[Table 10Z2]

[Table 11Z2]

[Table 12Z2]

[Table 13Z2]

[Table 14Z2]

[Table 15Z2]

[Table 16Z2]

[Table 17Z2]

[Table 18Z2]

[Table 19Z2]

[Table 20Z2]

[Table 21Z2]

[Table 22Z2]

[Table 27Z2]

[Table 28Z2]

[Table 29Z2]

[Table 30Z2]

[Table 31Z2]

[Table 32Z2]

[Table 33Z2]

[Table 34Z2]

[Table 35Z2]

[Table 36Z2]

[Table 37Z2]

For example, the compound IaZ2-1 is a compound represented by the formula IaZ2-1.

Compound IaZ2-1 to Compound IaZ2-165, Compound IbZ2-223 to Compound IbZ2-494, Compound IbZ2-1 to Compound IbZ2-248, Compound IbZ2-311 to Compound IbZ2-840, Compound IcZ2-1 to Compound IcZ2-234 Preferably, compound IaZ2-1 to compound IaZ2-165, compound IaZ2-223 to compound IaZ2-436, compound IbZ2-1 to compound IbZ2-248, compound IbZ2-311 to compound IbZ2-782, compound IcZ2-1 to compound IcZ2 -234 is more preferable,

Compound IaZ2-1 to compound IaZ2-165, compound IbZ2-1 to compound IbZ2-248, and compound IcZ2-1 to compound IcZ2-234 are more preferred, and compound IaZ2-1 to compound IaZ2-111, compound IbZ2-1 to Compound IbZ2-248 and compound IcZ2-1 to compound IcZ2-234 are even more preferred, and compound IaZ2-1 to compound IaZ2-54 and compound IbZ2-1 to compound IbZ2-186 are particularly preferred.

Specific examples of compound IZ2 include Table 1Z2, Table 2Z2, Table 3Z2, Table 4Z2, Table 5Z2, Table 6Z2, Table 7Z2, Table 8Z2, Table 9Z2, Table 10Z2, Table 11Z2, Table 12Z2, Table 13Z2, Table 14Z2, Table 15Z2 , Table 16Z2, Table 17Z2, Table 18Z2, Table 19Z2, Table 20Z2, Table 21Z2, Table 22Z2, Table 27Z2, Table 28Z2, Table 29Z2, Table 30Z2, Table 31Z2, Table 32Z2, Table 33Z2, Table 34Z2, Table 35Z2, Table In the compounds shown in 36Z2 and Table 37Z2, compounds in which 1 to 3 hydrogen atoms contained in the compound are substituted with -SO ₃ M or -CO ₂ M are also exemplified. For example, a compound in which 1 to 3 sulfo groups are bonded to compound IaZ2-1 of Table 1Z2 is represented by the following structure. However, in the formula, -(SO ₃ H) shall mean that any hydrogen atom of the compound IaZ2-1 of Table 1Z2 is substituted.

To compound IaZ2-1 to compound IaZ2-165, compound IaZ2-223 to compound IaZ2-494, compound IbZ2-1 to compound IbZ2-248, compound IbZ2-311 to compound IbZ2-840, compound IcZ2-1 to compound IcZ2-234 , a compound in which 1 to 3 -SO ₃ M or -CO ₂ M is bonded is preferred,

To compound IaZ2-1 to compound IaZ2-165, compound IaZ2-223 to compound IaZ2-436, compound IbZ2-1 to compound IbZ2-248, compound IbZ2-311 to compound IbZ2-782, compound IcZ2-1 to compound IcZ2-234 , a compound in which 1 to 3 -SO ₃ M or -CO ₂ M is bonded is more preferable,

Compounds in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded to Compound IaZ2-1 to Compound IaZ2-165, Compound IbZ2-1 to Compound IbZ2-248, and Compound IcZ2-1 to Compound IcZ2-234 preferably,

Compound IaZ2-1 to compound IaZ2-111, compound IbZ2-1 to compound IbZ2-248, and compound IcZ2-1 to compound IcZ2-234 are more preferably compounds in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded. more preferably,

Compounds in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded to compound IaZ2-1 to compound IaZ2-54 and compound IbZ2-1 to compound IbZ2-186 are particularly preferred.

As the compound to which -CO ₂ M is bound, compound IbZ2-2, compound IbZ2-3, compound IbZ2-4, compound IbZ2-12, compound IbZ2-126, compound IbZ2-127, compound IbZ2-687, compound IbZ2-370, etc. Compounds in which two -CO ₂ H are bonded, in particular compound IbZ2-317, compound IbZ2-318, compound IbZ2-319, compound IbZ2-320, compound IbZ2-515, compound IbZ2-516, compound IbZ2-706, compound IbZ2- 389 and the like are particularly preferred.

As the compound (IZ2), in the formula (IZ2), R ^CO1Z2 and R ^CO1Z2 are the same group, and R ^O1Z2 is a hydrogen atom or a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M; may be a hydrocarbon group having 1 to 20 carbon atoms, and R ^N1Z2 and R ^N2Z2 are each independently a hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -CON(R ^102Z2 ) ₂ , or -SO ₃ M and a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -CO ₂ M, and R ^1Z2 is a hydrogen atom, -SO ₃ M and -CO ₂ M having a substituent selected from the group consisting of may be a hydrocarbon group having 1 to 20 carbon atoms, -SO ₃ M or -CO ₂ M, and R ^2Z2 to R ^5Z2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N ( R ^102Z2 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z2 , -OR ^102Z2 , -SO ₃ M or -CO ₂ M, and R ^102Z2 is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

R ^101Z2 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, M is preferably a compound in which a hydrogen atom or an alkali metal atom;

R ^CO1Z2 and R ^CO1Z2 are the same group, R ^O1Z2 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, R ^N1Z2 and R ^N2Z2 are, independently of each other, a hydrogen atom, -CO-R ^102Z2 , -CON(R ^102Z2 ) ₂ , or -SO ₃ M and -CO ₂ M C 1 - 10 is a hydrocarbon group, R ^1Z2 is a hydrogen atom, R ^2Z2 to R ^5Z2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102Z2 ) ₂ , a nitro group , a hydrocarbon group having 1 to 10 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z2 , -OR ^102Z2 , -SO ₃ M or -CO ₂ M, R ^102Z2 is a hydrogen atom, or - It is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of SO ₃ M and -CO ₂ M, R ^101Z2 has a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M It is a hydrocarbon group having 1 to 10 carbon atoms which may be present, and M is more preferably a hydrogen atom or an alkali metal atom;

R ^CO1Z2 and R ^CO1Z2 are the same group, R ^O1Z2 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, R ^N1Z2 and R ^N2Z2 are, independently of each other, a hydrogen atom, -CO-R ^102Z2 , -CON(R ^102Z2 ) ₂ , or -SO ₃ M and -CO ₂ M C 1 - 10 is a hydrocarbon group, R ^1Z2 is a hydrogen atom, R ^2Z2 to R ^5Z2 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102Z2 ) ₂ , a nitro group , trifluoromethyl group, -OR ^102Z2 , -SO ₃ M or -CO ₂ M , R ^102Z2 is a hydrogen atom or a carbon number that may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M It is a hydrocarbon group of 1-10, R ^101Z2 is a C1-C10 hydrocarbon group which may have a substituent selected from the group which consists of -SO ₃ M and -CO ₂ M, M is a hydrogen atom or an alkali metal atom A phosphorus compound is more preferred.

In the compound IZ2, when R ^1Z2 is a hydrogen atom, a compound represented by the formula pt1Z2 (hereinafter sometimes referred to as a phthalonitrile compound) is reacted with a compound represented by the formula pt2Z2 (hereinafter sometimes referred to as an alkoxide compound) After the reaction, it can be prepared by further reacting the compound represented by the formula pt3Z2 with the compound represented by the formula pt4Z2 in the presence of an acid. Further, when R ^1Z2 is other than a hydrogen atom, compound IZ2 can be produced by further reacting with a compound represented by the formula pt5Z2.

[In formula pt1Z2, formula pt2Z2, formula pt3Z2, formula pt4Z2, formula pt5Z2, and formula IZ2, R ^CO1Z2 , R ^CO2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 and R ^5Z2 have the same meanings as above. R ^14Z2 represents an alkyl group having 1 to 20 carbon atoms. M ^1Z2 represents an alkali metal atom.

LG represents a halogen atom, a methanesulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group.]

Examples of the C1-C20 alkyl group represented by R ^14Z2 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group, and preferably a C1 group. -6 alkyl groups are mentioned.

Examples of the alkali metal atom represented by M ^1Z2 include a lithium atom, a sodium atom and a potassium atom.

The usage-amount of an alkoxide compound is 0.1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 0.2-5 mol, More preferably, it is 0.3-3 mol, More preferably, it is 0.4-2 mol. it's a mall

The amount of the compound pt3Z2 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 2 moles, with respect to 1 mole of the phthalonitrile compound. am.

The usage-amount of compound pt4Z2 is 1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 1-5 mol, More preferably, it is 1-3 mol, More preferably, it is 1-2 mol. am. Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; and carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid. These are mentioned, More preferably, acetic acid is mentioned.

The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, still more preferably 1 to 6 moles with respect to 1 mole of the phthalonitrile compound. The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z2, and the compound pt4Z2 is usually carried out in the presence of a solvent.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N ,N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide are mentioned, and more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1- octanol, acetone, methylene chloride, chloroform, N,N-dimethylformaldehyde, N-methylpyrrolidone and dimethyl sulfoxide are exemplified, particularly preferably water, acetonitrile, methanol, ethanol and 2-propanol. can be heard

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of phthalonitrile compounds.

Reaction temperature is 0-200 degreeC normally, Preferably it is 0-100 degreeC, More preferably, it is 0-70 degreeC, More preferably, it is 0-50 degreeC. Reaction time is 0.5 to 300 hours normally.

The amount of compound pt5Z2 to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 mole to 1 mole of compound IZ2 in which R ^1Z2 is a hydrogen atom. 1 to 2 moles.

When the compound pt5Z2 is reacted, it is preferable that a base coexist. Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; organometallic compounds such as butyllithium, tert-butyllithium and phenyllithium; Inorganic bases, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, are mentioned.

The amount of the base used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 10 moles with respect to 1 mole of compound IZ2 in which R ^1Z2 is a hydrogen atom. 2 moles.

The reaction of the compound pt5Z2 is usually carried out in the presence of a solvent. A solvent can be selected from the range similar to the above.

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of compound IZ2 whose R ^<1Z2> is a hydrogen atom. The reaction temperature of the compound pt5Z2 is usually -90 to 200°C, preferably -80 to 100°C, and more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

When compound IZ2 does not have a sulfo group or -SO ₃ M ²² , a sulfo group or -SO ₃ M ² can be introduced by reacting compound IZ2 with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid.

M ²² represents an alkali metal atom.

Examples of the alkali metal atom represented by M ²² include a lithium atom, a sodium atom and a potassium atom.

The amount of SO ₃ used in the fuming sulfuric acid is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, still more preferably 5 to 25 moles, with respect to 1 mole of compound IZ2. am.

The amount of sulfuric acid used in the fuming sulfuric acid is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles with respect to 1 mole of compound IZ2. .

The usage-amount of chlorosulfonic acid is 1-500 mol normally with respect to 1 mol of compound IZ2, Preferably it is 10-300 mol, More preferably, it is 10-200 mol, More preferably, it is 10-150 mol.

The reaction temperature for sulfonation is usually -20 to 200°C, preferably -10 to 100°C, and more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

The method for taking out the compound IZ2 from the reaction mixture is not particularly limited, and can be taken out by various known methods. For example, after completion of the reaction, the compound IZ2 can be extracted by filtering the reaction mixture. After filtration, the obtained residue may be subjected to column chromatography, recrystallization, or the like. After completion of the reaction, the solvent of the reaction mixture may be distilled off, and then purified by column chromatography.

<Compound IZ3>

Compound IZ3 is a compound represented by Formula (IZ3).

[In formula IZ3, R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , and R ^7Z3 are, independently of each other, a hydrogen atom, -CO-R ^102Z3 , -COO-R ^101Z3 , -OCO- R ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , -SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, optionally substituted carbon number 1 to 40 hydrocarbon group or heterocyclic group which may have a substituent. R ^2Z3 and R ^3Z3 , R ^3Z3 and R ^4Z3 , and R ^4Z3 and R ^5Z3 may be respectively bonded to each other to form a ring. R ^101Z3 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z3 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^101Z3 , R ^102Z3 and M exist, they may be same or different. The broken line indicates the E or Z body.]

The number of carbon atoms in the hydrocarbon group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 is 1 to 40, preferably 1 to 30, more preferably is 1 to 20, more preferably 1 to 15, particularly preferably 1 to 10.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group , may be saturated or unsaturated, or may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, straight-chain alkyl groups such as a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a heptadecyl group, an octadecyl group, and an icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl)pentyl group, (2- methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group and (3-ethyl) heptyl group branched chain alkyl groups and the like; Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-pro alkenyl groups such as phenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl; and the like. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, still more preferably is 1 to 8, particularly preferably 1 to 5. Especially, it is especially preferable that it is a C1-C10, More preferably, it is a C1-C8 linear or branched alkyl group, and a methyl group, an ethyl group, and a tert- butyl group are especially preferable.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl 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, Cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group; cycloalkyl groups such as a 4-octylcyclohexyl group and a 4-cyclohexylcyclohexyl group; Cycloalkenyl groups, such as a cyclohexenyl group (For example, cyclohexa-2-ene, cyclohexa-3-ene), a cycloheptenyl group, and a cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane, etc. are mentioned. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 4 to 20 carbon atoms, still more preferably 4 to 15 carbon atoms, and particularly More preferably, it is 5-15, Most preferably, it is 5-10. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

Examples of the aromatic hydrocarbon group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl 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, 4-vinylphenyl group, o-iso Propylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 4-ethylphenyl group, 4-butylphenyl group, 4 -pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-vinylphenyl group, 1-naphthyl group, 2-naphthyl group , 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group and aromatic groups such as anthryl group and pyrenyl group hydrocarbon group; and the like. Carbon number of an aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-15.

The hydrocarbon group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 is the above-mentioned hydrocarbon group (for example, an aromatic hydrocarbon group, a chain hydrocarbon group and an alicyclic group). At least one of the formula hydrocarbon groups) may be combined, and may be an aralkyl group such as a benzyl group, a phenethyl group, or a 1-methyl-1-phenylethyl group; Arylalkenyl groups, such as a phenylethenyl group (phenylvinyl group); Arylalkynyl groups, such as a phenylethynyl group; a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; A cyclohexylmethylphenyl group, a benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. are mentioned.

The group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 is a combination of the above hydrocarbon groups (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group). As the group, for example, cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexylethyl group, adamantyl group The alkyl group to which one or more alicyclic hydrocarbon groups, such as a methyl group, couple|bonded may be sufficient.

These carbon number becomes like this. Preferably it is 4-30, More preferably, it is 6-30, More preferably, it is 6-20, More preferably, it is 4-20, More preferably, it is 4-15, Especially Preferably it is 6-15.

The hydrocarbon group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 may have a substituent. The substituent may be monovalent or divalent. The divalent substituent preferably has two bonds bonded to the same carbon atom to form a double bond.

Examples of the monovalent substituent include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, (2-ethyl ) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1 -Methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6 -Dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyano group Phenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyloxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group Group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group, etc., and groups represented by the following formulas A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an oxy group in which an alkylsulfamoyl group (preferably a group derivatized with an octylsulfamoyl group) or the like) is bonded to one side;

Methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethyl)hexylthio group, heptylthio group, octylthio group, nonylthio group , a sulfanyl group to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as decylthio group, undecylthio group, dodecylthio group, icosylthio group, phenylthio group, and o-tolylthio group;

an epoxy group, an oxetanyl group, a tetrahydrofuryl group, a tetrahydropyranyl group;

formyl group;

Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the following formulas, such as a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivatized group thereof (for example, a carboxy group , a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) When it is set as a canoyl group, carbon number becomes like this. Preferably it is 2-12);

Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group , decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, icosyloxycarbonyl group, phenyloxycarbonyl group, o-tolyloxycarbonyl group, etc. to 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) ), a group derivatized with an oxycarbonyl group to which) is bonded;

Amino group; N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N- Diisopropylamino group, N-butylamino group, N,N-dibutylamino group, N-isobutylamino group, N,N-diisobutylamino group, N-sec-butylamino group, N,N-disec-butylamino group, N-tert-butylamino group, N,N-ditert-butylamino group, N-pentylamino group, N,N-dipentylamino group, N-(1-ethylpropyl)amino group, N,N-di(1-ethylpropyl) )Amino group, N-hexylamino group, N,N-dihexylamino group, N-(2-ethyl)hexylamino group, N,N-di(2-ethyl)hexylamino group, N-heptylamino group, N,N-diheptyl Amino group, N-octylamino group, N,N-dioctylamino group, N-nonylamino group, N,N-dinonylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N ,N-propylmethylamino group, N,N-isopropylmethylamino group, N,N-butylmethylamino group, N-decylamino group, N,N-decylmethylamino group, N-undecylamino group, N,N-undecylmethyl Amino group, N-dodecylamino group, N,N-dodecylmethylamino group, N-icosylamino group, N,N-icosylmethylamino group, N,N-tert-butylmethylamino group, N,N-phenylmethylamino group, etc. , and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an amino group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

sulfamoyl group; N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N,N-diethylsulfamoyl group, N-propylsulfamoyl group, N,N-dipropylsulfamoyl group, N-isopropylsulfamoyl group, N,N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N,N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N,N-diiso Butylsulfamoyl group, N-sec-butylsulfamoyl group, N,N-disec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N-pentyl group sulfamoyl group, N,N-dipentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N, N-dihexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N,N-diheptylsulfamo Diyl, N-octylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-octylmethylsulfamoyl group, N-nonylsulfamoyl group, N,N-dinonylsulfamoyl group, N-phenylsulfa Moyl group, N,N-diphenylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-butylmethyl Sulfamoyl group, N-decylsulfamoyl group, N,N-decylmethylsulfamoyl group, N-undecylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N-dodecylsulfamoyl group, N, N-dodecylmethylsulfamoyl group, N-icosylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, etc. , and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a sulfamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms), such as amino groups, decanoylamino groups, undecanoylamino groups, dodecanoylamino groups, henicosanoylamino groups, benzoylamino groups, and groups represented by the following formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. a carbonylamino group to which the group) is bonded (when the carbonylamino group is an alkanoylamino group, the carbon number is preferably 1 to 12);

hydroxyl group; Halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a carboxyl group, —CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); a sulfo group, -SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium) a nitro group; cyano group; formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, and the like, and groups having 1 to 20 carbon atoms (preferably 1 to carbon atoms) 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) a carbonyloxy group (when the carbonyloxy group is an alkanoyloxy group, the carbon number is preferably 1 to 10) to which a group derivatized with a group derivatized with the like) is bonded;

Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl)hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, unde A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a silsulfonyl group, a dodecylsulfonyl group, an icosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, and a group represented by the following formula or a derivatized group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. ) is a sulfonyl group bonded;

carbamoyl group; N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N,N-diethylcarbamoyl group, N-propylcarbamoyl group, N,N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N,N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N,N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N,N-diiso Butylcarbamoyl group, N-sec-butylcarbamoyl group, N,N-disec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N-pentyl group Carbamoyl group, N,N-dipentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N, N-dihexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N,N-diheptylcarbamo group Diyl, N-octylcarbamoyl group, N,N-dioctylcarbamoyl group, N-nonylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-octylbutylcarbamoyl group, N,N- dinonylcarbamoyl group, N-phenylcarbamoyl group, N,N-diphenylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-isopropylmethyl Carbamoyl group, N,N-butylmethylcarbamoyl group, N-decylcarbamoyl group, N,N-decylmethylcarbamoyl group, N-undecylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N-dodecylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N-icosylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, One or two C1-C20 (preferably C1-C10) hydrocarbon groups, such as N,N-phenylmethylcarbamoyl group, and the group represented by the following formula, or its derivatized group (for example, a carboxy group , a carbamoyl group substituted with a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group);

Trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluoro All hydrogen atoms such as octyl group, perfluorononyl group, perfluorodecyl group, perfluorodecyl group, perfluorododecyl group, perfluoroicosyl group, perfluorocyclohexyl group and perfluorophenyl group a hydrocarbon group having 1 to 20 carbon atoms substituted with a fluorine atom;

Perfluoroethylmethyl group, perfluoropropylmethyl group, perfluoroisopropylmethyl group, perfluorobutylmethyl group, perfluoropentylmethyl group, perfluorohexylmethyl group, perfluoroheptylmethyl group, perfluorooctylmethyl group, purple A linear or branched chain having 1 to 20 carbon atoms in which all hydrogen atoms, such as a luoronylmethyl group, perfluorodecylmethyl group, perfluorodecylmethyl group, perfluorododecylmethyl group, and perfluoroicosylmethyl group, are substituted with fluorine atoms a hydrocarbon group having 1 to 20 carbon atoms substituted with an alkyl group of;

Some of the hydrogen atoms such as 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group and 2,4,6-trifluorophenyl group are substituted with fluorine having 1 to 20 carbon atoms (preferably from 1 to 20 carbon atoms) The hydrocarbon group of 10);

-CO-SH, -CO-S-CH ₃ , -CO-S-CH ₂ CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₂ a thiocarbonyl group bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as -CH ₃ , a thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms such as -CO-SC ₆ H ₅ ; *-COCO-R represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those satisfying 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group (for example, a group derivatized with a carboxy group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) ) of the group;

*-NRCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivative thereof a group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.); The R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivative thereof a group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.); The R groups may be the same as or different from each other, and may be bonded to each other to form a ring);

*-NRCOOR represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OP(O)(OR) ₂ such as *-OP(O)(OCH ₃ ) ₂ (wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms (for example, the hydrocarbon group mentioned above) Those satisfying heavy carbon atoms of 1 to 20), or a derivatized group thereof (eg, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a chlorine atom) is a group derivatized with an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-SiR ₃ (formulae such as *-Si(CH ₃ ) ₃ , *-Si(CH ₂ CH ₃ ), *-Si(C ₆ H ₅ ) ₃ and *-Si(CH(CH ₃ ) ₂ ) ₃ , etc. Among them, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), wherein R may be the same as or different from each other and may combine with each other to form a ring);

and the like.

Examples of the divalent substituent include an imino group substituted by an oxo group, a thioxo group, an imino group, an imino group substituted by an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted by an aryl group having 6 to 20 carbon atoms. can Examples of the imino group substituted by the alkyl group include CH ₃ -N=, CH ₃ -CH ₂ -N=, CH ₃ -(CH ₂ ) ₂ -N=, and CH ₃ -(CH ₂ ) ₃ -N=. there is. Examples of the imino group substituted by the aryl group include C ₆ H ₅ -N=.

As a substituent of a C1-C40 hydrocarbon group, Preferably, the substituent of group s1 is mentioned. The derivatized group shown below is preferably a group derivatized with a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) or the like. Do.

[group s1]

an oxy group in which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; sulfamoyl group; a sulfamoyl group substituted with one or two C1-C20 hydrocarbon groups or derivatives thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; halogen atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof;

a hydrocarbon group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms;

a hydrocarbon group having 1 to 20 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom, a linear or branched alkyl group having 1 to 20 carbon atoms;

a hydrocarbon group having 1 to 20 carbon atoms in which a part of hydrogen atoms are substituted with fluorine;

oxo.

As a substituent of a C1-C40 hydrocarbon group, More preferably, the substituent of group s2 is mentioned.

[group s2]

an oxy group in which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms;

sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; a fluorine atom, a chlorine atom, a bromine atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom; a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo.

The hydrocarbon group having 1 to 40 carbon atoms having a substituent represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 is a hydrocarbon group having 1 to 40 carbon atoms having a monovalent or divalent substituent. and a hydrocarbon group of ∼40, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms having a monovalent or divalent substituent, and a saturated or unsaturated group having 3 to 30 carbon atoms having a monovalent or divalent substituent. An alicyclic hydrocarbon group, an aromatic hydrocarbon group having 6 to 30 carbon atoms having a monovalent or divalent substituent, or a group combining hydrocarbon groups, and a group having 1 to 30 carbon atoms having a monovalent or divalent substituent;

More preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, and a carbon number having a substituent in group s1 It is a group combining 6-20 aromatic hydrocarbon groups or hydrocarbon groups, and a C1-C20 group which has a substituent of group s1 is mentioned,

Particularly preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, a carbon number having a substituent of group s2 It is a group combining the aromatic hydrocarbon group or hydrocarbon group of 6-15, and the group of C1-C15 which has a substituent of group s2 is mentioned.

The heterocyclic group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 may be monocyclic or polycyclic, and preferably contains a hetero atom as a component of the ring. It is a complex ring that As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned.

The heterocyclic group preferably has 3 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, still more preferably 3 to 20 carbon atoms, still more preferably 3 to 18 carbon atoms, still more preferably 3 to 15 carbon atoms. and particularly preferably 3 to 14.

Examples of the heterocycle containing a nitrogen atom include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrroles such as 2,5-dimethylpyrrole, pyrazoles such as 2-methylpyrazole and 3-methylpyrazole, and 5-membered rings such as imidazole, 1,2,3-triazole and 1,2,4-triazole systemic unsaturated heterocycle;

pyrimidines such as pyridine, pyridazine and 6-methylpyrimidine; 6-membered ring unsaturated heterocycles such as pyrazine and 1,3,5-triazine;

Quinox such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline condensed bicyclic heterocycles such as saline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperizine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and the like.

Examples of the heterocycle containing an oxygen atom include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane. ; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; 5-membered ring unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran;

Condensed bicyclic heterocycles, such as benzopyran, such as 1-benzofuran and 4-methylbenzopyran, benzodioxole, chroman, and isochroman; Condensed tricyclic heterocycles, such as xanthene and dibenzofuran; and the like.

As a heterocyclic ring containing a sulfur atom, 5-membered ring system saturated heterocycles, such as thiolane; 6-membered ring-based saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl 1,3-dithiane; 5-membered ring unsaturated heterocycles, such as thiophene, such as 3-methylthiophene and 2-carboxythiophene, benzothiopyran, such as 4H-thiopyran and benzotetrahydrothiopyran; Condensed bicyclic heterocycles, such as benzothiophene; condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.

Examples of the heterocycle containing a nitrogen atom and an oxygen atom include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone. Summons; Monocyclic unsaturated heterocycles, such as isoxazole, such as oxazole, such as 4-methyloxazole, 2-methylisoxazole, and 3-methylisoxazole;

Condensed bicyclic heterocyclic rings, such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline; condensed tricyclic heterocycles such as phenoxazine; and the like.

As a heterocyclic ring containing a nitrogen atom and a sulfur atom, Monocyclic heterocyclic rings, such as thiazole, such as 3-methylthiazole and 2, 4- dimethylthiazole; Condensed bicyclic heterocycles, such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine; and the like.

The heterocyclic ring may be a group in which the above-mentioned hydrocarbon groups are combined, and examples thereof include a tetrahydrofurylmethyl group and the like.

The heterocycle may be represented by the following formula.

The heterocyclic group may be a heterocyclic group formed by bonding two or more of R ^1Z3 to R ^5Z3 . Such a heterocyclic group has a ring structure of two or more rings together with the benzene ring to which R ^1Z3 to R ^5Z3 are bonded. As a ring structure of this two or more rings, the structure of the following formula is mentioned, for example.

The bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is removed.

The heterocyclic group represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1Z3 , R 2Z3 , R 3Z3 , R 4Z3 , R 5Z3 , R 6Z3 , R 7Z3 , R 101Z3 and R 102Z3 may} have. Moreover, when the said heterocyclic ring contains the nitrogen atom as its structural element, the hydrocarbon group mentioned above may couple|bond with this nitrogen atom as a substituent.

Preferred examples of the substituent include the same as the preferred substituents which the hydrocarbon group represented by R ^{1Z3 , R 2Z3 , R 3Z3 , R 4Z3 , R 5Z3 , R 6Z3 , R 7Z3 , R 101Z3 and R 102Z3 may have} . Examples of the heterocyclic group having a substituent represented by R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , R ^7Z3 , R ^101Z3 and R ^102Z3 include a heterocyclic group having a monovalent or divalent substituent; Preferably, a heterocyclic group having a substituent of group s1 is mentioned, and more preferably, a heterocyclic group having a substituent of group s2 is mentioned.

The number of substituents (1st substituent) which the said hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may mutually independently be the same or different. As for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

Hereinafter, -CO-R ^102Z3 , -COO-R ^101Z3 , -OCO-R ^102Z3 , -COCO-R ^102Z3 , -OR of R ^1Z3 , R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , and R ^{7Z3 102Z3} , -SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , a halogen atom, -SO ₃ M, and -CO ₂ M will be described.

-CO-R ^{102Z3 is} a formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the above formulas, such as a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxyl group, alcohol A carbonyl group (a group derivatized with an agar, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) In the compound shown in Table 1Z3 to Table 6Z3, the group corresponding to -CO-R ^102Z3 , etc. are mentioned, Preferably it is C1-C11 (More preferably, it is C1-C11 -CO-R 102Z3 in the compounds shown in the hydrocarbon group of 10) or a derivatized group bonded thereto (when the carbonyl group is an alkanoyl group, the carbon number is more preferably 2 to 12), and Tables 1Z3 to ^6Z3 and groups corresponding to .

-COO-R ^101Z3 is a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, and groups represented by the above formulas having 1 to 40 carbon atoms (preferably from 1 to carbon atoms). 20) of a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) In the compounds shown in Tables ^1Z3 to Table 6Z3 and the oxycarbonyl group to which a group derivatized with a The group corresponding to -COO-R ^102Z3 in the compound shown in the couple|bonded oxycarbonyl group and Tables 1Z3 - Table 6Z3, etc. are mentioned.

-OCO-R ^102Z3 is a formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, etc., and groups represented by the above formulas having 1 to 40 carbon atoms (preferably from 1 to carbon atoms). 20) of a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) In the compounds shown in Tables 1Z3 to 6Z3, -OCO-R ^102Z3 in the carbonyloxy group to which a carbonyloxy group (a group derivatized with, etc.) is bonded (when the carbonyloxy group is an acyloxy group, it has 2 to 41 carbon atoms) and the like, preferably a carbonyloxy group to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivatized group thereof is bonded (when the carbonyloxy group is an acyloxy group, The number of carbon atoms is more preferably 2 to 12), and groups corresponding to -OCO-R ^102Z3 in the compounds shown in Tables 1Z3 to 6Z3, and the like.

-COCO-R ^102Z3 is methyloxalyl group, ethyloxalyl group, propyloxalyl group, butyloxalyl group, pentyloxalyl group, hexyloxalyl group, (2-ethyl)hexyloxalyl group, heptyloxalyl group group, octyloxalyl group, nonyloxalyl group, decyloxalyl group, undecyloxalyl group, dodecyloxalyl group, icosyloxalyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p - a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as a tolyloxalyl group, and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, In the compounds shown in Tables 1Z3 to 6Z3 and an oxalyl group to which a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. is bonded - The group corresponding to COCO-R ^102Z3 , etc. are mentioned.

-OR ^{102Z3 is} a hydroxyl group; Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group Group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2 ,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyl group Oxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyl Oxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-e A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof, such as a oxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, and a group represented by the above formula A group (for example, a group derivatized with a carboxy group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) In the oxy group and the compounds shown in Tables 1Z3 to 6Z3, a group corresponding to -OR ^102Z3 is mentioned, and preferably an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded, and Tables 1Z3 to 6Z3 In the compound shown, the group corresponding to -OR ^102Z3 , etc. are mentioned.

-SO ₂ -R ^{101Z3 is} a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl)hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, and a nonyl group. sulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, and groups having 1 to 40 carbon atoms (preferably carbon atoms) 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) sulfonyl group) to which a group derivatized with a diyl) is bonded, and a group corresponding to -SO ₂ -R ^102Z3 in the compounds shown in Tables 1Z3 to 6Z3, etc., and preferably a hydrocarbon group having 1 to 10 carbon atoms or and the group corresponding to -SO ₂ -R ^102Z3 in the compounds shown in the sulfonyl group to which the derivatizing group is bonded and Tables 1Z3 to 6Z3.

As -SO ₂ N(R ^102Z3 ) ₂ , a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfa Moyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A sulfamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z3 to 6Z3 In the compound represented by -SO ₂ NH(R ^102Z3X ) (provided that R ^102Z3X is the same as R ^102Z3 except that it does not form a hydrogen atom);

N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-dipropylsulfamoyl group, N ,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-disec -Butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group, N,N-dipentylsulfamoyl group, N, N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N,N-diheptylsulfamoyl group, N, N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decylmethylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N ,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, N,N-diphenylsulfamoyl group, etc., and groups represented by the above formulas, etc. of two C1 to C40 (preferably C1 to C20) hydrocarbon groups or derivatized groups thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), 1 to 10 carbon atoms) A sulfamoyl group substituted with an alkylsulfamoyl group (preferably a group derivatized with an octylsulfamoyl group, etc.) of -SO ₂ N(R ^102Z3X ) ₂ (provided that R ^102Z3X is the same as R ^102Z3 except that it does not become a hydrogen atom);

Preferably, in the compounds shown in Tables 1Z3 to Table 6Z3 and a sulfamoyl group substituted with one or two C1-C10 hydrocarbon groups or derivatized groups thereof, a group corresponding to -SO ₂ N(R ^102Z3 ) ₂ , etc. can be heard

-CON(R ^102Z3 ) ₂ is a carbamoyl group; N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarp Bamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group and N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z3 to 6Z3 In the compound represented by -CONNH(R ^102Z3X ) (R ^102Z3X is the same as R ^102Z3 except that it does not form a hydrogen atom), etc.;

N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N ,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec -Butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-dibutylcarbamoyl group, N,N-butyloctylcarbamoyl group, N, N-dipentylcarbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N,N-dihexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N, N-diheptylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N,N-decylmethylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-phenylmethylcarbamoyl group, N,N-diphenylcarbamoyl group two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as groups and groups represented by the above formulas, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen ( Preferably a chlorine atom), a carbamoyl group substituted with a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc., and -CON in the compounds shown in Tables 1Z3 to 6Z3 (R ^102Z3X ) ₂ (R ^102Z3X is the same as R ^102Z3 except that it does not form a hydrogen atom);

Preferably, a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, and a group corresponding to -CON(R ^102Z3 ) ₂ in the compounds shown in Tables 1Z3 to 6Z3, etc. can be mentioned. there is.

-N(R ^102Z3 ) ₂ is an amino group; N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group , N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, N-dodecylamino group, N- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as an icosylamino group, N-phenylamino group, and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, An amino group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like shown in Tables 1Z3 to 6Z3 a group corresponding to -NH(R ^102Z3X ) (R ^102Z3X is the same as R ^102Z3 except that it does not form a hydrogen atom) in the compound;

N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N, N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N-diisobutylamino group, N,N-disec-butylamino group, N,N-ditert-butylamino group, N,N- Butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, N,N-di(1-ethylpropyl)amino group, N,N-dihexylamino group, N,N-di(2-ethyl) ) hexylamino group, N,N-diheptylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N,N-decylmethylamino group, N,N-undecylmethylamino group, N,N-dode A sylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc., and groups represented by the above formulas, such as groups having 1 to 40 carbon atoms (preferably carbon atoms) 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) In the compounds shown in Tables 1Z3 to 6Z3 and an amino group substituted with a group derivatized with a diyl), etc., -N(R ^102Z3X ) ₂ (R ^102Z3X is the same as R ^102Z3 except that it does not become a hydrogen atom) group, etc.; and an amino group preferably substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, and a group corresponding to -N(R ^102Z3 ) ₂ in the compounds shown in Tables 1Z3 to 6Z3, etc. can be heard

-NHCO-R ^{102Z3 is} a formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as amino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group, and groups represented by the above formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. group) to which the carbonylamino group is bonded (when the carbonylamino group is an acylamino group, it has 1 to 40 carbon atoms), and a group corresponding to -NHCO-R ^102Z3 in the compounds shown in Tables 1Z3 to 6Z3. can,

Preferably, a hydrocarbon group having 1 to 10 carbon atoms or a carbonyl amino group to which a derivatized group thereof is bonded (when the carbonyl amino group is an alkanoylamino group, the carbon number is more preferably 1 to 10) and Tables 1Z3 to 6Z3 The group corresponding to -NHCO-R ^102Z3 in a compound, etc. are mentioned.

Examples of -NHCON(R ^102Z3 ) ₂ include the groups listed above and groups corresponding to -NHCON(R ^102Z3 ) ₂ in the compounds shown in Tables 1Z3 to 6Z3.

Examples of -NHCOOR ^102Z3 include the groups listed above and groups corresponding to -NHCOOR ^102Z3 in the compounds shown in Tables 1Z3 to 6Z3.

Examples of -OCON(R ^102Z3 ) ₂ include the groups listed above and groups corresponding to -OCON(R ^102Z3 ) ₂ in the compounds shown in Tables 1Z3 to 6Z3.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are preferable.

As M of -SO ₃ M and -CO ₂ M, a hydrogen atom; Alkali metal atoms, such as a lithium atom, a sodium atom, and a potassium atom, are mentioned, Preferably, a hydrogen atom, a sodium atom, and a potassium atom are mentioned.

The -CO-R ^102Z3 , -COO-R ^102Z3 , -OCO-R ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , -SO ₂ -R ^102Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCON(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ Substituents (first substituents) included in 2 are one Or two or more may be sufficient, and two or more substituents mutually independently may be same or different.

In addition, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

The ring formed by ^R2Z3 and ^R3Z3 , ^R3Z3 and ^R4Z3 , and ^R4Z3 and ^R5Z3 is condensed with the benzene ring of the isoindoline skeleton of the compound represented by Formula IZ3. Examples of the condensed structure of the benzene ring and the ring formed by R ^2Z3 and R ^3Z3 , R ^3Z3 and R ^4Z3 , and R ^4Z3 and R ^5Z3 include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, and phenylene. nalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, N-methylphthalimide, N-(1-phenylethyl)phthalimide and tetracene hydrocarbon-based condensed ring structures and partial reduction products thereof (eg, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); Indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, perimidine, phenanthroline and phenazine, etc. of nitrogen-containing condensed heterocycles and partial reduction products thereof; and oxygen-containing condensed heterocycles such as 3-hydrobenzofuran 2-one, and partially reduced products thereof.

When R ^2Z3 and R ^3Z3 , R ^3Z3 and R ^4Z3 , and R ^4Z3 and R ^5Z3 form a ring, the ring may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1Z3 , R 2Z3 , R 3Z3 , R 4Z3 , R 5Z3 , R 6Z3 , R 7Z3 , R 101Z3 and R 102Z3 may} have. Preferred examples of the substituent include the same as preferred substituents which the hydrocarbon group represented by R ^{1Z3 , R 2Z3 , R 3Z3 , R 4Z3 , R 5Z3 , R 6Z3 , R 7Z3 , R 101Z3 and R 102Z3 may have} .

When R ^3Z3 and R ^4Z3 form a ring, it is preferable that R ^2Z3 and R ^5Z3 independently represent a hydrogen atom, an amino group and a hydroxyl group.

When R ^2Z3 and R ^3Z3 form a ring, R ^4Z3 and R ^5Z3 preferably do not form a ring, and more preferably R ^4Z3 and R ^5Z3 are hydrogen atoms.

When R ^4Z3 and R ^5Z3 form a ring, R ^2Z3 and R ^3Z3 preferably do not form a ring, and more preferably R ^2Z3 and R ^3Z3 are hydrogen atoms.

In the present invention, R ^1Z3 , R ^6Z3 and R ^7Z3 are preferably a hydrogen atom.

At least one of R ^2Z3 , R ^3Z3 , R ^4Z3 , and R ^5Z3 is -CO-R ^102Z3 , -COO-R ^101Z3 , -OCO-R from a viewpoint that the phase difference value of the color filter manufactured from the coloring composition becomes small ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , -SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, optionally having 1 to carbon atoms It is preferable that it is a 40 hydrocarbon group or a heterocyclic group which may have a substituent, and all or part of a C1-C40 hydrocarbon group which may have a substituent, a halogen atom, -N(R ^102Z3 ) ₂ , a nitro group, and a hydrogen atom. A hydrocarbon group having 1 to 20 carbon atoms in which a fluorine atom is substituted, -NHCO-R ^102Z3 , -OR ^102Z3 , -SO ₃ M or -CO ₂ M is more preferable, and a nitro group or a C1-C40 hydrocarbon group which may have a substituent It is more preferably a hydrocarbon group, and still more preferably a nitro group or a tert-butyl group. Alternatively, at least one set of R ^2Z3 and R ^3Z3 , R ^3Z3 and R ^4Z3 , or R ^4Z3 and R ^5Z3 preferably forms a ring.

Compound IZ3 is, wherein at least one of R ^2Z3 , R ^3Z3 , R ^4Z3 , and R ^5Z3 is -CO-R ^102Z3 , -COO-R ^101Z3 , -OCO-R ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , - SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent; , or a compound in which at least one set of R ^2Z3 and R ^3Z3 , R ^3Z3 and R ^4Z3 , and R ^4Z3 and R ^5Z3 is bonded to form a ring (hereafter referred to as “compound IZ3-B”) there are cases). When compound IZ3 is compound IZ3-B, the retardation value of the color filter manufactured from the coloring composition becomes small.

When the compound IZ3-B is defined by the formula, it is as follows.

[In formula (IZ3-B), R ^1Z3 , R ^21Z3 , R ^31Z3 , R ^41Z3 , R ^51Z3 , R ^61Z3 , and R ^71Z3 are, independently of each other, a hydrogen atom, -CO-R ^102Z3 , -COO-R ^101Z3 , -OCO-R ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , -SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, having a substituent It represents the optionally C1-C40 hydrocarbon group or the heterocyclic group which may have a substituent.

R ^21Z3 and R ^31Z3 , R ^31Z3 and R ^41Z3 , and R ^41Z3 and R ^51Z3 may be respectively bonded to each other to form a ring.

provided that at least one of R ^21Z3 , R ^31Z3 , R ^41Z3 , and R ^5Z3 is -CO-R ^102Z3 , -COO-R ^101Z3 , -OCO-R ^102Z3 , -COCO-R ^102Z3 , -OR ^102Z3 , -SO ₂ -R ^101Z3 , -SO ₂ N(R ^102Z3 ) ₂ , -CON(R ^102Z3 ) ₂ , -N(R ^102Z3 ) ₂ , -NHCO-R ^102Z3 , -NHCO-N(R ^102Z3 ) ₂ , -NHCOOR ^102Z3 , -OCON(R ^102Z3 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or At least one set of R ^21Z3 and R ^31Z3 , R ^31Z3 and R ^41Z3 , and R ^41Z3 and R ^51Z3 is bonded to form a ring.

R ^101Z3 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102Z3 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M represents a hydrogen atom or an alkali metal atom.

When two or more R ^101Z3 , R ^102Z3 and M exist, they may be same or different. The broken line indicates the E or Z body.]

In formula IZ3-B, R ^21Z3 , R ^31Z3 , R ^41Z3 , R ^51Z3 , R ^61Z3 , and R ^71Z3 are, respectively, R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , and R ^7Z3 in formula IZ3 the same can be mentioned. In formula IZ3-B, preferred R ^21Z3 , R ^31Z3 , R ^41Z3 , R ^51Z3 , R ^61Z3 , and R ^71Z3 are, respectively, R ^2Z3 , R ^3Z3 , R ^4Z3 , R ^5Z3 , R ^6Z3 , and R 7Z3 in formula ^IZ3 The same thing as preferable of can be mentioned.

In the formula IZ3-B, (Aspect 1) R ^1Z3 , R ^61Z3 and R ^71Z3 are preferably a hydrogen atom. Also (Mode 2), it is preferable that at least one of R ^21Z3 , R ^31Z3 , R ^41Z3 , and R ^51Z3 is a nitro group or a tert-butyl group. Either one of aspects 1 and 2 may be employ|adopted and both may be employ|adopted.

From the viewpoint of decreasing the retardation value of the color filter produced from the coloring composition, at least one of R ^2Z3 , R ^3Z3 , R ^4Z3 , and R ^5Z3 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, -N(R ^102Z3 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z3 , -OR ^102Z3 , -SO ₃ M or -CO ₂ M It is preferable that it is a nitro group or a C1-C40 hydrocarbon group which may have a substituent, It is more preferable that it is a nitro group or a tert- butyl group. Particularly preferably, R ^3Z3 is a nitro group or a tert-butyl group and R ^2Z3 , R ^4Z3 and R ^5Z3 are a hydrogen atom, or R ^2Z3 , R ^3Z3 and R ^5Z3 are a hydrogen atom and R ^4Z3 is a nitro group or tert -It is a butyl group.

Specific examples of the compound IZ3 include, for example, compounds IZ3-1 to compound IZ3-212 having a substituent shown in Table 1Z3, Table 2Z3, Table 3Z3, Table 4Z3, Table 5Z3, and Table 6Z3 in the formula IZ3-aa; The alkali metal salt is mentioned.

B ^a1Z3 B ^a2Z3 is a formula (BB1) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1), a formula (BBO8), a formula (BBO10) , any partial structure represented by the formulas (BBD1) and (BBJ2) is shown. Formula (BB1) to Formula (BB60), Formula (BBK2), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), Formula (BBO8), Formula (BBO10), Formula (BBD1) and Formula (BBJ2) is (BB1) to ( ^BB60 ), Formula ( ^BBK2 ), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), It is equivalent to formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2).

B ^a1Z3 and B ^a2Z3 each represent a bond, and B ^a1Z3 is a formula (BB1) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1) , B ^a2Z3 becomes a bond of B ² when it is a bond of B ¹ in formulas (BBO8), (BBO10), (BBD1) and (BBJ2), and B ^a1Z3 is a bond of formulas (BB1) to (BB60) ), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) ^of B2 In the case of a bond, B ^a2Z3 becomes a bond of B ¹ .

As B ^a1Z3 B ^a2Z3 , Formula (BB1), Formula (BB6), Formula (BB8), Formula (BB11), Formula (BB14), Formula (BB19), Formula (BB37), Formula (BB58), Formula (BBJ2) , the formulas (BBO8) and (BBO10) are preferable, and the formulas (BB1), (BB6) and (BB19) are more preferable.

Each symbol in Table 1Z3, Table 2Z3, Table 3Z3, Table 4Z3, Table 5Z3, and Table 6Z3 shows the following partial structures. In addition, in the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ"" represents a benzyl group, "NPR" represents a propyl group, "IPR" represents an isopropyl group, "IBu" represents an isobutyl group, "EOE" represents -CH ₂ CH ₂ OCH ₂ CH ₃ , "ALL " represents an allyl group, "HYE" represents a 2-hydroxyethyl group, "COM" represents -CO-CH ₃ , "COE" represents -COO-CH ₂ CH ₃ , and "OCM" represents -OCO represents -CH ₃ , "OME" represents -O-CH ₃ , "SOT" represents a tosyl group, "SNH" represents -SO ₂ NH-CH ₂ CH(CH ₂ CH ₃ )((CH ₂ ) ₃ CH ₃ ), "SN2" is -SO ₂ N(CH ₃ ) ((CH ₂ ) ₇ CH ₃ ), "CNM" is -CONHCH ₃ , "CN2" is -CON(CH ₃ ) )C ₆ H ₅ , “NPH” is —NHC ₆ H ₅ , “NOT” is —N((CH ₂ ) ₇ CH ₃ ) ₂ , “NCO” is —NHCO((CH ₂ ) ₄ CH ₃ ), "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO2" represents a nitro group , "SUA" represents -SO ₃ H, "CBA" represents -CO ₂ H, "CHO" represents -CHO, "OCH" represents -OCOH, "OH" represents -OH, "SFM" represents -SO ₂ NH ₂ , "CBM" represents -CONH ₂ , and "NH2" is - NH2 is _shown , and "NCH" shows -NHCOH.

[Table 1Z3]

[Table 2Z3]

[Table 3Z3]

[Table 4Z3]

[Table 5Z3]

[Table 6Z3]

For example, compound IZ3-1 is a compound represented by Formula IZ3-1.

As compound IZ3, compound IZ3-1 - compound IZ3-120 and IZ3-207 - compound IZ3-212 are preferable, compound IZ3-1 - compound IZ3-120 are more preferable, compound IZ3-1 - compound IZ3-60 are more preferably, the compound IZ3-1 to the compound IZ3-36, the compound IZ3-37 and the compound IZ3-58 are even more preferable,

Compound IZ3-1 to compound IZ3-36 are particularly preferred, and compound IZ3-1, compound IZ3-6, compound IZ3-8, compound IZ3-11, compound IZ3-14 and compound IZ3-19 are particularly preferred, compound IZ3-19 Particular preference is given to IZ3-1, compound IZ3-6, and compound IZ3-19.

Specific examples of the compound IZ3 include compounds in which -SO ₃ M or -CO ₂ M is substituted for 1 to 3 hydrogen atoms contained in the compounds shown in Tables 1Z3 to 6Z3. For example, a compound in which 1 to 3 sulfo groups are bonded to compound IZ3-1 of Table 1Z3 is represented by the following structure. However, in the formula, -(SO ₃ H) shall mean that the hydrogen atom in any of the compounds IZ3-1 of Table 1Z3 is substituted.

In the present invention, compounds IZ3-1 to compound IZ3-120 and IZ3-207 to compound IZ3-212 are preferably compounds in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded;

A compound in which one to three -SO ₃ M or -CO ₂ M is bonded to compound IZ3-1 to compound IZ3-120 is more preferable, and to compound IZ3-1 to compound IZ3-60, one to three -SO A compound in which ₃ M or -CO ₂ M is bonded is more preferable, and in compound IZ3-1 to compound IZ3-36, compound IZ3-37 and compound IZ3-58, 1 to 3 -SO ₃ M or -CO ₂ M This bonded compound is even more preferable, and a compound in which one to three -SO ₃ M or -CO ₂ M is bonded to compound IZ3-1 to compound IZ3-36 is particularly preferable, and compound IZ3-1, compound IZ3 A compound in which 1 to 3 -SO ₃ M or -CO ₂ M is bonded to -6, compound IZ3-8, compound IZ3-11, compound IZ3-14, and compound IZ3-19 is particularly more preferable, and compound IZ3- 1, the compound IZ3-6 or the compound IZ3-19 with 1 to 3 -SO ₃ M or -CO ₂ M bonded to a compound is particularly preferred.

As the compound (IZ3), in the formula (IZ3), R ^1Z3 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, -SO ₃ M or -CO ₂ M,

R ^2Z3 to R ^5Z3 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, —N(R ^102Z3 ) ₂ , a nitro group, or a fluorine atom having 1 carbon atom in which all or part of the hydrogen atoms are substituted -20 hydrocarbon group, -NHCO-R ^102Z3 , -OR ^102Z3 , -SO ₃ M or -CO ₂ M,

R ^6Z3 and R ^7Z3 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, -SO ₃ M or -CO ₂ M, R ^102Z3 is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, M is a hydrogen atom or an alkali metal atom Compounds are preferred, R ^1Z3 is a hydrogen atom,

R ^2Z3 to R ^5Z3 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102Z3 ) ₂ , a nitro group, or a fluorine atom having 1 carbon atom in which all or part of the hydrogen atoms are substituted a hydrocarbon group of -10, -NHCO-R ^102Z3 , -OR ^102Z3 , -SO ₃ M or -CO ₂ M, R ^6Z3 and R ^7Z3 are the same group, and a hydrogen atom, or -SO ₃ M and -CO ₂ It is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of M, and R ^102Z3 is a hydrogen atom or carbon number which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M It is a hydrocarbon group of 1 to 10,

M is more preferably a hydrogen atom or an alkali metal atom,

R ^1Z3 is a hydrogen atom, R ^2Z3 to R ^5Z3 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, —N(R ^102Z3 ) ₂ , a nitro group, a trifluoromethyl group, -OR ^102Z3 , -SO ₃ M or -CO ₂ M, R ^6Z3 and R ^7Z3 are the same group and are a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms;

R ^102Z3 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

M is more preferably a compound of a hydrogen atom or an alkali metal atom.

In the compound IZ3, when R ^1Z3 is a hydrogen atom, a compound represented by the formula pt1Z3 (hereinafter sometimes referred to as a phthalonitrile compound) is reacted with a compound represented by the formula pt2Z3 (hereinafter sometimes referred to as an alkoxide compound) After the reaction, it can be prepared by further reacting the compound represented by the formula pt3Z3 with the compound represented by the formula pt4Z3 in the presence of an acid. Further, when R ^1Z3 is other than a hydrogen atom, compound IZ3 can be produced by further reacting with a compound represented by the formula pt5Z3.

[In the formula pt1Z3, the formula pt2Z3, the formula pt3Z3, the formula pt4Z3, the formula pt5Z3, and the formula IZ3, R ^1Z3 to R ^7Z3 have the same meanings as described above. R ^14Z3 represents an alkyl group having 1 to 20 carbon atoms. M ^1Z3 represents an alkali metal atom. LG represents a halogen atom, a methanesulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group.]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ^14Z3 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group, and preferably a C1 group. -6 alkyl groups are mentioned.

Examples of the alkali metal atom represented by M ^1Z3 include a lithium atom, a sodium atom and a potassium atom.

The usage-amount of an alkoxide compound is 0.1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 0.2-5 mol, More preferably, it is 0.3-3 mol, More preferably, it is 0.4-2 mol. it's a mall

The amount of the compound pt3Z3 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 2 moles, with respect to 1 mole of the phthalonitrile compound. am.

The usage-amount of compound pt4Z3 is 1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 1-5 mol, More preferably, it is 1-3 mol, More preferably, it is 1-2 mol. am.

Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; and carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid These are mentioned, More preferably, acetic acid is mentioned.

The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, still more preferably 1 to 6 moles with respect to 1 mole of the phthalonitrile compound.

The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z3 and the compound pt4Z3 is usually carried out in the presence of a solvent.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N ,N-dimethylformaldehyde, N-methylpyrrolidone and dimethyl sulfoxide, and more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1- octanol, acetone, methylene chloride, chloroform, N,N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide are exemplified, particularly preferably water, acetonitrile, methanol, ethanol and 2-propanol. can be heard

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of phthalonitrile compounds.

Reaction temperature is 0-200 degreeC normally, Preferably it is 0-100 degreeC, More preferably, it is 0-70 degreeC, More preferably, it is 0-50 degreeC. Reaction time is 0.5 to 300 hours normally.

The amount of compound pt5Z3 to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and more preferably 1 mole to 1 mole of compound IZ3 in which R ^1Z3 is a hydrogen atom. 1 to 2 moles.

When the compound pt5Z3 is reacted, it is preferable that a base coexist. Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; organometallic compounds such as butyllithium, tert-butyllithium and phenyllithium; Inorganic bases, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, are mentioned.

The amount of the base used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 10 moles with respect to 1 mole of compound IZ3 in which R ^1Z3 is a hydrogen atom. 2 moles.

The reaction of the compound pt5Z3 is usually carried out in the presence of a solvent. A solvent can be selected from the range similar to the above.

The amount of the solvent used is usually from 1 to 1000 parts by mass based on 1 part by mass of the compound IZ3 in which R ^1Z3 is a hydrogen atom. The reaction temperature of the compound pt5Z3 is usually -90 to 200°C, preferably -80 to 100°C, more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

When compound IZ3 does not have a sulfo group or -SO ₃ M ² , a sulfo group or -SO ₃ M ²² can be introduced by reacting compound IZ3 with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid.

M ²² represents an alkali metal atom. Examples of the alkali metal atom represented by M ²² include a lithium atom, a sodium atom and a potassium atom.

The amount of SO ₃ used in the fuming sulfuric acid is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, more preferably 5 to 25 moles, with respect to 1 mole of compound IZ3. am.

The amount of sulfuric acid used in the fuming sulfuric acid is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, still more preferably 10 to 50 moles with respect to 1 mole of compound IZ3. .

The usage-amount of chlorosulfonic acid is 1-500 mol normally with respect to 1 mol of compound IZ3, Preferably it is 10-300 mol, More preferably, it is 10-200 mol, More preferably, it is 10-150 mol.

The reaction temperature for sulfonation is usually -20 to 200°C, preferably -10 to 100°C, and more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

The method for taking out compound IZ3 from the reaction mixture is not particularly limited, and can be taken out by various known methods. For example, after completion of the reaction, the compound IZ3 can be extracted by filtering the reaction mixture. After filtration, the obtained residue may be subjected to column chromatography, recrystallization, or the like. Further, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and then purified by column chromatography.

<Compound IZ4>

The compound IZ4 is a compound represented by the formula IZ4.

[In Formula IZ4, R ^N1Z4 and R ^N2Z4 are, independently of each other, -CO-R ^102Z4 , -COO-R ^101Z4 , -OCO-R ^102Z4 , -COCO-R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^101Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCO-N(R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON( R ^102Z4 ) ₂ , a halogen atom, a cyano group, a nitro group, —SO ₃ M, —CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , and R ^7Z4 are, independently of each other, a hydrogen atom, -CO-R ^102Z4 , -COO-R ^101Z4 , -OCO-R ^102Z4 , -COCO -R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^101Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCO- N(R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON(R ^102Z4 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Or the heterocyclic group which may have a substituent is shown.

R ^2Z4 and R ^3Z4 , R ^3Z4 and R ^4Z4 , and R ^4Z4 and R ^5Z4 may be respectively bonded to each other to form a ring. R ^101Z4 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R ^102Z4 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M represents a hydrogen atom or an alkali metal atom.

When two or more R ^101Z4 , R ^102Z4 and M exist, they may be same or different. The broken line indicates the E or Z body.]

The hydrocarbon group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 has 1 to 40 carbon atoms, preferably 1 to 30, More preferably, it is 1-20, More preferably, it is 1-15, Especially preferably, it is 1-10.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 include a methyl group, an ethyl group, a propyl group, straight-chain alkyl groups such as butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, heptadecyl group, octadecyl group, and icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl)pentyl group, (2- methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group and (3-ethyl) heptyl group branched chain alkyl groups and the like; Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 3-butadienyl group, (1-(2-propenyl) ) alkenyl groups such as ethenyl group, (1,2-dimethyl)propenyl group and 2-pentenyl group; and the like. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, still more preferably is 1 to 8, particularly preferably 1 to 5. Especially, it is especially preferable that it is a C1-C10, More preferably, it is a C1-C8 linear or branched alkyl group, and a methyl group, an ethyl group, and a tert- butyl group are especially preferable.

As the saturated or unsaturated alicyclic hydrocarbon group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 , cyclopropyl group, 1-methyl Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl 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 Sil 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, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and 3,3,5,5-tetramethylcyclohexyl group, 4 - cycloalkyl groups such as a pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; Cycloalkenyl groups, such as a cyclohexenyl group (For example, cyclohexa-2-ene, cyclohexa-3-ene), a cycloheptenyl group, and a cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane, etc. are mentioned. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, still more preferably 4 to 15, particularly More preferably, it is 5-15, Most preferably, it is 5-10. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

Examples of the aromatic hydrocarbon group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 include a phenyl group, an o-tolyl group, and a m-tolyl group. , p-tolyl 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, 4- vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 4-ethylphenyl group, 4-Butylphenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-vinylphenyl group, 1-naph Tyl group, 2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group and anthryl group , aromatic hydrocarbon groups such as a pyrenyl group; and the like. Carbon number of an aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-15.

The hydrocarbon group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 is the above-mentioned hydrocarbon group (for example, an aromatic hydrocarbon group; At least one of a chain hydrocarbon group and an alicyclic hydrocarbon group) may be combined, and an aralkyl group such as a benzyl group, a phenethyl group, and a 1-methyl-1-phenylethyl group; arylalkenyl groups such as a phenylethenyl group (phenylvinyl group); Aryl alkynyl groups, such as a phenylethynyl group; a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; A cyclohexylmethylphenyl group, a benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. are mentioned.

The group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 is a hydrocarbon group (for example, a chain hydrocarbon group and an alicyclic group). As the group combined with the formula hydrocarbon group), for example, cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclohexyl group The alkyl group to which one or more alicyclic hydrocarbon groups, such as an ethyl group and an adamantylmethyl group, couple|bonded may be sufficient.

These carbon number becomes like this. Preferably it is 4-30, More preferably, it is 6-30, More preferably, it is 6-20, More preferably, it is 4-20, More preferably, it is 4-15, Especially preferably, it is 6-15.

The hydrocarbon group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 may have a substituent. The substituent may be monovalent or divalent. The divalent substituent preferably has two bonds bonded to the same carbon atom to form a double bond.

As the monovalent substituent,

Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl)hexyloxy group, hep Tyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenyl ethoxy group, phenyloxy group, o-tolyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2,6-dicyanophenyloxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxy C1-C20, such as a phenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group, and groups represented by the following formulas (preferably a C1-C10 hydrocarbon group or its derivatized group (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably chlorine atom), a C1-C10 alkylsulfamoyl group (preferably) preferably an oxy group bonded to one side of a group derivatized with an octylsulfamoyl group) or the like;

Methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethyl)hexylthio group, heptylthio group, octylthio group, nonylthio group , a sulfanyl group to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a decylthio group, an undecylthio group, a dodecylthio group, an icosylthio group, a phenylthio group and an o-tolylthio group;

an epoxy group, an oxetanyl group, a tetrahydrofuryl group, a tetrahydropyranyl group; formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the following formulas, such as a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivatized group thereof (for example, a carboxy group , a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) When it is set as a canoyl group, carbon number becomes like this. Preferably it is 2-12);

Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group , a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, an icosyloxycarbonyl group, a phenyloxycarbonyl group and an o-tolyloxycarbonyl group, and a group represented by the following formulas having 1 to 20 carbon atoms (preferably 1 carbon atoms). to 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) ), a group derivatized with an oxycarbonyl group to which) is bonded;

amino group; N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diiso group Propylamino group, N-butylamino group, N,N-dibutylamino group, N-isobutylamino group, N,N-diisobutylamino group, N-sec-butylamino group, N,N-disec-butylamino group, N- tert-butylamino group, N,N-ditert-butylamino group, N-pentylamino group, N,N-dipentylamino group, N-(1-ethylpropyl)amino group, N,N-di(1-ethylpropyl)amino group , N-hexylamino group, N,N-dihexylamino group, N-(2-ethyl)hexylamino group, N,N-di(2-ethyl)hexylamino group, N-heptylamino group, N,N-diheptylamino group, N-octylamino group, N,N-dioctylamino group, N-nonylamino group, N,N-dinonylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N -Propylmethylamino group, N,N-isopropylmethylamino group, N,N-butylmethylamino group, N-decylamino group, N,N-decylmethylamino group, N-undecylamino group, N,N-undecylmethylamino group, N-dodecylamino group, N,N-dodecylmethylamino group, N-icosylamino group, N,N-icosylmethylamino group, N,N-tert-butylmethylamino group, N,N-phenylmethylamino group, and the like; A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), such as a group represented by the following formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom) , an amino group bonded to an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

sulfamoyl group; N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N,N-diethylsulfamoyl group, N-propylsulfamoyl group, N,N-dipropylsulfamoyl group, N-isopropylsulfamoyl group, N,N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N,N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N,N-diiso Butylsulfamoyl group, N-sec-butylsulfamoyl group, N,N-disec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N-pentyl group sulfamoyl group, N,N-dipentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N, N-dihexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N,N-diheptylsulfamo Diyl, N-octylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-octylmethylsulfamoyl group, N-nonylsulfamoyl group, N,N-dinonylsulfamoyl group, N-phenylsulfa Moyl group, N,N-diphenylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-butylmethyl Sulfamoyl group, N-decylsulfamoyl group, N,N-decylmethylsulfamoyl group, N-undecylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N-dodecylsulfamoyl group, N, N-dodecylmethylsulfamoyl group, N-icosylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, etc. , and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a sulfamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms), such as amino groups, decanoylamino groups, undecanoylamino groups, dodecanoylamino groups, henicosanoylamino groups, benzoylamino groups, and groups represented by the following formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. a carbonylamino group to which the group) is bonded (when the carbonylamino group is an alkanoylamino group, the carbon number is preferably 1 to 12);

hydroxyl group; Halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a carboxyl group, —CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); a sulfo group, —SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); nitro group; cyano group;

formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, and the like, and groups having 1 to 20 carbon atoms (preferably 1 to carbon atoms) 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) a carbonyloxy group (when the carbonyloxy group is an alkanoyloxy group, the carbon number is preferably 1 to 10) to which a group derivatized with, etc.) is bonded;

Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl)hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, unde A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a silsulfonyl group, a dodecylsulfonyl group, an icosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, and a group represented by the following formula or a derivatized group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. ) is a sulfonyl group bonded;

carbamoyl group; N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N,N-diethylcarbamoyl group, N-propylcarbamoyl group, N,N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N,N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N,N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N,N-diiso Butylcarbamoyl group, N-sec-butylcarbamoyl group, N,N-disec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N-pentyl group Carbamoyl group, N,N-dipentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N, N-dihexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N,N-diheptylcarbamo group Diyl, N-octylcarbamoyl group, N,N-dioctylcarbamoyl group, N-nonylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-octylbutylcarbamoyl group, N,N- dinonylcarbamoyl group, N-phenylcarbamoyl group, N,N-diphenylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-isopropylmethyl Carbamoyl group, N,N-butylmethylcarbamoyl group, N-decylcarbamoyl group, N,N-decylmethylcarbamoyl group, N-undecylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N-dodecylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N-icosylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, One or two hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), such as N,N-phenylmethylcarbamoyl group, and a group represented by the following formula, or a derivatized group thereof (for example, a carboxy group , a carbamoyl group substituted with a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group);

Trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluoro All hydrogen atoms such as octyl group, perfluorononyl group, perfluorodecyl group, perfluorodecyl group, perfluorododecyl group, perfluoroicosyl group, perfluorocyclohexyl group and perfluorophenyl group a hydrocarbon group having 1 to 20 carbon atoms substituted with a fluorine atom;

Perfluoroethylmethyl group, perfluoropropylmethyl group, perfluoroisopropylmethyl group, perfluorobutylmethyl group, perfluoropentylmethyl group, perfluorohexylmethyl group, perfluoroheptylmethyl group, perfluorooctylmethyl group, purple A linear or branched chain having 1 to 20 carbon atoms in which all hydrogen atoms, such as a luoronylmethyl group, perfluorodecylmethyl group, perfluorodecylmethyl group, perfluorododecylmethyl group, and perfluoroicosylmethyl group, are substituted with fluorine atoms a hydrocarbon group having 1 to 20 carbon atoms substituted with an alkyl group of;

Some of the hydrogen atoms such as 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group and 2,4,6-trifluorophenyl group are substituted with fluorine having 1 to 20 carbon atoms (preferably from 1 to 20 carbon atoms) The hydrocarbon group of 10);

-CO-SH, -CO-S-CH ₃ , -CO-S-CH ₂ CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₂ a thiocarbonyl group bonded to an alkyl group having 1 to 20 (preferably 1 to 10) carbon atoms such as —CH ₃ , a thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms such as —CO-SC ₆ H ₅ ;

*-COCO-R represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), etc.) of qi;

*-NRCONR ₂ represented by the formula below (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivatized group thereof ( For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivatized group thereof (For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-NRCOOR represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivatized group thereof ( For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OP(O)(OR) ₂ such as *-OP(O)(OCH ₃ ) ₂ (wherein R is a hydrogen atom and a hydrocarbon group having 1 to 20 carbon atoms (for example, among the hydrocarbon groups listed above) one having 1 to 20 carbon atoms), or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a chlorine atom) octylsulfamoyl group)), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-SiR ₃ (formulae such as *-Si(CH ₃ ) ₃ , *-Si(CH ₂ CH) ₃ , *-Si(C ₆ H ₅ ) ₃ and *-Si(CH(CH ₃ ) ₂ ) ₃ , etc. Among them, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivatized group thereof (for example, a carboxy group, sulfo group, nitro group) a group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), wherein R may be the same as or different from each other , which may be bonded to each other to form a ring); and the like.

Examples of the divalent substituent include an imino group substituted with an oxo group, a thioxo group, an imino group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted with an aryl group having 6 to 20 carbon atoms. there is. Examples of the imino group substituted by the alkyl group include CH ₃ -N=, CH ₃ -CH ₂ -N=, CH ₃ -(CH ₂ ) ₂ -N=, and CH ₃ -(CH ₂ ) ₃ -N=. there is. Examples of the imino group substituted by the aryl group include C ₆ H ₅ -N=.

As a substituent of a C1-C40 hydrocarbon group, Preferably, the substituent of group s1 is mentioned. The derivatized group shown below is preferably a group derivatized with a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) or the like. Do.

[group s1]

an oxy group in which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; halogen atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom;

a hydrocarbon group having 1 to 20 carbon atoms in which a part of hydrogen atoms are substituted with fluorine;

oxo.

As a substituent of a C1-C40 hydrocarbon group, More preferably, the substituent of group s2 is mentioned.

[group s2]

an oxy group in which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms;

sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; a fluorine atom, a chlorine atom, and a bromine atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom; a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo.

As the hydrocarbon group having 1 to 40 carbon atoms having a substituent represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 , monovalent or 2 and a hydrocarbon group having 1 to 40 carbon atoms having a valent substituent, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms having a monovalent or divalent substituent, and 3 carbon atoms having a monovalent or divalent substituent A saturated or unsaturated alicyclic hydrocarbon group having ∼30, an aromatic hydrocarbon group having 6 to 30 carbon atoms or a hydrocarbon group having a monovalent or divalent substituent, and a group having 1 to 30 carbon atoms having a monovalent or divalent substituent can,

More preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, and a carbon number having a substituent in group s1 It is a group in which an aromatic hydrocarbon group of 6 to 20 or a hydrocarbon group is combined, and a group having 1 to 20 carbon atoms having a substituent of group s1 is mentioned;

Particularly preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, a carbon number having a substituent of group s2 It is a group combining the aromatic hydrocarbon group or hydrocarbon group of 6-15, and the group of C1-C15 which has a substituent of group s2 is mentioned.

The heterocyclic group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 may be monocyclic or polycyclic, preferably a ring structure. It is a heterocyclic ring containing a hetero atom as an element. As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned.

The heterocyclic group preferably has 3 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, still more preferably 3 to 20 carbon atoms, still more preferably 3 to 18 carbon atoms, still more preferably 3 to 15 carbon atoms. and particularly preferably 3 to 14.

As a heterocyclic ring containing a nitrogen atom,

monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrroles such as 2,5-dimethylpyrrole, pyrazoles such as 2-methylpyrazole and 3-methylpyrazole, and 5-membered rings such as imidazole, 1,2,3-triazole and 1,2,4-triazole systemic unsaturated heterocycle;

pyrimidines such as pyridine, pyridazine and 6-methylpyrimidine; 6-membered ring unsaturated heterocycles such as pyrazine and 1,3,5-triazine;

Quinox such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline condensed bicyclic heterocycles such as saline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole and benzopiperidine;

condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and the like.

As a heterocyclic ring containing an oxygen atom,

monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane and 1,4-dioxane and 1-cyclopentyldioxolane;

bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane;

lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone;

5-membered ring unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran;

Condensed bicyclic heterocycles, such as benzopyran, such as 1-benzofuran and 4-methylbenzopyran, benzodioxole, chroman, and isochroman;

Condensed tricyclic heterocycles, such as xanthene and dibenzofuran; and the like.

As a heterocyclic ring containing a sulfur atom, 5-membered ring system saturated heterocycles, such as thiolane;

6-membered ring-based saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl 1,3-dithiane;

5-membered ring unsaturated heterocycles, such as thiophene, such as 3-methylthiophene and 2-carboxythiophene, benzothiopyran, such as 4H-thiopyran and benzotetrahydrothiopyran;

Condensed bicyclic heterocycles, such as benzothiophene; condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.

Examples of the heterocycle containing a nitrogen atom and an oxygen atom include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone. Summons; Monocyclic unsaturated heterocycles, such as isoxazole, such as oxazole, such as 4-methyloxazole, 2-methylisoxazole, and 3-methylisoxazole;

Condensed bicyclic heterocyclic rings, such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline; condensed tricyclic heterocycles such as phenoxazine; and the like.

As a heterocyclic ring containing a nitrogen atom and a sulfur atom, Monocyclic heterocyclic rings, such as thiazole, such as 3-methylthiazole and 2, 4- dimethylthiazole; Condensed bicyclic heterocycles, such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine; and the like.

The heterocyclic ring may be a group in which the above-mentioned hydrocarbon groups are combined, and examples thereof include a tetrahydrofurylmethyl group and the like.

In addition, the said heterocyclic ring may be represented by the following formula|equation.

The heterocyclic group may be a heterocyclic group formed by bonding two or more of R ^1Z4 to R ^5Z4 . Such a heterocyclic group has a ring structure of two or more rings together with the benzene ring to which R ^1Z4 to R ^5Z4 are bonded. As a ring structure of this two or more rings, the structure of the following formula is mentioned, for example.

In addition, the bonding position of the said heterocyclic ring is the part from which arbitrary hydrogen atoms contained in each ring were removed.

The heterocyclic group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{N1Z4 , R N2Z4 , R 1Z4 , R 2Z4 , R 3Z4 , R 4Z4 , R 5Z4 , R 6Z4 , R 7Z4 , R 101Z4 and R 102Z4 may have .} .

When the heterocycle contains a nitrogen atom as a constituent element thereof, the hydrocarbon group mentioned above may be bonded to the nitrogen atom as a substituent.

Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 may have the same can be mentioned.

As the heterocyclic group having a substituent represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 , the heterocyclic group having a monovalent or divalent substituent A ring is mentioned, Preferably, the heterocyclic group which has a substituent of group s1 is mentioned, More preferably, the heterocyclic group which has a substituent of group s2 is mentioned. The number of substituents (1st substituent) which the said hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may mutually independently be the same or different. In addition, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

Hereinafter, R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 -CO-R ^102Z4 , -COO-R ^101Z4 , -OCO-R ^102Z4 , -COCO- R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^101Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCO-N (R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON(R ^102Z4 ) ₂ , a halogen atom, -SO ₃ M, and -CO ₂ M will be described.

As -CO-R ^102Z4 , a formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the above formulas, such as a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxyl group, alcohol A carbonyl group (a group derivatized with an agar, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) In the case, the number of carbon atoms is 2 to 41) and in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4, groups corresponding to -CO-R ^102Z4 are mentioned, preferably having 1 to 11 carbon atoms (more Preferably, a hydrocarbon group having 1 to 10 carbon atoms or a carbonyl group to which a derivatized group thereof is bonded (when the carbonyl group is an alkanoyl group, the carbon number is more preferably 2 to 12) and Tables 1Z4 to 8Z4 and Tables 11Z4 to Tables In the compound represented by 16Z4, the group corresponding to -CO-R ^102Z4 , etc. are mentioned.

-COO-R ^101Z4 is a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, Octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, etc. 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) and the group corresponding to -COO-R ^102Z4 in the compound shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4 and an oxycarbonyl group) to which a group derivatized with a diyl)) is bonded, and the like, preferably having 1 to carbon atoms. The group corresponding to -COO-R ^102Z4 in the compound shown in Table 1Z4 - Table 8Z4 and Table 11Z4 - Table 16Z4, the oxycarbonyl group to which the hydrocarbon group of 10 or its derivatization group couple|bonded, etc. are mentioned.

As -OCO-R ^102Z4 , a formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, and the like group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) ) of a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. -OCO- in the compounds shown in the carbonyloxy group (the group derivatized with ) bonded to the carbonyloxy group (when the carbonyloxy group is an acyloxy group, the number of carbon atoms is 2 to 41) and Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4 and the group corresponding to R ^102Z4 , preferably a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a carbonyloxy group to which a derivatized group thereof is bonded (the carbonyloxy group is an acyloxy group). , more preferably 2 to 12 carbon atoms), and groups corresponding to -OCO-R ^102Z4 in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4.

-COCO-R ^102Z4 is methyloxalyl group, ethyloxalyl group, propyloxalyl group, butyloxalyl group, pentyloxalyl group, hexyloxalyl group, (2-ethyl)hexyloxalyl group, heptyloxalyl group group, octyloxalyl group, nonyloxalyl group, decyloxalyl group, undecyloxalyl group, dodecyloxalyl group, icosyloxalyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p - a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, Halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. bonded oxalyl group and Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4 In the compound represented by -COCO-R ^102Z4 , the group etc. are mentioned.

-OR ^{102Z4 is} a hydroxyl group; Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group Group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2 ,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyl group Oxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyl Oxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-e A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof, such as a oxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, and a group represented by the above formula A group (for example, a group derivatized with a carboxy group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) oxy groups and groups corresponding to -OR ^102Z4 in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4, and preferably an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; The group corresponding to -OR ^102Z4 in the compound shown in Table 1Z4 - Table 8Z4 and Table 11Z4 - Table 16Z4, etc. are mentioned.

As -SO ₂ -R ^101Z4 , a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl)hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonyl group sulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc. A hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfa) sulfonyl group) to which a group derivatized with a moyl group), etc.) is bonded, and a group corresponding to -SO ₂ -R ^102Z4 in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4, and the like, preferably carbon number and the group corresponding to -SO ₂ -R ^102Z4 in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4 and the sulfonyl group to which the hydrocarbon group of 1 to 10 or a derivatized group thereof is bonded.

As -SO ₂ N(R ^102Z4 ) ₂ , a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfa Moyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxy group, a sulfo group, A sulfamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z4 to 8Z4 and a group corresponding to -SO ₂ NH(R ^102Z4X ) (provided that R ^102Z4X is the same as R ^102Z4 except that it does not form a hydrogen atom) in the compounds shown in Tables 11Z4 to 16Z4;

N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-dipropylsulfamoyl group, N ,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-disec -Butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group, N,N-dipentylsulfamoyl group, N, N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N,N-diheptylsulfamoyl group, N, N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decylmethylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N ,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, N,N-diphenylsulfamoyl group, etc., and groups represented by the above formulas, etc. of two C1 to C40 (preferably C1 to C20) hydrocarbon groups or derivatized groups thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), 1 to 10 carbon atoms) _A sulfamoyl group substituted with an alkylsulfamoyl group (preferably a group derivatized with an ^{octylsulfamoyl} group) of ) ₂ (provided that R ^102Z4X is the same as R ^102Z4 except that it does not become a hydrogen atom);

Preferably, in the compound shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4 and a sulfamoyl group substituted with a C1 to C1 hydrocarbon group or a derivatized group thereof having 1 or 2 carbon atoms, -SO ₂ N (R ^102Z4 ) The group corresponding to ₂ , etc. are mentioned.

-CON(R ^102Z4 ) ₂ is a carbamoyl group; N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarp Bamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group and N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A sulfamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z4 to 8Z4 and -CONH(R ^102Z4X ) in the compounds shown in Tables 11Z4 to 16Z4 (provided that R ^102Z4X is the same as R ^102Z4 except that it does not form a hydrogen atom), etc.;

N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N ,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec -Butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-dibutylcarbamoyl group, N,N-butyloctylcarbamoyl group, N, N-dipentylcarbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N,N-dihexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N, N-diheptylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N,N-decylmethylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-phenylmethylcarbamoyl group, N,N-diphenylcarbamoyl group and two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably preferably a chlorine atom), a carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) and the like, and shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4. and groups corresponding to -CON(R ^102Z4X ) ₂ (provided that R ^102Z4X is the same as R ^102Z4 except that it does not become a hydrogen atom) in the compound;

Preferably, in the compound shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4 and a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, -CON(R ^102Z4 ) ₂ Corresponds to and the like.

-N(R ^102Z4 ) ₂ is an amino group; N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group , N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, N-dodecylamino group, N- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as an icosylamino group, N-phenylamino group, and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, An amino group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z4 to 8Z4 and Tables a group corresponding to -NH(R ^102Z4X ) (provided that R ^102Z4X is the same as R ^102Z4 except that it does not form a hydrogen atom) in the compounds shown in 11Z4 to Table 16Z4; N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N, N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N-diisobutylamino group, N,N-disec-butylamino group, N,N-ditert-butylamino group, N,N- Butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, N,N-di(1-ethylpropyl)amino group, N,N-dihexylamino group, N,N-di(2-ethyl) ) hexylamino group, N,N-diheptylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N,N-decylmethylamino group, N,N-undecylmethylamino group, N,N-dode A sylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc., and groups represented by the above formulas, such as groups having 1 to 40 carbon atoms (preferably carbon atoms) 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) -N(R ^102Z4X ) ₂ (provided that R ^102Z4X is not a hydrogen atom, except for -N(R 102Z4X ) 2 in the compound shown in the amino group and Table 1Z4 to Table 8Z4 and Table 11Z4 to Table 16Z4) and a group corresponding to R ^102Z4 );

Preferably, in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4, and an amino group substituted with one or two C1 to C10 hydrocarbon groups or derivatized groups thereof, a group corresponding to -N(R ^102Z4 ) ₂ and the like.

-NHCO-R ^{102Z4 is} a formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as amino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group, and groups represented by the above formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. In the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4, -NHCO-R ^102Z4 corresponds to the carbonylamino group to which the group) is bonded (when the carbonylamino group is an acylamino group, the carbon number is 1 to 40) such as to do,

Preferably, a carbonylamino group having 1 to 10 carbon atoms or a derivatized group thereof bonded thereto (when the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10) and Tables 1Z4 to 8Z4 and Tables In the compound shown in 11Z4 - Table 16Z4, the group corresponding to -NHCO-R ^102Z4 , etc. are mentioned.

Examples of -NHCON(R ^102Z4 ) ₂ include the groups listed above, and groups corresponding to -NHCON(R ^102Z4 ) ₂ in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4.

Examples of -NHCOOR ^102Z4 include the groups listed above, and groups corresponding to -NHCOOR ^102Z4 in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4.

Examples of -OCON(R ^102Z4 ) ₂ include the groups listed above and groups corresponding to -OCON(R ^102Z4 ) ₂ in the compounds shown in Tables 1Z4 to 8Z4 and Tables 11Z4 to 16Z4.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are preferable.

As M of -SO ₃ M and -CO ₂ M, a hydrogen atom; Alkali metal atoms, such as a lithium atom, a sodium atom, and a potassium atom, are mentioned, Preferably, a hydrogen atom, a sodium atom, and a potassium atom are mentioned.

The -CO-R ^102Z4 , -COO-R ^102Z4 , -OCO-R ^102Z4 , -COCO-R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^102Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCON(R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON(R ^102Z4 ) ₂ Substituent (first substituent) included in 2 is, Or two or more may be sufficient, and two or more substituents mutually independently may be same or different.

In addition, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

The ring formed by R ^2Z4 and R ^3Z4 , R ^3Z4 and R ^4Z4 , and R ^4Z4 and R ^5Z4 is condensed with the benzene ring of the isoindoline skeleton of the compound represented by formula IZ4. Examples of the condensed ring structure of the benzene ring and the ring formed by R ^2Z4 and R ^3Z4 , R ^3Z4 and R ^4Z4 , and R ^4Z4 and R ^5Z4 include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, and phenylene. nalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, N-methylphthalimide, N-(1-phenylethyl)phthalimide and tetracene hydrocarbon-based condensed ring structures and partial reduction products thereof (eg, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); Indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, perimidine, phenanthroline and phenazine, etc. of nitrogen-containing condensed heterocycles and partial reduction products thereof; Oxygen-containing condensed heterocycles, such as 3-hydrobenzofuran 2-one, and its partial reduction product are mentioned.

When R ^2Z4 and R ^3Z4 , R ^3Z4 and R ^4Z4 , and R ^4Z4 and R ^5Z4 form a ring, the ring may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{N1Z4 , R N2Z4 , R 1Z4 , R 2Z4 , R 3Z4 , R 4Z4 , R 5Z4 , R 6Z4 , R 7Z4 , R 101Z4 and R 102Z4 may have .} . Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , R ^7Z4 , R ^101Z4 and R ^102Z4 may have the same can be mentioned.

When R ^3Z4 and R ^4Z4 form a ring, it is preferable that R ^2Z4 and R ^5Z4 independently represent a hydrogen atom, an amino group and a hydroxyl group.

When R ^2Z4 and R ^3Z4 form a ring, R ^4Z4 and R ^5Z4 preferably do not form a ring, and more preferably R ^4Z4 and R ^5Z4 are hydrogen atoms.

Further, when R ^4Z4 and R ^5Z4 form a ring, R ^2Z4 and R ^3Z4 preferably do not form a ring, and more preferably R ^2Z4 and R ^3Z4 are hydrogen atoms.

In the present invention, R ^1Z4 , R ^6Z4 and R ^7Z4 are preferably a hydrogen atom.

In the present invention, R ^N1Z4 and R ^N2Z4 are, independently of each other, -CO-R ^102Z4 , -COO-R ^101Z4 , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -CO ₂ M or a substituent It is preferable that it is a C1-C40 hydrocarbon group which it may have, It is more preferable that it is a C1-C30 hydrocarbon group which may have a substituent, The C1-C20 hydrocarbon group which may have a substituent is still more preferable, it has a substituent A hydrocarbon group having 1 to 15 carbon atoms which may have a substituent is particularly preferable, and a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent is particularly preferable, and a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent. A hydrocarbon group of -5 is particularly preferred, a methyl group, an ethyl group, or a phenyl group is particularly preferred, and a methyl group or an ethyl group is most preferred. In addition, although R ^N1Z4 and R ^N2Z4 may be the same group or different groups, they are preferably the same group.

From a viewpoint that the phase difference value of the color filter manufactured from the coloring composition becomes small, at least one of ^{R2Z4, R3Z4, R4Z4, and R5Z4 is -CO-R 102Z4 , -COO - R 101Z4} , -OCO-R ^102Z4 , -COCO-R ^102Z4 , -OR ^102Z4 , -SO ₂ -R ^101Z4 , -SO ₂ N(R ^102Z4 ) ₂ , -CON(R ^102Z4 ) ₂ , -N(R ^102Z4 ) ₂ , -NHCO-R ^102Z4 , -NHCO-N(R ^102Z4 ) ₂ , -NHCOOR ^102Z4 , -OCON(R ^102Z4 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, optionally having 1 to carbon atoms having a substituent It is preferable that it is the hydrocarbon group of 40 or the heterocyclic group which may have a substituent,

A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N(R ^102Z4 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of the hydrogen atoms are substituted by fluorine atoms, -NHCO-R ^102Z4 , -OR ^102Z4 , -SO ₃ M or -CO ₂ M more preferably,

It is still more preferable that it is a C1-C40 hydrocarbon group which may have a nitro group or a substituent, and it is still more preferable that it is a nitro group or a tert-butyl group. Alternatively, at least one set of R ^2Z4 and R ^3Z4 , R ^3Z4 and R ^4Z4 , or R ^4Z4 and R ^5Z4 preferably forms a ring.

From a viewpoint that the retardation value of the color filter manufactured from the coloring composition becomes small, at least one of R ^2Z4 , R ^3Z4 , R ^4Z4 , and R ^5Z4 may have a C1-C40 hydrocarbon group which may have a substituent, a halogen atom, -N(R ^102Z4 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z4 , -OR ^102Z4 , -SO ₃ M or -CO ₂ M It is preferable that it is a nitro group or a C1-C40 hydrocarbon group which may have a substituent, It is more preferable that it is a nitro group or a tert- butyl group. Particularly preferably, R ^3Z4 is a nitro group or a tert-butyl group and R ^2Z4 , R ^4Z4 and R ^5Z4 are a hydrogen atom, or R ^2Z4 , R ^3Z4 and R ^5Z4 are a hydrogen atom and R ^4Z4 is a nitro group or tert -It is a butyl group.

As a specific example of the compound IZ4, for example, in the formula IZ4-aa, a substituent shown in Table 1Z4, Table 2Z4, Table 3Z4, Table 4Z4, Table 5Z4, Table 6Z4, Table 7Z4, Table 8Z4 and Table 11Z4 to Table 16Z4 and compounds IZ4-1 to IZ4-769 or alkali metal salts thereof.

B ^a1Z4 B ^a2Z4 is a formula (BB1) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1), a formula (BBO8), a formula (BBO10) , any partial structure represented by the formulas (BBD1) and (BBJ2) is shown. Formula (BB1) to Formula (BB60), Formula (BBK2), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), Formula (BBO8), Formula (BBO10), Formula (BBD1) and Formula (BBJ2) is (BB1) to ( ^BB60 ), Formula ( ^BBK2 ), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), It is equivalent to formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2). B ^a1Z4 and B ^a2Z4 each represent a bond, and B ^a1Z4 is a formula (BB1) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1) , when it is a bond of B ¹ in formulas (BBO8), (BBO10), (BBD1) and (BBJ2), B ^a2Z4 is a bond of B ² , and B ^a1Z4 is a bond of formulas (BB1) to (BB60) , the binding of B2 in Formula (BBK2), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), Formula (BBO8), Formula (BBO10), Formula ( ^BBD1 ), and Formula (BBJ2) In the case of a hand, B ^a2Z4 is a binding hand of B ¹ .

As B ^a1Z4 B ^a2Z4 , Formula (BB1), Formula (BB6), Formula (BB8), Formula (BB11), Formula (BB14), Formula (BB19), Formula (BB37), Formula (BB58), Formula (BBJ2) , the formulas (BBO8) and (BBO10) are preferable, and the formulas (BB1), (BB6) and (BB19) are more preferable.

Each symbol in Table 1Z4, Table 2Z4, Table 3Z4, Table 4Z4, Table 5Z4, Table 6Z4, Table 7Z4, Table 8Z4, and Table 11Z4 to Table 16Z4 indicates the following partial structures. In addition, in the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group,

"Hex" represents a hexyl group, "Oct" represents an octyl group, "2EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group,

"CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ" represents a benzyl group, "NPR" represents a propyl group,

"IPR" represents an isopropyl group, "IBu" represents an isobutyl group, "EOE" represents -CH ₂ CH ₂ OCH ₂ CH ₃ , "ALL" represents an allyl group, and "HYE" represents 2-hydroxy represents an ethyl group, "COM" represents -CO-CH ₃ , "COE" represents -COO-CH ₂ CH ₃ , "OCM" represents -OCO-CH ₃ , and "OME" represents -O-CH ₃ is represented, "SOT" represents a tosyl group, "SNH" represents -SO ₂ NH-CH ₂ CH(CH ₂ CH ₃ )((CH ₂ ) ₃ CH ₃ ), "SN2" is -SO ₂ Represents N(CH ₃ )((CH ₂ ) ₇ CH ₃ ), "CNM" represents -CONHCH ₃ , "CN2" represents -CON(CH ₃ )C ₆ H ₅ , and "NPH" is -NHC ₆ H ₅ , "NOT" represents -N((CH ₂ ) ₇ CH ₃ ) ₂ , "NCO" represents -NHCO((CH ₂ ) ₄ CH ₃ ), "F" represents a fluorine atom "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO2" represents a nitro group, "SUA" represents -SO ₃ H, and "CBA"" represents -CO ₂ H, "CHO" represents -CHO, "OCH" represents -OCOH, "OH" represents -OH, "SFM" represents -SO ₂ NH ₂ , and "CBM"" represents -CONH ₂ , "NH2" represents -NH ₂ , "NCH" represents -NHCOH, and * represents a bond.

In addition, in a table|surface, the partial structure represented by a following formula is represented by the code|symbol attached below the said structure.

[Table 1Z4]

[Table 2Z4]

[Table 3Z4]

[Table 4Z4]

[Table 5Z4]

[Table 6Z4]

[Table 7Z4]

[Table 8Z4]

[Table 11Z4]

[Table 12Z4]

[Table 13Z4]

[Table 14Z4]

[Table 15Z4]

[Table 16Z4]

For example, compound IZ4-1 is a compound represented by Formula IZ4-1.

As the compound IZ4, compound IZ4-1 to compound IZ4-234 and compound IZ4-321 to compound IZ4-769 are preferable, and compound IZ4-1 to compound IZ4-234 and compound IZ4-321 to compound IZ4-711 are more preferable. , more preferably compound IZ4-1 to compound IZ4-234, even more preferably compound IZ4-1 to compound IZ4-174, particularly preferred compound IZ4-1 to compound IZ4-117,

Compound IZ4-1 to compound IZ4-2, compound IZ4-40 to compound IZ4-41, and compound IZ4-79 to compound IZ4-80 are particularly preferred.

As a specific example of compound IZ4, Table 1Z4, Table 2Z4, Table 3Z4, Table 4Z4, Table 5Z4, Table 6Z4, Table 7Z4, and Table 8Z4 and Table 11Z4 to Table 16Z4 to 1 to 3 hydrogen atoms contained in the compounds shown - A compound in which SO ₃ M or —CO ₂ M is substituted may also be mentioned. For example, a compound in which 1 to 3 sulfo groups are bonded to compound IZ4-1 of Table 1Z4 is represented by the following structure. However, in the formula, -(SO ₃ H) shall mean that the hydrogen atom in any of the compounds IZ4-1 of Table 1Z4 is substituted.

In the present invention, compounds IZ4-1 to compound IZ4-234 and compound IZ4-321 to compound IZ4-769 are preferably compounds in which one to three -SO ₃ M or -CO ₂ M are bonded, and compound IZ4-1 -Compound IZ4-234 and compound IZ4-321 -Compound IZ4-711 is more preferably a compound in which 1-3 pieces of -SO ₃ M or -CO ₂ M are bonded;

Compound IZ4-1 to compound IZ4-234 is more preferably a compound in which 1-3 pieces of -SO ₃ M or -CO ₂ M are bonded,

Compound IZ4-1 to compound IZ4-174 is more preferably a compound in which one to three -SO ₃ M or -CO ₂ M is bonded,

Compounds in which one to three -SO ₃ M or -CO ₂ M are bonded to compound IZ4-1 to compound IZ4-117 are particularly preferred,

Compound IZ4-1 to compound IZ4-2, compound IZ4-40 to compound IZ4-41, and compound IZ4-79 to compound IZ4-80 are a compound in which one to three -SO ₃ M or -CO ₂ M is bonded. Especially preferred.

As compound (IZ4), in formula (IZ4), R ^N1Z4 and R ^N2Z4 are each independently -CO-R ^102Z4 , -COO-R ^101Z4 , -CON(R ^102Z4 ) ₂ , or -SO ₃ M or -CO ₂ M is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of, R ^1Z4 is a hydrogen atom, even if it has a substituent selected from the group consisting of -SO ₃ M or -CO ₂ M A hydrocarbon group having 1 to 20 carbon atoms, -SO ₃ M or -CO ₂ M,

R ^2Z4 to R ^5Z4 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102Z4 ) ₂ , a nitro group, or a fluorine atom having 1 carbon atom in which all or part of the hydrogen atoms are substituted to 20 hydrocarbon group, -NHCO-R ^102Z4 , -OR ^102Z4 , -SO ₃ M or -CO ₂ M, R ^6Z4 and R ^7Z4 are, independently of each other, a hydrogen atom, -SO ₃ M or -CO ₂ M A hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of, -SO ₃ M or -CO ₂ M, R ^102Z4 is a hydrogen atom, or a group consisting of -SO ₃ M or -CO ₂ M A hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from, R ^101Z4 is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M or -CO ₂ M, M is preferably a compound of a hydrogen atom or an alkali metal atom, and R ^N1Z4 and R ^N2Z4 are, independently of each other, -CO-R ^102Z4 , -CON(R ^102Z4 ) ₂ , or -SO ₃ M or -CO ₂ M A hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of, R ^1Z4 is a hydrogen atom, R ^2Z4 to R ^5Z4 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms , a halogen atom, -N(R ^102Z4 ) ₂ , a nitro group, a hydrocarbon group having 1 to 10 carbon atoms in which all or part of a hydrogen atom is substituted with a fluorine atom, -NHCO-R ^102Z4 , -OR ^102Z4 , -SO ₃ M or - CO ₂ M,

R ^6Z4 and R ^7Z4 are the same group and are a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M;

R ^102Z4 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, R ^101Z4 is -SO ₃ M and -CO ₂ M It is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of, and M is more preferably a compound of a hydrogen atom or an alkali metal atom,

R ^N1Z4 and R ^N2Z4 each independently represent 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -CO-R ^102Z4 , -CON(R ^102Z4 ) ₂ , or -SO ₃ M or -CO ₂ M is a hydrocarbon group of

R ^1Z4 is a hydrogen atom, R ^2Z4 to R ^5Z4 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, —N(R ^102Z4 ) ₂ , a nitro group, a trifluoromethyl group, -OR ^102Z4 , -SO ₃ M or -CO ₂ M,

R ^6Z4 and R ^7Z4 are the same group and are a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and R ^102Z4 is a hydrogen atom or a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M; It is a hydrocarbon group having 1 to 10 carbon atoms which may be present,

R ^101Z4 is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, and M is a hydrogen atom or an alkali metal atom, more preferably a compound.

Compound IZ4, when R ^1Z4 is a hydrogen atom, reacts a compound represented by the formula pt1Z4 (hereinafter sometimes referred to as a phthalonitrile compound) with a compound represented by the formula pt2Z4 (hereinafter sometimes referred to as an alkoxide compound) After the reaction, it can be prepared by further reacting the compound represented by the formula pt3Z4 with the compound represented by the formula pt4Z4 in the presence of an acid. Further, when R ^1Z4 is other than a hydrogen atom, compound IZ4 can be produced by further reacting with a compound represented by the formula pt5Z4.

[of formula pt1Z4, formula pt2Z4, formula pt3Z4, formula pt4Z4, formula pt5Z4, and formula IZ4, wherein R ^N1Z4 , R ^N2Z4 , R ^1Z4 , R ^2Z4 , R ^3Z4 , R ^4Z4 , R ^5Z4 , R ^6Z4 , and R ^7Z4 are has the same meaning as R ^14Z4 represents an alkyl group having 1 to 20 carbon atoms. M ^1Z4 represents an alkali metal atom. LG represents a halogen atom, a methanesulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group.]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ^14Z4 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group, and preferably a C1 group. -6 alkyl groups are mentioned.

Examples of the alkali metal atom represented by M ^1Z4 include a lithium atom, a sodium atom and a potassium atom. The usage-amount of an alkoxide compound is 0.1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 0.2-5 mol, More preferably, it is 0.3-3 mol, More preferably, it is 0.4-2 mol. it's a mall

The usage-amount of compound pt3Z4 is 1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 1-5 mol, More preferably, it is 1-3 mol, More preferably, it is 1-2 mol. am.

The usage-amount of compound pt4Z4 is 1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 1-5 mol, More preferably, it is 1-3 mol, More preferably, it is 1-2 mol. am.

Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; and carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid These are mentioned, More preferably, acetic acid is mentioned.

The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, still more preferably 1 to 6 moles with respect to 1 mole of the phthalonitrile compound.

The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z4, and the compound pt4Z4 is usually carried out in the presence of a solvent.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N ,N-dimethylformaldehyde, N-methylpyrrolidone and dimethyl sulfoxide, and more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1- octanol, acetone, methylene chloride, chloroform, N,N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide are exemplified, particularly preferably water, acetonitrile, methanol, ethanol and 2-propanol. can be heard

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of phthalonitrile compounds. Reaction temperature is 0-200 degreeC normally, Preferably it is 0-100 degreeC, More preferably, it is 0-70 degreeC, More preferably, it is 0-50 degreeC. The reaction time is usually 0.5 to 300 hours.

The amount of the compound pt5Z4 to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 mole to 1 mole of the compound IZ4 in which R ^1Z4 is a hydrogen atom. 1 to 2 moles.

When the compound pt5Z4 is reacted, it is preferable that a base coexist. Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; organometallic compounds such as butyllithium, tert-butyllithium and phenyllithium; Inorganic bases, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, are mentioned.

The amount of the base used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 10 moles, with respect to 1 mole of compound IZ4 in which R ^1Z4 is a hydrogen atom. 2 moles.

The reaction of the compound pt5Z4 is usually carried out in the presence of a solvent. A solvent can be selected from the range similar to the above.

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of compound IZ4 whose R ^<1Z4 is a hydrogen atom. The reaction temperature of the compound pt5Z4 is usually -90 to 200°C, preferably -80 to 100°C, more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

When the compound IZ4 does not have a sulfo group or -SO ₃ M ² , a sulfo group or -SO ₃ M ²² can be introduced by reacting the compound IZ4 with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid.

M ²² represents an alkali metal atom. Examples of the alkali metal atom represented by M ²² include a lithium atom, a sodium atom and a potassium atom.

The amount of SO ₃ used in the fuming sulfuric acid is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, still more preferably 5 to 25 moles with respect to 1 mole of compound IZ4. am.

The amount of sulfuric acid used in the fuming sulfuric acid is usually 1-200 moles, preferably 10-100 moles, more preferably 10-75 moles, still more preferably 10-50 moles with respect to 1 mole of compound IZ4. .

The usage-amount of chlorosulfonic acid is 1-500 mol normally with respect to 1 mol of compound IZ4, Preferably it is 10-300 mol, More preferably, it is 10-200 mol, More preferably, it is 10-150 mol.

The reaction temperature for sulfonation is usually -20 to 200°C, preferably -10 to 100°C, and more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

The method for taking out the compound IZ4 from the reaction mixture is not particularly limited, and can be taken out by various known methods. For example, after completion of the reaction, the compound IZ4 can be taken out by filtering the reaction mixture. After filtration, the obtained residue may be subjected to column chromatography, recrystallization, or the like. Further, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and then purified by column chromatography.

<Compound IZ5>

The compound IZ5 is represented by the formula IZ5.

[In formula IZ5, R ^N1Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO-N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , halogen atom , a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , and R ^7Z5 are, independently of each other, a hydrogen atom, -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO -R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO- N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and R ^4Z5 and R ^5Z5 may be bonded to each other to form a ring, R ^2Z5 , R ^3Z5 , R ^4Z5 and At least one of R ^5Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO-N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , halogen atom, cya a no group, a nitro group, -SO ₃ M, -CO ₂ M, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and at least one set of R ^4Z5 and R ^5Z5 is bonded to form a ring.

R ^101Z5 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102Z5 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. When two or more R ^101Z5 , R ^102Z5 and M exist, they may be same or different. The broken line indicates the E or Z body.]

The hydrocarbon group which may have a substituent represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 has 1 to 40 carbon atoms, preferably It is 1-30, More preferably, it is 1-20, More preferably, it is 1-15, Especially preferably, it is 1-10, Especially preferably, it is 1-5.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 include a methyl group, an ethyl group, a propyl group, a butyl group, straight-chain alkyl groups such as pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, heptadecyl group, octadecyl group and icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl)pentyl group, (2- methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group and (3-ethyl) heptyl group branched chain alkyl groups and the like; Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-pro alkenyl groups such as phenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl; and the like. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, still more preferably is 1 to 8, particularly preferably 1 to 5. Especially, it is especially preferable that it is a C1-C10, More preferably, it is a C1-C8 linear or branched alkyl group, and a methyl group, an ethyl group, and a tert- butyl group are especially preferable.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 include cyclopropyl group, 1-methylcyclopropyl group , cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethyl Cyclohexyl 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-dimethylcyclo Hexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclo cycloalkyl groups such as a hexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; cycloalkenyl groups such as a cyclohexenyl group (eg, cyclohexa-2-ene, cyclohexa-3-ene), a cycloheptenyl group, and a cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane, etc. are mentioned. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 4 to 20 carbon atoms, still more preferably 4 to 15 carbon atoms, and particularly More preferably, it is 5-15, Most preferably, it is 5-10. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

Examples of the aromatic hydrocarbon group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 include a phenyl group, an o-tolyl group, a m-tolyl group, and p- tolyl 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, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 4-ethylphenyl group, 4-butyl Phenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-vinylphenyl group, 1-naphthyl group, 2 -naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group and anthryl group, pyrenyl group aromatic hydrocarbon groups, such as; and the like. Carbon number of an aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-15.

The hydrocarbon group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 is the above-mentioned hydrocarbon group (for example, an aromatic hydrocarbon group, a chain hydrocarbon group group and at least one of an alicyclic hydrocarbon group) may be combined; arylalkenyl groups such as a phenylethenyl group (phenylvinyl group); Aryl alkynyl groups, such as a phenylethynyl group; a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; A cyclohexylmethylphenyl group, a benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. are mentioned.

The group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 is a hydrocarbon group (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group). ) combined, for example, a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, The alkyl group to which one or more alicyclic hydrocarbon groups, such as an adamantylmethyl group, couple|bonded may be sufficient. These carbon number becomes like this. Preferably it is 4-30, More preferably, it is 6-30, More preferably, it is 6-20, More preferably, it is 4-20, More preferably, it is 4-15, Especially preferably, it is 6-15.

The hydrocarbon group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 may have a substituent. The substituent may be monovalent or divalent. The divalent substituent preferably has two bonds bonded to the same carbon atom to form a double bond.

The monovalent substituent is methoxy, ethoxy, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl ) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy, 1- Methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6- Dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyl group Oxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyloxy group, 3,4-dicyanophenyloxy group 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group, and groups represented by the following formulas A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (eg, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfa having 1 to 10 carbon atoms) an oxy group bonded to one side of a moyl group (preferably a group derivatized with an octylsulfamoyl group) or the like;

Methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethyl)hexylthio group, heptylthio group, octylthio group, nonylthio group , a sulfanyl group to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as decylthio group, undecylthio group, dodecylthio group, icosylthio group, phenylthio group and o-tolylthio group;

an epoxy group, an oxetanyl group, a tetrahydrofuryl group, a tetrahydropyranyl group;

formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the following formulas, such as a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivatized group thereof (for example, a carboxy group , a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) When it is set as a canoyl group, carbon number becomes like this. Preferably it is 2-12);

Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group , decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, icosyloxycarbonyl group, phenyloxycarbonyl group, o-tolyloxycarbonyl group, etc. to 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) ), a group derivatized with an oxycarbonyl group to which) is bonded;

amino group; N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diiso group Propylamino group, N-butylamino group, N,N-dibutylamino group, N-isobutylamino group, N,N-diisobutylamino group, N-sec-butylamino group, N,N-disec-butylamino group, N- tert-butylamino group, N,N-ditert-butylamino group, N-pentylamino group, N,N-dipentylamino group, N-(1-ethylpropyl)amino group, N,N-di(1-ethylpropyl)amino group , N-hexylamino group, N,N-dihexylamino group, N-(2-ethyl)hexylamino group, N,N-di(2-ethyl)hexylamino group, N-heptylamino group, N,N-diheptylamino group, N-octylamino group, N,N-dioctylamino group, N-nonylamino group, N,N-dinonylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N -Propylmethylamino group, N,N-isopropylmethylamino group, N,N-butylmethylamino group, N-decylamino group, N,N-decylmethylamino group, N-undecylamino group, N,N-undecylmethylamino group, N-dodecylamino group, N,N-dodecylmethylamino group, N-icosylamino group, N,N-icosylmethylamino group, N,N-tert-butylmethylamino group, N,N-phenylmethylamino group, and the like; One or two hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), such as a group represented by the following formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a preferably a chlorine atom), an amino group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

sulfamoyl group; N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N,N-diethylsulfamoyl group, N-propylsulfamoyl group, N,N-dipropylsulfamoyl group, N-isopropylsulfamoyl group, N,N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N,N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N,N-diiso Butylsulfamoyl group, N-sec-butylsulfamoyl group, N,N-disec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N-pentyl group sulfamoyl group, N,N-dipentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N, N-dihexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N,N-diheptylsulfamo Diyl, N-octylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-octylmethylsulfamoyl group, N-nonylsulfamoyl group, N,N-dinonylsulfamoyl group, N-phenylsulfa Moyl group, N,N-diphenylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-butylmethyl Sulfamoyl group, N-decylsulfamoyl group, N,N-decylmethylsulfamoyl group, N-undecylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N-dodecylsulfamoyl group, N, N-dodecylmethylsulfamoyl group, N-icosylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, etc. , and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a sulfamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms), such as amino groups, decanoylamino groups, undecanoylamino groups, dodecanoylamino groups, henicosanoylamino groups and benzoylamino groups, and groups represented by the following formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. a carbonylamino group to which the group) is bonded (when the carbonylamino group is an alkanoylamino group, the carbon number is preferably 1 to 12);

hydroxyl group; Halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;

carboxyl group; —CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); a sulfo group, —SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); nitro group; cyano group;

formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpentanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, nonano 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), such as yloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, and groups represented by the following formulas ) of a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. a carbonyloxy group to which a derivatized group) is bonded (when the carbonyloxy group is an alkanoyloxy group, the carbon number is preferably 1 to 10);

Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl)hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, unde A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a silsulfonyl group, a dodecylsulfonyl group, an icosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, and a group represented by the following formula or a derivatized group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. ) is a sulfonyl group bonded;

carbamoyl group; N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N,N-diethylcarbamoyl group, N-propylcarbamoyl group, N,N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N,N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N,N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N,N-diiso Butylcarbamoyl group, N-sec-butylcarbamoyl group, N,N-disec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N-pentyl group Carbamoyl group, N,N-dipentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N, N-dihexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N,N-diheptylcarbamo group Diyl, N-octylcarbamoyl group, N,N-dioctylcarbamoyl group, N-nonylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-octylbutylcarbamoyl group, N,N- dinonylcarbamoyl group, N-phenylcarbamoyl group, N,N-diphenylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-isopropylmethyl Carbamoyl group, N,N-butylmethylcarbamoyl group, N-decylcarbamoyl group, N,N-decylmethylcarbamoyl group, N-undecylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N-dodecylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N-icosylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, One or two C1-C20 (preferably C1-C10) hydrocarbon groups, such as N,N-phenylmethylcarbamoyl group, and the group represented by the following formula, or its derivatized group (for example, a carboxy group , a carbamoyl group substituted with a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group);

Trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluoro All hydrogen atoms such as octyl group, perfluorononyl group, perfluorodecyl group, perfluorodecyl group, perfluorododecyl group, perfluoroicosyl group, perfluorocyclohexyl group and perfluorophenyl group a hydrocarbon group having 1 to 20 carbon atoms substituted with a fluorine atom;

Perfluoroethylmethyl group, perfluoropropylmethyl group, perfluoroisopropylmethyl group, perfluorobutylmethyl group, perfluoropentylmethyl group, perfluorohexylmethyl group, perfluoroheptylmethyl group, perfluorooctylmethyl group, purple A linear or branched chain having 1 to 20 carbon atoms in which all hydrogen atoms, such as a luoronylmethyl group, perfluorodecylmethyl group, perfluorodecylmethyl group, perfluorododecylmethyl group, and perfluoroicosylmethyl group, are substituted with fluorine atoms a hydrocarbon group having 1 to 20 carbon atoms substituted with an alkyl group of;

Part of hydrogen atoms such as 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, and 2,4,6-trifluorophenyl group are substituted with fluorine having 1 to 20 carbon atoms (preferably from 1 to 20 carbon atoms) The hydrocarbon group of 10);

-CO-SH, -CO-S-CH ₃ , -CO-S-CH ₂ CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₃ and -CO-S-CH ₂ -CH ₂ -CH ₂ a thiocarbonyl group bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as -CH ₃ , a thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms such as -CO-SC ₆ H ₅ ;

*-COCO-R represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), etc.) of qi;

*-NRCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivatized group thereof (For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivatized group thereof (For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-NRCOOR represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivatized group thereof ( For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OP(O)(OR) ₂ such as *-OP(O)(OCH ₃ ) ₂ (wherein R is a hydrogen atom and a hydrocarbon group having 1 to 20 carbon atoms (for example, among the hydrocarbon groups listed above) those satisfying 1 to 20 carbon atoms), or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a chlorine atom) octylsulfamoyl group)), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-SiR ₃ (such as *-Si(CH ₃ ) ₃ , *-Si(CH ₂ CH ₃ ) ₃ , *-Si(C ₆ H ₅ ) ₃ and *-Si(CH(CH ₃ ) ₂ ) ₃ , etc. In the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), wherein R may be the same as or different from each other and may combine with each other to form a ring); and the like.

Examples of the divalent substituent include an imino group substituted with an oxo group, a thioxo group, an imino group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted with an aryl group having 6 to 20 carbon atoms. can Examples of the imino group substituted with the alkyl group include CH ₃ -N=, CH ₃ -CH ₂ -N=, CH ₃ -(CH ₂ ) ₂ -N= and CH ₃ -(CH ₂ ) ₃ -N=, etc. there is. Examples of the imino group substituted with the aryl group include C ₆ H ₅ -N=.

As a substituent of a C1-C40 hydrocarbon group, Preferably, the substituent of group s1 is mentioned. The derivatized group shown below is preferably a group derivatized with a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) or the like. Do.

[group s1]

an oxy group in which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; halogen atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms in which all of the hydrogen atoms are substituted with fluorine atoms, a linear or branched alkyl group having 1 to 20 carbon atoms; a hydrocarbon group having 1 to 20 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo.

As a substituent of a C1-C40 hydrocarbon group, More preferably, the substituent of group s2 is mentioned.

[group s2]

an oxy group in which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms;

sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; a fluorine atom, a chlorine atom, a bromine atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); -SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom;

a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo.

As the hydrocarbon group having 1 to 40 carbon atoms having a substituent represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 , a monovalent or divalent substituent is and a hydrocarbon group having 1 to 40 carbon atoms, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms having a monovalent or divalent substituent, and 3 to 30 carbon atoms having a monovalent or divalent substituent. A saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group having 6 to 30 carbon atoms having a monovalent or divalent substituent, or a group combining hydrocarbon groups, and a group having 1 to 30 carbon atoms having a monovalent or divalent substituent;

More preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, and a carbon number having a substituent in group s1 It is a group combining 6-20 aromatic hydrocarbon groups or hydrocarbon groups, and a C1-C20 group which has a substituent of group s1 is mentioned,

Particularly preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, a carbon number having a substituent of group s2 It is a group combining the aromatic hydrocarbon group or hydrocarbon group of 6-15, and the group of C1-C15 which has a substituent of group s2 is mentioned.

The heterocyclic group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 may be monocyclic or polycyclic, preferably heterocyclic as a component of the ring. It is a heterocycle containing atoms. As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned.

The heterocyclic group preferably has 3 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, still more preferably 3 to 20 carbon atoms, still more preferably 3 to 18 carbon atoms, still more preferably 3 to 15 carbon atoms. and particularly preferably 3 to 14.

Examples of the heterocycle containing a nitrogen atom include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrroles such as 2,5-dimethylpyrrole, pyrazoles such as 2-methylpyrazole and 3-methylpyrazole, and 5-membered rings such as imidazole, 1,2,3-triazole and 1,2,4-triazole systemic unsaturated heterocycle;

pyrimidines such as pyridine, pyridazine and 6-methylpyrimidine; 6-membered ring unsaturated heterocycles such as pyrazine and 1,3,5-triazine;

Quinox such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline condensed bicyclic heterocycles such as saline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperizine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and the like.

Examples of the heterocycle containing an oxygen atom include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane. ; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; 5-membered ring unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran; Condensed bicyclic heterocycles, such as benzopyran, such as 1-benzofuran and 4-methylbenzopyran, benzodioxole, chroman, and isochroman; Condensed tricyclic heterocycles, such as xanthene and dibenzofuran; and the like.

As a heterocyclic ring containing a sulfur atom, 5-membered ring system saturated heterocycles, such as dithiolane;

6-membered ring-based saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl 1,3-dithiane;

5-membered ring unsaturated heterocycles, such as thiophene, such as 3-methylthiophene and 2-carboxythiophene, benzothiopyran, such as 4H-thiopyran and benzotetrahydrothiopyran;

Condensed bicyclic heterocycles, such as benzothiophene; condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.

Examples of the heterocycle containing a nitrogen atom and an oxygen atom include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone. Summons; Monocyclic unsaturated heterocycles, such as isoxazole, such as oxazole, such as 4-methyloxazole, 2-methylisoxazole, and 3-methylisoxazole; Condensed bicyclic heterocyclic rings, such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline; condensed tricyclic heterocycles such as phenoxazine; and the like.

As a heterocyclic ring containing a nitrogen atom and a sulfur atom, Monocyclic heterocyclic rings, such as thiazole, such as 3-methylthiazole and 2, 4- dimethylthiazole; Condensed bicyclic heterocycles, such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine; and the like.

The heterocyclic ring may be a group in which the above-mentioned hydrocarbon groups are combined, and examples thereof include a tetrahydrofurylmethyl group and the like.

The heterocycle may be represented by the following formula.

The heterocyclic group may be a heterocyclic group formed by bonding two or more of R ^1Z5 to R ^5Z5 . Such a heterocyclic group has a ring structure of two or more rings together with the benzene ring to which R ^1Z5 to R ^5Z5 are bonded. As a ring structure of this two or more rings, the structure of the following formula is mentioned, for example.

The bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is removed.

The heterocyclic group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{N1Z5 , R 1Z5 , R 2Z5 , R 3Z5 , R 4Z5 , R 5Z5 , R 6Z5 , R 7Z5 , R 101Z5 and R 102Z5 may have} . Moreover, when the said heterocyclic ring contains the nitrogen atom as its structural element, the hydrocarbon group mentioned above may couple|bond with this nitrogen atom as a substituent. Preferred examples of the substituent include the same as preferred substituents which the hydrocarbon group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 may have can

Examples of the heterocyclic group having a substituent represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 include heterocyclic groups having a monovalent or divalent substituent. and preferably a heterocyclic group having a substituent of group s1, more preferably a heterocyclic group having a substituent of group s2.

The number of substituents (1st substituent) which the said hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may mutually independently be the same or different. As for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

Hereinafter, -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 of R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , and R ^7Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO-N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , a halogen atom, -SO ₃ M, and -CO ₂ M will be described.

As -CO-R ^102Z5 , a formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the above formulas, such as a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxyl group, alcohol A carbonyl group (a group derivatized with an agar, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) In the case, the number of carbon atoms is 2 to 41) and in the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5, a group corresponding to -CO-R ^102Z5 is mentioned, preferably having 1 to 11 carbon atoms (more Preferably, a carbonyl group having 1 to 10 carbon atoms or a derivatized group thereof bonded thereto (when the carbonyl group is an alkanoyl group, the carbon number is more preferably 2 to 12), and Tables 1Z5 to 7Z5 and 10Z5 to In the compound shown in Table 13Z5, the group corresponding to -CO-R ^102Z5 , etc. are mentioned.

-COO-R ^101Z5 is a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, Octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, etc. 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) and the group corresponding to -COO-R ^102Z5 in the compound shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5 and an oxycarbonyl group) to which a group derivatized with a diyl)) is bonded, and the like, preferably having 1 to carbon atoms. The group corresponding to -COO-R ^102Z5 in the compound shown in Table 1Z5 - Table 7Z5 and Table 10Z5 - Table 13Z5 and the oxycarbonyl group to which the hydrocarbon group of 10 or its derivatization group couple|bonded, etc. are mentioned.

As -OCO-R ^102Z5 , a formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, etc., and groups represented by the above formulas having 1 to 40 carbon atoms (preferably from 1 to carbon atoms). 20) of a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) In the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5, and a carbonyloxy group to which a carbonyloxy group (a group derivatized with, etc.) is bonded (when the carbonyloxy group is an acyloxy group, the number of carbon atoms is 2 to 41) - and a group corresponding to OCO-R ^102Z5 , preferably a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a carbonyloxy group to which a derivatized group thereof is bonded (the carbonyloxy group is an acyl group). In the case of an oxy group, the number of carbon atoms is more preferably 2 to 12), and a group corresponding to -OCO-R ^102Z5 in the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5.

-COCO-R ^102Z5 is methyloxalyl group, ethyloxalyl group, propyloxalyl group, butyloxalyl group, pentyloxalyl group, hexyloxalyl group, (2-ethyl)hexyloxalyl group, heptyloxalyl group group, octyloxalyl group, nonyloxalyl group, decyloxalyl group, undecyloxalyl group, dodecyloxalyl group, icosyloxalyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p - a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxy group, Halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. bonded oxalyl group and Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5 In the compound represented by -COCO-R ^102Z5 , the group etc. are mentioned.

Examples of the -OR ^102Z5 group include a hydroxy group; Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group Group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2 ,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyl group Oxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyl Oxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-e A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof, such as a oxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, and a group represented by the above formula A group (for example, a group derivatized with a carboxy group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) oxy groups and groups corresponding to -OR ^102Z5 in the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5, and preferably an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; The group corresponding to -OR ^102Z5 in the compound shown in Table 1Z5 - Table 7Z5 and Table 10Z5 - Table 13Z5, etc. are mentioned.

As -SO ₂ -R ^101Z5 , a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl)hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonyl group sulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc. A hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfa) and a group corresponding to -SO ₂ -R ^101Z5 in the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5 and a sulfonyl group) to which a group derivatized with a moyl group)) is bonded, and the like, preferably having a carbon number The group corresponding to -SO ₂ -R ^101Z5 in the compounds shown in Tables 1Z5 - 7Z5 and Tables 10Z5 - 13Z5 and the sulfonyl group to which the hydrocarbon group of 1-10 or its derivatization group is bonded is mentioned.

As -SO ₂ N(R ^102Z5 ) ₂ , a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfa Moyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A sulfamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z5 to 7Z5 and a group corresponding to -SO ₂ NH(R ^102Z5X ) (provided that R ^102Z5X is the same as R ^102Z5 except that it does not form a hydrogen atom) in the compounds shown in Tables 10Z5 to 13Z5;

N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-dipropylsulfamoyl group, N ,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-disec -Butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group, N,N-dipentylsulfamoyl group, N, N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N,N-diheptylsulfamoyl group, N, N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decylmethylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N ,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, N,N-diphenylsulfamoyl group, etc., and groups represented by the above formulas, etc. of two C1 to C40 (preferably C1 to C20) hydrocarbon groups or derivatized groups thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), 1 to 10 carbon atoms) _A sulfamoyl group substituted with an alkylsulfamoyl group (preferably a group derivatized with an ^{octylsulfamoyl} group, etc.) of ) ₂ (provided that R ^102Z5X is the same as R ^102Z5 except that it does not become a hydrogen atom);

In the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5 and a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, -SO ₂ N(R ^102Z5 ) ₂ and groups corresponding to .

-CON(R ^102Z5 ) ₂ is a carbamoyl group; N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarp Bamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group and N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z5 to 7Z5 and a group corresponding to -CONH(R ^102Z5X ) (provided that R ^102Z5X is the same as R ^102Z5 except that it does not form a hydrogen atom) in the compounds shown in Tables 10Z5 to 13Z5;

N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N ,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec -Butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-dibutylcarbamoyl group, N,N-butyloctylcarbamoyl group, N, N-dipentylcarbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N,N-dihexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N, N-diheptylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N,N-decylmethylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-phenylmethylcarbamoyl group, N,N-diphenylcarbamoyl group and two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably preferably a chlorine atom), a carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group), and the like, and shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5 In the compound, the group corresponding to -CON(R ^102Z5X ) ₂ (R ^102Z5X is the same as R ^102Z5 except that it does not become a hydrogen atom), etc. are mentioned;

Preferably, in the compound shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5 and a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof, -CON(R ^102Z5 ) ₂ Corresponds to and the like.

-N(R ^102Z5 ) ₂ is an amino group; N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group , N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, N-dodecylamino group, N- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as an icosylamino group, N-phenylamino group, and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, An amino group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z5 to 7Z5 and Tables In the compounds shown in 10Z5 to Table 13Z5, a group corresponding to -NH(R ^102Z5X ) (R ^102Z5X is the same as R ^102Z5 except that it does not form a hydrogen atom);

N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N, N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N-diisobutylamino group, N,N-disec-butylamino group, N,N-ditert-butylamino group, N,N- Butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, N,N-di(1-ethylpropyl)amino group, N,N-dihexylamino group, N,N-di(2-ethyl) ) hexylamino group, N,N-diheptylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N,N-decylmethylamino group, N,N-undecylmethylamino group, N,N-dode A sylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc., and groups represented by the above formulas, such as groups having 1 to 40 carbon atoms (preferably carbon atoms) 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) -N(R ^102Z5X ) ₂ (provided that R ^102Z5X is not a hydrogen atom, except that -N(R 102Z5X ) 2 in the compound shown in the amino group and Table 1Z5 to Table 7Z5 and Table 10Z5 to Table 13Z5) and a group corresponding to R ^102Z5 );

Preferably, in the compound shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5 and an amino group substituted with one or two C1 to C10 hydrocarbon groups or derivatized groups thereof, a group corresponding to -N(R ^102Z5 ) ₂ and the like.

-NHCO-R ^{102Z5 is} a formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as amino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group, and groups represented by the above formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. In the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5, -NHCO-R ^102Z5 corresponds to the carbonylamino group to which the group) is bonded (when the carbonylamino group is an acylamino group, the carbon number is 1 to 40) such as to do,

Preferably, a carbonylamino group having 1 to 10 carbon atoms or a derivatized group thereof bonded thereto (when the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10) and Tables 1Z5 to 7Z5 and Tables The group corresponding to -NHCO-R ^102Z5 in the compound shown in 10Z5 - Table 13Z5, etc. are mentioned.

Examples of -NHCON(R ^102Z5 ) ₂ include the groups listed above, and groups corresponding to -NHCON(R ^102Z5 ) ₂ in the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5.

Examples of -NHCOOR ^102Z5 include the groups listed above and groups corresponding to -NHCOOR ^102Z5 in the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5.

Examples of -OCON(R ^102Z5 ) ₂ include the groups listed above and groups corresponding to -OCON(R ^102Z5 ) ₂ in the compounds shown in Tables 1Z5 to 7Z5 and Tables 10Z5 to 13Z5.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are preferable.

As M of -SO ₃ M and -CO ₂ M, a hydrogen atom; Alkali metal atoms, such as a lithium atom, a sodium atom, and a potassium atom, are mentioned, Preferably, a hydrogen atom, a sodium atom, and a potassium atom are mentioned.

The -CO-R ^102Z5 , -COO-R ^102Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^102Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCON(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ Substituent (first substituent) included in 2 is, Or two or more may be sufficient, and two or more substituents mutually independently may be same or different.

Moreover, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

The ring formed by R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and R ^4Z5 and R ^5Z5 is condensed with the benzene ring of the isoindoline skeleton of the compound represented by the formula IZ5. Examples of the condensed ring structure of the benzene ring and the ring formed by R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and R ^4Z5 and R ^5Z5 include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, and phenalene. , phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, N-methylphthalimide, N-(1-phenylethyl)phthalimide, tetracene, etc. of hydrocarbon-based condensed ring structures and partially reduced products thereof (eg, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); Indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, perimidine, phenanthroline and phenazine, etc. of nitrogen-containing condensed heterocycles and partial reduction products thereof; and oxygen-containing condensed heterocycles such as 3-hydrobenzofuran 2-one, and partially reduced products thereof.

When R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , and R ^4Z5 and R ^5Z5 form a ring, the ring may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{N1Z5 , R 1Z5 , R 2Z5 , R 3Z5 , R 4Z5 , R 5Z5 , R 6Z5 , R 7Z5 , R 101Z5 and R 102Z5 may have} . Preferred examples of the substituent include the same as preferred substituents which the hydrocarbon group represented by R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , R ^7Z5 , R ^101Z5 and R ^102Z5 may have can

When R ^3Z5 and R ^4Z5 form a ring, it is preferable that R ^2Z5 and R ^5Z5 are each independently a hydrogen atom, an amino group and a hydroxyl group.

When R ^2Z5 and R ^3Z5 form a ring, R ^4Z5 and R ^5Z5 preferably do not form a ring, more preferably R ^4Z5 and R ^5Z5 are hydrogen atoms.

When R ^4Z5 and R ^5Z5 form a ring, R ^2Z5 and R ^3Z5 preferably do not form a ring, more preferably R ^2Z5 and R ^3Z5 are hydrogen atoms. R ^1Z5 , R ^6Z5 and R ^7Z5 are preferably a hydrogen atom.

R ^N1Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -CO ₂ M or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent Preferably, it is more preferably a C1-C30 hydrocarbon group which may have a substituent, It is still more preferable that it is a C1-C20 hydrocarbon group which may have a substituent, It is a C1-C15 hydrocarbon group which may have a substituent It is especially preferable, and it is especially more preferable that it is a C1-C10 hydrocarbon group which may have a substituent, It is especially preferable that it is a C1-C6 hydrocarbon group which may have a substituent, or a C1-C5 hydrocarbon group which may have a substituent. and more preferably a methyl group, an ethyl group, or a phenyl group, and most preferably a methyl group or an ethyl group.

From the viewpoint that the phase difference value of the color filter formed from the coloring composition becomes small, at least one of R ^2Z5 , R ^3Z5 , R ^4Z5 , and R ^5Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -OCO-R ^102Z5 , -COCO-R ^102Z5 , -OR ^102Z5 , -SO ₂ -R ^101Z5 , -SO ₂ N(R ^102Z5 ) ₂ , -CON(R ^102Z5 ) ₂ , -N(R ^102Z5 ) ₂ , -NHCO-R ^102Z5 , -NHCO-N(R ^102Z5 ) ₂ , -NHCOOR ^102Z5 , -OCON(R ^102Z5 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, optionally having 1 to 40 carbon atoms is preferably a hydrocarbon group or a heterocyclic group which may have a substituent, and a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N(R ^102Z5 ) ₂ , a nitro group, or all or part of a hydrogen atom A hydrocarbon group having 1 to 20 carbon atoms substituted with a fluorine atom, -NHCO-R ^102Z5 , -OR ^102Z5 , -SO ₃ M or -CO ₂ M is more preferable, and a nitro group or a C 1 to C 40 substituent which may have a substituent It is more preferably a hydrocarbon group, and still more preferably a nitro group or a tert-butyl group. Alternatively, at least one set of R ^2Z5 and R ^3Z5 , R ^3Z5 and R ^4Z5 , or R ^4Z5 and R ^5Z5 preferably forms a ring.

From the viewpoint that the retardation value of the color filter formed from the coloring composition becomes small, at least one of R ^2Z5 , R ^3Z5 , R ^4Z5 , and R ^5Z5 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, - N(R ^102Z5 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z5 , -OR ^102Z5 , -SO ₃ M or -CO ₂ M preferably,

It is more preferable that it is a C1-C40 hydrocarbon group which may have a nitro group or a substituent, and it is still more preferable that it is a nitro group or a tert- butyl group. Among them, R ^3Z5 is a nitro group or a tert-butyl group and R ^2Z5 , R ^4Z5 and R ^5Z5 are a hydrogen atom, or R ^2Z5 , R ^3Z5 and R ^5Z5 are a hydrogen atom and R ^4Z5 is a nitro group or tert-butyl It is more preferable to be a group.

Specific examples of compound IZ5 include, for example, compound IZ5 having a substituent shown in Table 1Z5, Table 2Z5, Table 3Z5, Table 4Z5, Table 5Z5, Table 6Z5, Table 7Z5 and Table 10Z5 to Table 13Z5 in the formula IZ5-aa. -1 to compound I-IZ5-542 or an alkali metal salt thereof. B ^a1Z5 B ^a2Z5 is a formula (BB2) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1), a formula (BBO8), a formula (BBO10) , any partial structure represented by the formulas (BBD1) and (BBJ2) is shown. Formula (BB2) to Formula (BB60), Formula (BBK2), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), Formula (BBO8), Formula (BBO10), Formula (BBD1) and Formula (BBJ2) is a formula (BB2) to (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1) representing B ^a1Z1 B ^a2Z1 of the formula IZ1-aa , equivalent to formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2). B ^a1Z5 and B ^a2Z5 each represent a bond, and B ^a1Z5 is a formula (BB2) to a formula (BB60), a formula (BBK2), a formula (BBK3), a formula (BBK4), a formula (BBK14), a formula (BBI1) , when it is a bond of B ¹ in formulas (BBO8), (BBO10), (BBD1) and (BBJ2), B ^a2Z5 is a bond of B ² , and B ^a1Z5 is a bond of formulas (BB2) to (BB60) , the binding of B2 in Formula (BBK2), Formula (BBK3), Formula (BBK4), Formula (BBK14), Formula (BBI1), Formula (BBO8), Formula (BBO10), Formula ( ^BBD1 ), and Formula (BBJ2) In the case of a hand, B ^a2Z5 is a binding hand of B ¹ .

As B ^a1Z5 B ^a2Z5 , Formula (BB6), Formula (BB8), Formula (BB11), Formula (BB14), Formula (BB19), Formula (BB37), Formula (BB58), Formula (BBJ2), Formula (BBO8) and formulas (BBO10), more preferably formulas (BB6) and (BB19).

Each symbol in Table 1Z5, Table 2Z5, Table 3Z5, Table 4Z5, Table 5Z5, Table 6Z5, Table 7Z5, and Table 10Z5 to Table 13Z5 shows the following partial structures. In addition, in the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ"" represents a benzyl group, "NPR" represents a propyl group, "IPR" represents an isopropyl group, "IBu" represents an isobutyl group, "EOE" represents -CH ₂ CH ₂ OCH ₂ CH ₃ , "ALL " represents an allyl group, "HYE" represents a 2-hydroxyethyl group, "COM" represents -CO-CH ₃ , "COE" represents -COO-CH ₂ CH ₃ , and "OCM" represents -OCO represents -CH ₃ , "OME" represents -O-CH ₃ , "SOT" represents a tosyl group, "SNH" represents -SO ₂ NH-CH ₂ CH(CH ₂ CH ₃ )((CH ₂ ) ₃ CH ₃ ), "SN2" is -SO ₂ N(CH ₃ ) ((CH ₂ ) ₇ CH ₃ ), "CNM" is -CONHCH ₃ , "CN2" is -CON(CH ₃ ) )C ₆ H ₅ , “NPH” is —NHC ₆ H ₅ , “NOT” is —N((CH ₂ ) ₇ CH ₃ ) ₂ , “NCO” is —NHCO((CH ₂ ) ₄ CH ₃ ), "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO2" represents a nitro group , "SUA" represents -SO ₃ H, "CBA" represents -CO ₂ H, "CHO" represents -CHO, "OCH" represents -OCOH, "OH" represents -OH, "SFM" represents -SO ₂ NH ₂ , "CBM" represents -CONH ₂ , and "NH2" represents -N H ₂ is represented, "NCH" represents -NHCOH, and * represents a bond. In the table, the following partial structures are indicated by symbols.

[Table 1Z5]

[Table 2Z5]

[Table 3Z5]

[Table 4Z5]

[Table 5Z5]

[Table 6Z5]

[Table 7Z5]

[Table 10Z5]

[Table 11Z5]

[Table 12Z5]

[Table 13Z5]

For example, the compound IZ5-1 is a compound represented by the following formula IZ5-1.

Compound IZ5-1 to compound IZ5-160 and compound IZ5-247 to compound IZ5-542 are preferable, and compound IZ5-1 to compound IZ5-160 and compound IZ5-247 to compound IZ5-484 are more preferable, and compound IZ5- 1 to the compound IZ5-160 are still more preferable, the compound IZ5-1 to the compound IZ5-101 are still more preferable, and the compound IZ5-1 to the compound IZ5-44 are particularly preferable.

Specific examples of compound IZ5 include: -SO 3 M or -SO ₃ M or The compound which -CO ₂ M substituted is also mentioned. For example, a compound in which 1 to 3 sulfo groups are bonded to compound IZ5-1 of Table 1Z5 is represented by the following structure. In the formula, -(SO ₃ H) means that the hydrogen atom in any of the compounds IZ5-1 of Table 1Z5 is substituted.

Compound IZ5-1 to compound IZ5-160 and compound IZ5-247 to compound IZ5-542 are preferably compounds in which 1 to 3 -SO ₃ M or -CO ₂ M are bonded;

A compound in which 1 to 3 -SO ₃ M or -CO ₂ M is bonded to compound IZ5-1 to compound IZ5-160 and compound IZ5-247 to compound IZ5-484 is more preferable;

A compound in which one to three -SO ₃ M or -CO ₂ M is bonded to compound IZ5-1 to compound IZ5-160 is more preferable, and to compound IZ5-1 to compound IZ5-101, one to three -SO A compound in which ₃ M or -CO ₂ M is bonded is even more preferable, and a compound in which 1 to 3 -SO ₃ M or -CO ₂ M is bonded to compound IZ5-1 to compound IZ5-44 is particularly preferable.

As the compound (IZ5), in the formula (IZ5), R ^N1Z5 is -CO-R ^102Z5 , -COO-R ^101Z5 , -CON(R ^102Z5 ) ₂ , or -SO ₃ M and -CO ₂ M the group consisting of _A ^hydrocarbon group having ₁ to 20 carbon atoms which may have a substituent selected from a group, -SO ₃ M or -CO ₂ M, and R ^2Z5 to R ^5Z5 are each, independently, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102Z5 ) ₂ , a nitro group; a hydrocarbon group having 1 to 20 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z5 , -OR ^102Z5 , -SO ₃ M or -CO ₂ M, and at least one of R ^2Z5 to R ^5Z5 is, A hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102Z5 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z5 , -OR ^102Z5 , -SO ₃ M or -CO ₂ M,

R ^6Z5 and R ^7Z5 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, -SO ₃ M or -CO ₂ is M,

R ^102Z5 is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, and R ^101Z5 is -SO ₃ M and -CO ₂ M A hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of, M is preferably a hydrogen atom or an alkali metal atom, R ^N1Z5 is -CO-R ^102Z5 , -CON (R ^102Z5 ) ₂ or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, R ^1Z5 is a hydrogen atom, R ^2Z5 to R ^5Z5 are each, Independently, a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102Z5 ) ₂ , a nitro group, a hydrocarbon group having 1 to 10 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, -NHCO- R ^102Z5 , -OR ^102Z5 , -SO ₃ M or -CO ₂ M , and at least one of R ^2Z5 to R ^5Z5 is a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102Z5 ) ₂ , a nitro group, A hydrocarbon group having 1 to 10 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102Z5 , -OR ^102Z5 , -SO ₃ M or -CO ₂ M, R ^6Z5 and R ^7Z5 are the same group , a hydrogen atom, or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M, R ^102Z5 is a hydrogen atom, or -SO ₃ M and -CO ₂ It is a hydrocarbon group of 1 to 10 carbon atoms which may have a substituent selected from the group consisting of M, and R ^101Z5 is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M and -CO ₂ M It is a hydrocarbon group, and M is a hydrogen atom or an alkali metal atom. All preferred, R ^N1Z5 is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -CO-R ^102Z5 , -CON(R ^102Z5 ) ₂ , or -SO ₃ M or -CO ₂ M is,

R ^1Z5 is a hydrogen atom, R ^2Z5 to R ^5Z5 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, —N(R ^102Z5 ) ₂ , a nitro group, a trifluoromethyl group, -OR ^102Z5 , -SO ₃ M or -CO ₂ M, and at least one of R ^2Z5 to R ^5Z5 is a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102Z5 ) ₂ , a nitro group, trifluoro A methyl group, -OR ^102Z5 , -SO ₃ M or -CO ₂ M,

R ^6Z5 and R ^7Z5 are the same group and represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms;

R ^102Z5 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ M or -CO ₂ M, R ^101Z5 is -SO ₃ M and -CO ₂ M A hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of

M is more preferably a hydrogen atom or an alkali metal atom.

Compound IZ5, when R ^1Z5 is a hydrogen atom, reacts a compound represented by the formula pt1Z5 (hereinafter sometimes referred to as a phthalonitrile compound) with a compound represented by the formula pt2Z5 (hereinafter sometimes referred to as an alkoxide compound) After the reaction, it can be prepared by further reacting the compound represented by the formula pt3Z5 with the compound represented by the formula pt4Z5 in the presence of an acid. Further, when R ^1Z5 is other than a hydrogen atom, compound IZ5 can be produced by further reacting with a compound represented by the formula pt5Z5.

[In formula pt1Z5, formula pt2Z5, formula pt3Z5, formula pt4Z5, formula pt5Z5 and formula IZ5, R ^N1Z5 , R ^1Z5 , R ^2Z5 , R ^3Z5 , R ^4Z5 , R ^5Z5 , R ^6Z5 , and R ^7Z5 have the same meaning as above indicates R ^14Z5 represents an alkyl group having 1 to 20 carbon atoms. M ^1Z5 represents an alkali metal atom. LG represents a halogen atom, a methanesulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group.]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ^14Z5 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group, and preferably a C1 group. -6 alkyl groups are mentioned.

Examples of the alkali metal atom represented by M ^1Z5 include a lithium atom, a sodium atom and a potassium atom.

The usage-amount of an alkoxide compound is 0.1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 0.2-5 mol, More preferably, it is 0.3-3 mol, More preferably, it is 0.4-2 mol. it's a mall

The usage-amount of compound pt3Z5 is 1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 1-5 mol, More preferably, it is 1-3 mol, More preferably, it is 1-2 mol. am.

The usage-amount of compound pt4Z5 is 1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 1-5 mol, More preferably, it is 1-3 mol, More preferably, it is 1-2 mol. am.

Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; and carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid These are mentioned, More preferably, acetic acid is mentioned.

The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, still more preferably 1 to 6 moles with respect to 1 mole of the phthalonitrile compound.

The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z5, and the compound pt4Z5 is usually carried out in the presence of a solvent.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N ,N-dimethylformaldehyde, N-methylpyrrolidone and dimethyl sulfoxide, and more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1- octanol, acetone, methylene chloride, chloroform, N,N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide are exemplified, particularly preferably water, acetonitrile, methanol, ethanol and 2-propanol. can be heard

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of phthalonitrile compounds.

Reaction temperature is 0-200 degreeC normally, Preferably it is 0-100 degreeC, More preferably, it is 0-70 degreeC, More preferably, it is 0-50 degreeC. The reaction time is usually 0.5 to 300 hours.

The amount of compound pt5Z5 to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, further preferably 1 mole of compound IZ5 in which R ^1Z5 is a hydrogen atom. 1 to 2 moles.

When the compound pt5Z5 is reacted, it is preferable that a base coexist. Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; organometallic compounds such as butyllithium, tert-butyllithium and phenyllithium; Inorganic bases, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, are mentioned.

The amount of the base used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 3 moles, with respect to 1 mole of compound IZ5 in which R ^1Z5 is a hydrogen atom. 2 moles.

The reaction of the compound pt5Z5 is usually carried out in the presence of a solvent. A solvent can be selected from the range similar to the above.

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of compound ^IZ5 whose R<1>Z5 is a hydrogen atom. The reaction temperature of the compound pt5Z5 is usually -90 to 200°C, preferably -80 to 100°C, more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

When compound IZ5 does not have a sulfo group or -SO ₃ M ² , a sulfo group or -SO ₃ M ²² can be introduced by reacting compound IZ5 with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid. M ²² represents an alkali metal atom. Examples of the alkali metal atom represented by M ²² include a lithium atom, a sodium atom and a potassium atom.

The amount of SO ₃ used in the fuming sulfuric acid is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, still more preferably 5 to 25 moles, with respect to 1 mole of compound IZ5. am. The amount of sulfuric acid used in the fuming sulfuric acid is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, still more preferably 10 to 50 moles with respect to 1 mole of compound IZ5. . The usage-amount of chlorosulfonic acid is 1-500 mol normally with respect to 1 mol of compound IZ5, Preferably it is 10-300 mol, More preferably, it is 10-200 mol, More preferably, it is 10-150 mol.

The reaction temperature for sulfonation is usually -20 to 200°C, preferably -10 to 100°C, and more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

The method for taking out compound IZ5 from the reaction mixture is not particularly limited, and can be taken out by various known methods. For example, after completion of the reaction, the compound IZ5 can be extracted by filtering the reaction mixture. After filtration, the obtained residue may be subjected to column chromatography, recrystallization, or the like. After completion of the reaction, the solvent of the reaction mixture may be distilled off, and then purified by column chromatography.

<Compound IZ6>

Compound IZ6 is represented by formula IZ6.

[In formula IZ6, D represents a structure having an isoindoline skeleton. Z represents -SO ₃ ^- or -CO ₂ ^- . A ^c+ represents a c-valent metal cation. a represents the integer of 1-10. b represents an integer of 1 or more. c represents the integer of 2-10. d represents an integer of 1 or more.

When two or more D, Z, a, or A ^c+ exist, they may be same or different, respectively. Formulas I'Z6 and I"Z6 each represent a partial structure of Formula IZ6, and D, Z, A ^c+ , a, b, c and d represent the same thing as in Formula IZ6, provided that The absolute value of the negative valence of the partial structure represented by I'Z6 and the positive valence of the partial structure represented by the formula I"Z6 are the same.]

The integer represented by a is 1-10, Preferably it is 1-8, More preferably, it is 1-6, More preferably, it is 1-4. The integer represented by b is 1 or more, Preferably it is 1-10, More preferably, it is 1-8. The integer represented by c is 2-10, Preferably it is 2-8, More preferably, it is 2-6, More preferably, it is 2-4. The integer represented by d is 1 or more, Preferably it is 1-10, More preferably, it is 1-8. Z is preferably -CO ₂ ^- .

A ^c+ represents a divalent or higher metal cation. As a divalent or higher metal cation,

and cations of metals of Groups 2 to 15 of the periodic table of elements, preferably Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Cd ²⁺ , Ni ²⁺ , Zn ²⁺ , Cu divalent metal cations such as ²⁺ , Hg ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Pb ²⁺ and Mn ²⁺ ; trivalent metal cations such as Al ³⁺ , Fe ³⁺ and Cr ³⁺ ; and tetravalent metal cations such as Sn ⁴⁺ and Mn ⁴⁺ , more preferably Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ and Mn ⁴⁺ , and more preferably Mg ²⁺ , Ca ^{2 +} , Sr ²⁺ , Ba ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ and Mn ⁴⁺ .

The compound represented by the formula IZ6 is preferably a compound represented by the formula IZ6-A (hereinafter, sometimes referred to as compound IZ6-A).

[In formula IZ6-A, A ^c+ , b, c and d have the same meanings as above.

R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 are, independently of each other, a hydrogen atom, -CO-R ^102AZ6 , -COO-R ^101AZ6 , -OCO- R ^102AZ6 , -COCO-R ^102AZ6 , -OR ^102AZ6 , -SO ₂ -R ^101AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ , -N(R ^102AZ6 ) ₂ , -NHCO-R ^102AZ6 , -NHCO-N(R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , -OCON(R ^102AZ6 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, -SO ₃ ^- , -CO ₂ ^- represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^2AZ6 and R ^3AZ6 , R ^3AZ6 and R ^4AZ6 , R ^4AZ6 and R ^5AZ6 , R ^AA1Z6 and R ^AA2Z6 , and R ^12AZ6 and R ^13AZ6 may be respectively bonded to each other to form a ring. R ^101AZ6 represents, independently of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102AZ6 represents, each independently, a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom.

Formula IZ6-A' and formula IZ6-A" each represent a partial structure of formula IZ6-A, A ^c+ , b, c, d, R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 represent the same thing as in formula IZ6-A.

When a ^plurality of R 1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 , R ^102AZ6 , M, c or A ^c+ exists, each of them may be the same , may be different.

R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 is at least one of (ra-i) to (ra-iii) The total number of -SO ₃ ^- or -CO ₂ ^- in R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 is a.

(ra-i) At least one of R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 is -SO ₃ ^- or -CO ₂ ^- .

(ra-ii) at least one of R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 is -CO-R ^102AZ6 , -COO-R ^101AZ6 , -OCO -R ^102AZ6 , -COCO-R ^102AZ6 , -OR ^102AZ6 , -SO ₂ -R ^101AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ , -N(R ^102AZ6 ) ₂ ,-NHCO- R ^102AZ6 , -NHCO-N(R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , or -OCON(R ^102AZ6 ) ₂ , and R ^101AZ6 and R ^102AZ6 are -SO ₃ ^- or -CO ₂ ^- having 1 to 40 carbon atoms. of a hydrocarbon group or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(ra-iii) at least one of R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 has -SO ₃ ^- or -CO ₂ ^- having 1 to It is a hydrocarbon group of 40 or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group and the said heterocyclic group may have a substituent other than -SO ₃ ^- or -CO ₂ ^- .

a has the same meaning as in Formula IZ6. When a plurality of as exist, they may be the same or different.

The absolute value of the negative valence of the partial structure represented by the formula IZ6-A' and the positive valence of the partial structure represented by the formula IZ6-A" are the same. The broken line indicates the E or Z body.]

The hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 has 1 to 40 carbon atoms, preferably 1 to 30, More preferably, it is 1-20, More preferably, it is 1-15, Especially preferably, it is 1-10.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 include a methyl group, an ethyl group, a propyl group, straight-chain alkyl groups such as butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, heptadecyl group, octadecyl group and icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl)pentyl group, (2- methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group and (3-ethyl) heptyl group branched chain alkyl groups and the like; Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-pro alkenyl groups such as phenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl; and the like. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15. Especially, it is especially preferable that it is a C1-C10, More preferably, it is a C1-C8, Even more preferably, it is a C1-C5 linear or branched alkyl group.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 include a cyclopropyl group, 1-methyl Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl 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 Sil 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, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and 3,3,5,5-tetramethylcyclohexyl group, 4 - cycloalkyl groups such as a pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; cycloalkenyl groups such as a cyclohexenyl group (eg, cyclohexa-2-ene, cyclohexa-3-ene), a cycloheptenyl group, and a cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane, etc. are mentioned. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 4 to 20 carbon atoms, still more preferably 4 to 15 carbon atoms, and particularly More preferably, it is 5-15, Most preferably, it is 5-10. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

Examples of the aromatic hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 include a phenyl group, an o-tolyl group, and a m-tolyl group. , p-tolyl 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, 4- Biphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 4-ethylphenyl group, 4-Butylphenyl group, 4-pentylphenyl group, 2,6-bis(2-propyl)phenyl group, 4-cyclohexylphenyl group, 2,4,6-trimethylphenyl group, 4-octylphenyl group, 4-vinylphenyl group, 1-naph Tyl group, 2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group, phenanthryl group and anthryl group , aromatic hydrocarbon groups such as a pyrenyl group; and the like. Carbon number of an aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-15.

The hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 is the above-mentioned hydrocarbon group (for example, an aromatic hydrocarbon group, A group obtained by combining at least one of a chain hydrocarbon group and an alicyclic hydrocarbon group) may be used, and an aralkyl group such as a benzyl group, a phenethyl group and a 1-methyl-1-phenylethyl group; arylalkenyl groups such as a phenylethenyl group (phenylvinyl group); Aryl alkynyl groups, such as a phenylethynyl group; a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; A cyclohexylmethylphenyl group, a benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. are mentioned.

R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 The group represented by the above hydrocarbon group (for example, a chain hydrocarbon group and an alicyclic As a group combining formula hydrocarbon group), for example, cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, 2-methylcyclohexylmethyl group, cyclo The alkyl group to which one or more alicyclic hydrocarbon groups, such as a hexylethyl group and an adamantylmethyl group, couple|bonded may be sufficient.

These carbon number becomes like this. Preferably it is 4-30, More preferably, it is 6-30, More preferably, it is 6-20, More preferably, it is 4-20, More preferably, it is 4-15, Especially preferably, it is 6-15.

The hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have a substituent. The substituent may be monovalent or divalent. The divalent substituent preferably has two bonds bonded to the same carbon atom to form a double bond.

Examples of the monovalent substituent include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, (2-ethyl ) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1 -Methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6 -Dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyloxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyano group Phenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyloxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group Group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-ethoxyphenyloxy group, 2-ethoxyphenyloxy group, 3-ethoxyphenyloxy group, etc., and groups represented by the following formulas A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an oxy group in which an alkylsulfamoyl group (preferably a group derivatized with an octylsulfamoyl group) or the like) is bonded to one side;

Methylthio group, ethylthio group, propylthio group, butylthio group, tert-butylthio group, pentylthio group, hexylthio group, (2-ethyl)hexylthio group, heptylthio group, octylthio group, nonylthio group , a sulfanyl group to which a hydrocarbon group having 1 to 20 (preferably 1 to 10) carbon atoms such as decylthio group, undecylthio group, dodecylthio group, icosylthio group, phenylthio group and o-tolylthio group is bonded;

an epoxy group, an oxetanyl group, a tetrahydrofuryl group, a tetrahydropyranyl group;

formyl group;

Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the following formulas, such as a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivatized group thereof (for example, a carboxy group , a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) When it is set as a canoyl group, carbon number becomes like this. Preferably it is 2-12);

Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group , decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, icosyloxycarbonyl group, phenyloxycarbonyl group, o-tolyloxycarbonyl group, etc. to 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) ), a group derivatized with an oxycarbonyl group to which) is bonded;

amino group; N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diiso group Propylamino group, N-butylamino group, N,N-dibutylamino group, N-isobutylamino group, N,N-diisobutylamino group, N-sec-butylamino group, N,N-disec-butylamino group, N- tert-butylamino group, N,N-ditert-butylamino group, N-pentylamino group, N,N-dipentylamino group, N-(1-ethylpropyl)amino group, N,N-di(1-ethylpropyl)amino group , N-hexylamino group, N,N-dihexylamino group, N-(2-ethyl)hexylamino group, N,N-di(2-ethyl)hexylamino group, N-heptylamino group, N,N-diheptylamino group, N-octylamino group, N,N-dioctylamino group, N-nonylamino group, N,N-dinonylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N -Propylmethylamino group, N,N-isopropylmethylamino group, N,N-butylmethylamino group, N-decylamino group, N,N-decylmethylamino group, N-undecylamino group, N,N-undecylmethylamino group, N-dodecylamino group, N,N-dodecylmethylamino group, N-icosylamino group, N,N-icosylmethylamino group, N,N-tert-butylmethylamino group, N,N-phenylmethylamino group, and the like; One or two hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), such as a group represented by the following formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a preferably a chlorine atom), an amino group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

sulfamoyl group; N-methylsulfamoyl group, N,N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N,N-diethylsulfamoyl group, N-propylsulfamoyl group, N,N-dipropylsulfamoyl group, N-isopropylsulfamoyl group, N,N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N,N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N,N-diiso Butylsulfamoyl group, N-sec-butylsulfamoyl group, N,N-disec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N-pentyl group sulfamoyl group, N,N-dipentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N,N-di(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N, N-dihexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N,N-diheptylsulfamo Diyl, N-octylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-octylmethylsulfamoyl group, N-nonylsulfamoyl group, N,N-dinonylsulfamoyl group, N-phenylsulfa Moyl group, N,N-diphenylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-butylmethyl Sulfamoyl group, N-decylsulfamoyl group, N,N-decylmethylsulfamoyl group, N-undecylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N-dodecylsulfamoyl group, N, N-dodecylmethylsulfamoyl group, N-icosylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, etc. , and a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a sulfamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a group derivatized with an octylsulfamoyl group) or the like;

formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms), such as amino groups, decanoylamino groups, undecanoylamino groups, dodecanoylamino groups, henicosanoylamino groups and benzoylamino groups, and groups represented by the following formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. a carbonylamino group to which the group) is bonded (when the carbonylamino group is an alkanoylamino group, the carbon number is preferably 1 to 12);

hydroxyl group; Halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;

carboxyl group; —CO ₂ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); a sulfo group, —SO ₃ M ² (M ² is an alkali metal, preferably lithium, sodium, potassium); nitro group; cyano group;

formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, and the like, and groups having 1 to 20 carbon atoms (preferably 1 to carbon atoms) 10) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) a carbonyloxy group (when the carbonyloxy group is an alkanoyloxy group, the carbon number is preferably 1 to 10) to which a group derivatized with, etc.) is bonded;

Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl)hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, unde A hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) such as a silsulfonyl group, a dodecylsulfonyl group, an icosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, and a group represented by the following formula or a derivatized group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. ) is a sulfonyl group bonded;

carbamoyl group; N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N,N-diethylcarbamoyl group, N-propylcarbamoyl group, N,N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N,N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N,N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N,N-diiso Butylcarbamoyl group, N-sec-butylcarbamoyl group, N,N-disec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N-pentyl group Carbamoyl group, N,N-dipentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N, N-dihexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N,N-diheptylcarbamo group Diyl, N-octylcarbamoyl group, N,N-dioctylcarbamoyl group, N-nonylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-octylbutylcarbamoyl group, N,N- dinonylcarbamoyl group, N-phenylcarbamoyl group, N,N-diphenylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-isopropylmethyl Carbamoyl group, N,N-butylmethylcarbamoyl group, N-decylcarbamoyl group, N,N-decylmethylcarbamoyl group, N-undecylcarbamoyl group, N,N-undecylmethylcarbamoyl group, N-dodecylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N-icosylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, One or two C1-C20 (preferably C1-C10) hydrocarbon groups, such as N,N-phenylmethylcarbamoyl group, and the group represented by the following formula, or its derivatized group (for example, a carboxy group , a carbamoyl group substituted with a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group);

Trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluoro All hydrogen atoms such as octyl group, perfluorononyl group, perfluorodecyl group, perfluorodecyl group, perfluorododecyl group, perfluoroicosyl group, perfluorocyclohexyl group and perfluorophenyl group a hydrocarbon group having 1 to 20 carbon atoms substituted with a fluorine atom;

Perfluoroethylmethyl group, perfluoropropylmethyl group, perfluoroisopropylmethyl group, perfluorobutylmethyl group, perfluoropentylmethyl group, perfluorohexylmethyl group, perfluoroheptylmethyl group, perfluorooctylmethyl group, purple A linear or branched chain having 1 to 20 carbon atoms in which all hydrogen atoms, such as a luoronylmethyl group, perfluorodecylmethyl group, perfluorodecylmethyl group, perfluorododecylmethyl group, and perfluoroicosylmethyl group, are substituted with fluorine atoms a hydrocarbon group having 1 to 20 carbon atoms substituted with an alkyl group of;

Some of the hydrogen atoms such as 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group and 2,4,6-trifluorophenyl group are substituted with fluorine having 1 to 20 carbon atoms (preferably from 1 to 20 carbon atoms) The hydrocarbon group of 10);

-CO-SH, -CO-S-CH ₃ , -CO-S-CH ₂ CH ₃ , -CO-S-CH ₂ -CH ₂ -CH ₃ and -CO-S-CH ₂ -CH ₂ -CH ₂ A C1-C20 (preferably C1-C10) alkylthiocarbonyl group, such as -CH3, _A C6-C20 arylthiocarbonyl group, such as -CO _{- SC6H5} ;

*-COCO-R represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those satisfying 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group (for example, a group derivatized with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) ) of the group;

*-NRCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, those satisfying 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OCONR ₂ represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivative thereof a group (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.); The R groups may be the same as or different from each other, and may be bonded to each other to form a ring);

*-NRCOOR represented by the following formula (wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (For example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-OP(O)(OR) ₂ such as *-OP(O)(OCH ₃ ) ₂ (wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms (for example, the hydrocarbon group mentioned above) Those satisfying heavy carbon atoms of 1 to 20), or a derivatized group thereof (eg, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably a chlorine atom) is a group derivatized with an octylsulfamoyl group), etc.), and the R may be the same as or different from each other, and may be bonded to each other to form a ring);

*-SiR ₃ (such as *-Si(CH ₃ ) ₃ , *-Si(CH ₂ CH ₃ ) ₃ , *-Si(C ₆ H ₅ ) ₃ and *-Si(CH(CH ₃ ) ₂ ) ₃ , etc. In the formula, R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups mentioned above), or a derivatized group thereof (for example, a carboxy group or a sulfo group) , a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) group, or may be bonded to each other to form a ring); -SO ₃ ^- ; -CO ₂ ^- ; and the like.

Examples of the divalent substituent include an imino group substituted by an oxo group, a thioxo group, an imino group, an imino group substituted by an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted by an aryl group having 6 to 20 carbon atoms. can Examples of the imino group substituted by the alkyl group include CH ₃ -N=, CH ₃ -CH ₂ -N=, CH ₃ -(CH ₂ ) ₂ -N=, and CH ₃ -(CH ₂ ) ₃ -N=. there is. Examples of the imino group substituted by the aryl group include C ₆ H ₅ -N=.

As a substituent of a C1-C40 hydrocarbon group, Preferably, the substituent of group s1 is mentioned. The derivatized group shown below is preferably a group derivatized with a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) or the like. Do.

[group s1]

an oxy group in which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; halogen atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.);

-SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a C1-C20 hydrocarbon group substituted with a C1-C20 linear or branched alkyl group in which all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo group; -SO ₃ ^- ; -CO ₂ ^- .

As a substituent of a C1-C40 hydrocarbon group, More preferably, the substituent of group s2 is mentioned.

[group s2]

an oxy group in which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded to one side;

a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

amino group; an amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms;

sulfamoyl group; a sulfamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded; hydroxyl group; a fluorine atom, a chlorine atom, a bromine atom; -CO ₂ M (preferably a carboxy group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.);

-SO ₃ M (preferably a sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom.); nitro group; cyano group;

a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded;

a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivatized group thereof is bonded;

carbamoyl group; a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof; a hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms;

a hydrocarbon group having 1 to 10 carbon atoms in which all of the hydrogen atoms are substituted with a fluorine atom; a hydrocarbon group having 1 to 10 carbon atoms in which a part of hydrogen atoms are substituted with fluorine; oxo group; -SO ₃ ^- ; -CO ₂ ^- .

As the hydrocarbon group having 1 to 40 carbon atoms having a substituent represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 , monovalent or 2 and hydrocarbon groups having 1 to 40 carbon atoms having a valent substituent; Preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms having a monovalent or divalent substituent, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms having a monovalent or divalent substituent, monovalent or 2 an aromatic hydrocarbon group having 6 to 30 carbon atoms having a valent substituent or a group in which hydrocarbon groups are combined, and a group having 4 to 30 carbon atoms having a monovalent or divalent substituent is exemplified;

More preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, and a carbon number having a substituent in group s1 a group having 6 to 20 aromatic hydrocarbon groups or a combination of hydrocarbon groups, and groups having a substituent of group s1 having 4 to 20 carbon atoms;

Particularly preferably, a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, a carbon number having a substituent of group s2 It is a group in which the aromatic hydrocarbon group of 6-15 or a hydrocarbon group was combined, and the group of C4-15 which has a substituent of group s2 is mentioned.

The heterocyclic group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may be monocyclic or polycyclic, preferably a ring structure. It is a heterocyclic ring containing a hetero atom as an element. As a hetero atom, a nitrogen atom, an oxygen atom, a sulfur atom, etc. are mentioned.

The heterocyclic group preferably has 3 to 30 carbon atoms, more preferably 3 to 22 carbon atoms, still more preferably 3 to 20 carbon atoms, still more preferably 3 to 18 carbon atoms, still more preferably 3 to 15 carbon atoms. and particularly preferably 3 to 14.

Examples of the heterocycle containing a nitrogen atom include saturated monocyclic heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrroles such as 2,5-dimethylpyrrole, pyrazoles such as 2-methylpyrazole and 3-methylpyrazole, and 5-membered rings such as imidazole, 1,2,3-triazole and 1,2,4-triazole systemic unsaturated heterocycle; pyrimidines such as pyridine, pyridazine and 6-methylpyrimidine; 6-membered ring unsaturated heterocycles such as pyrazine and 1,3,5-triazine; Quinox such as indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro(3-methyl)quinoxaline, 3-methylquinoxaline condensed bicyclic heterocycles such as saline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole, and benzopiperizine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and the like.

Examples of the heterocycle containing an oxygen atom include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane. ; bicyclic saturated heterocycles such as 1,4-dioxaspiro[4.5]decane and 1,4-dioxaspiro[4.5]nonane; lactone-based heterocycles such as α-acetolactone, β-propiolactone, γ-butyrolactone, γ-valerolactone and δ-valerolactone; 5-membered ring unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran;

Condensed bicyclic heterocycles, such as benzopyran, such as 1-benzofuran and 4-methylbenzopyran, benzodioxole, chroman, and isochroman; Condensed tricyclic heterocycles, such as xanthene and dibenzofuran; and the like.

As a heterocyclic ring containing a sulfur atom, 5-membered ring type saturated heterocycles, such as dithiolane; 6-membered ring type saturated heterocycles, such as thiane, 1, 3- dithiane, and 2-methyl 1, 3- dithiane; 5-membered ring unsaturated heterocycles, such as thiophene, such as 3-methylthiophene and 2-carboxythiophene, benzothiopyran, such as 4H-thiopyran and benzotetrahydrothiopyran; Condensed bicyclic heterocycles, such as benzothiophene; condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.

Examples of the heterocycle containing a nitrogen atom and an oxygen atom include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone. Summons; Monocyclic unsaturated heterocyclic rings, such as isoxazole, such as oxazole, such as 4-methyloxazole, 2-methylisoxazole, and 3-methylisoxazole;

Condensed bicyclic heterocyclic rings, such as benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, and benzoimidazoline; Condensed bicyclic heterocycles, such as phenoxazine; condensed tricyclic heterocycles such as phenoxazine; and the like.

Examples of the heterocycle containing a nitrogen atom and a sulfur atom include monocyclic heterocycles such as 3-methylthiazole and 2,4-dimethylthiazole; Condensed bicyclic heterocycles, such as benzothiazole; condensed tricyclic heterocycles such as phenothiazine; and the like.

The heterocyclic ring may be a group in which the above-mentioned hydrocarbon groups are combined, and examples thereof include a tetrahydrofurylmethyl group and the like.

The heterocycle may be represented by the following formula.

The heterocyclic group may be a heterocyclic group formed by bonding two or more of R ^1AZ6 to R ^5AZ6 . Such a heterocyclic group has a ring structure of two or more rings together with the benzene ring to which R ^1AZ6 to R ^5AZ6 are bonded. As a ring structure of this two or more rings, the structure of the following formula is mentioned, for example.

The bonding position of the heterocyclic ring is a portion from which any hydrogen atom contained in each ring is removed.

The heterocyclic group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Moreover, when the said heterocyclic ring contains the nitrogen atom as its structural element, the hydrocarbon group mentioned above may couple|bond with this nitrogen atom as a substituent.

Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

As the heterocyclic group having a substituent represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 , a heterocyclic group having a monovalent or divalent substituent A ring is mentioned, Preferably, the heterocyclic group which has a substituent of group s1 is mentioned, More preferably, the heterocyclic group which has a substituent of group s2 is mentioned.

The number of substituents (1st substituent) which the said hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may mutually independently be the same or different. In addition, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

Hereinafter, -CO-R ^102AZ6 , -COO-R ^101AZ6 , -OCO-R ^102AZ6 , -COCO- of R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 R ^102AZ6 , -OR ^102AZ6 , -SO ₂ -R ^101AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ , -N(R ^102AZ6 ) ₂ , -NHCO-R ^102AZ6 , -NHCO-N (R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , -OCON(R ^102AZ6 ) ₂ , a halogen atom, -SO ₃ M, and -CO ₂ M are described. -CO-R ^102AZ6 , -COO-R ^101AZ6 , -OCO-R ^102AZ6 , -COCO-R ^102AZ6 , -OR ^102AZ6 , -SO ₂ -R ^101AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , - CON(R ^102AZ6 ) ₂ , -N(R ^102AZ6 ) ₂ , -NHCO-R ^102AZ6 , -NHCO-N(R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , -OCON(R ^102AZ6 ) ₂ , R ^101AZ6 , R ^102AZ6 It is preferable that the substituent of group s2, in particular -SO ₃ ^- , -CO ₂ ^- , etc. is bonded to the corresponding moiety.

-CO-R ^{102AZ6 is} a formyl group; Acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl)hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group , dodecanoyl group, henicosanoyl group, benzoyl group, etc., and a group represented by the above formulas, such as a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxyl group, alcohol A carbonyl group (a group derivatized with an agar, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) case, the group having 2 to 41 carbon atoms), and a group corresponding to -CO-R ^102AZ6 in the compounds shown in Tables 1Z6 to 4Z6, preferably having 1 to 11 carbon atoms (more preferably 1 carbon atoms). -CO-R 102AZ6 in the compounds shown in the hydrocarbon group of -10) or the carbonyl group to which the derivatized group is bonded (when the carbonyl group is an alkanoyl group, the carbon number is more preferably 2 to 12) and Tables 1Z6 to ^4Z6 and groups corresponding to .

-COO-R ^101AZ6 includes a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, Octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group, icosyloxycarbonyl group, etc. 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) and a group corresponding to -COO-R ^102AZ6 in the compounds shown in the oxycarbonyl group and the compounds shown in Tables 1Z6 to 4Z6) to which a group derivatized with a and the group corresponding to -COO-R ^102AZ6 in the compound shown in the oxycarbonyl group to which the derivatization group couple|bonded, and Tables 1Z6 - Table 4Z6, etc. are mentioned.

-OCO-R ^102AZ6 is a formyloxy group; Acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoyloxy group, octanoyloxy group, no Nanoyloxy group, decanoyloxy group, undecanoyloxy group, dodecanoyloxy group, henicosanoyloxy group, benzoyloxy group, etc., and groups represented by the above formulas having 1 to 40 carbon atoms (preferably from 1 to carbon atoms). 20) of a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) In the compounds shown in Tables 1Z6 to 4Z6, -OCO-R ^102AZ6 corresponds to a carbonyloxy group to which a carbonyloxy group (a group derivatized with, etc.) is bonded (when the carbonyloxy group is an acyloxy group, it has 2 to 41 carbon atoms) and a carbonyloxy group to which a hydrocarbon group having preferably 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivatized group thereof is bonded (when the carbonyloxy group is an acyloxy group, carbon number is more preferably 2 to 12) and the group corresponding to -OCO-R ^102AZ6 in the compounds shown in Tables 1Z6 to 4Z6, and the like.

As -COCO-R ^102Z6 , methyloxalyl group, ethyloxalyl group, propyloxalyl group, butyloxalyl group, pentyloxalyl group, hexyloxalyl group, (2-ethyl)hexyloxalyl group, heptyloxalyl group group, octyloxalyl group, nonyloxalyl group, decyloxalyl group, undecyloxalyl group, dodecyloxalyl group, icosyloxalyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p - a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as a tolyloxalyl group, and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, and an oxalyl group to which a halogen (preferably a chlorine atom) or a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded.

-OR ^{102AZ6 is} a hydroxyl group; Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group Group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl)hexyloxy group, icosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2 ,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 3,5-dimethylphenyl group Oxy group, 2,2-dicyanophenyloxy group, 2,3-dicyanophenyloxy group, 2,4-dicyanophenyloxy group, 2,5-dicyanophenyloxy group, 2,6-dicyanophenyl Oxy group, 3,4-dicyanophenyloxy group, 3,5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-e A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof, such as a oxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, and a group represented by the above formula A group (for example, a group derivatized with a carboxy group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) In the oxy group and the compounds shown in Tables 1Z6 to 4Z6, a group corresponding to -OR ^102AZ6 is mentioned, and preferably an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded, and Tables 1Z6 to 4Z6 In the compound shown, the group corresponding to -OR ^102AZ6 , etc. are mentioned.

-SO ₂ -R ^{101AZ6 is} a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl)hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, and a nonyl group. sulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, and groups having 1 to 40 carbon atoms (preferably carbon atoms) 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) sulfonyl group) to which a group derivatized with a diyl)) is bonded, and in the compounds shown in Tables 1Z6 to 4Z6, a group corresponding to -SO ₂ -R ^101AZ6 , etc., preferably a hydrocarbon group having 1 to 10 carbon atoms, or The group corresponding to -SO ₂ -R ^101AZ6 in the compound shown in the sulfonyl group to which the derivatization group couple|bonded, and Tables 1Z6 - Table 4Z6, etc. are mentioned.

As -SO ₂ N(R ^102AZ6 ) ₂ , a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfa Moyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-(1-ethylpropyl)sulfamoyl group, N-hexylsulfamoyl group, N-(2-ethyl)hexylsulfamoyl group, N-heptylsulfamoyl group, N-octylsulfamoyl group, N-nonylsulfamoyl group, N-decylsulfamoyl group, N-undecylsulfamoyl group, N-dodecylsulfamoyl group, N-icosylsulfamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A sulfamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z6 to 4Z6 In the compound represented by -SO ₂ NH(R ^102AZ6X ) (R ^102AZ6X is the same as R ^102AZ6 except that it does not form a hydrogen atom), etc.; N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-dipropylsulfamoyl group, N ,N-isopropylmethylsulfamoyl group, N,N-diisopropylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-diisobutylsulfamoyl group, N,N-disec -Butylsulfamoyl group, N,N-ditert-butylsulfamoyl group, N,N-butylmethylsulfamoyl group, N,N-dibutylsulfamoyl group, N,N-dipentylsulfamoyl group, N, N-di(1-ethylpropyl)sulfamoyl group, N,N-dihexylsulfamoyl group, N,N-di(2-ethyl)hexylsulfamoyl group, N,N-diheptylsulfamoyl group, N, N-octylmethylsulfamoyl group, N,N-dioctylsulfamoyl group, N,N-dinonylsulfamoyl group, N,N-decylmethylsulfamoyl group, N,N-undecylmethylsulfamoyl group, N ,N-dodecylmethylsulfamoyl group, N,N-icosylmethylsulfamoyl group, N,N-phenylmethylsulfamoyl group, N,N-diphenylsulfamoyl group, etc., and groups represented by the above formulas, etc. of two C1 to C40 (preferably C1 to C20) hydrocarbon groups or derivatized groups thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), 1 to 10 carbon atoms) A sulfamoyl group substituted with an alkylsulfamoyl group of (preferably a group derivatized with an octylsulfamoyl group), etc., and in the compounds shown in Tables 1Z6 to 4Z6 -SO ₂ N (R ^102AZ6X ) ₂ (R ^102AZ6X is and a group corresponding to R ^102AZ6 except that it does not become a hydrogen atom), preferably a sulfamoyl group substituted with one or two C1-C10 hydrocarbon groups or derivatized groups thereof, and Tables In the compound _shown in 1Z6 - Table 4Z6, the group corresponding to -SO2N(R ^102AZ6 ) ₂ , etc. are mentioned.

As -CON(R ^102AZ6 ) ₂ , a carbamoyl group; N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarp Bamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N-(1-ethylpropyl)carbamoyl group, N-hexylcarbamoyl group, N-(2-ethyl)hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group and N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N-icosylcarbamo group A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) and Tables 1Z6 to 4Z6 In the compound represented by -CONH(R ^102AZ6X ) (R ^102AZ6X is the same as R ^102AZ6 except that it does not become a hydrogen atom), etc.;

N,N-dimethylcarbamoyl group, N,N-ethylmethylcarbamoyl group, N,N-diethylcarbamoyl group, N,N-propylmethylcarbamoyl group, N,N-dipropylcarbamoyl group, N ,N-isopropylmethylcarbamoyl group, N,N-diisopropylcarbamoyl group, N,N-tert-butylmethylcarbamoyl group, N,N-diisobutylcarbamoyl group, N,N-disec -Butylcarbamoyl group, N,N-ditert-butylcarbamoyl group, N,N-butylmethylcarbamoyl group, N,N-dibutylcarbamoyl group, N,N-butyloctylcarbamoyl group, N, N-dipentylcarbamoyl group, N,N-di(1-ethylpropyl)carbamoyl group, N,N-dihexylcarbamoyl group, N,N-di(2-ethyl)hexylcarbamoyl group, N, N-diheptylcarbamoyl group, N,N-octylmethylcarbamoyl group, N,N-dioctylcarbamoyl group, N,N-dinonylcarbamoyl group, N,N-decylmethylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N,N-dodecylmethylcarbamoyl group, N,N-icosylmethylcarbamoyl group, N,N-phenylmethylcarbamoyl group, N,N-diphenylcarbamoyl group and two hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably preferably a chlorine atom), a carbamoyl group substituted with a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and -CON in the compounds shown in Tables 1Z6 to 4Z6 ( and groups corresponding to R ^102AZ6X ) ₂ (R ^102AZ6X is the same as R ^102AZ6 except that it does not become a hydrogen atom);

Preferably, a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, and a group corresponding to -CON(R ^102AZ6 ) ₂ in the compounds shown in Tables 1Z6 to 4Z6, etc. there is.

-N(R ^102AZ6 ) ₂ is an amino group; N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group , N-hexylamino group, N-(2-ethyl)hexylamino group, N-heptylamino group, N-octylamino group, N-nonylamino group, N-decylamino group, N-undecylamino group, N-dodecylamino group, N- A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms), such as an icosylamino group, N-phenylamino group, and a group represented by the above formula, or a derivatized group thereof (for example, a carboxy group, a sulfo group, An amino group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a group derivatized with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like shown in Tables 1Z6 to 4Z6 Group corresponding to -NH(R ^102AZ6X ) (provided that R ^102AZ6X is the same as R ^102AZ6 except that it does not become a hydrogen atom) in a compound, etc.;

N,N-dimethylamino group, N,N-ethylmethylamino group, N,N-diethylamino group, N,N-propylmethylamino group, N,N-dipropylamino group, N,N-isopropylmethylamino group, N, N-diisopropylamino group, N,N-tert-butylmethylamino group, N,N-diisobutylamino group, N,N-disec-butylamino group, N,N-ditert-butylamino group, N,N- Butylmethylamino group, N,N-dibutylamino group, N,N-dipentylamino group, N,N-di(1-ethylpropyl)amino group, N,N-dihexylamino group, N,N-di(2-ethyl) ) hexylamino group, N,N-diheptylamino group, N,N-dioctylamino group, N,N-dinonylamino group, N,N-decylmethylamino group, N,N-undecylmethylamino group, N,N-dode A sylmethylamino group, N,N-icosylmethylamino group, N,N-phenylmethylamino group, N,N-diphenylamino group, etc., and groups represented by the above formulas, such as groups having 1 to 40 carbon atoms (preferably carbon atoms) 1 to 20) a hydrocarbon group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamo) -N(R ^102AZ6X ) ₂ (provided that R ^102AZ6X is the same as R ^102AZ6 except that it does not become a hydrogen atom) In the compounds shown in Tables 1Z6 to 4Z6 and an amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms or a derivatized group thereof, preferably -N(R ^102AZ6 ) ₂ and groups corresponding to .

-NHCO-R ^{102AZ6 is} a formylamino group; Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl)hexanoylamino group, heptanoylamino group, octanoylamino group, nonanoyl Hydrocarbons having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as amino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group, and groups represented by the above formulas derivatized with a group or a derivatized group thereof (for example, a carboxy group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc. group) to which the carbonylamino group is bonded (when the carbonylamino group is an acylamino group, it has 1 to 40 carbon atoms) and a group corresponding to -NHCO-R ^102AZ6 in the compounds shown in Tables 1Z6 to 4Z6. and preferably a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivatized group thereof is bonded (when the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10) and Tables 1Z6 to 4Z6 In the compound represented by -NHCO-R ^102AZ6 , the group etc. are mentioned.

Examples of -NHCON(R ^102AZ6 ) ₂ include the groups listed above and groups corresponding to -NHCON(R ^102AZ6 ) ₂ in the compounds shown in Tables 1Z6 to 4Z6.

Examples of -NHCOOR ^102AZ6 include the groups listed above and groups corresponding to -NHCOOR ^102AZ6 in the compounds shown in Tables 1Z6 to 4Z6.

Examples of -OCON(R ^102AZ6 ) ₂ include the groups listed above and groups corresponding to -OCON(R ^102AZ6 ) ₂ in the compounds shown in Tables 1Z6 to 4Z6.

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are preferable.

As M of -SO ₃ M and -CO ₂ M, a hydrogen atom; Alkali metal atoms, such as a lithium atom, a sodium atom, and a potassium atom, are mentioned, Preferably, a hydrogen atom, a sodium atom, and a potassium atom are mentioned.

The -CO-R ^102AZ6 , -COO-R ^102AZ6 , -OCO-R ^102AZ6 , -COCO-R ^102AZ6 , -OR ^102AZ6 , -SO ₂ -R ^102AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ , -N(R ^102AZ6 ) ₂ , -NHCO-R ^102AZ6 , -NHCON(R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , -OCON(R ^102AZ6 ) ₂ Substituents (first substituents) included in 2 are one Or two or more may be sufficient, and two or more substituents mutually independently may be same or different.

In addition, as for the said 1st substituent, the other substituent (2nd substituent) may couple|bond with the hydrocarbon group contained in the part. The second substituent can be selected from the same groups as the first substituent.

R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 include a hydrogen atom, -CO-R ^102AZ6 , -COO-R ^101AZ6 , -COCO-R ^102AZ6 , - OR ^102AZ6 , -SO ₂ -R ^101AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ , -N(R ^102AZ6 ) ₂ , -NHCO-N(R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , -OCON(R ^102AZ6 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, -SO ₃ ^- , -CO ₂ ^- , a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or The heterocyclic group which may have a substituent is preferable.

R ^101AZ6 is preferably a C1-C40 hydrocarbon group which may have a substituent.

As R ^102AZ6 , a hydrogen atom or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent is preferable.

The ring formed by ^R2AZ6 and ^R3AZ6 , ^R3AZ6 and ^R4AZ6 , and ^R4AZ6 and ^R5AZ6 is condensed with the benzene ring of the isoindoline skeleton of the compound represented by Formula IZ6. Examples of the condensed ring structure of the benzene ring and the ring formed by R ^2AZ6 and R ^3AZ6 , R ^3AZ6 and R ^4AZ6 , and R ^4AZ6 and R ^5AZ6 include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, and phenylene. nalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysene, N-methylphthalimide, N-(1-phenylethyl)phthalimide and tetracene hydrocarbon-based condensed ring structures and partial reduction products thereof (eg, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); Indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, perimidine, phenanthroline and phenazine, etc. of nitrogen-containing condensed heterocycles and partial reduction products thereof; and oxygen-containing condensed heterocycles such as 3-hydrobenzofuran 2-one, and partially reduced products thereof.

When R ^2AZ6 and R ^3AZ6 , R ^3AZ6 and R ^4AZ6 , and R ^4AZ6 and R ^5AZ6 form a ring, the ring may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

When R ^3AZ6 and R ^4AZ6 form a ring, R ^2AZ6 and R ^5AZ6 are each independently preferably a hydrogen atom, an amino group or a hydroxy group.

When R ^2AZ6 and R ^3AZ6 form a ring, it is preferable that R ^4AZ6 and R ^5AZ6 do not form a ring, and it is more preferable that R ^4AZ6 and R ^5AZ6 are hydrogen atoms.

Moreover, when R ^4AZ6 and R ^5AZ6 form a ring, it is preferable that R ^2AZ6 and R ^3AZ6 do not form a ring, and it is more preferable that R ^2AZ6 and R ^3AZ6 are a hydrogen atom.

The ring formed by R ^AA1Z6 and R ^AA2Z6 , and R ^12AZ6 and R ^13AZ6 is bonded to exomethylene (C═CH ₂ ) of the isoindoline skeleton of formula IZ6, R ^AA1Z6 and R ^AA2Z6 , and R ^12AZ6 and R ^13AZ6 If the ring formed is taken as a structure containing this exomethylene (C = CH ₂ ), for example, a structure in which a carbonyl group, exomethylene and carbonyl group such as the following group A and group B are arranged in this order can be exemplified. . ** represents a bond with isoindoline skeleton.

[Group A]

[Group B]

R ^104AZ6 , R ^105AZ6 , R ^106AZ6 , and R ^107AZ6 are, independently of each other, a hydrogen atom, -CO-R ^102AZ6 , -COO-R ^101AZ6 , -OCO-R ^102AZ6 , -COCO-R ^102AZ6 , -OR ^102AZ6 , - SO ₂ -R ^101AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ , -N(R ^102AZ6 ) ₂ , -NHCO-R ^102AZ6 , -NHCO-N(R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , -OCON(R ^102AZ6 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, -SO ₃ ^- , -CO ₂ ^- , a C1-C40 hydrocarbon which may have a substituent The heterocyclic group which may have a group or a substituent is shown.

-CO-R ^102AZ6 , -COO-R ^101AZ6 , -OCO-R ^102AZ6 , -COCO-R ^102AZ6 , -OR ^102AZ6 , -SO ₂ -R ^101AZ6 , represented by R ^104AZ6 , R ^105AZ6 , R ^106AZ6 , and R ^107AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ , -N(R ^102AZ6 ) ₂ , -NHCO-R ^102AZ6 , -NHCO-N(R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , -OCON(R ^102AZ6 ) ₂ , a halogen atom, -SO ₃ M and -CO ₂ M are -CO-R represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^{13AZ6 102AZ6} , -COO-R ^101AZ6 , -OCO-R ^102AZ6 , -COCO-R ^102AZ6 , -OR ^102AZ6 , -SO ₂ -R ^101AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ , - N(R ^102AZ6 ) ₂ , -NHCO-R ^102AZ6 , -NHCO-N(R ^102AZ6 ) ₂ , -NHCOOR ^102AZ6 , -OCON(R ^102AZ6 ) ₂ , halogen atom, -SO ₃ M and -CO ₂ M the same can be heard

Examples of the hydrocarbon group having 1 to 40 carbon atoms which may have a substituent and the heterocyclic group which may have a substituent represented by R ^104AZ6 , R ^105AZ6 , R ^106AZ6 , and R ^107AZ6 include R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same substituents as the hydrocarbon group having 1 to 40 carbon atoms or the heterocyclic group which may have a substituent.

The hydrocarbon group and heterocyclic group having 1 to 40 carbon atoms represented by R ^104AZ6 , R ^105AZ6 , R ^106AZ6 , and R ^107AZ6 may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

R ^104AZ6 , R ^105AZ6 , R ^106AZ6 , and R ^107AZ6 are preferably the same as those preferred for R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 can be heard

R ^104AZ6 , R ^105AZ6 , R ^106AZ6 , and R ^107AZ6 are more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, and a (2-ethyl)hexyl group. , a hydrocarbon group having 1 to 10 carbon atoms, such as a heptyl group, an octyl group, a nonyl group, a cyclohexyl group and a phenyl group, and a hydrogen atom.

The groups exemplified in Group A and Group B may be those in which a hydrogen atom bonded to a ring structure is substituted with a substituent.

^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Among the substituents, preferred ones are preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

R ^1AZ6 is a hydrogen atom, R ^2AZ6 , R ^3AZ6 , R ^4AZ6 and R ^5AZ6 are, independently of each other,

A hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102AZ6 ) ₂ , a nitro group, a hydrocarbon group having 1 to 20 carbon atoms in which all or part of the hydrogen atoms are substituted with fluorine atoms, -NHCO-R ^102AZ6 , -OR ^102AZ6 , -SO ₃ M or -CO ₂ M is preferred,

It is more preferable that they are a hydrogen atom, a tert- butyl group, or a nitro group.

R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 is at least one of (raa-i) to (raa-iii) Preferably, R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 have -SO ₃ ^- or -CO ₂ ^- The total number is a.

(raa-i) At least one of R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 is -SO ₃ ^- or -CO ₂ ^- .

(raa-ii) at least one of R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 is -CO-R ^102AZ6 , -COO-R ^101AZ6 , -OR ^102AZ6 , -SO ₂ -R ^101AZ6 , -SO ₂ N(R ^102AZ6 ) ₂ , -CON(R ^102AZ6 ) ₂ or -N(R ^102AZ6 ) ₂ , and R ^101AZ6 and R ^102AZ6 are, -SO ₃ ^- or - It is a C1-C40 hydrocarbon group having CO ₂ ^- or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(raa-iii) at least one of R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 has -SO ₃ ^- or -CO ₂ ^- having 1 to It is a hydrocarbon group of 40 or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . The hydrocarbon group or the heterocyclic group may have a substituent other than -SO ₃ ^- and -CO ₂ ^- .

As said group A and group B, the ring represented by a formula (QQ1) - a formula (QQ25) and a formula (QQA1) - a formula (QQA36) is mentioned

The compound represented by the formula IZ6-A is preferably a compound represented by the formula IZ6-B (hereinafter, sometimes referred to as compound IZ6-B).

[In formula IZ6-B, A ^c+ , b, c, d and the broken line represent the same meanings as above. L ¹ represents -CO- or -SO ₂ -. R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 , and R ^13BZ6 are, independently of each other, a hydrogen atom, -CO-R ^102BZ6 , -COO-R ^101BZ6 , -OCO-R ^102BZ6 , -COCO-R ^102BZ6 , -OR ^102BZ6 , -SO ₂ -R ^101BZ6 , -SO ₂ N(R ^102BZ6 ) ₂ , -CON(R ^102BZ6 ) ₂ , -N(R ^102BZ6 ) ₂ , -NHCO-R ^102BZ6 , -NHCO-N(R ^102BZ6 ) ₂ , -NHCOOR ^102BZ6 , -OCON(R ^102BZ6 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, -SO ₃ ^- , -CO ₂ ^- , a C1-C40 hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent.

R ^2BZ6 and R ^3BZ6 , R ^3BZ6 and R ^4BZ6 , R ^4BZ6 and R ^5BZ6 , and R ^12BZ6 and R ^13BZ6 may be respectively bonded to each other to form a ring.

R ^101BZ6 represents, independently of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102BZ6 represents, each independently, a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

Formula IZ6-B' and Formula IZ6-B" each represent a partial structure of Formula IZ6-B, A ^c+ , b, c, d, R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 , R ^13BZ6 , and L ¹ represent the same as those in formula IZ6-B.

M has the same meaning as above.

When a ^plurality of R 1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 , R ^13BZ6 , R ^101BZ6 , R ^102BZ6 , L ¹ , M, c or A ^c+ exists, each of them may be the same , may be different.

R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 , R ^13BZ6 , R ^101BZ6 and R ^102BZ6 satisfy at least one of (rb-i) to (rb-iii); , R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 , R ^13BZ6 , R ^101BZ6 and R ^102BZ6 have -SO ₃ ^- or -CO ₂ ^- The total number is a.

(rb-i) At least one of R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 and R ^13BZ6 is —SO ₃ ^— or —CO ₂ ^— .

(rb-ii) at least one of R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 and R ^13BZ6 is -CO-R ^102BZ6 , -COO-R ^101BZ6 , -OCO-R ^102BZ6 , -COCO-R ^102BZ6 , -OR ^102BZ6 , -SO ₂ -R ^101BZ6 , -SO ₂ N(R ^102BZ6 ) ₂ , -CON(R ^102BZ6 ) ₂ , -N(R ^102BZ6 ) ₂ , -NHCO-R ^102BZ6 , -NHCO-N(R ^102BZ6 ) ₂ , -NHCOOR ^102BZ6 , or -OCON(R ^102BZ6 ) ₂ , wherein R ^101BZ6 and R ^102BZ6 are -SO ₃ ^- or -CO ₂ ^- A hydrocarbon group having 1 to 40 carbon atoms Or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(rb-iii) At least one of R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 and R ^13BZ6 is -SO ₃ ^- or -CO ₂ ^- A hydrocarbon having 1 to 40 carbon atoms It is a heterocyclic group having a group or -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

a has the same meaning as that in the formula IZ6-A. When a plurality of as exist, they may be the same or different.

The absolute value of the negative valence of the partial structure represented by the formula IZ6-B' and the positive valence of the partial structure represented by the formula IZ6-B" are the same.]

As R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 and R ^13BZ6 , R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R 5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^AA2Z6 , R ^AA2Z6 The same thing as ^13AZ6 is mentioned.

R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 and R ^13BZ6 are preferably R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA1Z6 . The same thing as the preferable thing of ^12AZ6 and R ^13AZ6 is mentioned.

As R ^101BZ6 , the thing similar to R ^101AZ6 is mentioned. As a preferable thing of R ^101BZ6 , the thing similar to the preferable thing of R ^101AZ6 is mentioned.

As R ^102BZ6 , the thing similar to R ^102AZ6 is mentioned. As a preferable thing of R ^102BZ6 , the thing similar to the preferable thing of R ^102AZ6 is mentioned. The hydrocarbon group and heterocyclic group having 1 to 40 carbon atoms represented by R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 , R ^13BZ6 , R ^101BZ6 and R ^102BZ6 and the heterocyclic group may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

L ¹ is preferably -CO-.

R ^11BZ6 is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, and a thienyl group which may have a substituent , it is preferably a furyl group which may have a substituent or a pyridinyl group which may have a substituent.

Carbon number of the aliphatic hydrocarbon group represented by R ^11BZ6 is 1-40, Preferably it is 1-30, More preferably, it is 1-20, More preferably, it is 1-15.

The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain aliphatic hydrocarbon group represented by R ^11BZ6 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, and a heptade group. straight-chain alkyl groups such as an actual group, an octadecyl group and an icosyl group; isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, (2-ethyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl)pentyl group, (2- methyl) pentyl group, (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group and (3-ethyl) heptyl group branched-chain alkyl groups and the like; Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-pro alkenyl groups such as phenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl; and the like. The number of carbon atoms in the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ^11BZ6 include a cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, and 2-methyl group. Cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethyl Cyclohexyl 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, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetra a methylcyclohexyl group and a 3,3,5,5-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, and a cycloalkyl group such as a 4-cyclohexylcyclohexyl group; Cycloalkenyl groups, such as a cyclohexenyl group (For example, cyclohexa-2-ene, cyclohexa-3-ene), a cycloheptenyl group, and a cyclooctenyl group; norbornane group, adamantyl group, bicyclo[2.2.2]octane, etc. are mentioned. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, still more preferably 4 to 20 carbon atoms, still more preferably 4 to 15 carbon atoms, and particularly more Preferably it is 5-15, Most preferably, it is 5-10. Among these, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group are particularly preferable.

The aliphatic hydrocarbon group represented by R ^11BZ6 may be a group in which a hydrogen atom contained in the above-mentioned aliphatic hydrocarbon group is substituted with an aromatic hydrocarbon group having 1 to 40 carbon atoms, or a group in which the above-mentioned aliphatic hydrocarbon group is combined.

As such an aromatic hydrocarbon group, a phenyl group, o-tolyl group, m-tolyl group, p-tolyl 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, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert -Butylphenyl group, mesityl group, 2,6-bis(2-propyl)phenyl group, 2,4,6-trimethylphenyl group, 1-naphthyl group, 2-naphthyl group, 5,6,7,8-tetrahydro-1 -Aromatic hydrocarbon groups, such as a naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, and an anthryl group; and the like. Carbon number of the said aromatic hydrocarbon group becomes like this. Preferably it is 6-30, More preferably, it is 6-20, More preferably, it is 6-15.

Examples of the group in which an aromatic hydrocarbon group having 1 to 40 carbon atoms are substituted for a hydrogen atom contained in the aliphatic hydrocarbon group mentioned above include an aralkyl group such as a benzyl group, a phenethyl group and a 1-methyl-1-phenylethyl group. As a group combining the aliphatic hydrocarbon groups mentioned above, (cycloalkyl)alkyl groups, such as a cyclohexylmethyl group, etc. are mentioned. The group in which the hydrogen atom contained in the aliphatic hydrocarbon group is substituted with an aromatic hydrocarbon group having 1 to 40 carbon atoms or the group in which an aliphatic hydrocarbon group is combined has preferably 4 to 30 carbon atoms, more preferably 4 to 20 carbon atoms, and still more preferably is 4 to 15.

The aliphatic hydrocarbon group having 1 to 40 carbon atoms, phenyl group, naphthyl group, tetrahydronaphthyl group, thienyl group, furyl group and pyridinyl group represented by R ^11BZ6 may have a substituent.

^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

In the compound IZ6-B, R ^1BZ6 is preferably a hydrogen atom.

R ^2BZ6 , R ^3BZ6 , R ^4BZ6 or R ^5BZ6 is, independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102BZ6 ) ₂ , a nitro group, or all or part of a fluorine atom It is preferable that it is a C1-C20 hydrocarbon group substituted by the atom, -NHCO-R ^102BZ6 , -OR ^102BZ6 , -SO ₃ M, or -CO ₂ M, and it is more preferable that it is a hydrogen atom or a nitro group. The number of nitro groups becomes like this. Preferably it is 0-2, More preferably, it is 0 or 1 piece.

R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 , R ^13BZ6 , R ^101BZ6 and R ^{102BZ6 preferably} satisfy at least one of (rbb-i) to (rbb-iii) Preferably, the total number of -SO ₃ ^- or -CO ₂ ^- in R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 , R ^13BZ6 , R ^101BZ6 and R ^102BZ6 is a.

(rbb-i) At least one of R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 and R ^13BZ6 is —SO ₃ ^— or —CO ₂ ^— .

(rbb-ii) at least one of R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 and R ^13BZ6 is -CO-R ^102BZ6 , -COO-R ^101BZ6 , -OR ^102BZ6 , - SO ₂ -R ^101BZ6 , -SO ₂ N(R ^102BZ6 ) ₂ , -CON(R ^102BZ6 ) ₂ or -N(R ^102BZ6 ) ₂ , wherein R ^101BZ6 and R ^102BZ6 are -SO ₃ ^- or -CO ₂ ^- is a hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(rbb-iii) at least one of R ^1BZ6 , R ^2BZ6 , R ^3BZ6 , R ^4BZ6 , R ^5BZ6 , R ^11BZ6 , R ^12BZ6 and R ^13BZ6 is -SO ₃ ^- or -CO ₂ ^- A hydrocarbon having 1 to 40 carbon atoms It is a heterocyclic group having a group or -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

In the formula IZ6-B, when R ^12BZ6 and R ^13BZ6 do not form a ring, the compound IZ6-B is preferably a compound represented by the formula IZ6-C (hereinafter sometimes referred to as compound IZ6-C). Do.

[In formula IZ6-C, A ^c+ , b, c, d, L ¹ and the broken line represent the same meanings as above.

L ² represents -CO- or -SO ₂ -. R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 and R ^14CZ6 are, independently of each other, a hydrogen atom, -CO-R ^102CZ6 , -COO-R ^101CZ6 , -OCO-R ^102CZ6 , -COCO- R ^102CZ6 , -OR ^102CZ6 , -SO ₂ -R ^101CZ6 , -SO ₂ N(R ^102CZ6 ) ₂ , -CON(R ^102CZ6 ) ₂ , -N(R ^102CZ6 ) ₂ , -NHCO-R ^102CZ6 , -NHCO-N (R ^102CZ6 ) ₂ , -NHCOOR ^102CZ6 , -OCON(R ^102CZ6 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, -SO ₃ ^- , -CO ₂ ^- , have a substituent It represents the optionally C1-C40 hydrocarbon group or the heterocyclic group which may have a substituent.

R ^2CZ6 and R ^3CZ6 , R ^3CZ6 and R ^4CZ6 , and R ^4CZ6 and R ^5CZ6 may be respectively bonded to each other to form a ring.

R ^101CZ6 represents, independently of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102CZ6 represents, each independently, a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M has the same meaning as above.

Formula IZ6-C' and formula IZ6-C" represent a partial structure of formula IZ6-C, respectively, and A ^c+ , b, c, d, R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , L ¹ , and L ² each represent the same as in formula IZ6-C.

When a ^plurality of R 1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 , R ^102CZ6 , L ¹ , L ² , M, c or A ^c+ exists, each of them may be the same , may be different.

R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 and R ^102CZ6 satisfy at least one of (rc-i) to (rc-iii), and R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 and R ^102CZ6 The total number of -SO ₃ ^- or -CO ₂ ^- is a.

(rc-i) At least one of R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 and R ^14CZ6 is —SO ₃ ^— or —CO ₂ ^— .

(rc-ii) at least one of R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 and R ^14CZ6 is -CO-R ^102CZ6 , -COO-R ^101CZ6 , -OCO-R ^102CZ6 , -COCO -R ^102CZ6 , -OR ^102CZ6 , -SO ₂ -R ^101CZ6 , -SO ₂ N(R ^102CZ6 ) ₂ , -CON(R ^102CZ6 ) ₂ , -N(R ^102CZ6 ) ₂ , -NHCO-R ^102CZ6 , -NHCO- N(R ^102CZ6 ) ₂ , -NHCOOR ^102CZ6 , or -OCON(R ^102CZ6 ) ₂ , wherein R ^101CZ6 and R ^102CZ6 are -SO ₃ ^- or -CO ₂ ^- A hydrocarbon group having 1 to 40 carbon atoms or -SO ₃ ^- or -CO ₂ ^- is a heterocyclic group. The hydrocarbon group or the heterocyclic group may have a substituent other than -SO ₃ ^- and -CO ₂ ^- .

(rc-iii) at least one of R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 and R ^14CZ6 is -SO ₃ ^- or -CO ₂ ^- A hydrocarbon group having 1 to 40 carbon atoms or - SO ₃ ^- or -CO ₂ ^- is a heterocyclic group. However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

a has the same meaning as in formula IZ6-B. When a plurality of as exist, they may be the same or different.

The absolute value of the negative valence of the partial structure represented by the formula IZ6-C' and the positive valence of the partial structure represented by the formula IZ6-C" are the same.]

R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 and R ^14CZ6 are the same as R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R AA1Z6 , R ^AA2Z6 13 R ^{12 AZ} , R ^AA2Z6 , R ^AA2Z6 thing can be heard Preferred examples of R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 and R ^14CZ6 include R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^AA2Z6 and R AA2Z6 . The same thing as the preferable thing of ^13AZ6 is mentioned.

As R ^101CZ6 , the thing similar to R ^101AZ6 is mentioned. As a preferable thing of R ^101CZ6 , the thing similar to the preferable thing of R ^101AZ6 is mentioned.

As R ^102CZ6 , the thing similar to R ^102AZ6 is mentioned. As a preferable thing of R ^102CZ6 , the thing similar to the preferable thing of R ^102AZ6 is mentioned.

The hydrocarbon group and heterocyclic group having 1 to 40 carbon atoms represented by R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 and R ^102CZ6 and the heterocyclic group may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

It is preferable that L ¹ or L ² is -CO-. It is preferable that R ^11CZ6 and R ^14CZ6 are the same group, and L ¹ and L ² are the same group.

R ^11CZ6 and R ^14CZ6 are, independently of each other, an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, It is preferable that they are the thienyl group which may have a substituent, the furyl group which may have a substituent, or the pyridinyl group which may have a substituent.

An aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have such a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, and a substituent As the furyl group which may have or the pyridinyl group which may have a substituent, it has the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, which is mentioned as a preferable thing for R ^11BZ6 in compound IZ6-B, and a substituent. phenyl group which may have a substituent, a naphthyl group which may have a substituent, tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridinyl group which may have a substituent. there is.

In compound IZ6-C, R ^1CZ6 is preferably a hydrogen atom.

R ^2CZ6 , R ^3CZ6 , R ^4CZ6 and R ^5CZ6 are, independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102CZ6 ) ₂ , a nitro group, or all or part of a fluorine atom It is preferable that it is a C1-C20 hydrocarbon group substituted by the atom, -NHCO-R ^102CZ6 , -OR ^102CZ6 , -SO ₃ M, or -CO ₂ M, and it is more preferable that it is a hydrogen atom or a nitro group. The number of nitro groups becomes like this. Preferably it is 0-2, More preferably, it is 0 or 1 piece.

R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 and R ^102CZ6 preferably satisfy at least one of (rcc-i) to (rcc-iii), The total number of -SO ₃ ^- or -CO ₂ ^- in R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 and R ^102CZ6 is a.

(rcc-i) At least one of R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , and R ^14CZ6 is —SO ₃ ^— or —CO ₂ ^— .

(rcc-ii) at least one of R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 and R ^14CZ6 is -CO-R ^102CZ6 , -COO-R ^101CZ6 , -COCO-R ^102CZ6 , -OR ^102CZ6 , -SO ₂ -R ^101CZ6 , -SO ₂ N(R ^102CZ6 ) ₂ , -CON(R ^102CZ6 ) ₂ , -N(R ^102CZ6 ) ₂ , -NHCO-N(R ^102CZ6 ) ₂ , -NHCOOR ^102CZ6 , or -OCON(R ^102CZ6 ) ₂ , wherein R ^101CZ6 and R ^102CZ6 are a hydrocarbon group having 1 to 40 carbon atoms having -SO ₃ ^- or -CO ₂ ^- or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(rcc-iii) at least one of R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 and R ^14CZ6 is -SO ₃ ^- or -CO ₂ ^- A hydrocarbon group having 1 to 40 carbon atoms or - SO ₃ ^- or -CO ₂ ^- is a heterocyclic group. However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 and R ^102CZ6 preferably satisfy at least one of (rc-I) and (rc-II).

(rc-I) At least one of R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , and R ^5CZ6 is —SO ₃ ^— or —CO ₂ ^— .

(rc-II) At least one of R ^1CZ6 , R ^11CZ6 and R ^14CZ6 is a hydrocarbon group having 1 to 40 carbon atoms or -SO ₃ ^- or -CO ₂ which may have a substituent having -SO ₃ ^- or -CO ₂ ^{- -} is a heterocyclic group with However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 and R ^102CZ6 preferably satisfy at least one of (rcc-I) and (rcc-II).

(rcc-I) At least one of R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , and R ^5CZ6 is —SO ₃ ^— or —CO ₂ ^— .

(rcc-II) At least one of R ^1CZ6 , R ^11CZ6 and R ^14CZ6 is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent having —SO ₃ ^— or —CO ₂ ^— . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

However, the total number of -SO ₃ ^- or -CO ₂ ^- of R ^1CZ6 , R ^2CZ6 , R ^3CZ6 , R ^4CZ6 , R ^5CZ6 , R ^11CZ6 , R ^14CZ6 , R ^101CZ6 and R ^102CZ6 is a.

In the compound IZ6-B, when R ^12BZ6 and R ^13BZ6 form a ring, the compound IZ6-B is preferably a compound represented by the formula IZ6-D (hereinafter sometimes referred to as compound IZ6-D). .

[In formula IZ6-D, A ^c+ , b, c, d, L ¹ and the broken line represent the same meanings as above. R ^20DZ6 and R ^30DZ6 combine to form ring Q. Ring Q may have a substituent, the number of ring members is a ring of 5-7, and the said ring Q may be a hydrocarbon ring or a heterocyclic ring may be sufficient as it. In ring Q, a monocyclic ring selected from a hydrocarbon ring and a heterocyclic ring, which may have a substituent having 5 to 7 ring members, or a condensed ring obtained by condensing two or more of the monocyclic ring may be condensed.

R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 are, independently of each other, a hydrogen atom, -CO-R ^102DZ6 , -COO-R ^101DZ6 , -OCO-R ^102DZ6 , -COCO-R ^102DZ6 , -OR ^102DZ6 , -SO ₂ -R ^101DZ6 , -SO ₂ N(R ^102DZ6 ) ₂ , -CON(R ^102DZ6 ) ₂ , -N(R ^102DZ6 ) ₂ , -NHCO-R ^102DZ6 , -NHCO-N(R ^{102DZ6 )} ) ₂ , -NHCOOR ^102DZ6 , -OCON(R ^102DZ6 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, -SO ₃ ^- , -CO ₂ ^- , carbon number which may have a substituent It represents the hydrocarbon group of 1-40 or the heterocyclic group which may have a substituent.

R ^2DZ6 and R ^3DZ6 , R ^3DZ6 and R ^4DZ6 , and R ^4DZ6 and R ^5DZ6 may be respectively bonded to each other to form a ring. R ^101DZ6 represents, each independently, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102DZ6 represents, each independently, a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M has the same meaning as above.

Formula IZ6-D' and formula IZ6-D" represent the partial structure of formula IZ6-D, respectively, and A ^c+ , b, c, d, R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 , R ^11DZ6 , R ^20DZ6 , R ^30DZ6 , and L ¹ represent the same as those in formula IZ6-D.

R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 , R ^11DZ6 , R ^101DZ6 , R ^102DZ6 , L ¹ , M, R ^20DZ6 , R ^30DZ6 , when a plurality of rings Q, c or A ^c+ exist, they are each They may be the same or different.

R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 , R ^11DZ6 , R ^101DZ6 , R ^102DZ6 and ring Q satisfy at least one of (rd-i) to (rd-iv), and R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 , R ^11DZ6 , R ^101DZ6 , R ^102DZ6 and the total number of —SO ₃ ^— or —CO ₂ ^— in the ring Q is a.

(rd-i) At least one of R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 is —SO ₃ ^— or —CO ₂ ^— .

(rd-ii) at least one of R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 is -CO-R ^102DZ6 , -COO-R ^101DZ6 , -OCO-R ^102DZ6 , -COCO-R ^102DZ6 , -OR ^102DZ6 , -SO ₂ -R ^101DZ6 , -SO ₂ N(R ^102DZ6 ) ₂ , -CON(R ^102DZ6 ) ₂ , -N(R ^102DZ6 ) ₂ , -NHCO-R ^102DZ6 , -NHCO-N(R ^102DZ6 ) ₂ , -NHCOOR ^102DZ6 , or -OCON(R ^102DZ6 ) ₂ , wherein R ^101DZ6 and R ^102DZ6 are -SO ₃ ^- or -CO ₂ ^- A hydrocarbon group having 1 to 40 carbon atoms or -SO ₃ ^- or It is a heterocyclic group having -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(rd-iii) at least one of R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 is -SO ₃ ^- or -CO ₂ ^- A hydrocarbon group having 1 to 40 carbon atoms or -SO ₃ ^- Or -CO ₂ ^- is a heterocyclic group having. The hydrocarbon group or the heterocyclic group may have a substituent other than -SO ₃ ^- and -CO ₂ ^- .

(rd-iv) Ring Q has -SO ₃ ^- or -CO ₂ ^- .

a has the same meaning as in formula IZ6-B. When a plurality of as exist, they may be the same or different.

The absolute value of the negative valence of the partial structure represented by the formula IZ6-D' and the positive valence of the partial structure represented by the formula IZ6-D" are the same.]

It is preferable that the number of members of a ring is 5-6.

It is preferable that these monocyclic or condensed rings combine with ring Q at two places to constitute a condensed ring.

Examples of the ring Q and the ring in which a monocyclic or condensed ring is condensed include the same ones as those of the group A above.

Among these, Preferably, a formula (Q1), a formula (Q4), a formula (Q7), a formula (Q8), and a formula (Q18) are mentioned, More preferably, a formula (Q8) and a formula (Q18) are mentioned can

The monocyclic ring selected from the hydrocarbon ring and heterocyclic ring which may be condensed to ring Q and ring Q and which may have a substituent having 5 to 7 ring members, or the condensed ring condensed by two or more of the monocyclic ring may have a substituent . ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} .

Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

As R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 , the same ^number of R 1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 as there is.

Preferred examples of R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 include R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 and R ^13AZ6 preferred. the same can be mentioned.

As R ^101DZ6 , the thing similar to R ^101AZ6 is mentioned. As a preferable thing of R ^101DZ6 , the thing similar to the preferable thing of R ^101AZ6 is mentioned.

As R ^102DZ6 , the thing similar to R ^102AZ6 is mentioned. As a preferable thing of R ^102DZ6 , the thing similar to the preferable thing of R ^102AZ6 is mentioned.

The hydrocarbon group and heterocyclic group having 1 to 40 carbon atoms represented by R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 , R ^11DZ6 , R ^101DZ6 and R ^102DZ6 may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

L ¹ is preferably -CO-.

R ^11DZ6 is, independently of each other, an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, and a substituent It is preferable that it is the thienyl group which may have an optionally, the furyl group which may have a substituent, or the pyridinyl group which may have a substituent.

An aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have such a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, and a substituent As the furyl group which may have or the pyridinyl group which may have a substituent, it has the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, which is mentioned as a preferable thing in R ^11BZ6 in compound IZ6-B, and a substituent. phenyl group which may have a substituent, a naphthyl group which may have a substituent, tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridinyl group which may have a substituent. there is.

In compound IZ6-D, R ^1DZ6 is preferably a hydrogen atom.

R ^2DZ6 , R ^3DZ6 , R ^4DZ6 and R ^5DZ6 are, independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102DZ6 ) ₂ , a nitro group, or all or a part of a fluorine atom It is preferable that it is a C1-C20 hydrocarbon group substituted by the atom, -NHCO-R ^102DZ6 , -OR ^102DZ6 , -SO ₃ M or -CO ₂ M, and it is more preferable that it is a hydrogen atom or a nitro group. The number of nitro groups becomes like this. Preferably it is 0-2, More preferably, it is 0 or 1 piece.

R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 , R ^11DZ6 , R ^101DZ6 , R ^102DZ6 and ring Q preferably satisfy at least one of (rdd-i) to (rdd-iv), The total number of R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 , R ^11DZ6 , R ^101DZ6 , R ^102DZ6 and —SO ₃ ^— or —CO ₂ ^— with ring Q is a.

(rdd-i) At least one of R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 is —SO ₃ ^— or —CO ₂ ^— .

(rdd-ii) at least one of R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 is -CO-R ^102DZ6 , -COO-R ^101DZ6 , -OR ^102DZ6 , -SO ₂ -R ^101DZ6 , -SO ₂ N(R ^102DZ6 ) ₂ , -CON(R ^102DZ6 ) ₂ or -N(R ^102DZ6 ) ₂ , wherein R ^101DZ6 and R ^102DZ6 have -SO ₃ ^- or -CO ₂ ^- having 1 to 40 carbon atoms. of a hydrocarbon group or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(rdd-iii) at least one of R ^1DZ6 , R ^2DZ6 , R ^3DZ6 , R ^4DZ6 , R ^5DZ6 and R ^11DZ6 is -SO ₃ ^- or -CO ₂ ^- A hydrocarbon group having 1 to 40 carbon atoms or -SO ₃ ^- Or -CO ₂ ^- is a heterocyclic group having. The hydrocarbon group or the heterocyclic group may have a substituent other than -SO ₃ ^- and -CO ₂ ^- .

(rdd-iv) Ring Q has -SO ₃ ^- or -CO ₂ ^- .

The compound IZ6-D is more preferably a compound represented by the formula IZ6-E (hereinafter, may be referred to as compound IZ6-E).

[In formula IZ6-E, A ^c+ , b, c, d, L ¹ and the broken line represent the same meanings as above.

R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 are, independently of each other, a hydrogen atom, -CO-R ^102EZ6 , -COO-R ^101EZ6 , -OCO-R ^102EZ6 , -COCO-R ^102EZ6 , -OR ^102EZ6 , -SO ₂ -R ^101EZ6 , -SO ₂ N(R ^102EZ6 ) ₂ , -CON(R ^102EZ6 ) ₂ , -N(R ^102EZ6 ) ₂ , -NHCO-R ^102EZ6 , - NHCO-N(R ^102EZ6 ) ₂ , -NHCOOR ^102EZ6 , -OCON(R ^102EZ6 ) ₂ , halogen atom, cyano group, nitro group, -SO ₃ M, -CO ₂ M, -SO ₃ ^- , -CO ₂ ^- , A C1-C40 hydrocarbon group which may have a substituent, or the heterocyclic group which may have a substituent is shown.

R ^2EZ6 and R ^3EZ6 , R ^3EZ6 and R ^4EZ6 , and R ^4EZ6 and R ^5EZ6 may be respectively bonded to each other to form a ring.

R ^101EZ6 represents, independently of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102EZ6 represents, each independently, a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M has the same meaning as above.

Formula IZ6-E' and formula IZ6-E" represent the partial structure of formula IZ6-E, respectively, and A ^c+ , b, c, d, R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 , R ^11EZ6 and L ¹ represent the same as in the formula IZ6-E.

When a ^plurality of R 1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 , R ^11EZ6 , R ^101EZ6 , R ^102EZ6 , L ¹ , M, c or A ^c+ exists, they may each be the same , may be different.

R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 , R ^11EZ6 , R ^101EZ6 and R ^102EZ6 satisfy at least one of (re-i) to (re-iii), , R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 , R ^11EZ6 , R ^101EZ6 and R ^102EZ6 The sum of -SO ₃ ^- or -CO ₂ ^- is a.

(re-i) at least one of R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 is —SO ₃ ^— or —CO ₂ ^— .

(re-ii) at least one of R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 is -CO-R ^102EZ6 , -COO-R ^101EZ6 , -OCO-R ^102EZ6 , -COCO-R ^102EZ6 , -OR ^101EZ6 , -SO ₂ -R ^101EZ6 , -SO ₂ N(R ^102EZ6 ) ₂ , -CON(R ^102EZ6 ) ₂ , -N(R ^102EZ6 ) ₂ , -NHCO-R ^102EZ6 , -NHCO-N(R ^102EZ6 ) ₂ , -NHCOOR ^102EZ6 , or -OCON(R ^102EZ6 ) ₂ , wherein R ^101EZ6 and R ^102EZ6 are -SO ₃ ^- or -CO ₂ ^- A hydrocarbon group having 1 to 40 carbon atoms Or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(re-iii) at least one of R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 is -SO ₃ ^- or -CO ₂ ^- A hydrocarbon having 1 to 40 carbon atoms It is a heterocyclic group having a group or -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

a has the same meaning as in formula IZ6-D. When a plurality of as exist, they may be the same or different.

The absolute value of the negative valence of the partial structure represented by the formula IZ6-E' and the positive valence of the partial structure represented by the formula IZ6-E" are the same.]

As R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 , R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 The same thing as ^13AZ6 is mentioned.

Preferred examples of R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 include R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^{5AZ6 , R AA1Z6} , R ^AA2Z6 , R ^AA2Z6 The same thing as the preferable thing of ^12AZ6 and R ^13AZ6 is mentioned.

R ^6EZ6 and R ^7EZ6 are, independently of each other, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a (2-ethyl)hexyl group, a heptyl group, an octyl group, It is preferable that they are a C1-C10 hydrocarbon group, such as a nonyl group, a cyclohexyl group, and a phenyl group, or a hydrogen atom.

As R ^101EZ6 , the thing similar to R ^101AZ6 is mentioned. As a preferable thing of R ^101EZ6 , the thing similar to the preferable thing of R ^101AZ6 is mentioned.

As R ^102EZ6 , the thing similar to R ^102AZ6 is mentioned. As a preferable thing of R ^102EZ6 , the thing similar to the preferable thing of R ^102AZ6 is mentioned.

The hydrocarbon group and heterocyclic group having 1 to 40 carbon atoms represented by R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 , R ^11EZ6 , R ^101EZ6 and R ^102EZ6 may have a substituent. ^Examples of the substituent include the same substituents as the substituents that the hydrocarbon group represented by R ^{1AZ6 , R 2AZ6 , R 3AZ6 , R 4AZ6 , R 5AZ6 , R AA1Z6 , R AA2Z6 , R 12AZ6 , R 13AZ6 , R 101AZ6 and R 102AZ6 may have .} . Preferred examples of the substituent include preferred substituents which the hydrocarbon group represented by R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 , R ^101AZ6 and R ^102AZ6 may have the same can be mentioned.

L ¹ is preferably -CO-.

R ^11EZ6 is, independently of each other, an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, and a substituent It is preferable that it is the thienyl group which may have an optionally, the furyl group which may have a substituent, or the pyridinyl group which may have a substituent.

An aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have such a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, and a substituent As the furyl group which may have or the pyridinyl group which may have a substituent, it has the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, which is mentioned as a preferable thing for R ^11BZ6 in compound IZ6-B, and a substituent. phenyl group which may have a substituent, a naphthyl group which may have a substituent, tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridinyl group which may have a substituent. there is.

In the compound IZ6-E, R ^1EZ6 is preferably a hydrogen atom.

R ^2EZ6 , R ^3EZ6 , R ^4EZ6 and R ^5EZ6 are, independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102EZ6 ) ₂ , a nitro group, all or part of a fluorine atom A hydrocarbon group having 1 to 20 atoms substituted with a hydrocarbon group, -NHCO-R ^102EZ6 , -OR ^102EZ6 , -SO ₃ M or -CO ₂ M is preferable,

It is more preferable that it is a hydrogen atom or a nitro group. The number of nitro groups becomes like this. Preferably it is 0-2, More preferably, it is 0 or 1 piece.

R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 , R ^11EZ6 , R ^101EZ6 and R ^102EZ6 must satisfy at least one of (ree-i) to (ree-iii) Preferably, R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 , R ^11EZ6 , R ^101EZ6 and R ^102EZ6 have -SO ₃ ^- or -CO ₂ ^- The total number of - is a.

(ree-i) At least one of R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 is —SO ₃ ^— or —CO ₂ ^— .

(ree-ii) at least one of R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 is, -CO-R ^102EZ6 , -COO-R ^101EZ6 , -OR ^102EZ6 , - SO ₂ -R ^101EZ6 , -SO ₂ N(R ^102EZ6 ) ₂ , -CON(R ^102EZ6 ) ₂ or -N(R ^102EZ6 ) ₂ , wherein R ^101EZ6 and R ^102EZ6 are, -SO ₃ ^- or -CO ₂ ^- is a hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(ree-iii) at least one of R ^1EZ6 , R ^2EZ6 , R ^3EZ6 , R ^4EZ6 , R ^5EZ6 , R ^6EZ6 , R ^7EZ6 and R ^11EZ6 is -SO ₃ ^- or -CO ₂ ^- A hydrocarbon having 1 to 40 carbon atoms It is a heterocyclic group having a group or -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

Specific examples of the compound IZ6 include compound IFZ6-1 to compound IFZ6-32, compound IGZ6-1 to compound IGZ6-32, compound IHZ6-32 shown in Tables 1Z6 to 4Z6 in Formulas IFZ6, IGZ6, Formula IHZ6, and Formula IJZ6 1 to compound IHZ6-32 and compound IJZ6-1 to compound IJZ6-32 are mentioned.

In the formulas IFZ6, IGZ6, IHZ6, and IJZ6, "-SO ₃ ^- " shall mean substituting any of the hydrogen atoms contained in the partial structures in parentheses, respectively.

[Table 1Z6]

[Table 2Z6]

[Table 3Z6]

[Table 4Z6]

For example, compound IFZ6-1 is a compound represented by formula IFZ6-1.

As compound IZ6, compound IFZ6-1 to compound IFZ6-4, compound IFZ6-6 to compound IFZ6-7, compound IFZ6-10 to compound IFZ6-13, compound IFZ6-15 to compound IFZ6-19, compound IFZ6-21 to compound IFZ6-22, compound IFZ6-25 to compound IFZ6-28 and compound IFZ6-30 to IFZ6-31; compound IGZ6-1 to compound IGZ6-4, compound IGZ6-6 to compound IGZ6-7, compound IGZ6-10 to compound IGZ6-13, compound IGZ6-15 to compound IGZ6-19, compound IGZ6-21 to compound IGZ6-22, compound IGZ6-25 to compound IGZ6-28 and compound IGZ6-30; compound IHZ6-1 to compound IHZ6-4, compound IHZ6-6 to compound IHZ6-7, compound IHZ6-10 to compound IHZ6-13, compound IHZ6-15 to compound IHZ6-19, compound IHZ6-21 to compound IHZ6-22, compound IHZ6-25 to compound IHZ6-28 and compound IHZ6-30; and compound IJZ6-1 to compound IJZ6-4, compound IJZ6-6 to compound IJZ6-7, compound IJZ6-10 to compound IJZ6-13, compound IJZ6-15 to compound IJZ6-19, compound IJZ6-21 to compound IJZ6-22 , compound IJZ6-25 to compound IJZ6-28 and compound IJZ6-30 are preferred,

compound IFZ6-1 to compound IFZ6-4, compound IFZ6-6 to compound IFZ6-7, compound IFZ6-10 to compound IFZ6-13, compound IFZ6-15 to compound IFZ6-19, compound IFZ6-21 to compound IFZ6-22, compound IFZ6-25 to compound IFZ6-28 and compound IFZ6-30; and compound IJZ6-1 to compound IJZ6-4, compound IJZ6-6 to compound IJZ6-7, compound IJZ6-10 to compound IJZ6-13, compound IJZ6-15 to compound IJZ6-19, compound IJZ6-21 to compound IJZ6-22 , compounds IJZ6-25 to IJZ6-28 and compounds IJZ6-30 to IJZ6-32 are more preferred.

As compound IZ6, in formula IZ6-C, L ¹ and L ² are the same group, -CO- or -SO ₂ -, preferably -CO-, R ^11CZ6 and R ^14CZ6 are the same group , hydroxy group, -O ^- , or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of, and R ^1CZ6 is , a hydrogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M, -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M,

R ^2CZ6 to R ^5CZ6 are each, independently, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102CZ6 ) ₂ , a nitro group, and 1 carbon atom in which all or part of a hydrogen atom is substituted with a fluorine atom to 20 hydrocarbon group, -NHCO-R ^102CZ6 , -OR ^102CZ6 , -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M, R ^102CZ6 is a hydrogen atom, or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of,

A ^c+ is Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Cd ²⁺ , Ni ²⁺ , Zn ²⁺ , Cu ²⁺ , Hg ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ^{2 +} , divalent metal cations such as Pb ²⁺ and Mn ²⁺ , trivalent metal cations such as Al ³⁺ , Fe ³⁺ and Cr ³⁺ , tetravalent metal cations such as Sn ⁴⁺ and Mn ⁴⁺ , M A compound of silver, a hydrogen atom or an alkali metal atom is preferable, L ¹ and L ² are the same group, are -CO- or -SO ₂ -, preferably -CO-, R ^11CZ6 and R ^14CZ6 are, It is the same group ^and is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of a hydroxy group, -O-, or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M; R ^1CZ6 is a hydrogen atom, and R ^2CZ6 to R ^5CZ6 are each, independently, a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102CZ6 ) ₂ , a nitro group, all of the hydrogen atoms, or A hydrocarbon group having 1 to 10 carbon atoms in which a fluorine atom is partially substituted, -NHCO-R ^102CZ6 , -OR ^102CZ6 , -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M,

R ^102CZ6 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M;

A ^c+ is Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ^{3 +} , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ or Mn ⁴⁺ , and more preferably a compound that is a hydrogen atom or an alkali metal atom, and L ¹ and L ² are the same group, and —CO— or —SO ₂ -, preferably -CO-, R ^11CZ6 and R ^14CZ6 are the same group and consist of a hydroxy group, -O ^- , or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group, R ^1CZ6 is a hydrogen atom, R ^2CZ6 to R ^5CZ6 are each independently a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, halogen atom, -N(R ^102CZ6 ) ₂ , nitro group, trifluoromethyl group, -OR ^102CZ6 , -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M, R ^102CZ6 is a hydrogen atom, or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of, A ^c+ is Mg ²⁺ , Ca ^{2 +} , Sr ²⁺ , Ba ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ or Mn ⁴⁺ , M is a hydrogen atom or an alkali A compound that is a metal atom is more preferred.

As for compound (IZ6), in formula (IZ6-E), L ¹ is -CO- or -SO ₂ -, Preferably it is -CO-, R ^11EZ6 is a hydroxyl group, -O ^- , or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of, R ^1EZ6 is a hydrogen atom, or -SO ₃ ^- ; -CO ₂ ^- , -SO ₃ M and -CO ₂ M hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of, -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M,

R ^2EZ6 to R ^5EZ6 are each, independently, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N(R ^102EZ6 ) ₂ , a nitro group, and 1 carbon atom in which all or part of the hydrogen atom is substituted by a fluorine atom -20 hydrocarbon group, -NHCO-R ^102EZ6 , -OR ^102EZ6 , -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M,

R ^102EZ6 is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M;

R ^6EZ6 and R ^7EZ6 are each independently a hydrogen atom or a substituent selected from the group consisting of -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M having 1 to 20 carbon atoms A hydrocarbon group, -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M,

A ^c+ is Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Cd ²⁺ , Ni ²⁺ , Zn ²⁺ , Cu ²⁺ , Hg ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ^{2 +} , divalent metal cations such as Pb ²⁺ and Mn ²⁺ , trivalent metal cations such as Al ³⁺ , Fe ³⁺ and Cr ³⁺ , and tetravalent metal cations such as Sn ⁴⁺ and Mn ⁴⁺ ,

M is preferably a hydrogen atom or an alkali metal atom,

L ¹ is -CO- or -SO ₂ -, preferably -CO-,

R ^11EZ6 is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of a hydroxy group, -O ^- , or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M;

R ^1EZ6 is a hydrogen atom, and R ^2EZ6 to R ^5EZ6 are each, independently, a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, -N(R ^102EZ6 ) ₂ , a nitro group, all of the hydrogen atoms, or A hydrocarbon group having 1 to 10 carbon atoms in which a fluorine atom is partially substituted, -NHCO-R ^102EZ6 , -OR ^102EZ6 , -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M,

R ^102EZ6 is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M;

R ^6EZ6 and R ^7EZ6 are each independently a hydrogen atom or a substituent selected from the group consisting of -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M having 1 to 10 carbon atoms A hydrocarbon group, A ^c+ is Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ^{2 +} , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn ⁴⁺ or Mn ⁴⁺ , M is more preferably a hydrogen atom or an alkali metal atom, and L ¹ is -CO- or -SO ₂ -, preferably -CO-, R ^11EZ6 has a substituent selected from the group consisting of a hydroxyl group, -O ^- , or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M It is a hydrocarbon group having 1 to 10 carbon atoms which may be present,

R ^1EZ6 is a hydrogen atom, R ^2EZ6 to R ^5EZ6 are each, independently, a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, —N(R ^102EZ6 ) ₂ , a nitro group, a trifluoromethyl group, -OR ^102EZ6 , -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M or -CO ₂ M, R ^102EZ6 is a hydrogen atom, or -SO ₃ ^- , -CO ₂ ^- , -SO ₃ M and -CO ₂ M is a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of M, R ^6EZ6 and R ^7EZ6 are each independently a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, A ^c+ is, Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ or Mn ⁴⁺ , and M A compound which is silver, a hydrogen atom, or an alkali metal atom is more preferable.

The compound represented by Formula IZ6 can be manufactured by making the compound represented by Formula JZ6 and the compound represented by Formula KZ6 react. However, as a compound represented by Formula JZ6, and a compound represented by Formula KZ6, 1 type, or 2 or more types can be used, respectively.

[In formula JZ6, formula KZ6, and formula IZ6, a, b, c, d, D, Z, and A ^c+ have the same meanings as above. ZZ represents -SO ₃ M or -CO ₂ M. M has the same meaning as above. MM represents the compound containing the metal which provided 0 or more and c or less electrons to A ^c+ .

When two or more compounds, D, ZZ, a, MM, and M represented by the formula JZ6 exist, they may be the same or different.]

Examples of the compound represented by the formula KZ6 include inorganic compounds such as chlorides, bromides, iodides, sulfates, nitrates, fluorosulfonates, and phosphates containing metals having 0 or more and c or less electrons to A ^c+ ; Sulfonic acid salts such as methanesulfonate, trifluoromethanesulfonate, and p-toluenesulfonate containing a metal in which 0 or more and c or less electrons are imparted to A ^{c +} ;

carboxylates, such as acetates, citrates, formates, gluconates, lactates, oxalates, and tartrates, containing a metal in which 0 or more and c or less electrons are imparted to A ^{c +} ;

a metal in which 0 or more and c or less electrons are donated to A ^c+ in which an alkoxy group such as a methoxy group, an ethoxy group, or a tert-butoxy group is substituted; a metal in which 0 or more and c or less electrons are given to A ^c+ in which a butyl group, a tert-butyl group, or a phenyl group is substituted;

The metal etc. which gave 0 or more and c or less electrons to A< ^c+ > which the hydroxyl group substituted are mentioned.

The usage-amount of the compound represented by Formula KZ6 is 0.05-20 mol normally with respect to 1 mol of the compound represented by Formula JZ6, 0.06-15 mol is preferable, and 0.1-10 mol is more preferable.

When making the compound represented by Formula JZ6 and the compound represented by Formula KZ6 react, it is preferable that a base coexist. Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine and piperidine, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and the like. and organometallic compounds such as metal alkoxides, butyllithium, tert-butyllithium, and phenyllithium, and inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.

The usage-amount of a base is 0.0001-10 mol normally with respect to 1 mol of the compound represented by Formula JZ6, 0.0001-8 mol is preferable, 0.0001-5 mol is more preferable, 0.0001-4 mol is still more preferable.

The reaction of the compound represented by the formula JZ6 and the compound represented by the formula KZ6 is usually carried out in the presence of a solvent.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents, and sulfoxide solvents. and more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, Chloroform, N,N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide are mentioned, more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol , 1-octanol, acetone, methylene chloride, chloroform, N,N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide, particularly preferably water, acetonitrile, methanol, ethanol and 2 -Propanol is mentioned.

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of compounds represented by Formula JZ6.

The reaction temperature of the compound represented by the formula JZ6 and the compound represented by the formula KZ6 is usually -20 to 200°C, preferably -10 to 100°C, and more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

When the compound represented by the formula IZ6 is a compound represented by the formula IZ6-A, it can be produced in the same manner as described above. Specifically, it can manufacture by making the compound represented by Formula JJZ6 and the compound represented by Formula KZ6 react. However, as a compound represented by Formula JJZ6, and a compound represented by Formula KZ6, 1 type, or 2 or more types can be used, respectively.

[In Formula JJZ6, Formula KZ6, and Formula IZ6-A, A ^c+ , b, c, d, R ^1AZ6 , R ^2AZ6 , R ^3AZ6 , R ^4AZ6 , R ^5AZ6 , R ^AA1Z6 , R ^AA2Z6 , R ^12AZ6 , R ^13AZ6 and the dashed line represents the same meaning as above.

R ^1AAZ6 , R ^2AAZ6 , R ^3AAZ6 , R ^4AAZ6 , R ^5AAZ6 , R ^AAA1Z6 , R ^AAA2Z6 , R ^12AAZ6 and R ^13AAZ6 are, independently of each other, a hydrogen atom, -CO-R ^102AAZ6 , -COO-R ^101AAZ6 , -OCO- R ^102AAZ6 , -OR ^102AAZ6 , -SO ₂ -R ^101AAZ6 , -SO ₂ N(R ^102AAZ6 ) ₂ , -CON(R ^102AAZ6 ) ₂ , -N(R ^102AAZ6 ) ₂ , -NHCO-R ^102AAZ6 , halogen atom, cya A no group, a nitro group, -SO ₃ M, -CO ₂ M, a C1-C40 hydrocarbon group which may have a substituent, or the heterocyclic group which may have a substituent is represented.

R ^2AAZ6 and R ^3AAZ6 , R ^3AAZ6 and R ^4AAZ6 , R ^4AAZ6 and R ^5AZ6 , R ^AAA1Z6 and R ^AAA2Z6 and R ^12AAZ6 and R ^13AAZ6 may be respectively bonded to each other to form a ring.

R ^101AAZ6 represents, independently of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.

R ^102AAZ6 represents, each independently, a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.

M has the same meaning as above. When two or more R ^1AAZ6 , R ^2AAZ6 , R ^3AAZ6 , R ^4AAZ6 , R ^5AAZ6 , R ^AAA1Z6 , R ^AAA2Z6 , R ^12AAZ6 , R ^13AAZ6 , R ^101AAZ6 , R ^102AAZ6 or M exist, they may be the same or different.

R ^1AAZ6 , R ^2AAZ6 , R ^3AAZ6 , R ^4AAZ6 , R ^5AAZ6 , R ^AAA1Z6 , R ^AAA2Z6 , R ^12AAZ6 , R ^13AAZ6 , R ^101AAZ6 and R ^102AAZ6 satisfy at least one of (ji) to (j-iii), and R ^1AAZ6 , R ^2AAZ6 , R ^3AAZ6 , R ^4AAZ6 , R ^5AAZ6 , R ^AAA1Z6 , R ^AAA2Z6 , R ^12AAZ6 , R ^13AAZ6 , R ^101AAZ6 and R ^102AAZ6 have -SO ₃ M or -CO ₂ M More than that.

(ji) at least one of R ^1AAZ6 , R ^2AAZ6 , R ^3AAZ6 , R ^4AAZ6 , R ^5AAZ6 , R ^AAA1Z6 , R ^AAA2Z6 , R ^12AAZ6 and R ^13AAZ6 is —SO ₃ M or —CO ₂ M.

(j-ii) at least one of R ^1AAZ6 , R ^2AAZ6 , R ^3AAZ6 , R ^4AAZ6 , R ^5AAZ6 , R ^AAA1Z6 , R ^AAA2Z6 , R ^12AAZ6 and R ^13AAZ6 is -CO-R ^102AAZ6 , -COO-R ^101AAZ6 , -OCO -R ^102AAZ6 , -OR ^102AAZ6 , -SO ₂ -R ^101AAZ6 , -SO ₂ N(R ^102AAZ6 ) ₂ , -CON(R ^102AAZ6 ) ₂ , -N(R ^102AAZ6 ) ₂ or -NHCO-R ^102AAZ6 , and the R ^101AAZ6 and R ^102AAZ6 are a C1-C40 hydrocarbon group having -SO ₃ ^- or -CO ₂ ^- or a heterocyclic group having -SO ₃ ^- or -CO ₂ ^- . However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

(j-iii) at least one of R ^1AAZ6 , R ^2AAZ6 , R ^3AAZ6 , R ^4AAZ6 , R ^5AAZ6 , R ^AAA1Z6 , R ^AAA2Z6 , R ^12AAZ6 and R ^13AAZ6 has -SO ₃ M or -CO ₂ M having 1 to It is a hydrocarbon group of 40 or a heterocyclic group having -SO ₃ M or -CO ₂ M. However, the said hydrocarbon group or the said heterocyclic group may have substituents other than -SO ₃ ^- and -CO ₂ ^- .

a has the same meaning as in Formula IZ6. When a plurality of as exist, they may be the same or different.]

The compound represented by the formula JJZ6 (hereinafter sometimes referred to as compound JJZ6) is a compound represented by the formula pt1Z6 (hereinafter sometimes referred to as a phthalonitrile compound) by the formula pt2Z6 when R ^1AAZ6 is a hydrogen atom. After reacting with a compound (hereinafter sometimes referred to as an alkoxide compound), a compound represented by the formula pt3Z6 (hereinafter sometimes referred to as compound pt3Z6) and a compound represented by the formula pt4Z6 (hereinafter sometimes referred to as compound pt4Z6) ) can be further reacted in the presence of an acid. Further, when R ^1AAZ6 is other than a hydrogen atom, the compound represented by the formula JJZ6 can be produced by further reacting with a compound represented by the formula pt5Z6 (hereinafter, may be referred to as a compound pt5Z6).

Here, the compounds represented by the formulas pt1Z6, pt1Z6, pt3Z6, pt4Z6, and pt5Z6 may each independently be a single compound or a mixture of other compounds.

[In formula pt1Z6, formula pt1Z6, formula pt3Z6, formula pt4Z6, formula pt5Z6 and formula JJZ6, R ^1AAZ6 , R ^2AAZ6 , R ^3AAZ6 , R ^4AAZ6 , R ^5AAZ6 , R ^AAA1Z6 , R ^AAA2Z6 , R 13A AZ above, R ^AAA2Z6 and R ^13A have the same meaning. R ^50Z6 represents an alkyl group having 1 to 20 carbon atoms. M ^1Z6 represents an alkali metal atom. LG represents a halogen atom, a methanesulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group.]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ^50Z6 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group, and preferably a C1 group. -6 alkyl groups are mentioned.

Examples of the alkali metal atom represented by M ^1Z6 include a lithium atom, a sodium atom and a potassium atom.

The usage-amount of an alkoxide compound is 0.1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 0.2-5 mol, More preferably, it is 0.3-3 mol, More preferably, it is 0.4-2 mol. it's a mall

The usage-amount of compound pt3Z6 is 1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 1-5 mol, More preferably, it is 1-3 mol, More preferably, it is 1-2 mol. am.

The usage-amount of compound pt4Z6 is 1-10 mol normally with respect to 1 mol of phthalonitrile compound, Preferably it is 1-5 mol, More preferably, it is 1-3 mol, More preferably, it is 1-2 mol. am.

Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; and carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic acid These are mentioned, More preferably, acetic acid is mentioned.

The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, still more preferably 1 to 6 moles with respect to 1 mole of the phthalonitrile compound.

The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z6, and the compound pt4Z6 is usually carried out in the presence of a solvent.

Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amide solvents such as N,N-dimethylformaldehyde and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N ,N-dimethylformaldehyde, N-methylpyrrolidone and dimethyl sulfoxide, and more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1- octanol, acetone, methylene chloride, chloroform, N,N-dimethylformaldehyde, N-methylpyrrolidone and dimethylsulfoxide are exemplified, particularly preferably water, acetonitrile, methanol, ethanol and 2-propanol. can be heard

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of phthalonitrile compounds.

Reaction temperature is 0-200 degreeC normally, Preferably it is 0-100 degreeC, More preferably, it is 0-70 degreeC, More preferably, it is 0-50 degreeC. Reaction time is 0.5 to 300 hours normally.

The amount of the compound pt5Z6 to be used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 mole to 1 mole of the compound JJZ6 in which R ^1AAZ6 is a hydrogen atom. 1 to 2 moles.

When the compound pt5Z6 is reacted, it is preferable that a base coexist. Examples of the base include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine and piperidine, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and the like. organometallic compounds such as metal alkoxides, butyllithium, tert-butyllithium and phenyllithium; Inorganic bases, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, are mentioned.

The amount of the base used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, still more preferably 1 to 3 moles with respect to 1 mole of the compound JJZ6 in which R ^1AAZ6 is a hydrogen atom. 2 moles.

The reaction of compound pt5Z6 is usually carried out in the presence of a solvent. A solvent can be selected from the range similar to the above.

The usage-amount of a solvent is 1-1000 mass parts normally with respect to 1 mass part of compound JJZ6 whose R<1> ^AAZ6 is a hydrogen atom. The reaction temperature of the compound pt5Z6 is usually -90 to 200°C, preferably -80 to 100°C, more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

When the compound JJZ6 is a compound having no -SO ₃ M (hereinafter sometimes referred to as compound JJJZ6), -SO ₃ M can be introduced by reacting the compound JJJZ6 with a sulfating agent such as fuming sulfuric acid or chlorosulfonic acid. .

The amount of SO ₃ used in the fuming sulfuric acid is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, still more preferably 5 to 25 moles, with respect to 1 mole of the compound JJJZ6. am.

The amount of sulfuric acid used in the fuming sulfuric acid is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles with respect to 1 mole of the compound JJJZ6. .

The usage-amount of chlorosulfonic acid is 1-500 mol normally with respect to 1 mol of compound JJJZ6, Preferably it is 10-300 mol, More preferably, it is 10-200 mol, More preferably, it is 10-150 mol.

The reaction temperature for sulfonation is usually -20 to 200°C, preferably -10 to 100°C, and more preferably 0 to 50°C. Reaction time is 0.5 to 300 hours normally.

The method for taking out the compound JJZ6 from the reaction mixture is not particularly limited, and can be taken out by various known methods. For example, compound JJZ6 can be taken out by filtering the reaction mixture after completion|finish of reaction. After filtration, the obtained residue may be subjected to column chromatography, recrystallization, or the like. Further, after completion of the reaction, the solvent of the reaction mixture may be distilled off, and then purified by column chromatography.

It is preferable that the coloring composition of this invention contains the said compound Z, at least one of resin (B), and a solvent (E), and contains both the said compound Z, resin (B), and a solvent (E). .

It is preferable that the coloring composition of this invention contains resin (Hereinafter, it may be called resin (B).). The coloring composition may further improve dispersion stability by including resin (B).

<Resin (B)>

The resin (B) is preferably an alkali-soluble resin, and is added to at least one monomer (a) (hereinafter sometimes referred to as “(a)”) selected from the group consisting of unsaturated carboxylic acid and unsaturated carboxylic acid anhydride. It is more preferable that it is a polymer which has a structural unit derived.

The resin (B) is a structural unit derived from a monomer (b) (hereinafter sometimes referred to as “(b)”) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and other structural units. It is preferable that it is a copolymer with a branch.

As another structural unit, the structural unit derived from the monomer (c) copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b). Hereinafter, it may be referred to as "(c)"). , a structural unit having an ethylenically unsaturated bond, and the like.

As (a), For example, unsaturated monocarboxylic acids, such as acrylic acid, methacrylic acid, a crotonic acid, and o-, m-, p-vinyl benzoic 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-cyclohexenedicarboxylic 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 , a bicyclo unsaturated compound containing a carboxyl group, such as 5-carboxymethylbicyclo[2.2.1]hept-2-ene and 5-carboxyethylbicyclo[2.2.1]hept-2-ene; carboxylic acid anhydrides such as anhydrides of the above unsaturated dicarboxylic acids other than fumaric acid and mesaconic acid; Unsaturated mono[(meth)acryloyloxyalkyl] of polyhydric carboxylic acid having more than divalence, such as succinic acid mono[2-(meth)acryloyloxyethyl] and phthalic acid mono[2-(meth)acryloyloxyethyl] esters;

and unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid.

Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferable from the point of copolymerization reactivity and the solubility point to the aqueous alkali solution of resin obtained.

(b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond . (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

As (b), for example, a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b2)”) and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b3)”); and the like.

As (b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(b1-1)”) and an alicyclic unsaturated hydrocarbon and a monomer (b1-2) having a structure in which hydrocarbons are epoxidized (hereinafter sometimes referred to as “(b1-2)”).

As (b1-1), the monomer which has a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of (b1-1) include glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, Vinylbenzylglycidyl ether, α-methylvinylbenzylglycidyl 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 (glycidyl) Oxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene and 2,4,6-tris(glycidyloxymethyl)styrene ) styrene and the like.

As (b1-2), vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, Seroxide (trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxy Cyclohexylmethyl (meth) acrylate (eg, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (eg, Cyclomer (registered) Trademark) M100 (made by Daicel Corporation), the compound represented by a formula (BI), the compound represented by a formula (BII), etc. are mentioned.

[In formulas (BI) and (BII), R ^a and R ^b each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group . X ^a and X ^b each independently represent a single bond, *-R ^c -, *-R ^c -O-, *-R ^c -S- or *-R ^c -NH-. R ^c represents an alkanediyl group having 1 to 6 carbon atoms. * indicates a bond with O.]

As a compound represented by Formula (BI), the compound etc. which are represented by any of Formula (BI-1) - Formula (BI-15) are mentioned, Preferably Formula (BI-1), Formula (BI-3), compounds represented by formulas (BI-5), formula (BI-7), formula (BI-9) and formulas (BI-11) to formula (BI-15) are mentioned, More preferably, formula (BI- 1), the compound represented by a formula (BI-7), a formula (BI-9), and a formula (BI-15) is mentioned.

As a compound represented by Formula (BII), the compound etc. which are represented by any of Formula (BII-1) - Formula (BII-15) are mentioned, Preferably Formula (BII-1), Formula (BII-3), The compound represented by a formula (BII-5), a formula (BII-7), a formula (BII-9), and a formula (BII-11) - a formula (BII-15) is mentioned, More preferably, a formula (BII- 1), the compound represented by a formula (BII-7), a formula (BII-9), and a formula (BII-15) is mentioned.

The compound represented by Formula (BI) and the compound represented by Formula (BII) may be used individually, respectively, or the compound represented by Formula (BI) and the compound represented by Formula (BII) may be used together. When these are used together, the content ratio of the compound represented by Formula (BI) and the compound represented by Formula (BII) is on a molar basis, Preferably it is 5:95-95:5, More preferably, it is 10:90-90: 10, and more preferably 20:80 to 80:20.

As (c), for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, tricyclo [5.2.1.0 ^{2, 6} ] decan-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-8-yl ( meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-9-yl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl ( (meth)acrylic acid esters such as meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (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-hydroxybi Cyclo[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-methyl Bicyclo[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-phenoxy Cycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexylox) bicyclo unsaturated compounds such as cycarbonyl)bicyclo[2.2.1]hept-2-ene; N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutylate, N-succinimidyl dicarbonylimide derivatives such as -6-maleimide caproate, N-succinimidyl-3-maleimide propionate and N-(9-acridinyl)maleimide;

Vinyl group-containing aromatic compounds, such as styrene, (alpha)-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride 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; and the like.

Of these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate, and tricyclo[5.2.1.0 ^2,6 ]decane-9 -yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-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.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth)acryloyl group. A resin having such a structural unit can be obtained by adding a monomer having an ethylenically unsaturated bond to a group capable of reacting with the group of (a) or (b) to a polymer having a structural unit derived from (a) or (b). there is.

As such a structural unit, the structural unit which added glycidyl (meth)acrylate to the (meth)acrylic acid unit, the structural unit which added 2-hydroxyethyl (meth)acrylate to the maleic anhydride unit, and glycidyl The structural unit etc. which added (meth)acrylic acid to the (meth)acrylate unit are mentioned. Moreover, when these structural units have a hydroxyl group, the structural unit which further added carboxylic acid anhydride is also mentioned as a structural unit which has an ethylenically unsaturated bond.

The polymer having the structural unit derived from (a) can be produced, for example, by polymerization of a monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. A polymerization initiator, a solvent, etc. are not specifically limited, What is normally used in the said field|area can be used. Examples of the polymerization initiator include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.) ) are mentioned, and what is necessary is just to melt|dissolve each monomer as a solvent.

In addition, the obtained polymer may use the solution after reaction as it is, may use the concentrated or diluted solution, and may use what was taken out as solid (powder) by methods, such as reprecipitation.

If necessary, a catalyst for the reaction of carboxylic acid or carboxylic acid anhydride with a cyclic ether (eg, tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (eg, hydroquinone, etc.) may be used.

Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6 -tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. are mentioned.

Specifically as resin (B), 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acryl rate / (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-cyclohexylmaleimide 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/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl(meth)acrylate/(meth)acrylic acid/2-ethylhexyl(meth)acryl Late 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)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer, benzyl(meth)acrylate/(meth)acrylic acid copolymer, styrene/ (meth)acrylic acid copolymer and the resin of each publication of Unexamined-Japanese-Patent No. 9-106071, Unexamined-Japanese-Patent No. 2004-29518, and Unexamined-Japanese-Patent No. 2004-361455, etc. are mentioned.

Especially, as resin (B), the copolymer containing the structural unit derived from (a) and the structural unit derived from (b) is preferable.

Resin (B) may combine 2 or more types, and in this case, resin (B) is at least 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/vinyltoluene copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl ( It is preferable to include at least one selected from meth)acrylate/(meth)acrylic acid/2-ethylhexyl (meth)acrylate copolymer.

Preferably the weight average molecular weight (Mw) of polystyrene conversion of resin (B) is 3,000-100,000, More preferably, it is 5,000-50,000, More preferably, it is 5,000-30,000. The degree of dispersion [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

The acid value (in terms of solid content) of the resin (B) is preferably 10 to 300 mg-KOH/g, more preferably 20 to 250 mg-KOH/g, still more preferably 30 to 200 mg-KOH/g is g. Here, an acid value is a value measured as the quantity (mg) of potassium hydroxide required in order to neutralize 1 g of resin (B), For example, it can obtain|require by titrating using potassium hydroxide aqueous solution.

To [ the content rate of resin (B) ] in a coloring composition, Preferably it is 3-99 mass % with respect to the total amount of solid content, More preferably, it is 5-99 mass %, More preferably, it is 7-95 mass %.

It is preferable that the epigenetic composition of the present invention contains a solvent (hereinafter, sometimes referred to as a solvent (E).). When the epigenetic composition contains the solvent (E), dispersion stability may be further improved in some cases.

<Solvent (E)>

The solvent (E) is, for example, an ester solvent (a solvent containing -COO- in the molecule and not containing -O-), an ether solvent (containing -O- in the molecule and not containing -COO-). solvent), ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing -COO- in the molecule) solvents containing OH but not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, 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.

As the ether solvent, 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, propylene glycol monoethyl ether, propylene 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 ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol and methylanisole 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, and methyl 3-ethoxypropionate. , 3-ethoxypropionate ethyl, 2-methoxypropionate methyl, 2-methoxypropionate ethyl, 2-methoxypropionate propyl, 2-ethoxypropionate methyl, 2-ethoxypropionate ethyl, 2-methoxy-2- Methyl methyl propionate, 2-ethoxy-2-methyl ethyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono and propyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

As the ketone solvent, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclo pentanone, cyclohexanone, isophorone, and the like.

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

Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene and mesitylene.

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

These solvents may use 2 or more types together.

To [ the content rate of a solvent (E) / the total amount of a coloring composition, Preferably it is 40-99 mass %, More preferably, it is 50-95 mass %.

The coloring composition of this invention WHEREIN: It is preferable that the compound Z is disperse|distributed to the solvent (E).

Compound Z is, if necessary, rosin treatment, surface treatment using a derivative into which an acidic group or basic group is introduced, graft treatment to the compound Z surface with a high molecular compound, etc., atomization treatment by sulfuric acid atomization method, etc., to remove impurities Washing treatment with an organic solvent, water, etc., removal treatment by an ion exchange method of ionic impurities, etc. may be performed. It is preferable that the particle diameter of compound Z is substantially uniform. Compound Z can be made into a state in which the compound Z is uniformly disperse|distributed in a dispersion liquid by making it contain a dispersing agent and performing a dispersion process.

Surfactants etc. are mentioned as a dispersing agent, Any surfactant of cationic, anionic, nonionic, and amphoteric type may be sufficient. Specific examples thereof include surfactants such as polyester, polyamine, and acrylic. You may use these dispersing agents individually or in combination of 2 or more types. As a dispersing agent, if it shows by a brand name, KP (made by Shin-Etsu Chemical Co., Ltd.), Florene (made by Kyoeisha Chemical Co., Ltd.), Solsperse (trademark) (made by Zeneca Co., Ltd.), EFKA (trademark) (manufactured by BASF Co., Ltd.), Azispa (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by Big Chemi Co., Ltd.), BYK (registered trademark) (manufactured by Big Chemi Co., Ltd.) ) and the like.

When using a dispersing agent, the usage-amount of a dispersing agent (solid content) becomes like this with respect to 100 mass parts of compound Z, Preferably it is 300 mass parts or less, More preferably, they are 5 mass parts or more and 100 mass parts or less. When the usage-amount of a dispersing agent exists in the said range, there exists a tendency for the coloring composition of a more uniform dispersed state to be obtained.

The content rate of the compound Z in a coloring composition is 0.1-60 mass % normally in the total amount of a coloring composition, Preferably it is 0.5-50 mass %, More preferably, it is 1-40 mass %.

In a coloring composition, the content rate of compound Z is 1 mass % or more and 90 mass % or less normally with respect to the total amount of solid content, Preferably they are 1 mass % or more and 80 mass % or less, More preferably, they are 2 mass % or more and 75 mass %. % or less.

When the coloring composition of the present invention comprises compound Z, the coloring composition further comprises a colorant other than compound Z (i.e., the aforementioned colorant A1Z1, colorant A1Z2, colorant A1Z3, colorant A1Z4, colorant A1Z5, colorant A1Z6, etc.) may be doing The colorant A1Z1, the colorant A1Z2, the colorant A1Z3, the colorant A1Z4, the colorant A1Z5, and the colorant A1Z6 are hereinafter sometimes referred to as "colorant ZZ". The coloring agent ZZ may contain 1 type, or 2 or more types of coloring agents. It is preferable that the coloring agent ZZ contains a yellow coloring agent or a green coloring agent.

<Colorant ZZ>

The coloring agent ZZ may be a dye or a pigment may be sufficient as it. As the dye, a known dye can be used, and the dye described in the Color Index (published by The Society of Dyers and Colorists) and the dyeing note (Shikisensha) is exemplified. Moreover, according to a chemical structure, an azo dye, anthraquinone dye, a triphenylmethane dye, a xanthene dye, a phthalocyanine dye, etc. are mentioned. These dyes may be used individually or in combination of 2 or more types.

Specifically, the dye of the following color index (C.I.) numbers is mentioned. C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

C.I. Reactive Yellow 2, 76, 116;

C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;

C.I. Disperse Yellow 51, 54, 76;

C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;

C.I. acid orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;

C.I. Reactive Orange 16;

C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

C.I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;

C.I. Acid Red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;

C.I. Acid Violet 34, 102;

C.I. Disperse Violet 26, 27;

C.I. solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

CI Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59:1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111 , 112, 122, 128, 132, 136, 139;

C.I. acid blue 25, 27, 40, 45, 78, 80, 112;

C.I. Direct Blue 40;

C.I. Disperse Blue 1, 14, 56, 60;

C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33;

C.I. acid green 3, 5, 9, 25, 27, 28, 41;

C.I. Basic Green 1;

C.I. Bat Green 1st.

As a pigment, a well-known pigment can be used, For example, the pigment classified as a pigment by the color index (The Society of Dyers and Colorists publication) is mentioned. These can be used individually or in combination of 2 or more types.

Specifically, C.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 , 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214 yellow pigments;

C.I. Orange pigments, such as pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266 , 268, 269, 273 and other red pigments;

C.I. Blue pigments, such as pigment blue 15, 15:3, 15:4, 15:6, 60;

C.I. Violet pigments, such as pigment violet 1, 19, 23, 29, 32, 36, 38;

C.I. Green pigments, such as pigment green 7, 36, 58, 59, are mentioned.

As the colorant ZZ, a yellow dye and a yellow pigment (hereinafter, these may be collectively referred to as a "yellow colorant"), a green dye and a green pigment (hereinafter, these may be collectively referred to as a "green colorant") are preferred, , a yellow pigment and a green pigment are more preferable, and a green pigment is still more preferable.

As a yellow dye, among the said dyes, the dye by which the hue is classified into yellow is mentioned, As a yellow pigment, the pigment by which the hue is classified as yellow among the said pigments is mentioned.

Among the yellow pigments, quinophthalone yellow pigments, metal-containing yellow pigments, and isoindoline yellow pigments are preferable, and C.I. Pigment Yellow 129, 138, 139, 150, and 185 are more preferable, and C.I. Pigment Yellow 138, 139, 150 and 185 are more preferable.

As a green dye, among the said dyes, the dye by which the hue is classified into green is mentioned, As a green pigment, the pigment by which the hue is classified into green among the said pigments is mentioned.

Among the green pigments, phthalocyanine pigments are preferable, and at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable, and C.I. At least one selected from the group consisting of Pigment Green 7, 36, 58 and 59 is more preferable.

When the coloring composition of this invention contains the coloring agent ZZ and a solvent (E), after preparing the coloring agent ZZ containing liquid containing the coloring agent ZZ and a solvent (E) beforehand, using the said coloring agent ZZ containing liquid, a coloring composition is prepared You can do it. When the colorant ZZ does not dissolve in the solvent (E), the colorant ZZ-containing liquid can be prepared by dispersing the colorant ZZ in the solvent (E) and mixing them. The coloring agent ZZ containing liquid may contain a part or all of the solvent (E) contained in a coloring composition.

The coloring composition of the present invention is prepared by mixing a compound Z, a resin (B), a colorant ZZ containing liquid containing a colorant ZZ and a solvent (E), or a compound Z, a solvent (E), a colorant ZZ and Prepared by mixing a colorant ZZ containing liquid containing a solvent (E), or prepared by mixing a compound Z, a resin (B) and a solvent (E), and a colorant ZZ containing liquid containing a colorant ZZ and a solvent (E) It is preferable to be

As the above production method, the compound Z and the resin (B) are mixed by a bead mill or the like to prepare a coloring composition, and the obtained coloring composition is a method of mixing a coloring agent ZZ containing liquid containing a coloring agent ZZ and a solvent (E), or , Compound Z and the solvent (E) are mixed by a bead mill or the like to prepare a coloring composition, and the obtained coloring composition is a method of mixing a coloring agent ZZ containing liquid containing the coloring agent ZZ and the solvent (E), or compound Z and , The resin (B) and the solvent (E) are mixed with a bead mill or the like to prepare a coloring composition, and the obtained coloring composition and the coloring agent ZZ containing liquid containing the coloring agent ZZ and the solvent (E) are preferably mixed.

It is preferable that the colorant ZZ is a colorant containing at least one selected from a green colorant and a yellow colorant.

The colorant ZZ is, if necessary, rosin treatment, surface treatment using a colorant derivative into which an acidic group or basic group is introduced, graft treatment on the colorant ZZ surface with a high molecular compound, etc., atomization treatment by sulfuric acid atomization method, etc., remove impurities Washing treatment with an organic solvent, water, etc., removal treatment by an ion exchange method, etc. of an ionic impurity, etc. may be implemented. It is preferable that the particle diameter of the coloring agent ZZ is substantially uniform. The coloring agent ZZ can be made into the state in which the coloring agent ZZ was uniformly disperse|distributed in the coloring agent ZZ containing liquid by making it contain a dispersing agent and performing a dispersion process. Coloring agent ZZ may carry out a dispersion process independently, respectively, and may mix and disperse|distribute multiple types.

Surfactants etc. are mentioned as a dispersing agent, Any surfactant of cationic type, anionic type, nonionic type, and amphoteric type may be sufficient. Specific examples thereof include surfactants such as polyester, polyamine, and acrylic. You may use these dispersing agents individually or in combination of 2 or more types. As a dispersing agent, if it shows by a brand name, KP (made by Shin-Etsu Chemical Co., Ltd.), Florene (made by Kyoeisha Chemical Co., Ltd.), Solsperse (trademark) (made by Zeneca Co., Ltd.), EFKA (trademark) (manufactured by BASF Co., Ltd.), Azispa (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by Big Chemi Co., Ltd.), BYK (registered trademark) (manufactured by Big Chemi Co., Ltd.) ) and the like.

To prepare the colorant ZZ-containing liquid, when a dispersant is used, the amount of the dispersant (solid content) used is preferably 300 parts by mass or less, more preferably 5 parts by mass or more and 100 parts by mass of the colorant ZZ 100 parts by mass. It is less than a mass part. When the usage-amount of the said dispersing agent exists in the said range, there exists a tendency for the colorant ZZ containing liquid in a more uniformly dispersed state to be obtained.

The content rate of the coloring agent ZZ in the coloring agent ZZ containing liquid is 0.1-60 mass % normally in the total amount of the coloring agent ZZ containing liquid, Preferably it is 0.5-50 mass %, More preferably, it is 1-40 mass %.

In the colorant ZZ-containing liquid, the content of the colorant ZZ is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less, more preferably 2% by mass or more with respect to the total amount of solid content. It is 75 mass % or less.

The coloring composition of the present invention contains the resin (B), and after preparing a colorant ZZ-containing liquid containing the colorant ZZ and a solvent in advance, the colorant ZZ-containing liquid is used to prepare the coloring composition of the present invention, the colorant ZZ containing liquid,

A part or all of resin (B) contained in a coloring composition, Preferably a part may be included previously. By including the resin (B) in advance, the dispersion stability of the colorant ZZ-containing liquid can be further improved. Content of resin (B) in coloring agent ZZ containing liquid is 1-500 mass parts with respect to 100 mass parts of coloring agent ZZ, Preferably it is 5-200 mass parts, More preferably, it is 10-100 mass is wealth

In the coloring composition, the content of the colorant ZZZ in which the compound Z and the colorant ZZ are combined is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less, more preferably with respect to the total amount of solid content. is 2 mass % or more and 75 mass % or less.

The content of the compound Z is usually 0.001 mass % or more, preferably 0.003 mass % or more, more preferably 0.005 mass % or more, in the total amount of the colorant ZZZ, and the upper limit is 100 mass % or less, Preferably it is 99.999 mass % or less, more preferably 99.997 mass% or less.

The content of the compound Z is usually 0.001 mass% or more, preferably 40 mass% or more, more preferably 50 mass% or more, still more preferably 60 mass% or more, in the total amount of the yellow colorant, especially Preferably it is 70 mass % or more, An upper limit is 100 mass % or less, Preferably it is 99.999 mass % or less, More preferably, it is 99.997 mass % or less.

When the colorant ZZ is included, the content of the colorant ZZ is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, still more preferably 1 part by mass or more, with respect to 100 parts by mass of the compound Z, Preferably it is 10000 mass parts or less, More preferably, it is 5000 mass parts or less.

The colored curable composition of this invention contains the compound Z, at least one of resin (B), and a solvent (E), and a polymeric compound (C).

<Polymerizable compound (C)>

The polymerizable compound (C) is a compound that can be polymerized with an active radical and/or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenically unsaturated bond, preferably (meta ) is an acrylic acid ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, and 2-hydroxy Ethyl acrylate, N-vinylpyrrolidone, etc., and the above-mentioned monomer (a), monomer (b), and monomer (c) are mentioned.

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, tri Ethylene glycol di(meth)acrylate, the bis(acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, etc. are mentioned.

Especially, it is preferable that a polymeric compound (C) is a polymeric compound which has three or more ethylenically unsaturated bonds. Examples of the polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipenta Erythritol hexa (meth) 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, caprolactone-modified pentaerythritol tetra (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) acrylate, and preferably dipentaerythritol hexa (meth) acrylate. Pentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are mentioned.

The weight average molecular weight of a polymeric compound (C) becomes like this. Preferably it is 150 or more and 2,900 or less, More preferably, they are 250 or more and 1,500 or less.

It is preferable that the content rate of a polymeric compound (C) is 1-65 mass % with respect to the total amount of solid content in a colored curable composition, It is more preferable that it is 3-60 mass %, It is still more preferable that it is 5-55 mass %. desirable.

The colored curable composition of this invention may contain the polymerization initiator (D).

<Polymerization initiator (D)>

The polymerization initiator (D) is not particularly limited as long as it is a compound capable of initiating polymerization by generating an active radical, an acid, etc. under the action of light or heat, and a known polymerization initiator can be used.

As a polymerization initiator (D), an O-acyl oxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound, an acylphosphine oxide compound, etc. are mentioned.

As the O-acyloxime compound, for example, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl) ) Octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4 -Phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine , N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6 -{2-methyl-4-(3,3-dimethyl-2,4-dioxycyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1 -[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine and N-benzoyloxy-1-[9-ethyl-6-( 2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine; and the like. Moreover, as an O-acyl oxime compound, you may use commercial items, such as Irgacure OXE01, OXE02 (above, BASF Corporation make), and N-1919 (made by ADEKA Corporation). Among them, examples of the O-acyloxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl). At least one selected from the group consisting of octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferable , N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferable.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzyl butan-1-one and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one; and the like. As an alkylphenone compound, you may use commercial items, such as Irgacure 369, 907, 379 (above, BASF Co., Ltd. product).

Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1 -one, 1-hydroxycyclohexylphenylketone, oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone and benzyldimethyl Ketal is also included.

As the biimidazole compound, for example, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3- dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Laid-Open No. 6-75372, Japanese Patent Application Laid-Open No. 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 (e.g. For example, see Japanese Patent Application Laid-Open No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.) and a phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group. imidazole compounds (for example, refer to Unexamined-Japanese-Patent No. 7-10913 etc.) etc. are mentioned.

Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 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) To methyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl) tenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2, 4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6 -[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine etc. are mentioned.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

As a polymerization initiator (D), Benzoin compounds, such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; Benzophenone, o-benzoylbenzoate methyl, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone and benzophenone compounds such as 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compound, and the like.

It is preferable to use these in combination with the polymerization initiator auxiliary (D1) (particularly amines) mentioned later.

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

In the total amount of solid content in colored curable composition, the content rate of a polymerization initiator (D) becomes like this. Preferably it is 0.001-40 mass %, More preferably, it is 0.01-30 mass %.

The colored curable composition of this invention may contain the polymerization initiation auxiliary|assistant (D1).

<Polymerization initiator (D1)>

The polymerization initiator auxiliary (D1) is a compound used for accelerating polymerization of a polymerizable compound whose polymerization is initiated by the polymerization initiator, or a sensitizer. When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

Examples of the polymerization initiator (D1) include an amine compound, an alkoxyanthracene compound, a thioxanthone compound, and a carboxylic acid compound.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, and 4-dimethylaminobenzoic acid. 2-ethylhexyl, 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 etc. are mentioned, Preferably 4,4'-bis(diethylamino)benzophenone is mentioned. Moreover, as an amine compound, you may use commercial items, such as EAB-F (made by Hodogaya Chemical Industry Co., Ltd.).

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-dibu thoxyanthracene and 2-ethyl-9,10-dibutoxyanthracene; and the like.

Examples of the thioxanthone compound include 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxy thioxanthone. Oxanthone etc. are mentioned.

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenyl Sulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, etc. are mentioned.

When using these polymerization initiator adjuvant (D1), the content rate becomes like this in the total amount of solid content in colored curable composition, Preferably it is 0.001-30 mass %, More preferably, it is 0.01-20 mass %.

The coloring composition of this invention may also contain a leveling agent (F) and antioxidant further.

<Leveling agent (F)>

As a leveling agent (F), silicone type surfactant, the silicone type surfactant etc. which have a silicone type surfactant, a fluorine type surfactant, and a fluorine atom are mentioned. These may have a polymerizable group in a side chain.

As a silicone type surfactant, the surfactant etc. which have a siloxane bond in a molecule|numerator are mentioned. Specifically, Toray Silicon DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: 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 and TSF4460 (manufactured by Momentive Performance Materials Japan joint venture), etc. can

As a fluorine-type surfactant, the surfactant etc. which have a fluorocarbon chain|strand in a molecule|numerator are mentioned. Specifically, Florad (registered trademark) FC430, copper FC431 (manufactured by Sumitomo Re-M Co., Ltd.), Megapac (registered trademark) F142D, dong F171, dong F172, dong F173, dong F177, dong F183, dong F554, Copper R30, Copper RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, Copper EF303, Copper EF351, Copper EF352 (Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, copper S382, copper SC101, copper SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Research Institute), etc. are mentioned.

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megapac (trademark) R08, Dong BL20, Dong F475, Dong F477, Dong F443 (DIC Co., Ltd. product), etc. are mentioned.

When containing a leveling agent (F), the content rate is 0.0005 mass % or more and 1 mass % or less normally with respect to the total amount of a coloring composition, Preferably they are 0.001 mass % or more and 0.5 mass % or less, More preferably, 0.001 They are mass % or more and 0.2 mass % or less, More preferably, they are 0.002 mass % or more and 0.1 mass % or less, Especially preferably, they are 0.005 mass % or more and 0.1 mass % or less. If the content rate of a leveling agent (F) exists in the said range, the flatness of a color filter can be made favorable.

<Antioxidant>

From a viewpoint of improving the heat resistance and light resistance of a colorant, it is preferable to use antioxidant individually or in combination of 2 or more types. The antioxidant is not particularly limited as long as it is an antioxidant generally used industrially, and phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like can be used.

Examples of the phenolic antioxidant include Irganox 1010 (Irganox 1010: pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], BASF ( Co.), Irganox 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, BASF Co., Ltd.), Irganox 1330 (Irganox 1330:3,3',3",5,5',5"-hexa-tert-butyl-a,a',a"-(mesitylene-2,4,6-triyl)tri-p -Cresol, manufactured by BASF Co., Ltd.), Irganox 3114 (Irganox 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-tri Ajin-2,4,6(1H,3H,5H)-trion, manufactured by BASF Co., Ltd.), Irganox 3790 (Irganox 3790:1,3,5-tris((4-tert-butyl-3- Hydroxy-2,6-xylyl)methyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, manufactured by BASF Corporation), Irganox 1035 ( Irganox 1035: thiodiethylenebis [3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], BASF Co., Ltd. product), Irganox 1135 (Irganox 1135: benzenepropanoic acid) , 3,5-bis(1,1-dimethylethyl)-4-hydroxy, C7-C9 branched alkyl ester, manufactured by BASF Corporation), Irganox 1520L (Irganox 1520L: 4,6-bis(octylthio) Methyl)-o-cresol, manufactured by BASF Corporation), Irganox 3125 (Irganox 3125, manufactured by BASF Corporation), Irganox 565 (Irganox 565: 2,4-bis(n-octylthio)-6 -(4-hydroxy 3',5'-di-tert-butylanilino)-1,3,5-triazine, BASF Co., Ltd. product), adecastab AO-80 (adecastab AO-80) :3,9-bis(2-(3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetra Oxaspiro (5,5)undecane, manufactured by ADEKA Co., Ltd.), Sumilizer BHT (Sumitomo Chemical Co., Ltd.), Sumilizer GA-80 (Sumilizer GA-80, manufactured by Sumitomo Chemical Co., Ltd.), Sumilizer GS (Sumilizer GS, manufactured by Sumitomo Chemical Co., Ltd.), Cyanox 1790 (Cyanox 1790, manufactured by Cytech Co., Ltd.) and vitamins E (manufactured by Eisai Co., Ltd.) and the like.

As said phosphorus antioxidant, Irgafos 168 (Irgafos 168: tris (2,4-di-tert-butylphenyl) phosphite, BASF Co., Ltd. product), Irgafos 12 (Irgafos 12: tris [2-[ [2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphin-6-yl]oxy]ethyl]amine, manufactured by BASF Corporation; Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF Corporation), ADEKA STAB 329K (made by ADEKA Corporation) , ADEKA STAB PEP36 (manufactured by ADEKA Corporation), ADEKA STAB PEP-8 (manufactured by ADEKA Corporation), Sandstab P-EPQ (manufactured by Clariant Corporation), Weston 618 (Weston 618, manufactured by GE Corporation), Weston 619G (Weston 619G, manufactured by GE), Ultranox 626 (Ultranox 626, manufactured by GE) and Sumilizer GP: 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy ]-2,4,8,10-tetra-tert-butyldibenz[d,f][1.3.2]dioxaphospepine) (manufactured by Sumitomo Chemical Co., Ltd.); and the like.

Examples of the sulfur-based antioxidant include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl or distearyl, and polyols such as tetrakis[methylene(3-dodecylthio)propionate]methane and β-alkyl mercaptopropionic acid ester compounds.

<Other ingredients>

The coloring composition of this invention may contain well-known additives in the said technical field, such as a filler, another high molecular compound, an adhesion promoter, an optical stabilizer, and a chain transfer agent, as needed.

As the adhesion promoter, for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropyl Methyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldime Toxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-sulfanylpropyltrimethoxysilane, 3-isocyanatepropyltri Ethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3 -Aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3- aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, etc. are mentioned.

<Color filter>

A color filter can be formed from the coloring composition or coloring curable composition of this invention. As a method of forming a coloring pattern, the photolithographic method, the inkjet method, the printing method, etc. are mentioned, Preferably the photolithographic method is mentioned. The photolithographic method is a method of apply|coating the said colored curable composition to a board|substrate, drying it, forming a colored curable composition layer, exposing the said colored curable composition layer through a photomask, and developing. In the photolithographic method, it is preferable that the colored curable composition contains the polymerization initiator (D). In the photolithography method, the colored coating film which is the hardened|cured material of the said colored curable composition layer can be formed by not using and/or not developing a photomask at the time of exposure. The colored pattern and colored coating film thus formed can be used as the color filter of the present invention.

The film thickness of the color filter to be manufactured is not specifically limited, It can adjust suitably according to the objective, a use, etc., For example, it is 0.1-30 micrometers, Preferably it is 0.1-20 micrometers, More preferably, it is 0.5- 6 μm.

As the substrate, a glass plate, a resin plate, silicon, or a substrate in which an aluminum, silver, silver/copper/palladium alloy thin film or the like is formed is used. On these board|substrates, another color filter layer, a resin layer, a transistor, a circuit, etc. may be formed.

Formation of each color pixel by the photolithographic method can be performed with a well-known or customary apparatus and conditions. For example, it can manufacture as follows.

First, a colored curable composition is apply|coated on a board|substrate, volatile components, such as a solvent, are removed and dried by heat-drying (pre-baking) and/or drying under reduced pressure, and a smooth colored curable composition layer is obtained.

As a coating method, the spin coating method, the slit coating method, the slit-and-spin coating method, etc. are mentioned.

Next, the colored curable composition layer is exposed through a photomask for forming a target colored pattern. It is preferable to use an exposure apparatus such as a mask aligner and a stepper to uniformly irradiate the entire exposure surface with parallel rays and to accurately align the photomask and the substrate on which the colored curable composition layer is formed.

A colored pattern is formed on a board|substrate by making a developing solution contact the colored curable composition layer after exposure and developing. By image development, the unexposed part of a colored curable composition layer melt|dissolves in a developing solution, and is removed.

As a developing solution, the aqueous solution of alkaline compounds, such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, and tetramethylammonium hydroxide, is preferable, for example.

The developing method may be any, such as a paddle method, a dipping method, and a spray method. In addition, you may incline a board|substrate at an arbitrary angle at the time of development.

It is preferable that the board|substrate after image development is washed with water.

Moreover, it is preferable to post-baking to the obtained coloring pattern.

The said color filter is useful as a color filter used for a display device (liquid crystal display device, organic electroluminescent device, electronic paper, etc.) and a solid-state image sensor, Especially as a color filter used for a liquid crystal display device.

[Example]

Hereinafter, unless otherwise indicated, "part" means "part by mass" and "%" means "mass %".

In the following synthesis examples, the structure of the compound is determined by NMR (JMM-ECA-500; manufactured by Nippon Electronics Co., Ltd.) or mass spectrometry (LC; Agilent type 1200), MASS; Agilent product LC/MSD type 6130 ) was confirmed by

The measurement of the polystyrene conversion weight average molecular weight (Mw) and number average molecular weight (Mn) of resin was performed by GPC method on the following conditions.

Device: HLC-8120GPC (manufactured by Toso Corporation)

Column: TSK-GELG2000HXL

Column temperature: 40°C

Solvent: tetrahydrofuran

Flow rate: 1.0 mL/min

Solid content concentration of analysis sample: 0.001 to 0.01 mass %

Injection volume: 50 μL

Detector: RI

Standard materials for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Toso Corporation)

Ratio (Mw/Mn) of the polystyrene conversion weight average molecular weight (Mw) and number average molecular weight (Mn) obtained above was made into the dispersion degree.

[Example Z1]

Example 1Z1

36.2 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 526 parts of methanol were mixed. A mixture of 20.9 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 10 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C over 1 hour.

The obtained mixture was stirred under 5 degreeC for 4 hours.

13.1 parts of acetic acid and 23.7 parts of ethyl cyanoacetate (made by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture, maintaining at 5 degrees C or less.

The resulting mixture was stirred at 5°C for 1 hour, and then stirred at room temperature for 3 days.

To the obtained mixture were added 2.37 parts of ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 231 parts of methanol, followed by stirring at room temperature for 1 day.

To the obtained mixture were added 0.496 parts of ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 26 parts of methanol, followed by stirring at 40°C for 2 hours and 30 minutes.

17.1 parts of acetic acid, 26.9 parts of barbituric acid, and 793 parts of water were added to the obtained mixture, and it stirred under 40 degreeC for 2 hours.

To the obtained mixture were added 17.0 parts of acetic acid, 26.9 parts of barbituric acid, 12 parts of methanol, and 12 parts of water, followed by stirring at 40°C for 30 minutes, followed by stirring at room temperature for 2 days.

The obtained mixture was filtered, and the residue was washed once with 915 parts of 50% aqueous methanol solution, once with 950 parts of 50% aqueous methanol solution, once with 1600 parts of 50% aqueous methanol solution, and once with 1800 parts of water.

The obtained residue was recrystallized using N,N- dimethylformamide, and 30.7 parts of mixtures of the compound represented by Formula (IZ1-38) and the compound represented by Formula (IZ1-39) were obtained.

<Identification of compound represented by formula (IZ1-38)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 384

Exact Mass: 383

<Identification of compound represented by formula IZ1-39>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 398

Exact Mass: 397

Example 2Z1

In the same manner as in Example 1Z1, except that 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), A mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) was obtained.

<Identification of compound represented by formula IZ1-20>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 395

Exact Mass: 394

<Identification of the compound represented by the formula IZ1-21>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 409

Exact Mass: 408

Example 3Z1

In the same manner as in Example 1Z1, except that 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), formula (IZ1-2) ) to obtain a mixture of the compound represented by the formula (IZ1-3) and the compound represented by the formula (IZ1-3).

<Identification of the compound represented by formula IZ1-2>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 339

Exact Mass: 338

<Identification of compound represented by formula IZ1-3>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 353

Exact Mass: 352

Example 4Z1

In the same manner as in Example 1Z1, except that ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with methyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), formula (IZ1-38) A compound represented by

<Identification of compound represented by formula IZ1-38>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 384

Exact Mass: 383

Example 5Z1

4-Nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), and ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) ) agent) was replaced with methyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), in the same manner as in Example 1Z1, to obtain a compound represented by the formula IZ1-20.

<Identification of the compound represented by the formula IZ1-20>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 395

Exact Mass: 394

Example 6Z1

4-Nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with cyano Except having replaced with methyl acetate (made by Tokyo Chemical Industry Co., Ltd.), it carried out similarly to Example 1Z1, and obtained the compound represented by Formula (IZ1-2).

<Identification of the compound represented by formula IZ1-2>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 339

Exact Mass: 338

Example 7Z1XXX (tBu)

10.0 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 84 parts of methanol were mixed. A mixture of 8.15 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days.

5.42 parts of acetic acid and 6.14 parts of ethyl cyanoacetate (made by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 65°C for 3 days.

To the obtained mixture, 2.69 parts of acetic acid and 3.07 ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 65°C for 3 days. To the obtained mixture, 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, followed by stirring at 65°C for 9 days.

After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the mixture of the compound represented by Formula IZ1-20 and the compound represented by Formula IZ1-21 was obtained.

<Identification of compound represented by formula IZ1-20>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 395

Exact Mass: 394

<Identification of the compound represented by the formula IZ1-21>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 409

Exact Mass: 408

Example 8Z1XXX (542)

2.57 parts of phthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 24.5 parts of methanol were mixed. To the mixture obtained at room temperature, 2.00 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The obtained mixture was stirred under 43 degreeC for 1 hour and 30 minutes.

To the obtained mixture, 2.53 parts of ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.26 parts of acetic acid, and 54.5 parts of methanol were added, followed by stirring at 40°C for 1 hour and 30 minutes. To the obtained mixture, 2.84 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.63 parts of acetic acid, and 9 parts of methanol were added, followed by stirring at 40°C for 1 hour. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the mixture of the compound represented by Formula IZ1-2 and the compound represented by Formula IZ1-3 was obtained.

<Identification of the compound represented by formula IZ1-2>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 339

Exact Mass: 338

<Identification of compound represented by formula IZ1-3>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 353

Exact Mass: 352

Example 9Z1XXX (NO2)

10.0 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 149 parts of methanol were mixed. 5.86 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining at 2 to 6°C over 20 minutes. The resulting mixture was stirred for 5 hours while maintaining at 5°C or lower. While maintaining the obtained mixture at 5°C or lower, 5.79 parts of acetic acid, 5.72 parts of methyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 74 parts of methanol were added thereto. The resulting mixture was stirred at 65°C for 3 days. To the obtained mixture, 2.88 parts of acetic acid and 2.86 parts of methyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added. The resulting mixture was stirred at 65°C for 3 days. In addition, a total of 140 parts of methanol was added other than methanol described above until this time point. To the obtained mixture, 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ1-38 was obtained.

<Identification of compound represented by formula IZ1-38>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 384

Exact Mass: 383

Example 10Z1XXX (tBu)

10.0 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 84 parts of methanol were mixed. A mixture of 8.15 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days.

5.42 parts of acetic acid and 5.38 parts of methyl cyanoacetate (made by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 65°C for 3 days.

To the obtained mixture, 2.69 parts of acetic acid and 2.69 methyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 65°C for 3 days. In addition, 206 parts of methanol in total other than methanol described above were added up to this time point. To the obtained mixture, 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days.

After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ1-20 was obtained.

<Identification of the compound represented by the formula IZ1-20>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 395

Exact Mass: 394

Example 11Z1XXX (645)

60.0 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 501 parts of methanol were mixed.

46.7 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining at 2°C over 15 minutes. The resulting mixture was stirred for 5 hours while maintaining the temperature at 2°C to 6°C. 556 parts of methanol was added to this liquid mixture, maintaining at 5 degrees C or less. To this mixture, 29.3 parts of acetic acid, 46.5 parts of methyl cyanoacetate, and 22 parts of methanol were added. After stirring this mixture at room temperature for 12 hours, it stirred at 40 degreeC for 3 hours and 20 minutes. This mixture, 3.00 parts of acetic acid, and 4.71 parts of methyl cyanoacetate were mixed, and it stirred under 40 degreeC for 1 hour and 25 minutes. This mixture, 2.98 parts of acetic acid, and 4.71 parts of methyl cyanoacetate were mixed, and it stirred under 40 degreeC for 2 hours. This mixture, 2.96 parts of acetic acid, and 4.70 parts of methyl cyanoacetate were mixed, and it stirred under 40 degreeC for 2 hours. This mixture was mixed with 1.50 parts of acetic acid and 2.40 parts of methyl cyanoacetate.

In addition, 111 parts of methanol in total other than methanol described above were added up to this time point. The obtained mixture was stirred under 40 degreeC for 1 hour and 40 minutes. To the obtained mixture, 38.1 parts of acetic acid and 60.6 parts of barbituric acid were added, and the mixture was stirred at 40°C for 42 hours. Moreover, 66 parts of methanol in total other than methanol described above were added up to this point. The mixture was filtered, and the residue was washed 6 times with 400 parts of methanol. The residue was purified by column chromatography to obtain a compound represented by the formula IZ1-2.

<Identification of the compound represented by the formula IZ1-2>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 339

Exact Mass: 338

Example 12Z1

5.0 parts of 4,5-dichlorophthalonitrile and 62 parts of methanol were mixed. While maintaining this mixture at 5 DEG C or lower, a 25% sodium methoxide methanol solution containing sodium methoxide 0.5 times the number of moles of 5.0 parts of 4,5-dichlorophthalonitrile was added. The mixture was stirred at 5°C or lower for 5 hours. To this mixture, maintaining 5°C or lower, methyl cyanoacetate and 6.1 parts of acetic acid were added 1.5 times the number of moles of 5.0 parts of 4,5-dichlorophthalonitrile.

The mixture was stirred at 65° C. for 3 days. This mixture, 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol, and 562 parts of water were mixed, and it stirred under 65 degreeC for 9 days. After solvent distillation of this mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and 0.297 part of compound represented by Formula (IZ1-258) was obtained.

<Identification of compound represented by formula (IZ1-258)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 407

Exact MASS: 406

Example 13Z1XXX (659)

25.9 parts of phthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 513 parts of methanol were mixed. A mixture of 30.3 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 12 parts of methanol was added dropwise to the obtained mixture while maintaining the temperature at 3°C to 5°C over 10 minutes. The resulting mixture was stirred for 6 hours while maintaining the temperature at 3°C to 5°C. 19.8 parts of acetic acid, 28.5 parts of tert-butyl cyanoacetic acid, and 26 parts of methanol were added to the obtained mixture while maintaining at 3 degreeC - 5 degreeC. The resulting mixture was stirred at room temperature for 2 days, and then stirred at 40°C for 3 hours. 5.09 parts of acetic acid and 7.17 parts of tert-butyl cyanoacetic acid were added to the obtained mixture, and it stirred at 40 degreeC for 4 hours. To the resulting mixture were added 4.95 parts of acetic acid, 7.15 parts of tert-butyl cyanoacetic acid and 38 parts of methanol, followed by stirring at 40°C for 16 hours. 19.9 parts of acetic acid, 25.8 parts of barbituric acid, 209 parts of methanol, and 800 parts of water were added to the obtained mixture, and it stirred under 40 degreeC for 3 hours.

The obtained mixture was filtered to obtain a residue. This residue was purified by column chromatography to obtain a compound represented by the formula (IZ1-5).

<Identification of compound represented by formula (IZ1-5)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 381

Exact Mass: 380

Example 14Z1XXX (661)

15.1 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 284 parts of methanol were mixed. A mixture of 8.81 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 18 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 10 minutes. The resulting mixture was stirred for 4 hours while maintaining at 5°C or lower.

5.55 parts of acetic acid was added to the obtained mixture, maintaining at 5 degrees C or less, and it stirred for 30 minutes. This mixture and 12.3 parts of tert-butyl cyanoacetic acid were mixed, and stirred at 40 degreeC for 14 hours. This mixture was mixed with 0.654 parts of acetic acid and 1.24 parts of tert-butyl cyanoacetic acid, followed by stirring at 40°C for 4 hours. This mixture was mixed with 0.613 parts of acetic acid and 1.23 parts of tert-butyl cyanoacetic acid, followed by stirring at 40°C for 3 hours. This mixture was mixed with 0.647 parts of acetic acid and 1.24 parts of tert-butyl cyanoacetic acid. Moreover, 89 parts of methanol in total other than methanol described above were added up to this point. This mixture was stirred under 40 degreeC for 17 hours. This mixture was mixed with 7.14 parts of acetic acid, 11.3 parts of barbituric acid, and 508 parts of water. Up to this point, in addition to the methanol described above, a total of 117 parts of methanol was added. This mixture was stirred under 40 degreeC for 24 hours. This mixture, 3.65 parts of acetic acid, and 5.61 parts of barbituric acid were mixed, and it stirred at 40 degreeC for 9 hours and at room temperature for 2 days. The mixture was filtered, and the residue was washed 3 times with 1330 parts of 50% aqueous methanol solution. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ1-41).

<Identification of compound represented by formula (IZ1-41)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 426

Exact Mass: 425

Synthesis Example 1

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was flowed into the flask, replaced with a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was put, and the mixture was heated to 80°C while stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-ylacrylic The mixed solution of 289 parts of the mixture of the rate and 125 parts of propylene glycol monomethyl ether acetate was dripped over 5 hours. On the other hand, the mixed solution which melt|dissolved 33 parts of 2, 2- azobis (2, 4- dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was dripped over 6 hours. After completion|finish of dripping, after hold|maintaining at the same temperature for 4 hours, it cooled to room temperature, and obtained the solution of the copolymer (resin B1) of 35.0% of solid content. The weight average molecular weight (Mw) of the obtained resin B1 was 8800, the dispersion degree was 2.1, and the solution acid value was 28 mg-KOH/g.

Synthesis Example 2

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was poured into the flask, replaced with a nitrogen atmosphere, 371 parts of propylene glycol monomethyl ether acetate was put, and the mixture was heated to 85°C while stirring. Then, 54 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-ylacrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-ylacrylic The mixed solution of 225 parts of the mixture of the rate, 81 parts of vinyltoluene (isomer mixture), and 80 parts of propylene glycol monomethyl ether acetate was dripped over 4 hours. On the other hand, a solution in which 30 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) was dissolved in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After completion|finish of dripping of an initiator solution, after hold|maintaining at the same temperature for 4 hours, it cooled to room temperature, and obtained the solution of the copolymer (resin B3) of 37.5% of solid content. The obtained resin B3 had a weight average molecular weight (Mw) of 10600, a dispersion degree of 2.01, and a solution acid value of 43 mg-KOH/g.

Synthesis Example 3

In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was poured and replaced with a nitrogen atmosphere, 350 parts of propylene glycol monomethyl ether acetate were put, and the mixture was heated to 85°C while stirring. Subsequently, 70 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-ylacrylate or/and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decane-9- The mixed solution of 202 parts of mixtures of monoacrylate, 78 parts of vinyltoluene (isomer mixture), and 100 parts of propylene glycol monomethyl ether acetate was dripped over 4 hours. On the other hand, a solution obtained by dissolving 33 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 167 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After completion|finish of dripping of an initiator solution, after hold|maintaining at the same temperature for 4 hours, it cooled to room temperature, and obtained the solution of the copolymer (resin B5) of 38.1% of solid content. The obtained resin B5 had a weight average molecular weight (Mw) of 10400, a dispersion degree of 2.03, and a solution acid value of 53 mg-KOH/g.

Example 101Z1

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z1 containing liquid) in which the pigment was dispersed using a bead mill. separately,

Colorant AZ1: 50 parts of a mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39;

58 parts of dispersant (BYK-LPN 6919; made by Big Chemie Japan);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and a mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was dispersed using a bead mill to obtain a coloring composition. next,

total amount of the obtained pigment dispersion (colorant A1Z1 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 1Z1.

[Production of Colored Patterns]

After apply|coating colored curable composition 1Z1 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the interval between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 µm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used in an atmospheric atmosphere, an exposure amount of 80 mJ/cm 2 ( 365 nm standard). In addition, as a photomask, the thing in which the line-and-space pattern of 100 micrometers was formed was used. The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, it developed, and it washed with water. The colored pattern was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

[Measurement of phase difference]

After apply|coating colored curable composition 1Z1 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the colored curable composition layer was exposed at an exposure dose (365 nm standard) of 80 mJ/cm 2 in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, it developed, and it washed with water. The colored coating film was obtained by post-baking this colored coating film at 230 degreeC for 30 minute(s).

The film thickness of the obtained colored coating film was measured using DEKTAK3 (made by Nippon Vacuum Technology Co., Ltd.).

The phase difference value at the inclination angle of 45 degrees of this colored coating film was measured using the ellipsometer (M-220 type|mold spectral ellipsometer; Nippon Spectroscopy Co., Ltd. product). Light with a wavelength of 550 nm was used for the phase difference value measurement. The results are shown in Table 8Z1.

Example 102Z1

The mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with a mixture of the compound represented by the formula IZ1-20 obtained in Example 2Z1 and the compound represented by the formula IZ1-21 was carried out similarly to Example 101Z1, obtained colored curable composition 2Z1, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 103Z1

The mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with a mixture of the compound represented by the formula IZ1-2 obtained in Example 3Z1 and the compound represented by the formula 1Z1-3 was carried out similarly to Example 101Z1, obtained colored curable composition 3Z1, and the colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 104Z1

In the same manner as in Example 101Z1, except that the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-38 obtained in Example 4Z1, Colored curable composition 4Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 105Z1

In the same manner as in Example 101Z1, except that the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-20 obtained in Example 5Z1, Colored curable composition 5Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 106Z1

In the same manner as in Example 101Z1, except that the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-2 obtained in Example 6Z1, Colored curable composition 6Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 107Z1

C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z1, the colored curable composition 7Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 108Z1

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 7, a mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-20 obtained in Example 2Z1 and the compound represented by the formula IZ1-21 Except replacing with the mixture of compounds, it carried out similarly to Example 101Z1, the colored curable composition 8Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 109Z1

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 7, a mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-2 obtained in Example 3Z1 and the compound represented by the formula IZ1-3 Except replacing with the mixture of compounds, it carried out similarly to Example 101Z1, the colored curable composition 9Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 110Z1

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 7, the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-38 obtained in Example 4Z1, It carried out similarly to Example 101Z1, the colored curable composition 10Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 111Z1

C.I. Pigment Green 58 C.I. Substitute with Pigment Green 7, the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-20 obtained in Example 5Z1, It carried out similarly to Example 101Z1, the colored curable composition 11Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 112Z1

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 7, the mixture of the compound represented by Formula IZ1-38 obtained in Example 1Z1 and the compound represented by Formula IZ1-39 was replaced with the compound represented by Formula IZ1-2 obtained in Example 6Z1, It carried out similarly to Example 101Z1, the colored curable composition 12Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 113Z1

C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z1, the colored curable composition 13Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 114Z1

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, a mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-20 obtained in Example 2Z1 and the compound represented by the formula IZ1-21 Except replacing with the mixture of compounds, it carried out similarly to Example 101Z1, the colored curable composition 14Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 115Z1

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, a mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-2 obtained in Example 3Z1 and the compound represented by the formula IZ1-3 Except replacing with the mixture of compounds, it carried out similarly to Example 101Z1, the colored curable composition 15Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 116Z1

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-38 obtained in Example 4Z1, It carried out similarly to Example 101Z1, the colored curable composition 16Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 117Z1

C.I. Pigment Green 58 C.I. Substitute with Pigment Green 59, the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-20 obtained in Example 5Z1, It carried out similarly to Example 101Z1, the colored curable composition 17Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Example 118Z1

C.I. Pigment Green 58 C.I. Substitute with Pigment Green 59, the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the compound represented by the formula IZ1-2 obtained in Example 6Z1, It carried out similarly to Example 101Z1, the colored curable composition 18Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Comparative Example 1Z1

A mixture of the compound represented by the formula IZ1-38 and the compound represented by the formula IZ1-39 obtained in Example 1Z1 was prepared by C.I. Except having replaced it with Pigment Yellow 185, it carried out similarly to Example 101Z1, the colored curable composition C1Z1 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Comparative Example 2Z1

C.I. Pigment Green 58 C.I. Instead of Pigment Green 7, the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was C.I. Except replacing with Pigment Yellow 185, it carried out similarly to Example 101Z1, obtained colored curable composition C2Z1, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

Comparative Example 3Z1

C.I. Pigment Green 58 C.I. It was replaced with Pigment Green 59, and the mixture of the compound represented by the formula IZ1-38 and the compound represented by the formula IZ1-39 obtained in Example 1Z1 was C.I. Except replacing with Pigment Yellow 185, it carried out similarly to Example 101Z1, obtained colored curable composition C3Z1, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z1.

[Table 8Z1]

Example 119Z1

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion liquid (colorant A1Z1 containing liquid) in which the pigment was dispersed using a bead mill.

Separately, colorant AZ1: 50 parts of a mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39;

58 parts of dispersant solution (60% solids);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and a mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was dispersed using a bead mill to obtain a coloring composition.

next,

total amount of the obtained pigment dispersion (colorant A1Z1 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 19Z1.

It replaced with colored curable composition 1Z1, and except having used colored curable composition 19Z1, it carried out similarly to Example 101Z1, and produced the coloring pattern. Moreover, it replaced with colored curable composition 1Z1, and except having used colored curable composition 19Z1, it carried out similarly to Example 101Z1, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z1.

Example 120Z1 to Example 127Z1

Coloring was carried out in the same manner as in Example 119Z1, except that the mixture of the compound represented by the formula IZ1-38 obtained in Example 1Z1 and the compound represented by the formula IZ1-39 was replaced with the coloring agent shown in the “Colorant” column of Table 9Z1. got a pattern. Furthermore, a colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z1.

Example 128Z1 to Example 136Z1

The mixture of the compound represented by the formula IZ1-38 and the compound represented by the formula IZ1-39 obtained in Example 1Z1 was substituted with the compound shown in the "Colorant" column of Table 9Z1, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 119Z1, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z1.

Example 137Z1 to Example 145Z1

The mixture of the compound represented by the formula IZ1-38 and the compound represented by the formula IZ1-39 obtained in Example 1Z1 was replaced with the compound shown in the "Colorant" column of Table 9Z1, and C.I. Pigment Green 58 was replaced with C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 119Z1, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z1.

[Table 9Z1]

Examination of Example Z1 WHEREIN: From the said result, in the colored coating film formed from the colored curable composition containing the compound of this invention, C.I. It turned out that retardation value became small compared with the colored coating film formed from the colored curable composition containing Pigment Yellow 185.

[Example Z2]

Example 1Z2

5.02 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 22 parts of methanol were mixed. To the obtained mixture, 2.90 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 25°C for 3 hours.

To the obtained mixture, 3.67 parts of ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.83 parts of acetic acid, and 30 parts of methanol were added, and the mixture was stirred at 25°C for 1 hour and 30 minutes.

To the obtained mixture, 3.62 parts of ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.37 parts of acetic acid, and 30 parts of methanol were added, and the mixture was stirred at 63°C for 3 hours.

To the obtained mixture, 3.63 parts of ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.36 parts of acetic acid, and 30 parts of methanol were added, and the mixture was stirred at 63°C for 2 hours.

To the obtained mixture, 3.62 parts of ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 2.40 parts of acetic acid were added, and the mixture was stirred at 63°C for 1 hour, at room temperature for 11 hours, and at 63°C for 6 hours.

After lowering the temperature of the obtained mixture to room temperature, it filtered.

The obtained residue was dried to obtain 10.0 parts of a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149.

<Identification of the compound represented by the formula IaZ2-39>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 383

Exact Mass: 382

<Identification of compound represented by formula IaZ2-38>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 355

Exact Mass: 354

<Identification of compound represented by formula IaZ2-149>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 369

Exact Mass:368

Example 2Z2

In the same manner as in Example 1Z2, except that ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 2-cyanoacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.), the formula IbZ2-125 was obtained. The resulting compound was obtained.

<Identification of compound represented by formula IbZ2-125>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 325

Exact Mass:324

Example 3Z2

A compound represented by the formula IbZ2-126 was obtained in the same manner as in Example 1Z2 except that ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 2-cyano-N-methylacetamide.

<Identification of the compound represented by the formula IbZ2-126>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 353

Exact Mass:352

Example 4Z2

In the same manner as in Example 1Z2, except that ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) , a compound represented by the formula IbZ2-148 was obtained.

<Identification of the compound represented by the formula IbZ2-148>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 381

Exact Mass: 380

Example 5Z2

Implemented in the same manner as in Example 1Z2 except that ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 2-cyano-N,N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) Thus, a compound represented by the formula IbZ2-149 was obtained.

<Identification of compound represented by formula IbZ2-149>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 437

Exact Mass: 436

Example 6Z2

In the same manner as in Example 1Z2, except that ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.), formula IbZ2-128 was obtained. The resulting compound was obtained.

<Identification of compound represented by formula IbZ2-128>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 477

Exact Mass: 476

Example 7Z2XXX (662)

2.55 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 84 parts of methanol were mixed. A mixture of 1.47 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 30 parts of methanol was added, maintaining this mixture at 5°C or lower. The mixture was stirred at 5°C or lower for 5 hours. To this mixture, 2.16 parts of acetic acid, 2.92 parts of 2-cyano-N-methylacetamide, and 21 parts of methanol were added, and the mixture was stirred at 40°C for 3 hours.

To this mixture, 13.5 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 40°C for 12 hours and at 62°C for 9 hours.

To this mixture, 1.50 parts of 2-cyano-N-methylacetamide and 3.05 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) were added, and stirred at 62°C for 5 hours and at 40°C for 17 hours. did. In addition, up to this point, 6 parts of methanol in total other than methanol described above were added. After solvent distillation of this mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IbZ2-126 was obtained.

<Identification of the compound represented by the formula IbZ2-126>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 353

Exact Mass: 352

Example 8Z2

10 parts of 4-nitrophthalonitrile and 80 parts of methanol were mixed.

While maintaining the mixture at 0°C, a 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the moles of 10 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0° C. for 5 hours.

To this mixture, 16 parts of 2-cyanoacetamide and 16 parts of acetic acid at 3.3 times the molar number of 10 parts of 4-nitrophthalonitrile were added, followed by stirring at 60°C for 21 days.

After solvent distillation of this mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IbZ2-125 was obtained.

<Identification of the compound represented by the formula IbZ2-125>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 325

Exact Mass: 324

Example 9Z2

10 parts of 4-nitrophthalonitrile and 80 parts of methanol were mixed.

While maintaining the mixture at 0°C, a 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the moles of 10 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0° C. for 5 hours.

To this mixture, 16 parts of 2-cyano-N,N-dimethylacetamide and 16 parts of acetic acid at 3.3 times the molar number of 10 parts of 4-nitrophthalonitrile were added, followed by stirring at 60°C for 21 days. After solvent distillation of this mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IbZ2-148 was obtained.

<Identification of compound represented by formula IbZ2-148>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 381

Exact Mass: 380

Example 10Z2

10 parts of 4-nitrophthalonitrile and 80 parts of methanol were mixed. While maintaining the mixture at 0°C, a 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the moles of 10 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0° C. for 5 hours. To this mixture, 16 parts of 2-cyano-N,N-diethylacetamide and 16 parts of acetic acid at 3.3 times the molar number of 10 parts of 4-nitrophthalonitrile were added, followed by stirring at 60°C for 21 days.

After solvent distillation of this mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula (IbZ2-149) was obtained.

<Identification of compound represented by formula IbZ2-149>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 437

Exact Mass: 436

Example 11Z2XXX (660)

1.25 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 41 parts of methanol were mixed. A mixture of 0.722 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 19 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 5 minutes. The resulting mixture was stirred for 4 hours while maintaining at 5°C or lower.

While maintaining the obtained mixture at 5°C or lower, 1.21 parts of acetic acid, 2.33 parts of 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 18 parts of methanol were added. The resulting mixture was stirred at 40°C for 21 hours. To the obtained mixture, 0.596 parts of acetic acid, 1.17 parts of 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 17 parts of methanol were added. The resulting mixture was stirred at 40°C for 3 hours. To the obtained mixture, 2.09 parts of acetic acid was added, and the mixture was stirred at 50°C for 2 hours, at 60°C for 2 hours, at room temperature for 15 hours, and at 62°C for 3 hours.

To the obtained mixture, 0.981 parts of trifluoroacetic acid was added, and the mixture was stirred at 62°C for 2 hours.

To the obtained mixture, 11.5 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added, followed by stirring at 62°C for 2 hours, at room temperature for 14 hours, and at 62°C for 5 hours. Furthermore, up to this point, 10 parts of methanol in total other than methanol described above were added. The resulting mixture was cooled to 23°C, and added to 1100 parts of a 50% aqueous acetic acid solution.

To the obtained mixture, 40 parts of methanol and 400 parts of 50% aqueous acetic acid solution were added.

The obtained mixture was filtered, and the obtained residue was washed 6 times with 250 parts of 50% aqueous acetic acid solution and 3 times with 250 parts of water. The obtained residue was dried under reduced pressure at 60°C to obtain 3.32 parts of a compound represented by the formula IbZ2-128.

<Identification of compound represented by formula IbZ2-128>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 477

Exact Mass: 476

Example 12Z2XXX (653)

25.2 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 212 parts of methanol were mixed. A mixture of 20.5 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days.

13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 10 to 20°C for 5 hours, and then stirred at 40°C for 16 hours. To the obtained mixture, 6.79 parts of acetic acid and 6.75 parts of 2-cyano-N-methylacetamide were added, and the mixture was stirred at 40°C for 6 hours and at 50°C for 65 hours. In addition, 201 parts of methanol in total other than methanol described above were added up to this point. To the obtained mixture, 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 604 parts of water were added, and the mixture was stirred at 40°C for 53 hours.

The resulting mixture was filtered, and the residue was washed with a 50% aqueous methanol solution. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ2-64).

<Identification of the compound represented by the formula IbZ2-64>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 364

Exact Mass: 363

Example 13Z2XXX (659)

25.9 parts of phthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 513 parts of methanol were mixed. A mixture of 30.3 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 12 parts of methanol was added dropwise to the obtained mixture while maintaining the temperature at 3°C to 5°C over 10 minutes. The resulting mixture was stirred for 6 hours while maintaining the temperature at 3°C to 5°C.

19.8 parts of acetic acid, 28.5 parts of tert-butyl cyanoacetic acid, and 26 parts of methanol were added to the obtained mixture while maintaining at 3 degreeC - 5 degreeC. The resulting mixture was stirred at room temperature for 2 days, and then stirred at 40°C for 3 hours. 5.09 parts of acetic acid and 7.17 parts of tert-butyl cyanoacetic acid were added to the obtained mixture, and it stirred at 40 degreeC for 4 hours.

To the resulting mixture were added 4.95 parts of acetic acid, 7.15 parts of tert-butyl cyanoacetic acid, and 38 parts of methanol, followed by stirring at 40°C for 16 hours. 19.9 parts of acetic acid, 25.8 parts of barbituric acid, 209 parts of methanol, and 800 parts of water were added to the obtained mixture, and it stirred under 40 degreeC for 3 hours. The resulting mixture was filtered to obtain a residue. The residue was purified by column chromatography to obtain a compound represented by the formula (IaZ2-5).

<Identification of compound represented by formula (IaZ2-5)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 394

Exact Mass: 393

Example 14Z2XXX (661)

15.1 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 284 parts of methanol were mixed. A mixture of 8.81 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 18 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 10 minutes. The resulting mixture was stirred for 4 hours while maintaining at 5°C or lower. 5.55 parts of acetic acid was added to the obtained mixture, maintaining at 5 degrees C or less, and it stirred for 30 minutes. This mixture and 12.3 parts of tert-butyl cyanoacetate were mixed, and the mixture was stirred at 40°C for 14 hours.

This mixture was mixed with 0.654 parts of acetic acid and 1.24 parts of tert-butyl cyanoacetic acid, followed by stirring at 40°C for 4 hours. This mixture was mixed with 0.613 parts of acetic acid and 1.23 parts of tert-butyl cyanoacetic acid, followed by stirring at 40°C for 3 hours. This mixture was mixed with 0.647 parts of acetic acid and 1.24 parts of tert-butyl cyanoacetic acid. In addition, 89 parts of methanol in total other than methanol described above were added up to this time point. This mixture was stirred under 40 degreeC for 17 hours. This mixture was mixed with 7.14 parts of acetic acid, 11.3 parts of barbituric acid, and 508 parts of water. In addition, 117 parts of methanol in total other than methanol described above were added up to this time point. This mixture was stirred under 40 degreeC for 24 hours. This mixture, 3.65 parts of acetic acid, and 5.61 parts of barbituric acid were mixed, and it stirred at 40 degreeC for 9 hours and at room temperature for 2 days. This mixture was filtered, and the residue was wash|cleaned 3 times with 1330 parts of 50% methanol aqueous solution. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IaZ1-41).

<Identification of compound represented by formula (IaZ1-41)>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 439

Exact Mass: 438

Example 15Z2XXX (520)

5.41 parts of 3,4,5,6-tetrafluorophthalonitrile and 23.6 parts of methanol were mixed. A mixture of 2.70 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 10 parts of methanol was added to this mixture under 20°C to 25°C.

The mixture was stirred at 20°C to 25°C for 4 hours and 20 minutes. To this mixture, 3.36 parts of acetic acid, 5.99 parts of methyl cyanoacetate, and 7.5 parts of methanol were added. The mixture was stirred at 63° C. for 2 hours. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula (IaZ2-223) was obtained.

<Identification of compound represented by formula (IaZ2-223)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 382

Exact Mass: 381

Example 16Z2XXX (538)

2.52 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 22.8 parts of methanol were mixed. At room temperature, 1.98 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added to this mixture. The mixture was stirred at 38°C for 3 hours.

To this mixture, 2.79 parts of cyanoacetylurea (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1.26 parts of acetic acid were added. The mixture was stirred at 40°C for 1 hour and 30 minutes.

To this mixture, 2.77 parts of cyanoacetylurea (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1.61 parts of acetic acid were added. In addition, 39.2 parts of methanol in total other than methanol described above were added up to this point. This mixture was stirred under 40 degreeC for 1 hour. 65.2 parts of water was added to this mixture, and it stirred under 40 degreeC for 2 hours 30 minutes. To this mixture, 2.80 parts of cyanoacetylurea (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1.60 parts of acetic acid were added, and the mixture was stirred at 40°C for 20 hours. Furthermore, up to this point, 31 parts of methanol in total other than methanol described above were added. After solvent distillation of this mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula (IbZ2-19) was obtained.

<Identification of compound represented by formula (IbZ2-19)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 366

Exact Mass: 365

Example 17Z2

8 parts of phthalonitrile and 63 parts of ethanol were mixed.

To this mixture, a 21% sodium ethoxide ethanol solution containing sodium ethoxide in a mole number equal to 1 times the mole number of 8 parts of phthalonitrile was added. The mixture was stirred at room temperature for 2 hours. To this mixture, 25 parts of acetic acid and 8 parts of phthalonitrile were added with the compound represented by the formula (ppp1) of 2.3 times the mole number of moles, and it stirred under 90 degreeC for 64 hours.

The mixture was cooled to room temperature and filtered. The obtained residue was washed with 160 parts of methanol and dried. 24 parts of the obtained residue and 230 parts of N,N-dimethylformamide were mixed.

210 parts of acetic acid were added to this mixture. The mixture was filtered.

The obtained residue was washed with 79 parts of methanol and dried to obtain 17 parts of a compound represented by the formula (IbZ2-311).

<Identification of compound represented by formula (IbZ2-311)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 508

Exact Mass: 507

200 parts of dichloromethane and 150 parts of trifluoroacetic acid were added to 15 parts of the compound represented by Formula (IbZ2-311), and it stirred at room temperature for 50 hours.

160 parts of methanol was added to the obtained mixture, and it filtered.

The obtained residue was dried, and 13 parts of residues were obtained.

After mixing 12 parts of this residue and 230 parts of N,N- dimethylformamide, it stirred for 1 hour, and it filtered. The obtained residue and 160 parts of methanol were mixed, and it stirred under 70 degreeC.

The resulting mixture was filtered. This residue was dried to obtain 9 parts of a compound represented by the formula (IbZ2-317).

<Identification of compound represented by formula (IbZ2-317)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 394

Exact Mass: 395

Example 18Z2

5 parts of 4-nitrophthalonitrile and 39 parts of ethanol were mixed.

While this mixture was maintained at 0°C, a 21% sodium ethoxide ethanol solution containing sodium ethoxide in moles 0.5 times the moles of 5 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0° C. for 3 hours. To this mixture, 16 parts of acetic acid and 5 parts of 4-nitrophthalonitrile were added with a compound represented by the formula (ppp1) in 3.3 times the moles of the moles. The mixture was sealed and stirred at 90°C for 56 hours. The mixture was cooled to room temperature and filtered. This residue was washed with ethanol to obtain 8 parts of a residue A. 10 parts of 4-nitrophthalonitrile and 79 parts of ethanol were mixed. While maintaining the mixture at 0°C, a 21% sodium ethoxide ethanol solution containing sodium ethoxide in moles 0.5 times the moles of 10 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0° C. for 3 hours. To this mixture, 31 parts of acetic acid and 10 parts of 4-nitrophthalonitrile were added with the compound represented by the formula (ppp1) in 3.3 times the number of moles. The mixture was sealed and stirred at 90°C for 56 hours. The mixture was cooled to room temperature and filtered. The obtained residue was washed with ethanol, and 15 parts of residue B was obtained. 4 parts of residue A, 14 parts of residue B, and 170 parts of N,N- dimethylformamide were mixed.

This mixture and 710 parts of methanol were mixed, and it stirred at room temperature for 16 hours.

This mixture was filtered, and 13 parts of residues containing the compound represented by Formula (IbZ2-312) were obtained.

<Identification of compound represented by formula (IbZ2-312)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 553

Exact Mass: 552

13 parts of the residue containing the compound represented by Formula (IbZ2-312), 170 parts of dichloromethane, and 130 parts of trifluoroacetic acid were mixed, and it stirred at room temperature for 16 hours.

After solvent distillation of this mixture, 190 parts of N,N- dimethylformamide was added to 12 parts of the obtained residue, and it filtered, after stirring at 90 degreeC for 10 minutes. The obtained filtrate was left still at room temperature for 16 hours. This filtrate was filtered, and 8.0 parts of residues were obtained. 8.0 parts of this residue and 22 parts of tetrahydrofuran were mixed, and after stirring under 70 degreeC for 3 hours, it filtered.

7.2 parts of the obtained residue and 21 parts of acetic acid were mixed, and after stirring under 80 degreeC for 2 hours, it filtered.

6.2 parts of the obtained residue and 170 parts of toluene were mixed, and after stirring under 95 degreeC for 3 hours, it filtered.

5.6 parts of the obtained residue and 50 parts of water were mixed, and after stirring under 90 degreeC for 16 hours, it filtered.

The obtained residue was dried to obtain 5.4 parts of a compound represented by the formula (IbZ2-515).

<Identification of compound represented by formula (IbZ2-515)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 439

Exact Mass: 440

Example 19Z2

2 parts of phthalonitrile and 16 parts of methanol were mixed.

While maintaining this mixture at 0°C, a 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the number of moles of 2 parts of phthalonitrile was added.

The mixture was stirred at 0° C. for 5 hours. To this mixture, 4.2 parts of acetic acid and the compound represented by Formula (ppp2) of 3.3 times the mole number of moles of 2 parts of phthalonitrile were added, and it stirred under 60 degreeC for 6 days. The mixture was cooled to room temperature and filtered. The obtained residue was washed with methanol to obtain 4 parts of a residue Aa containing a compound represented by the formula (IbZ2-313). 8 parts of phthalonitrile and 63 parts of methanol were mixed. While maintaining the mixture at 0°C, a 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the moles of 8 parts of phthalonitrile was added. The mixture was stirred at 0° C. for 5 hours. To this mixture, 17 parts of acetic acid and the compound represented by Formula (ppp2) of 3.3 times the number of moles of 8 parts of phthalonitrile were added, and it stirred under 60 degreeC for 10 days.

The mixture was cooled to room temperature and filtered. The obtained residue was washed with methanol to obtain 16 parts of a residue Bb containing a compound represented by the formula (IbZ2-313).

<Identification of compound represented by formula (IbZ2-313)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 536

Exact Mass: 535

2 parts of residue Aa containing the compound represented by Formula (IbZ2-313), 27 parts of dichloromethane, and 22 parts of trifluoroacetic acid were mixed, and it stirred at room temperature for 16 hours. The solvent was distilled off this mixture to obtain 2 parts of a residue Aaa. 2 parts of the residue Aa containing the compound represented by the formula (IbZ2-313), 16 parts of the residue Bb containing the compound represented by the formula (IbZ2-313), 240 parts of dichloromethane and 190 parts of trifluoroacetic acid are mixed, It stirred for 16 hours.

The solvent was distilled off this mixture, and 16 parts of residue Ccc was obtained.

1.7 parts of residue Aaa, 16 parts of residue Ccc, and 210 parts of acetic acid were mixed, and it stirred at 80 degreeC for 16 hours. The mixture was filtered, and 13 parts of residues were obtained. This residue and 71 parts of diethyl ether were mixed, and it stirred at room temperature for 16 hours. This mixture was filtered, and the obtained residue was dried, and 12 parts of compounds represented by Formula (IbZ2-318) were obtained.

<Identification of compound represented by formula (IbZ2-318)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 422

Exact Mass: 423

Example 20Z2

2 parts of 4-nitrophthalonitrile and 16 parts of methanol were mixed.

While the mixture was maintained at 0°C, a 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the moles of 2 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0° C. for 3 hours. To this mixture, 2.1 parts of acetic acid and the compound represented by the formula (ppp2) of 3.3 times the number of moles of 2 parts of 4-nitrophthalonitrile were added, and the mixture was stirred at 60°C for 15 days. The mixture was cooled to room temperature and filtered. The obtained residue was washed with 48 parts of methanol to obtain 8.4 parts of a residue containing a compound represented by the formula (IbZ2-314).

<Identification of compound represented by formula (IbZ2-314)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 581

Exact Mass: 580

8.4 parts of the residue containing the compound represented by Formula (IbZ2-314), 110 parts of dichloromethane, and 89 parts of trifluoroacetic acid were mixed, and it stirred at room temperature for 16 hours. The solvent was distilled off this mixture, and 6.9 parts of residues were obtained. 6.1 parts of this residue and 34 parts of dimethyl sulfoxide were mixed, and it stirred at room temperature for 5 minutes. This mixture and 190 parts of acetic acid were mixed, and it stirred at room temperature for 30 minutes. This mixture and 290 parts of methanol were mixed, and it stirred at room temperature for 1 hour. The mixture was filtered to obtain 5.7 parts of a residue. 5.6 parts of this residue and 150 parts of water were mixed, and it stirred under 80 degreeC for 2 hours, and filtered.

The obtained residue was dried to obtain 5.4 parts of a compound represented by the formula (IbZ2-516).

<Identification of compound represented by formula (IbZ2-516)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 467

Exact Mass: 468

Example 21Z2

A compound represented by the formula (ppp3) with a mole number of 1.1 times the mole number of 6 parts of phthalonitrile, 66 parts of dimethyl sulfoxide, and tert-butoxypotassium with a mole number equal to 1 times the mole number of 6 parts of phthalonitrile are mixed at room temperature. It stirred for 10 minutes. 6 parts of phthalonitriles were added to this mixture, and it stirred under 80 degreeC for 2 hours. To this mixture, the compound represented by the formula (ppp3) of the number of moles 1.1 times the number of moles of 6 parts of phthalonitrile was added, and the mixture was stirred at 180°C for 2 hours. The mixture was cooled to room temperature, filtered, and 5.3 parts of a residue was obtained. 5.0 parts of this residue, 55 parts of dimethyl sulfoxide, and 47 parts of N,N- dimethylformamide were mixed, and it stirred under 80 degreeC for 30 minutes.

This mixture and 240 parts of methanol were mixed, and it stirred under 80 degreeC for 30 minutes.

The mixture was cooled to room temperature and filtered. The obtained residue, 55 parts of dimethyl sulfoxide and 47 parts of N,N-dimethylformamide were mixed, and it stirred under 80 degreeC for 30 minutes. This mixture and 240 parts of methanol were mixed, and it stirred under 80 degreeC for 30 minutes. The mixture was cooled to room temperature, filtered, and 4.6 parts of a residue was obtained. This residue and methanol were mixed, and it stirred under 80 degreeC for 2 hours. The mixture was filtered, and the obtained residue was dried to obtain 4.5 parts of a compound represented by the formula (IbZ2-319).

<Identification of the compound represented by the formula (IbZ2-319)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 518

Exact Mass: 519

Example 22Z2

50 parts of 4-aminomethylbenzoic acid and 50 parts of 4-aminomethylbenzoic acid, cyanoacetic acid with a mole number of 1.2 times the mole number, and N,N'-dicyclohexylcarboxyimide with a mole number of 0.9 times the mole number of 50 parts of 4-aminomethylbenzoic acid , 890 parts of tetrahydrofuran were mixed, and the mixture was stirred at room temperature for 16 hours. The mixture was filtered, and the filtrate was solvent-distilled to obtain a residue.

The obtained residue and 270 parts of ethyl acetate were mixed, and it filtered.

The obtained residue was dried and 30 parts of compounds represented by Formula (ppp4) were obtained.

<Identification of compound represented by formula (ppp4)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 217

Exact Mass: 218

Separately, 3 parts of phthalonitrile and 110 parts of ethylene glycol were mixed. To this mixture, at room temperature, a 25% sodium methoxide methanol solution containing sodium methoxide at 1.5 times the number of moles of 3 parts of phthalonitrile was added.

The mixture was stirred at room temperature for 4 hours. To this mixture, the compound represented by the formula (ppp4) of the mole number of 3.1 times the mole number of 3 parts of phthalonitrile and 110 parts of ethylene glycol were added, and it stirred under 110 degreeC for 16 hours. After cooling this mixture to room temperature, 630 parts of methanol was added. This mixture and 26 parts of acetic acid were mixed. The mixture was filtered to obtain 11 parts of a residue. This residue and 220 parts of dimethyl sulfoxide were mixed. This mixture and 630 parts of methanol were mixed. The mixture was filtered to obtain 9.5 parts of a residue. This residue and 220 parts of dimethyl sulfoxide were mixed. This mixture and 630 parts of methanol were mixed. The mixture was filtered, and 9 parts of residues were obtained. This residue and 200 parts of water were mixed, and it stirred under 80 degreeC for 2 hours. This mixture was mixed with 2.1 parts of acetic acid. The mixture was filtered to obtain 8.5 parts of a residue. 8.1 parts of this residue and 260 parts of dimethyl sulfoxide were mixed, and it stirred under 60 degreeC for 20 minutes. The mixture was cooled to room temperature, left still at room temperature for 2 hours, and filtered.

The obtained residue was washed with a 2% aqueous acetic acid solution to obtain 6.2 parts of the residue. This residue and 150 parts of water were mixed, and it stirred under 80 degreeC for 30 minutes. The mixture was cooled to room temperature and filtered.

The obtained residue was washed with 200 parts of water. This residue was dried to obtain 6 parts of a compound represented by the formula (IbZ2-320).

<Identification of compound represented by formula (IbZ2-320)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 546

Exact Mass: 547

Example 23Z2

5 parts of 4,5-dibromophthalonitrile and 93 parts of 2-ethoxyethanol were mixed.

To this mixture, a 25% sodium methoxide methanol solution containing sodium methoxide in moles equal to the number of moles of 5 parts of 4,5-dibromophthalonitrile was added. The mixture was stirred at room temperature for 6 hours. To this mixture, the compound represented by the formula (ppp1) of 6 times the mole number of 5 parts of 4,5-dibromophthalonitrile was added, and after stirring at 90°C for 65 hours, the mixture was stirred at 100°C for 10 hours. 300 parts of water and 21 parts of acetic acid were mixed with this mixture. The mixture was filtered, and 10 parts of residues were obtained. 120 parts of methanol and 10 parts of acetic acid were mixed with this residue. This mixture was filtered, and 5.5 parts of residues containing the compound represented by Formula (IbZ2-315) were obtained.

<Identification of compound represented by formula (IbZ2-315)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 664

Exact Mass: 663

5.5 parts of the residue containing the compound represented by Formula (IbZ2-315), 45 parts of trifluoroacetic acid, and 80 parts of dichloromethane were mixed, and it stirred at room temperature for 16 hours. The solvent was distilled off this mixture, and 6 parts of residues were obtained. This residue and 79 parts of methanol were mixed. The mixture was filtered, and 4 parts of residues were obtained.

This residue, 0.24 parts of lithium hydroxide, 36 parts of tetrahydrofuran, and 12 parts of water were mixed, and it stirred at room temperature for 6 hours. From this mixture, tetrahydrofuran was distilled off using an evaporator. To the resulting mixture, water and 1.5N hydrochloric acid were added. The mixture was filtered to obtain 3.5 parts of a residue. This residue and 40 parts of methanol were mixed. The mixture was filtered, and the residue was washed with 13 parts of hexane to obtain 3 parts of the residue. 2.8 parts of this residue and 33 parts of dimethyl sulfoxide were mixed, and it stirred under 70 degreeC for 20 minutes. The mixture was cooled to room temperature and filtered.

After wash|cleaning the obtained residue with 40 parts of methanol, it wash|cleaned with 50 parts of water.

The residue was dried to obtain 1.8 parts of a compound represented by the formula (IbZ2-706).

<Identification of compound represented by formula (IbZ2-706)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 550

Exact Mass: 551

Example 24Z2

13 parts of 4,5-dichlorophthalonitrile and 160 parts of methanol were mixed.

While this mixture was maintained at 0°C, a 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the number of moles of 13 parts of 4,5-dichlorophthalonitrile was added. The mixture was stirred at 0° C. for 5 hours. To this mixture, 16 parts of acetic acid and the compound represented by the formula (ppp1) of 4.4 times the number of moles of 13 parts of 4,5-dichlorophthalonitrile were added, and the mixture was stirred at 75°C for 7 days. To this mixture, 14 parts of acetic acid and 13 parts of 4,5-dichlorophthalonitrile were added to the compound represented by the formula (ppp1) with three times the moles of moles, and the mixture was stirred at 75°C for 11 days.

The mixture was filtered. The obtained residue was wash|cleaned with 320 parts of methanol, and 26 parts of residues were obtained.

13 parts of this residue, 100 parts of methanol, 16 parts of acetic acid, and 26.3 parts of the compound represented by Formula (ppp1) were mixed, and it stirred under 75 degreeC for 48 hours. The mixture was filtered. The obtained residue was washed with 40 parts of methanol to obtain 12 parts of a residue containing a compound represented by the formula (IbZ2-316).

<Identification of compound represented by formula (IbZ2-316)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 576

Exact Mass: 575

12 parts of the residue containing the compound represented by Formula (IbZ2-316), 160 parts of dichloromethane, and 130 parts of trifluoroacetic acid were mixed, and it stirred at room temperature for 16 hours. The mixture was filtered to obtain 6.2 parts of a residue. This residue and 73 parts of acetic acid were mixed, and it stirred under 80 degreeC for 2 hours. The mixture was filtered, and 5.3 parts of residues were obtained. This residue and 60 parts of water were mixed, and it stirred under 80 degreeC for 2 hours. The mixture was filtered, and the obtained residue was dried to obtain 5 parts of a compound represented by the formula (IbZ2-389).

<Identification of compound represented by formula (IbZ2-389)>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 462

Exact Mass: 463

Example 101Z2

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z2 containing liquid) in which the pigment was dispersed using a bead mill.

separately,

Colorant AZ2: 50 parts of a mixture of the compound represented by the formula IaZ2-39 and the compound represented by the formula IaZ2-38 and the compound represented by the formula IaZ2-149 obtained in Example 1Z2;

58 parts of dispersant (BYK-LPN 6919; made by Big Chemie Japan);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and a mixture of the compound represented by the formula IaZ2-39 obtained in Example 1Z2, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was dispersed using a bead mill to obtain a coloring composition.

Then, the total amount of the obtained pigment dispersion liquid (colorant A1Z2 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 1Z2.

[Production of Colored Patterns]

After apply|coating colored curable composition 1Z2 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the interval between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 μm, and using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.), in an atmospheric atmosphere, an exposure amount of 80 mJ/cm 2 ( 365 nm standard). In addition, as a photomask, the thing in which the line-and-space pattern of 100 micrometers was formed was used. The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored pattern was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

[Measurement of phase difference]

After apply|coating colored curable composition 1Z2 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the colored curable composition layer was exposed at an exposure dose (365 nm standard) of 80 mJ/cm 2 in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored coating film was obtained by post-baking this colored curable composition at 230 degreeC for 30 minute(s).

The film thickness of the obtained colored coating film was measured using DEKTAK3 (made by Nippon Vacuum Technology Co., Ltd.). The phase difference value in the inclination angle of 45 degrees of this colored coating film was measured using the ellipsometer (M-220 type|mold spectral ellipsometer; Nippon Spectroscopy Co., Ltd. product). Light with a wavelength of 550 nm was used for the phase difference value measurement. The results are shown in Table 23Z2.

Example 102Z2

The mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was replaced with the compound represented by the formula IbZ2-125 obtained in Example 2Z2, except that It carried out similarly to Example 101Z2, the colored curable composition 2Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 103Z2

Except for replacing the mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 with the compound represented by the formula IbZ2-126 obtained in Example 3Z2, It carried out similarly to Example 101Z2, the colored curable composition 3Z2 was obtained, and the coloring pattern was obtained. Furthermore, a colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 104Z2

The mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was replaced with the compound represented by the formula IbZ2-148 obtained in Example 4Z2, except that It carried out similarly to Example 101Z2, the colored curable composition 4Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 105Z2

The mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was replaced with the compound represented by the formula IbZ2-149 obtained in Example 5Z2, except that It carried out similarly to Example 101Z2, the colored curable composition 5Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 106Z2

The mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was replaced with the compound represented by the formula IbZ2-128 obtained in Example 6Z2, except that It carried out similarly to Example 101Z2, the colored curable composition 6Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 107Z2

C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z2, the colored curable composition 7Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 108Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 7, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was obtained in Example 2Z2 represented by the formula IbZ2-125 Except replacing with the compound, it carried out similarly to Example 101Z2, the colored curable composition 8Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 109Z2

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 7, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was obtained in Example 3Z2 represented by the formula IbZ2-126 Except replacing with a compound, it carried out similarly to Example 101Z2, the colored curable composition 9Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 110Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 7, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was obtained in Example 4Z2 represented by the formula IbZ2-148 Except replacing with a compound, it carried out similarly to Example 101Z2, the colored curable composition 10Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 111Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 7, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was replaced with the formula IbZ2-149 obtained in Example 5Z2 Except replacing with a compound, it carried out similarly to Example 101Z2, the colored curable composition 11Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 112Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 7, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was obtained in Example 6Z2 represented by the formula IbZ2-128 Except replacing with the compound, it carried out similarly to Example 101Z2, the colored curable composition 12Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 113Z2

C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 101Z2, the colored curable composition 13Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 114Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was prepared by the formula IbZ2-125 obtained in Example 2Z2 Except replacing with a compound, it carried out similarly to Example 101Z2, the colored curable composition 14Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 115Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, a mixture of the compound represented by the formula IaZ2-39 obtained in Example 1Z2, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 3Z2 represented by the formula IbZ2-126 Except replacing with a compound, it carried out similarly to Example 101Z2, the colored curable composition 15Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 116Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, a mixture of the compound represented by the formula IaZ2-39 obtained in Example 1Z2, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 4Z2 represented by the formula IbZ2-148 obtained in Example 4Z2 Except replacing with a compound, it carried out similarly to Example 101Z2, the colored curable composition 16Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 117Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was prepared by the formula IbZ2-149 obtained in Example 5Z2 Except replacing with a compound, it carried out similarly to Example 101Z2, the colored curable composition 17Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Example 118Z2

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 59, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was obtained in Example 6Z2 represented by the formula IbZ2-128 Except replacing with a compound, it carried out similarly to Example 101Z2, the colored curable composition 18Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Comparative Example 1Z2

A mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was treated with C.I. Except having replaced with Pigment Yellow 185, it carried out similarly to Example 101Z2, the colored curable composition C1Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Comparative Example 2Z2

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and the mixture of the compound represented by Formula IaZ2-39, the compound represented by Formula IaZ2-38, and the compound represented by Formula IaZ2-149 obtained in Example 1Z2 was C.I. Except replacing it with Pigment Yellow 185, it carried out similarly to Example 101Z2, the colored curable composition C2Z2 was obtained, and the coloring pattern was obtained. Furthermore, a colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

Comparative Example 3Z2

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was treated with C.I. Except replacing it with Pigment Yellow 185, it carried out similarly to Example 101Z2, the colored curable composition C3Z2 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 23Z2.

[Table 23Z2]

Example 119Z2

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z2 containing liquid) in which the pigment was dispersed using a bead mill.

separately,

Colorant AZ2: 50 parts of a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2;

58 parts of dispersant solution (60% solids);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and a mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was dispersed using a bead mill to obtain a coloring composition.

next,

Total amount of the obtained pigment dispersion (colorant A1Z2 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 19Z2.

It replaced with colored curable composition 1Z2, and except having used colored curable composition 19Z2, it carried out similarly to Example 101Z2, and produced the coloring pattern. Moreover, it replaced with colored curable composition 1Z2, and except having used colored curable composition 19Z2, it carried out similarly to Example 101Z2, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 24Z2.

Example 120Z2 to Example 138Z2

Example 1Z2 Except for replacing the mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 with the coloring agent shown in the "Colorant" column of Table 24Z2 It carried out similarly to 119Z2, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 24Z2.

Example 139Z2 to Example 158Z2

The mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was replaced with the compound represented in the "Colorant" column of Table 24Z2, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 119Z2, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 25Z2.

Example 159Z2 to Example 178Z2

The mixture of the compound represented by the formula IaZ2-39, the compound represented by the formula IaZ2-38, and the compound represented by the formula IaZ2-149 obtained in Example 1Z2 was replaced with the compound represented in the "Colorant" column of Table 24Z2, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 119Z2, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 26Z2.

[Table 24Z2]

[Table 25Z2]

[Table 26Z2]

The chemical formula of the compound represented by Formula IaZ2-1 in Table 24Z2, Table 25Z2, and Table 26Z2 is shown.

Examination of Example Z2 WHEREIN: From the said result, in the colored coating film formed from the colored curable composition containing the compound of this invention, C.I. It turned out that retardation value became small compared with the colored coating film formed from the colored curable composition containing Pigment Yellow 185.

[Example Z3]

Example 1Z3

10.3 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 44.8 parts of methanol were mixed. 8.01 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining at 20 to 25°C.

The resulting mixture was stirred at 20°C to 25°C for 2 hours.

10 parts of methanol was added to the obtained mixture while maintaining under 20-25 degreeC.

The obtained mixture was stirred under 20-25 degreeC for 2 hours.

To the obtained mixture, 7.49 parts of 2-cyanoacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.98 parts of acetic acid were added, and the resulting mixture was stirred at 40°C for 2 hours and at 65°C for 2 hours.

To the obtained mixture, 11.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.53 parts of acetic acid and 160 parts of water were added, and the resulting mixture was stirred at 65°C for 3 hours, at room temperature for 2 days, and at 75°C for 5 hours.

At room temperature, 230 parts of methanol was added to the obtained mixture.

The obtained compound was filtered, and the obtained residue was washed once with 170 parts of methanol, twice with 400 parts of methanol, once with 1000 parts of water, and 11 times with 200 parts of methanol.

To the obtained residue, 641 parts of a 5% aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature.

The obtained mixture was filtered, and the obtained residue was wash|cleaned with 1000 parts of water.

478 parts of water was added to the obtained residue, and it stirred at room temperature.

The obtained mixture was filtered, and the obtained residue was wash|cleaned with 500 parts of water.

The obtained residue was dried and 19.1 parts of compounds represented by Formula IZ3-1 were obtained.

<Identification of the compound represented by the formula IZ3-1>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 324

Exact Mass: 323

Example 2Z3

Except for replacing phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), it was carried out in the same manner as in Example 1Z3, and represented by formula IZ3-19 The compound was obtained.

<Identification of the compound represented by the formula IZ3-19>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 369

Exact Mass: 368

Example 3Z3

Formula IZ3-6 in the same manner as in Example 1Z3 except that phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) A compound represented by

<Identification of the compound represented by the formula IZ3-6>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 380

Exact Mass: 379

Example 4Z3XXX (516)

10.3 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 44.8 parts of methanol were mixed.

8.01 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining at 20 to 25°C.

The resulting mixture was stirred at 20°C to 25°C for 2 hours.

10 parts of methanol was added to the obtained mixture while maintaining under 20-25 degreeC.

The obtained mixture was stirred under 20-25 degreeC for 2 hours.

To the obtained mixture, 7.49 parts of 2-cyanoacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.98 parts of acetic acid were added, and the resulting mixture was stirred at 40°C for 2 hours and at 65°C for 2 hours.

To the obtained mixture, 11.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 6.53 parts of acetic acid and 160 parts of water were added, and the resulting mixture was stirred at 65°C for 3 hours, at room temperature for 2 days, and at 75°C for 5 hours.

At room temperature, 230 parts of methanol was added to the obtained mixture.

The obtained compound was filtered, and the obtained residue was washed once with 170 parts of methanol, twice with 400 parts of methanol, once with 1000 parts of water, and 11 times with 200 parts of methanol.

To the obtained residue, 641 parts of 5% aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature.

The obtained mixture was filtered, and the obtained residue was wash|cleaned with 1000 parts of water.

478 parts of water was added to the obtained residue, and it stirred at room temperature.

The obtained mixture was filtered, and the obtained residue was wash|cleaned with 500 parts of water.

The obtained residue was refine|purified by column chromatography, and the compound part represented by Formula IZ3-1 was obtained.

<Identification of the compound represented by the formula IZ3-1>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 324

Exact Mass: 323

Example 5Z3XXX

10.0 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 149 parts of methanol were mixed. 5.86 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining at 2 to 6°C over 20 minutes. The resulting mixture was stirred for 5 hours while maintaining at 5°C or lower. While maintaining the obtained mixture at 5°C or lower, 5.79 parts of acetic acid, 4.86 parts of 2-cyanoacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65°C for 3 days.

To the obtained mixture, 2.88 parts of acetic acid and 2.43 parts of 2-cyanoacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added. The resulting mixture was stirred at 65°C for 3 days. In addition, a total of 140 parts of methanol was added other than methanol described above until this time point. To the obtained mixture, 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days.

After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ3-19 was obtained.

<Identification of the compound represented by the formula IZ3-19>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 369

Exact Mass: 368

Example 6Z3XXX

10.0 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 84 parts of methanol were mixed. A mixture of 8.15 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days.

5.42 parts of acetic acid and 4.56 parts of 2-cyanoacetamide (made by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 65°C for 3 days.

To the obtained mixture, 2.69 parts of acetic acid and 2.28 of 2-cyanoacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 65°C for 3 days. In addition, 206 parts of methanol in total other than methanol described above were added up to this point. To the obtained mixture, 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days.

After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ3-6 was obtained.

<Identification of the compound represented by the formula IZ3-6>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 380

Exact Mass: 379

Example 7Z3

5.0 parts of 4,5-dichlorophthalonitrile and 62 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the moles of 5.0 parts of 4,5-dichlorophthalonitrile was added while maintaining the mixture at 5° C. or lower. The mixture was stirred at 5°C or lower for 5 hours. To this mixture, maintaining 5°C or lower, 2-cyanoacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 6.1 parts of acetic acid were added 1.5 times the number of moles of 5.0 parts of 4,5-dichlorophthalonitrile. The mixture was stirred at 65° C. for 3 days.

This mixture, 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol, and 562 parts of water were mixed, and it stirred under 65 degreeC for 9 days.

After filtering this mixture and distilling off with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula (IZ3-8) was obtained.

<Identification of the compound represented by the formula IZ3-8>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 392

Exact Mass: 391

Example 101Z3

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution;

and solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z3 containing liquid) in which the pigment was dispersed using a bead mill. separately,

Colorant AZ3: 50 parts of a compound represented by the formula IZ3-1 obtained in Example 1Z3;

58 parts of dispersing agent (BYK-LPN6919; Big Chemie Japan Co., Ltd.);

Resin (B): 93 parts of resin B3 solution;

And solvent (E): 800 parts of propylene glycol monomethyl ether acetate were mixed, the compound represented by Formula IZ3-1 obtained in Example 1Z3 was disperse|distributed using the bead mill, and the coloring composition was obtained. next,

Total amount of the obtained pigment dispersion (colorant A1Z3 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 1Z3.

[Production of Colored Patterns]

After apply|coating colored curable composition 1Z3 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the interval between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 μm, and using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.), in an atmospheric atmosphere, an exposure amount of 80 mJ/cm 2 ( 365 nm standard). In addition, as a photomask, the thing in which the line-and-space pattern of 100 micrometers was formed was used. The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored pattern was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

[Measurement of phase difference]

After apply|coating colored curable composition 1Z3 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the colored curable composition layer was exposed at an exposure dose (365 nm standard) of 80 mJ/cm 2 in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored coating film was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

The film thickness of the obtained colored coating film was measured using DEKTAK3 (made by Nippon Vacuum Technology Co., Ltd.). The phase difference value in the inclination angle of 45 degrees of this colored coating film was measured using the ellipsometer (M-220 type|mold spectral ellipsometer; Nippon Spectroscopy Co., Ltd. product). Light with a wavelength of 550 nm was used for the phase difference value measurement. The results are shown in Table 7Z3.

Example 102Z3

A colored curable composition 2Z3 was obtained in the same manner as in Example 101Z3, except that the compound represented by the formula IZ3-1 obtained in Example 1Z3 was replaced with the compound represented by the formula IZ3-19 obtained in Example 2Z3 got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Example 103Z3

A colored curable composition 2Z3 was obtained in the same manner as in Example 101Z3 except that the compound represented by the formula IZ3-1 obtained in Example 1Z3 was replaced with the compound represented by the formula IZ3-6 obtained in Example 3Z3, and a coloring pattern was obtained. got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Example 104Z3

C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z3, obtained colored curable composition 4Z3, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Example 105Z3

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z3, except that the compound represented by the formula IZ3-1 obtained in Example 1Z3 was replaced with the compound represented by the formula IZ3-19 obtained in Example 2Z3, and colored curability Composition 5Z3 was obtained, and a coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Example 106Z3

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z3, except that the compound represented by the formula IZ3-1 obtained in Example 1Z3 was replaced with the compound represented by the formula IZ3-6 obtained in Example 3Z3. Composition 6Z3 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Example 107Z3

C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z3, obtained colored curable composition 7Z3, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Example 108Z3

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 59, and was carried out in the same manner as in Example 101Z3, except that the compound represented by the formula IZ3-1 obtained in Example 1Z3 was replaced with the compound represented by the formula IZ3-19 obtained in Example 2Z3, and colored curability Composition 8Z3 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Example 109Z3

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 59, and was carried out in the same manner as in Example 101Z3, except that the compound represented by the formula IZ3-1 obtained in Example 1Z3 was replaced with the compound represented by the formula IZ3-6 obtained in Example 3Z3. Composition 9Z3 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Comparative Example 1Z3

The compound represented by the formula IZ3-1 obtained in Example 1Z3 was synthesized by C.I. Except replacing with Pigment Yellow 185, it carried out similarly to Example 101Z3, obtained colored curable composition C1Z3, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Comparative Example 2Z3

C.I. Pigment Green 58 C.I. Instead of Pigment Green 7, the compound represented by the formula IZ3-1 obtained in Example 1Z3 was replaced with C.I. Except having replaced with Pigment Yellow 185, it carried out similarly to Example 101Z3, the colored curable composition C2Z3 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

Comparative Example 3Z3

C.I. Pigment Green 58 C.I. Substituted with Pigment Green 59, the compound represented by the formula IZ3-1 obtained in Example 1Z3 was replaced with C.I. Except replacing it with Pigment Yellow 185, it carried out similarly to Example 101Z3, the colored curable composition C3Z3 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z3.

[Table 7Z3]

Example 110Z3

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z3 containing liquid) in which the pigment was dispersed using a bead mill. separately,

Colorant AZ3: 50 parts of a compound represented by the formula IZ3-1;

58 parts of dispersant solution (60% solids);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate were mixed, the compound represented by Formula IZ3-1 was disperse|distributed using the bead mill, and the coloring composition was obtained. next,

Total amount of the obtained pigment dispersion (colorant A1Z3 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 10Z3.

It replaced with colored curable composition 1Z3, and except having used colored curable composition 10Z3, it carried out similarly to Example 101Z3, and produced the coloring pattern. Moreover, it replaced with colored curable composition 1Z3, and except having used colored curable composition 10Z3, it carried out similarly to Example 101Z3, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z3.

Example 111Z1 to Example 111Z3

A coloring pattern was obtained in the same manner as in Example 110Z3 except that the compound represented by Formula IZ3-1 was replaced with the coloring agent shown in the "Colorant" column of Table 8Z3. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z3.

Example 114Z3 to Example 117Z3

The mixture with the compound represented by the formula IZ3-1 was replaced with the compound shown in the "Colorant" column of Table 8Z3, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 110Z3, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z3.

Example 118Z3 to Example 121Z3

The mixture with the compound represented by the formula IZ3-1 was replaced with the compound shown in the "Colorant" column of Table 8Z3, and C.I. Pigment Green 58 was replaced with C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 110Z3, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z3.

[Table 8Z3]

In Example Z3, from the above results, in the colored coating film formed from the colored curable composition containing the compound of the present invention, C.I. It turned out that retardation value became small compared with the colored coating film formed from the colored curable composition containing Pigment Yellow 185.

[Example Z4]

Example 1Z4

20.5 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 171 parts of methanol were mixed. A mixture of 23.9 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 215 parts of methanol was added dropwise to the obtained mixture while maintaining the temperature at 5°C over 1 hour and 20 minutes.

The obtained mixture was stirred under 2 degreeC - 6 degreeC for 7 hours.

To the obtained mixture, 15.6 parts of acetic acid, 17.9 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 118 parts of methanol were added, followed by stirring at 40°C for 15 hours and at 65°C for 7 hours. . To the obtained mixture, 7.82 parts of acetic acid, 8.97 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 80 parts of methanol were added, followed by stirring at 40°C for 17 hours and at 65°C for 4 hours. . To the obtained mixture, 12.6 parts of acetic acid, 14.3 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 104 parts of methanol were added, followed by stirring at 40°C for 16 hours and at 60°C for 9 hours. . To the obtained mixture, 6.32 parts of acetic acid, 7.19 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 40 parts of methanol were added, followed by stirring at 60°C for 3 hours and at room temperature for 59 hours. To the obtained mixture, 15.7 parts of acetic acid, 20.5 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 16 parts of methanol and 744 parts of water were added, and the mixture was stirred at 60°C for 24 hours. The resulting mixture was filtered, and the residue was washed with a 50% aqueous methanol solution. The obtained residue was dried under reduced pressure under 60 degreeC, and 43.1 parts of compounds represented by Formula IZ4-1 were obtained.

<Identification of compound represented by formula IZ4-1>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 352

Exact Mass: 351

Example 2Z4

Except for replacing 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) with 2-cyano-N,N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) , it carried out similarly to Example 1Z4, and obtained the compound represented by Formula IZ4-2.

<Identification of the compound represented by the formula IZ4-2>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 380

Exact Mass: 379

Example 3Z4

Except for replacing phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), it was carried out in the same manner as in Example 1Z4, and represented by formula IZ4-79 The compound was obtained.

<Identification of the compound represented by the formula IZ4-79>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 397

Exact Mass: 396

Example 4Z4

Phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 2-cyano-N,N-dimethylacetamide (Tokyo Chemical Industry Co., Ltd.) ) agent) was replaced with 2-cyano-N,N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.), in the same manner as in Example 1Z4, to prepare a compound represented by formula IZ4-80 got it

<Identification of the compound represented by the formula IZ4-80>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 425

Exact Mass: 424

Example 5Z4

Formula IZ4-40 in the same manner as in Example 1Z4 except that phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) A compound represented by

<Identification of the compound represented by the formula IZ4-40>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 408

Exact Mass: 407

Example 6Z4

Phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 2-cyano-N,N-dimethylacetamide (Tokyo Chemical Industry Co., Ltd.) In the same manner as in Example 1Z4, except that 2-cyano-N,N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with the formula IZ4-41 The resulting compound was obtained.

<Identification of the compound represented by the formula IZ4-41>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 436

Exact Mass: 435

Example 7Z4XXX (651)

20.5 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 171 parts of methanol were mixed.

A mixture of 23.9 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 215 parts of methanol was added dropwise to the obtained mixture while maintaining at 2 to 5°C over 1 hour and 20 minutes. The obtained mixture was stirred under 2-6 degreeC for 7 hours. To the obtained mixture were added 15.6 parts of acetic acid, 17.9 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 46.9 parts of methanol. Moreover, 71 parts of methanol in total were added other than methanol described above up to this time point. The resulting mixture was stirred at 40°C for 15 hours and at 65°C for 7 hours. To the obtained mixture, 7.82 parts of acetic acid, 8.97 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 80 parts of methanol were added, followed by stirring at 40°C for 17 hours and at 65°C for 4 hours. . To the obtained mixture, 12.6 parts of acetic acid, 14.3 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 104 parts of methanol were added, followed by stirring at 40°C for 16 hours and at 60°C for 9 hours. . To the obtained mixture, 6.32 parts of acetic acid, 7.19 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 40 parts of methanol were added, followed by stirring at 60°C for 3 hours and at room temperature for 59 hours. To the obtained mixture, 15.7 parts of acetic acid, 20.5 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 16 parts of methanol and 744 parts of water were added, and the mixture was stirred at 60°C for 9 days.

The resulting mixture was filtered, and the residue was washed with a 50% aqueous methanol solution.

The obtained residue was purified by column chromatography to obtain a compound represented by the formula IZ4-1.

<Identification of compound represented by formula IZ4-1>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 352

Exact Mass: 351

Example 8Z4XXX

10.0 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 83 parts of methanol were mixed.

A mixture of 11.7 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 105 parts of methanol was added dropwise to the obtained mixture while maintaining at 2 to 5°C over 1 hour and 30 minutes. The obtained mixture was stirred under 2-6 degreeC for 7 hours. To the obtained mixture, 7.62 parts of acetic acid, 10.9 parts of 2-cyano-N,N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 140 parts of methanol were added. In addition, up to this point, 35 parts of methanol in total were added other than the methanol described above.

The obtained mixture was stirred under 65 degreeC for 3 days. To the obtained mixture, 3.82 parts of acetic acid and 5.48 parts of 2-cyano-N,N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 65°C for 3 days. To the obtained mixture, 7.65 parts of acetic acid, 10.0 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, it carried out similarly to Example 1Z4, and obtained the compound represented by Formula IZ4-2.

<Identification of the compound represented by the formula IZ4-2>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 380

Exact Mass: 379

Example 9Z4XXX (529)

2.56 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 22 parts of methanol were mixed. 2.96 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added to the obtained mixture while maintaining at 5°C or lower. The resulting mixture was stirred for 3 hours while maintaining at 5°C or lower. While maintaining the obtained mixture at 5°C or lower, 1.84 parts of 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 1.90 parts of acetic acid were added. The resulting mixture was stirred at 40°C for 1 hour and at 65°C for 1 hour. To the obtained mixture, 2.09 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.48 parts of acetic acid, and 41 parts of water were added. In addition, up to this point, 24 parts of methanol in total were added other than the methanol described above. The obtained mixture was stirred under 65 degreeC for 15 hours. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ4-79 was obtained.

<Identification of the compound represented by the formula IZ4-79>

(Mass spectrometry) Ionization mode = ESI + : m/z = [M + H] ⁺ 397

Exact Mass: 396

Example 10Z4XXX

10.0 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 149 parts of methanol were mixed. 5.86 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining at 2 to 6°C over 20 minutes. The resulting mixture was stirred for 5 hours while maintaining at 5°C or lower. While maintaining the obtained mixture at 5°C or lower, 5.79 parts of acetic acid, 8.10 parts of 2-cyano-N,N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65°C for 3 days. To the obtained mixture, 2.88 parts of acetic acid and 4.05 parts of 2-cyano-N,N-diethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added. The resulting mixture was stirred at 65°C for 3 days. In addition, a total of 140 parts of methanol was added other than methanol described above until this time point. To the obtained mixture, 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ4-80 was obtained.

<Identification of the compound represented by the formula IZ4-80>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 425

Exact Mass: 424

Example 11Z4XXX

10.0 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 84 parts of methanol were mixed. A mixture of 8.15 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days. 5.42 parts of acetic acid and 6.09 parts of 2-cyano-N,N- dimethylacetamide (Tokyo Chemical Industry Co., Ltd. product) were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 65°C for 3 days. To the obtained mixture, 2.69 parts of acetic acid and 3.04 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 65°C for 3 days. In addition, 206 parts of methanol in total other than methanol described above were added up to this time point. To the obtained mixture, 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ4-40 was obtained.

<Identification of the compound represented by the formula IZ4-40>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 408

Exact Mass: 407

Example 12Z4XXX

10.0 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 84 parts of methanol were mixed. A mixture of 8.15 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days. 5.42 parts of acetic acid and 7.61 parts of 2-cyano-N,N- dimethylacetamide (Tokyo Chemical Industry Co., Ltd. product) were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 65°C for 3 days. To the obtained mixture, 2.69 parts of acetic acid and 3.80 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 65°C for 3 days. In addition, 206 parts of methanol in total other than methanol described above were added up to this time point. To the obtained mixture, 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ4-41 was obtained.

<Identification of the compound represented by the formula IZ4-41>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 436

Exact Mass: 435

Example 13Z4

5.0 parts of 4,5-dichlorophthalonitrile and 62 parts of methanol were mixed. A 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the moles of 5.0 parts of 4,5-dichlorophthalonitrile was added while maintaining the mixture at 5° C. or lower.

The mixture was stirred at 5°C or lower for 5 hours. To this mixture while maintaining 5°C or lower, 5.0 parts of 4,5-dichlorophthalonitrile 2-cyano-N,N-dimethylacetamide (manufactured by Tokyo Chemical Industry Co., Ltd.) at 1.5 times the mole number of moles and 6.1 parts of acetic acid were added. The mixture was stirred at 65° C. for 3 days. This mixture, 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol, and 562 parts of water were mixed, and it stirred under 65 degreeC for 9 days. After solvent distillation of this mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula (IZ4-321) was obtained.

<Identification of the compound represented by the formula IZ4-321>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 420

Exact Mass: 419

Example 101Z4

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z4 containing liquid) in which the pigment was dispersed using a bead mill.

separately,

Colorant AZ4: 50 parts of a compound represented by the formula IZ4-1 obtained in Example 1Z4,

58 parts of dispersant (BYK-LPN 6919; made by Big Chemie Japan);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and the compound represented by the formula IZ4-1 obtained in Example 1Z4 was dispersed using a bead mill to obtain a coloring composition. next,

total amount of the obtained pigment dispersion (colorant A1Z4 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.); was mixed to obtain colored curable composition 1Z4.

[Production of Colored Patterns]

After apply|coating the colored curable composition 1Z4 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the interval between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 μm, and using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.), in an atmospheric atmosphere, an exposure amount of 80 mJ/cm 2 ( 365 nm standard). In addition, as a photomask, the thing in which the line-and-space pattern of 100 micrometers was formed was used. The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored pattern was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

[Measurement of phase difference]

After apply|coating the colored curable composition 1Z4 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the colored curable composition layer was exposed at an exposure dose (365 nm standard) of 80 mJ/cm 2 in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored coating film was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

The film thickness of the obtained colored coating film was measured using DEKTAK3 (made by Nippon Vacuum Technology Co., Ltd.).

The phase difference value in the inclination angle of 45 degrees of this colored coating film was measured using the ellipsometer (M-220 type|mold spectral ellipsometer; Nippon Spectroscopy Co., Ltd. product). Light with a wavelength of 550 nm was used for the phase difference value measurement. The results are shown in Table 9Z4.

Example 102Z4

A colored curable composition 2Z4 was obtained in the same manner as in Example 101Z4 except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula 1Z4-2 obtained in Example 2Z4 to obtain a colored curable composition 2Z4. got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 103Z4

A colored curable composition 3Z4 was obtained in the same manner as in Example 101Z4 except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula 1Z4-79 obtained in Example 3Z4 to obtain a colored curable composition 3Z4 got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 104Z4

A colored curable composition 4Z4 was obtained in the same manner as in Example 101Z4, except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula 1Z4-80 obtained in Example 4Z4 got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 105Z4

A colored curable composition 5Z4 was obtained in the same manner as in Example 101Z4 except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula 1Z4-40 obtained in Example 5Z4 to obtain a colored curable composition 5Z4 got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 106Z4

A colored curable composition 6Z4 was obtained in the same manner as in Example 101Z4 except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula 1Z4-41 obtained in Example 6Z4, and a coloring pattern was obtained. got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 107Z4

C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 101Z4, the colored curable composition 7Z4 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 108Z4

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z4, except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula IZ4-2 obtained in Example 2Z4, and colored curability Composition 8Z4 was obtained, and a coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 109Z4

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z4, except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula IZ4-79 obtained in Example 3Z4. Composition 9Z4 was obtained, and a coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 110Z4

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z4, except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula IZ4-80 obtained in Example 4Z4, and colored curability Composition 10Z4 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 111Z4

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z4, except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula IZ4-40 obtained in Example 5Z4. Composition 11Z4 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 112Z4

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z4, except that the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula IZ4-41 obtained in Example 6Z4. Composition 12Z4 was obtained, and a coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 113Z4

C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 101Z4, the colored curable composition 13Z4 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 114Z4

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 59, and replaced with the compound represented by the formula IZ4-1 obtained in Example 1Z4 with the compound represented by the formula IZ4-2 obtained in Example 2Z4, in the same manner as in Example 101Z4; Composition 14Z4 was obtained, and a coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 115Z4

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 59, and replaced with the compound represented by the formula IZ4-1 obtained in Example 1Z4 with the compound represented by the formula IZ4-79 obtained in Example 3Z4, in the same manner as in Example 101Z4; Composition 15Z4 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 116Z4

C.I. Pigment Green 58 C.I. It was replaced with Pigment Green 59, and the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with the compound represented by the formula IZ4-80 obtained in Example 4Z4, in the same manner as in Example 101Z4, color curability Composition 16Z4 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 117Z4

C.I. Pigment Green 58 C.I. It was replaced with Pigment Green 59, and was replaced with the compound represented by the formula IZ4-1 obtained in Example 1Z4 with the compound represented by the formula IZ4-40 obtained in Example 5Z4, in the same manner as in Example 101Z4, and colored curability Composition 17Z4 was obtained and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Example 118Z4

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 59, and replaced with the compound represented by the formula IZ4-1 obtained in Example 1Z4 with the compound represented by the formula IZ4-41 obtained in Example 6Z4, in the same manner as in Example 101Z4; Composition 18Z4 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Comparative Example 1Z4

The compound represented by the formula IZ4-1 obtained in Example 1Z4 was synthesized by C.I. Except having replaced with Pigment Yellow 185, it carried out similarly to Example 101Z4, the colored curable composition C1Z4 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Comparative Example 2Z4

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 7, the compound represented by the formula IZ4-1 obtained in Example 1Z4 was replaced with C.I. Except replacing it with Pigment Yellow 185, it carried out similarly to Example 101Z4, the colored curable composition C2Z4 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

Comparative Example 3Z4

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 59, the compound represented by the formula IZ4-1 obtained in Example 1Z4 was C.I. Except replacing with Pigment Yellow 185, it carried out similarly to Example 101Z4, obtained colored curable composition C3Z4, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z4.

[Table 9Z4]

Example 119Z4

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z4 containing liquid) in which the pigment was dispersed using a bead mill. separately,

Colorant AZ4: 50 parts of a compound represented by the formula IZ4-1;

58 parts of dispersant solution (60% solids);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and the compound represented by Formula IZ4-1 was dispersed using a bead mill to obtain a coloring composition.

next,

total amount of the obtained pigment dispersion (colorant A1Z4 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.); was mixed to obtain colored curable composition 19Z4.

It replaced with colored curable composition 1Z4, and except having used colored curable composition 19Z4, it carried out similarly to Example 101Z4, and produced the coloring pattern. Moreover, it replaced with colored curable composition 1Z4, and except having used colored curable composition 19Z4, it carried out similarly to Example 101Z4, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 10Z4.

Example 120Z4 to Example 125Z4

A coloring pattern was obtained in the same manner as in Example 119Z4 except that the compound represented by Formula IZ4-1 was replaced with the coloring agent shown in the "Colorant" column of Table 10Z4. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 10Z4.

Example 126Z4 to Example 132Z4

The compound represented by the formula IZ4-1 was replaced with the compound shown in the "Colorant" column of Table 10Z4, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 119Z4, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 10Z4.

Example 133Z4 to Example 139Z4

The compound represented by the formula IZ4-1 was replaced with the compound shown in the "Colorant" column of Table 10Z4, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 119Z4, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 10Z4.

[Table 10Z4]

In Example Z4, from the above results, in the colored coating film formed from the colored curable composition containing the compound of the present invention, C.I. It turned out that retardation value became small compared with the colored coating film formed from the colored curable composition containing Pigment Yellow 185.

[Example Z5]

Example 1Z5

25.2 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 212 parts of methanol were mixed. A mixture of 20.5 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days.

13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 10 to 20°C for 5 hours, and then stirred at 40°C for 16 hours. To the obtained mixture, 6.79 parts of acetic acid, 6.75 parts of 2-cyano-N-methylacetamide, and 201 parts of methanol were added, and the mixture was stirred at 40°C for 6 hours and at 50°C for 65 hours. To the obtained mixture, 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 604 parts of water were added, followed by stirring at 40°C for 52 hours. The resulting mixture was filtered, and the residue was washed with a 50% aqueous methanol solution. The obtained residue was dried under reduced pressure at 60 degreeC, and 49.9 parts of compounds represented by Formula IZ5-1 were obtained.

<Identification of compound represented by formula (IZ5-1)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 394

Exact Mass: 393

Example 2Z5

In the same manner as in Example 1Z5, except that 2-cyano-N-methylacetamide was replaced with 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.), the compound represented by the formula IZ5-3 was prepared got it

<Identification of compound represented by formula (IZ5-3)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 456

Exact Mass: 455

Example 3Z5

Except for replacing 4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) with 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), it was carried out in the same manner as in Example 1Z5, and the formula A compound represented by IZ5-23 was obtained.

<Identification of compound represented by formula (IZ5-23)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 383

Exact Mass: 382

Example 4Z5

4-tert-butylphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 4-nitrophthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), and 2-cyano-N-methylacetamide was replaced with 2- Except for replacing with cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1Z5 was carried out to obtain a compound represented by the formula IZ5-25.

<Identification of compound represented by formula (IZ5-25)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 445

Exact Mass: 444

Example 5Z5XXX (653)

25.2 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 212 parts of methanol were mixed. A mixture of 20.5 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days. 13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 10 to 20°C for 5 hours, and then stirred at 40°C for 16 hours. To the resulting mixture, 6.79 parts of acetic acid and 6.75 parts of 2-cyano-N-methylacetamide were added, followed by stirring at 40°C for 6 hours and at 50°C for 65 hours. In addition, 201 parts of methanol in total other than methanol described above were added up to this point.

To the obtained mixture, 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 604 parts of water were added, and the mixture was stirred at 40°C for 53 hours. The resulting mixture was filtered, and the residue was washed with a 50% aqueous methanol solution. The obtained residue was purified by column chromatography to obtain a compound represented by the formula IZ5-1.

<Identification of the compound represented by the formula IZ5-1>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 394

Exact Mass: 393

Example 6Z5XXX

10.0 parts of 4-tert- butylphthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 84 parts of methanol were mixed. A mixture of 8.15 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 1 hour. The obtained mixture was stirred under 5-20 degreeC for 2 days.

5.42 parts of acetic acid and 8.69 parts of 2-cyanoacetanilide (made by Tokyo Chemical Industry Co., Ltd.) were added to the obtained mixture under 10-20 degreeC. The resulting mixture was stirred at 65°C for 3 days.

To the obtained mixture, 2.69 parts of acetic acid and 4.35 parts of 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 65°C for 3 days. In addition, 206 parts of methanol in total other than methanol described above were added up to this time point. To the obtained mixture, 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days.

After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the mixture of the compound represented by Formula IZ5-3 was obtained.

<Identification of the compound represented by the formula IZ5-3>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 456

Exact Mass: 455

Example 7Z5XXX (654)

25.2 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 376 parts of methanol were mixed. 14.8 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining at 2 to 6°C over 20 minutes. The resulting mixture was stirred for 5 hours while maintaining at 5°C or lower.

While maintaining the obtained mixture at 5°C or lower, 9.31 parts of acetic acid and 14.4 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at room temperature for 14 hours and at 40°C for 29 hours.

To the obtained mixture, 1.50 parts of acetic acid and 2.24 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at 40°C for 19 hours.

To the resulting mixture were added 4.83 parts of acetic acid and 7.36 parts of 2-cyano-N-methylacetamide. The obtained mixture was stirred under 40 degreeC for 79 hours.

To the resulting mixture, 4.60 parts of acetic acid and 7.30 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at 40°C for 24 hours. In addition, 259 parts of methanol in total other than methanol described above were added up to this time point. To the obtained mixture, 12.1 parts of acetic acid, 19.1 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.), 635 parts of water, 14.2 parts of methanol and 20 parts of a 50% aqueous methanol solution were added, followed by 21 hours at 40°C, 5 hours at 63°C stirred.

23.4 parts of acetic acid was added to the obtained mixture, and it stirred under 63 degreeC for 18 hours. 24.9 parts of acetic acid, 19.4 parts of barbituric acid, and 32.8 parts of methanol were added to the obtained mixture, and it stirred under 63 degreeC for 7 hours. 259 parts of 50% methanol aqueous solution was added to the obtained mixture, and it stirred under 63 degreeC for 7 days. The resulting mixture was filtered. 902 parts of tetrahydrofuran was added to the obtained residue, and it stirred at room temperature. The mixture was filtered, and the obtained residue was purified by column chromatography to obtain a compound represented by the formula IZ5-23.

<Identification of the compound represented by the formula IZ5-23>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 383

Exact Mass: 382

Example 8Z5XXX

10.0 parts of 4-nitrophthalonitrile (made by Tokyo Chemical Industry Co., Ltd.) and 149 parts of methanol were mixed. 5.86 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise to the obtained mixture while maintaining at 2 to 6°C over 20 minutes. The resulting mixture was stirred for 5 hours while maintaining at 5°C or lower.

While maintaining the obtained mixture at 5°C or lower, 5.79 parts of acetic acid, 9.25 parts of 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65°C for 3 days. To the obtained mixture, 2.88 parts of acetic acid and 4.63 parts of 2-cyanoacetanilide (manufactured by Tokyo Chemical Industry Co., Ltd.) were added. The resulting mixture was stirred at 65°C for 3 days. In addition, up to this point, 140 parts of methanol in total other than methanol described above were added.

To the obtained mixture, 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and 363 parts of water were added, and the mixture was stirred at 65°C for 9 days. After solvent distillation of the obtained mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the compound represented by Formula IZ5-25 was obtained.

<Identification of the compound represented by the formula IZ5-25>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 445

Exact Mass: 444

Example 9Z5

5.0 parts of 4,5-dichlorophthalonitrile and 62 parts of methanol were mixed.

A 25% sodium methoxide methanol solution containing sodium methoxide in moles 0.5 times the moles of 5.0 parts of 4,5-dichlorophthalonitrile was added while maintaining the mixture at 5° C. or lower. The mixture was stirred at 5°C or lower for 5 hours. While maintaining 5°C or lower, 2-cyano-N-methylacetamide and 6.1 parts of acetic acid were added at 1.5 times the number of moles of 5.0 parts of 4,5-dichlorophthalonitrile. The mixture was stirred at 65° C. for 3 days.

This mixture, 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol, and 562 parts of water were mixed, and it stirred under 65 degreeC for 9 days. After solvent distillation of this mixture with a rotary evaporator, the obtained residue was refine|purified by column chromatography, and the mixture of the compound represented by Formula (IZ5-247) was obtained.

<Identification of compound represented by formula (IZ5-247)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 406

Exact Mass: 405

Example 101Z5

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z5 containing liquid) in which the pigment was dispersed using a bead mill. separately,

Colorant AZ5: 50 parts of a compound represented by the formula IZ5-1 obtained in Example 1Z5,

58 parts of dispersing agent (BYK-LPN6919; Big Chemie Japan Co., Ltd.);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and the compound represented by the formula IZ5-1 obtained in Example 1Z5 was dispersed using a bead mill to obtain a coloring composition.

next,

total amount of the obtained pigment dispersion (liquid containing colorant A1Z5);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 1Z5.

[Production of Colored Patterns]

After apply|coating colored curable composition 1Z5 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the interval between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 μm, and using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.), in an atmospheric atmosphere, an exposure amount of 80 mJ/cm 2 ( 365 nm standard). In addition, as a photomask, the thing in which the line-and-space pattern of 100 micrometers was formed was used. The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored pattern was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

[Measurement of phase difference]

After apply|coating colored curable composition 1Z5 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the colored curable composition layer was exposed at an exposure dose (365 nm standard) of 80 mJ/cm 2 in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored coating film was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

The film thickness of the obtained colored coating film was measured using DEKTAK3 (made by Nippon Vacuum Technology Co., Ltd.).

The phase difference value at the inclination angle of 45 degrees of this colored coating film was measured using the ellipsometer (M-220 type|mold spectroscopic ellipsometer; Nippon Spectroscopy Co., Ltd. product). Light with a wavelength of 550 nm was used for the phase difference value measurement. The results are shown in Table 8Z5.

Example 102Z5

A colored curable composition 2Z5 was obtained in the same manner as in Example 101Z5, except that the compound represented by the formula IZ5-1 obtained in Example 1Z5 was replaced with the compound represented by the formula IZ5-3 obtained in Example 2Z5 got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 103Z5

A colored curable composition 3Z5 was obtained in the same manner as in Example 101Z5, except that the compound represented by the formula IZ5-1 obtained in Example 1Z5 was replaced with the compound represented by the formula IZ5-23 obtained in Example 3Z5. got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 104Z5

A colored curable composition 4Z5 was obtained in the same manner as in Example 101Z5 except that the compound represented by the formula IZ5-1 obtained in Example 1Z5 was replaced with the compound represented by the formula IZ5-25 obtained in Example 4Z5 got it Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 105Z5

C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 101Z5, the colored curable composition 5Z5 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 106Z5

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z5, except that the compound represented by the formula IZ5-1 obtained in Example 1Z5 was replaced with the compound represented by the formula IZ5-3 obtained in Example 2Z5, and colored curability Composition 6Z5 was obtained, and a coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 107Z5

C.I. Pigment Green 58 C.I. It replaced with Pigment Green 7, and was carried out in the same manner as in Example 101Z5, except that the compound represented by the formula IZ5-1 obtained in Example 1Z5 was replaced with the compound represented by the formula IZ5-23 obtained in Example 3Z5. Composition 7Z5 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 108Z5

C.I. Pigment Green 58 C.I. It was replaced with Pigment Green 7, and the compound represented by the formula IZ5-1 obtained in Example 1Z5 was replaced with the compound represented by the formula IZ5-25 obtained in Example 4Z5. In the same manner as in Example 101Z5, color curability Composition 8Z5 was obtained, and a coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 109Z5

C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 101Z5, the colored curable composition 9Z5 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 110Z5

C.I. Pigment Green 58 C.I. It was replaced with Pigment Green 59, and the compound represented by the formula IZ5-1 obtained in Example 1Z5 was replaced with the compound represented by the formula IZ5-3 obtained in Example 2Z5. In the same manner as in Example 101Z5, color curability Composition 10Z5 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 111Z5

C.I. Pigment Green 58 C.I. It was replaced with Pigment Green 59, and was replaced with the compound represented by the formula IZ5-1 obtained in Example 1Z5 with the compound represented by the formula IZ5-23 obtained in Example 3Z5. In the same manner as in Example 101Z5, color curability Composition 11Z5 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Example 112Z5

C.I. Pigment Green 58 C.I. It was replaced with Pigment Green 59, and was replaced with the compound represented by the formula IZ5-1 obtained in Example 1Z5 with the compound represented by the formula IZ5-25 obtained in Example 4Z5. In the same manner as in Example 101Z5, color curability A composition 12Z5 was obtained, and a colored pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Comparative Example 1Z5

The compound represented by the formula IZ5-1 obtained in Example 1Z5 was synthesized by C.I. Except replacing it with Pigment Yellow 185, it carried out similarly to Example 101Z5, the colored curable composition C1Z5 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Comparative Example 2Z5

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 7, the compound represented by the formula IZ5-1 obtained in Example 1Z5 was C.I. Except replacing with Pigment Yellow 185, it carried out similarly to Example 101Z5, obtained colored curable composition C2Z5, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

Comparative Example 3Z5

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 59, the compound represented by the formula IZ5-1 obtained in Example 1Z5 was C.I. Except replacing it with Pigment Yellow 185, it carried out similarly to Example 101Z5, the colored curable composition C3Z5 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z5.

[Table 8Z5]

Example 113Z5

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z5 containing liquid) in which the pigment was dispersed using a bead mill. separately,

Colorant AZ5: 50 parts of a compound represented by the formula IZ5-1;

58 parts of dispersant solution (60% solids);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and the compound represented by Formula IZ5-1 was dispersed using a bead mill to obtain a coloring composition.

next,

total amount of the obtained pigment dispersion (liquid containing colorant A1Z5);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 13Z5.

It replaced with colored curable composition 1Z5, and except having used colored curable composition 13Z5, it carried out similarly to Example 101Z5, and produced the coloring pattern. Moreover, it replaced with colored curable composition 1Z5, and except having used colored curable composition 13Z5, it carried out similarly to Example 101Z5, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z5.

Example 114Z5 to Example 117Z5

A coloring pattern was obtained in the same manner as in Example 113Z5 except that the compound represented by Formula IZ5-1 was replaced with the coloring agent shown in the "Colorant" column of Table 9Z5. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z5.

Example 118Z5 to Example 122Z5

The compound represented by the formula IZ5-1 was replaced with the compound shown in the "Colorant" column of Table 9Z5, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 113Z5, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z5.

Example 123Z5 to Example 127Z5

The compound represented by the formula IZ5-1 was replaced with the compound shown in the "Colorant" column of Table 9Z5, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 113Z5, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z5.

[Table 9Z5]

In Example Z5, from the above results, in the colored coating film formed from the colored curable composition containing the compound of the present invention, C.I. It turned out that retardation value became small compared with the colored coating film formed from the colored curable composition containing Pigment Yellow 185.

[Example Z6]

Example 1Z6

7.02 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 61.6 parts of methanol were mixed. A mixture of 8.20 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 74.6 parts of methanol was added dropwise while maintaining the temperature of the obtained mixture at 2°C over 1 hour and 30 minutes. The obtained mixture was stirred under 2 degreeC for 6 hours and 15 minutes. 10.7 parts of acetic acid was added while maintaining the temperature of the obtained mixture at 4°C or lower. To the obtained mixture, 17.6 parts of benzoylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred at room temperature for 44 hours. The obtained mixture was filtered, and 800 parts of methanol wash|cleaned the residue. The obtained residue was dried under reduced pressure under 60 degreeC, and 18.0 parts of compounds represented by Formula (IFFZ6-1) were obtained.

<Identification of the compound represented by the formula IFFZ6-1>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 402

Exact Mass: 401

While stirring 7.6 parts of fuming sulfuric acid (25%) (manufactured by Wako Pure Chemical Industries, Ltd.) at 3°C, 0.513 parts of the compound represented by the formula IFFZ6-1 obtained in Example 2Z6 was added. To the obtained mixture, 3.8 parts of fuming sulfuric acid (25%) (manufactured by Wako Pure Chemical Industries, Ltd.) was added. While stirring the obtained mixture, it heated up to 15 degreeC over 3 hours and 30 minutes. 139 parts of ice water was added to the obtained mixture, and 38.2 parts of sodium chloride was further added. The obtained mixture was filtered, and the obtained residue was wash|cleaned with 64 parts of 21.5% sodium chloride aqueous solution. The obtained residue was dried under reduced pressure at 60°C to obtain 1.02 parts of a compound represented by the formula IFFZ6-2.

<Identification of the compound represented by the formula IFFZ6-2>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 560

Exact Mass: 561

At room temperature, 5.11 parts of the compound represented by the formula IFFZ6-2 and 511 parts of water were mixed. To the obtained mixture, a mixture of 6.72 parts of barium chloride dihydrate (manufactured by Wako Pure Chemical Industries, Ltd.) and 60 parts of water was added. The obtained mixture was filtered, and the obtained residue was washed with water. The obtained residue was dried under reduced pressure under 60 degreeC, and 2.98 parts of compounds represented by Formula IFZ6-4 were obtained.

<Identification of compound represented by formula IFZ6-4>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Ba ⁺ +H] ^- 560

Exact Mass: 697

Example 2Z6

At room temperature, 10.0 parts of the compound represented by the formula IFFZ6-2 and 1000 parts of water were mixed. 5% sodium hydroxide aqueous solution was dripped at the obtained mixture, and the homogeneous solution was obtained. To this homogeneous solution, 87.0 parts of a 10% aqueous solution of barium chloride dihydrate was added. The obtained mixture was filtered, and the obtained residue was washed with water. The obtained residue was dried under reduced pressure under 60 degreeC, and 9.43 parts of compounds represented by Formula IFZ6-4 were obtained.

<Identification of compound represented by formula IFZ6-4>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Ba+H] ^- 560

Exact Mass: 697

Example 3Z6

At room temperature, 5.02 parts of a compound represented by the formula IFFZ6-2 and 500 parts of a 50% aqueous methanol solution were mixed. 5% sodium hydroxide aqueous solution was dripped at the obtained mixture, and the homogeneous solution was obtained. To this homogeneous solution, 95.0 parts of a 10% aqueous solution of strontium chloride hexahydrate was added. The obtained mixture was filtered, and the obtained residue was wash|cleaned with 50% methanol aqueous solution. The obtained residue was dried under reduced pressure at 60°C to obtain 4.00 parts of a compound represented by the formula IFZ6-3.

<Identification of compound represented by formula IFZ6-3>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Sr+H] ^- 560

Exact Mass: 647

Example 4Z6

At room temperature, 0.501 parts of the compound represented by the formula IFFZ6-2 and 50.0 parts of water were mixed. 5% sodium hydroxide aqueous solution was dripped at the obtained mixture, and the homogeneous solution was obtained. 12.6 parts of 10% calcium chloride aqueous solution was added to this homogeneous solution. The obtained mixture was filtered, and the obtained residue was washed with water. The obtained residue was dried under reduced pressure at 60°C to obtain 0.024 parts of a compound represented by the formula IFZ6-2.

<Identification of compound represented by formula IFZ6-2>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Ca+H] ^- 560

Exact Mass: 599

Example 5Z6

At room temperature, 0.500 parts of the compound represented by the formula IFFZ6-2 and 50.0 parts of water were mixed. 5% sodium hydroxide aqueous solution was dripped at the obtained mixture, and the homogeneous solution was obtained. To this homogeneous solution, 3.52 parts of a 10% aqueous solution of manganese chloride tetrahydrate was added. The obtained mixture was filtered, and the obtained residue was washed with water. The obtained residue was dried under reduced pressure at 60°C to obtain 0.015 parts of a compound represented by the formula IFZ6-10.

<Identification of the compound represented by the formula IFZ6-10>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Mn+H] ^- 560

Exact Mass: 614

Example 6Z6

Except for replacing barium chloride dihydrate with zinc nitrate hexahydrate, it carried out similarly to Example 2Z6, and obtained the compound represented by Formula IFZ6-6.

<Identification of compound represented by formula IFZ6-6>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Zn+H] ^- 560

Exact Mass: 623

Example 7Z6

At room temperature, 5.00 parts of the compound represented by the formula IFFZ6-2 and 500 parts of water were mixed. 5% sodium hydroxide aqueous solution was dripped at the obtained mixture, and the homogeneous solution was obtained. 23.7 parts of 10% aluminum chloride aqueous solution was added to this homogeneous solution. The obtained mixture was filtered, and the obtained residue was washed with water. The obtained residue was dried under reduced pressure at 60°C to obtain 0.474 parts of a compound represented by the formula IFZ6-11.

<Identification of the compound represented by the formula IFZ6-11>

(Mass spectrometry) Ionization mode = ESI-: m/z = [(M-2Al)/3+H] ^- 560

Exact Mass: 1731

Example 8Z6

At room temperature, 5.01 parts of the compound represented by the formula IFFZ6-2 and 500 parts of water were mixed. 5% sodium hydroxide aqueous solution was dripped at the obtained mixture, and the homogeneous solution was obtained. To this homogeneous solution, 36.0 parts of 10% aqueous iron nitrate heptahydrate solution was added. The obtained mixture was filtered, and the obtained residue was washed with water. The obtained residue was dried under reduced pressure at 60°C to obtain 3.80 parts of a compound represented by the formula IFZ6-12.

<Identification of the compound represented by the formula IFZ6-12>

(Mass spectrometry) Ionization mode = ESI-: m/z = [(M-2Fe)/3+H] ^- 560

Exact Mass: 1789

Example 9Z6

At room temperature, 0.498 parts of the compound represented by the formula IFFZ6-2 and 49.9 parts of water were mixed. 5% sodium hydroxide aqueous solution was dripped at the obtained mixture, and the homogeneous solution was obtained. To this homogeneous solution, 4.45 parts of a 10% aqueous solution of copper sulfate pentahydrate was added. The obtained mixture was filtered, and the obtained residue was washed with water. The obtained residue was dried under reduced pressure at 60°C to obtain 0.018 parts of a compound represented by the formula IFZ6-31.

<Identification of the compound represented by the formula IFZ6-31>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Cu+H] ^- 560

Exact Mass: 622

Example 10Z6

A compound represented by the formula IJJZ6-1 was obtained in the same manner as in the method for obtaining the compound represented by the formula IFFZ6-1 in Example 1Z6 except that benzoylacetonitrile was replaced with 4-cyanoacetylbenzoic acid.

<Identification of the compound represented by the formula IJJZ6-1>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 488

Exact Mass: 489

At room temperature, 16.3 parts of the compound represented by the formula IJJZ6-1 and 1630 parts of water were mixed. 5% sodium hydroxide aqueous solution was dripped at the obtained mixture, and the homogeneous solution was obtained. To the obtained homogeneous solution, 163 parts of a 10% aqueous solution of barium chloride dihydrate was added. The obtained mixture was filtered, and the obtained residue was washed with water. The obtained residue was dried under reduced pressure under 60 degreeC, and 7.49 parts of compounds represented by Formula IJZ6-4 were obtained.

<Identification of compound represented by formula IJZ6-4>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Ba+H] ^- 488

Exact Mass: 625

Example 11Z6

A compound represented by the formula IJZ6-3 was obtained in the same manner as in Example 10Z6 except that barium chloride dihydrate was replaced with strontium chloride hexahydrate.

<Identification of compound represented by formula IJZ6-3>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Sr+H] ^- 488

Exact Mass: 575

Example 12Z6

Except for replacing barium chloride dihydrate with calcium chloride, it carried out similarly to Example 10Z6, and obtained the compound represented by Formula IJZ6-2.

<Identification of compound represented by formula IJZ6-2>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Ca+H] ^- 488

Exact Mass: 527

Example 13Z6

Except for replacing barium chloride dihydrate with manganese chloride tetrahydrate, it carried out similarly to Example 10Z6, and obtained the compound represented by Formula IJZ6-10.

<Identification of the compound represented by the formula IJZ6-10>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Mn+H] ^- 488

Exact Mass: 542

Example 14Z6

Except replacing barium chloride dihydrate with copper sulfate pentahydrate, it carried out similarly to Example 10Z6, and obtained the compound represented by Formula IJZ6-31.

<Identification of compound represented by formula IJZ6-31>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Cu+H] ^- 488

Exact Mass: 550

Example 15Z6

Except having replaced barium chloride dihydrate with zinc nitrate hexahydrate, it carried out similarly to Example 10Z6, and obtained the compound represented by Formula IJZ6-6.

<Identification of compound represented by formula IJZ6-6>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Zn+H] ^- 488

Exact Mass: 551

Example 16Z6

Except for replacing barium chloride dihydrate with aluminum chloride, it carried out similarly to Example 10Z6, and obtained the compound represented by Formula IJZ6-11.

<Identification of the compound represented by the formula IJZ6-11>

(Mass spectrometry) Ionization mode = ESI-: m/z = [(M-2Al)/3+H] ^- 488

Exact Mass: 1515

Example 17Z6

Except having replaced barium chloride dihydrate with iron nitrate heptahydrate, it carried out similarly to Example 10Z6, and obtained the compound represented by Formula IJZ6-12.

<Identification of the compound represented by the formula IJZ6-12>

(Mass spectrometry) Ionization mode = ESI-: m/z = [(M-2Fe)/3+H] ^- 488

Exact Mass: 1573

Example 18Z6

Except replacing the barium chloride dihydrate with magnesium chloride, it carried out similarly to Example 10Z6, and obtained the compound represented by Formula IJZ6-1.

<Identification of compound represented by formula IJZ6-1>

(Mass spectrometry) Ionization mode = ESI-: m/z = [M-Mg+H] ^- 488

Exact Mass: 511

Example 19Z6

5.00 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 44 parts of methanol were mixed. A mixture of 5.84 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 54 parts of methanol was added dropwise to the obtained mixture while maintaining at 5°C or lower over 1 hour and 30 minutes. The obtained mixture was stirred at 5 degrees C or less for 12 hours. 11.5 parts of acetic acid were added to the obtained mixture, maintaining at 5 degrees C or less, and 24.5 parts of 4-cyanoacetylbenzoic acid and 712 parts of methanol were also added. The resulting mixture was stirred at room temperature for 4 hours, and then stirred at 40°C for 96 hours. After solvent-distilling the obtained mixture with the rotary evaporator, the obtained residue was refine|purified by column chromatography, and 0.471 parts of compounds represented by Formula IJJZ6-1 were obtained.

<Identification of compound represented by formula IJJZ6-1>

(Mass spectrometry) Ionization mode = ESI-: m/z = [MH] ^- 488

Exact Mass: 489

Example 101Z6

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion (colorant A1Z6 containing liquid) in which the pigment was dispersed using a bead mill. separately,

Colorant AZ6: 50 parts of a compound represented by the formula IFZ6-4;

58 parts of dispersant (BYK-LPN6919; Big Chemie Japan Co., Ltd.);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and the compound represented by the formula IFZ6-4 was dispersed using a bead mill to obtain a coloring composition. next,

total amount of the obtained pigment dispersion (colorant A1Z6 containing liquid);

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain colored curable composition 1Z6.

[Production of Colored Patterns]

After apply|coating colored curable composition 1Z6 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the interval between the substrate on which the colored curable composition layer was formed and the quartz glass photomask was set to 200 µm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used in an atmospheric atmosphere, an exposure amount of 80 mJ/cm 2 ( 365 nm standard). In addition, as a photomask, the thing in which the line-and-space pattern of 100 micrometers was formed was used. The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, and it developed and washed with water. The colored pattern was obtained by post-baking this colored curable composition layer at 230 degreeC for 30 minute(s).

[Measurement of phase difference]

After apply|coating colored curable composition 1Z6 by the spin coating method on the glass substrate (Eagle XG; Corning company make) of 2 inches by width, it prebaked at 100 degreeC for 3 minutes, and the colored curable composition layer was formed. After cooling, the colored curable composition layer was exposed at an exposure dose (365 nm standard) of 80 mJ/cm 2 in an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). The colored curable composition layer after exposure was immersed in the aqueous solution containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 25 degreeC for 70 second, it developed, washed with water, and dried. The colored coating film was obtained by post-baking the colored curable composition layer after drying at 230 degreeC for 30 minute(s).

The film thickness of the obtained colored coating film was measured using DEKTAK3 (made by Nippon Vacuum Technology Co., Ltd.). The phase difference value at the inclination angle of 45 degrees of this colored coating film was measured using the ellipsometer (M-220 type|mold spectroscopic ellipsometer; Nippon Spectroscopy Co., Ltd. product). Light with a wavelength of 550 nm was used for the phase difference value measurement. The results are shown in Table 5Z6.

Example 102Z6

Except having replaced the compound represented by formula IFZ6-4 with the compound represented by formula IFZ6-2, it carried out similarly to Example 101Z6, obtained colored curable composition 2Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 103Z6

Except having replaced the compound represented by formula IFZ6-4 with the compound represented by formula IFZ6-3, it carried out similarly to Example 101Z6, obtained colored curable composition 3Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 104Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IFZ6-6, it carried out similarly to Example 101Z6, the colored curable composition 4Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 105Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IFZ6-10, it carried out similarly to Example 101Z6, the colored curable composition 5Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 106Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IFZ6-11, it carried out similarly to Example 101Z6, the colored curable composition 6Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 107Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IFZ6-12, it carried out similarly to Example 101Z6, the colored curable composition 7Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 108Z6

Except having replaced the compound represented by formula IFZ6-4 with the compound represented by formula IFZ6-31, it carried out similarly to Example 101Z6, obtained colored curable composition 8Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 109Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IJZ6-1, it carried out similarly to Example 101Z6, the colored curable composition 9Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 110Z6

Except having replaced the compound represented by formula IFZ6-4 with the compound represented by formula IJZ6-2, it carried out similarly to Example 101Z6, obtained colored curable composition 10Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 111Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IJZ6-3, it carried out similarly to Example 101Z6, obtained colored curable composition 11Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 112Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IJZ6-4, it carried out similarly to Example 101Z6, the colored curable composition 12Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 113Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IJZ6-6, it carried out similarly to Example 101Z6, the colored curable composition 13Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 114Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IJZ6-10, it carried out similarly to Example 101Z6, the colored curable composition 14Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 115Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IJZ6-11, it carried out similarly to Example 101Z6, obtained colored curable composition 15Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 116Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IJZ6-12, it carried out similarly to Example 101Z6, the colored curable composition 16Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 117Z6

Except having replaced the compound represented by Formula IFZ6-4 with the compound represented by Formula IJZ6-31, it carried out similarly to Example 101Z6, the colored curable composition 17Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 5Z6.

Example 118Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-2, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 18Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 119Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-3, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 19Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 120Z6

C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, obtained colored curable composition 20Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 121Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-6, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 21Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 122Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-10, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, obtained colored curable composition 22Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 123Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-11, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 23Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 124Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-12, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 24Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 125Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-31, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 25Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 126Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-1, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 26Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 127Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-2, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 27Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 128Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-3, and C.I. Pigment Green 58 C.I. Except replacing it with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 28Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 129Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-4, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 29Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 130Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-6, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 30Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 131Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-10, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 31Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 132Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-11, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 32Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 133Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-12, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 33Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 134Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-31, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 34Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 6Z6.

Example 135Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-2, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 101Z6, the colored curable composition 35Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 136Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-3, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 36Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 137Z6

C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 37Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 138Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-6, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 38Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 139Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-10, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 39Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 140Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-11, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 40Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 141Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-12, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 41Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 142Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IFZ6-31, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 42Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 143Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-1, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 43Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 144Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-2, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 44Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 145Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-3, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 45Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 146Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-4, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 46Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 147Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-6, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 47Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 148Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-10, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 48Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 149Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-11, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 49Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 150Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-12, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 50Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Example 151Z6

The compound represented by the formula IFZ6-4 is substituted for the compound represented by the formula IJZ6-31, and C.I. Pigment Green 58 C.I. Except replacing with Pigment Green 59, it carried out similarly to Example 101Z6, the colored curable composition 51Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 7Z6.

Comparative Example 1Z6

The compound represented by the formula IFZ6-4 was treated with C.I. Except having replaced with Pigment Yellow 185, it carried out similarly to Example 101Z6, the colored curable composition C1Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z6.

Comparative Example 2Z6

C.I. Pigment Green 58 C.I. Substituted for Pigment Green 7, the compound represented by the formula IFZ6-4 was replaced with C.I. Except replacing it with Pigment Yellow 185, it carried out similarly to Example 101Z6, the colored curable composition C2Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z6.

Comparative Example 3Z6

C.I. Pigment Green 58 C.I. The compound represented by the formula IFZ6-4 was replaced with Pigment Green 59, and C.I. Except having replaced with Pigment Yellow 185, it carried out similarly to Example 101Z6, the colored curable composition C3Z6 was obtained, and the coloring pattern was obtained. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 8Z6.

[Table 5Z6]

[Table 6Z6]

[Table 7Z6]

[Table 8Z6]

Example 152Z6

Pigment: C.I. Pigment Green 58 60 parts,

8.1 parts of an acrylic pigment dispersant;

Resin (B): 73 parts of resin B5 solution, and

Solvent (E): 290 parts of propylene glycol monomethyl ether acetate

was mixed to prepare a pigment dispersion liquid (colorant A1Z6 containing liquid) in which the pigment was dispersed using a bead mill. separately,

Colorant AZ6: 50 parts of a compound represented by the formula IFZ6-4;

58 parts of dispersant solution (60% solids);

Resin (B): 93 parts of resin B3 solution, and

Solvent (E): 800 parts of propylene glycol monomethyl ether acetate

was mixed, and the compound represented by the formula IFZ6-4 was dispersed using a bead mill to obtain a coloring composition. next,

total amount of the obtained pigment dispersion (colorant A1Z6) containing liquid;

400 parts of the obtained coloring composition;

Resin (B): 45 parts of resin B1 solution;

Polymeric compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (trademark) DPHA; Nippon Kayaku Co., Ltd. product);

Polymerization initiator (D): 15 parts of N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Corporation) ;

Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and

Leveling agent: 0.12 parts of polyether-modified silicone oil (Toray Silicone SH8400; Toray Dow Corning Co., Ltd.);

was mixed to obtain a colored curable composition 52Z6.

It replaced with colored curable composition 1Z6, and except having used colored curable composition 52Z6, it carried out similarly to Example 101Z6, and produced the coloring pattern. Moreover, it replaced with colored curable composition 1Z6, and except having used colored curable composition 52Z6, it carried out similarly to Example 101Z6, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z6.

Example 153Z6 to Example 168Z6

A coloring pattern was obtained in the same manner as in Example 152Z6 except that the compound represented by the formula IFZ6-4 was replaced with the compound shown in the "Colorant" column of Table 9Z6. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 9Z6.

Example 169Z6 to Example 185Z6

The compound represented by the formula IFZ6-4 was replaced with the compound shown in the "Colorant" column of Table 10Z6, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 7, it carried out similarly to Example 152Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 10Z6.

Example 186Z6 to Example 202Z6

The compound represented by the formula IFZ6-4 was replaced with the compound shown in the "Colorant" column of Table 11Z6, and C.I. Pigment Green 58 C.I. Except having replaced with Pigment Green 59, it carried out similarly to Example 152Z6, and obtained the coloring pattern. Moreover, the colored coating film was obtained, and the film thickness measurement and phase difference value measurement were performed. The results are shown in Table 11Z6.

[Table 9Z6]

[Table 10Z6]

[Table 11Z6]

In Example Z6, from the above results, in the colored coating film formed from the colored curable composition containing the compound of the present invention, C.I. It turned out that retardation value became small compared with the colored coating film formed from the colored curable composition containing Pigment Yellow 185.

Since the coloring composition and compound of this invention can be used for formation of a color filter with a small phase difference value, they are used suitably for display apparatuses, such as a color filter and a liquid crystal display device.

Claims (16)

A compound represented by the formula IZ2,
The coloring composition containing at least one of resin and a solvent.

[In formula IZ2, R ^CO1Z2 and R ^CO2Z2 each independently represent -OR ^O1Z2 or -NR ^N1Z2 R ^N2Z2 . R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^2Z2 , R ^3Z2 , R ^4Z2 , and R ^5Z2 are, independently of each other, a hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO -R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N(R ^{102Z2 )} ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or a C1-C40 hydrocarbon group which may have a substituent.
R ^2Z2 and R ^3Z2 , R ^3Z2 and R ^4Z2 , and R ^4Z2 and R ^5Z2 may be respectively bonded to each other to form a ring.
R ^101Z2 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R ^O1Z2 and R ^102Z2 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When two or more R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^101Z2 , R ^102Z2 and M exist, they may be the same or different. The broken line indicates the E or Z body.] The method of claim 1,
A coloring composition comprising a resin. 3. The method according to claim 1 or 2,
R ^O1Z2 , R ^N1Z2 and R ^N2Z2 are each independently a hydrogen atom or a C1-C10 hydrocarbon group which may have a substituent, The coloring composition. 4. The method according to any one of claims 1 to 3,
A coloring composition wherein R ^1Z2 is a hydrogen atom. 5. The method according to any one of claims 1 to 4,
At least one of R ^2Z2 , R ^3Z2 , R ^4Z2 , and R ^5Z2 is -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO-R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON (R ^102Z2 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or R ^2Z2 and R ^3Z2 , R ^3Z2 and A coloring composition wherein at least one set of R ^4Z2 and R ^4Z2 and R ^5Z2 is bonded to form a ring. 6. The method according to any one of claims 1 to 5,
At least one of R ^2Z2 , R ^3Z2 , R ^4Z2 , and R ^5Z2 is a nitro group or a tert-butyl group. 7. The method according to any one of claims 1 to 6,
The coloring composition containing both resin and a solvent. 8. The method according to any one of claims 1 to 7,
Further, a coloring composition comprising a yellow colorant or a green colorant. The colored curable composition containing the coloring composition in any one of Claims 1-8, and a polymeric compound. 10. The method of claim 9,
Further, a colored curable composition comprising a polymerization initiator. The color filter formed from the coloring composition in any one of Claims 1-8, or the colored curable composition of Claim 9 or 10. A liquid crystal display device comprising the color filter according to claim 11 . A compound represented by the formula IZ2-B.

[In formula IZ2-B, R ^CO11Z2 and R ^CO21Z2 independently represent -OR ^O1Z2 or -NR ^N1Z2 R ^N2Z2 , and at least one of R ^CO11Z2 and R ^CO21Z2 is -NR ^N1Z2 R ^N2Z2 .
R ^N1Z2 , R ^N2Z2 , R ^1Z2 , R ^21Z2 , R ^31Z2 , R ^41Z2 and R ^51Z2 are, independently of each other, a hydrogen atom, -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO- R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N (R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON(R ^102Z2 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent and R ^21Z2 and R ^31Z2 , R ^31Z2 and R ^41Z2 , and R ^41Z2 and R ^51Z2 may be bonded to each other to form a ring,
At least one of R ^21Z2 , R ^31Z2 , R ^41Z2 and R ^51Z2 is -CO-R ^102Z2 , -COO-R ^101Z2 , -OCO-R ^102Z2 , -COCO-R ^102Z2 , -OR ^102Z2 , -SO ₂ -R ^101Z2 , -SO ₂ N(R ^102Z2 ) ₂ , -CON(R ^102Z2 ) ₂ , -N(R ^102Z2 ) ₂ , -NHCO-R ^102Z2 , -NHCO-N(R ^102Z2 ) ₂ , -NHCOOR ^102Z2 , -OCON( R ^102Z2 ) ₂ , a halogen atom, a cyano group, a nitro group, -SO ₃ M, -CO ₂ M, or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or R ^21Z2 and R ^31Z2 , R ^31Z2 and R ^41Z2 and at least one set of R ^41Z2 and R ^51Z2 are bonded to each other to form a ring.
R ^101Z2 represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R ^O1Z2 and R ^102Z2 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
When two or more R ^O1Z2 , R ^N1Z2 , R ^N2Z2 , R ^101Z2 , R ^102Z2 and M exist, they may be the same or different. The broken line indicates the E or Z body.] 14. The method of claim 13,
A compound in which R ^O1Z2 , R ^N1Z2 and R ^N2Z2 are a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. 15. The method according to claim 13 or 14,
A compound wherein R ^1Z2 is a hydrogen atom. 16. The method according to any one of claims 13 to 15,
A compound wherein at least one of R ^21Z2 , R ^31Z2 , R ^41Z2 and R ^51Z2 is a nitro group or a tert-butyl group.