JPWO2021213087A5 - - Google Patents

Description

In a further embodiment, R ₁ is selected from a phenyl group, a naphthyl group, a pyrrolyl group, an imidazolyl group, a carbazolyl group, an indolyl group, a C ₂ -C ₁₀ alkenyl group, a C ₄ -C ₈ cycloalkadienyl group. , or the hydrogen atoms in the group each independently represent a C ₁ to C ₁₀ linear or branched alkyl group, a C ₄ to C ₁₀ alkylcycloalkyl group or a cycloalkylalkyl group, a C ₃ to C ₁₀ cyclo Substituted by an alkyl group, a C ₆ -C ₁₅ aryl group, a C ₆ -C ₁₂ alkylaryl group, a C ₆ -C ₁₂ arylalkyl group, a C ₂ -C ₂₀ heteroaryl group. R ₂ is selected from hydrogen, C ₁ to C ₆ straight chain or branched alkyl groups. R ₃ is selected from hydrogen, a C ₁ to C ₆ straight or branched alkyl group, and a benzyl group.

In a further embodiment, R ₁ is a phenyl group, a naphthyl group, a pyrrolyl group, an imidazolyl group, a carbazolyl group, an indolyl group, a C ₂ to C ₆ alkenyl group, a C ₄ to C ₆ cycloalkadienyl group, a C ₁ to Phenyl group substituted with C ₅ alkyl group, phenyl group substituted with C ₃ to C ₆ cycloalkyl group, alkenyl group substituted with C ₆ to C ₁₀ aryl group, C ₆ to C ₁₀ alkyl group It is selected from an alkenyl group substituted with an aryl group, and an alkenyl group substituted with a C ₆ to C ₁₀ arylalkyl group.

In order to further improve the overall performance of the EO/PO-modified pyrazoline organic material, in one preferred embodiment, R ₁ is a phenyl group, a naphthyl group, a pyrrolyl group, an imidazolyl group, a carbazolyl group, an indolyl group, a C ₂ - selected from a C ₁₀ alkenyl group, a C ₄ to C ₈ cycloalkadienyl group, or the hydrogen atoms in the group are each independently selected from a C ₁ to C ₁₀ straight or branched alkyl group, a C ₄ ~C ₁₀ alkylcycloalkyl group or cycloalkylalkyl group, C ₃ to C ₁₀ cycloalkyl group, C ₆ to C ₁₅ aryl group, C ₆ to C ₁₂ alkylaryl group, C ₆ to C ₁₂ aryl Alkyl group, substituted by C ₂ -C ₂₀ heteroaryl. R ₂ is selected from hydrogen, C ₁ to C ₆ straight chain or branched alkyl groups. R ₃ is selected from hydrogen, a C1 to C6 straight or branched alkyl group, and a benzyl group.

In order to improve the conjugation between R ₁ and the sensitizer represented by formula (I) and improve the photosensitivity, R ₁ is preferably a phenyl group, a naphthyl group, a pyrrolyl group, an imidazolyl group, Carbazolyl group, indolyl group, C ₂ to C ₆ alkenyl group, C ₄ to C ₆ cycloalkadienyl group, phenyl group substituted with C ₁ to C ₅ alkyl group, C ₃ to C ₆ cycloalkyl group a phenyl group substituted with a C ₆ to C ₁₀ aryl group, an alkenyl group substituted with a C ₆ to C ₁₀ alkylaryl group, an alkenyl group substituted with a C ₆ to C ₁₀ arylalkyl group, selected from alkenyl groups. In order to further reduce the difficulty in synthesizing the EO/PO-modified pyrazoline organic material, R ₁ is more preferably one selected from the following groups.

Claims (14)

An ethoxy/propoxy-modified pyrazoline compound characterized by having a structure represented by the following formula (I).

[In the formula, X and Y each independently represent -CH ₂ -CH ₂ - or -CH(CH ₃ )-CH ₂ -.
p and q each independently represent an integer from 0 to 9, and both are not 0 at the same time.
R ₁ is selected from a phenyl group, a naphthyl group, a pyrrolyl group, an imidazolyl group, a carbazolyl group, an indolyl group, a C ₂ to C ₁₀ alkenyl group, and a C ₄ to C ₈ cycloalkadienyl group; Hydrogen atoms each independently represent a C ₁ to C ₁₀ linear or branched alkyl group, a C ₃ to C ₁₀ cycloalkyl group, a C ₆ to C ₁₅ aryl group, or a C ₆ to C ₁₂ alkylaryl group. , a C ₆ to C ₁₂ arylalkyl group, or a C ₂ to ₂₀ heteroaryl group.
R ₂ represents hydrogen, a C ₁ to C ₁₀ linear or branched alkyl group, a C ₄ to C ₁₀ alkylcycloalkyl group, or a cycloalkylalkyl group.
R ₃ represents hydrogen, a C ₁ to C ₆ linear or branched alkyl group , or a C ₆ to C ₂₀ arylalkyl group. ] The ethoxy/propoxy-modified pyrazoline compound according to claim 1, characterized in that p+q≦9. The R ₂ is selected from hydrogen, a C ₁ to C ₆ straight chain or branched alkyl group,
The ethoxy/propoxy-modified pyrazoline compound according to claim 1 , wherein R ₃ is selected from hydrogen, a C ₁ to C ₆ linear or branched alkyl group, and a benzyl group. R ₁ is a phenyl group, a naphthyl group, a pyrrolyl group, an imidazolyl group, a carbazolyl group, an indolyl group, a C ₂ to C ₆ alkenyl group, a C ₄ to C ₆ cycloalkadienyl group, a C ₁ to C ₅ A phenyl group substituted with an alkyl group, a phenyl group substituted with a C ₃ to C ₆ cycloalkyl group, an alkenyl group substituted with a C ₆ to C ₁₀ aryl group, a C ₆ to C ₁₀ alkylaryl group The ethoxy/propoxy-modified pyrazoline compound according to claim 1, which is selected from substituted alkenyl groups and alkenyl groups substituted with C ₆ to C ₁₀ arylalkyl groups. Said R ₁ is

The ethoxy/propoxy-modified pyrazoline compound according to claim 1 , characterized in that it is selected from the following. 2. The method according to claim 1 , wherein R ₂ is selected from hydrogen, methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, or CH ₃ C(CH ₂ CH ₃ ) ₂ -. Ethoxy/propoxy modified pyrazoline compounds as described. The ethoxy/propoxy modified pyrazoline compound according to claim 1 , wherein the ethoxy/propoxy modified pyrazoline compound is one or more selected from the following compounds .

The ethoxy/propoxy-modified pyrazoline compound according to claim 1, characterized in that p+q≦6. (A) an alkali-soluble polymer, (B) a compound having an ethylenically unsaturated double bond, (C) a first sensitizer, and (D) a photoinitiator and/or a second sensitizer. and (E) any other auxiliary agent, wherein the first sensitizer is the ethoxy/propoxy-modified pyrazoline compound according to any one of claims 1 to 8 , and the second A photocurable composition characterized in that a sensitizer is different from the first sensitizer. The alkali-soluble polymers include (meth)acrylic polymers, styrene polymers, epoxy polymers, aliphatic urethane (meth)acrylate polymers, aromatic urethane (meth)acrylate polymers, amide resins, and amide resins. The photocurable composition according to claim 9 , characterized in that it is one or more selected from the group consisting of epoxy resins, alkyd resins, and phenolic resins. The compound having an ethylenically unsaturated double bond is a compound obtained by reacting an α,β-unsaturated carboxylic acid with a polyhydric alcohol, a bisphenol A-based (meth)acrylate compound, an α,β-unsaturated carboxylic acid, etc. Compounds obtained by reacting acids with glycidyl group-containing compounds, (meth)acrylate compounds having urethane bonds in the molecule, nonylphenoxypolyethyleneoxyacrylate, γ-chloro-β-hydroxypropyl-β'-(meth)acryloyl Oxyethyl-o-phthalate, β-hydroxyethyl-β'-(meth)acryloyloxyethyl-o-phthalate, β-hydroxypropyl-β'-(meth)acryloyloxyethyl-o-phthalate, phthalic acid compounds, The photocurable composition according to claim 9, characterized in that it is one or more selected from the group consisting of alkyl (meth)acrylates. The auxiliary agent is one or more selected from the group consisting of a hydrogen donor, a dye, a pigment, a photochromic agent, a filler, a plasticizer, a stabilizer, a coating aid, and a release accelerator. The photocurable composition according to claim 9. Use of the ethoxy/propoxy-modified pyrazoline compound according to any one of claims 1 to 8 in the field of photocuring. A photoresist comprising the photocurable composition according to claim 9 .