JP7344001B2 - polymer - Google Patents

Description

The present invention relates to a polymer having a repeating unit that is degradable to light of a specific wavelength, a photodegradable resin containing the polymer, a composition containing the photodegradable resin, and a composition containing the composition. The present invention relates to a photoremovable adhesive, a pattern forming agent, and a photolatent catalyst.

In recent years, there has been an increasing need for light-easily dismantled adhesives, pattern-forming agents that can form fine patterns, and photo-latent catalysts that have excellent storage stability in order to reduce environmental impact and cost.

Patent Document 1 discloses a method for producing a photodegradable polymer compound having an o-nitrobenzyl group. Patent Document 2 discloses a photodegradable acrylic copolymer having oxime methacrylate having a specific structure as a structural unit.

Japanese Patent Application Publication No. 2007-131710 Japanese Unexamined Patent Publication No. 63-260912

However, existing techniques have problems in that the sensitivity of photolysis is low and the effect of reducing molecular weight by photolysis is small.

The problem to be solved by the present invention is to provide a polymer, a photodegradable resin, a composition, a photo-disassembleable adhesive, a pattern-forming agent, and a photo-latent catalyst that can solve the above problems.

The present inventors conducted extensive studies to solve the above problems, and achieved the above problems by providing the following [1] to [15].

[1]
Selected from the group consisting of a structural unit represented by the following formula (Iα), a structural unit represented by the formula (Iβ), a structural unit represented by the formula (Iγ), and a structural unit represented by the formula (Iδ) one or more types of structural units,
A polymer having one or more structural units selected from the group consisting of a structural unit represented by the following formula (IIα), a structural unit represented by the formula (IIβ), and a structural unit represented by the formula (IIγ) .

In the formula, R ¹ represents a hydrogen atom or a methyl group,
R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom, a nitrile group, a heterocyclic group, a hydrocarbon group having 1 to 30 carbon atoms, or one of the methylene groups in the hydrocarbon group; Represents a group in which two or more of the methylene groups are replaced with a divalent group selected from the group Iα below, provided that when two or more methylene groups are replaced with a divalent group selected from the group Iα below, the two The valent groups are not adjacent to each other, and one or more hydrogen atoms in the groups represented by R ² , R ³ and R ⁴ are a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, or a halogen group. may be substituted with an atom, nitro group, cyano group, hydroxyl group, amino group, methacryloyl group, acryloyl group, epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
Q ¹ represents -O-, -CO-O- or -O-CO-,
X ¹ represents a single bond or a methylene group,
Y ¹ is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-divalent A heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or one or more methylene groups in the hydrocarbon group is replaced with a divalent group selected from the following group IIα. group, provided that when two or more methylene groups are replaced with divalent groups selected from Group IIα below, the divalent groups are not adjacent to each other, and hydrogen in the group represented by Y ¹ One or more of the atoms is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl may be substituted with a group, a mercapto group, an isocyanate group or a carboxyl group,
n represents an integer from 1 to 12,
When the polymer contains a plurality of structural units represented by (Iα), the plurality of R ¹ , R ² , R ³ , R ⁴ , Q ¹ , X ¹ and Y ¹ may be the same or different. In some cases,
* represents a bond.
Group Iα: -O-, -S- or divalent heterocyclic group.
Group IIα: -O-, -S-, -NR ¹⁹¹ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ¹⁹¹ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ⁵ represents a hydrogen atom or a methyl group,
R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, a halogen atom, a nitrile group, a heterocyclic group, a hydrocarbon group having 1 to 30 carbon atoms, or one of the methylene groups in the hydrocarbon group; Represents a group in which two or more of the methylene groups are substituted with divalent groups selected from the following group Iβ, provided, however, that when two or more methylene groups are replaced with divalent groups selected from the following group Iβ, the two The valent groups are not adjacent to each other, and one or more hydrogen atoms in the groups represented by R ⁶ , R ⁷ and R ⁸ are a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, or a halogen group. may be substituted with an atom, nitro group, cyano group, hydroxyl group, amino group, methacryloyl group, acryloyl group, epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
Q ² represents -O-, -CO-O- or -O-CO-,
X ² represents a single bond or a methylene group,
Y ² is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, 2 a valent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or one or more methylene groups in the hydrocarbon group is replaced with a divalent group selected from the following group IIβ. However, when two or more methylene groups are replaced with divalent groups selected from Group IIβ below, the divalent groups are not adjacent to each other, and ^Y One or more of the hydrogen atoms is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, May be substituted with vinyl group, mercapto group, isocyanate group or carboxyl group,
n represents an integer from 1 to 12,
When the polymer contains a plurality of structural units represented by (Iβ), the plurality of R ⁵ , R ⁶ , R ⁷ , R ⁸ , Q ² , X ² and Y ² may be the same or different. In some cases,
* represents a bond.
Group Iβ: -O-, -S- or divalent heterocyclic group.
Group IIβ: -O-, -S-, -NR ¹⁹² -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group, R ¹⁹² represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ⁹ represents a hydrogen atom or a methyl group,
R ¹⁰ , R ¹¹ and R ¹² each independently represent a hydrogen atom, a halogen atom, a nitrile group, a heterocyclic group, a hydrocarbon group having 1 to 30 carbon atoms, or one of the methylene groups in the hydrocarbon group; Represents a group in which two or more of the methylene groups are replaced with a divalent group selected from the group Iγ below, provided that when two or more methylene groups are replaced with a divalent group selected from the group Iγ below, the two The valent groups are not adjacent to each other, and one or more hydrogen atoms in the groups represented by R ¹⁰ , R ¹¹ and R ¹² are a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, or a halogen group. may be substituted with an atom, nitro group, cyano group, hydroxyl group, amino group, methacryloyl group, acryloyl group, epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
Q ³ represents -O-, -CO-O- or -O-CO-,
X ³ represents a single bond or a methylene group,
Y ³ is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, 2 a valent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or one or more methylene groups in the hydrocarbon group is replaced with a divalent group selected from the following group IIγ. However, when two or more methylene groups are replaced with divalent groups selected from Group IIγ below, the divalent groups are not adjacent to each other, ^and One or more of the hydrogen atoms is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, May be substituted with vinyl group, mercapto group, isocyanate group or carboxyl group,
n represents an integer from 1 to 12,
When the polymer contains a plurality of structural units represented by (Iγ), the plurality of R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , Q ³ , X ³ and Y ³ may be the same or different. In some cases,
* represents a bond.
Group Iγ: -O-, -S- or a divalent heterocyclic group.
Group IIγ: -O-, -S-, -NR ¹⁹³ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ¹⁹³ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are each independently a hydrogen atom, a halogen atom, a nitrile group, a heterocyclic group, a hydrocarbon group having 1 to 30 carbon atoms, or the hydrocarbon group. Represents a group in which one or more methylene groups are replaced with a divalent group selected from the following group Iδ, provided that two or more methylene groups are divalent groups selected from the following group Iδ ^{When substituted with _ _ _} is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a mercapto group, an isocyanate group, or May be substituted with carboxyl group,
Q ⁴ represents -O-, -CO-O- or -O-CO-,
Y ⁴ is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-divalent a heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or one or more methylene groups in the hydrocarbon group has been replaced with a divalent group selected from the following Group IIδ group, provided that when two or more methylene groups are replaced with divalent groups selected from Group IIδ below, the divalent groups are not adjacent, and Y ⁴ is One or more of the hydrogen atoms is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, May be substituted with vinyl group, mercapto group, isocyanate group or carboxyl group,
n represents an integer from 1 to 12,
When the polymer contains a plurality of structural units represented by (Iδ), the plurality of R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , Q ⁴ and Y ⁴ may be the same. , may be different,
* represents a bond.
Group Iδ: -O-, -S- or a divalent heterocyclic group.
Group II δ: -O-, -S-, -NR ¹⁹⁴ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ¹⁹⁴ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ²¹ represents a hydrogen atom or a methyl group,
X ¹¹ represents a single bond or -S-,
Z ¹ is a divalent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or a divalent group in which one or more methylene groups in the hydrocarbon group are selected from the group IIIα below. However, when two or more methylene groups are replaced with a divalent group selected from the following group IIIα, the divalent groups are not adjacent to each other and are represented by Z ¹ . One or more hydrogen atoms in the group include a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group. , may be substituted with an epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
When the polymer contains a plurality of structural units represented by (IIα), the plurality of R ²¹ , X ¹¹ and Z ¹ may be the same or different,
* represents a bond.
Group IIIα: -O-, -S-, -NR ²⁵¹ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ²⁵¹ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ²² represents a hydrogen atom or a methyl group,
X ¹² represents a single bond or -S-,
Z ² is a divalent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or a divalent group in which one or more methylene groups in the hydrocarbon group are selected from Group IIIβ below. However, when two or more methylene groups are replaced with a divalent group selected from Group IIIβ below, the divalent groups are not adjacent and are represented by Z ² . One or more hydrogen atoms in the group include a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group. , may be substituted with an epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
When the polymer contains a plurality of structural units represented by (IIβ), the plurality of R ²² , X ¹² and Z ² may be the same or different,
* represents a bond.
Group IIIβ: -O-, -S-, -NR ²⁵² -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ²⁵² represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ²³ represents a hydrogen atom or a methyl group,
X ¹³ represents a single bond or -S-,
Z ³ is a divalent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or a divalent group in which one or more methylene groups in the hydrocarbon group are selected from Group IIIγ below. However, when two or more methylene groups are replaced with a divalent group selected from Group IIIγ below, the divalent groups are not adjacent and are represented by Z ³ . One or more hydrogen atoms in the group include a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group. , may be substituted with an epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
When the polymer contains a plurality of structural units represented by (IIγ), the plurality of R ²³ , X ¹³ and Z ³ may be the same or different,
* represents a bond.
Group IIIγ: -O-, -S-, -NR ²⁵³ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ²⁵³ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

[2]
The polymer according to [1], which has a structural unit represented by formula (Iα), (Iβ), (Iγ) or (Iδ) in the main chain of the polymer.

[3]
It has a structural unit represented by formula (Iα), a structural unit represented by formula (Iβ), or a structural unit represented by formula (Iγ),
The group represented by Y ¹ in formula (Iα) is -O-, -O-CO-, -CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n - O-, n is an integer from 1 to 12,
The group represented by Y ² in formula (Iβ) is -O-, -O-CO-, -CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n - O-, n is an integer from 1 to 12,
The group represented by Y ³ in formula (Iγ) is -O-, -O-CO-, -CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n - The polymer according to [1] or [2], which is O- and n is an integer of 1 to 12.

[4]
The groups represented by R ² , R ³ and R ⁴ in the above formula (Iα) are each independently a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms,
The groups represented by R ⁶ , R ⁷ and R ⁸ in the above formula (Iβ) are each independently a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms,
The groups represented by R ¹⁰ , R ¹¹ and R ¹² in the above formula (Iγ) are each independently a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms,
The groups represented by R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ in the above formula (Iδ) are each independently a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms, The polymer according to any one of [1] to [3].

[5]
The total proportion of the structural unit represented by formula (Iα), the structural unit represented by formula (Iβ), the structural unit represented by formula (Iγ), and the structural unit represented by formula (Iδ) is The polymer according to any one of [1] to [4], which is 20 to 90% by mass based on the total weight of the polymer.

[6]
The group represented by X ¹¹ in formula (IIα) is -S-,
The group represented by X ¹² in formula (IIβ) is -S-,
The group represented by X ¹³ in formula (IIγ) is -S-,
The polymer according to any one of [1] to [5].

[7]
The group represented by Z ¹ in the above formula (IIα) is a hydrocarbon group having 1 to 10 carbon atoms, or one or more methylene groups of the hydrocarbon group is -O-, -OCO-, - A group substituted with COO-, -S- or -O-CO-O-,
The group represented by Z ¹ in the above formula (IIβ) is a hydrocarbon group having 1 to 10 carbon atoms, or one or more methylene groups of the hydrocarbon group is -O-, -OCO-, - A group substituted with COO-, -S- or -O-CO-O-,
The group represented by Z ¹ in the above formula (IIγ) is a hydrocarbon group having 1 to 10 carbon atoms, or one or more methylene groups of the hydrocarbon group is -O-, -OCO-, - A group substituted with COO-, -S- or -O-CO-O-,
The polymer according to any one of [1] to [6].
[8]
The polymer according to any one of [1] to [7], which has a weight average molecular weight of 1,000 to 500,000.

[9]
The polymer according to any one of [1] to [8], which has a polydispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of 1 to 2.5.

[10]
A photodegradable resin containing the polymer according to any one of [1] to [9].

[11]
A composition containing the polymer according to any one of [1] to [9].

[12]
The easily dismantled adhesive according to any one of [1] to [9].

[13]
A pattern forming agent containing the polymer according to any one of [1] to [9].

[14]
A photolatent catalyst containing the polymer according to any one of [1] to [9] and an active species.

[15]
A method for decomposing a photodegradable resin, comprising the step of irradiating the photodegradable resin according to [10] with light.

According to the present invention, it is possible to provide a polymer that is highly degradable to specific light such as UV light and has a large effect of reducing the weight average molecular weight by photodecomposition. By using the polymer of the present invention, it is possible to obtain excellent photo-disassembly adhesives, pattern-forming agents, and photo-latent catalysts.

Hereinafter, preferred embodiments of the present invention will be described in detail.

<Polymer>
The polymer of the present invention comprises a structural unit represented by the above formula (Iα), a structural unit represented by the above formula (Iβ), a structural unit represented by the above formula (Iγ), and a structural unit represented by the above formula (Iδ). It has one or more types of structural units selected from the group consisting of the represented structural units. By having such a structural unit and a structural unit selected from formulas (IIα), (IIβ), and (IIγ) described below, the polymer of the present invention has the advantageous effect of being highly degradable to specific light. play.

R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R in the above formulas (Iα), (Iβ), (Iγ) and (Iδ) Examples of the halogen atoms represented by ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ include fluorine, chlorine, bromine and iodine.
^A group represented by ^R2 , ^R3 , ^R4 , ^R6 , ^R7 , ^R8 , ^R10 , ^R11 , R12, ^R13 , ^R14 , ^R15 , ^R16 , ^R17 and ^R18 , The same explanation also applies to the halogen atoms that may substitute hydrogen atoms in the groups represented by Y ¹ , Y ² , Y ³ and Y ⁴ .

R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R in the above formulas (Iα), (Iβ), (Iγ) and (Iδ) The hydrocarbon groups having 1 to 30 carbon atoms represented by R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹¹ , R ¹⁹² , R ¹⁹³ and R ¹⁹⁴ are not particularly limited; , for example, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a cycloalkylalkyl group having 4 to 30 carbon atoms, and a cycloalkylalkyl group having 6 to 30 carbon atoms. Examples include an aryl group having 30 carbon atoms and an arylalkyl group having 7 to 30 carbon atoms. When the hydrocarbon group having 1 to 30 carbon atoms has a substituent, the total number of carbon atoms is 1 to 30.
^A group represented by ^R2 , ^R3 , ^R4 , ^R6 , ^R7 , ^R8 , ^R10 , ^R11 , R12, ^R13 , ^R14 , ^R15 , ^R16 , ^R17 and ^R18 , The same explanation also applies to hydrocarbon groups having 1 to 30 carbon atoms that may substitute hydrogen atoms in the groups represented by Y ¹ , Y ² , Y ³ and Y ⁴ .

The alkyl group having 1 to 30 carbon atoms may be linear or branched. Straight chain alkyl groups include, for example, methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl and icosyl. Examples of the branched alkyl group include isopropyl, isobutyl, s-butyl, t-butyl, isoamyl, t-amyl, isooctyl, 2-ethylhexyl, t-octyl, isononyl, and isodecyl. In the present invention, linear polymers are preferred because raw materials are easily available and the polymer has high stability. Furthermore, since the polymer has better photodegradability, an alkyl group having 1 to 10 carbon atoms is preferable, and an alkyl group having 1 to 4 carbon atoms is more preferable.

The above alkenyl group having 2 to 30 carbon atoms may be chain-like or cyclic. When the alkenyl group is chain-like, it may be a terminal alkenyl group having an unsaturated bond at the end, or an internal alkenyl group having an internal unsaturated bond. Examples of the terminal alkenyl group having 2 to 30 carbon atoms include vinyl, 2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl. Examples of internal alkenyl groups include 2-butenyl, 3-pentenyl, 2-hexenyl, 3-hexenyl, 2-heptenyl, 3-heptenyl, 4-heptenyl, 3-octenyl, 3-nonenyl, 4-decenyl, 3- Examples include undecenyl and 4-dodecenyl. Examples of the cyclic alkenyl group include 3-cyclohexenyl, 2,5-cyclohexadienyl-1-methyl, and 4,8,12-tetradecatrienylallyl. In the present invention, alkenyl groups having 2 to 10 carbon atoms are preferred because the polymer has even better photodegradability.

The above-mentioned cycloalkyl group having 3 to 30 carbon atoms means a saturated monocyclic or saturated polycyclic alkyl group having 3 to 30 carbon atoms in total. Examples of the saturated monocyclic alkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl. Examples of the saturated polycyclic alkyl group include adamantyl, decahydronaphthyl, octahydropentalene, bicyclo[1.1.1]pentanyl, and tetradecahydroanthracenyl. In the present invention, a cycloalkyl group having 3 to 10 carbon atoms is preferred because the polymer has better photodegradability.

The above-mentioned cycloalkylalkyl group having 4 to 30 carbon atoms means a group in which a hydrogen atom of an alkyl group is substituted with a cycloalkyl group and having a total of 4 to 30 carbon atoms. The cycloalkyl group in the cycloalkylalkyl group may be monocyclic or polycyclic. Furthermore, the methylene group of the alkyl group in the cycloalkylalkyl group may be replaced with -CH=CH-.
Examples of the cycloalkylalkyl group having 4 to 30 carbon atoms in which the cycloalkyl group is a monocyclic ring include cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, cyclononylmethyl, and cycloalkylmethyl. Cycloalkylmethyl such as decylmethyl; Cycloalkylethyl; cycloalkylpropyl such as 3-cyclobutylpropyl, 3-cyclopentylpropyl, 3-cyclohexylpropyl, 3-cycloheptylpropyl, 3-cyclooctylpropyl, 3-cyclononylpropyl and 3-cyclodecylpropyl; 4 Examples include cycloalkylbutyl such as -cyclobutylbutyl, 4-cyclopentylbutyl, 4-cyclohexylbutyl, 4-cycloheptylbutyl, 4-cyclooctylbutyl, 4-cyclononylbutyl, and 4-cyclodecylbutyl. Examples of cycloalkylalkyl groups having 4 to 20 carbon atoms in which the cycloalkyl group is a polycyclic group include bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, and bicyclo[2.1.0]pentyl. , bicyclo[3.1.0]hexyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.0]hexyl, bicyclo[4.1.0]heptyl, bicyclo[3.2.0]heptyl , bicyclo[3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[5.1.0]octyl, bicyclo[4.2.0]octyl, bicyclo[4.1.1]octyl , bicyclo[3.3.0]octyl, bicyclo[3.2.1]octyl, bicyclo[2.2.2]octyl, spiro[4,4]nonanyl, spiro[4,5]decanyl, decalin, tri Examples include cyclodecanyl, tetracyclododecanyl, cedrol, cyclododecanyl 3-3-adamantylpropyl and decahydronaphthylpropyl.
In the present invention, a cycloalkylalkyl group having 4 to 10 carbon atoms is preferred because the polymer has better photodegradability.

The above aryl group having 6 to 30 carbon atoms may have a monocyclic structure or a condensed ring structure. Furthermore, the above aryl group may be one in which an aryl group with a monocyclic structure and an aryl group with a monocyclic structure are connected, or an aryl group with a monocyclic structure and an aryl group in a condensed structure are connected. Alternatively, an aryl group having a condensed structure and an aryl group having a condensed structure may be connected. Examples of the aryl group having a monocyclic structure include phenyl and biphenylyl. Examples of the aryl group having a condensed ring structure include naphthyl, anthryl, and phenanthrenyl. One or more hydrogen atoms of the aryl group having 6 to 30 carbon atoms may be substituted with a substituent. Examples of the substituent include the above-mentioned alkyl group, the above-mentioned alkenyl group, carboxyl group, and halogen atom. Examples of the aryl group having 6 to 30 carbon atoms having a substituent include tolyl, xylyl, ethylphenyl, 4-chlorophenyl, 4-carboxylphenyl, 4-vinylphenyl, 4-methylphenyl, 2,4,6-trimethyl Examples include substituted aryl groups with a monocyclic structure such as phenyl. In the present invention, an aryl group having 6 to 10 carbon atoms is preferable because the polymer has better photodegradability.

The above arylalkyl group having 7 to 30 carbon atoms means a group in which one or more hydrogen atoms of an alkyl group are substituted with the above aryl group. Examples of the arylalkyl group having 7 to 30 carbon atoms include benzyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, α-dimethylbenzyl, 2-phenylethyl, 2-phenylpropyl, 3-phenylpropyl, Mention may be made of phenylalkyl such as diphenylmethyl, triphenylmethyl and triphenylpropyl; and naphthylalkyl such as naphthylpropyl. In the present invention, an arylalkyl group having 7 to 10 carbon atoms is preferred because the polymer has better photodegradability.

R ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ⁸ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R in the above formulas (Iα), (Iβ), (Iγ) and (Iδ) The heterocycle represented by ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ may be a monocyclic ring or may have a condensed ring structure. Furthermore, one or more hydrogen atoms of the heterocyclic group may be substituted with an alkyl group having 1 to 6 carbon atoms. Furthermore, the heterocyclic group may form a condensed ring structure heterocyclic group by bonding via an alkylene group having 1 to 6 carbon atoms. Examples of the monocyclic heterocyclic group include pyrrolyl, pyridyl, pyridylethyl, pyrimidyl, pyridazyl, piperazyl, piperidyl, pyranyl, pyranylethyl, pyrazolyl, triazyl, triazylmethyl, pyrrolidyl, imidazolyl, triazolyl, furyl, furanyl, thienyl, Thiophenyl, thiadiazolyl, thiazolyl, oxazolyl, isothiazolyl, isoxazolyl, eurolidyl, morpholinyl, thiomorpholinyl, 2-pyrrolidinone-1-yl, 2-piperidon-1-yl, 2,4-dioxyimidazolidin-3-yl and Examples include 2,4-dioxyoxazolidin-3-yl. Examples of the heterocyclic group having a condensed ring structure include quinolyl, isoquinolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, and indolyl.
^A group represented by ^R2 , ^R3 , ^R4 , ^R6 , ^R7 , ^R8 , ^R10 , ^R11 , R12, ^R13 , ^R14 , ^R15 , ^R16 , ^R17 and ^R18 , The same explanation also applies to the heterocyclic groups that may substitute the hydrogen atoms of the groups represented by Y ¹ , Y ² , Y ³ and Y ⁴ .

Specific examples of the heterocyclic group include, but are not particularly limited to, groups having the following structures.

(In the above formula, R each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, Z each independently represents a direct bond or an alkylene group having 1 to 6 carbon atoms, * represents a bond.)

Examples of the alkyl group having 1 to 6 carbon atoms include those exemplified above as alkyl groups having 1 to 30 carbon atoms.

Examples of the alkylene group having 1 to 6 carbon atoms include methylene, ethylene, propylene, butylene, pentylene, hexylene, and the like.

The divalent hydrocarbon groups having 1 to 30 carbon atoms represented by Y ¹ , Y ² , Y ³ and Y ⁴ in the above formulas (Iα), (Iβ), (Iγ) and (Iδ) are: Examples include divalent groups obtained by removing one hydrogen atom from the above-mentioned hydrocarbon groups having 1 to 30 carbon atoms.

Divalent heterocyclic groups represented by Y ¹ , Y ² , Y ³ and Y ⁴ in the above formulas (Iα), (Iβ), (Iγ) and (Iδ), and divalent heterocyclic groups in Groups I and II Examples of the heterocyclic group include divalent groups obtained by removing one hydrogen atom from the above-mentioned heterocyclic group.

Among the structural units represented by the above formulas (Iα), (Iβ), (Iγ) and (Iδ), the polymer of the present invention has a structural unit represented by (Iα), and (Iβ). It is preferable to contain at least one selected from the group consisting of a structural unit and a structural unit represented by (Iγ). This is because the polymer becomes even more excellent in photodegradability. The polymer of the present invention more preferably has a structural unit represented by (Iα) or (Iβ), and even more preferably has a structural unit represented by (Iα). This is because the production of the polymer becomes easy and the polymer has excellent storage stability.

When the polymer of the present invention has a structural unit represented by formula (Iα), when the group represented by R ¹ in formula (Iα) is a hydrogen atom, the polymer with excellent storage stability can be obtained. It is preferable because it can be obtained. It is preferable that the group represented by R ¹ in formula (Iα) is a methyl group because the photodegradable resin and composition after photodecomposition of the polymer will be less colored.
The groups represented by R ² to R ⁴ in the above formula (Iα) each independently represent a hydrogen atom; fluorine; a perfluoroalkyl group such as a trifluoromethyl group; one or more of the methylene groups is -O-; A substituted alkyl group having 1 to 4 carbon atoms; or preferably a nitrile group, more preferably a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkoxy group such as a trifluoromethoxy group It is preferably a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms. This is because the polymer can be easily manufactured and has excellent storage stability.
When the group represented by X ¹ in the above formula (Iα) is a single bond, it is preferable because the storage stability of the polymer is excellent. When the group represented by X ¹ in the above formula (Iα) is a methylene group, it is preferable because the photodegradable resin and composition are less colored after photodecomposition of the polymer.
The group represented by Y ¹ in the above formula (Iα) increases the stability of the polymer and makes the polymer excellent in photodegradability by specific light. It is preferably O-CO-, -CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, and -O-CO- or -CO-O- It is more preferable that there be. n represents an integer from 1 to 12.

When the polymer of the present invention has a structural unit represented by formula (Iβ), when the group represented by R ⁵ in formula (Iβ) is a hydrogen atom, the storage stability of the polymer is excellent. It is preferable because it becomes a product. When the group represented by R ⁵ in the above formula (Iβ) is a methyl group, it is preferable because the photodegradable resin and composition are less colored after photodecomposition of the polymer.
The groups represented by R ⁶ to R ⁸ in the above formula (Iβ) each independently represent a hydrogen atom; fluorine; a perfluoroalkyl group such as a trifluoromethyl group; one or more of the methylene groups is -O-; A substituted alkyl group having 1 to 4 carbon atoms; or preferably a nitrile group, more preferably a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkoxy group such as a trifluoromethoxy group It is preferably a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms. This is because the polymer can be easily manufactured and has excellent storage stability. In the polymer of the present invention, R ⁷ is preferably an alkoxy group having 1 to 4 carbon atoms.
When the group represented by X ² in the above formula (Iβ) is a single bond, it is preferable because the polymer has excellent storage stability. When the group represented by X ² in the above formula (Iβ) is a methylene group, it is preferable because the photodegradable resin and composition are less colored after photodecomposition of the polymer.
The group represented by Y ² in the above formula (Iα) increases the stability of the polymer and makes the polymer excellent in photodegradability by specific light. It is preferably O-CO-, -CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, and -O-CO- or -CO-O- It is more preferable that there be. n represents an integer from 1 to 12.

When the polymer of the present invention has a structural unit represented by formula (Iγ), when the group represented by R ⁹ in formula (Iγ) is a hydrogen atom, the polymer has excellent storage stability. It is preferable because it becomes a product. It is preferable that the group represented by R ⁹ in the above formula (Iγ) is a methyl group, since the photodegradable resin and the composition are less colored after photodecomposition of the polymer.
In the above formula (Iδ), the groups represented by R ¹⁰ to R ¹² each independently represent a hydrogen atom; fluorine; a perfluoroalkyl group such as a trifluoromethyl group; and one or more of the methylene groups -O- A substituted alkyl group having 1 to 4 carbon atoms; or preferably a nitrile group, more preferably a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkoxy group such as a trifluoromethoxy group It is preferably a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms. This is because the polymer can be easily manufactured and has excellent storage stability.
When the group represented by X ³ in the above formula (Iγ) is a single bond, it is preferable because the polymer has excellent storage stability. It is preferable that the group represented by X ³ in the above formula (Iγ) is a methylene group because the photodegradable resin and the composition are less colored after photodecomposition of the polymer.
The group represented by Y ³ in the above formula (Iα) increases the stability of the polymer and makes the polymer excellent in photodegradability by specific light. It is preferably O-CO-, -CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, and -O-CO- or -CO-O- It is more preferable that there be. n represents an integer from 1 to 12.

When the polymer of the present invention has a structural unit represented by formula (Iδ), the groups represented by R ¹³ to R ¹⁸ in formula (Iδ) each independently represent a hydrogen atom; fluorine; A perfluoroalkyl group such as a methyl group; an alkyl group having 1 to 4 carbon atoms in which one or more of the methylene groups is replaced with -O-; or a nitrile group, preferably a hydrogen atom or a carbon atom number 1 to 4 It is more preferably an alkoxy group of 4 or a perfluoroalkoxy group such as a trifluoromethoxy group, even more preferably a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms, and particularly preferably a hydrogen atom. . This is because the polymer can be easily manufactured and has excellent storage stability.
The group represented by Y ⁴ in the above formula (Iδ) increases the stability of the polymer and makes the polymer excellent in photodegradability by specific light. It is preferably O-CO-, -CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, and -O-CO- or -CO-O- It is more preferable that there be. n represents an integer from 1 to 12.

The total proportion of the structural units represented by formulas (Iα), (Iβ), (Iγ) and (Iδ) in the polymer of the present invention is preferably 20 to 90% by mass.

The polymer of the present invention is one type selected from the group consisting of a structural unit represented by the above formula (IIα), a structural unit represented by the above formula (IIβ), and a structural unit represented by the above formula (IIγ). It has the above structural units. It is said that by having such a structural unit and a structural unit selected from the aforementioned formulas (Iα), (Iβ), (Iγ) and (Iδ), the polymer of the present invention has high degradability against specific light. have a beneficial effect.

Regarding the hydrocarbon groups having 1 to 30 carbon atoms represented by R ²⁵¹ , R ²⁵² and R ²⁵³ in the above formulas (IIα), (IIβ) and (IIγ), the above-mentioned hydrocarbon groups having 1 to 30 carbon atoms The same explanation as for hydrogen groups applies.

Regarding the divalent hydrocarbon groups having 1 to 30 carbon atoms represented by Z ¹ , Z ² and Z ³ in the above formulas (IIα), (IIβ) and (IIγ), the above-mentioned divalent hydrocarbon groups having 1 to 30 carbon atoms The same explanation as for the divalent hydrocarbon group of 30 applies.
Regarding the divalent heterocyclic groups represented by Z ¹ , Z ² and Z ³ in the above formulas (IIα), (IIβ) and (IIγ), and the divalent heterocyclic group in Group III, the above-mentioned 2 The same explanations as for valent heterocyclic groups apply.
Regarding the halogen atom, heterocyclic group and hydrocarbon group having 1 to 30 carbon atoms that may be substituted for the groups represented by Z ¹ , Z ² and Z ³ , the halogen atom, heterocyclic group and carbon atom described above The same explanations as for the hydrocarbon groups of numbers 1 to 30 apply.

Among the structural units represented by the above formulas (IIα), (IIβ) and (IIγ), polymers having the structural unit represented by the formula (IIα) or (IIβ) are easy to produce and easy to store. It is preferable because it has excellent stability.

When the polymer of the present invention has a structural unit represented by the above formula (IIα), the group represented by X ¹¹ in the formula (IIα) is preferably -S-. This is because the polymer has excellent solvent solubility and processability.
The group represented by Z ¹ in the above formula (IIα) is a hydrocarbon group having 1 to 30 carbon atoms or A group in which one or more methylene groups of the hydrocarbon group is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O- is preferable, and has 1 to 1 carbon atoms. 10 hydrocarbon groups or a group in which one or more methylene groups of the hydrocarbon group is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O- is more preferred. Preferably, a group in which one methylene group of a hydrocarbon group having 1 to 10 carbon atoms is substituted with -S- is more preferable. The hydrocarbon group having 1 to 10 carbon atoms is preferably an alkylene group having 1 to 10 carbon atoms or a phenylalkylene group having 7 to 10 carbon atoms. The alkylene group having 1 to 10 carbon atoms is preferably linear. A group in which one or more methylene groups of a hydrocarbon group having 1 to 30 carbon atoms is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O-, The terminal methylene group of the hydrocarbon group is preferably substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O-.
The group represented by R ²¹ in the above formula (IIα) is preferably a hydrogen atom because it has excellent reactivity during polymer preparation.

When the polymer of the present invention has a structural unit represented by the above formula (IIβ), X ¹² in the formula (IIβ) is preferably -S-. This is because the polymer has excellent solvent solubility and processability.
The group represented by Z ² in the above formula (IIβ) is a hydrocarbon group having 1 to 30 carbon atoms or A group in which one or more methylene groups of the hydrocarbon group is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O- is preferable, and has 1 to 1 carbon atoms. 10 hydrocarbon groups or a group in which one or more methylene groups of the hydrocarbon group is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O- is more preferred. Preferably, a group in which one methylene group of a hydrocarbon group having 1 to 10 carbon atoms is substituted with -S- is more preferable. The hydrocarbon group having 1 to 10 carbon atoms is preferably an alkylene group having 1 to 10 carbon atoms or a phenylalkylene group having 7 to 10 carbon atoms. The alkylene group having 1 to 10 carbon atoms is preferably linear. A group in which one or more methylene groups of a hydrocarbon group having 1 to 30 carbon atoms is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O-, The terminal methylene group of the hydrocarbon group is preferably substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O-.
The group represented by R ²² in the above formula (IIβ) is preferably a hydrogen atom because it has excellent reactivity during polymer preparation.

When the polymer of the present invention has a structural unit represented by the above formula (IIγ), X ¹³ in the formula (IIγ) is preferably -S-. This is because the polymer has excellent solvent solubility and processability.
The group represented by Z ³ in the above formula (IIγ) is a hydrocarbon group having 1 to 30 carbon atoms or A group in which one or more methylene groups of the hydrocarbon group is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O- is preferable, and has 1 to 1 carbon atoms. 10 hydrocarbon groups or a group in which one or more methylene groups of the hydrocarbon group is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O- is more preferred. Preferably, a group in which one methylene group of a hydrocarbon group having 1 to 10 carbon atoms is substituted with -S- is more preferable. The hydrocarbon group having 1 to 10 carbon atoms is preferably an alkylene group having 1 to 10 carbon atoms or a phenylalkylene group having 7 to 10 carbon atoms. The alkylene group having 1 to 10 carbon atoms is preferably linear. A group in which one or more methylene groups of a hydrocarbon group having 1 to 30 carbon atoms is substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O-, The terminal methylene group of the hydrocarbon group is preferably substituted with -O-, -OCO-, -COO-, -S- or -O-CO-O-.
The group represented by R ²³ in the above formula (IIγ) is preferably a hydrogen atom because it has excellent reactivity during polymer preparation.

The total proportion of the structural units represented by the above formulas (IIα), (IIβ) and (IIγ) in the polymer of the present invention is not particularly limited, but it is preferable that the total proportion is 10 to 80% by mass. , is preferable because it has excellent storage stability in the visible light region.

The polymer of the present invention preferably has a structural unit represented by the above formula (Iα), (Iβ) or (Iγ) in its main chain because the molecular weight of the polymer is efficiently reduced by photolysis. .

The polymer of the present invention preferably has a weight average molecular weight of 1,000 to 500,000 because properties such as solvent solubility, melting point, and mechanical strength change significantly before and after photolysis. From this point of view, those with a molecular weight of 5,000 to 100,000 are particularly preferred.

The polydispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the polymer of the present invention is preferably 1 to 2.5, particularly preferably 1 to 2.0. This is because it becomes easier to control the photodegradability of the polymer.

The number average molecular weight and weight average molecular weight of the polymer can be determined as standard polystyrene equivalent values by gel permeation chromatography (GPC).
The above number average molecular weight Mn and weight average molecular weight Mw are, for example, using GPC (LC-2000plus series) manufactured by JASCO Corporation, using tetrahydrofuran as the elution solvent, and using polystyrene standards for the calibration curve as Mw 1110000, 707000, 397000, and 189000. , 98900, 37200, 13700, 9490, 5430, 3120, 1010, 589 (TSKgel standard polystyrene manufactured by Tosoh Corporation), and the measurement columns were KF-804, KF-803, KF-802 (manufactured by Showa Denko Corporation). ) can be obtained by measuring.
Further, the measurement temperature can be 40° C., and the flow rate can be 1.0 mL/min.

The method for producing the polymer of the present invention is not limited, but for example, a bifunctional di(meth)acrylate having an o-nitrobenzyl group or coumarin and a bifunctional dithiol compound or a base active species such as potassium tert-butoxide as a monomer can be used. It can be produced by stirring in the presence of

<Photodegradable resin>
The polymer of the present invention has excellent photodegradability and is therefore useful as a photodegradable resin. Photodegradable resin means a polymer that is easily decomposed by active energy rays such as visible light, ultraviolet rays, X-rays, electron beams, and high frequency waves. Polymers that decompose only with visible light are not preferred because they have poor storage stability, and photodegradable resins that decompose with ultraviolet light are preferred because they are easy to handle.

In the decomposed resin of the present invention, the polymer has structural units selected from formulas (Iα), (Iβ), (Iγ), and (Iδ), and structural units selected from formulas (IIα), (IIβ), and (IIγ). By having this, it becomes easily decomposed by various active energy rays.

When the photodegradable resin is decomposed by ultraviolet rays, the preferred irradiation amount is 0.1 to 100 J/cm ² , more preferably 0.5 to 10 J/cm ² . A photodegradable resin that decomposes at the above-mentioned irradiation dose has a good balance between storage stability and photodegradability and can be used in a wide range of applications.

<Composition>
The composition of the present invention only needs to contain the above polymer, and there is no particular restriction on the content of the polymer in the composition. The content of the polymer in the composition of the present invention is determined because a composition containing 50 parts by mass or more in 100 parts by mass of components having a weight average molecular weight of 1,000 or more has excellent photodegradability. preferable.

In addition, the composition of the present invention may optionally contain a polymerizable compound, a polymerization initiator, a colorant, an inorganic compound, a latent additive, an organic polymer, a chain transfer agent, a sensitizer, a surfactant, Silane coupling agent, melamine compound, thermal polymerization inhibitor; plasticizer; adhesion promoter; filler; antifoaming agent; leveling agent; surface conditioner; antioxidant; ultraviolet absorber; dispersion aid; anti-aggregation agent; catalyst Customary additives such as effect promoters; crosslinking agents; thickeners can be added.

The composition of the present invention can be used in a wide range of applications, including photo-disassembly adhesives, pattern-forming agents, photo-latent catalysts, recording media, liquid crystal display devices, wiring boards, ink compositions, and dust-proof films. As for product uses, photo-disassembly adhesives, pattern-forming agents, and photo-latent catalysts are particularly preferred.

<Lightly removable adhesive>
The light-disassembly adhesive described above contains the polymer of the present invention. By using a light-disassembling adhesive, the two types of members can be bonded together by irradiating the light-disassembly adhesive layer with a specific active energy ray, which causes the adhesive to decompose. can be separated. A light-disassembleable adhesive that is decomposed by ultraviolet rays is preferred because it is easy to irradiate with light. In addition, since it transmits light, it is particularly preferable to use it for adhering adhered members in which one or more of the two types of members is transparent.
Additives similar to those of the composition of the present invention can be appropriately added to the light-disassembly adhesive.

<Pattern forming agent>
The pattern forming agent of the present invention contains the polymer of the present invention. The pattern forming agent of the present invention has photolithographic properties, and specifically, by irradiating light through a mask and developing with a developer, a pattern with a width of 1,000 μm or less can be formed by ±10 μm. It can be reproducibly formed with an accuracy within %. The pattern forming agent of the present invention is useful, for example, in pattern formation of various electronic devices. By using the pattern forming agent of the present invention, there is an advantage that no acid or acid generator remains in the pattern portion, compared to a conventional method using an acid generator. A pattern forming agent that is decomposed by ultraviolet rays is preferable because the light irradiation operation is easy. Additives similar to those in the composition of the present invention can be appropriately added to the pattern forming agent.

<Photolatent catalyst>
The photolatent catalyst of the present invention contains the polymer of the present invention and an active species. A photolatent catalyst is a catalyst that can provide active species such as acids and bases by irradiation with specific active energy rays. The photolatent catalyst of the present invention includes active species in the polymer of the present invention, the photodegradable resin of the present invention, or the composition of the present invention, and the photodegradable resin is irradiated with a specific active energy ray. is decomposed and the active species contained within it are eluted into the system, allowing polymerization reactions to occur. Compared to conventional photopolymerization initiators, it is possible to encapsulate more active active species, so the photodegradable resin has the ability to polymerize instantly after photolysis, while maintaining excellent stability during storage. It has the advantage of being able to form a composition with

As the photodegradable resin used in the photolatent catalyst, those that are solid at room temperature (25°C) and normal pressure (atmospheric pressure) can be used without particular restriction, and those that are soluble in the composition containing active species can be used. It is preferable that the weight average molecular weight is 3,000 to 500,000 since it is small, and particularly preferable that it is 5,000 to 100,000 from the viewpoint of workability.

Methods for producing the photodegradable catalyst include, but are not particularly limited to, a method of kneading a photodegradable resin and an active species, a method of forming capsules in which an active species is coated with a photodegradable resin, and the like.

<Method for producing decomposed products of photodegradable resin>
A method for producing a decomposed product of a photodegradable resin according to the present invention will be explained. The photodegradable resin of the present invention or the composition of the present invention can be decomposed by irradiating it with active energy rays to produce decomposed products of lower molecular weight. The photodegradable resin of the present invention or the composition of the present invention may be directly irradiated with the active energy rays, or may be irradiated through a transparent material such as a base material. As the active energy ray, ultraviolet rays are preferred because of ease of handling.

EXAMPLES The present invention will be explained below using Examples, but the present invention is not limited to these Examples in any way.

<Synthesis of intermediate M-1>
Weigh out 9.4 g (0.047 mol) of 4-(hydroxymethyl)-2-methoxy-5-nitrophenol, 14 g (0.14 mol) of triethylamine, and 190 g of THF into a reaction flask equipped with a reflux tube to prepare a solution. did. This solution was cooled to 5° C., and a solution consisting of 13 g (0.14 mol) of acrylic acid chloride and 29 g of THF was added dropwise using a dropping funnel over 1 hour. During the dropwise addition, the temperature of the solution was kept below 10°C. The solution to which the solution was added dropwise was heated to room temperature (25° C.) and stirred for 3 hours to obtain a reaction solution. After the reaction was completed, the precipitate in the reaction solution was filtered, and the solvent of the filtrate was distilled off under reduced pressure. The residue was dissolved in 146 g of ethyl acetate and washed twice with 116 g of water. After the solvent in the organic layer was distilled off under reduced pressure and the solid content concentration was adjusted to 30%, n-hexane in an amount 5 times the weight of the solid content was added at room temperature. After continued stirring at room temperature for 1 hour, the solid was collected by filtration and dried to obtain 8.0 g (yield 55%) of the target product, M-1 shown below, in the form of a light yellow powder. The identification data ( ¹ H-NMR) of M-1 obtained is as follows.
[400MHz, CDCl ₃ ]: 8.02 (s, 1H, Ar-H), 7.14 (s, 1H, Ar-H), 6.65 (dd, 1H, -CH-CH ₂ ), 6. 52 (dd, 1H, -CH-CH ₂ ), 6.2-6.4 (m, 2H, -CH-CH ₂ ), 6.08 (dd, 1H, -CH-CH ₂ ), 5.95 (dd, 1H, -CH-CH ₂ ), 5.67 (s, 2H, -CH ₂ -O-), 3.93 (s, 3H, OMe)

<Synthesis of intermediate M-2>
Weigh out 1.3 g (6.7 mmol) of 7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one, 2.1 g (21 mmol) of triethylamine, and 26 g of THF into a reaction flask equipped with a reflux tube. , a solution was prepared. This solution was cooled to 5° C., and a solution consisting of 1.8 g (20 mmol) of acrylic acid chloride and 3.7 g of THF was added dropwise using a dropping funnel over 1 hour. During the dropwise addition, the temperature of the solution was kept below 10°C. The solution to which the solution was added dropwise was heated to room temperature (25° C.) and stirred for 1 hour, and then heated and refluxed for 3 hours to obtain a reaction solution. After the reaction was completed, the precipitate in the reaction solution was filtered, and the solvent of the filtrate was distilled off under reduced pressure. The residue was dissolved in 20 g of methylene chloride and washed twice with 10 g of water. The organic layer was solidified by distilling off the solvent under reduced pressure, washed with ethyl acetate, and dried to obtain 0.88 g (44% yield) of the target product, M2 shown below, in the form of a light orange powder. The identification data ( ¹ H-NMR) of M-2 obtained is as follows.
[400MHz, DMSO-d ₆ ]: 7.84 (d, 1H, Ar-H), 7.42 (d, 1H, Ar-H), 7.2-7.3 (m, 1H, Ar-H ), 6.5-6.7 (m, 1H, Ar-H), 6.0-6.5 (m, 6H, olefin), 5.51 (s, 2H, -CH ₂ -Ar)

Example 1
<Synthesis of polymer E-1>
Weigh out 6.0 g (20 mmol) of 4-(acryloyloxy)-5-methoxy-2-nitrobenzyl acrylate and 4.0 g (19 mmol) of 1,10-decanedithiol into a reaction flask equipped with a reflux tube, and add to 60 g of DMF. Dissolved and prepared a solution. 0.033 g (0.30 mmol) of potassium tert-butoxide was added to this solution, the temperature was raised to 50° C., and the mixture was stirred for 5 hours to obtain a reaction solution. After the reaction was completed, 120 g of methylene chloride was added to the reaction solution, and the mixture was washed three times with 120 g of water. After the solvent in the organic layer was distilled off under reduced pressure, the residue was cooled to 5° C., and 20 g of methanol was added to solidify it to obtain a solid. This solid was filtered while being washed with methanol, and the residue was dried to obtain 1.0 g of the desired polymer E-1 in the form of a pale yellow solid. E-1 had the following structural units. The molecular weight of E-1 was calculated by GPC measurement and was found to be Mw=6271 (Mw/Mn=1.54). ¹ H-NMR confirmed that E-1 had a structural unit represented by formula (Iβ) and a structural unit represented by formula (IIα). The proportion of the structural unit represented by formula (Iβ) in E-1 was 37% by mass.

Example 2
<Synthesis of polymer E-2>
・E-2
Weigh out 2.0 g (6.5 mmol) of 4-(acryloyloxy)-5-methoxy-2-nitrobenzyl acrylate and 1.0 g (6.7 mmol) of 1,6-hexanedithiol into a reaction flask equipped with a reflux tube. , was dissolved in 20 g of DMF to prepare a solution. 0.012 g (0.10 mmol) of potassium tert-butoxide was added to this solution, the temperature was raised to 40° C., and the mixture was stirred for 2.5 hours to obtain a reaction solution. After concentrating this reaction solution, 10 g of water was added to the residue and the precipitate was collected. Then, the precipitate was dried to obtain 2.6 g of the desired polymer E-2 in the form of a yellow viscous liquid. E-2 had the following structural units. The molecular weight of E-2 was calculated by GPC measurement and was found to be Mw=4926 (Mw/Mn=1.89). ¹ H-NMR confirmed that E-2 had a structural unit represented by formula (Iβ) and a structural unit represented by formula (IIα). The proportion of the structural unit represented by formula (Iβ) in E-2 was 41% by mass.

Example 3
<Synthesis of polymer E-3>
In a reaction flask equipped with a reflux tube, add 1.8 g (5.9 mmol) of 4-(acryloyloxy)-5-methoxy-2-nitrobenzyl acrylate and 1.0 g (5.9 mmol) of 1,4-benzenedimethanethiol. It was weighed out and dissolved in 19 g of DMF to prepare a solution. 0.010 g (0.088 mmol) of potassium tert-butoxide was added to this solution, and after stirring at room temperature (25°C) for 1 hour, the temperature was further raised to 55°C and stirred for an additional 6 hours to obtain a reaction solution. Ta. After concentrating the reaction solution, 28 g of methylene chloride was added, and the mixture was washed twice with 14 g of water. After the solvent of the organic layer was distilled off under reduced pressure, the residue was dissolved in 5.6 g of acetone, and 28 g of methanol was added dropwise to collect the precipitate. Next, the precipitate was dried to obtain 0.42 g of the desired polymer E-3 in the form of a yellow viscous liquid. E-3 had the following structural units. The molecular weight of E-3 was calculated by GPC measurement and was found to be Mw=6583 (Mw/Mn=1.33). ¹ H-NMR confirmed that E-3 had a structural unit represented by formula (Iβ) and a structural unit represented by formula (IIα). The proportion of the structural unit represented by formula (Iβ) in E-3 was 39% by mass.

Example 4
<Synthesis of polymer E-4>
In a reaction flask equipped with a reflux tube, 0.67 g (2.2 mmol) of (7-(acryloyloxy)-2-oxo-2H-chromen-4-yl)methyl acrylate and 0.34 g (2.2 mmol) of 1,6-hexanedithiol were added. .3 mmol) was weighed out and dissolved in 6.7 g of DMF to prepare a solution. 0.0037 g (0.033 mmol) of potassium tert-butoxide was added to this solution, and the mixture was stirred at room temperature (25°C) for 1 hour, then heated to 55°C and further stirred for 5 hours to obtain a reaction solution. After concentrating the reaction solution, 10 g of methylene chloride was added and washed twice with 10 g of water. After the solvent in the organic layer was distilled off under reduced pressure, the residue was dried to obtain 0.80 g of the desired polymer E-4 in the form of a brown viscous liquid. E-4 had the following structural units. The molecular weight of E-4 was calculated by GPC measurement and was found to be Mw=4140 (Mw/Mn=1.93). ¹ H-NMR confirmed that E-4 had a structural unit represented by formula (Iδ) and a structural unit represented by formula (IIα). The proportion of the structural unit represented by formula (Iδ) in E-4 was 52% by mass.

Example 5
<Synthesis of polymer E-5>
In a reaction flask equipped with a reflux tube, 0.49 g (1.6 mmol) of 4-(acryloyloxy)-5-methoxy-2-nitrobenzyl acrylate and 2-methyl-1,4-phenylene=bis(4-((4 - Weigh out 0.28 g (0.4 mmol) of acryloyloxybutoxy) carbonyloxy) benzoate and 0.43 g (2.1 mmol) of 1,10-decanedithiol and dissolve them in 10 g of DMF to prepare a solution. did. 0.0036 g (0.03 mmol) of potassium tert-butoxide was added to this solution, and the mixture was stirred at 30 to 35° C. for 7 hours to obtain a reaction solution. After the reaction was completed, 30 g of methylene chloride was added to the reaction solution, and the mixture was washed three times with 30 g of water. After distilling off the solvent in the organic layer under reduced pressure, 20 g of methanol was added to separate the viscous substance that precipitated, and the viscous substance was washed with 20 g of methanol, filtered, and dried to obtain the desired polymer E-5. 1.0 g of yellow viscous material was obtained. E-5 had the following structural units. The molecular weight of E-5 was calculated by GPC measurement and was found to be Mw=3420 (Mw/Mn=1.68). It was confirmed by ¹ H-NMR that E-5 has a constitutional unit represented by formula (Iβ) and a constitutional unit represented by formula (IIα). The proportion of the structural unit represented by formula (Iβ) in E-5 was 26% by mass.

Example 6
<Synthesis of polymer E-6>
In a reaction flask equipped with a reflux tube, 0.49 g (1.6 mmol) of 4-(acryloyloxy)-5-methoxy-2-nitrobenzyl acrylate, tricyclodecane dimethanol diacrylate (A-DCP, Shin Nakamura Chemical Co., Ltd.) Co., Ltd.) and 0.43 g (2.1 mmol) of 1,10-decanedithiol were weighed out and dissolved in 6 g of DMF to prepare a solution. 0.0036 g (0.03 mmol) of potassium tert-butoxide was added to this solution, and the mixture was stirred at 30 to 35° C. for 7 hours to obtain a reaction solution. After the reaction was completed, 30 g of methylene chloride was added to the reaction solution, and the mixture was washed three times with 30 g of water. After distilling off the solvent in the organic layer under reduced pressure, 20 g of methanol was added to separate the viscous substance that precipitated, and the viscous substance was washed with 20 g of methanol, filtered, and dried to obtain the desired polymer E. 0.28 g of -6 was obtained as a brown viscous substance. E-6 had the following structural units. The molecular weight of E-6 was calculated by GPC measurement and was found to be Mw=4176 (Mw/Mn=1.67). ¹ H-NMR confirmed that E-6 had a structural unit represented by formula (Iβ) and a structural unit represented by formula (IIα). The proportion of the structural unit represented by formula (Iβ) in E-6 was 30% by mass.

Example 7
<Synthesis of polymer E-7>
In a reaction flask equipped with a reflux tube, 0.49 g (1.6 mmol) of 4-(acryloyloxy)-5-methoxy-2-nitrobenzyl acrylate and neopentyl glycol dimethacrylate (NPG, manufactured by Shin Nakamura Chemical Industry Co., Ltd.) were added. 0.10 g (0.4 mmol) and 0.43 g (2.1 mmol) of 1,10-decanedithiol were weighed out and dissolved in 6 g of DMF to prepare a solution. 0.0036 g (0.03 mmol) of potassium tert-butoxide was added to this solution, and the mixture was stirred at 30 to 35° C. for 7 hours to obtain a reaction solution. After the reaction was completed, 30 g of methylene chloride was added to the reaction solution, and the mixture was washed three times with 30 g of water. After distilling off the solvent in the organic layer under reduced pressure, 20 g of methanol was added to separate the viscous substance that precipitated, and the viscous substance was washed with 20 g of methanol, filtered, and dried to obtain the desired polymer E. -7 was obtained as a pale yellow viscous substance in an amount of 0.68 g. E-7 had the following structural units. The molecular weight of E-7 was calculated by GPC measurement and was found to be Mw=4207 (Mw/Mn=1.63). ¹ H-NMR confirmed that E-7 had a structural unit represented by formula (Iβ) and a structural unit represented by formula (IIα). The proportion of the structural unit represented by formula (Iβ) in E-7 was 30% by mass.

Comparative example 1
<Synthesis of polymer R-1>
In a reaction flask equipped with a reflux tube, 0.61 g (2.0 mmol) of tricyclodecane dimethanol diacrylate (A-DCP, manufactured by Shin-Nakamura Chemical Co., Ltd.) and 0.43 g (2.0 mmol) of 1,10-decanedithiol were added. 1 mmol) was weighed out and dissolved in 6 g of DMF to prepare a solution. 0.0036 g (0.03 mmol) of potassium tert-butoxide was added to this solution, and the mixture was stirred at 30 to 35° C. for 7 hours to obtain a reaction solution. After the reaction was completed, 30 g of methylene chloride was added to the reaction solution, and the mixture was washed three times with 30 g of water. After distilling off the solvent in the organic layer under reduced pressure, 20 g of methanol was added to separate the viscous substance that precipitated, and the viscous substance was further washed with 20 g of methanol, filtered, and dried to obtain polymer R-1. 0.68 g of brown viscous material was obtained. R-2 had the following structural unit. When the molecular weight was calculated by GPC measurement, it was found that Mw=7541 (Mw/Mn=2.70).

(1) Molecular weight change test upon light irradiation Chloroform solutions (concentration: 1.0×10 ⁻² mol/L) of polymers E-1 to E-7 and polymer R-1 were prepared, respectively. The prepared solution was irradiated with ultraviolet rays of 1 J/cm ² or 10 J/cm ² using a high-pressure mercury lamp (20 mW/cm ² (@365 nm)). The weight average molecular weight (Mw) of the polymer after light irradiation was calculated by GPC measurement, and the Mw residual rate (%) of the polymer was calculated based on the formula below. The results are shown in Table 1 below.

Mw residual rate (%) = Mw after light irradiation/Mw before light irradiation x 100

As is clear from Table 1, the molecular weights of the polymers E-1 to E-7 of Examples 1 to 7 were significantly reduced by light irradiation. On the other hand, the molecular weight of the polymer R-1 of Comparative Example 1 hardly changed. This revealed that the polymer of the present invention is decomposed by light and its molecular weight changes. In addition, the polymers E-1 to E-7 of Examples 1 to 7 showed a decrease in molecular weight even at low irradiation doses. On the other hand, in the polymer R-1 of Comparative Example 1, in which no photolytic group was introduced, the molecular weight did not change at low irradiation doses. This also revealed that the polymer of the present invention is highly degradable to light.

(2) Test of change in substrate adhesion by light irradiation Polymer E-1 of Example 1 was placed on one surface of a glass substrate (Eagle XG manufactured by Corning) heated to 100° C., and the polymer was melted. A glass substrate was placed on the surface of the glass substrate on which Polymer E-1 was placed to prepare a substrate for evaluation. Visual observation of the evaluation board revealed that the two glass substrates were adhered via polymer E-1. The evaluation substrate was irradiated with ultraviolet light at 10 J/cm ^{2 using a high-pressure mercury lamp (20 mW/cm 2 (} @365 nm)). When the evaluation substrate was observed after being irradiated with light, it was found that part of the polymer had separated from the glass substrate. From this, it became clear that the polymer of Example 1 is a material whose adhesive strength decreases upon irradiation with light, and is useful as a light-disassembly adhesive.

(3) Thin film evaluation test A chloroform solution (concentration: 10% by mass) of polymer E-1 was prepared. The prepared chloroform solution was coated onto a glass substrate (Eagle XG manufactured by Corning) using a spin coater to a film thickness of about 1 μm, and then heated at 100° C. for 1 minute to dry the coated film. After the coating film was cooled to room temperature (25° C.), the cooled coating film was irradiated with 365 nm ultraviolet rays through a photomask (LINE/SPACE=50 μm/50 μm). A high-pressure mercury lamp (20 mW/cm ² (@365 nm)) was used for irradiation, and 10 J/cm ² was irradiated. Next, the glass substrate was immersed in acetone at 23°C for 1 minute, the solvent adhering to the glass substrate was removed using an air gun, and the glass substrate was dried at 100°C for 1 minute. When the pattern on the glass substrate after drying was observed with a laser microscope, it was found that the film in the exposed areas was developed, and the pattern was formed with the film in the unexposed areas intact. From this, it became clear that the polymer E-1 of Example 1 is useful as a positive pattern-forming material in which a pattern is created in the step of removing the exposed area with a developer.

(4) Photolatent catalyst test 1) 1.0 g of polymer E-1 and 1.0 g of m-xylylenediamine were dissolved in 5.0 mL of dichloromethane. After stirring at room temperature for 10 minutes, the mixture was distilled off under reduced pressure to obtain a pale yellow amorphous solid.
2) Preparation of composition A: The composition prepared in 1), 5.0 g of epoxy resin composition (EP-4100E (bisphenol A epoxy resin manufactured by ADEKA Co., Ltd.) and ED-523T (manufactured by ADEKA Co., Ltd.) Neopentyl glycol diglycidyl ether) (60/40 (mass ratio) mixture) was mixed with
3) Preparation of comparative composition B (comparative example): 5.0 g of the epoxy resin composition used in 2) and 1.0 g of m-xylylenediamine were mixed.
4) Results: Compositions A and B were left at room temperature, and when the state was checked after 24 hours, Composition B had solidified and lost its fluidity, but Composition A was no different from after preparation. However, it had fluidity and no changes were observed. When Composition A was coated on a glass substrate (Eagle XG manufactured by Corning) and irradiated with ultraviolet light at 5 J/cm ² using a high-pressure mercury lamp (20 mW/cm 2 (@365 nm)), the surface became free of tack. From this, by coating a reactive substance (catalyst) with the polymer E-1 of Example 1, the function (reactivity) of the reactive substance can be made latent, and its reactivity can be made latent by light irradiation. It was confirmed that the substance functions. From this, it is clear that the polymer E-1 of Example 1 can exhibit the function of a reactive substance by light and is useful as a photo-latenting agent.

(5) Photodegradability test using LED light source Chloroform solutions (3% by mass) of polymers E-1 to E-7 were each cast on a glass substrate (Eagle XG manufactured by Corning), dried at 100°C for 1 minute, A polymer membrane was prepared. A test piece with a part of the film masked was prepared and irradiated with light corresponding to 10 J/cm ² using an LED light source (365 nm, 20 mW). It was visually confirmed that the exposed surface of each test piece had become brittle. As a result of immersing the exposed test pieces in acetone, there was no change in the surface of the unexposed area of each test piece, and the test pieces were insoluble in acetone. A test piece was prepared using the same method for polymer R-1, and the same evaluation was carried out, but no embrittlement was observed on the surface of the exposed area, and the solubility in the solvent (acetone) was not observed in the exposed/unexposed area. There was no difference. From this, it became clear that the polymer of the present invention was photodegradable to the LED light source.

Claims (14)

Selected from the group consisting of a structural unit represented by the following formula (Iα), a structural unit represented by the formula (Iβ), a structural unit represented by the formula (Iγ), and a structural unit represented by the formula (Iδ) one or more types of structural units,
It has one or more structural units selected from the group consisting of a structural unit represented by the following formula (IIα), a structural unit represented by the formula (IIβ), and a structural unit represented by the formula (IIγ). ,
The total proportion of the structural unit represented by formula (Iα), the structural unit represented by formula (Iβ), the structural unit represented by formula (Iγ), and the structural unit represented by formula (Iδ) is 20 to 90% by weight of the polymer, based on the combined weight.

In the formula, R ¹ represents a hydrogen atom or a methyl group,
R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a halogen atom, a nitrile group, a heterocyclic group, a hydrocarbon group having 1 to 30 carbon atoms, or one of the methylene groups in the hydrocarbon group; Represents a group in which two or more of the methylene groups are replaced with a divalent group selected from the group Iα below, provided that when two or more methylene groups are replaced with a divalent group selected from the group Iα below, the two The valent groups are not adjacent to each other, and one or more hydrogen atoms in the groups represented by R ² , R ³ and R ⁴ are a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, or a halogen group. may be substituted with an atom, nitro group, cyano group, hydroxyl group, amino group, methacryloyl group, acryloyl group, epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
Q ¹ represents -O-, -CO-O- or -O-CO-,
X ¹ represents a single bond or a methylene group,
Y ¹ is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, 2 a valent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or one or more methylene groups in the hydrocarbon group is replaced with a divalent group selected from the following group IIα. However, when two or more methylene groups are replaced with divalent groups selected from Group IIα below, the divalent groups are not adjacent to ^{each other} , and One or more of the hydrogen atoms is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, May be substituted with vinyl group, mercapto group, isocyanate group or carboxyl group,
n represents an integer from 1 to 12,
When the polymer contains a plurality of structural units represented by (Iα), the plurality of R ¹ , R ² , R ³ , R ⁴ , Q ¹ , X ¹ and Y ¹ may be the same or different. In some cases,
* represents a bond.
Group Iα: -O-, -S- or divalent heterocyclic group.
Group IIα: -O-, -S-, -NR ¹⁹¹ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ¹⁹¹ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ⁵ represents a hydrogen atom or a methyl group,
R ⁶ , R ⁷ and R ⁸ each independently represent a hydrogen atom, a halogen atom, a nitrile group, a heterocyclic group, a hydrocarbon group having 1 to 30 carbon atoms, or one of the methylene groups in the hydrocarbon group; Represents a group in which two or more of the methylene groups are substituted with divalent groups selected from the following group Iβ, provided, however, that when two or more methylene groups are replaced with divalent groups selected from the following group Iβ, the two The valent groups are not adjacent to each other, and one or more hydrogen atoms in the groups represented by R ⁶ , R ⁷ and R ⁸ are a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, or a halogen group. may be substituted with an atom, nitro group, cyano group, hydroxyl group, amino group, methacryloyl group, acryloyl group, epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
Q ² represents -O-, -CO-O- or -O-CO-,
X ² represents a single bond or a methylene group,
Y ² is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, 2 a valent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or one or more methylene groups in the hydrocarbon group is replaced with a divalent group selected from the following group IIβ. However, when two or more methylene groups are replaced with divalent groups selected from Group IIβ below, the divalent groups are not adjacent to each other, and ^Y One or more of the hydrogen atoms is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, May be substituted with vinyl group, mercapto group, isocyanate group or carboxyl group,
n represents an integer from 1 to 12,
When the polymer contains a plurality of structural units represented by (Iβ), the plurality of R ⁵ , R ⁶ , R ⁷ , R ⁸ , Q ² , X ² and Y ² may be the same or different. In some cases,
* represents a bond.
Group Iβ: -O-, -S- or divalent heterocyclic group.
Group IIβ: -O-, -S-, -NR ¹⁹² -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group, R ¹⁹² represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ⁹ represents a hydrogen atom or a methyl group,
R ¹⁰ , R ¹¹ and R ¹² each independently represent a hydrogen atom, a halogen atom, a nitrile group, a heterocyclic group, a hydrocarbon group having 1 to 30 carbon atoms, or one of the methylene groups in the hydrocarbon group; Represents a group in which two or more of the methylene groups are replaced with a divalent group selected from the group Iγ below, provided that when two or more methylene groups are replaced with a divalent group selected from the group Iγ below, the two The valent groups are not adjacent to each other, and one or more hydrogen atoms in the groups represented by R ¹⁰ , R ¹¹ and R ¹² are a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, or a halogen group. may be substituted with an atom, nitro group, cyano group, hydroxyl group, amino group, methacryloyl group, acryloyl group, epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
Q ³ represents -O-, -CO-O- or -O-CO-,
X ³ represents a single bond or a methylene group,
Y ³ is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-, 2 a valent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or one or more methylene groups in the hydrocarbon group is replaced with a divalent group selected from the following group IIγ. However, when two or more methylene groups are replaced with divalent groups selected from Group IIγ below, the divalent groups are not adjacent to each other, ^and One or more of the hydrogen atoms is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, May be substituted with vinyl group, mercapto group, isocyanate group or carboxyl group,
n represents an integer from 1 to 12,
When the polymer contains a plurality of structural units represented by (Iγ), the plurality of R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , Q ³ , X ³ and Y ³ may be the same or different. In some cases,
* represents a bond.
Group Iγ: -O-, -S- or a divalent heterocyclic group.
Group IIγ: -O-, -S-, -NR ¹⁹³ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ¹⁹³ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are each independently a hydrogen atom, a halogen atom, a nitrile group, a heterocyclic group, a hydrocarbon group having 1 to 30 carbon atoms, or the hydrocarbon group. Represents a group in which one or more methylene groups are replaced with a divalent group selected from the following group Iδ, provided that two or more methylene groups are divalent groups selected from the following group Iδ ^{When substituted with _ _ _} is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a mercapto group, an isocyanate group, or May be substituted with carboxyl group,
Q ⁴ represents -O-, -CO-O- or -O-CO-,
Y ⁴ is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or -O-(CH ₂ ) _n -O-divalent a heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or one or more methylene groups in the hydrocarbon group has been replaced with a divalent group selected from the following Group IIδ group, provided that when two or more methylene groups are replaced with divalent groups selected from Group IIδ below, the divalent groups are not adjacent, and hydrogen in the group represented by Y ⁴ One or more of the atoms is a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl may be substituted with a group, a mercapto group, an isocyanate group or a carboxyl group,
n represents an integer from 1 to 12,
When the polymer contains a plurality of structural units represented by (Iδ), the plurality of R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , Q ⁴ and Y ⁴ may be the same. , may be different,
* represents a bond.
Group Iδ: -O-, -S- or a divalent heterocyclic group.
Group II δ: -O-, -S-, -NR ¹⁹⁴ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ¹⁹⁴ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ²¹ represents a hydrogen atom or a methyl group,
X ¹¹ represents -S-,
Z ¹ is a divalent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or a divalent group in which one or more methylene groups in the hydrocarbon group are selected from the group IIIα below. However, when two or more methylene groups are replaced with a divalent group selected from the following group IIIα, the divalent groups are not adjacent to each other and are represented by Z ¹ . One or more hydrogen atoms in the group include a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group. , may be substituted with an epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
When the polymer contains a plurality of structural units represented by (IIα), the plurality of R ²¹ and Z ¹ may be the same or different,
* represents a bond.
Group IIIα: -O-, -S-, -NR ²⁵¹ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ²⁵¹ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ²² represents a hydrogen atom or a methyl group,
X ¹² represents -S-,
Z ² is a divalent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or a divalent group in which one or more methylene groups in the hydrocarbon group are selected from Group IIIβ below. However, when two or more methylene groups are replaced with a divalent group selected from Group IIIβ below, the divalent groups are not adjacent and are represented by Z ² . One or more hydrogen atoms in the group include a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group. , may be substituted with an epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
When the polymer contains a plurality of structural units represented by (IIβ), the plurality of R ²² and Z ² may be the same or different,
* represents a bond.
Group IIIβ: -O-, -S-, -NR ²⁵² -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ²⁵² represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms.

In the formula, R ²³ represents a hydrogen atom or a methyl group,
X ¹³ represents -S-,
Z ³ is a divalent heterocyclic group, a divalent hydrocarbon group having 1 to 30 carbon atoms, or a divalent group in which one or more methylene groups in the hydrocarbon group are selected from Group IIIγ below. However, when two or more methylene groups are replaced with a divalent group selected from Group IIIγ below, the divalent groups are not adjacent and are represented by Z ³ . One or more hydrogen atoms in the group include a hydrocarbon group having 1 to 30 carbon atoms, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a methacryloyl group, an acryloyl group. , may be substituted with an epoxy group, vinyl group, mercapto group, isocyanate group or carboxyl group,
When the polymer contains a plurality of structural units represented by (IIγ), the plurality of R ²³ and Z ³ may be the same or different,
* represents a bond.
Group IIIγ: -O-, -S-, -NR ²⁵³ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH-, -C≡C - or a divalent heterocyclic group. R ²⁵³ represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. The polymer according to claim 1, which has a structural unit represented by formula (Iα), (Iβ), (Iγ) or (Iδ) in the main chain of the polymer. It has a structural unit represented by formula (Iα), a structural unit represented by formula (Iβ), or a structural unit represented by formula (Iγ),
The group represented by Y ¹ in formula (Iα) is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or - O-(CH ₂ ) _n -O-, where n is an integer from 1 to 12,
The group represented by Y ² in formula (Iβ) is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or - O-(CH ₂ ) _n -O-, where n is an integer from 1 to 12,
The group represented by Y ³ in formula (Iγ) is -O-, -O-CO-, -CO-O-, -O-CO-O-, -(CH ₂ ) _n -O- or - The polymer according to claim 1 or 2, which is O-(CH ₂ ) _n -O-, where n is an integer from 1 to 12. The groups represented by R ² , R ³ and R ⁴ in the above formula (Iα) are each independently a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms,
The groups represented by R ⁶ , R ⁷ and R ⁸ in the above formula (Iβ) are each independently a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms,
The groups represented by R ¹⁰ , R ¹¹ and R ¹² in the above formula (Iγ) are each independently a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms,
The groups represented by R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ in the above formula (Iδ) are each independently a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms, A polymer according to any one of claims 1 to 3. The total proportion of the structural unit represented by formula (Iα), the structural unit represented by formula (Iβ), the structural unit represented by formula (Iγ), and the structural unit represented by formula (Iδ) is Polymer according to any one of claims 1 to 4, in an amount of 20 to 52% by weight, based on the combined weight. The group represented by Z ¹ in the above formula (IIα) is a divalent hydrocarbon group having 1 to 10 carbon atoms, or one or more methylene groups of the hydrocarbon group is -O-, -OCO A group substituted with -, -COO-, -S- or -O-CO-O-,
The group represented by Z ¹ in the above formula (IIβ) is a divalent hydrocarbon group having 1 to 10 carbon atoms, or one or more methylene groups of the hydrocarbon group is -O-, -OCO A group substituted with -, -COO-, -S- or -O-CO-O-,
The group represented by Z ¹ in the above formula (IIγ) is a divalent hydrocarbon group having 1 to 10 carbon atoms, or one or more methylene groups of the hydrocarbon group is -O-, -OCO A group substituted with -, -COO-, -S- or -O-CO-O-,
A polymer according to any one of claims 1 to 5. The polymer according to any one of claims 1 to 6, having a weight average molecular weight of 1,000 to 500,000. The polymer according to any one of claims 1 to 7, having a polydispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of 1 to 2.5. A photodegradable resin containing the polymer according to any one of claims 1 to 8. A composition containing the polymer according to any one of claims 1 to 8. A light-disassembly adhesive comprising the polymer according to any one of claims 1 to 8. A pattern forming agent containing the polymer according to any one of claims 1 to 8. A photolatent catalyst comprising a polymer according to any one of claims 1 to 8 and an active species. A method for producing a decomposed product of a photodegradable resin, comprising the step of irradiating the photodegradable resin according to claim 9 with light.