Novel (meth)acryloyl compound and method for producing same

Patent metadata

Field	Value
Publication number	US-2018210341-A1
Application number	US-201615746703-A
Country	US
Kind code	A1
Filing date	Jul 21, 2016
Priority date	Jul 23, 2015
Publication date	Jul 26, 2018
Grant date	—

Abstract

A (meth)acryloyl compound represented by the following formula (A):

wherein X is a 2m-valent group having 1 to 60 carbon atoms or a single bond; each Z is independently an oxygen atom, a sulfur atom, or not a crosslink; each R 1 is independently a linear, branched, or cyclic alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms and optionally having a substituent, an alkenyl group having 2 to 30 carbon atoms and optionally having a substituent, an alkoxy group having 1 to 30 carbon atoms and optionally having a substituent, a halogen atom, a nitro group, an amino group, a carboxylic acid group, a thiol group, a hydroxy group, or a group in which a hydrogen atom of a hydroxy group is replaced with a vinylphenylmethyl group, wherein the alkyl group, the aryl group, the alkenyl group, or the alkoxy group optionally contains an ether bond, a ketone bond, or an ester bond; each R 1A is independently a methyl group or a hydrogen atom; each k is independently an integer of 0 to 2, provided that all of the k moieties are not 0 at the same time; m is an integer of 1 to 3; each n is independently an integer of 0 to 5; and each p is independently 0 or 1.

First claim

1 . A (meth)acryloyl compound represented by the following formula (A):

wherein X is a 2m-valent group having 1 to 60 carbon atoms or a single bond; each Z is independently an oxygen atom, a sulfur atom, or not a crosslink; each R 1 is independently a linear, branched, or cyclic alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms and optionally having a substituent, an alkenyl group having 2 to 30 carbon atoms and optionally having a substituent, an alkoxy group having 1 to 30 carbon atoms and optionally having a substituent, a halogen atom, a nitro group, an amino group, a carboxylic acid group, a thiol group, a hydroxy group, or a group in which a hydrogen atom of a hydroxy group is replaced with a vinylphenylmethyl group, wherein the alkyl group, the aryl group, the alkenyl group, or the alkoxy group optionally contains an ether bond, a ketone bond, or an ester bond; each R 1A is independently a methyl group or a hydrogen atom; each k is independently an integer of 0 to 2, provided that all of the k moieties are not 0 at the same time; m is an integer of 1 to 3; each n is independently an integer of 0 to 5; and each p is independently 0 or 1.

2 . The (meth)acryloyl compound according to claim 1 , wherein X is a 2m-valent group having 1 to 19 carbon atoms or a single bond, each Z is independently an oxygen atom, a sulfur atom, or not a crosslink, each R 1 is independently an alkyl group having 1 to 4 carbon atoms or a halogen atom, each R1A is independently a methyl group or a hydrogen atom, each k is independently an integer of 0 to 2, provided that all of the k moieties are not 0 at the same time, m is an integer of 1 to 3, each n is independently an integer of 0 to 5, and each p is independently 0 or 1, in the above formula (A).

3 . The (meth)acryloyl compound according to claim 1 , wherein every p is 1, in the above formula (A).

4 . The (meth)acryloyl compound according to claim 1 , wherein Z is an oxygen atom, in the above formula (A).

5 . The (meth)acryloyl compound according to claim 1 , wherein Z is not a crosslink, in the above formula (A).

6 . The (meth)acryloyl compound according to claim 4 , wherein the compound represented by the above formula (A) is a compound represented by the following formula (1):

wherein X, R 1 , R 1A , m, and n are the same as the groups in the above formula (A).

7 . A method for producing the (meth)acryloyl compound according to claim 6 , comprising:
a step of reacting a compound represented by the following formula (2) with a (meth)acryloyl group introducing agent in the presence of a basic catalyst:

wherein X is a 2m-valent group having 1 to 19 carbon atoms or a single bond; each R 1 is independently an alkyl group having 1 to 4 carbon atoms or a halogen atom; m is an integer of 1 to 3; and each n is independently an integer of 0 to 5.

8 . The (meth)acryloyl compound according to claim 4 , wherein the compound represented by the above formula (A) is a compound represented by the following formula (1′):

wherein X, R 1 , R 1A , m, and n are the same as the groups in the above formula (A).

9 . A method for producing the (meth)acryloyl compound according to claim 8 , comprising:
a step of reacting a compound represented by the following formula (2′) with a (meth)acryloyl group introducing agent in the presence of a basic catalyst:

wherein X is a 2m-valent group having 1 to 19 carbon atoms or a single bond; each R 1 is independently an alkyl group having 1 to 4 carbon atoms or a halogen atom; m is an integer of 1 to 3; and each n is independently an integer of 0 to 5.

10 . The (meth)acryloyl compound according to claim 6 , wherein the compound represented by the above formula (1) is a compound represented by the following formula (4) or (7):

11 . The (meth)acryloyl compound according to claim 8 , wherein the compound represented by the above formula (1′) is a compound represented by the following formula (4′):

12 . A resin comprising a constituent unit derived from the compound according to claim 1 .

13 . A composition comprising: one or more selected from the group consisting of the compound according to claim 1 ; and a resin comprising a constituent unit derived from the compound.

14 . A composition for forming optical component comprising: one or more selected from the group consisting of the compound according to claim 1 ; and a resin comprising a constituent unit derived from the compound.

15 . A film forming composition for lithography comprising: one or more selected from the group consisting of the compound according to claim 1 ; and a resin comprising a constituent unit derived from the compound.

16 . A resist composition comprising: one or more selected from the group consisting of the compound according to claim 1 ; and thea resin comprising a constituent unit derived from the compound.

17 . The resist composition according to claim 16 , further comprising a solvent.

18 . The resist composition according to claim 16 , further comprising an acid generating agent.

19 . The resist composition according to claim 16 , further comprising an acid diffusion controlling agent.

20 . A method for forming a resist pattern, comprising:
a step of forming a resist film on a substrate using the resist composition according to claim 16 ; a step of exposing at least a portion of the formed resist film; and a step of developing the exposed resist film, thereby forming a resist pattern.

21 . A radiation-sensitive composition comprising:
a component (A) which is one or more selected from the group consisting of the compound according to claim 1 ; and a resin comprising a constituent unit derived from the compound, an optically active diazonaphthoquinone compound (B); and a solvent, wherein a content of the solvent is 20 to 99% by mass based on 100% by mass in total of the radiation-sensitive composition, and the content of components except for the solvent is 1 to 80% by mass based on 100% by mass in total of the radiation-sensitive composition.

22 . The radiation-sensitive composition according to claim 21 , wherein a content ratio among the compound and/or the resin (A), the optically active diazonaphthoquinone compound (B), and a further optional component (D) optionally contained in the radiation-sensitive composition ((A)/(B)/(D)) is (1 to 99% by mass)/(99 to 1% by mass)/(0 to 98% by mass), based on 100% by mass of solid components of the radiation-sensitive composition.

23 . The radiation-sensitive composition according to claim 21 , wherein the radiation-sensitive composition is capable of forming an amorphous film by spin coating.

24 . A method for producing an amorphous fil

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Echigo Masatoshi

Classifications

• G03F7/094 Primary

  Multilayer resist systems, e.g. planarising layers · CPC title

• C07C69/017 Primary

  Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C07B61/00

  Other general methods · CPC title

• G03F7/0758

  with silicon- containing groups in the side chains · CPC title