Compound, resin, composition, resist pattern formation method, circuit pattern formation method and method for purifying resin

Patent metadata

Field	Value
Publication number	US-11747728-B2
Application number	US-201917044772-A
Country	US
Kind code	B2
Filing date	May 27, 2019
Priority date	May 28, 2018
Publication date	Sep 5, 2023
Grant date	Sep 5, 2023

Abstract

An object of the present invention is to provide a new compound that is useful as a film forming material for lithography and the like. The above object can be achieved by a compound represented by the following formula (1).

First claim

The invention claimed is:

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

wherein
A is a group having 1 to 12 carbon atoms;
R 1 is a 2n-valent group having 1 to 30 carbon atoms;
R 2 to R 5 are each independently a linear, branched, or cyclic alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a thiol group, or a hydroxyl group;
at least one R 4 and/or at least one R 5 is a hydroxy group and/or a thiol group;
m 2 and m 3 are each independently an integer of 0 to 8;
m 4 and m 5 are each independently an integer of 0 to 9;
n is an integer of 1 to 4; and
p 2 to p 5 are each independently an integer of 0 to 2.

2. The compound according to claim 1 , wherein, in the above formula (1), at least one R 2 and/or at least one R 3 is a hydroxy group and/or a thiol group.

3. The compound according to claim 1 , wherein the compound represented by the above formula (1) is a compound represented by the following formula (1a):

wherein
A, R 2 to R 5 , and n are each as defined in the above formula (1);
R 1a is a hydrogen atom or a monovalent group having 1 to 10 carbon atoms;
R 1b is an n-valent group having 1 to 25 carbon atoms;
m 2 and m 3 are each independently an integer of 0 to 4; and
m 4 and m 5 are each independently an integer of 0 to 5.

4. The compound according to claim 3 , wherein the compound represented by the above formula (1a) is a compound represented by the following formula (1b):

wherein
A, R 4 , R 5 , R 1a , R 1b , m 4 , m 5 , and n are each as defined in the above formula (1a);
R 6 and R 7 are each independently a linear, branched, or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a thiol group, or a hydroxyl group;
m 6 and m 7 are each independently an integer of 0 to 3; and
R 10 and R 11 are a hydrogen atom.

5. The compound according to claim 4 , wherein the compound represented by the above formula 1b is a compound represented b the following formula (1c):

wherein
A, R 1a , R 1b , R 6 , R 7 , R 10 , R 11 , m 6 , m 7 , and n are each as defined in the above formula (1b);
R 8 and R 9 are each independently a linear, branched, or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a thiol group, or a hydroxyl group;
m 8 and m 9 are each independently an integer of 0 to 4; and
R 12 and R 13 are a hydrogen atom.

6. A resin having a constitutional unit derived from the compound according to claim 1 .

7. The resin according to claim 6 , wherein the resin has a structure represented by the following formula (2):

wherein
A, R 1 to R 5 , m 2 to m 5 , n, and p 2 to p 5 are each as defined in the above formula (1); and
L is a single bond or a linking group.

8. A composition comprising the compound according to claim 1 .

9. The composition according to claim 8 , further comprising a solvent.

10. The composition according to claim 8 , further comprising an acid generating agent.

11. The composition according to claim 8 , further comprising a crosslinking agent.

12. The composition according to claim 8 , wherein the composition is used in film formation for lithography.

13. The composition according to claim 8 , wherein the composition is used in optical component formation.

14. A method for forming a resist pattern, comprising the steps of:
a photoresist layer formation step of forming a photoresist layer on a supporting material using the composition according to claim 12 ; and
a development step of irradiating a predetermined region of the photoresist layer formed through the photoresist layer formation step with radiation for development.

15. The method for forming a resist pattern according to claim 14 , wherein the resist pattern is an insulating film pattern.

16. A method for forming a resist pattern, comprising:
an underlayer film formation step of forming an underlayer film on a supporting material using the composition according to claim 12 ;
a photoresist layer formation step of forming at least one photoresist layer on the underlayer film formed through the underlayer film formation step; and
a step of irradiating a predetermined region of the photoresist layer formed through the photoresist layer formation step with radiation for development.

17. A method for forming a circuit pattern, comprising:
an underlayer film formation step of forming an underlayer film on a supporting material using the composition according to claim 12 ;
an intermediate layer film formation step of forming an intermediate layer film on the underlayer film formed through the underlayer film formation step;
a photoresist layer formation step of forming at least one photoresist layer on the intermediate layer film formed through the intermediate layer film formation step;
a resist pattern formation step of irradiating a predetermined region of the photoresist layer formed through the photoresist layer formation step with radiation for development, thereby forming a resist pattern;
an intermediate layer film pattern formation step of etching the intermediate layer film with the resist pattern formed through the resist pattern formation step as a mask, thereby forming an intermediate layer film pattern;
an underlayer film pattern formation step of etching the underlayer film with the intermediate layer film pattern formed through the intermediate layer film pattern formation step as a mask, thereby forming an underlayer film pattern; and
a supporting material pattern formation step of etching the supporting material with the underlayer film pattern formed through the underlayer film pattern formation step as a mask, thereby forming a pattern on the supporting material.

18. A method for purifying the compound according to claim 1 , comprising:
an extraction step of bringing a solution containing the compound and an organic solvent that does not inadvertently mix with water into contact with an acidic aqueous solution, thereby carrying out extraction.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Horiuchi Junya
• Okada Yu
• Makinoshima Takashi
• Echigo Masatoshi

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• H10P50/73

  using masks for insulating materials · CPC title

• G03F7/11 Primary

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title

• C07C39/15 Primary

  with all hydroxy groups on non-condensed rings {, e.g. phenylphenol} · CPC title

• C07C39/367

  polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes · CPC title