Coating composition for photoresist underlayer

Patent metadata

Field	Value
Publication number	US-11762294-B2
Application number	US-202017007877-A
Country	US
Kind code	B2
Filing date	Aug 31, 2020
Priority date	Aug 31, 2020
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

A photoresist underlayer composition, comprising a polymer comprising a repeating unit of formula (1):

wherein Ar is a monocyclic or polycyclic C 5-60 aromatic group, wherein the aromatic group comprises one or more aromatic ring heteroatoms, a substituent group comprising a heteroatom, or a combination thereof; R 1 is hydrogen, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl; and R 2 is substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl, wherein R 1 and R 2 can be optionally taken together to form a ring.

First claim

What is claimed is:

1. A photoresist underlayer composition, comprising:
a polymer comprising a repeating unit of formula (1); and
a crosslinking agent:

wherein
Ar is a monocyclic or polycyclic C 5-60 aromatic group, wherein the C 5-60 aromatic group comprises one or more aromatic ring heteroatoms, a substituent group comprising a heteroatom, or a combination thereof;
R 1 is hydrogen, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl; and
R 2 is substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl,
wherein R 1 and R 2 can be optionally taken together to form a ring,
wherein the photoresist underlayer composition is free of a photoacid generator.

2. The photoresist underlayer composition of claim 1 , wherein Ar is a monocyclic or polycyclic C 5-60 heteroarylene group or a monocyclic or polycyclic C 6-60 arylene group, optionally substituted with at least one of substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 haloalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 1-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 3-30 heteroaryl, substituted or unsubstituted C 4-30 heteroarylalkyl, halogen, —OR 11 , —SR 12 , or —NR 13 R 14 , wherein R 11 to R 14 are each independently hydrogen, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl,
provided that the monocyclic or polycyclic C 6-60 arylene group is substituted with at least one substituent group comprising a heteroatom.

3. The photoresist underlayer composition of claim 1 , wherein Ar comprises a group of formula (2):

wherein,
A1, A2, and A3 each may be present or absent, and each independently represents 1 to 3 fused aromatic rings;
R 3 and R 4 are each independently substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl, halogen, —OR 21 , —SR 22 , or —NR 23 R 24 ; and
provided that at least one of R 3 or R 4 is —OR 21 , —SR 22 , or —NR 23 R 24 ;
R 21 to R 24 are each independently hydrogen, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl;
m is an integer 0 to 4;
n is an integer 0 to 4; and
provided that the sum of m and n is an integer greater than 0.

4. The photoresist underlayer composition of claim 1 , wherein Ar comprises a group of formulae (3a), (3b), or (3c):

wherein,
A4 may be present or absent, and represents 1 to 3 fused aromatic rings;
Z 1 and Z 2 are each independently C or N;
each R 5 is independently substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl; and
p is an integer of 0 to 4,
wherein A4 comprises at least one heteroaryl ring, at least one of Z 1 and Z 2 is N, or a combination thereof.

5. The photoresist underlayer composition of claim 1 , wherein Ar comprises a group of formula (4):

wherein,
L 1 is a single bond, —O—, —S—, —S(O)—, —SO 2 —, —C(O)—, —CR 41 R 42 —, —NR 43 —, or —PR 44 —;
L 2 is absent, a single bond, —O—, —S—, —S(O)—, —SO 2 —, —C(O)—, substituted or unsubstituted C 1-2 alkylene, substituted or unsubstituted C 6-30 arylene, or substituted or unsubstituted C 5-30 heteroarylene;
R 8 and R 9 are each independently substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 2-30 alkenyl, substituted or unsubstituted C 2-30 alkynyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 7-30 alkylaryl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl, halogen, —OR 45 , —SR 46 , or —NR 47 R 48 ;
R 41 to R 48 are each independently hydrogen, substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 1-30 heteroalkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 2-30 heterocycloalkyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 7-30 arylalkyl, substituted or unsubstituted C 3-30 heteroaryl, or substituted or unsubstituted C 4-30 heteroarylalkyl;
a is an integer of 0 to 4; and
b is an integer of 0 to 4.

6. The photoresist underlayer composition of claim 1 , wherein the monocyclic or polycyclic C 5-60 aromatic group is a monocyclic or polycyclic C 6-60 arylene group substituted with hydroxyl.

7. The photoresist underlayer composition of claim 1 , wherein the polymer comprises a repeating unit of formula (6):

wherein R 1 and R 2 are as defined in any one of clai

Assignees

• Rohm & Haas Elect Mat

Inventors

• Kaitz Joshua
• Liu Sheng
• Cui Li
• Yamada Shintaro
• Coley Suzanne M
• Ke Iou-Sheng

Classifications

• H10P76/4085

  characterised by the processes involved to create the masks · CPC title

• H10P76/405

  characterised by their composition, e.g. multilayer masks · CPC title

• C09D165/00 Primary

  Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers · CPC title

• G03F7/094 Primary

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

• C09D7/63 Primary

  organic · CPC title