Adhesion promoting photoresist underlayer composition

Patent metadata

Field	Value
Publication number	US-12379660-B2
Application number	US-202017127434-A
Country	US
Kind code	B2
Filing date	Dec 18, 2020
Priority date	Dec 18, 2020
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

A photoresist underlayer composition comprising a poly(arylene ether); an additive of formula (14):

D-(L 1 -Ar—[X] n ) m   (14); and

a solvent, wherein, in formula (14), D is a substituted or unsubstituted C 1-60 organic group, optionally wherein D is an organic acid salt of the substituted or unsubstituted C 1-60 organic group; each L 1 is independently a single bond or a divalent linking group, when L 1 is a single bond, D may be a substituted or unsubstituted C 3-30 cycloalkyl or substituted or unsubstituted C 1-20 heterocycloalkyl that is optionally fused with Ar, each Ar is independently a monocyclic or polycyclic C 5-60 aromatic group, each X is independently —OR 30 , —SR 31 , or —NR 32 R 33 , m is an integer of 1 to 6, each n is independently an integer of 0 to 5, provided that a sum of all n is 2 or greater, and R 30 to R 33 are as provided herein.

First claim

What is claimed is:

1. A photoresist underlayer composition, comprising:
a poly (arylene ether) derived from a compound containing two or more cyclopentadienone moieties, wherein the compound is free of a solubility enhancing polar moiety;
an additive of formula (14):
D-(L 1 -Ar—[X] n ) m   (14); and

a solvent,
wherein, in formula (14),
D is a substituted or unsubstituted C 1-60 organic group, optionally wherein D is an organic acid salt of the substituted or unsubstituted C 1-60 organic group;
each L 1 is independently a single bond or a divalent linking group,
when L 1 is a single bond, D may be a substituted or unsubstituted C 3-30 cycloalkyl or substituted or unsubstituted C 1-20 heterocycloalkyl that is optionally fused with Ar,
each Ar is independently a monocyclic or polycyclic C 5-60 aromatic group,
each X is independently −OR 30 , −SR 31 , or −NR 32 R 33 ,
m is an integer of 1 to 6,
each n is independently an integer of 0 to 5, provided that a sum of all n is 2 or greater,
R 30 to R 33 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 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, each of which except hydrogen optionally further comprises as part of its structure one or more of substituted or unsubstituted C 1-30 alkylene, substituted or unsubstituted C 3-30 cycloalkylene, substituted or unsubstituted C 2-30 alkenylene, substituted or unsubstituted C 4-30 cycloalkenylene, substituted or unsubstituted C 2-30 alkynylene, substituted or unsubstituted C 1-30 heterocycloalkylene, substituted or unsubstituted C 6-30 arylene, substituted or unsubstituted C 4-30 heteroarylene, —O—, —C(O)—, —C(O)O—, —S—, —S(O)—, —S(O) 2 —, or −NR 34 — wherein R 34 is substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 1-20 heterocycloalkyl, 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 4-30 heteroaryl, substituted or unsubstituted C 5-30 heteroarylalkyl, or substituted or unsubstituted C 5-30 alkylheteroaryl, and
when n is 2, optionally any one of R 30 to R 33 of a first group X is a divalent group, any one of R 30 to R 33 of a second group X is a divalent group, and the divalent group of the first group X forms a ring together with the divalent group of the second group X, wherein the ring optionally further comprises a linking group comprising one or more of substituted or unsubstituted C 1-30 alkylene, substituted or unsubstituted C 3-30 cycloalkylene, substituted or unsubstituted C 2-30 alkenylene, substituted or unsubstituted C 4-30 cycloalkenylene, substituted or unsubstituted C 2-30 alkynylene, substituted or unsubstituted C 6-30 arylene, —O—, —C(O)—, —C(O)O—, —NR 35 —, —S—, —S(O)—, or —S(O) 2 —, wherein R 35 is substituted or unsubstituted C 1-30 alkyl, substituted or unsubstituted C 3-30 cycloalkyl, substituted or unsubstituted C 1-20 heterocycloalkyl, 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 4-30 heteroaryl, substituted or unsubstituted C 5-30 heteroarylalkyl, or substituted or unsubstituted C 5-30 alkylheteroaryl.

2. The photoresist underlayer composition of claim 1 , wherein D is a polyvalent C 1-30 alkyl, a polyvalent C 3-30 cycloalkyl, a polyvalent C 1-20 heterocycloalkyl, a polyvalent C 6-30 aryl, a polyvalent C 6-30 heteroaryl, —NH 2 or an organic acid salt thereof, or —C(O)OR 22 wherein R 22 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.

3. The photoresist underlayer composition of claim 1 , wherein
D is a polyvalent C 1-30 alkyl, a polyvalent C 3-30 cycloalkyl, a polyvalent C 6-30 aryl, or a polyvalent C 6-30 heteroaryl,
each L 1 is independently a single bond or a divalent linking group comprising one or more of substituted or unsubstituted C 1-30 alkylene, substituted or unsubstituted C 3-30 cycloalkylene, substituted or unsubstituted C 2-30 alkenylene, substituted or unsubstituted C 4-30 cycloalkenylene, substituted or unsubstituted C 2-30 alkynylene, substituted or unsubstituted C 1-30 heterocycloalkylene, substituted or unsubstituted C 6-30 arylene, substituted or unsubstituted C 4-30 heteroarylene, —O—, —C(O)—, —C(O)O—, —NR 23 —, —S—, —S(O)—, —S(O) 2 —, or —C(O)NR 23 —,
R 23 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,
each Ar is independently a monocyclic or polycyclic C 6-60 arylene group,
each X is independently —OR 30 or —NR 32 R 33 ,
R 30 , R 32 , and R 33 are the same as provided for claim 1 ,
m is an integer of 2 to 4, and
the sum of n is 3 or greater.

4. A photoresist underlayer composition, comprising:
a poly (arylene ether) derived from a compound containing two or more cyclopentadienone moieties,
an additive of formula (15):

a solvent,
wherein, in formula (15),
D is a polyvalent C 1-30 alkyl, a polyvalent C 3-30 cycloalkyl, a polyvalent C 6-30 aryl, or a polyvalent C 6-30 heteroaryl,
each Ar 5 is a monocyclic or polycyclic C 6-60 arylene group or a monocyclic or polycyclic C 5-60 heteroarylene group,
each X is independently —OR 30 , —SR 31 , or —NR 32 R 33 ,
R 30 to R 33 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 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, each of which except hydrogen optionally further comprises as part of its structure one or more of substituted or unsubstituted C 1-30 alkylene, substituted or unsubstituted C 3-30 cycloalkylene, substituted or unsubstituted C 2-30 alkenylene, substituted or unsubstituted C 4-30 cycloalkenylene, substituted or unsubstituted C 2-30 alkynylene, substituted or unsubstituted C 1-30 hete

Assignees

• Rohm & Haas Elect Mat
• Dupont Electronic Mat International Llc

Inventors

• Kaitz Joshua
• Yang Ke
• Zhang Keren
• Cui Li
• Cameron James F
• Millward Dan B
• Yamada Shintaro

Classifications

• G03F7/11 Primary

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

• C08K5/105

  with phenols · CPC title

• C08K5/19

  Quaternary ammonium compounds · CPC title

• C08K5/09

  Carboxylic acids; Metal salts thereof; Anhydrides thereof · CPC title

• C08K5/053

  Polyhydroxylic alcohols · CPC title