Coating compositions and methods of forming electronic devices

Patent metadata

Field	Value
Publication number	US-11940732-B2
Application number	US-202117231417-A
Country	US
Kind code	B2
Filing date	Apr 15, 2021
Priority date	May 2, 2020
Publication date	Mar 26, 2024
Grant date	Mar 26, 2024

Abstract

Coating compositions comprise: a curable compound comprising: a core chosen from a C 6 carbocyclic aromatic ring, a C 2-5 heterocyclic aromatic ring, a C 9-30 fused carbocyclic aromatic ring system, a C 4-30 fused heterocyclic aromatic ring system, C 1-20 aliphatic, and C 3-20 cycloaliphatic, and three or more substituents of formula (1)

wherein at least two substituents of formula (1) are attached to the aromatic core; provided that no substituents of formula (1) are in an ortho position to each other on the same aromatic ring of the core; a polymer; and one or more solvents, wherein the total solvent content is from 50 to 99 wt % based on the coating composition.

First claim

What is claimed is:

1. A coating composition, comprising:
a first curable compound comprising: a core chosen from a C 6 carbocyclic aromatic ring, a C 2-5 heterocyclic aromatic ring, a C 9-30 fused carbocyclic aromatic ring system, a C 4-30 fused heterocyclic aromatic ring system, C 1-20 aliphatic, and C 3-20 cycloaliphatic, and three or more substituents of formula (1)

wherein at least two substituents of formula (1) are attached to the core, wherein the core is optionally further substituted; and wherein: Ar 1 is chosen from a C 6 carbocyclic aromatic ring, a C 2-5 heterocyclic aromatic ring, a C 9-30 fused carbocyclic aromatic ring system, and a C 4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SR 1 , protected thiol, —O—C(═O)—C 1-6 alkyl, halogen, and NHR 2 wherein each R 1 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, and C 5-30 aryl; each R 2 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, C 5-30 aryl, C(═O)—R 1 , and S(═O) 2 -R 1 ; x is an integer from 1 to the total number of available aromatic ring atoms in Ar 1 ; and * denotes the point of attachment to the core or to a portion of the curable compound other than the core; provided that no substituents of formula (1) are in an ortho position to each other on the same aromatic ring of the core;
a polymer chosen from: acrylates, vinyl aromatic polymers, novolacs, polyphenylenes, polybenzoxazoles, polybenzimidazoles, polyetheresulfones, and combinations thereof, or a B-staged reaction product of a second curable compound comprising a core chosen from a C 6 carbocyclic aromatic ring, a C 2-5 heterocyclic aromatic ring, a C 9-30 fused carbocyclic aromatic ring system, a C 4-30 fused heterocyclic aromatic ring system, C 1-20 aliphatic, and C 3-20 cycloaliphatic, and two or more substituents of formula (B-1) attached to the core, wherein the core is optionally further substituted:

wherein in formula (B-1): Ar 1 is chosen from a C 6 carbocyclic aromatic ring, a C 2-5 heterocyclic aromatic ring, a C 9-30 fused carbocyclic aromatic ring system, and a C 4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SR 1 , protected thiol, —O—C(═O)—C 1-6 alkyl, halogen, and NHR 2 ; wherein each R 1 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, and C 5-30 aryl; each R 2 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, C 5-30 aryl, C(═O)—R 1 , and S(═O) 2 -R 1 ; x is an integer from 1 to the total number of available aromatic ring atoms in Ar 1 ; and * denotes the point of attachment to the core or to a portion of the curable compound other than the core; provided that no substituents of formula (B-1) are in an ortho position to each other on the same aromatic ring of the core; and
one or more solvents, wherein the total solvent content is from 50 to 99 wt % based on the coating composition.

2. The coating composition of claim 1 , wherein the polymer is chosen from acrylates, vinyl aromatic polymers, novolacs, polyphenylenes, and combinations thereof.

3. The coating composition of claim 1 , wherein each Z of formula (1) is independently chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SH, —O—C(═O)—C 1-6 alkyl, and NHR 2 .

4. The coating composition of claim 3 , wherein each Z of formula (1) is hydroxyl.

5. The coating composition of any of claim 1 , wherein the core of the first curable compound is chosen from pyridine, benzene, naphthalene, quinoline, isoquinoline, anthracene, phenanthrene, pyrene, coronene, triphenylene, chrysene, phenalene, benz [a] anthracene, dibenz[a,h]anthracene, and benzo [a] pyrene.

6. The coating composition of claim 1 , wherein each Ar 1 of formula (1) is independently chosen from pyridine, benzene, naphthalene, quinoline, isoquinoline, anthracene, phenanthrene, pyrene, coronene, triphenylene, chrysene, phenalene, benz [a] anthracene, dibenz[a,h]anthracene, and benzo [a] pyrene.

7. The coating composition of claim 1 , further comprising a curing agent, a surface leveling agent, or a flow additive.

8. The coating composition of claim 1 , further comprising a crosslinker that is different from the first curable compound and the polymer.

9. A coated substrate, comprising:
an electronic device substrate; and
a layer formed from a coating composition of claim 1 on a surface of the electronic device substrate.

10. A method of forming an electronic device, comprising:
(a) providing an electronic device substrate;
(b) coating a layer of a coating composition of claim 1 on a surface of the electronic device substrate; and
(c) curing the layer of the curable compound to form a cured layer.

11. The method of claim 10 , wherein the cured layer is a photoresist underlayer, the method further comprising:
(d) forming a photoresist layer over the underlayer;
(e) patternwise exposing the photoresist layer to activating radiation;
(f) developing the exposed photoresist layer to form a pattern in the photoresist layer; and
(g) transferring the pattern to the underlayer.

12. The method of claim 11 , further comprising coating one or more of a silicon-containing layer, an organic antireflective coating layer, or a combination thereof over the underlayer before step (d).

13. The method of claim 12 , further comprising transferring the pattern to the one or more of the silicon-containing layer, the organic antireflective coating layer, or the combination thereof after step (f) and before step (g).

14. The method of claim 11 , further comprising:
(h) transferring the pattern to a layer of the electronic device substrate below the patterned underlayer; and
(i) removing the patterned underlayer.

15. The method of claim 10 , wherein the polymer is chosen from acrylates, vinyl aromatic polymers, novolacs, polyphenylenes, and combinations thereof.

16. The method of claim 10 , wherein the polymer is a B-staged reaction product of a second curable compound comprising a core chosen from a C 6 carbocyclic aromatic ring, a C 2-5 heterocyclic aromatic ring, a C 9-30 fused carbocyclic aromatic ring system, a C 4-30 fused heterocyclic aromatic ring system, C 1-20 aliphatic, and C 3-20 cycloaliphatic, and two or more substituents of formula (B-1) attached to the core:

wherein in formula (B-1): Ar 1 is chosen from a C 6 carbocyclic aromatic ring, a C 2-5 heterocyclic aromatic ring, a C 9-30 fused carbocyclic aromatic ring system, and a C 4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SR 1 , protected thiol, —O—C(═O)—C 1-6 alkyl, halogen, and NHR 2 ;
wherein each R 1 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, and C 5-30 aryl; each R 2 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, C 5-30 aryl, C(═O)—R 1 , and S(═O) 2 -R 1 ; x is an integer from 1 to the total number of available aromatic ring atoms in Ar 1 ; and * denotes the point of attachment to the co

Assignees

• Rohm & Haas Elect Mat

Inventors

• Liu Sheng
• Cameron James F
• Yamada Shintaro
• Ke Iou-Sheng
• Zhang Keren
• Coley Suzanne M
• Cui Li
• Labeaume Paul J
• Wang Deyan

Classifications

• G03F7/11 Primary

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

• C09D4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 · CPC title

• C09D7/47

  Levelling agents · CPC title

• C09D7/63 Primary

  organic · CPC title

• G03F7/025 Primary

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon triple bonds, e.g. acetylenic compounds (G03F7/075 takes precedence) · CPC title