# US 2021/0341840 A1 · Coating compositions and methods of forming electronic devices

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- Number: US 2021/0341840 A1
- Document ID: US20210341840A1
- Status: Published application
- Kind: A1
- Application number: 17/231,417
- Filed: 2021-04-15
- Published: 2021-11-04
- Earliest claimed: 2020-05-02
- Assignees: Rohm and Haas Electronic Materials LLC
- Applicants: Rohm and Haas Electronic Materials LLC
- Inventors: Sheng Liu; James F. Cameron; Shintaro YAMADA; Iou-Sheng KE; Keren ZHANG; Suzanne M. Coley; Li Cui; Paul J. LaBeaume; Deyan Wang
- Web page: https://patentgrep.com/patent/US20210341840A1

## CPC

- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- C09D 4/06: {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
- C09D 7/47: Levelling agents
- C09D 7/63: organic
- G03F 7/025: Non-macromolecular photopolymerisable compounds having carbon-to-carbon triple bonds, e.g. acetylenic compounds (G03F7/075 takes precedence)
- G03F 7/0752: {in non photosensitive layers or as additives, e.g. for dry lithography}
- G03F 7/091: {characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement}
- G03F 7/094: {Multilayer resist systems, e.g. planarising layers}
- G03F 7/16: Coating processes; Apparatus therefor (applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74)
- G03F 7/2016: {Contact mask being integral part of the photosensitive element and subject to destructive removal during post-exposure processing}
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

Coating compositions comprise: a curable compound comprising: a core chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, a C4-30 fused heterocyclic aromatic ring system, C1-20 aliphatic, and C3-20 cycloaliphatic, and three or more substituents of formula (1) wherein at least two substituents of formula (1) are attached to the aromatic core; and wherein: Ar1 is chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, and a C4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SR1, protected thiol, —O—C(═O)—C1-6 alkyl, halogen, and NHR2; wherein each R1 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, and C5-30 aryl; each R2 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, C5-30 aryl, C(═O)—R1, and S(═O)2—R1; x is an integer from 1 to the total number of available aromatic ring atoms in Ar1; and * denotes the point of attachment to 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; and one or more solvents, wherein the total solvent content is from 50 to 99 wt % based on the coating composition. Coated substrates formed with the coating compositions and methods of forming electronic devices using the compositions are also provided. The compositions, coated substrates and methods find particular applicability in the manufacture of semiconductor devices.

## Claims

### Claim 1

A coating composition, comprising:
a first curable compound comprising: a core chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, a C4-30 fused heterocyclic aromatic ring system, C1-20 aliphatic, and C3-20 cycloaliphatic, and three or more substituents of formula (1)
wherein at least two substituents of formula (1) are attached to the core; and wherein: Ar1 is chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, and a C4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SR1, protected thiol, —O—C(═O)—C1-6 alkyl, halogen, and NR2; wherein each R1 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, and C5-30 aryl; each R2 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, C5-30 aryl, C(═O)—R1, and S(═O)2—R1; x is an integer from 1 to the total number of available aromatic ring atoms in Ar1; and * denotes the point of attachment to 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; and
one or more solvents, wherein the total solvent content is from 50 to 99 wt % based on the coating composition.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 2)

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

### Claim 4 (depends on 1)

The coating composition of claim 1, wherein the polymer is a B-staged reaction product of a second curable compound comprising a core chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, a C4-30 fused heterocyclic aromatic ring system, C1-20 aliphatic, and C3-20 cycloaliphatic, and two or more substituents of formula (B-1) attached to the core:
wherein in formula (B-1): Ar1 is chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, and a C4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SR1, protected thiol, —O—C(═O)—C1-6 alkyl, halogen, and NHR2; wherein each R1 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, and C5-30 aryl; each R2 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, C5-30 aryl, C(═O)—R1, and S(═O)2—R1; x is an integer from 1 to the total number of available aromatic ring atoms in Ar1; and * denotes the point of attachment to 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.

### Claim 5 (depends on 1)

The coating composition of claim 1, wherein each Z of formula (1) is independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SH, —O—C(═O)—C1-6 alkyl, and NHR2.

### Claim 6 (depends on 5)

The coating composition of claim 5, wherein each Z of formula (1) is hydroxyl.

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 1)

The coating composition of claim 1, wherein each Ar1 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.

### Claim 9 (depends on 1)

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

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 1)

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.

### Claim 13 (depends on 12)

The method of claim 12, 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.

### Claim 14 (depends on 13)

The method of claim 13, 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).

### Claim 15 (depends on 14)

The method of claim 14, 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).

### Claim 16 (depends on 13)

The method of claim 13, further comprising:
(h) transferring the pattern to a layer of the electronic device substrate below the patterned underlayer; and
(i) removing the patterned underlayer.

### Claim 17 (depends on 12)

The method of claim 12, wherein the polymer is chosen from acrylates, vinyl aromatic polymers, novolacs, polyphenylenes, and combinations thereof.

### Claim 18 (depends on 12)

The method of claim 12, wherein the polymer is a B-staged reaction product of a second curable compound comprising a core chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, a C4-30 fused heterocyclic aromatic ring system, C1-20 aliphatic, and C3-20 cycloaliphatic, and two or more substituents of formula (B-1) attached to the core:
wherein in formula (B-1): Ar1 is chosen from a C6 carbocyclic aromatic ring, a C2-5 heterocyclic aromatic ring, a C9-30 fused carbocyclic aromatic ring system, and a C4-30 fused heteroocyclic aromatic ring system; Z is a substituent independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SR1, protected thiol, —O—C(═O)—C1-6 alkyl, halogen, and NHR2; wherein each R1 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, and C5-30 aryl; each R2 is independently chosen from H, C1-10 alkyl, C2-10 unsaturated hydrocarbyl, C5-30 aryl, C(═O)—R1, and S(═O)2—R1; x is an integer from 1 to the total number of available aromatic ring atoms in Ar1; and * denotes the point of attachment to 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.

### Claim 19 (depends on 12)

The method of claim 12, wherein each Z of formula (1) is independently chosen from OR1, protected hydroxyl, carboxyl, protected carboxyl, SH, —O—C(═O)—C1-6 alkyl, and NHR2.

### Claim 20 (depends on 19)

The method of claim 19, wherein each Z of formula (1) is hydroxyl.