# US 9,519,215 B2 · Composition of matter and molecular resist made therefrom

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- Number: US 9,519,215 B2
- Document ID: US9519215B2
- Status: Granted
- Kind: B2
- Application number: 14/977,520
- Filed: 2015-12-21
- Published: 2016-08-25
- Granted: 2016-12-13
- Earliest claimed: 2013-10-31
- Assignees: Irresistible Materials LTD
- Applicants: Alex Phillip Graham Robinson; Dongxu Yang; Andreas Frommhold; Thomas Lada; John L. Roth; Xiang Xue; Edward A. Jackson
- Inventors: Alex Phillip Graham Robinson; Dongxu Yang; Andreas Frommhold; Thomas Lada; John L. Roth; Xiang Xue; Edward A. Jackson
- Web page: https://patentgrep.com/patent/US9519215B2

## CPC

- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- C07D 245/02: not condensed with other rings
- C07D 487/04: Ortho-condensed systems
- C07D 487/08: Bridged systems
- C07D 487/14: Ortho-condensed systems
- C07D 498/14: Ortho-condensed systems
- G03F 7/0382: {the macromolecular compound being present in a chemically amplified negative photoresist composition}
- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence)
- G03F 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)}
- H10K 71/233: {by photolithographic etching}
- H10K 85/215: {comprising substituents, e.g. PCBM}
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present application for patent discloses a composition of matter comprising: comprising a solvent; and an ester having a chemical structure chosen from (I), (II), or (III); wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group, wherein R1 is a saturated or unsaturated group having from 1-4 carbon atoms, R2 is chosen from hydrogen or a saturated or unsaturated group having from 1-4 carbon atoms, R3 is a saturated or unsaturated group having from 1-4 carbon atoms, and R4 is a saturated or unsaturated group having from 1-4 carbon atoms and A− is an anion.

## Claims

### Claim 1

A composition of matter comprising: comprising a solvent; and an ester having a chemical structure chosen from (I), (II), or (III);
wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group, wherein R1 is a saturated or unsaturated group having from 1-4 carbon atoms, R2 is chosen from hydrogen or a saturated or unsaturated group having from 1-4 carbon atoms, R3 is a saturated or unsaturated group having from 1-4 carbon atoms, and R4 is a saturated or unsaturated group having from 1-4 carbon atoms, and A− is an anion.

### Claim 2 (depends on 1)

The composition of matter of claim 1, wherein at least one of X or Y comprises a tert-butyl carbonate group.

### Claim 3 (depends on 1)

The composition of matter of claim 1, wherein at least one of X or Y comprises
-(alkyl)j-(aryl)k-(O)p-(COO)q-LG
wherein i, j, k, p, and q take the values in the following table:
-alkyl-
-aryl-
—O—
—COO—
j
k
p
q
1
1
1
1
1
1
0
1
1
1
1
0
1
0
0
1
1
0
1
0
0
1
1
1
0
1
0
1
0
1
1
0
0
0
0
1
wherein alkyl is a branched or unbranched, substituted or unsubstituted divalent alkyl chain of 1-16 carbon atoms having 0-16 heteroatoms substituted into the chain, aryl is a substituted or unsubstituted divalent phenyl group, divalent heteroaromatic group, or divalent fused aromatic or fused heteroaromatic group, and wherein LG is a leaving group.

### Claim 4 (depends on 3)

The composition of matter of claim 3, wherein the leaving group is a tert-butyl group, a tert-pentyl group, a 2,3-dimethylbutan-2-yl group, a 2,3,3-trimethylbutan-2-yl group, a 2,3-dimethylpentan-3-yl group, a 2-methylbicyclo[2.2.1]heptan-2-yl group, a bicyclo[2.2.1]heptan-2-yl group, a 1-methylcyclopentyl group, a 1-ethylcyclopentyl group, a 1-methylcyclohexyl group, a 1-ethylcyclohexyl group, a 2-methyladamantyl group, or a 2-ethyladamantyl group.

### Claim 5 (depends on 1)

The composition of matter of claim 1, further comprising, in admixture, one or more photoacid generators chosen from a sulfonium salt, an iodonium salt, a sulfone imide, a halogen-containing compound, a sulfone compound, an ester sulfonate compound, a diazomethane compound, a dicarboximidyl sulfonic acid ester, an ylideneaminooxy sulfonic acid ester, a sulfanyldiazomethane, or a mixture thereof.

### Claim 6 (depends on 5)

The composition of matter of claim 5, further comprising at least one crosslinker, wherein the at least one crosslinker comprises an acid sensitive monomer or polymer, and wherein the at least one crosslinker comprises at least one of a glycidyl ether, glycidyl ester, glycidyl amine, a methoxymethyl group, an ethoxy methyl group, a butoxymethyl group, a benzyloxymethyl group, dimethylamino methyl group, diethylamino methyl group, a dibutoxymethyl group, a dimethylol amino methyl group, diethylol amino methyl group, a dibutylol amino methyl group, a morpholino methyl group, acetoxymethyl group, benzyloxy methyl group, formyl group, acetyl group, vinyl group, or an isopropenyl group.

### Claim 7 (depends on 6)

The composition of matter of claim 6, wherein the at least one crosslinker comprises one or more glycidyl ether groups attached to a novolac resin.

### Claim 8

A composition of matter comprising: a solvent; and an ester having a chemical structure chosen from (IV), (V), or (VI);
wherein m=1-4, n=1-4, and wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group, and wherein A− is an anion.

### Claim 9 (depends on 8)

The composition of matter of claim 8, wherein at least one of X or Y comprises a tert-butylcarbonate group.

### Claim 10 (depends on 8)

The composition of matter of claim 8, wherein at least one of X or Y has the structure
-E-Op-(COO)q-LG
wherein E is an optional extender group, LG is a leaving group and p and q take values chosen from the following table:
(—E—)
(—O—)
(—COO—)
Present
p
q
Present
1
1
Present
0
1
Present
1
0
Not Present
0
1.

### Claim 11 (depends on 8)

The composition of matter of claim 8, wherein LG is a tert-butyl group.

### Claim 12 (depends on 8)

The composition of matter of claim 8, wherein LG is chosen from a tertiary alkyl or cycloalkyl group, a ketal or cyclic aliphatic ketal, or an acetal.

### Claim 13 (depends on 8)

The composition of matter of claim 8, wherein at least one of X or Y comprises
-(alkyl)j-(aryl)k-(O)p-(COO)q-LG
wherein j, k, p, and q take the values in the following table:
-alkyl-
-aryl-
—O—
—COO—
j
k
p
q
1
1
1
1
1
1
0
1
1
1
1
0
1
0
0
1
1
0
1
0
0
1
1
1
0
1
0
1
0
1
1
0
0
0
0
1
wherein alkyl is a branched or unbranched, substituted or unsubstituted divalent alkyl chain of 1-16 carbon atoms having 0-16 heteroatoms substituted into the chain, aryl is a substituted or unsubstituted divalent phenyl group, divalent heteroaromatic group, or divalent fused aromatic or fused heteroaromatic group, and wherein LG is a leaving group.

### Claim 14 (depends on 13)

The composition of matter of claim 13, wherein m=2 and n=3, and wherein the leaving group is a tert-butyl group.

### Claim 15 (depends on 14)

The composition of matter of claim 14, wherein LG is chosen from a tertiary alkyl or cycloalkyl group, a ketal or cyclic aliphatic ketal, or an acetal.

### Claim 16 (depends on 14)

The composition of matter of claim 14, wherein LG is a tert-butyl group, a tert-pentyl group, a 2,3-dimethylbutan-2-yl group, a 2,3,3-trimethylbutan-2-yl group, a 2,3-dimethylpentan-3-yl group, a 2-methylbicyclo[2.2.1]heptan-2-yl group, a bicyclo[2.2.1]heptan-2-yl group, a 1-methylcyclopentyl group, a 1-ethylcyclopentyl group, a 1-methylcyclohexyl group, a 1-ethylcyclohexyl group, a 2-methyladamantyl group, or a 2-ethyladamantyl group.

### Claim 17 (depends on 14)

The composition of matter of claim 14, further comprising, in admixture, one or more photoacid generators chosen from a sulfonium salt, an iodonium salt, a sulfone imide, a halogen-containing compound, a sulfone compound, an ester sulfonate compound, a diazomethane compound, a dicarboximidyl sulfonic acid ester, an ylideneaminooxy sulfonic acid ester, a sulfanyldiazomethane, or a mixture thereof.

### Claim 18 (depends on 8)

The composition of matter of claim 8, further comprising, in admixture, one or more photoacid generators chosen from a sulfonium salt, an iodonium salt, a sulfone imide, a halogen-containing compound, a sulfone compound, an ester sulfonate compound, a diazomethane compound, a dicarboximidyl sulfonic acid ester, an ylideneaminooxy sulfonic acid ester, a sulfanyldiazomethane, or a mixture thereof.

### Claim 19 (depends on 18)

The composition of matter of claim 18, further comprising at least one crosslinker, wherein the at least one crosslinker comprises an acid sensitive monomer or polymer, and wherein the at least one crosslinker comprises at least one of a glycidyl ether, glycidyl ester, glycidyl amine, a methoxymethyl group, an ethoxy methyl group, a butoxymethyl group, a benzyloxymethyl group, dimethylamino methyl group, diethylamino methyl group, a dibutoxymethyl group, a dimethylol amino methyl group, diethylol amino methyl group, a dibutylol amino methyl group, a morpholino methyl group, acetoxymethyl group, benzyloxy methyl group, formyl group, acetyl group, vinyl group, or an isopropenyl group.

### Claim 20 (depends on 18)

The composition of matter of claim 18, wherein the at least one crosslinker comprises one or more glycidyl ether groups attached to a novolac resin.