# US 10,503,073 B2 · Photoresist compositions and methods

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- Number: US 10,503,073 B2
- Document ID: US10503073B2
- Status: Granted
- Kind: B2
- Application number: 15/142,549
- Filed: 2016-04-29
- Published: 2016-11-03
- Granted: 2019-12-10
- Earliest claimed: 2015-04-30
- Assignees: Rohm and Haas Electronic Materials Korea Ltd.
- Applicants: Rohm and Haas Electronic Materials Korea Ltd.
- Inventors: Eui-Hyun Ryu; Min-Kyung Jang; Chang-Young Hong; Dong-Yong Kim; Dong-Je Hong; Hae-Jin Lim; Myung Yeol Kim; Hyun Jeon
- Web page: https://patentgrep.com/patent/US10503073B2

## CPC

- G03F 7/325: {Non-aqueous compositions}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/2041: {in the presence of a fluid, e.g. immersion; using fluid cooling means}
- G03F 7/30: Imagewise removal using liquid means
- 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)

## Abstract

New photoresists are provided that are useful in a variety of applications, including negative-tone development processes. Preferred resists comprise a first polymer that comprises (i) first units comprising a nitrogen-containing moiety that comprises an acid-labile group; and (ii) second units that (1) comprise one or more hydrophobic groups and (2) are distinct from the first units.

## Claims

### Claim 1

A photoresist composition comprising:
(a) a first polymer comprising:
(i) first units comprising a nitrogen-containing moiety that comprises an acid-labile group;
(ii) second units that (1) comprise one or more hydrophobic groups and (2) are distinct from the first units,
(iii) third units that (1) comprise one or more hydrophobic groups and (2) are distinct from the first and second units, and wherein the first polymer is free of silicon or flourine;
(b) one or more acid generators; and
(c) a second polymer that (1) comprises acid-labile groups and (2) is distinct from the first polymer.

### Claim 2 (depends on 1)

The photoresist composition of claim 1 wherein the one or more hydrophobic groups of the second and third units each comprise three or more carbon atoms.

### Claim 3 (depends on 1)

The photoresist composition of claim 1 wherein the nitrogen-containing moiety is a protected amine.

### Claim 4 (depends on 1)

The photoresist composition of claim 1 wherein the nitrogen-containing moiety can be deprotected in the presence of acid during lithographic processing.

### Claim 5 (depends on 1)

The photoresist composition of claim 1 wherein the nitrogen-containing moiety is a carbamate or sulfamate.

### Claim 6 (depends on 1)

The photoresist composition of claim 1 wherein the (i) units comprising a nitrogen-containing moiety further comprise a hydrophobic group.

### Claim 7 (depends on 1)

The photoresist composition of claim 1 wherein the first polymer is substantially non-miscible with the second polymer.

### Claim 8 (depends on 7)

A method for forming a photolithographic pattern, comprising:
(a) applying a layer of a photoresist composition of claim 7 on a substrate;
(b) patternwise exposing the photoresist composition layer to activating radiation; and
(c) developing the exposed photoresist composition layer to provide a photoresist relief image.

### Claim 9 (depends on 8)

The method of claim 8 wherein the exposed photoresist composition layer is developed with an organic solvent composition that selectively removes unexposed portions of the photoresist composition layer to provide the photoresist relief image.

### Claim 10 (depends on 8)

The method of claim 8 where the photoresist composition layer is exposed to 193 nm radiation.

### Claim 11 (depends on 8)

The method of claim 8 wherein the photoresist composition layer is immersion exposed to activating radiation.

### Claim 12 (depends on 1)

A method for forming a photolithographic pattern, comprising:
(a) applying a layer of a photoresist composition of claim 1 on a substrate;
(b) patternwise exposing the photoresist composition layer to activating radiation; and
(c) developing the exposed photoresist composition layer to provide a photoresist relief image.

### Claim 13 (depends on 12)

The method of claim 12 wherein the exposed photoresist composition layer is developed with an organic solvent composition that selectively removes unexposed portions of the photoresist composition layer to provide the photoresist relief image.

### Claim 14 (depends on 12)

The method of claim 12 where the photresist composition layer is exposed to 193 nm radiation.

### Claim 15 (depends on 12)

The method of claim 12 where the photresist composition layer is exposed to EUV nm radiation.