Photoacid generators and photoresists comprising same

Patent metadata

Field	Value
Publication number	US-9348220-B2
Application number	US-201113077943-A
Country	US
Kind code	B2
Filing date	Mar 31, 2011
Priority date	Mar 31, 2010
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

New methods are provided for synthesis of photoacid generator compounds (“PAGs”), new photoacid generator compounds and photoresist compositions that comprise such PAG compounds. In a particular aspect, photoacid generators that comprise 1) a SO 3 − moiety; 2) one or more fluorinated carbons; and 3) one or more of the fluorinated carbons either directly or indirectly substituted by an ester keto group.

First claim

What is claimed is:

1. A photoacid generator compound that comprises a structure of the following formula (I):
RO(C═O)(CXY) p (CF 2 ) n SO 3 − M +   (I)

wherein R is hydrogen or non-hydrogen substituent;
X and Y are each independently hydrogen or a non-hydrogen substituent;
p is a positive integer;
n is a positive integer;
M+ is a counter ion.

2. A photoacid generator compound of claim 1 that comprises a structure of the following formula (II):
RO(C═O)(CH 2 ) p (CF 2 ) n SO 3 − M +   (II).

3. A photoacid generator of claim 1 wherein the sum of p and n is at least four.

4. A photoacid generator of claim 1 wherein R is a carbon alicylic or heteroalicylic group.

5. A photoacid generator of claim 1 wherein M+ is a sulfonium or iodonium cation.

6. A photoacid generator compound of claim 1 wherein the photoacid generator compound comprises a structure selected from the following:

7. A photoacid generator compound of claim 1 wherein the photoacid generator compound comprises a structure selected from the following:

8. A photoresist composition comprising a resin component and a photoacid generator compound of claim 6 .

9. A method for forming a photoresist relief image comprising:
a) applying a coating layer of a photoresist composition of claim 8 on a substrate;
b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

10. A photoresist composition comprising a resin component and a photoacid generator compound of claim 7 .

11. A method for forming a photoresist relief image comprising:
a) applying a coating layer of a photoresist composition of claim 10 on a substrate;
b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

12. A photoresist composition comprising a resin component and a photoacid generator compound of claim 1 .

13. A method for forming a photoresist relief image comprising:
a) applying a coating layer of a photoresist composition of claim 12 on a substrate;
b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

Assignees

• Aqad Emad
• Li Mingqi
• Xu Cheng-Bai
• Liu Cong
• Rohm & Haas Elect Mat

Inventors

• Aqad Emad
• Li Mingqi
• Xu Cheng-Bai
• Liu Cong

Classifications

• C07D313/00

  Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom · CPC title

• G03F7/0395

  the macromolecular compound having a backbone with alicyclic moieties · CPC title

• G03F7/0382

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• C07C309/19

  of a saturated carbon skeleton containing rings · CPC title