Photoacid generator and photoresist comprising same

Patent metadata

Field	Value
Publication number	US-9146470-B2
Application number	US-201414532134-A
Country	US
Kind code	B2
Filing date	Nov 4, 2014
Priority date	Sep 30, 2011
Publication date	Sep 29, 2015
Grant date	Sep 29, 2015

Abstract

A photoacid generator compound has the formula (I):

[A-(CHR 1 ) p ] k -(L)-(CH 2 ) m —(C(R 2 ) 2 ) n SO 3 − Z +   (I)

wherein A is a substituted or unsubstituted, monocyclic, polycyclic, or fused polycyclic C 5 or greater cycloaliphatic group optionally comprising O, S, N, F, or a combination comprising at least one of the foregoing, R 1 is H, a single bond, or a substituted or unsubstituted C 1-30 alkyl group, wherein when R 1 is a single bond, R 1 is covalently bonded to a carbon atom of A, each R 2 is independently H, F, or C 1-4 fluoroalkyl, wherein at least one R 2 is not hydrogen, L is a linking group comprising a sulfonate group, a sulfonamide group, or a C 1-30 sulfonate or sulfonamide-containing group, Z is an organic or inorganic cation, p is an integer of 0 to 10, k is 1 or 2, m is an integer of 0 or greater, and n is an integer of 1 or greater. A precursor compound to the photoacid generator, a photoresist composition including the photoacid generator, and a substrate coated with the photoresist composition, are also disclosed.

First claim

The invention claimed is:

1. A method of forming an electronic device comprising:
(a) applying a layer of a photoresist composition on a surface of a substrate;
(b) patternwise exposing the photoresist composition layer to activating radiation; and
(c) developing the exposed photoresist composition layer to provide a resist relief image,
wherein the photoresist composition comprises:
an acid-sensitive polymer, and
a compound having the formula (I):
[A-(CHR 1 ) p ] k -(L)-(CH 2 ) m —(C(R 2 ) 2 ) n SO 3 − Z +   (I)

wherein
A is a substituted or unsubstituted, polycyclic, or fused polycyclic C 5 or greater cycloaliphatic group optionally comprising O, S, N, F, or a combination comprising at least one of the foregoing,
R 1 is H, a single bond, or a substituted or unsubstituted C 1-30 alkyl group, wherein when R 1 is a single bond, R 1 is covalently bonded to a carbon atom of A,
each R 2 is independently H, F, or C 1-4 fluoroalkyl, wherein at least one R 2 is not hydrogen,
L is a linking group comprising a sulfonate group, a sulfonamide group, or a C 1-30 sulfonate or sulfonamide-containing group,
Z + is an organic or inorganic cation, and
p is an integer of 0 to 10, k is 1 or 2, m is an integer of 2-10, and n is an integer of 1 to 10.

2. The method of claim 1 , wherein the compound having the formula (I) has the formula (IIa) or (IIb):
A-(CHR 1 ) p —O—SO 2 —(CH 2 ) m —(C(R 2 ) 2 ) n —SO 3 − Z +   (IIa)

A-(CHR 1 ) p —SO 2 —O—(CH 2 ) m —(C(R 2 ) 2 ) n —SO 3 − Z +   (IIb)

wherein A, R 1 , R 2 p, m, n, and Z + are as defined for formula (I).

3. The method of claim 1 , wherein the compound having the formula (I) has the formula (IIIa) or (IIIb):
A-(CHR 1 ) p —N(R 3 )—SO 2 —(CH 2 ) m —(C(R 2 ) 2 ) n —SO 3 − Z +   (IIIa)

A-(CHR 1 ) p —SO 2 —N(R 3 )—(CH 2 ) m —(C(R 2 ) 2 ) n —SO 3 − Z +   (IIIb)

wherein A, R 1 , R 2 p, m, n, and Z + are as defined for formula (I), and R 3 is H, a C 1-20 alkyl group, or A-(CHR 1 ) p —.

4. The method of claim 1 , wherein the compound having the formula (I) has the formula (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), or (XII):

wherein Z + is as defined in formula (I).

5. The method of claim 1 , wherein Z + is a cation of the formula (XIII)

wherein R 4 and R 5 are independently substituted or unsubstituted C 1-20 alkyl, C 1-20 fluoroalkyl, C 3-20 cycloalkyl, C 3-20 fluorocycloalkyl, C 2-20 alkenyl, C 2-20 fluoroalkenyl, C 6-20 aryl, C 6-20 fluoroaryl, C 5-20 heteroaryl, C 7-20 aralkyl, C 7-20 fluoroaralkyl, C 6-20 heteroaralkyl, where R 4 and R 5 are separate or connected by a single bond, and Ar is a C 5-30 aromatic-containing group.

6. The method of claim 5 , wherein the cation is of the formula (XIV), (XV), or (XVI):

wherein
R 4 and R 5 are independently substituted or unsubstituted C 1-20 alkyl, C 1-20 fluoroalkyl, C 3-20 cycloalkyl, C 3-20 fluorocycloalkyl, C 2-20 alkenyl, C 2-20 fluoroalkenyl, C 6-20 aryl, C 6-20 fluoroaryl, C 5-20 heteroaryl, C 7-20 aralkyl, C 7-20 fluoroaralkyl, or C 6-20 heteroaralkyl, where R 4 and R 5 are separate or connected by a single bond;
R 6 , R 7 , R 8 and R 9 are each independently H, a halogen, C 1-20 alkyl, C 1-20 fluoroalkyl, C 1-20 alkoxy, C 1-20 fluoroalkoxy, C 1-20 thioalkoxy, C 1-20 fluorothioalkoxy, C 1-20 alkoxycarbonyl, C 1-20 fluoroalkoxycarbonyl, C 1-20 thioalkoxycarbonyl, C 1-20 fluorothioalkoxycarbonyl, C 3-20 cycloalkyl, C 3-20 fluorocycloalkyl, C 3-20 cycloalkoxy, C 3-20 fluorocycloalkoxy, C 2-20 alkenyl, C 2-20 fluoroalkenyl, C 6-20 aryl, C 6-20 fluoroaryl, C 6-20 aryloxy, C 6-20 fluoroaryloxy, C 5-20 heteroaryl, C 5-20 heteroaryloxy, C 5-20 heteroaryloxy, C 7-20 aralkyl, C 7-20 fluoroaralkyl, C 7-20 aralkyloxy C 7-20 fluoroaralkyloxy, or C 6-20 heteroaralkyl, or C 6-20 heteroaralkyloxy, wherein R 6 , R 7 , R 8 and R 9 are each independently unsubstituted or further substituted to include an acid-labile group, a base-labile group, or a base-soluble group, and
q is an integer of 1 to 5, r is an integer of 0 to 3, s is an integer of 0 to 4, t is an integer of 0 to 4, and a is an integer of 0 to 4.

7. The method of claim 6 , wherein Z + is of the formula (XVII), (XVIII), (XIX), or (XX):

wherein
R 10 , R 11 , R 12 and R 14 are independently H, a halogen, C 1-10 alkyl, C 1-10 fluoroalkyl, C 1-10 alkoxy, C 1-10 fluoroalkoxy, C 3-10 cycloalkyl, C 3-10 fluorocycloalkyl, C 3-10 cycloalkoxy, or C 3-10 fluorocycloalkoxy,
R 13 is H, C 1-10 alkyl, C 1-10 fluoroalkyl, C 3-10 cycloalkyl, or C 3-10 fluorocycloalkyl, and
a and b are each independently 1 or 2.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Aqad Emad
• Xu Cheng-Bai
• Li Mingqi
• Yamada Shintaro
• Williams Iii William

Classifications

• C07D313/08 Primary

  condensed with one six-membered ring · CPC title

• C07C2103/74

  Chemistry & Metallurgy · mapped topic

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title

• C07D313/10

  condensed with two six-membered rings · CPC title

• G03F7/30 Primary

  Imagewise removal using liquid means · CPC title