Photoresist composition, coated substrate including the photoresist composition, and method of forming electronic device

Patent metadata

Field	Value
Publication number	US-2017192353-A1
Application number	US-201615387788-A
Country	US
Kind code	A1
Filing date	Dec 22, 2016
Priority date	Dec 31, 2015
Publication date	Jul 6, 2017
Grant date	—

Abstract

A photoresist composition, including an acid-sensitive polymer and photoacid generator compound having Formula (I):

wherein, EWG, Y, R, and M + are the same as described in the specification.

First claim

1 . A photoresist composition, comprising:
an acid-sensitive polymer, a solvent, and a photoacid generator compound having Formula (I):

wherein:
EWG is an electron-withdrawing group;
Y is a single bond or a linking group;
R is hydrogen, a straight chain or branched C 1-20 alkyl group, a straight chain or branched C 2-20 alkenyl group, a monocyclic or polycyclic C 3-20 cycloalkyl group, a monocyclic or polycyclic C 3-20 cycloalkenyl group, a monocyclic or polycyclic C 3-20 heterocycloalkyl group; a monocyclic or polycyclic C 3-20 heterocycloalkenyl group; a monocyclic or polycyclic C 6-20 aryl group, or a monocyclic or polycyclic C 1-20 heteroaryl group, each of which except hydrogen is substituted or unsubstituted, wherein when R comprises a polymerizable group, the photoacid generator is a polymerized unit of the acid-sensitive polymer; and
M + is an organic cation.

2 . The photoresist composition of claim 1 , wherein the photoacid generator compound has Formulae (II) or (III):

wherein:
X 1 , X 2 , X 3 and X 4 are each independently an electron-withdrawing group;
X 5 and X 6 are each independently an electron withdrawing group selected from C(CN) 2 , C(NO 2 ) 2 , C(COR 27 ) 2 , C(CO 2 R 28 ) 2 , C(SO 2 R 29 ) 2 , and C(R f ) 2 , wherein R f is a C 1 -C 30 fluoroalkyl group;
Z 1 and Z 2 are each independently hydrogen, a straight chain or branched C 1-50 alkyl group, a monocyclic or polycyclic C 3-50 cycloalkyl group, a monocyclic or polycyclic C 3-50 heterocycloalkyl group; a monocyclic or polycyclic C 6-50 aryl group, a monocyclic or polycyclic C 5-20 heteroaryl group, or a combination thereof, wherein groups Z 1 and Z 2 are optionally connected to each other to form a ring;
Y, R, and M are the same as in claim 1 ; and
each “ ” represents a partial double bond.

3 . The photoresist composition of claim 2 , wherein in Formula (III):
EWG is CN; R is a polycyclic C 3-20 cycloalkyl group; Y is a single bond, —C(R 30 ) 2 —, —N(R 31 )—, —O—, —S—, —S(═O) 2 —, —(C═O)—, or a combination thereof, wherein each R 30 and R 31 is independently hydrogen or a C 1-6 alkyl group; and M + is an organic sulfonium cation or an organic iodonium cation.

4 . The photoresist composition of claim 2 , wherein in Formula (III):
X 5 and X 6 are each C(CN) 2 ; R is hydrogen; and Y is a single bond.

5 . The photoresist composition of claim 1 , having Formula (IV):

wherein,
X 5 , X 6 , and M + are the same as in claim 2 ;
R 1 is a halogen, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, a C 3-10 fluorocycloalkoxy group, or an electron-withdrawing group selected from NO 2 , CN, C(R f ) 3 or CO 2 R, wherein R f is a C 1 -C 30 fluoroalkyl group; and
k is an integer of 0, 1, 2, 3, or 4.

6 . The photoresist composition of claim 1 , wherein M + is an organic cation having Formula (V):

wherein,
each R 2 is independently a C 1-20 alkyl group, a C 1-20 fluoroalkyl group, a C 3-20 cycloalkyl group, a C 3-20 fluorocycloalkyl group, a C 2-20 alkenyl group, a C 2-20 fluoroalkenyl group, a C 6-20 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a C 7-20 aralkyl group, a C 7-20 fluoroaralkyl group, a C 2-20 heteroaralkyl group, or a C 2-20 fluoroheteroaralkyl group, each of which is substituted or unsubstituted,
wherein each R 2 is either separate or connected to the other group R 2 via a single bond or a linking group, and
Ar is a substituted or unsubstituted C 6-30 aromatic organic group.

7 . The photoresist composition of claim 1 , wherein M + is an organic cation having Formula (VI):

wherein
X is I or S;
each R 3 is independently a halogen, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, a C 3-10 fluorocycloalkoxy group, or a C 6-10 alkoxycarbonylalkyleneoxy group;
each n is an integer of 0, 1, 2, 3, 4, and 5; and
m is an integer of 2 or 3, provided that when X is I, m is 2, and where X is S, m is 3.

8 . The photoresist composition of claim 1 , wherein M + is an organic cation having Formulae (VII) or (VIII):

wherein
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each independently a halogen, —CN, —OH, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, or a C 3-10 fluorocycloalkoxy group, each of which except a halogen, —CN, and —OH is substituted or unsubstituted;
J is a single bond or a connecting group selected from S, O, and C═O,
p is each independently an integer of 0, 1, 2, 3, or 4;
r is an integer of 0, 1, 2, 3, 4, and 5, and
s and t are each independently an integer of 0, 1, 2, 3, and 4.

9 . The photoresist composition of claim 1 , wherein R comprises a polymerizable group, and wherein the photoacid generator is a polymerized unit of the acid-sensitive polymer.

10 . A coated substrate, comprising: (a) a substrate having one or more layers to be patterned on a surface thereof; and (b) a layer of the photoresist composition of claim 1 over the one or more layers to be patterned.

11 . A method of forming an electronic device, comprising: (a) applying a layer of the 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 resist relief image.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Aqad Emad
• Williams Iii William
• Cameron James F

Classifications

• G03F7/162

  Coating on a rotating support, e.g. using a whirler or a spinner · CPC title

• C07C2602/08

  the other ring being five-membered, e.g. indane · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/0397

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

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title