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

Patent metadata

Field	Value
Publication number	US-11550217-B2
Application number	US-201615387788-A
Country	US
Kind code	B2
Filing date	Dec 22, 2016
Priority date	Dec 31, 2015
Publication date	Jan 10, 2023
Grant date	Jan 10, 2023

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

The invention claimed is:

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

wherein:
each EWG is independently chosen from —CN, —NO 2 , —C(═O)R 21 , —C(═O)OR 22 , or —SO 2 R 23 , wherein R 21 , R 22 , or R 23 are each independently a C 1-30 aliphatic organic group, a C 6-30 aromatic organic group, or a C 1-30 heteroaromatic organic 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. A photoresist composition comprising:
an acid-sensitive polymer,
a solvent, and
a photoacid generator compound having Formula (III):

wherein:
X 5 and X 6 are each independently an electron withdrawing group selected from C(NO 2 ) 2 , C(COR 21 ) 2 , C(CO 2 R 22 ) 2 , C(SO 2 R 23 ) 2 , and C(R f ) 2 , wherein R 21 , R 22 , and R 23 are each independently a C 1-30 aliphatic organic group, a C 6-30 aromatic organic group, or a C 1-30 heteroaromatic organic group, and 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 is a single bond or a linking group;
R is 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 is substituted or unsubstituted, and
M + is an organic cation.

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

wherein in Formula (III):
X 5 and X 6 are each C(CN) 2 ;
Z 1 and Z 2 are each independently hydrogen, a straight chain C 1-50 alkyl group, a branched C 3-50 alkyl group, a monocyclic C 3-50 cycloalkyl group, a polycyclic C 7-50 cycloalkyl group, a monocyclic or polycyclic C 3-50 heterocycloalkyl group; a monocyclic C 6-50 aryl group, a polycyclic C 10-50 aryl group, a monocyclic or polycyclic C 5-20 heteroaryl group, or a combination thereof;
R is 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 is substituted or unsubstituted;
Y is a single bond or a linking group; and
M + is an organic cation.

4. The photoresist composition of claim 2 , wherein in Formula (III):
Y is a single bond.

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

wherein,
X 5 and X 6 are each independently an electron withdrawing group selected from 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 27 , R 28 , and R 29 are each independently a C 1-30 aliphatic organic group, a C 6-30 aromatic organic group, or a C 1-30 heteroaromatic organic group, and wherein R f is a C 1 -C 30 fluoroalkyl group;
M + is an organic cation;
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═

Assignees

• Rohm & Haas Elect Mat

Inventors

• Aqad Emad
• Williams Iii William
• Cameron James F

Classifications

• C07C255/31

  having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings · CPC title

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• C07C25/18

  Polycyclic aromatic halogenated hydrocarbons · CPC title

• C07C2603/74

  Adamantanes · CPC title

• G03F7/322

  Aqueous alkaline compositions · CPC title