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US 10,310,375 B2Granted
Photoacid generators and lithographic resists comprising the same
OwnerKenneth E Gonsalves, Mingxing Wanginventors
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Abstract
The present invention provides photoacid generators for use in chemically amplified resists and lithographic processes using the same.
Claims9
A cationic photoacid generator having the formula:
An acid amplifier having the formula:
An acid amplifier having the formula:
- wherein R is selected from the group consisting of -halo, -fluoroalkyl and —NO2.
A lithographic resist comprising a photoacid generator of Formula (II):
- wherein
- R1 is selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -alkynyl, -cycloalkyl, -aryl, -heteroaryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, —O-alkylene-arylene-alkyl, —O-alkylene-arylene-alkenyl, —OC(O)-alkyl, —OC(O)-alkenyl, —O— alkylene-O-alkenyl, and —OH;
- R2 is selected from the group consisting of arylene, heteroarylene and polycyclic;
- R3, R4, R5 and R6 are independently selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -alkynyl, -cycloalkyl, -aryl, -heteroaryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-heteroaryl, —O-alkylene-aryl, —O-alkylene-arylene-alkyl, —O-alkylene-arylene-alkenyl;
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and heteroaryl of R1 and R3-R6 are optionally and independently substituted one or more times with a substituent selected from the group consisting of -alkyl, -alkenyl, -alkynyl, cycloalkyl, -aryl, heteroaryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, -carboxyl, -hydroxyl, -halo, and -nitro;
- and
- X− is selected from the group consisting of CF3SO3−, C4F9SO3− and an anionic photoacid generator wherein the counter cation is not present;
- and
- an acid amplifier of Formula (III)
- wherein
- R1 and R2, R3, R4, R5, R6, R7, R8, R9, R10 and R12 are independently selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -alkynyl, -cycloalkyl, -fluoroalkyl, -fluoroalkenyl, -fluoroalkynyl, -aryl, -heteroaryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, —O-alkylene-arylene-alkyl, —O-alkylene-arylene-alkenyl, —OC(O)-alkyl, —OC(O)-alkenyl, -carboxyl, -hydroxyl, -halo, -cyano and -nitro,
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, aryl and heteroaryl groups of R1-R8 are optionally and independently substituted one of more times with a substituent selected from the group consisting of -alkyl, -alkenyl, -fluoroalkyl, -fluoroalkyl, -aryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, —OC(O)-alkyl, —OC(O)-alkenyl, -carboxyl, -hydroxyl, -halo, and nitro, and
- wherein the lithographic resist of Formula (II) is copolymerized with the acid amplifier of Formula (III).
10 more elements
A lithographic resist comprising a photoacid generator of Formula (II):
- wherein:
- R1 is selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -alkynyl, -cycloalkyl, -aryl, -heteroaryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, —O-alkylene-arylene-alkyl, —O-alkylene-arylene-alkenyl, —OC(O)-alkyl, —OC(O)-alkenyl, —O-alkylene-O-alkenyl, and —OH;
- R2 is selected from the group consisting of arylene, heteroarylene and polycyclic;
- R3, R4, R5 and R6 are independently selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -alkynyl, -cycloalkyl, -aryl, -heteroaryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-heteroaryl, —O-alkylene-aryl, —O-alkylene-arylene-alkyl, —O-alkylene-arylene-alkenyl;
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and heteroaryl of R1 and R3-R6 are optionally and independently substituted one or more times with a substituent selected from the group consisting of -alkyl, -alkenyl, -alkynyl, cycloalkyl, -aryl, heteroaryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, -carboxyl, -hydroxyl, -halo, and -nitro;
- and
- X− is selected from the group consisting of CF3SO3−, C4F9SO3− and an anionic photoacid generator wherein the counter cation is not present;
- and
- an acid amplifier of Formula (III):
- wherein:
- R1 and R2, R3, R4, R5, R6, R7, R8, R9, R10 and R12 are independently selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -alkynyl, -cycloalkyl, -fluoroalkyl, -fluoroalkenyl, -fluoroalkynyl, -aryl, -heteroaryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, —O-alkylene-arylene-alkyl, —O-alkylene-arylene-alkenyl, —OC(O)-alkyl, —OC(O)-alkenyl, -carboxyl, -hydroxyl, -halo, -cyano and -nitro,
- wherein the alkyl, alkenyl, alkynyl, cycloalkyl, aryl and heteroaryl groups of R1-R8 are optionally and independently substituted one of more times with a substituent selected from the group consisting of -alkyl, -alkenyl, -fluoroalkyl, -fluoroalkyl, -aryl, —O-alkyl, —O-alkenyl, —O-aryl, —O-alkylene-aryl, —OC(O)-alkyl, —OC(O)-alkenyl, -carboxyl, -hydroxyl, -halo, and -nitro;
- and
- further comprising an energy harvesting unit, wherein the energy harvesting unit comprises a conjugated polymer.
11 more elements
Dependencies are inferred from the claim text.