US 9,983,475 B2 · Fluorinated sulfonate esters of aryl ketones for non-ionic photo-acid generators

Abstract

Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group having a perfluorinated substituent alpha to the ketone carbonyl. The non-polymeric PAGs release a sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs can also undergo a thermal reaction to form a sulfonic acid. The perfluorinated substituent provides improved thermal stability and hydrolytic/nucleophilic stability.

Claims24

Dependent claims

A compound of formula (3):

wherein
n is a positive integer having a value of 1-4,
Ar is a monovalent aryl radical comprising one or more aromatic rings,
L′ is a single bond or a divalent C1-C10 linking group,
R1 is a monovalent perfluorinated C1-C10 radical, wherein R1 has a molecular formula consisting of elements carbon and fluorine, and
R2 is a C1-C50 radical having a valency of n.

3 more elements

Dependencies are inferred from the claim text.

Facts

Application

15/235,410Filed 12 Aug 2016

Published

US 2018/0046077 A115 Feb 2018

Granted

29 May 2018

Term ends

Not estimatedThe source records don’t support an estimate.

Classification23 codes

G03F 7/0045
Photosensitive materials: with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
C07C 309/68
Having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms: of a carbon skeleton substituted by singly-bound oxygen atoms
C07C 309/70
Having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms: of a carbon skeleton substituted by carboxyl groups
C07C 309/77
Having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton: containing carboxyl…

Fluorinated sulfonate esters of aryl ketones for non-ionic photo-acid generators

Life of this patent

Fluorinated sulfonate esters of aryl ketones for non-ionic photo-acid generators

Life of this patent

Abstract

Claims24