US 9,951,164 B2 · Non-ionic aryl ketone based polymeric photo-acid generators

Abstract

Non-ionic photo-acid generating (PAG) polymerizable monomers were prepared that contain a side chain sulfonate ester of an alpha-hydroxy aryl ketone. The aryl ketone group has a perfluorinated substituent alpha to the ketone carbonyl. The sulfur of the sulfonate ester is also directly linked to a fluorinated group. PAG polymers prepared from the PAG monomers release a strong 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.

Claims25

Dependent claims

A compound of formula (1):

wherein
Ar is a monovalent radical comprising one or more aromatic rings,
L′ is a single bond or a divalent C0-C10 linking group,
P′ is a C2-C20 monovalent radical comprising a polymerizable carbon-carbon double bond,
R1 is a monovalent perfluorinated C1-C10 radical, wherein R1 has a molecular formula consisting of elements carbon and fluorine, and
Z′ is a divalent C1-C10 radical having a molecular formula consisting of elements carbon, fluorine, and optionally hydrogen.

3 more elements

Dependencies are inferred from the claim text.

Facts

Application

15/235,673Filed 12 Aug 2016

Published

US 2018/0044459 A115 Feb 2018

Granted

24 Apr 2018

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

C08F 220/20
Esters: of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl acrylate or glycerol mono-acrylate
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 309/69
Having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms: of a carbon skeleton substituted by nitrogen atoms, not being part…
C07C 309/70
Having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms: of a carbon skeleton substituted by carboxyl groups

Non-ionic aryl ketone based polymeric photo-acid generators

Life of this patent

Non-ionic aryl ketone based polymeric photo-acid generators

Life of this patent

Abstract

Claims25