US 6,319,649 B1Granted

Photosensitive resin composition and method of forming resist images

AssigneesHitachi, Ltd., Hitachi Chemical Company, Ltd.

InventorsKoji Kato, Masahiro Hashimoto, Michiaki Hashimoto, Toshio Sakamizu, Hiroshi Shiraishi

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Abstract

A chemically amplified photosensitive resin composition containing a first compound forming an acid by irradiation of actinic ray and a second compound that changes the solubility to an aqueous alkali solution with acid-catalyzed reaction wherein an ion dissociative compound having the composition represented by the general formula (1) or (2), as well a method of forming a resist pattern using the composition are disclosed, the formulae being expressed by: where each of R2, R3 and R4 represents hydrogen, and an alkyl or aryl group of 1 to 7 carbon atoms, at least one of R1, R2, R3 and R4 represents hydrogen, Y1 represents chlorine, bromine, iodine, carbonate group of 1 to 7 carbon atoms or sulfonate group of 1 to 7 carbon atoms, and

Claims20

Dependent claims

A chemically amplified photosensitive resin composition containing a first compound that generates an acid by irradiation of an actinic ray and a second compound that changes solubility to an aqueous alkali solution with an acid-catalyzed reaction, wherein at least one of an ion dissociative compound represented by the general formula (1) and an ion dissociative compound represented by the general formula (2) is incorporated, said at least one of an ion dissociative compound being at least one compound controlling the acid generated from the first compound by the irradiation of the actinic ray and diffusion of the acid from irradiated areas of the photosensitive resin composition, and stabilizing the photosensitive resin composition and resist film formed therefrom, said formulae being expressed by:

wherein each of R1, R2, R3 and R4 represents hydrogen, and an alkyl group of 1 to 7 carbon atoms or an aryl group, at least one of R1, R2, R3 and R4 represents hydrogen, and Y1 represents chlorine, bromine, iodine, a carbonate group of 1 to 7 carbon atoms or a sulfonate group of 1 to 7 carbon atoms, and
wherein each of R5, R6 and R7 represents hydrogen, and an alkyl group of 1 to 7 carbon atoms or an aryl group, and Y2 represents chlorine, bromine, iodine, or a carbonate group of 1 to 7 carbon atoms.

A method of forming a pattern including the following steps:

a step of forming a chemically amplified photosensitive resin composition containing a first compound that generates an acid by irradiation of actinic ray and a second compound that changes the solubility to an aqueous alkali solution with acid-catalyzed reaction, wherein at least one of an ion dissociative compound general formula (1) or an ion dissociative compound general formula (2) is incorporated, said formulae being expressed by:
where each of R1, R2, R3 and R4 represents hydrogen, and an alkyl group of 1 to 7 carbon atoms or an aryl group, at least one of R1, R2, R3 and R4 represents hydrogen, Y1 represents chlorine, bromine, iodine, a carbonate group of 1 to 7 carbon atoms or a sulfonate group of 1 to 7 carbon atoms, and
where each of R5, R6 and R7 represents hydrogen, and an alkyl group of 1 to 7 carbon atoms or an aryl group, Y2 represents chlorine, bromine, iodine, or a carbonate group of 1 to 7 carbon atoms,
a step of dissolving the photosensitive resin composition in a solvent to form a solution,
a step of coating the solution on the surface of a substrate, thereby forming a resist film,
a step of irradiating actinic ray to a predetermined portion of the resist film thereby changing the solubility of the irradiated portion to an aqueous alkali solution, and
a step of developing the resist film with an aqueous alkali solution to form a predetermined resist pattern.

4 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/024,873Filed 17 Feb 1998 · continuation
Priority: JP 6-24765613 Oct 1994
Granted: 20 Nov 2001
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

G03F 7/0045
Photosensitive materials: with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
G03F 7/039
Photosensitive materials: macromolecular compounds which are photodegradable, e.g. positive electron resists
Y10S 430/106
Radiation sensitive composition or product or process of making: binder containing
Y10S 430/111
Binder containing: polymer of unsaturated acid or ester