Reagent and composition of resist

Patent metadata

Field	Value
Publication number	US-9618844-B2
Application number	US-201414891293-A
Country	US
Kind code	B2
Filing date	May 13, 2014
Priority date	May 13, 2013
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

Described is a reagent that enhances acid generation of a photoacid generator and a composition containing such reagent.

First claim

The invention claimed is:

1. A composition comprising:
a reagent;
a first compound that functions as a generation source of acid;
wherein a feed of an energy to the reagent or to an acceptor for the reagent receiving the energy generates an intermediate from the reagent;
wherein the intermediate enhances generation of acid from a precursor, wherein the intermediate is a ketyl radical;

wherein the reagent is selected from the group consisting of a first reagent, a second reagent and a third reagent;
wherein:
the first reagent is represented by formula (I);

wherein:
R 1 is a hydrogen atom;
R 2 is a phenyl group, an alkyl carbonyl group, an aryl carbonyl group, an alkyl group, an alkenyl group, an aralkyl group, an alkynyl group, an alkyl group containing a cyclic or poly cyclic moiety, or a substituent containing at least one atom other than carbon atom and hydrogen atom; and
R 3 is a hydrogen atom, a phenyl group, an alkyl carbonyl group, an aryl carbonyl group, an alkyl group, an alkenyl group, an aralkyl group, an alkynyl group, an alkyl group containing a cyclic or poly cyclic moiety, or a substituent containing at least one atom other than carbon atom and hydrogen atom;

the second reagent is represented by formula (II):

wherein:
Z is a carbonyl group, a methylene group, an alkoxymethylene, an aryloxymethylene, or a hydroxymethylene;
R 4 is an aryl group or an aryl group containing an aromatic group and a substituent on the aromatic group containing at least one atom other than carbon atom and hydrogen atom; and
R 5 is a hydrogen atom, a phenyl group, an alkyl carbonyl group, an aryl carbonyl group, an alkyl group, an alkenyl group, an aralkyl group, an alkynyl group, an alkyl group containing a cyclic or poly cyclic moiety, or a substituent containing at least one atom other than carbon atom and hydrogen atom;

the third reagent includes: a hydroxyl group; and

a first cyclic moiety that contains a carbon atom bonded to the hydroxyl group and a hydrogen atom.

2. The reagent composition of claim 1 , wherein the feed of energy comprises irradiation with light.

3. The composition of claim 1 , wherein the feed of energy is carried out by irradiation of the reagent with at least one of light of which the wavelength is less than or equal to 15 nm and an electron beam.

4. The composition of claim 3 , further comprising:
a second compound that has a bond cleavable by acid.

5. The composition of claim 1 , wherein:
the composition further includes a second cyclic moiety, and
the first cyclic moiety contains at least two atoms that are also contained in the second cyclic moiety.

6. The composition reagent of claim 5 , wherein:
the third reagent further includes a third cyclic moiety, and
the first cyclic moiety contains at least two atoms that are also contained in the third cyclic moiety.

7. The reagent composition of claim 1 , wherein the first cyclic moiety is either a six-membered ring or a five-membered ring.

8. The composition of claim 1 , wherein the second cyclic moiety is an aromatic group.

9. The composition of claim 1 , wherein the first compound is an organic salt containing an iodonium ion or a sulfonium ion.

10. The composition of claim 1 , wherein the intermediate is generated by abstracting a hydrogen atom from the reagent.

11. The composition of claim 1 , wherein a difference between at least one of a first oxidation potential of a ground state and a second oxidation potential of an excited state of the intermediate and at least one of a first reduction potential of the ground state and a second reduction potential of the excited state of the precursor is greater than or equal to 0.10 eV.

12. The composition of claim 11 , wherein the first reduction potential is lower than at least one of the first oxidation potential and the second oxidation potential.

13. A method of using the composition of claim 1 to manufacture a device, the method comprising:
applying a solution of the composition to a substrate such that a film including the composition is formed on the substrate; and
irradiating the film with at least one of an electromagnetic ray and a particle ray such that a first portion of the film is irradiated with the at least one of the electromagnetic ray and the particle ray while a second portion of the film is not irradiated with the at least one of the electromagnetic ray and the particle ray.

14. The method of claim 13 , further comprising:
removing the first portion.

15. The method of claim 14 , further comprising:
etching the substrate such that a third portion of the substrate on which the first portion has been present is etched.

16. The method of claim 13 , wherein irradiating the film is carried out using at least one of an EUV light and an electron beam.

Assignees

• Toyo Gosei Co Ltd
• Univ Osaka

Inventors

• Enomoto Satoshi

Classifications

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• C07D309/12

  only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers · CPC title

• G03F7/2037

  Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• C07C33/24

  polycyclic without condensed ring systems · CPC title