Resist removing liquid, resist removal method using same and method for producing photomask

Patent metadata

Field	Value
Publication number	US-9588428-B2
Application number	US-201514883730-A
Country	US
Kind code	B2
Filing date	Oct 15, 2015
Priority date	Apr 17, 2013
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

A resist removal method includes removing a resist provided on a photomask substrate by bringing a resist removing liquid into contact with the resist in patterning of a photomask for EUV lithography in which the resist removing liquid contains an alkali compound, a specific nitrogen-containing compound, and water, and a content of the water is more than 50% by mass.

First claim

What is claimed is:

1. A resist removal method comprising:
removing a resist provided on a photomask substrate by bringing a resist removing liquid into contact with the resist when a photomask for EUV lithography is produced,
wherein the resist removing liquid contains an alkali compound, a specific nitrogen-containing compound, and water,
the content of the water is more than 50% by mass, and
the specific nitrogen-containing compound is a compound represented by any of the following formulae (a-1) to (a-10):

wherein R a represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or a heterocyclic group; R b represents an alkyl group or an alkenyl group; L a represents an alkylene group, a carbonyl group, an imino group, an arylene group, a heterocyclic group, or a combination thereof; L b represents a single bond, an alkylene group, a carbonyl group, an imino group, an arylene group, a heterocyclic group, or a combination thereof; R c represents a hydrogen atom or an alkyl group; and n represents an integer of 0 or more.

2. The resist removal method according to claim 1 ,
wherein the alkali compound is a quaternary ammonium hydroxide.

3. The resist removal method according to claim 1 ,
wherein the molecular weight of the specific nitrogen-containing compound is 300 or more and 20,000 or less.

4. The resist removal method according to claim 1 ,
wherein the specific nitrogen-containing compound is a compound represented by the following formula (b),
R c 2 N—[L d —N(R c )] m -L d —NR c 2   (b)

in the formula, R c represents a hydrogen atom or an alkyl group; m represents an integer of 0 or more; and L d represents an alkylene group, a carbonyl group, an imino group, an arylene group, a heterocyclic group, or a combination thereof.

5. The resist removal method according to claim 1 ,
wherein removing the resist is performed at a treatment temperature of 15° C. or higher to less than 60° C.

6. The resist removal method according to claim 1 ,
wherein when the resist removing liquid is brought into contact with the resist on the photomask substrate to remove the resist, the resist removing liquid is brought into contact with the resist by being discharged, ejected, flowed down or dropped.

7. The resist removal method according to claim 1 ,
wherein the resist is a resin composition containing a polymer compound having a phenol structure.

8. A method for producing a photomask for EUV lithography comprising:
forming a photomask substrate by providing a reflecting layer, a protective layer, and an absorbing layer in this order on a base substrate;
providing a resist on an upper side of the absorbing layer of the photomask substrate;
patterning the resist by exposing and developing the photomask substrate with the resist to form a resist pattern;
etching a portion of the absorbing layer on which the resist is removed; and
removing the resist remaining after the etching by the resist removal method according to claim 1 .

9. A resist removing liquid that is used in patterning of a photomask for EUV lithography, the liquid comprising:
an alkali compound;
a specific nitrogen-containing compound; and
water,
wherein the content of the water is more than 50% by mass, and
the specific nitrogen-containing compound is a compound represented by any of the following formulae (a-1) to (a-10):

wherein R a represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or a heterocyclic group; R b represents an alkyl group or an alkenyl group; L a represents an alkylene group, a carbonyl group, an imino group, an arylene group, a heterocyclic group, or a combination thereof; L b represents a single bond, an alkylene group, a carbonyl group, an imino group, an arylene group, a heterocyclic group, or a combination thereof; R c represents a hydrogen atom or an alkyl group; and n represents an integer of 0 or more.

10. The resist removing liquid according to claim 9 ,
wherein the specific nitrogen-containing compound has a primary amine structure, a secondary amine structure, a tertiary amine structure, or a quaternary ammonium structure.

11. The resist removing liquid according to claim 9 ,
wherein the alkali compound is a quaternary ammonium hydroxide.

12. The resist removing liquid according to claim 9 ,
wherein the molecular weight of the specific nitrogen-containing compound is 300 or more and 20,000 or less.

13. The resist removing liquid according to claim 9 ,
wherein the specific nitrogen-containing compound is a compound represented by the following formula (b),
R c 2 N—[L d —N(R c )] m -L d —NR c 2   (b)

in the formula, R c represents a hydrogen atom or an alkyl group; m represents an integer of 0 or more; and L d represents an alkylene group, a carbonyl group, an imino group, an arylene group, a heterocyclic group, or a combination thereof.

14. The resist removing liquid according to claim 9 , comprising 0.5% by mass to 40% by mass of the alkali compound.

15. The resist removing liquid according to claim 9 , comprising 0.01% by mass to 20% by mass of the specific nitrogen-containing compound.

16. A resist removal method comprising:
removing a resist on an absorbing layer of a photomask substrate by bringing a resist removing liquid into contact with the resist when a photomask for EUV lithography is produced,
wherein the photomask substrate includes a reflecting layer, a protecting layer, and the absorbing layer in this order,
the resist removing liquid contains an alkali compound, a specific nitrogen-containing compound, and water, and
the content of the water is more than 50% by mass.

17. The resist removal method according to claim 16 ,
wherein the specific nitrogen-containing compound has a primary amine structure, a secondary amine structure, a tertiary amine structure, or a quaternary ammonium structure.

18. The resist removal method according to claim 16 ,
wherein the alkali compound is a quaternary ammonium hydroxide.

19. The resist removal method according to claim 16 ,
wherein the molecular weight of the specific nitrogen-containing compound is 300 or more and 20,000 or less.

20. The resist removal method according to claim 16 ,
wherein the specific nitrogen-containing compound is a compound represented by any of the following formulae (a-1) to (a-10):

wherein R a represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or a heterocyclic group; R b represents an alkyl group or an alkenyl group; L a represents an alkylene group, a carbonyl group, an imino group, an arylene group, a heterocyclic group, or a combination thereof; L b represents a single bond, an alkylene group, a carbonyl group, an imino group, an arylene group, a heterocyclic group, or a combination thereof; R c represents a hydrogen atom or an alkyl group; and n represents an integer of 0 or more.

21. The r

Assignees

• Fujifilm Corp

Inventors

• Mizutani Atsushi

Classifications

• B08B3/08

  the liquid having chemical or dissolving effect · CPC title

• G03F1/22

  Masks or mask blanks for imaging by radiation of 100nm or shorter wavelength, e.g. X-ray masks, extreme ultraviolet [EUV] masks; Preparation thereof · CPC title

• C11D7/3281

  Heterocyclic compounds · CPC title

• G03F7/425 Primary

  containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen · CPC title

• G03F7/322 Primary

  Aqueous alkaline compositions · CPC title