Photoresist composition and method of forming photoresist pattern

Patent metadata

Field	Value
Publication number	US-11971659-B2
Application number	US-201916584234-A
Country	US
Kind code	B2
Filing date	Sep 26, 2019
Priority date	Oct 8, 2018
Publication date	Apr 30, 2024
Grant date	Apr 30, 2024

Abstract

A photoresist composition includes a conjugated resist additive, a photoactive compound, and a polymer resin. The conjugated resist additive is one or more selected from the group consisting of a polyacetylene, a polythiophene, a polyphenylenevinylene, a polyfluorene, a polypryrrole, a polyphenylene, and a polyaniline. The polyacetylene, polythiophene, polyphenylenevinylene, polyfluorene, polypryrrole, the polyphenylene, and polyaniline includes a substituent selected from the group consisting of an alkyl group, an ether group, an ester group, an alkene group, an aromatic group, an anthracene group, an alcohol group, an amine group, a carboxylic acid group, and an amide group. Another photoresist composition includes a polymer resin having a conjugated moiety and a photoactive compound. The conjugated moiety is one or more selected from the group consisting of a polyacetylene, a polythiophene, a polyphenylenevinylene, a polyfluorene, a polypryrrole, a polyphenylene, and a polyaniline.

First claim

What is claimed is:

1. A method of forming a pattern in a photoresist, comprising:
forming a photoresist composition layer over a substrate;
selectively exposing the photoresist layer to actinic radiation to form a latent pattern; and
developing the latent pattern by applying a developer to the selectively exposed photoresist layer to form a pattern,
wherein the photoresist composition comprises:
a conjugated resist additive;
a photoactive compound; and
a polymer resin,
wherein the conjugated resist additive is one or more selected from the group consisting of a polyacetylene, a polythiophene, a polyphenylenevinylene, a polyfluorene, a polypryrrole, a polyphenylene, and a polyaniline,
wherein the polythiophene, polyphenylenevinylene, polyfluorene, polypryrrole, polyphenylene, and polyaniline are substituted with one or more substituents selected from the group consisting of an alkyl group, an ether group, an ester group, an alkene group, an aromatic group, an anthracene group,

an alcohol group, an amine group, a carboxylic acid group, and an amide group, and

wherein the conjugated resist additive includes a conjugated moiety attached to either a photobase generator or triphenylsulfonium hydroxide.

2. The method according to claim 1 , wherein the actinic radiation is extreme ultraviolet radiation.

3. The method according to claim 1 , further comprising after selectively exposing the photoresist layer to actinic radiation to form a latent pattern and before developing the latent pattern heating the photoresist layer.

4. The method according to claim 1 , wherein the conjugated resist additive has a band gap of 0.3 eV to 4 eV.

5. The method according to claim 1 , wherein the conjugated resist additive has a weight average molecular weight of 50 to 1,000,000.

6. The method according to claim 1 , wherein the photoresist composition further comprises metal oxide nanoparticles and one or more organic ligands.

7. The method according to claim 1 , wherein the photoresist composition further comprises one or more solvents.

8. The method according to claim 1 , wherein:
the polymer resin comprises

and the conjugated resist additive is

where PBG is the photobase generator and R is the substituent.

9. The method according to claim 1 , wherein the one or more substituents include an acid leaving group.

10. A method of forming a pattern in a photoresist, comprising:
forming a photoresist composition layer over a substrate;
selectively exposing the photoresist layer to actinic radiation to form a latent pattern; and
developing the latent pattern by applying a developer to the selectively exposed photoresist layer to form a pattern,
wherein the photoresist composition comprises:
a polymer resin having a conjugated moiety; and
a photoactive compound;
wherein the conjugated moiety is a polyfluorene.

11. The method according to claim 10 , wherein the actinic radiation is extreme ultraviolet radiation.

12. The method according to claim 10 , wherein the polyfluorene is substituted with one or more substituents selected from the group consisting of an alkyl group, an ether group, an ester group, an alkene group, an aromatic group, an anthracene group, an alcohol group, an amine group, a carboxylic acid group, and an amide group.

13. The method according to claim 12 , wherein the one or more substituents include an acid leaving group attached to either an alcohol group substituent or a carboxylic acid group substituent.

14. The method according to claim 10 , wherein the photoresist composition further comprises metal oxide nanoparticles and one or more organic ligands.

15. The method according to claim 10 , wherein:
the polymer resin comprises

16. A method of forming a pattern in a photoresist, comprising:
forming a photoresist composition layer over a substrate;
selectively exposing the photoresist layer to actinic radiation to form a latent pattern; and
developing the latent pattern by applying a developer to the selectively exposed photoresist layer to form a pattern,
wherein the photoresist composition comprises:
a polymer resin having a first conjugated moiety; and
a photoacid generator attached to a second conjugated moiety,
wherein the first conjugated moiety is one or more selected from the group consisting of a polyacetylene, a polyphenylenevinylene, a polyfluorene, and a polyphenylene, and
the second conjugated moiety is one or more selected from the group consisting of a polyacetylene, a polythiophene, a polyphenylenevinylene, a polyfluorene, a polypryrrole, and a polyaniline.

17. The method according to claim 16 , wherein the actinic radiation is extreme ultraviolet radiation.

18. The method according to claim 16 , further comprising after selectively exposing the photoresist layer to actinic radiation to form a latent pattern and before developing the latent pattern heating the photoresist layer.

19. The method according to claim 16 , wherein the polyphenylenevinylene, polyfluorene, and polyphenylene of the first conjugated moiety are substituted with one or more substituents selected from the group consisting of an alkyl group, an ether group, an ester group, an alkene group, an aromatic group, an anthracene group, an alcohol group, an amine group, a carboxylic acid group, and an amide group, and
the polythiophene, polyphenylenevinylene, polyfluorene, polypryrrole, and polyaniline of the second conjugated moiety are substituted with one or more substituents selected from the group consisting of an alkyl group, an ether group, an ester group, an alkene group, an aromatic group, an anthracene group, an alcohol group, an amine group, a carboxylic acid group, and an amide group.

20. The method according to claim 19 , wherein one or more substituents on the first conjugated moiety include an acid leaving group attached to either an alcohol group substituent or a carboxylic acid group substituent.

Assignees

• Taiwan Semiconductor Mfg Co Ltd

Inventors

• Ho Chun-Chih
• Chang Ching-Yu
• Lin Chin-Hsiang

Classifications

• G03F7/0387 Primary

  Polyamides or polyimides · CPC title

• G03F7/0125

  characterised by the polymeric binder or the macromolecular additives other than the macromolecular azides · CPC title

• G03F7/0382

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

• G03F7/0388

  with ethylenic or acetylenic bands in the side chains of the photopolymer · CPC title

• G03F7/168

  Finishing the coated layer, e.g. drying, baking, soaking · CPC title