Photoresist composition and method of forming photoresist pattern

Patent metadata

Field	Value
Publication number	US-12222647-B2
Application number	US-202217873130-A
Country	US
Kind code	B2
Filing date	Jul 25, 2022
Priority date	Oct 8, 2018
Publication date	Feb 11, 2025
Grant date	Feb 11, 2025

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 photoresist composition, comprising:
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 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 conjugated resist additive includes a conjugated moiety attached to either a photobase generator or triphenylsulfonium hydroxide.

2. The photoresist composition of claim 1 , wherein the conjugated resist additive has a band gap of 0.3 eV to 4 eV.

3. The photoresist composition of claim 1 , wherein the conjugated resist additive has a weight average molecular weight of 50 to 1,000,000.

4. The photoresist composition of claim 1 , further comprising metal oxide nanoparticles and one or more organic ligands.

5. The photoresist composition of claim 1 , further comprising one or more solvents.

6. The photoresist composition of claim 1 , wherein:
the polymer resin comprises

and the conjugated resist additive is PBG is a photobase generator and R is the substituent.

7. The photoresist composition of claim 1 , wherein the one or more substituents include an acid labile group.

8. A photoresist composition, comprising:
a polymer resin having a conjugated moiety; and
a photoactive compound,
wherein the conjugated moiety is a polyfluorene.

9. The photoresist composition of claim 8 , 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.

10. The photoresist composition of claim 9 , wherein the one or more substituents include an acid labile group.

11. The photoresist composition of claim 8 , wherein the polymer resin having a conjugated moiety has a weight average molecular weight of 50 to 1,000,000.

12. The photoresist composition of claim 8 , further comprising metal oxide nanoparticles and one or more organic ligands.

13. The photoresist composition of claim 8 , further comprising one or more solvents.

14. The photoresist composition of claim 8 , wherein the conjugated moiety is a repeating unit of a pendant group on a main chain of the polymer resin.

15. A photoresist composition, comprising:
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.

16. The photoresist composition of claim 15 , 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.

17. The photoresist composition of claim 16 , wherein one or more substituents on the first conjugated moiety include an acid labile group attached to either an alcohol group substituent or a carboxylic acid group substituent.

18. The photoresist composition of claim 15 , wherein 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.

19. The photoresist composition of claim 15 , further comprising metal oxide nanoparticles and one or more organic ligands.

20. The photoresist composition of claim 15 , wherein:
the polymer resin comprises

Assignees

• Taiwan Semiconductor Mfg Co Ltd

Inventors

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

Classifications

• G03F7/168

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

• G03F7/0388

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

• G03F7/0382

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

• G03F7/0125

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

• G03F7/2012

  using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps · CPC title