Materials and methods for improved photoresist performance

Patent metadata

Field	Value
Publication number	US-9851636-B2
Application number	US-201213542160-A
Country	US
Kind code	B2
Filing date	Jul 5, 2012
Priority date	Jul 5, 2012
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

A photosensitive material and methods of making a pattern on a substrate are disclosed. The photosensitive material includes a polymer that turns soluble to a developer solution after a chemically amplified reaction, and at least one chemical complex having a single diffusion length. The material includes at least one photo-acid generator (PAG) linked to at least one photo decomposable base (PDB) or quencher.

First claim

What is claimed is:

1. A photosensitive material, comprising:
a polymer that turns soluble to a developer solution after a chemically amplified reaction; and
at least one chemical complex comprising at least one photo-acid generator (PAG), at least one photo decomposable base (PDB) or quencher, and a linking compound that links the PAG to the PDB or quencher through covalent bonding, the linking compound being a polyethylene glycol,
wherein the chemical complex has a single diffusion length.

2. The photosensitive material of claim 1 , wherein the PDB comprises a nitrogen-containing compound.

3. The photosensitive material of claim 2 , wherein the PDB is represented by Formula (a), (b), (c), (d), or (e):

wherein R 1 -R 7 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aminoalkyl group having 1 to 20 carbon atoms, a hydroxyalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 1 to 20 carbon atoms, and R 1 -R 7 are capable of binding together to form a ring.

4. The photosensitive material of claim 2 , wherein the nitrogen-containing compound comprises two or more nitrogen atoms.

5. The photosensitive material of claim 4 , wherein the nitrogen containing compound is selected from the group consisting of a substituted or unsubstituted guanidine, a substituted or unsubstituted aminopyridine, a substituted or unsubstituted aminoalkylpyridine, a substituted or unsubstituted aminopyrrolidine, a substituted or unsubstituted indazole, an imidazole, a substituted or unsubstituted pyrazole, a substituted or unsubstituted pyrazine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted purine, a substituted or unsubstituted imidazoline, a substituted or unsubstituted pyrazoline, a substituted or unsubstituted piperazine, a substituted or unsubstituted aminomorpholine, and a substituted or unsubstituted aminoalkylmorpholine.

6. The photosensitive material of claim 5 , wherein substituents on the nitrogen containing compound are selected from the group consisting of an amino group, an aminoalkyl group, an alkylamino group, an aminoaryl group, an arylamino group, an alkyl group, an alkoxy group, an acyl group, an acyloxy group, an aryl group, an aryloxy group, a nitro group, a hydroxyl group, and a cyano group.

7. The photosensitive material of claim 1 , wherein the PAG is selected from the group consisting of onium salts, selenium salts, phosphonium salts, iodinium, sulfonium salts, organic halogen compounds, O-nitrobenzylsulfonate compounds, N-iminosulfonate compounds, N-imidosulfonate compounds, diazosulfonate compound, sulfonimide compounds, diazodisulfonate compounds, and disulfone compounds.

8. The photosensitive material of claim 1 , wherein the PAG is represented by one of the following structures:

wherein R 1 -R 33 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aminoalkyl group having 1 to 20 carbon atoms, a hydroxyalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 1 to 20 carbon atoms, and R 1 -R 33 is capable of binding together to form a ring;
X − represents a counter ion comprising BF −4 , AsF 6 , PF −6 , SBF 6 , SiF −6 , ClO −4 , perfluoroalkanesulfonic acid anion, alkylsulfoni anion, armomatic sulfonic acid anion, benzesulfonic acid anion or triisopropylbenzenesulfonic anion, a condensed polycyclic aromatic sulfonic acid anion, or a dye containing sulfonic acid;
Ar 1 and Ar 2 are the same or different, each representing an unsubstituted or substituted aryl group;
A represents an unsubstituted or substituted alkylene group, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group; and
Y represents a chlorine or bromine atom.

9. A photosensitive material, comprising:
a polymer that turns soluble to a developer solution after a chemically amplified reaction;
at least one photo-acid generator (PAG); and
at least one photo decomposable base (PDB) or quencher, wherein the PAG and the PDB or quencher have substantially similar diffusion lengths, wherein the at least one PAG is linked to the at least one PDB or quencher by a linking agent, wherein the linking agent is a polyethylene glycol or a polycyclic aromatic hydrocarbon.

10. The photosensitive material of claim 9 , wherein the PDB comprises a nitrogen-containing compound.

11. The photosensitive material of claim 10 , wherein the nitrogen containing compound is selected from the group consisting of a substituted or unsubstituted guanidine, a substituted or unsubstituted aminopyridine, a substituted or unsubstituted aminoalkylpyridine, a substituted or unsubstituted aminopyrrolidine, a substituted or unsubstituted indazole, an imidazole, a substituted or unsubstituted pyrazole, a substituted or unsubstituted pyrazine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted purine, a substituted or unsubstituted imidazoline, a substituted or unsubstituted pyrazoline, a substituted or unsubstituted piperazine, a substituted or unsubstituted aminomorpholine, and a substituted or unsubstituted aminoalkylmorpholine.

12. The photosensitive material of claim 9 , wherein the PAG is selected from the group consisting of onium salts, selenium salts, phosphonium salts, iodinium, sulfonium salts, organic halogen compounds, O-nitrobenzylsulfonate compounds, N-iminosulfonate compounds, N-imidosulfonate compounds, diazosulfonate compound, sulfonimide compounds, diazodisulfonate compounds, and disulfone compounds.

13. A photosensitive material comprising:
a polymer that turns soluble to a developer solution after a chemically amplified reaction;
a photo-acid generator; and
a material selected from the group consisting of a photo decomposable base and a quencher, wherein the photo-acid generator is linked to the material by a polycyclic aromatic hydrocarbon.

14. The photosensitive material of claim 13 , wherein the material selected is the photo decomposable base.

15. The photosensitive material of claim 13 , wherein the material selected is the quencher.

16. The photosensitive material of claim 13 , wherein the photo-acid generator linked to the material has a single diffusion length.

17. The photosensitive material of claim 9 , wherein the linking agent is the polyethylene glycol.

18. The photosensitive material of claim 17 , wherein the polyethylene glycol has the following structure:

19. The photosensitive material of claim 9 , wherein the linking agent is the polycyclic aromatic hydrocarbon.

20. The photosensitive material of claim 19 , wherein the polycyclic aromatic hydrocarbon has the following structure:

Assignees

• Liu Chen-Yu
• Chang Ching-Yu
• Taiwan Semiconductor Mfg Co Ltd

Inventors

• Liu Chen-Yu
• Chang Ching-Yu

Classifications

• G03F7/0382

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

• G03F7/0163

  Non ionic diazonium compounds, e.g. diazosulphonates; Precursors thereof, e.g. triazenes · CPC title

• G03F7/0392

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

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title