Photoacid generator and chemically amplified positive-type photoresist composition for thick film comprising the same

Patent metadata

Field	Value
Publication number	US-11150555-B2
Application number	US-201816337280-A
Country	US
Kind code	B2
Filing date	Apr 3, 2018
Priority date	Sep 11, 2017
Publication date	Oct 19, 2021
Grant date	Oct 19, 2021

Abstract

A non-ionic photoacid generator and a chemically amplified positive-type photoresist composition for a thick film including the non-ionic photoacid generator. The non-ionic photoacid generator may not only exhibit high solubility in a solvent of the photoresist composition, but may also exhibit chemical and thermal stability and high sensitivity. In particular, the non-ionic photoacid generator is decomposed by light to generate an acid, and at the same time, can exhibit a corrosion preventing effect on a metal substrate.

First claim

The invention claimed is:

1. A non-ionic photoacid generator comprising at least one functional group represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,
R 1 is a C1 to C10 aliphatic hydrocarbon group substituted or unsubstituted with at least one of a halogen atom, an alkylthio group, and an alicyclic hydrocarbon group; a C1 to C10 perfluoroalkyl group; a C6 to C20 aryl group substituted or unsubstituted with at least one of a halogen atom, an alkylthio group, an alkyl group, and an acyl group; or a C7 to C20 arylalkyl group substituted or unsubstituted with a halogen atom and an alkylthio group, and
Z is a group represented by the following Chemical Formula 2b:

wherein, in Chemical Formula 2b,
R 2 is hydrogen, a C3 to C10 alkyl group, or a C1 to C10 hydroxyalkyl group,
R 3 is a chemical bond, a C1 to C10 alkylene group, or a group represented by the following Chemical Formula 3, and
when R 2 is a C3 to C10 alkyl group and R 3 is a C1 to C10 alkylene group, they are connected to each other to form a C4 to C20 aliphatic ring,

wherein, in Chemical Formula 3,
R a is a chemical bond or a C1 to C10 alkylene group,
R b is a C1 to C10 alkylene group,
n is an integer of 1 to 10, and
when n is 2 or more, each R b , which is repeated two or more times, is the same or different from each other.

2. The non-ionic photoacid generator of claim 1 ,
wherein the non-ionic photoacid generator is represented by the following Chemical Formula 5a or 5b:

wherein, in Chemical Formulae 5a and 5b,
R 1 , R 2 , and R 3 are as defined above in Chemical Formulae 1, 2b, and 3.

3. A chemically amplified positive-type photoresist composition for a thick film comprising the non-ionic photoacid generator of claim 2 .

4. A chemically amplified positive-type photoresist composition for a thick film comprising the non-ionic photoacid generator of claim 1 .

5. The chemically amplified positive-type photoresist composition for a thick film of claim 4 , wherein the composition does not comprise a separate corrosion inhibitor.

6. The chemically amplified positive-type photoresist composition for a thick film of claim 4 , wherein the composition further comprises an alkali developable polymer resin, a photoinitiator and an organic solvent.

7. The non-ionic photoacid generator of claim 1 , comprising one, two, three or four functional groups represented by Chemical Formula 1 as defined in claim 1 .

8. The non-ionic photoacid generator of claim 1 , wherein R 1 is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, 2-hexyl, 3-hexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, tridecylfluorohexyl, heptafluorooctyl, 2,2,2-trifluoroethyl, 1,1-difluoroethyl, 1,1-difluoropropyl, 1,1,2,2-tetrafluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,2-tetrafluorotetradecyl, phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4-(2-ethylhexyl)phenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-di-tert-butylphenyl, 2,5-di-tert-butylphenyl, 2,6-di-tert-butylphenyl, 2,4-di-tert-pentylphenyl, 2,5-di-tert-amylphenyl, 2,5-di-tert-octylphenyl, cyclohexylphenyl, biphenyl, 2,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2,4,6-triisopropylphenyl, pentafluorophenyl, chlorophenyl, dichlorophenyl, trichlorophenyl, 2,4-bis(trifluoromethyl)phenyl, bromoethylphenyl, 4-methylthiophenyl, 4-butylthiophenyl, 4-octylthiophenyl, 4-dodecylthiophenyl, 1,2,5,6-tetrafluoro-4-methylthiophenyl, 1,2,5,6-tetrafluoro-4-butylthiophenyl, 1,2,5,6-tetrafluoro-4-dodecylthiophenyl, benzyl, phenethyl, 2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl, pentafluorophenylmethyl, phenyldifluoromethyl, 2-phenyl-tetrafluoroethyl, 2-(pentafluorophenyl)ethyl, p-methylthiobenzyl, 2,3,5,6-tetrafluoro-4-methylthiophenylethyl, acetylphenyl, acetylnaphthyl, benzoylphenyl, 1-anthraquinolyl, or 2-anthraquinolyl group.

9. A non-ionic photoacid generator comprising at least one functional group represented by the following Chemical Formula 4a or 4b:

wherein, in Chemical Formulae 4a and 4b,
R 1 is a C1 to C10 aliphatic hydrocarbon group substituted or unsubstituted with at least one of a halogen atom, an alkylthio group, and an alicyclic hydrocarbon group; a C1 to C10 perfluoroalkyl group; a C6 to C20 aryl group substituted or unsubstituted with at least one of a halogen atom, an alkylthio group, an alkyl group, and an acyl group; or a C7 to C20 arylalkyl group substituted or unsubstituted with a halogen atom and an alkylthio group,
R 2 is hydrogen, a C3 to C10 alkyl group, or a C1 to C10 hydroxyalkyl group,
R 3 is a chemical bond, a C1 to C10 alkylene group, or a group represented by the following Chemical Formula 3, and
when R 2 is a C3 to C10 alkyl group and R 3 is a C1 to C10 alkylene group, they are connected to each other to form a C4 to C20 aliphatic ring,

wherein, in Chemical Formula 3,
R a is a chemical bond or a C1 to C10 alkylene group,
R b is a Cl to C10 alkylene group,
n is an integer of 1 to 10, and
when n is 2 or more, each R b , which is repeated two or more times, is the same or different from each other,
T is —H, —(C═O)OH, —O—(C═O)OH, —(C═O)NH 2 , —NH—(C═O)H, —OCH 3 , —SH, —NH 2 , —NO 2 , —CF 3 , or —SF 3 , and
R c is a C4 to C20 aliphatic ring.

10. A chemically amplified positive-type photoresist composition for a thick film comprising the non-ionic photoacid generator of claim 9 .

11. The chemically amplified positive-type photoresist composition for a thick film of claim 10 , wherein the composition does not comprise a separate corrosion inhibitor.

12. The chemically amplified positive-type photoresist composition for a thick film of claim 10 , wherein the composition further comprises an alkali developable polymer resin, a photoinitiator and an organic solvent.

13. The non-ionic photoacid generator of claim 9 , comprising one, two, three or four functional groups represented by Chemical Formulae 4a or 4b as defined in claim 9 .

14. The non-ionic photoacid generator of claim 9 , wherein R 1 is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, 2-hexyl, 3-hexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tert-heptyl, octyl, isooctyl, tert-octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl,

Assignees

• Lg Chemical Ltd

Inventors

• Lim Min Young
• Lee Tae Seob
• Kim Ji Hye

Classifications

• C07D221/14 Primary

  Aza-phenalenes, e.g. 1,8-naphthalimide · CPC title

• G03F7/0045 Primary

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

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title