IP Library Granted Patent US 8,652,749
Granted Patent B2
US 8,652,749 · App. 13/037,212 · Granted Feb 18, 2014

Photoresist composition and method of forming pattern by using the same

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,652,749
App. No.
13/037,212
Granted
Feb 18, 2014
Kind
B2
Abstract

A photoresist composition is provided. The photoresist composition includes an alkali-soluble resin; a photosensitizer containing a first compound that contains a diazonaphthoquinone represented by Formula 1 and a second compound that contains a diazonaphthoquinone represented by Formula 2; and a solvent. and R1 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 4 carbons, an alkenyl group having 2 to 4 carbons, a cycloalkyl group having 3 to 8 carbons, and an aryl group having 6 to 12 carbons, and R2 is selected from the group consisting of Cl, F, Br, and I.

Claims (29)

1. A photoresist composition, comprising:

an alkali-soluble resin;

a photosensitizer comprising a first compound comprising a diazonaphthoquinone represented by Formula 1 and a second compound comprising a diazonaphthoquinone represented by Formula 2; and

a solvent,

wherein the ratio of the first compound to the second compound ranges from about 1:3 to about 1:7, based on parts per weight of the photoresist composition, and

wherein R1 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 4 carbons, an alkenyl group having 2 to 4 carbons, a cycloalkyl group having 3 to 8 carbons, and an aryl group having 6 to 12 carbons, and wherein R2 is a bond to a corresponding oxygen.

2. The photoresist composition of claim 1 , wherein the photosensitizer ranges from about 1 part by weight to about 25 parts by weight of the photoresist composition.

3. The photoresist composition of claim 1 , wherein the second compound ranges from about 10 parts by weight to about 20 parts by weight of the photoresist composition.

4. The photoresist composition of claim 1 , wherein the photosensitizer absorbs H-line light comprising a wavelength of about 405 nm.

5. The photoresist composition of claim 1 , further comprising at least one additive selected from the group consisting of a surfactant, an adhesion promoter, a plasticizer, a sensitizer, and a resin.

6. The photoresist composition of claim 1 , wherein the photoresist composition is a positive photoresist composition.

7. The photoresist composition of claim 1 , wherein the alkali-soluble resin ranges from about 2 parts by weight to about 50 parts by weight of the photoresist composition.

8. The photoresist composition of claim 1 , wherein the alkali-soluble resin comprises a weight-average molecular weight ranging from about 2,000 to about 50,000.

9. The photoresist composition of claim 1 , wherein the alkali-soluble resin comprises a novolac resin comprising meta-cresol and para-cresol.

10. A method of forming a pattern, the method comprising:

forming a photoresist film by arranging a photoresist composition on a pattern forming film, the photoresist composition comprising an alkali-soluble resin, a photosensitizer comprising a first compound comprising a diazonaphthoquinone represented by Formula 1 and a second compound comprising a diazonaphthoquinone represented by Formula 2, and a solvent;

exposing the photoresist film to light;

forming a photoresist pattern by developing the photoresist film; and

patterning the pattern forming film using the photoresist pattern as an etch mask,

the ratio of the first compound to the second compound ranges from about 1:3 to about 1:7, based on parts per weight of the photoresist composition, and

R1 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 4 carbons, an alkenyl group having 2 to 4 carbons, a cycloalkyl group having 3 to 8 carbons, and an aryl group having 6 to 12 carbons, and R2 is selected from the group consisting of Cl, F, Br, and I.

11. The method of claim 10 , wherein the photosensitizer ranges from about 1 part by weight to about 25 parts by weight of the photoresist composition.

12. The method of claim 10 , wherein the second compound ranges from about 10 parts by weight to about 20 parts by weight of the photoresist composition.

13. The method of claim 10 , further comprising performing a condensation reaction of 2,3,4,4′-tetrahydroxybenzophenone with a naphthoquinone 1,2-diazide-5-sulfonyl chloride compound to obtain the first compound.

14. The method of claim 10 , further comprising performing a condensation reaction of 4,4′,4″-ethylidynetrisphenol with a naphthoquinone 1,2-diazide-5-sulfonyl chloride compound to obtain the second compound.

15. The method of claim 10 , wherein in the exposing the photoresist film to light, the light comprises an H-line light comprising a wavelength of about 405 nm.

16. The method of claim 10 , wherein the photoresist composition comprises a positive photoresist composition.

17. The method of claim 10 , wherein the alkali-soluble resin comprises a novolac resin comprising meta-cresol and para-cresol.

18. The method of claim 10 , wherein the alkali-soluble resin ranges from about 2 parts by weight to about 50 parts by weight of the photoresist composition.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 17, 2022
From: MERCK PATENT GMBH
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 060102/0506 →
CHANGE OF NAME Recorded Sep 26, 2016
From: AZ ELECTRONIC MATERIALS KOREA LTD.
To: MERCK ELECTRONIC MATERIALS LTD.
Reel/Frame 040150/0624 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 26, 2016
From: MERCK ELECTRONIC MATERIALS LTD.
To: MERCK PATENT GMBH
Reel/Frame 039860/0957 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 12, 2012
From: AZ ELECTRONIC MATERIALS K.K.
To: AZ ELECTRONIC MATERIALS (KOREA) LTD.
Reel/Frame 029120/0201 →
CHANGE OF NAME Recorded Aug 28, 2012
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 028860/0076 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 23, 2011
From: LEE, HI-KUK; YUN, SANG-HYUN; KIM, CHA-DONG; PARK, JUNG-IN; KANG, DEOK-MAN; KIM, YOUN-SUK; OH, SAE-TAE
To: SAMSUNG ELECTRONICS CO., LTD.; AZ ELECTRONIC MATERIALS K.K.
Reel/Frame 026323/0698 →