IP Library Granted Patent US 9,851,635
Granted Patent B2
US 9,851,635 · App. 14/801,111 · Granted Dec 26, 2017

Photoresist composition and method of manufacturing substrate for display device by using the same

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Quick Facts
Patent No.
US 9,851,635
App. No.
14/801,111
Granted
Dec 26, 2017
Kind
B2
Abstract

A photoresist composition includes an alkali soluble resin, a hardening agent, a photo acid generator, and an organic solvent. The photo acid generator may be represented by Formula 1, in which L 11 is selected from a single bond, a C 1 -C 10 alkylene group, a C 2 -C 10 alkenylene group, and a C 2 -C 10 alkynylene group; and R 11 is selected from a C 6 -C 15 aryl group, or a C 6 -C 15 aryl group with at least one substitutent group selected from a group comprising deuterium, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 15 aryl group.

Claims (56)

1. A photoresist composition, comprising

an acryl copolymer in an amount of 25 wt. %;

novolac-based resin in an amount of 25 wt. % comprising a mixture of 75 wt. % of meta-cresol and 25 wt. % of para-cresol;

a melamine-based resin in an amount of about 3 wt. % to about 7 wt. %;

a photo acid generator represented by a Formula 1 in an amount of about 1 to about 7 wt. %; and

a balance being propylene glyeolmonomethyletheracetate,

wherein in Formula 1,

L 11 is selected from a single bond a C 1 -C 10 alkylene group, a C 2 -C 10 alkenylene group, and a C 2 -C 10 alkynylene group; and

R 11 is selected from a C 6 -C 15 aryl group, or a C 6 -C 15 aryl group with at least one substitutent group selected from a group comprising deuterium, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 15 aryl group.

2. The photoresist composition of claim 1 , wherein

the novolac-based resin has a weight average molecular weight of about 7,000 to about 30,000, based on polystyrene.

3. The photoresist composition of claim 1 , wherein

L 11 is selected from a single bond and a C 2 -C 10 alkenylene group.

4. The photoresist composition of claim 1 , wherein

L 11 is selected from a single bond and an ethenylene group.

5. The photoresist composition of claim 1 , wherein

R 11 is a phenyl group; or

a phenyl group with at least one substitutent group selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, a methoxy group, an ethoxy group and a phenyl group.

6. The photoresist composition of claim 1 , wherein

R 11 is a phenyl group with a methoxy group.

7. The photoresist composition of claim 1 , wherein

R 11 is selected from Formulae 2-1 or 2-2:

in Formulae 2-1 and 2-2,

wherein * indicates a binding site to a neighboring atom.

8. The photoresist composition of claim 1 , wherein

the photo acid generator comprises at least one selected from Compounds 1 or 2:

9. A method of manufacturing a substrate for a display device, the method comprising:

forming a photoresist layer on a substrate using a photoresist composition that includes a) an alkali soluble resin, b) a hardening agent, e) a photo acid generator represented by Formula 1, and d) an organic solvent; and

exposing and developing the photoresist layer to form an organic insulating film having a first hole,

wherein in Formula 1,

L 11 is selected from a single bond, a C 1 -C 10 alkylene group, a C 2 -C 10 alkenylene group, and a C 2 -C 10 alkynylene group; and

R 11 is selected from a C 6 -C 15 aryl group; or

a C 6 -C 15 aryl group with at least one substitutent group selected from a group comprising deuterium, a hydroxyl group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, and a C 6 -C 15 aryl group.

10. The method of claim 9 , wherein exposing and developing the photoresist layer comprises

applying the photoresist composition on the substrate to form a coating film

irradiating light having a wavelength of about 400 nm to about 410 nm to the coating film; and

developing the coating film with a developer solution.

11. The method of claim 10 , wherein irradiating light comprises

irradiating a plurality of spot beams to the coating film using a digital exposure device,

wherein the spot beams are selectively irradiated to exposed areas and are shielded from a contact hole formation area by turning on or off micro-mirrors of the digital exposure device, and a portion of the coating film on the contact hole formation area is removed using the developer solution.

12. The method of claim 9 , further comprising

prior to the forming of the photoresist layer, forming a thin film transistor comprising a gate electrode, a source electrode, and a drain electrode, and a passivation layer on the substrate, wherein the photoresist layer is formed on the passivation layer.

13. The method of claim 12 , further comprising

after exposing and developing the photoresist layer, etching the passivation layer using the organic insulating film having the first hole as an etch prevention film to form a second hole corresponding to the first hole, wherein the first and second holes define a contact hole that exposes a portion of the drain electrode;

forming a transparent electrode layer on the organic insulating film with the first and second contact holes, and

patterning the transparent electrode layer to form a pixel electrode, wherein the pixel electrode contacts the portion of the drain electrode through the first and second contact holes.

14. A photoresist composition comprising:

an acryi copolymer in an amount of 25 wt. %;

a novolac based resin in an amount of 25 wt. %;

a melamine-based resin in an amount of about 3 wt. % to about 7 wt. %;

a photo acid generator comprising at least one selected from Compounds 1 and 2 in an amount of about 1 to about 7 wt. %; and

a balance being propylene glyeolmonomethyletheracetate,

15. The photoresist composition of claim 14 , wherein

the novolac-based resin comprises a mixture of 75 wt. % of meta-cresol and 25 wt. % of para-cresol.

16. The photoresist composition of claim 14 , wherein

the novolac-based resin has a weight average molecular weight of about 7,000 to about 30,000, based on polystyrene.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2020
From: MERCK ELECTRONICS MATERIALS LTD.,
To: MERCK PATENT GMBH
Reel/Frame 053740/0150 →
CHANGE OF LEGAL ENTITY Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS S.À R.L.
To: AZ ELECTRONIC MATERIALS GMBH
Reel/Frame 053323/0760 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS GMBH
To: MERCK PATENT GMBH
Reel/Frame 053323/0770 →
MERGER Recorded Jul 27, 2020
From: RIDGEFIELD ACQUISITION
To: AZ ELECTRONIC MATERIALS S.À R.L.
Reel/Frame 053323/0591 →
MERGER Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
To: RIDGEFIELD ACQUISITION
Reel/Frame 053324/0198 →
CHANGE OF ADDRESS Recorded Jan 12, 2017
From: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
To: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
Reel/Frame 041345/0585 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 16, 2015
From: KIM, CHADONG; KANG, HOON; SUNG, WOOYONG; LEE, HIKUK; KIM, CHANGHOON; PARK, JUNGIN; YUN, SANGHYUN; LEE, KIBEOM; CHANG, JAEHYUK; KANG, DEOKMAN; KIM, YOUNSUK; OH, SAETAE
To: SAMSUNG DISPLAY CO., LTD.; AZ ELECTRONIC MATERIALS (LUXEMBOURG) SARL
Reel/Frame 036115/0546 →