Photoresist resin composition, method of forming a photoresist pattern, and method of manufacturing a display substrate using the same

1. A photoresist resin composition comprising:

(A) about 10 to about 35% by weight of an acryl-based copolymer comprising as monomers about 5 to about 40% by weight of an unsaturated carboxylic acid, about 10 to about 70% by weight of an unsaturated compound containing an epoxy group, and about 10 to about 70% by weight of an unsaturated olefin-based compound, based on the total weight of the monomers,

(B) about 5 to about 10% by weight of a quinone diazide compound,

(C) about 55 to about 80% by weight of a solvent; and

(D) about 0.01 to about 0.5% by weight of a silane-based surfactant represented by Chemical Formula (1):

wherein R 1 represents an ethylene oxide group, R 2 represents a propylene oxide group, and X and Y represent integers of about 1 to about 20, and wherein the weights of each of the acryl-based copolymer, quinone diazide compound, solvent, and silane-based surfactant are based on the total weight of acryl-based copolymer, quinone diazide compound, solvent, and silane-based surfactant.

2. The photoresist resin composition of claim 1 , wherein the unsaturated carboxylic acid comprises acrylic acid, methacrylic acid, maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, or a mixture comprising at least one of the foregoing unsaturated carboxylic acids.

3. The photoresist resin composition of claim 1 , wherein the unsaturated compound containing an epoxy group comprises glycidyl acrylate, glycidyl methacrylate, α-ethylglycidyl acrylate, α-n-propylglycidyl acrylate, α-n-butylglycidyl acrylate, β-methylglycidyl acrylate, β-methylglycidyl methacrylate, β-ethylglycidyl acrylate, β-ethylglycidyl methacrylate, 3,4-epoxybutyl acrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7-epoxyheptyl methacrylate, α-ethyl-6,7-epoxyheptyl acrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, or a mixture comprising at least one of the foregoing unsaturated compounds containing an epoxy group.

4. The photoresist resin composition of claim 1 , wherein the unsaturated olefin-based compound comprises methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, methyl acrylate, isopropyl acrylate, cyclohexyl methacrylate, 2-methyl cyclohexyl methacrylate, dicyclopentanyl oxyethyl methacrylate, isobornyl methacrylate, cyclohexyl acrylate, 2-methyl cyclohexyl acrylate, dicyclopentenyl acrylate, dicyclopentanyl acrylate, dicyclopentenyl methacrylate, dicyclopentanyl methacrylate, dicyclopentanyl oxyethyl acrylate, isobornyl acrylate, phenyl methacrylate, phenyl acrylate, benzyl acrylate, benzyl methacrylate, 2-hydroxyethyl methacrylate, styrene, α-methyl styrene, m-methyl styrene, p-methyl styrene, vinyl toluene, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, or a mixture comprising at least one of the foregoing unsaturated olefin-based compounds.

5. The photoresist resin composition of claim 1 , wherein the quinone diazide compound comprises at least one selected from the group consisting of 1,2-quinone diazide-4-sulfonic acid ester, 1,2-quinone diazide-5-sulfonic acid ester, 1,2-quinone diazide-6-sulfonic acid ester, or a mixture comprising at least one of the foregoing quinone diazide compounds.

6. The photoresist resin composition of claim 1 , wherein the solvent comprises diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, or a mixture comprising at least one of the foregoing solvents.

7. The photoresist resin composition of claim 1 , wherein the acryl-based copolymer has a weight-average molecular weight of about 5,000 to about 30,000.

8. The photoresist resin composition of claim 1 , further comprising at least one additive comprising a melamine resin, an adhesive, an acryl-based compound, or a mixture comprising at least one of the foregoing additives.

9. The photoresist resin composition of claim 8 , wherein the additive is present in an amount of about 2 to about 3% by weight based on the total weight of the photoresist resin composition.

10. The photoresist resin composition of claim 9 , wherein the melamine resin is present in an amount of about 20 to about 30% by weight, the adhesive is present in an amount of about 45 to about 55% by weight, or the acryl-based copolymer is present in an amount of about 25 to about 30% by weight, wherein each of the melamine resin, the adhesive, or the acryl-based copolymer is based on the total weight of additive.

11. A method of forming a photoresist pattern, the method comprising: coating a photoresist resin composition on a surface of a substrate to form a photoresist layer, wherein the photoresist resin composition comprises about 10 to about 35% by weight of an acryl-based copolymer, about 5 to about 10% by weight of a quinone diazide compound, about 55 to about 80% by weight of a solvent, and about 0.01 to about 0.5% by weight of a silane-based surfactant represented by Chemical Formula (1):

wherein R 1 represents an ethylene oxide group, R 2 represents a propylene oxide group, and X and Y represent integers of about 1 to about 20, and wherein the weights of each of the acryl-based copolymer, quinone diazide compound, solvent, and silane-based surfactant are based on the total weight of acryl-based copolymer, quinone diazide compound, solvent, and silane-based surfactant; and

patterning the photoresist layer to form a photoresist pattern.

12. The method of claim 11 , wherein patterning the photoresist layer comprises:

selectively exposing the photoresist layer to light; and

developing the exposed photoresist layer.

13. The method of claim 12 , further comprising curing the photoresist layer after developing.

14. The method of claim 13 , wherein the curing of the developed photoresist layer is performed at a temperature of 150 to 200° C.

15. The method of claim 12 , wherein the selective exposing of the photoresist layer is performed using at least one selected from the group consisting of a g-line ray, an i-line ray, an emission line from a krypton fluoride excimer laser, an emission line from an argon fluoride excimer laser, an electron beam (e-beam), and an X-ray.

16. The method of claim 15 , wherein the developing of the exposed photoresist layer is performed using an aqueous solution comprising potassium hydroxide and/or tetramethyl ammonium hydroxide.

17. A method of manufacturing a display substrate comprising;

forming a gate metal pattern comprising a gate electrode, a gate line and a storage common line;

depositing a gate-insulating layer on the gate metal pattern;

sequentially forming an amorphous silicon layer and an n + amorphous silicon layer on the gate-insulating layer to form a channel layer;

forming a source metal pattern comprising a source line, a source electrode and a drain electrode on the gate-insulating layer having the channel layer;

coating a photoresist resin composition on the source metal pattern and the gate insulating layer, the photoresist resin composition comprising about 10 to about 35% by weight of an acryl-based copolymer, about 5 to about 10% by weight of a quinone diazide compound, about 55 to about 80% by weight of a solvent, and about 0.01 to about 0.5% by weight of a silane-based surfactant represented by Chemical Formula (1):

wherein R 1 represents an ethylene oxide group, R 2 represents a propylene oxide group, and X and Y represent integers of about 1 to about 20, and wherein the weights of each of the acryl-based copolymer, quinone diazide compound, solvent, and silane-based surfactant are based on the total weight of acryl-based copolymer, quinone diazide compound, solvent, and silane-based surfactant;

removing a portion of the photoresist resin composition and forming an overcoating layer having a contact hole exposing a portion of the drain electrode; and

forming a pixel electrode electrically connected to the drain electrode through the contact hole.

18. The method of claim 17 , wherein the acryl-based copolymer is prepared by copolymerizing monomers comprising about 5 to about 40% by weight of an unsaturated carboxylic acid, about 10 to about 70% by weight of an unsaturated compound containing an epoxy group, and about 10 to about 70% by weight of an unsaturated olefin-based compound, based on the total weight of the monomers.

19. The method of claim 17 , further comprising forming a passivation layer between the source metal pattern and the overcoating layer.

20. The method of claim 17 , wherein the overcoating layer has a convex-concave structure at an upper surface thereof.

21. The method of claim 17 , wherein the forming of the overcoating layer comprises:

exposing the photoresist resin composition to light by using a mask having a predetermined pattern;

developing the exposed photoresist resin composition; and

curing the developed photoresist resin composition at a temperature of about 150 to about 250° C.