COMPOSITION FOR RADICAL POLYMERIZATION AND METHOD OF FORMING PATTERN USING THE COMPOSITION

• US 20100119976A1
• Filed: 06/05/2009
• Published: 05/13/2010
• Est. Priority Date: 11/11/2008
• Status: Active Grant

• Current Assignee: Samsung Electronics Co. Ltd.
• Original Assignee: Samsung Electronics Co. Ltd.
• Inventors: Choi, Yun-hyuk, Lee, Kwang-sup, Lee, Kwang-hee, Park, Jong-jin, Bulliard, Xavier
• Granted Patent: US 8,445,178 B2
• Time in Patent Office: Days
• US Class Current: 430/286.100
• CPC Class Codes: G03F 7/031 Organic compounds not covered by group G03F7/029
• CPC Class Codes: G03F 7/033 the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
• CPC Class Codes: G03F 7/2053 using a laser ablative removal B41C

Abstract

A composition for radical polymerization includes a photosensitive material, a photoinitiator, a solvent, and a material for adjusting a size of a pattern. A method of forming a pattern using the composition is also disclosed.

Claims

1. A composition for radical polymerization, comprising a photosensitive material, a photoinitiator, a solvent, and a material for adjusting the size of a pattern.

2. The composition for radical polymerization of claim 1, wherein the material for adjusting the size of a pattern is a radical scavenger.

3. The composition for radical polymerization of claim 2, wherein the radical scavenger is selected from the group consisting of 2,2,6,6-tetramethyl-1-piperidinyloxy free radical represented by Formula 1 below;

isoprene;

diisobutylene;

α

-tocopherol, β

-tocopherol, γ

-tocopherol, δ

-tocopherol;

4,6-bis(octylthiomethyl)-o-cresol;

4,6-bis(dodecylthiomethyl)-o-cresol;

4,4′

-thiobis(2-methyl-6-t-butylphenol), 4,4′

-thiobis(2-t-butyl-5-methylphenol);

2,2′

-thiobis(6-t-butyl-4 methylphenol);

2,2′

-thiobis 4-octyl phenol 4,4′

-thiobis(2-t-butyl-5-methylphenol), triethylene glycol bis[3-[3,5-t-butyl-4-hydroxy-5-methylphenyl)propionate;

1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione;

2,5-di-t-amylhydroquinone;

a reaction product of 4-methylphenol with dicyclopentadiene and isobutylene;

oxidized bis(hydrogenated tallow alkyl)amine;

bis-(1-octyloxy-2,2,6,6 tetramethyl-4-piperidinyl)sebacate;

4,4′

-bis(α

,α

-dimethylbenzyl)diphenylamine, N-phenyl-styrenated benzenamine, a reaction product of diphenylamine and acetone, p-(p-toluene-sulfonyl amido)-diphenylamine;

2,2-thiodiethylene bis[3(3-t-butyl-4-hydroxy-5 methylphenyl)propionate];

2,2-thiodiethylene bis[3(3,5-di-methyl-4-hydroxyphenyl)propionate];

galvinoxyl free radical represented by Formula 2 below;

derivatives thereof, and any mixture thereof;

4. The composition for radical polymerization of claim 1, wherein the material for adjusting a size of a pattern comprises at least one selected from the group consisting of a polymer-containing radical scavenger, a photosensitizer, and any combination thereof.

5. The composition for radical polymerization of claim 4, wherein a polymer of the polymer-containing radical scavenger is selected from the group consisting of polystyrene, poly(methyl)methacrylate, polymethacrylate, poly(methyl)acrylate, polyacrylate, derivatives thereof, and any combination thereof.

6. The composition for radical polymerization of claim 4, wherein the photosensitizer is selected from the group consisting of Michler'"'"'s ketone represented by Formula 3 below, a colorant, an organic acid, an organic acid salt, an organic amine, a triarylmethane-based material, a thiol-group-containing hetero aromatic-based material, a metal complex, and any combination thereof:

7. The composition for radical polymerization of claim 1, further comprising a quantum dot.

8. The composition for radical polymerization of claim 1, further comprising a two photon absorption material.

9. A method of forming a pattern, comprising:

preparing a first composition for radical polymerization including a photosensitive material, a photoinitiator, a solvent, and a material for adjusting a size of a pattern;

applying the first composition for radical polymerization to a surface of a substrate to form a first film;

irradiating the first film with light having a first energy according to a first pattern to selectively expose the first film; and

developing the light-exposed first film to obtain the first pattern.

10. The method of claim 9, wherein when a radical scavenger comprises the material for adjusting the size of the pattern, the size of the first pattern is adjusted to be smaller than the size of a second pattern, wherein the second pattern is obtained by applying, to a surface of a substrate, a second composition for radical polymerization including a photosensitive material, a photoinitiator, and a solvent in a same weight ratio as corresponding components in the first composition for radical polymerization, to obtain a second film with a thickness the same as that of the first film, then irradiating the second film with light having a first energy according to the first pattern to selectively expose the second film to light and developing the light-exposed second film, to form a second pattern.

11. The method of claim 10, wherein the radical scavenger is selected from the group consisting of 2,2,6,6-tetramethyl-1-piperidinyloxy free radical represented by Formula 1 below;

isoprene;

diisobutylene;

α

-tocopherol, β

-tocopherol, γ

-tocopherol, δ

-tocopherol;

4,6-bis(octylthiomethyl)-o-cresol;

4,6-bis(dodecylthiomethyl)-o-cresol;

4,4′

-thiobis(2-methyl-6-t-butylphenol), 4,4′

-thiobis(2-t-butyl-5-methylphenol);

2,2′

-thiobis(6-t-butyl-4 methylphenol);

2,2′

-thiobis 4-octyl phenol;

4,4′

-thiobis(2-t-butyl-5-methylphenol), triethylene glycol bis[3-[3,5-t-butyl-4-hydroxy-5-methylphenyl)propionate;

1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione;

2,5-di-t-amylhydroquinone;

a reaction product of 4-methylphenol with dicyclopentadiene and isobutylene;

oxidized bis(hydrogenated tallow alkyl)amine;

bis-(1-octyloxy-2,2,6,6 tetramethyl-4-piperidinyl)sebacate;

4,4′

-bis(α

,α

-dimethylbenzyl)diphenylamine, N-phenyl-styrenated benzenamine, a reaction product of diphenylamine and acetone, p-(p-toluene-sulfonyl amido)-diphenylamine;

2,2-thiodiethylene bis[3(3-t-butyl-4-hydroxy-5 methylphenyl)propionate];

2,2-thiodiethylene bis[3(3,5-di-methyl-4-hydroxyphenyl)propionate];

galvinoxyl free radical represented by Formula 2 below, derivatives thereof, and mixtures thereof;

12. The method of claim 9, wherein, when at least one material selected from the group consisting of a polymer-containing radical scavenger, a photosensitizer, and any combination thereof, as the material for adjusting the size of the pattern of the first composition for radical polymerization, the size of the first pattern is adjusted to be larger than a size of a second pattern, wherein the second pattern is obtained by applying, to a surface of a substrate, a second composition for radical polymerization comprising a photosensitive material, a photoinitiator, and a solvent, wherein each of these components is present in the same weight ratio as corresponding components in the first composition for radical polymerization, to obtain a second film with the same thickness as that of the first film, then irradiating the second film with light having a first energy according to the first pattern to selectively expose the second film;

and developing the light-exposed second film to obtain a second pattern.

13. The method of claim 12, wherein a polymer of the polymer-containing radical scavenger is selected from the group consisting of polystyrene, poly(methyl)methacrylate, polymethacrylate, poly(methyl)acrylate, polyacrylate, derivatives thereof, and any combination thereof.

14. The method of claim 12, wherein the photosensitizer is selected from the group consisting of Michler'"'"'s ketone represented by Formula 3 below, a colorant, an organic acid, an organic acid salt, an organic amine, a triarylmethane-based material, a thiol-group-containing hetero aromatic-based material, a metal complex, and any combination thereof:

15. The method of claim 9, wherein the first composition for radical polymerization further comprises a quantum dot, and the first pattern comprises the quantum dot.

16. The method of claim 9, wherein the first composition for radical polymerization further comprises a two photon absorption material.

17. The method of claim 9, wherein the irradiating is performed using a laser beam which induces two-photon absorption, and the first pattern has a three-dimensional form.

18. The method of claim 9, wherein the size of the first pattern is about 1,000 micrometers or less.