Organic anti-reflective layer composition containing ring-opened phthalic anhydride and method for preparation thereof

• US 20100055408A1
• Filed: 01/15/2009
• Published: 03/04/2010
• Est. Priority Date: 08/26/2008
• Status: Abandoned Application

• Current Assignee: Korea Kumho Petrochemical Co Limited (Korea Kumho Petrochemical)
• Original Assignee: Korea Kumho Petrochemical Co Limited (Korea Kumho Petrochemical)
• Inventors: Lee, Jun-Ho, Lee, Jong-Don, Hong, Seung-Hee, Bae, Shin-Hyo, Cho, Seung-Duk
• Application Number:
  US12/321,091
• Publication Number:
  US 20100055408A1
• Time in Patent Office: Days
• US Class Current: 428/172
• CPC Class Codes: C07C 2602/44 the bicyclo ring system containing eight carbon atoms
• CPC Class Codes: C07C 317/44 having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
• CPC Class Codes: C07C 323/62 having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
• CPC Class Codes: C07C 69/753 of polycyclic acids
• CPC Class Codes: C07C 69/76 Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 69/92 with etherified hydroxyl groups
• CPC Class Codes: G03F 7/091 characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
• CPC Class Codes: Y10T 428/24612 Composite web or sheet

Abstract

A light absorbent for forming an organic anti-reflective layer, represented by the following formula 1 or formula 2, is provided:

wherein A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group and containing one or more heteroatoms, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted heteroalicyclic group, a substituted or unsubstituted diaryl ether, a substituted or unsubstituted diaryl sulfide, a substituted or unsubstituted diaryl sulfoxide, a substituted or unsubstituted diaryl ketone, or a substituted or unsubstituted diaryl bisphenol A; R₁, R₂, and R₃ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group a substituted or unsubstituted aryl group, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group; and n is an integer from 2 to 500.

Claims

1. A light absorbent for forming an organic anti-reflective layer, represented by the following formula 1:

wherein A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group having 1 to 20 carbon atoms and containing one or more heteroatoms, a substituted or unsubstituted aromatic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3 to 20 carbon atoms, a substituted or unsubstituted alicyclic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroalicyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ether having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfoxide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ketone having 3 to 20 carbon atoms, or a substituted or unsubstituted diaryl bisphenol A having 3 to 20 carbon atoms; and

R₁ and R₂ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group.

3. The light absorbent for forming an organic anti-reflective layer according to claim 1, wherein the light absorbent represented by the formula 1 is a compound produced by a reaction in the presence of a base.

4. The light absorbent for forming an organic anti-reflective layer according to claim 3, wherein the base is a compound selected from the group consisting of dimethylaminopyridine, pyridine, 1,4-diazabicyclo[2,2,2]octane, 1,5-diazabicyclo[4,3,0]nonane, triethylamine, 2,6-di-tert-butylpyridine, diisopropylethylamine, diazabicycloundecene, tetramethylethylenediamine and tetrabutylammonium bromide.

2. A light absorbent for forming an organic anti-reflective layer, represented by the following formula 2:

wherein A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group having 1 to 20 carbon atoms and containing one or more heteroatoms, a substituted or unsubstituted aromatic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3 to 20 carbon atoms, a substituted or unsubstituted alicyclic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroalicyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ether having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfoxide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ketone having 3 to 20 carbon atoms, or a substituted or unsubstituted diaryl bisphenol A having 3 to 20 carbon atoms;

R₃ represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group; and

n is an integer from 2 to 500.

15. The light absorbent for forming an organic anti-reflective layer according to claim 2, wherein the light absorbent represented by the formula 2 is a compound produced by a reaction in the presence of a base.

16. The light absorbent for forming an organic anti-reflective layer according to claim 15, wherein the base is a compound selected from the group consisting of dimethylaminopyridine, pyridine, 1,4-diazabicyclo[2,2,2]octane, 1,5-diazabicyclo[4,3,0]nonane, triethylamine, 2,6-di-tert-butylpyridine, diisopropylethylamine, diazabicycloundecene, tetramethylethylenediamine and tetrabutylammonium bromide.

5. An organic anti-reflective layer composition comprising a light absorbent represented by the following formula 1 or formula 2, a polymer, a thermal acid generating agent, a crosslinking agent and a solvent:

wherein A represents a substituted or unsubstituted, linear or branched, saturated tetravalent hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted, linear or branched, saturated hydrocarbon group having 1 to 20 carbon atoms and containing one or more heteroatoms, a substituted or unsubstituted aromatic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3 to 20 carbon atoms, a substituted or unsubstituted alicyclic group having 4 to 20 carbon atoms, a substituted or unsubstituted heteroalicyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ether having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl sulfoxide having 3 to 20 carbon atoms, a substituted or unsubstituted diaryl ketone having 3 to 20 carbon atoms, or a substituted or unsubstituted diaryl bisphenol A having 3 to 20 carbon atoms;

R₁, R₂ and R₃ each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted acetal group, or a substituted or unsubstituted hydroxyl group; and

n is an integer from 2 to 500.

6. The organic anti-reflective layer composition according to claim 5, wherein the composition comprises 0.1 to 5% by weight of the light absorbent, 0.1 to 5% by weight of the polymer, 0.01 to 1% by weight of the thermal acid generating agent, and 0.05 to 5% by weight of the crosslinking agent.

7. The organic anti-reflective layer composition according to claim 5, wherein the polymer is a resin having crosslinking sites at the terminals of the main chain or side chains.

8. The organic anti-reflective layer composition according to claim 5, wherein the crosslinking agent is an aminoplastic compound, a polyfunctional epoxy resin, an anhydride or a mixture thereof, which respectively has two or more crosslinkable functional groups.

9. The organic anti-reflective layer composition according to claim 5, wherein the thermal acid generating agent is toluenesulfonic acid, an amine salt of toluenesulfonci acid, a pyridine salt of toluenesulfonic acid, alkylsulfonic acid, an amine salt of alkylsulfonic acid, or a pyridine salt of alkylsulfonic acid.

10. The organic anti-reflective layer composition according to claim 5, wherein the solvent is one or more selected from the group consisting of propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, propylene glycol n-propyl ether, dimethylformamide (DMF), γ

-butyrolactone, ethoxyethanol, methoxyethanol, methyl 3-methoxypropionate (MMP) and ethyl 3-ethoxypropionate (EEP).

11. A method for patterning a semiconductor device, the method comprising:

applying the organic anti-reflective layer composition according to claim 5 on top of a layer to be etched;

curing the applied composition through a baking process, and forming crosslinking bonds to form an organic anti-reflective layer;

applying a photoresist on top of the organic anti-reflective layer, and exposing and developing the photoresist to form a photoresist pattern; and

etching the organic anti-reflective layer using the photoresist pattern as an etching mask, and then etching the layer to be etched so as to pattern the layer to be etched.

12. The method for patterning a semiconductor device according to claim 11, wherein the baking process during the curing is carried out at a temperature of 150°

C. to 250°

C. for 0.5 minutes or 5 minutes.

13. The method for patterning a semiconductor device according to claim 11, further comprising a second baking process before or after exposing during the forming a photoresist pattern.

14. A semiconductor device produced by the method for patterning according to claim 11.

17. The organic anti-reflective layer composition according to claim 6, wherein the polymer is a resin having crosslinking sites at the terminals of the main chain or side chains.

18. The organic anti-reflective layer composition according to claim 6, wherein the crosslinking agent is an aminoplastic compound, a polyfunctional epoxy resin, an anhydride or a mixture thereof, which respectively has two or more crosslinkable functional groups.

19. The organic anti-reflective layer composition according to claim 6, wherein the thermal acid generating agent is toluenesulfonic acid, an amine salt of toluenesulfonci acid, a pyridine salt of toluenesulfonic acid, alkylsulfonic acid, an amine salt of alkylsulfonic acid, or a pyridine salt of alkylsulfonic acid.

20. The organic anti-reflective layer composition according to claim 6, wherein the solvent is one or more selected from the group consisting of propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), cyclohexanone, ethyl lactate, propylene glycol n-propyl ether, dimethylformamide (DMF), γ

-butyrolactone, ethoxyethanol, methoxyethanol, methyl 3-methoxypropionate (MMP) and ethyl 3-ethoxypropionate (EEP).