Composition for forming organic anti-reflective coating layer suitable for negative tone development

Patent metadata

Field	Value
Publication number	US-10539874-B2
Application number	US-201715609471-A
Country	US
Kind code	B2
Filing date	May 31, 2017
Priority date	Jun 1, 2016
Publication date	Jan 21, 2020
Grant date	Jan 21, 2020

Abstract

Provided is a composition for forming an organic anti-reflective coating layer used in a negative tone development, which not only enhance an adhesion to a photoresist while having a high refractive index and a high etch rate but also improve a pattern profile of undercut etc. The composition an isocyanurate compound containing at least one moiety which is represented by Formula 2; a polymer represented by Formula 3 and an organic solvent for dissolving the above-mentioned components.

First claim

The invention claimed is:

1. A composition for forming an organic anti-reflective coating layer comprising:
an isocyanurate compound containing at least one moiety which is represented by following Formula 2;
a polymer represented by following Formula 3; and
an organic solvent for dissolving the above-mentioned components,

in Formula 2, R is independently a hydrogen atom or a methyl group, R′ is independently a chain or cyclic saturated or unsaturated hydrocarbyl group of 1 to 15 carbon atoms containing 0 to 6 of hetero atoms, and R″ is independently a chain or cyclic saturated or unsaturated hydrocarbyl group of 1 to 15 carbon atoms containing 0 to 8 of hetero atoms, and two or more moieties represented by the formula 2 are connected through R′,
In Formula 3, R 1 is independently a hydrogen or a methyl group (—CH 3 ), R 2 is a hydroxyl group (—OH) or an alkoxyl group of 1 to 5 carbon atoms containing 0 to 2 hydroxyl groups, R 3 is a chain or cyclic saturated or unsaturated hydrocarbyl group of 3 to 15 carbon atoms containing 0 to 2 of hetero atoms, R 4 is an aryl group of 5 to 15 carbon atoms containing 0 to 3 of hetero atoms, x, y and z each is the mole % of each repeating unit constituting the polymer, x is 40 to 70 mole %, y is 5 to 25 mole % and z is 15 to 45 mole %.

2. The composition for forming an organic anti-reflective coating layer of claim 1 , wherein the amount of the isocyanurate compound is 1 to 10 weight %, the amount of the polymer is 0.1 to 5 weight % and the amount of the organic solvent is 85 to 98.9 weight %.

3. The composition for forming an organic anti-reflective coating layer of claim 1 , further comprising: 0.01 to 0.4 weight % of a crosslinking agent for crosslinking the isocyanurate compound; and 0.02 to 0.5 weight % of an acid generator for promoting the crosslinking reaction of the isocyanurate compound and for supplying acids to a lower part of a photoresist.

4. The composition for forming an organic anti-reflective coating layer of claim 1 , wherein R′ is independently an alkyl group of 1 to 10 carbon atoms containing 0 to 2 of hetero atoms, R″ is independently (i) an alkyl group of 1 to 10 carbon atoms containing 0 to 2 of hetero atoms, or (ii) a cycloalkyl group, an aryl group or a heterocyclic group of 4 to 10 carbon atoms containing 0 to 2 hetero atoms,
R 2 is an alkoxy group of 1 to 3 carbon atoms containing 0 to 2 hydroxyl groups, R 3 is an alkyl group or cycloalkyl group of 3 to 12 carbon atoms containing 0 to 2 hydroxyl groups, or a heterocyclic group of 3 to 12 carbon atoms containing 1 to 2 oxygen atoms, and R 4 is an aryl group of 6 to 12 carbon atoms containing 0 to 2 oxygen atoms.

5. The composition for forming an organic anti-reflective coating layer of claim 1 , wherein the weight average molecular weight of the polymer is 3,000 to 10,000.

6. The composition for forming an organic anti-reflective coating layer of claim 1 , wherein the isocyanurate compound represented by the Formula 2 is a compound containing repeating units represented by the following formulas 2a to 2h, and is selected from a group consisting of

and mixture thereof, and the polymer represented by Formula 3 is selected from a group consisting of

(in Formulas 3a to 3g, x, y and z are the same as defined in Formula 3) and mixture thereof.

7. The composition for forming an organic anti-reflective coating layer of claim 1 , wherein the organic solvent is selected from a group of cyclohexanone, cyclopentanone, butyrolactone, dimethylacetamide, dimethylformamide, dimethylsulfoxide, N-methyl pyrrolidone (NMP), tetrahydro furfural alcohol, propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), ethyl lactate, mixtures thereof.

8. A method for forming an organic anti-reflective coating layer comprising of: coating the composition for forming an organic anti-reflective coating layer of claim 1 on an etching layer; and crosslinking the composition for forming an organic anti-reflective coating layer which is coated.

9. The method for forming an organic anti-reflective coating layer of claim 8 , wherein the amount of the isocyanurate compound is 1 to 10 weight %, the amount of the polymer is 0.1 to 5 weight % and the amount of the organic solvent is 85 to 98.9 weight %.

10. The method for forming an organic anti-reflective coating layer of claim 8 , further comprising: 0.01 to 0.4 weight % of a crosslinking agent for crosslinking the isocyanurate compound; and 0.02 to 0.5 weight % of an acid generator for promoting the crosslinking reaction of the isocyanurate compound and for supplying acids to a lower part of a photoresist.

Assignees

• Dongjin Semichem Co Ltd

Inventors

• Roh Hyo Jung
• Kim Ji Hyun
• Kim Seung Jin
• Kim Hyun Jin

Classifications

• C08K5/41

  Compounds containing sulfur bound to oxygen · CPC title

• C09D7/20

  Diluents or solvents · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title

• C08K5/05

  Alcohols; Metal alcoholates · CPC title

• C08K5/07

  Aldehydes; Ketones · CPC title