IP Library Granted Patent US 10,539,874
Granted Patent B2
US 10,539,874 · App. 15/609,471 · Granted Jan 21, 2020

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

Inventors: Hyo Jung Roh (Hwaseong-si, KR); Ji Hyun Kim (Hwaseong-si, KR); Seung Jin Kim (Hwaseong-si, KR); Hyun Jin Kim (Hwaseong-si, KR)
Assignee: DONGJIN SEMICHEM CO., LTD.
G03F7/091B05D3/0272B05D5/00C09D5/006C09D125/18G02B1/111G03F7/038G03F7/168
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,539,874
App. No.
15/609,471
Granted
Jan 21, 2020
Kind
B2
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.

Claims (18)

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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 31, 2017
From: ROH, HYO JUNG; KIM, JI HYUN; KIM, SEUNG JIN; KIM, HYUN JIN
To: DONGJIN SEMICHEM CO., LTD.
Reel/Frame 042543/0056 →
Priority Claims (1)
KR 10-2016-0067944 · Jun 1, 2016 · national
Continuity (1)
Related Publication 20170351178A1 · Dec 7, 2017