Method of forming patterns and method of manufacturing integrated circuit device using the same

Patent metadata

Field	Value
Publication number	US-10134606-B2
Application number	US-201514712920-A
Country	US
Kind code	B2
Filing date	May 15, 2015
Priority date	May 20, 2014
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

A method of forming patterns may use an organic reflection-preventing film including a polymer having an acid-liable group. A photoresist film is formed on the organic reflection-preventing film. A first area selected from the photoresist film is exposed to generate an acid in the first area. Hydrophilicity of a first surface of the organic reflection-preventing film facing the first area of the photoresist film may be increased. The photoresist film including the exposed first area is developed to remove a non-exposed area of the photoresist film. The organic reflection-preventing film and a target layer are anisotropically etched by using the first area of the photoresist film as an etch mask.

First claim

What is claimed is:

1. A method of manufacturing patterns, the method comprising:
forming an organic reflection-preventing film, comprising a polymer having an acid-labile group, on a target layer,
forming a photoresist film comprising a photoacid generator (PAG) on the organic reflection-preventing film,
selectively exposing the photoresist film to a light source including exposing at least a first area of the photoresist film to the light source while not exposing at least a second area of the photoresist film to the light source to generate an acid in the first area, thereby increasing hydrophilicity of a first surface of the organic reflection-preventing film facing the first area of the photoresist film using the acid,
developing the photoresist film having the exposed first area to remove the second area of the photoresist film therefrom, and
anisotropically etching the organic reflection-preventing film and the target layer by using the first area of the photoresist film as an etch mask,
wherein after the developing, a bottom surface of the photoresist film has a first contact angle with respect to deionized water and the first surface of the organic reflection-preventing film has a second contact angle with respect to deionized water, and
wherein a difference between the first contact angle and the second contact angle is in a range of −3° to +3°.

2. The method of claim 1 , wherein
the increasing of hydrophilicity of the first surface comprises deprotecting the polymer by removing the acid-labile group at the first surface of the organic reflection-preventing film by using an acid generated from the PAG.

3. The method of claim 1 , wherein
the developing comprises using a negative tone developer to remove the second area of the photoresist film.

4. The method of claim 1 , wherein
the polymer of the organic reflection-preventing film comprises a repeating unit comprising an acrylate derivative having the acid-labile group.

5. The method of claim 1 , wherein
the polymer of the organic reflection-preventing film comprises a repeating unit having the acid-labile group, and
an amount of the repeating unit having the acid-labile group is in a range of 1 to 40 mol % based on a total amount of the polymer.

6. The method of claim 1 , wherein
the organic reflection-preventing film comprises a second polymer having a protecting group substituted with fluorine.

7. The method of claim 1 , wherein
the exposing is performed by immersion lithography.

8. The method of claim 1 , wherein
in the developing of the photoresist film, at least a portion of a portion of the organic reflection-preventing film under the second area of the photoresist film is not removed by the developing.

9. The method of claim 1 , wherein
after the developing of the photoresist film, prior to the anisotropic etching of the organic reflection-preventing film and the target layer using the first area of the photoresist film as a mask, the target layer is completely covered by the organic reflection-preventing film so that an upper surface of the target layer is not exposed to an outside atmosphere.

10. A method of manufacturing patterns, the method comprising:
forming an organic reflection-preventing film comprising a first polymer having an acid-labile group on a target layer,
forming a photoresist film on the organic reflection-preventing film,
selectively exposing at least a first area of the photoresist film to a light source while not exposing at least a second area of the photoresist film to the light source and increasing hydrophilicity of a first surface of the organic reflection-preventing film facing the first area of the photoresist film, and
forming an opening exposing a portion of the organic reflection-preventing film by removing a second area of the photoresist film,
wherein after the hydrophilicity of the first surface of the organic reflection-preventing film is increased, a first contact angle of the first surface of the organic reflection-preventing film with respect to deionized water and a second contact angle of a bottom surface of the photoresist film with respect to deionized water differ no more than five degrees.

11. The method of claim 10 , wherein
the increasing of hydrophilicity in the first surface comprises deprotecting the first polymer by removing the acid-labile group from the first polymer of the organic reflection-preventing film.

12. The method of claim 10 ,
wherein the first polymer of the organic reflection-preventing film is represented by

and
wherein the organic reflection-preventing film further comprises a second polymer represented by

wherein R 1 is a hydrogen (H) or a methyl group (—CH 3 ),
R 2 is S, O, or NH,
R 3 is a heterocyclic group comprising sulfur (S),
R 4 is a hydroxyl group (—OH),
R 5 is a phenyl group,
R 6 is a hydroxyl group (—OH) or a methoxy group (—OCH 3 ), and
R 7 is a deprotecting group obtained from at least one of the following monomers represented by

13. The method of claim 12 ,
wherein the organic reflection-preventing film further comprises a third polymer represented by

wherein R 8 is a fluoro group.

14. The method of claim 12 , wherein the first polymer is prepared to form an organic reflection-preventing film, the preparation comprising:
a first reaction process, wherein a heterocyclic compound containing sulfur (S) is reacted with (meth)acrylic acid or (meth)acrylic acid halide to obtain an unsaturated ethylene monomer including R2 and R3;
a second reaction process, wherein a compound having a hydroxyl group (—OH) is reacted with (meth)acrylic acid or (meth)acrylic acid halide to obtain an unsaturated ethylene monomer having R2 and R4; and
a third reaction process, wherein a compound having a phenyl group is reacted with (meth)acrylic acid or (meth)acrylic acid halide to obtain an unsaturated ethylene monomer having R2 and R5.

15. The method of claim 12 ,
wherein the organic reflection-preventing film further comprises a third polymer obtained from at least one of the following monomers represented by

16. The method of claim 10 , wherein
an amount of the first polymer comprising the acid-labile group in the organic reflection-preventing film is in a range of 1 to 40 mol % based on a total polymer amount of the organic reflection-preventing film.

17. The method of claim 10 , wherein
in the forming of the opening, a negative tone developer is used to remove the second area of the photoresist film, and
the organic reflection-preventing film has a first solubility with respect to the negative tone developer, and the first solubility is smaller than a second solubility of the photoresist film with respect to the negative tone developer.

18. A method of manufacturing patterns, the method comprising:
forming an organic reflection-preventing film comprising an acid-labile group on a target layer,
forming a photoresist film covering the organic reflection-preventing

Assignees

• Samsung Electronics Co Ltd

Inventors

• Woo Sang-Yoon
• Kim Hyun-Woo
• An Ju-Hyung
• Yoon Jin-Young

Classifications

• H10P76/2043

  using an anti-reflective coating · CPC title

• H10P76/405

  characterised by their composition, e.g. multilayer masks · CPC title

• H10P76/204 Primary

  of organic photoresist masks · CPC title

• H10P50/692

  characterised by their composition, e.g. multilayer masks or materials · CPC title

• H10P50/73

  using masks for insulating materials · CPC title