Compound for forming organic film, composition for forming organic film, method for forming organic film, and patterning process

• US 10,429,739 B2
• Filed: 11/22/2016
• Issued: 10/01/2019
• Est. Priority Date: 12/24/2015
• Status: Active Grant

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Kori, Daisuke, Ogihara, Tsutomu, Watanabe, Takeru, Taneda, Yoshinori, Kikuchi, Rie
• Primary Examiner(s): Walke, Amanda C.
• Application Number:
  US15/359,323
• Publication Number:
  US 20170183531A1
• Time in Patent Office: 1,043 Days
• Field of Search: 430322, 430325, 430329, 430330, 430331, 4302701, 4302711
• CPC Class Codes: C08G 2261/135 Cross-linked structures
• CPC Class Codes: C08G 2261/3424 non-conjugated, e.g. paracyclophanes or xylenes
• CPC Class Codes: C08G 2261/76 crosslinking
• CPC Class Codes: C08G 8/08 of formaldehyde, e.g. of formaldehyde formed in situ
• CPC Class Codes: C09D 149/00 Coating compositions based on homopolymers or copolymers of compounds having one or more carbon-to-carbon triple bonds; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 155/00 Coating compositions based on homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C09D123/00 - C09D153/00
• CPC Class Codes: C09D 165/00 Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C09D107/00 - C09D157/00, C09D161/00 take precedence; Coating compositions based on derivatives of such polymers
• CPC Class Codes: G03F 7/004 Photosensitive materials G03F7/12, G03F7/14 take precedence
• CPC Class Codes: G03F 7/0397 the macromolecular compound having an alicyclic moiety in a side chain
• CPC Class Codes: G03F 7/0752 in non photosensitive layers or as additives, e.g. for dry lithography
• 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: G03F 7/094 Multilayer resist systems, e.g. planarising layers
• CPC Class Codes: G03F 7/16 Coating processes; Apparatus therefor applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74
• CPC Class Codes: G03F 7/168 Finishing the coated layer, e.g. drying, baking, soaking
• CPC Class Codes: G03F 7/2041 in the presence of a fluid, e.g. immersion; using fluid cooling means
• CPC Class Codes: G03F 7/322 Aqueous alkaline compositions
• CPC Class Codes: G03F 7/325 Non-aqueous compositions
• CPC Class Codes: H01L 21/02118 carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC polymers per se C08G, photoresist per se G03F
• CPC Class Codes: H01L 21/02282 liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
• CPC Class Codes: H01L 21/0274 Photolithographic processes
• CPC Class Codes: H01L 21/0276 : using an anti-reflective coating anti-reflective coating for lithography in general G03F7/09
• CPC Class Codes: H01L 21/0332 : characterised by their composition, e.g. multilayer masks, materials
• CPC Class Codes: H01L 21/31051 : Planarisation of the insulating layers H01L21/31058 takes precedence

Abstract

The present invention provides a compound for forming an organic film which has a minimum complex viscosity of 10 Pa·s or less when the complex viscosity is measured within a range of 50° C. to 300° C. This compound for forming an organic film can provide an organic film composition having high filling and planarizing properties.

Claims

1. A compound for forming an organic film which has a minimum complex viscosity of 10 Pa·

s or less when the complex viscosity is measured within a range of 50°

C. to 300°

C.,

wherein the compound is shown by the formula (1A),

RR₁)_(m1+m2) 

 

(1A)

wherein R represents a single bond, an organic group having 1 to 50 carbon atoms, an ether bond, a —

SO—

group, or a —

SO₂—

group;

R₁ represents a group shown by the formula (1B); and

m1 and m2 represent an integer satisfying 1≤

m1≤

5, 1≤

m2≤

5, and 2≤

m1+m2≤

8,

—

R₁=—

X¹—

X 

 

(1B)

wherein X¹ represents a group shown by the formula (1C); and

X represents a group shown by the formula (1D),

2. The compound for forming an organic film according to claim 1, wherein the compound has a complex viscosity of 1,000 Pa·

s or less at 100°

C.

3. The compound for forming an organic film according to claim 1, wherein the compound has a molecular weight of 2,500 or less.

4. A composition for forming an organic film, comprising the compound according to claim 1 and an organic solvent.

7. A method for forming an organic film that functions as an organic planarizing film used in a semiconductor apparatus manufacturing process, the method comprising:

applying the composition for forming an organic film according to claim 4 on a substrate to be processed by spin coating; and

heating the substrate, on which the composition has been applied, at 100°

C. to 600°

C. for 10 to 600 seconds to form a cured film.

8. The method for forming an organic film according to claim 7, wherein the substrate to be processed has steps or a structure with a height of 30 nm or more.

9. A method for forming an organic film that functions as an organic planarizing film used in a semiconductor apparatus manufacturing process, the method comprising:

applying the composition for forming an organic film according to claim 4 on a substrate to be processed by spin coating; and

heating the substrate, on which the composition has been applied, under an atmosphere having an oxygen concentration of 0.1% to 21% to form a cured film.

10. A patterning process comprising:

forming an organic film on a body to be processed from the composition for forming an organic film according to claim 4;

forming a resist underlayer film on the organic film from a resist underlayer film composition containing a silicon atom;

forming a resist upper layer film on the resist underlayer film from a resist upper layer film composition composed of a photoresist composition;

forming a circuit pattern in the resist upper layer film;

transferring the pattern to the resist underlayer film by etching using the resist upper layer film having the formed circuit pattern as a mask;

transferring the pattern to the organic film by etching using the resist underlayer film having the transferred pattern as a mask; and

further transferring the pattern to the body to be processed by etching using the organic film having the transferred pattern as a mask.

11. The patterning process according to claim 10, the circuit pattern is formed by a photolithography with a wavelength ranging from 10 nm to 300 nm, a direct drawing with electron beam, a nanoimprinting, or a combination thereof.

12. The patterning process according to claim 10, the circuit pattern is developed by alkaline development or development with an organic solvent.

13. The patterning process according to claim 10, wherein the body to be processed is a semiconductor apparatus substrate or the semiconductor apparatus substrate coated with any of a metal film, a metal carbide film, a metal oxide film, a metal nitride film, a metal oxycarbide film, and a metal oxynitride film.

14. The patterning process according to claim 13, wherein the metal of the body to be processed is silicon, titanium, tungsten, hafnium, zirconium, chromium, germanium, copper, silver, gold, aluminum, indium, gallium, arsenic, palladium, iron, tantalum, iridium, molybdenum, or an alloy thereof.

15. A patterning process comprising:

forming an organic film on a body to be processed from the composition for forming an organic film according to claim 4;

forming a resist underlayer film on the organic film from a resist underlayer film composition containing a silicon atom;

forming an organic antireflective film on the resist underlayer film;

forming a resist upper layer film on the organic antireflective film from a resist upper layer film composition composed of a photoresist composition;

forming a circuit pattern in the resist upper layer film;

transferring the pattern to the organic antireflective film and the resist underlayer film by etching using the resist upper layer film having the formed circuit pattern as a mask;

transferring the pattern to the organic film by etching using the resist underlayer film having the transferred pattern as a mask; and

further transferring the pattern to the body to be processed by etching using the organic film having the transferred pattern as a mask.

16. A patterning process comprising:

forming an organic film on a body to be processed from the composition for forming an organic film according to claim 4;

forming an inorganic hard mask selected from a silicon oxide film, a silicon nitride film, and a silicon oxynitride film on the organic film;

forming a resist upper layer film on the inorganic hard mask from a resist upper layer film composition composed of a photoresist composition;

forming a circuit pattern in the resist upper layer film;

transferring the pattern to the inorganic hard mask by etching using the resist upper layer film having the formed circuit pattern as a mask;

transferring the pattern to the organic film by etching using the inorganic hard mask having the transferred pattern as a mask; and

further transferring the pattern to the body to be processed by etching using the organic film having the transferred pattern as a mask.

17. The patterning process according to claim 16, wherein the inorganic hard mask is formed by a CVD method or an ALD method.

18. A patterning process comprising:

forming an organic film on a body to be processed from the composition for forming an organic film according to claim 4;

forming an inorganic hard mask selected from a silicon oxide film, a silicon nitride film, and a silicon oxynitride film on the organic film;

forming an organic antireflective film on the inorganic hard mask;

forming a resist upper layer film on the organic antireflective film from a resist upper layer film composition composed of a photoresist composition;

forming a circuit pattern in the resist upper layer film;

transferring the pattern to the organic antireflective film and the inorganic hard mask by etching using the resist upper layer film having the formed circuit pattern as a mask;

transferring the pattern to the organic film by etching using the inorganic hard mask having the transferred pattern as a mask; and

further transferring the pattern to the body to be processed by etching using the organic film having the transferred pattern as a mask.

5. A composition for forming an organic film, comprising:

a compound for forming an organic film which has a minimum complex viscosity of 10 Pa·

s or less when the complex viscosity is measured within a range of 50°

C. to 300°

C.;

an organic solvent; and

either or both of a compound shown by the formula (2A) and a compound shown by the formula (3A),

RR₂)_(m3+m4) 

 

(2A)

wherein R represents a single bond, an organic group having 1 to 50 carbon atoms, an ether bond, a —

SO—

group, or a —

SO₂—

group;

R₂ represents a group shown by the formula (2B); and

m3 and m4 represent an integer satisfying 1≤

m3≤

5, 1≤

m4≤

5, and 2≤

m3+m4≤

8,

—

R₂=—

X¹¹—

X′

 

 

(2B)

wherein X¹¹ represents a group shown by the formula (2C); and

X′

represents a group shown by the formula (2D),

6. A composition for forming an organic film, comprising:

a compound for forming an organic film which has a minimum complex viscosity of 10 Pa·

s or less when the complex viscosity is measured within a range of 50°

C. to 300°

C.; and

an organic solvent that is a mixture of one or more organic solvents having a boiling point of lower than 180°

C. and one or more organic solvents having a boiling point of 180°

C. or higher.