Resist underlayer composition and method of manufacturing semiconductor integrated circuit device using the same

• US 9,291,899 B2
• Filed: 12/30/2009
• Issued: 03/22/2016
• Est. Priority Date: 12/30/2008
• Status: Active Grant

• Current Assignee: Cheil Industries Incorporated
• Original Assignee: Cheil Industries Incorporated
• Inventors: Cho, Hyeon-Mo, Kim, Sang-Kyun, Woo, Chang-Soo, Kim, Mi-Young, Koh, Sang-Ran, Yun, Hui-Chan, Lee, Woo-Jin, Kim, Jong-Seob
• Primary Examiner(s): LEE, SIN J
• Application Number:
  US12/654,737
• Publication Number:
  US 20100167203A1
• Time in Patent Office: 2,274 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/16 to hydroxyl groups
• CPC Class Codes: C08G 77/18 to alkoxy or aryloxy groups
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/24 halogen-containing groups
• CPC Class Codes: C08G 77/26 nitrogen-containing groups
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: C08G 77/52 containing aromatic rings
• CPC Class Codes: C08G 77/70 Siloxanes defined by use of the MDTQ nomenclature
• CPC Class Codes: C08K 5/0008 Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08L83/10 takes precedence
• CPC Class Codes: C09D 183/04 Polysiloxanes
• CPC Class Codes: C09D 183/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C09D183/10 takes precedence
• CPC Class Codes: G03F 7/0752 in non photosensitive layers or as additives, e.g. for dry lithography
• CPC Class Codes: G03F 7/0757 Macromolecular compounds containing Si-O, Si-C or Si-N bonds G03F7/0752 takes precedence
• CPC Class Codes: G03F 7/09 characterised by structural details, e.g. supports, auxiliary layers supports for printing plates in general B41N
• 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 7/11 : having cover layers or intermediate layers, e.g. subbing layers G03F7/091 - G03F7/093, B41N3/03 take precedence
• CPC Class Codes: G03F 7/30 : Imagewise removal using liquid means
• CPC Class Codes: G03F 7/36 : Imagewise removal not covered by groups G03F7/30 - G03F7/34, e.g. using gas streams, using plasma

Abstract

A resist underlayer composition and a method of manufacturing a semiconductor integrated circuit device, the composition including a solvent and an organosilane polymer, the organosilane polymer being a condensation polymerization product of at least one first compound represented by Chemical Formulae 1 and 2 and at least one second compound represented by Chemical Formulae 3 to 5.

Claims

1. A resist underlayer composition, comprising:

a solvent;

a cross-linking catalyst, the cross-linking catalyst including at least one of pyridinium p-toluenesulfonate, amidosulfobetain-16, ammonium(-)-camphor-10-sulfonic acid ammonium salt, ammonium formate, alkyltriethylammonium formate, pyridinium formate, tetrabutyl ammonium acetate, tetrabutyl ammonium azide, tetrabutyl ammonium benzoate, tetrabutyl ammonium bisulfate, tetrabutyl ammonium bromide, tetrabutyl ammonium chloride, tetrabutyl ammonium cyanide, tetrabutyl ammonium fluoride, tetrabutyl ammonium iodide, tetrabutyl ammonium sulfate, tetrabutyl ammonium nitrate, tetrabutyl ammonium nitrite, tetrabutyl ammonium p-toluene sulfonate, and tetrabutyl ammonium phosphate; and

an organosilane polymer, the organosilane polymer being a condensation polymerization product of;

at least one first compound represented by Chemical Formula 1 or 2, and

at least one second compound represented by any one of Chemical Formulae 3 to 5

wherein the at least one first compound represented by Chemical Formula 1 or 2 includes at least one compound represented by Chemical Formula 1, and the at least one second compound represented by any one of Chemical Formulae 3 to 5 includes at least one compound represented by Chemical Formula 3, at least one compound represented by Chemical Formula 4, and at least one compound represented by Chemical Formula 5;

[R¹]₃Si-[Ph¹]₁-Si[R²]₃ 

 

[Chemical Formula 1]

[R¹]₃Si-[Ph¹]_m-Ph² 

 

[Chemical Formula 2]

[R¹]₃Si—

(CH₂)_n—

R³ 

 

[Chemical Formula 3]

[R¹]₃Si—

R⁴ 

 

[Chemical Formula 4]

[R¹]₃Si—

X—

Si[R²]₃ 

 

[Chemical Formula 5]

wherein, in Chemical Formulae 1 to 5;

Ph¹ is a substituted or unsubstituted phenylene group,

Ph² is a substituted or unsubstituted phenyl group,

R¹ and R² are each independently a halogen, a hydroxyl group, an alkoxy group, a carboxyl group, an ester group, a cyano group, a haloalkylsulfite group, an alkylamine group, an alkylsilylamine group, or an alkylsilyloxy group,

R³ is a substituted or unsubstituted C6 to C12 aryl group,

R⁴ is hydrogen or a C1 to C6 alkyl group,

X is a substituted or unsubstituted linear alkylene group, a substituted or unsubstituted branched alkylene group, or an alkylene group including an alkenylene group, an alkynylene group, a heterocyclic group, a urea group, or an isocyanurate group in its main chain,

l is an integer of 2 to 4, and m is an integer of 1 to 4, and

n is an integer of 0 to 5.

2. The resist underlayer composition as claimed in claim 1, wherein the organosilane polymer is produced by a condensation polymerization reaction of about 1 to about 99 mol % of the at least one first compound, and about 1 to about 99 mol % of the at least one second compound, under an acid catalyst or a base catalyst.

3. The resist underlayer composition as claimed in claim 1, wherein the organosilane polymer has a weight average molecular weight of about 2,000 to about 50,000.

4. The resist underlayer composition as claimed in claim 1, wherein the organosilane polymer is included in an amount of about 0.1 to about 50 wt %, based on a total weight of the resist underlayer composition.

5. The resist underlayer composition as claimed in claim 1, further comprising at least one of a cross-linking agent, a radical stabilizer, and a surfactant.

6. The resist underlayer composition as claimed in claim 1, wherein:

the at least one first compound includes bis(triethoxysilyl)biphenyl, and

the at least one second compound includes bis(triethoxysilyl)ethane, phenyltrimethoxysilane, and methyltrimethoxysilane.

7. A method of manufacturing semiconductor integrated circuit device, the method comprising:

providing a material layer on a substrate;

forming a first resist underlayer on the material layer;

coating the resist underlayer composition as claimed in claim 1 on the first resist underlayer to form a second resist underlayer on the first resist underlayer;

forming a radiation-sensitive imaging layer on the second resist underlayer;

patternwise exposing the radiation-sensitive imaging layer to radiation to form a pattern of radiation-exposed regions in the imaging layer;

selectively removing portions of the radiation-sensitive imaging layer and the second resist underlayer to expose portions of the first resist underlayer;

selectively removing the patterned second resist underlayer and portions of the first resist underlayer to expose portions of the material layer; and

etching the exposed portions of the material layer to pattern the material layer.

8. The method as claimed in claim 7, further comprising forming an anti-reflection coating after forming the second resist underlayer and prior to forming a radiation-sensitive imaging layer.

9. The method as claimed in claim 7, wherein the second resist underlayer includes an organosilane polymer including a repeating unit represented by Chemical Formula 6:

(SiO_1.5-[Ph¹]₁-SiO_1.5)_a(Ph²-[Ph¹]_m-SiO_1.5)_b(R³—

(CH₂)_n—

SiO_1.5)_c(R⁴—

SiO_1.5)_d(SiO_1.5—

X—

SiO_1.5)_e 

 

[Chemical Formula 6]

wherein, in Chemical Formula 6;

Ph¹ is a substituted or unsubstituted phenylene group,

Ph² is a substituted or unsubstituted phenyl group,

R³ is a substituted or unsubstituted C6 to C12 aryl group,

R⁴ is hydrogen or a C1 to C6 alkyl group,

X is a substituted or unsubstituted linear alkylene group, a substituted or unsubstituted branched alkylene group, or an alkylene group including an alkenylene group, an alkynylene group, a heterocyclic group, an urea group, or an isocyanurate group in its main chain,

l is an integer of 2 to 4, and m is an integer of 1 to 4,

n is an integer of 0 to 5, and

a, b, c, d, and e satisfy the relations;

0<

a≦

0.99, 0≦

b≦

0.99, 0.01≦

a+b≦

0.99, 0<

c≦

0.99, 0<

d≦

0.99, 0<

e≦

0.99, 0.01≦

c+d+e≦

0.99, and a+b+c+d+e=1.

10. A resist underlayer composition, comprising:

a solvent;

a cross-linking catalyst, the cross-linking catalyst including at least one of pyridinium p-toluenesulfonate, amidosulfobetain-16, ammonium(-)-camphor-10-sulfonic acid ammonium salt, ammonium formate, alkyltriethylammonium formate, pyridinium formate, tetrabutyl ammonium acetate, tetrabutyl ammonium azide, tetrabutyl ammonium benzoate, tetrabutyl ammonium bisulfate, tetrabutyl ammonium bromide, tetrabutyl ammonium chloride, tetrabutyl ammonium cyanide, tetrabutyl ammonium fluoride, tetrabutyl ammonium iodide, tetrabutyl ammonium sulfate, tetrabutyl ammonium nitrate, tetrabutyl ammonium nitrite, tetrabutyl ammonium p-toluene sulfonate, and tetrabutyl ammonium phosphate; and

an organosilane polymer, the organosilane polymer including a repeating unit represented by Chemical Formula 6;

(SiO_1.5-[Ph¹]₁-SiO_1.5)_a(Ph²-[Ph¹]_m-SiO_1.5)_b(R³—

(CH₂)_n—

SiO_1.5)_c(R⁴—

SiO_1.5)_d(SiO_1.5—

X—

SiO_1.5)_e 

 

[Chemical Formula 6]

wherein, in Chemical Formula 6;

Ph¹ is a substituted or unsubstituted phenylene group,

Ph² is a substituted or unsubstituted phenyl group,

R³ is a substituted or unsubstituted C6 to C12 aryl group,

R⁴ is hydrogen or a C1 to C6 alkyl group,

X is a substituted or unsubstituted linear alkylene group, a substituted or unsubstituted branched alkylene group, or an alkylene group including an alkenylene group, an alkynylene group, a heterocyclic group, a urea group, or an isocyanurate group in its main chain,

l is an integer of 2 to 4, and m is an integer of 1 to 4,

n is an integer of 0 to 5, and

a, b, c, d, and e satisfy the relations;

0<

a≦

0.99, 0≦

b≦

0.99, 0.01≦

a+b≦

0.99, 0<

c≦

0.99, 0<

d≦

0.99, 0<

e≦

0.99, 0.01≦

c+d+e≦

0.99, and a+b+c+d+e=1.

11. A resist underlayer, comprising:

an organosilane polymer including a repeating unit represented by Chemical Formula 6;

(SiO_1.5-[Ph¹]₁-SiO_1.5)_a(Ph²-[Ph¹]_m-SiO_1.5)_b(R³—

(CH₂)_n—

SiO_1.5)_c(R⁴—

SiO_1.5)_d(SiO_1.5—

X—

SiO_1.5)_e 

 

[Chemical Formula 6]

wherein, in Chemical Formula 6;

Ph¹ is a substituted or unsubstituted phenylene group,

Ph² is a substituted or unsubstituted phenyl group,

R³ is a substituted or unsubstituted C6 to C12 aryl group,

R⁴ is hydrogen or a C1 to C6 alkyl group,

X is a substituted or unsubstituted linear alkylene group, a substituted or unsubstituted branched alkylene group, or an alkylene group including an alkenylene group, an alkynylene group, a heterocyclic group, a urea group, or an isocyanurate group in its main chain,

l is an integer of 2 to 4, and m is an integer of 1 to 4,

n is an integer of 0 to 5, and

a, b, c, d, and e satisfy the relations;

0<

a≦

0.99, 0≦

b≦

0.99, 0.01≦

a+b≦

0.99, 0<

c≦

0.99, 0<

d≦

0.99, 0<

e≦

0.99, 0.01≦

c+d+e≦

0.99, and a+b+c+d+e=1.

12. The resist underlayer as claimed in claim 11, wherein the resist underlayer has an absorbance of greater than about 0.15 and a refractive index of less than about 1.70 under a wavelength condition of about 193 nm.

13. A resist underlayer composition, comprising:

a solvent;

a cross-linking catalyst; and

an organosilane polymer, the organosilane polymer being a condensation polymerization product of bis(triethoxysilyl)biphenyl, phenyltrimethoxysilane, and methyltrimethoxysilane.