IP Library Granted Patent US 9,411,231
Granted Patent B2
US 9,411,231 · App. 14/350,691 · Granted Aug 9, 2016

Silane composition and cured film thereof, and method for forming negative resist pattern using same

Inventors: Tsuyoshi Ogawa (Saitama, JP); Junya Nakatsuji (Fujimino, JP); Kazuhiro Yamanaka (Tachikawa, JP)
Assignee: Central Glass Company, Limited
G03F7/0757C08L83/04C08L83/12C09D5/00C09D183/04C09D183/06G03F7/168H01L21/02126C08G77/46C08G77/80
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Quick Facts
Patent No.
US 9,411,231
App. No.
14/350,691
Granted
Aug 9, 2016
Kind
B2
Abstract

A composition provided to contain: an alkoxysilane condensate obtained by the condensation of alkoxysilane A represented by general formula (1): (CH 3 )Si(OR 1 ) 3 (In the general formula (1), R 1 mutually independently represents methyl group or ethyl group.), alkoxysilane B represented by general formula (2): (Ph)Si(OR 1 ) 3 (In the general formula (2), R 1 mutually independently represents methyl group or ethyl group.), and alkoxysilane C represented by general formula (3): (CH 3 ) 2 Si(OR 1 ) 2 (In the general formula (3), R 1 mutually independently represents methyl group or ethyl group.) at an A:B:C mole ratio within the range of 30-70:10-50:20-60; and a polyether-modified polydimethylsiloxane.

Claims (33)

1. A composition comprising:

1) an alkoxysilane condensate obtained by the condensation of

i) alkoxysilane A represented by general formula (1): (CH 3 )Si(OR 1 ) 3 ,

ii) alkoxysilane B represented by general formula (2): (Ph)Si(OR 1 ) 3 , and

iii) alkoxysilane C represented by general formula (3): (CH 3 ) 2 Si(OR 1 ) 2 at an A:B:C mole ratio within the range of 30-70:10-50:20-60, and wherein R 1 mutually independently represents a methyl group or an ethyl group;

2) a polyether-modified polydimethylsiloxane; and

3) a photoacid generator.

2. A composition as claimed in claim 1 , wherein the polyether-modified polydimethylsiloxane is a compound represented by general formula (4):

wherein R 2 mutually independently represents a hydrogen atom or a methyl group, R 3 mutually independently represents a C 1 -C 20 alkyl group or a C 6 -C 10 aryl group, “m” represents an integer of 1-30, “n” represents an integer of 1-30, “X” represents an integer of 1-50, and “Y” represents an integer of 1-50, and wherein the content of the polyether-modified polydimethylsiloxane is not lower than 0.001 mass % and not higher than 5 mass % relative to the condensate.

3. A composition as claimed in claim 1 , wherein the content of the photoacid generator is not lower than 0.01 mass % and not higher than 5 mass % relative to the condensate.

4. A method for producing a cured film comprising the steps of:

(1) adding an organic solvent to a composition as claimed in claim 1 to produce an application liquid;

(2) applying the application liquid onto a substrate to form a film; and

(3) heating and baking the substrate,

wherein the cured film has a thickness of at least 3.0 μm and a pencil hardness of at least 5H.

5. A method for producing a composition as claimed in claim 1 , comprising the steps of:

1) adding water, a water-soluble organic solvent E and an acid catalyst to an alkoxysilane mixture D of before the condensation of

i) alkoxysilane A represented by general formula (1): (CH 3 )Si(OR 1 ) 3 ,

ii) alkoxysilane B represented by general formula (2): (Ph)Si(OR 1 ) 3 , and

iii) alkoxysilane C represented by general formula (3): (CH 3 ) 2 Si(OR 1 ) 2 at an A:B:C mole ratio within the range of 30-70:10-50:20-60, wherein R 1 mutually independently represents a methyl group or an ethyl group, thereby producing a mixed substance of before condensation;

2) hydrolyzing and condensing the mixed substance of before condensation thereby providing a reaction system with a condensate;

3) extracting the condensate with a water-insoluble organic solvent F while extracting the acid catalyst with water;

4) removing the organic solvent F;

5) adding a polyether-modified polydimethylsiloxane; and

6) adding a photoacid generator.

6. A method for producing a composition, as claimed in claim 5 , wherein water is used in an amount of 1.5-5 times larger than that of alkoxy groups that the alkoxysilane mixture D has, in mole ratio.

7. A method for producing a composition, as claimed in claim 5 , wherein the organic solvent E comprises alcohol.

8. A method for producing a composition, as claimed in claim 5 , wherein the acid catalyst comprises acetic acid.

9. A method for forming a negative pattern, comprising the steps of:

(1) applying a composition as claimed in claim 1 onto a substrate to form a film,

(2) irradiating the film with high-energy beams to generate acid at an irradiated portion to accelerate a further condensation of the condensate at the irradiated portion thereby making the film insoluble in an alkali developing solution; and

(3) removing a non-irradiated portion of the film by using the alkali developing solution thereby forming a negative pattern.

10. A method for forming a negative pattern, as claimed in claim 9 , wherein the high-energy beams used for the irradiation comprises electromagnetic waves or electron beams of a wavelength of not larger than 400 nm.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2014
From: OGAWA, TSUYOSHI; NAKATSUJI, JUNYA; YAMANAKA, KAZUHIRO
To: CENTRAL GLASS COMPANY, LIMITED
Reel/Frame 032637/0017 →
Priority Claims (2)
JP 2011-224930 · Oct 12, 2011 · national
JP 2012-222769 · Oct 5, 2012 · national
Continuity (1)
Related Publication 20140242516A1 · Aug 28, 2014