IP Library › Granted Patent US 12,572,070
Granted Patent B2
US 12,572,070 · App. 17/401,347 · Granted Mar 10, 2026

Chemical liquid, resist pattern forming method, semiconductor chip manufacturing method, chemical liquid storage body, and chemical liquid manufacturing method

Inventor: Tetsuya Kamimura (Shizuoka, JP)
Assignee: FUJIFILM Corporation
G03F7/0382G03F7/16G03F7/162G03F7/322G03F7/38G03F7/40B82Y40/00
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Quick Facts
Patent No.
US 12,572,070
App. No.
17/401,347
Granted
Mar 10, 2026
Kind
B2
Abstract

The present invention provides a chemical liquid demonstrating excellent defect inhibition performance in a case where the chemical liquid is used as a prewet solution. The present invention also provides a resist pattern forming method, a semiconductor chip manufacturing method, a chemical liquid storage body, and a chemical liquid manufacturing method. The chemical liquid according to an embodiment of the present invention is a chemical liquid to be used as a prewet solution and contains cyclohexanone and one or more kinds of first compounds selected from the group consisting of a compound represented by General Formula (1), a compound represented by General Formula (2), and a compound represented by General Formula (3), in which a content of the cyclohexanone is 98.000% to 99.999% by mass with respect to a total mass of the chemical liquid, and a total content of the first compounds is 0.001 to 100 ppm by mass with respect to the total mass of the chemical liquid.

Claims (78)

1 . A chemical liquid to be used as a prewet solution, comprising:

cyclohexanone; and

one or more kinds of first compounds selected from the group consisting of a compound represented by General Formula (1), a compound represented by General Formula (2), and a compound represented by General Formula (3),

wherein a content of the cyclohexanone is 98.000% to 99.999% by mass with respect to a total mass of the chemical liquid, and

a total content of the first compounds is 0.001 to 100 ppm by mass with respect to the total mass of the chemical liquid

wherein a mass ratio of a content of the compound represented by General Formula (1) to a content of the compound represented by General Formula (2) is 1 to 500, a mass ratio of a content of the compound represented by General Formula (1) to a content of the compound represented by General Formula (3) is 1 to 3,000, and a mass ratio of a content of the compound represented by General Formula (2) to a content of the compound represented by General Formula (3) is 1 to 150, and

wherein the chemical liquid is obtained by subjecting a cyclohexanone raw material to a distillation and purification treatment, wherein the distillation and purification treatment includes performing distillation using a distillation column to obtain a distilled product, and then performing a first filtering of the distilled product by passing through a first filter, a second filter, a third filer, and a fourth filter each made of different materials, and then performing a second filtering by passing through at least a fifth filter and a sixth filter, wherein pore sizes of the fifth filter and the sixth filter are smaller than a pore size of the first filter, the second filter, the third filter, and the fourth filter in the first filtering.

2 . The chemical liquid according to claim 1 ,

wherein a content of the compound represented by General Formula (1) is 0.01 to 70 ppm by mass with respect to the total mass of the chemical liquid.

3 . The chemical liquid according to claim 1 ,

wherein the total content of the first compounds is 0.005 to 95 ppm by mass with respect to the total mass of the chemical liquid.

4 . The chemical liquid according to claim 1 , further comprising:

one or more kinds of hydroxycyclohexanones selected from the group consisting of 2-hydroxycyclohexanone, 3-hydroxycyclohexanone, and 4-hydroxycyclohexanone,

wherein a total content of the hydroxycyclohexanones is 0.001 to 1,000 ppm by mass with respect to the total mass of the chemical liquid.

5 . The chemical liquid according to claim 4 ,

wherein a mass ratio of a content of the 2-hydroxycyclohexanone to a content of the 3-hydroxycyclohexanone is 0.005 to 300.

6 . The chemical liquid according to claim 4 ,

wherein a mass ratio of a content of the 2-hydroxycyclohexanone to a content of the 4-hydroxycyclohexanone is 0.01 to 15.

7 . The chemical liquid according to claim 4 ,

wherein a mass ratio of a content of the 3-hydroxycyclohexanone to a content of the 4-hydroxycyclohexanone is 0.003 to 100.

8 . The chemical liquid according to claim 1 , further comprising:

1,2-cyclohexanedione,

wherein a content of the 1,2-cyclohexanedione is 0.0005 to 40 ppm by mass with respect to the total mass of the chemical liquid.

9 . The chemical liquid according to claim 1 , further comprising:

cyclohexanol,

wherein a content of the cyclohexanol is 0.0003 to 30 ppm by mass with respect to the total mass of the chemical liquid.

10 . The chemical liquid according to claim 1 , further comprising:

1-hexanoic acid,

wherein a content of the 1-hexanoic acid is 5 to 600 ppm by mass with respect to the total mass of the chemical liquid.

11 . The chemical liquid according to claim 1 , comprising:

1,2-cyclohexanedione; and

cyclohexanol,

wherein a mass ratio of a content of the 1,2-cyclohexanedione to a content of the cyclohexanol is 0.2 to 400.

12 . The chemical liquid according to claim 1 , comprising:

1,2-cyclohexanedione; and

1-hexanoic acid,

wherein a mass ratio of a content of the 1,2-cyclohexanedione to a content of the 1-hexanoic acid is 0.005 to 5.

13 . The chemical liquid according to claim 1 , comprising:

cyclohexanol; and

1-hexanoic acid,

wherein a mass ratio of a content of the cyclohexanol to a content of the 1-hexanoic acid is 0.0005 to 0.5.

14 . The chemical liquid according to claim 1 , further comprising:

one or more kinds of second compounds selected from the group consisting of a compound represented by General Formula (4) and a compound represented by General Formula (5),

wherein a total content of the second compounds is 0.5 to 10 ppm by mass with respect to the total mass of the chemical liquid

15 . The chemical liquid according to claim 1 , further comprising:

a high-boiling-point organic compound having a boiling point of 450° C. or higher,

wherein a content of the high-boiling-point organic compound is 10 to 1,000 ppb by mass with respect to the total mass of the chemical liquid.

16 . The chemical liquid according to claim 1 , further comprising:

one or more kinds of metal components selected from the group consisting of a particulate metal component and an ionic metal component,

wherein a total content of the metal components is 10 to 350 ppt by mass with respect to the total mass of the chemical liquid.

17 . The chemical liquid according to claim 16 , comprising:

an Fe-containing particulate metal component having a particle diameter of 15 to 20 nm; and

a Pd-containing particulate metal component having a particle diameter of 15 to 20 nm,

wherein a mass ratio of a content of the Fe-containing particulate metal component having a particle diameter of 15 to 20 nm to a content of the Pd-containing particulate metal component having a particle diameter of 15 to 20 nm is 1 to 23.

18 . The chemical liquid according to claim 1 , which is a prewet solution used by being applied to a substrate to be coated with an actinic ray-sensitive or radiation-sensitive resin composition to form a resist film on the substrate,

wherein the prewet solution is applied before the substrate is coated with the actinic ray-sensitive or radiation-sensitive resin composition.

19 . A resist pattern forming method, comprising:

a prewetting step of coating the substrate with the chemical liquid according to claim 18 ;

a step of forming a resist film by coating the substrate having undergone the prewetting step with the actinic ray-sensitive or radiation-sensitive resin composition;

a step of exposing the resist film; and

a step of obtaining a resist pattern by developing the exposed resist film with a developer.

20 . A semiconductor chip manufacturing method, comprising:

the resist pattern forming method according to claim 19 .

21 . A chemical liquid storage body comprising:

a container; and

the chemical liquid according to claim 1 that is stored in the container,

wherein a liquid contact portion coming into contact with the chemical liquid in the container is formed of electropolished stainless steel or a fluororesin.

22 . The chemical liquid storage body according to claim 21 ,

wherein a void volume in the container determined by Equation (1) is 1% to 20% by volume,

void volume={1−(volume of the chemical liquid in the container/volume of the container)}×100.  Equation (1)

23 . A chemical liquid to be used as a prewet solution, comprising:

cyclohexanone;

one or more kinds of first compounds selected from the group consisting of a compound represented by General Formula (1), a compound represented by General Formula (2), and a compound represented by General Formula (3); and

one or more kinds of second compounds selected from the group consisting of a compound represented by General Formula (4) and a compound represented by General Formula (5),

wherein a content of the cyclohexanone is 98.000% to 99.999% by mass with respect to a total mass of the chemical liquid,

a total content of the first compounds is 0.001 to 100 ppm by mass with respect to the total mass of the chemical liquid, and

a total content of the second compounds is 0.5 to 10 ppm by mass with respect to the total mass of the chemical liquid

wherein the chemical liquid is obtained by subjecting a cyclohexanone raw material to a distillation and purification treatment, wherein the distillation and purification treatment includes performing distillation using a distillation column to obtain a distilled product, and then performing a first filtering of the distilled product by passing through a first filter, a second filter, a third filer, and a fourth filter each made of different materials, and then performing a second filtering by passing through at least a fifth filter and a sixth filter, wherein pore sizes of the fifth filter and the sixth filter are smaller than a pore size of the first filter, the second filter, the third filter, and the fourth filter in the first filtering.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2021
From: KAMIMURA, TETSUYA
To: FUJIFILM CORPORATION
Reel/Frame 057181/0276 →
Priority Claims (1)
JP 2019-029633 · Feb 21, 2019 · national
Continuity (2)
Continuation PCTJP2020003178 · Jan 29, 2020
Related Publication 20210373439A1 · Dec 2, 2021
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