Composition comprising a primary and a secondary surfactant, for cleaning or rinsing a product

Patent metadata

Field	Value
Publication number	US-12084628-B2
Application number	US-201816762275-A
Country	US
Kind code	B2
Filing date	Nov 26, 2018
Priority date	Nov 28, 2017
Publication date	Sep 10, 2024
Grant date	Sep 10, 2024

Abstract

Described is a composition comprising as primary surfactant an ionic compound comprising one or more fluoroalkyl groups and as secondary surfactant at least one non-ionic compound comprising one or more polyalkyloxy and/or polyalkylenoxy groups, for cleaning or rinsing a product, preferably a product used in the semiconductor industry, and a respective use of said composition. Further described is a method of making a cleaned or rinsed product, preferably a product used in the semiconductor industry, comprising a substrate and supported thereon a patterned material layer having line-space structures with a line width of 50 nm or below, comprising the step of cleaning or rinsing said product with the composition of the invention.

First claim

The invention claimed is:

1. A composition for cleaning or rinsing a product, comprising:
a primary surfactant comprising an ionic compound of formula (I),

wherein:
X is a cation,
one of Y1 and Y2 is an anionic polar group and the other is hydrogen, and
each group of Z1, Z2 and Z3 is, independent of each other,
a branched or unbranched C 1-10 -alkyl group
or
a group of the structure R i —{A[C(R 1 )(R 2 )—] c [—C(R 3 )(R 4 )—] d } e —, wherein:

R 1 , R 2 , R 3 and R 4 are, independent of each other, hydrogen or a branched or unbranched C 1-4 -alkyl group,
R i is a branched or unbranched C 1-10 -fluoroalkyl group,
A is oxygen, sulfur and/or —N(H)—,
c is an integer in the range of from 0 to 10,
d is an integer in the range of from 0 to 10,
e is an integer in the range of from 1 to 5,
c and d are not both 0, and
at least one of the groups Z1, Z2 or Z3 is a group of the structure R i —{A[—C(R 1 )(R 2 )—] c [—C(R 3 )(R 4 )—] d } e —; and
a secondary surfactant comprising at least one non-ionic compound comprising one or more polyalkyloxy and/or polyalkylenoxy groups selected from the group consisting of
a compound of formula (II) selected from the group consisting of
a compound of formula (IIa):

and
a compound of formula (IIb):

wherein
R 6 is a branched or unbranched C 2-6 -alkylen group,
R 18 is hydrogen or a branched or unbranched C 1-4 -alkyl group, and
l is an integer in the range of from 5 to 30;

a compound of formula (IV),

wherein
R 17 is a branched or unbranched C 2-6 -alkylen group, and
o is an integer in the range of from 5 to 30;

a compound of formula (V),

wherein
R 8 , R 13 and R 14 are each independent of each other, hydrogen or methyl,
R 9 , R 11 and R 12 are each independent of each other a branched or unbranched C 2-6 -alkylen group,
R 10 is a branched or unbranched C 1-4 -alkyl group, and
p, q and r are each independent of each other an integer in the range of from 2 to 25; and

a compound of formula (VI),
(H 3 C) 3 Si—O—R 15 —O—Si(CH 3 ) 3   (VI),

wherein
R 15 consists of
a number in the range of from 1 to 100 of repeating units of formula (VII):
—[Si(CH 3 ) 2 —O]—  (VII),

and
a number in the range of from 1 to 100 of repeating units of formula (VIII):
—[Si(CH 3 )(R 16 )—O]—  (VIII),

wherein R 16 is a group comprising one or more ethylene glycol groups and/or one or more propylene glycol groups, and
wherein the repeating units of formula (VII) and the repeating units of formula (VIII) are arranged randomly or in random alternating blocks, each block comprising two or more repeating units of formula (VII) or of formula (VIII) per block.

2. The composition according to claim 1 ,
wherein each group Z1, Z2 and Z3 is independent of each other a group of the structure R i -{A[-C(R 1 )(R 2 )—] c [—C(R 3 )(R 4 )—] d } e —, and/or
wherein at least one non-ionic compound is a compound of formula (II).

3. The composition according to claim 1 , wherein in the ionic compound of formula (I),
X is a monovalent cation not comprising a metal, selected from the group consisting of a proton and a group NR 4 + ,
wherein each R is independently selected from the group consisting of H, a branched C 1-6 -alkyl group, and an unbranched C 1-4 -alkyl group;
one of Y1 and Y2 is an anionic polar group selected from the group consisting of COO − , SO 3 − , —(O)SO 3 − , —PO 3 2− and —(O)PO 3 2− , and the other is hydrogen; and
each group Z1, Z2 and Z3 is, independent of each other, a group of the structure R i -{A[C(R 1 )(R 2 )] c [C(R 3 )(R 4 )] d } e —.

4. The composition according to claim 1 , wherein in the compound of formula (I)
X is selected from the group consisting of a proton and a group NR 4 + , wherein each R is independently selected from the group consisting of a H, a branched C 1-6 -alkyl group, and an unbranched C 1-4 -alkyl group,
one of Y1 and Y2 is —SO3 − , and the other is hydrogen,
each group Z1, Z2 and Z3 is, independent of each other, a group of the structure F 3 C(CF 2 ) a (CH 2 ) b {O[—C(R 1 )(R 2 )—] c [C(R 3 )(R 4 )—] d } e —, wherein:
a is an integer in the range of from 0 to 2, and
b is an integer in the range of from 1 to 6.

5. The composition of claim 1 , further comprising water.

6. The composition of claim 1 ,
wherein a mass ratio of the compound of formula (I) to the compound of formula (II) is in the range of from 1:4 to 1:1, and/or
wherein a sum of the total amount of compound of formula (I) and the total amount of compound of formula (II) present in the composition is in the range of from 0.01 wt.-% to 0.5 wt.-%, based on the total weight of the composition.

7. The composition according to claim 1 ,
wherein an equilibrium surface tension of the composition is less than 35 mN/m, as measured at 25° C. according to DIN 53914:1997-07 with a Kruess Tensiometer K 100 by the plate method, and/or
wherein a pH of the composition is in a range of from 4.0 to 11.0.

8. A method of using the composition of claim 1 , comprising:
cleaning or rinsing a product by contacting the product with the composition,
wherein the product comprises a substrate supporting a patterned material, the patterned material having line-space structures with a line width of 50 nm or below.

9. The method according to claim 8 ,
wherein the cleaning or rinsing is part of a process of making integrated circuit devices, optical devices, micromachines, or mechanical precision devices, and/or
wherein the substrate is a semiconductor substrate.

10. The method according to claim 8 , wherein the composition is used for cleaning or rinsing so that
a pattern collapse is prevented or reduced,
a line edge roughness is reduced,
watermark defects are prevented or removed,
a photoresist-swelling is prevented or reduced,
blob defects are prevented or reduced, and/or
particles are removed.

11. The method according to claim 8 , wherein:
the patterned material is at least one selected from the group consisting of a patterned developed photoresist layer, a patterned barrier material layer, a patterned multi-stack material layer, and a patterned dielectric material layer;
the patterned material has photoresist structures having an aspect ratio greater than 2 and/or patterned multi-stack line/space structures having an aspect ratio greater than 2; and/or
the line-space structures have a line width of 32 nm or below.

12. A method of making a cleaned or rinsed product, the method comprising:
preparing or providing a product comprising a substrate supporting a patterned material layer, the patterned material layer having line-space structures with a line width of 50 nm or below;
preparing or providing a composition as defined in claim 1 ; and
cleaning or rinsing the product with the composition to produce a cleaned or rinsed product.

13. The method according to claim 12 , further comprising:
providing a photoresist layer on a substrate, wherein the photoresist layer is an immersion photoresist layer, an

Assignees

• Basf Se

Inventors

• Chou I Chen
• Klipp Andreas
• Ferstl Berthold

Classifications

• H10P70/20

  Cleaning during device manufacture · CPC title

• H10P70/00

  Cleaning of wafers, substrates or parts of devices · CPC title

• C11D1/006

  Surface-active compounds containing fluorine and phosphorus · CPC title

• C11D3/245

  containing fluorine · CPC title

• C11D1/66

  Non-ionic compounds {(C11D1/002, C11D1/004, C11D1/008 take precedence)} · CPC title