US2001043992A1PendingUtilityA1
Organic polymer for anti-reflective coating layer and preparation thereof
Priority: Dec 30, 1999Filed: Dec 27, 2000Published: Nov 22, 2001
Est. expiryDec 30, 2019(expired)· nominal 20-yr term from priority
C08F 220/1818C08F 220/281C07C 69/54C07C 2603/24C08F 220/14C07C 69/017
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Claims
Abstract
The present invention provides a polymer that can be used as an anti-refelctive coating (ARC) polymer, an ARC composition comprising the same, methods for producing the same, and methods for using the same. The polymer of the present invention is particularly useful in a submicrolithographic process, for example, using KrF (248 nm) or ArF (193 nm) lasers as a light source. The polymer of the present invention comprises a chromophore that is capable of absorbing light at the wavelengths used in a submicrolithographic process. Thus, the ARC of the present invention significantly reduces or prevents back reflection of light and the problem of the CD alteration caused by the diffracted and/or reflected light. The ARC of the present invention also significantly reduces or eliminates the standing wave effect and reflective notching. Therefore, the polymer of the present invention can be used to produce a stable ultrafine pattern that is suitable in manufacturing of 64M, 256M, 1G, 4G and 16G DRAM semiconductor devices. Moreover, the ARC of the present invention significantly improves the production yield of such semiconductor devices.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound of the Formula:
wherein
R 1 is alkylene; and
R 2 is hydrogen or alkyl.
2 . The compound of claim 1 , wherein R 1 is methylene.
3 . The compound of claim 1 , wherein R 2 is hydrogen or methyl.
4 . A method for preparing a 9-anthracenealkyl acrylate compound of the formula:
said method comprising the steps of contacting 9-anthracene alkyl alcohol of the formula:
with an activated acryloyl compound of the formula:
under conditions sufficient to produce said 9-anthracenealkyl acrylate compound, wherein
X is a carbonyl activating group;
R 1 is alkylene; and
R 2 is hydrogen or alkyl.
5 . The method of claim 4 , wherein R 1 is methylene, R 2 is hydrogen or methyl, and X is halide.
6 . A polymer of the formula:
wherein
each of R 1 and R 3 is independently C 1 -C 5 alkylene;
each of R 2 and R 4 is independent hydrogen or alkyl; and
x and y are mole fractions, each of which is in the range from 0.01 to 0.99.
7 . The polymer of claim 6 , wherein R 1 is methylene; R 2 and R 4 are hydrogen; R 3 is ethylene, propylene, or butylene; and each of x and y is 0.5.
8 . The polymer of claim 6 , wherein R 1 is methylene; R 2 is methyl; R 4 is hydrogen; R 3 is ethylene, propylene, or butylene; and each of x and y is 0.5.
9 . A method for producing a polymer of the formula:
said method comprising the steps of polymerizing a mixture of monomers under conditions sufficient to produce said polymer, wherein said mixture of monomers comprises:
9-anthracenealkylacrylate compound of the formula:
and
a hydroxyalkylacrylate compound of the formula:
wherein
each of R 1 and R 3 is independently C 1 -C 5 alkylene;
each of R 2 and R 4 is independent hydrogen or alkyl; and
x and y are mole fractions, each of which is in the range from 0.01 to 0.99.
10 . The method of claim 9 , wherein said mixture of monomers further comprises a polymerization initiator.
11 . The method of claim 10 , wherein said polymerization initiator is selected from the group consisting of 2,2-azobisisobutyronitrile, acetylperoxide, laurylperoxide, and t-butylperoxide.
12 . The method of claim 9 , wherein said mixture of monomers further comprises a solvent.
13 . The method of claim 12 , wherein said solvent is selected from the group consisting of tetrahydrofuran, toluene, benzene, methylethyl ketone and dioxane.
14 . The method of claim 9 further comprising the steps of heating said mixture of monomers to temperature in the range of from about 50° C. to about 90° C.
15 . A polymer of the formula:
wherein
R 1 is alkylene;
each of R 2 , R 4 and R 6 is independently hydrogen or alkyl;
R 3 is C 1 -C 5 alkylene;
R 5 is alkyl; and
x, y and z are mole fractions, each of which is in the range of from about 0.01 to about 0.99.
16 . The polymer of claim 15 , wherein R 2 and R 4 are hydrogen; R 5 and R 6 are methyl; R 3 is ethylene, propylene, or butylene; R 1 is methylene; and the ratio of x, y and z is 0.3:0.5:0.2.
17 . The polymer of claim 15 , wherein R 1 is methylene; R 2 , R 4 and R 5 are methyl; R 6 is hydrogen; R 3 is ethylene, propylene, or butylene; and the ratio of x, y and z is 0.3:0.5:0.2.
18 . A method for producing a polymer of the formula:
said method comprising the steps of polymerizing a mixture of monomers under conditions sufficient to produce said polymer, wherein said mixture of monomers comprises:
9-anthracenealkylacrylate compound of the formula:
a hydroxyalkylacrylate compound of the formula:
an alkyl acrylate compound of the formula:
wherein
R 1 is alkylene;
each of R 2 , R 4 and R 6 is independently hydrogen or alkyl;
R 3 is C 1 -C 5 alkylene;
R 5 is alkyl; and
x, y and z are mole fractions, each of which is in the range of from about 0.01 to about 0.99.
19 . The method of claim 18 , wherein said mixture of monomers further comprises a polymerization initiator.
20 . The method of claim 19 , wherein said initiator is selected from the group consisting of 2,2-azobisisobutyronitrile, acetylperoxide, laurylperoxide, and t-butylperoxide.
21 . The method of claim 18 , wherein said mixture of monomers further comprises a solvent.
22 . The method of claim 21 , wherein said solvent is selected from the group consisting of tetrahydrofuran, toluene, benzene, methylethyl ketone and dioxane.
23 . The method of claim 18 further comprising the steps of heating said mixture of monomers to temperature in the range of from about 50° C. to about 90° C.
24 . A poly[acroleinalkylacetal] polymer of the formula:
wherein
R 7 is hydrogen or alkyl; and
R 8 is alkyl.
25 . The poly[acroleinalkylacetal] polymer of claim 24 , wherein R 7 is hydrogen or methyl; and R 8 is methyl.
26 . A method for preparing a poly(acroleinalkylacetal) of the formula:
said method comprising the steps of polymerizing a monomer of the formula:
under conditions sufficient to produce a poly(acrolein) polymer of the formula:
contacting said poly(acrolein) polymer with an alcohol of the formula R 8 OH under conditions sufficient to produce said poly(acroleinalkylacetal), wherein
R 7 is hydrogen or alkyl; and
R 8 is alkyl.
27 . The method of claim 26 , wherein said polymerization step further comprises adding a polymerization initiator to said monomer.
28 . The method of claim 27 , wherein said initiator is selected from the group consisting of 2,2-azobisisobutyronitrile, acetylperoxide, laurylperoxide, and t-butylperoxide.
29 . The method of claim 26 , wherein said monomer is dissolved in a solvent.
30 . The method of claim 29 , wherein said solvent is selected from the group consisting of tetrahydrofuran, toluene, benzene, methylethyl ketone and dioxane.
31 . The method of claim 26 , wherein said polymerization step comprises heating said monomer to temperature in the range of from about 50° C. to about 90° C.
32 . The method of claim 26 , wherein said poly(acroleinalkylacetal) is precipitated in ethyl ether.
33 . An anti-reflective coating composition suitable for use in fabrication of semiconductor devices, comprising a polymer of the formula:
wherein
each of R 1 and R 3 is independently C 1 -C 5 alkylene;
each of R 2 , R 4 and R 6 is independently hydrogen or alkyl;
R 5 is alkyl; and
x, y and z are mole fractions, each of which is in the range of from about 0.01 to about 0.99.
34 . The anti-reflective coating composition of claim 33 , further comprising an additive selected from the group consisting of anthracene, 9-anthracenemethanol, 9-anthracenecarbonitrile, 9-anthracenecarboxylic acid, dithranol, 1,2,10-anthracenetriol, anthraflavonic acid, 9-anthraldehydeoxime, 9-anthraldehyde, 2-amino-7-methyl-5-oxo-5H-[1]benzopyrono [2,3-b]pyridine-3-carbonitrile, 1-aminoanthraquinone, anthraquinone-2-carboxylic acid, 1,5-dihydroxyanthraquinone, anthrone, 9-anthryltrifluoromethyl ketone, 9-alkylanthracene derivative of the formula:
9-carboxylanthracene derivative of the formula:
1-carboxylanthracene derivative of the formula 6:
and mixtures thereof,
wherein
each of R a , R b , and R c is independently hydrogen, hydroxy, hydroxyalkyl, optionally substituted C 1 -C 5 alkyl, or alkoxyalkyl.
35 . The anti-reflective coating composition of claim 33 , further comprising a poly[acroleinalkylacetal] polymer of the formula:
wherein
R 7 is hydrogen or alkyl; and
R 8 is alkyl.
36 . A method for producing an anti-reflective polymer coated substrate comprising the steps of:
(a) coating an anti-reflective coating composition on a substrate, wherein said anti-reflective coating composition comprises an anti-reflective coating polymer of the formula: wherein
each of R 1 and R 3 is independently C 1 -C 5 alkylene;
each of R 2 , R 4 and R 6 is independently hydrogen or alkyl;
R 5 is alkyl; and
x, y and z are mole fractions, each of which is in the range of from about 0.01 to about 0.99; and
(b) curing said anti-reflective coating polymer to produce said anti-reflective coating coated substrate.
37 . The method of claim 36 , wherein said anti-reflective coating composition further comprises a poly[acroleinalkylacetal] polymer of the formula:
wherein
R 7 is hydrogen or alkyl; and
R 8 is alkyl.
38 . The method of claim 36 , wherein said anti-reflective coating composition further comprises an additive selected from the group consisting of anthracene, 9-anthracenemethanol, 9-anthracenecarbonitrile, 9-anthracenecarboxylic acid, dithranol, 1,2,10-anthracenetriol, anthraflavonic acid, 9-anthraldehydeoxime, 9-anthraldehyde, 2-amino-7-methyl-5-oxo-5H-[1]benzopyrono[2,3-b]pyridine-3-carbonitrile, 1-aminoanthraquinone, anthraquinone-2-carboxylic acid, 1,5-dihydroxyanthraquinone, anthrone, 9-anthryltrifluoromethyl ketone, 9-alkylanthracene derivative of the formula:
9-carboxylanthracene derivative of the formula:
1-carboxylanthracene derivative of the formula 6:
and mixtures thereof,
wherein
each of R a , R b , and R c is independently hydrogen, hydroxy, hydroxyalkyl, optionally substituted C 1 -C 5 alkyl, or alkoxyalkyl.
39 . The method of claim 36 further comprising the steps of producing said anti-reflective coating composition, wherein said anti-reflective coating composition producing step comprises
(i) admixing said anti-reflective coating polymer with an organic solvent; and
(ii) filtering said admixture.
40 . The method of claim 39 , wherein said organic solvent is selected from the group consisting of ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, cyclohexanone, and propylene glycol methyletheracetate.
41 . The method of claim 36 , wherein said curing step comprises heating said coated substrate to temperature in the range of from about 100° C. to about 300° C.
42 . A semiconductor device produced by a method of claim 36 .Join the waitlist — get patent alerts
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