EP0583205A1
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EP
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Polymeric dyes for antireflective coatings
Assignee: International Business Machines Corp
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Filing: 1993-06-15
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Granted: —
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Expires: 2013-06-15
Abstract
Abstract A composition and methods for the use and manufacture thereof are provided for a polymeric dye. The composition comprises one or more aminoaromatic chromophores in conjunction with polymers having an anhydride group or the reaction products thereof. The composition is particularly useful as an underlaying antireflective coating with microlithographic photoresists for the absorbtion of near or deep ultraviolet radiation.
Inventors
- 👤 Christopher John Knors
- 👤 Wayne Martin Moreau
- 👤 Elwood Herbert Macy
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 16:34
CPC Classifications
C; C09; C09B; C09B69/00; C09B69/10; G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03F7/091
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
21 words
A film forming composition comprising the imide reaction product of at least one aminoaromatic chromophore with a polymer comprising an anhydride.
Claim 2
Dependent Claim
48 words
The material of claim 1 wherein the composition exhibits an optical absorbance coefficient of at least 10/µm for ultraviolet radiation having at least one wavelength in the range from about 193 nm to about 300 nm or in the range from about 365 nm to about 436 nm.
Claim 3
Dependent Claim
27 words
The material of claim 1 wherein the polymer comprises a repeat unit of the form where R1 and R2 may be independently H, alkyl, phenyl or hydrogen.
Claim 4
Dependent Claim
29 words
The material of claim 1 wherein the polymer comprises a repeat unit of the form where R3, R4, R5, and R6 may be independently H, alkyl, phenyl or hydrogen.
Claim 5
Dependent Claim
14 words
The material of claim 1 wherein the aminoaromatic chromophore is a primary aryl amine.
Claim 6
Dependent Claim
29 words
The material of claim 1 wherein the aminoaromatic chromophore is selected from the group consisting of aminoanthracenes, aminonaphthalenes, benzylamines, N-(2,4-dinitrophenyl)-1,4-benzenediamine, p-(2,4-dinitrophenylazo)aniline, p-(4-N,N-dimethylaminophenylazo)aniline, 4-amino-2-(9-(6-hydroxy-3-xanthenonyl))-benzoic acid, 2,4-dintrophenylhydrazine, dinitroaniline, aminobenzothiazoline, and aminofluorenone.
Claim 7
Dependent Claim
39 words
The film forming composition of claim 1 wherein said polymer comprising an anhydride is a copolymer comprising a first repeat unit having an anhydride group and a second repeat unit having an ethylene group with at least one substituent.
Claim 8
Dependent Claim
48 words
The material of claim 7 wherein the composition exhibits an optical absorbance coefficient of at least 10/µm for ultraviolet radiation having at least one wavelength in the range from about 193 nm to about 300 nm or in the range from about 365 nm to about 436 nm.
Claim 9
Dependent Claim
26 words
The material of claim 7 wherein said first repeat unit is of the form where R1 and R2 may be independently H, alkyl, phenyl or hydrogen.
Claim 10
Dependent Claim
28 words
The material of claim 7 wherein said first repeat unit is of the form where R3, R4, R5, and R6 may be independently H, alkyl, phenyl or hydrogen.
Claim 11
Dependent Claim
14 words
The material of claim 7 wherein the aminoaromatic compound is a primary aryl amine.
Claim 12
Dependent Claim
29 words
The material of claim 7 wherein the aminoaromatic compound is selected from the group consisting of aminoanthracenes, aminonaphthalenes, benzylamines, N-(2,4-dinitrophenyl)-1,4-benzenediamine, p-(2,4-dinitrophenylazo)aniline, p-(4-N,N-dimethylaminophenylazo)aniline, 4-amino-2-(9-(6-hydroxy-3-xanthenonyl))-benzoic acid, 2,4-dintrophenylhydrazine, dinitroaniline, aminobenzothiazoline, and aminofluorenone.
Claim 13
Dependent Claim
52 words
The material of claim 7, wherein said second repeat unit having an ethylene group with at least one substituent is of the form where X and Y may be independently alkoxy, alkyl having 1-5 carbons, substituted carbonyl, substituted or unsubstituted oxycarbonyl, or substituted or unsubstituted phenyl, or where X may be H.
Claim 14
Dependent Claim
22 words
A film forming composition comprising the tertiary amide reaction product of at least one aminoaromatic chromophore with a polymer comprising an anhydride.
Claim 15
Dependent Claim
18 words
The material of claims 1, 7, or 14 wherein the imide reaction product is dissolved in a solvent.
Claim 16
Independent Claim
78 words
A method of producing a film forming composition comprising the imide reaction product of at least one aminoaromatic chromophore with a polymer comprising an anhydride, said method comprising the steps of: charging a reaction vessel with the said polymer and the said aminoaromatic compound and a solvent comprising cyclopentanone, cyclohexanone, or Q-butyrolactone; and refluxing or heating the reactants; and filtering the reaction product; and applying the filtered product to a lithographic substrate without completely drying the reaction product.
Claim 17
Independent Claim
77 words
A method of producing a film forming composition comprising the imide reaction product of at least one aminoaromatic chromophore with a polymer comprising an anhydride, said method comprising the steps of: obtaining a mixture of the said polymer and the said aminoaromatic compound and a solvent comprising cyclopentanone, cyclohexanone, or Q-butyrolactone; and filtering the mixture; and applying the filtered mixture to a lithographic substrate; and heating the mixture to form said imide reaction product in situ .
Claim 18
Independent Claim
69 words
A method for producing an antireflective layer on a lithographic substrate comprising the steps of: dissolving, in an organic solvent, a composition comprising the imide reaction product of at least one aminoaromatic chromophore with a polymer comprising an anhydride; and applying the solution to a lithographic substrate by means of spin casting, extrusion coating, spraying, dipping, or roller coating; and removing at least a portion of said organic solvent.
Claim 19
Dependent Claim
24 words
The method of claim 18 having the additional step of applying a photosensitive film forming material over said antireflective layer on a lithographic substrate.
Claim 20
Independent Claim
79 words
A method of producing a film forming composition comprising the tertiary amide reaction product of at least one aminoaromatic chromophore with a polymer comprising an anhydride, said method comprising the steps of: charging a reaction vessel with the said polymer and the said aminoaromatic compound and a solvent comprising cyclopentanone, cyclohexanone, or Q-butyrolactone; and refluxing or heating the reactants; and filtering the reaction product; and applying the filtered product to a lithographic substrate without completely drying the reaction product.
Claim 21
Independent Claim
78 words
A method of producing a film forming composition comprising the tertiary amide reaction product of at least one aminoaromatic chromophore with a polymer comprising an anhydride, said method comprising the steps of: obtaining a mixture of the said polymer and the said aminoaromatic compound and a solvent comprising cyclopentanone, cyclohexanone, or Q-butyrolactone; and filtering the mixture; and applying the filtered mixture to a lithographic substrate; and heating the mixture to form said imide reaction product in situ .
Claim 22
Independent Claim
70 words
A method for producing an antireflective layer on a lithographic substrate comprising the steps of: dissolving, in an organic solvent, a composition comprising the tertiary amide reaction product of at least one aminoaromatic chromophore with a polymer comprising an anhydride; and applying the solution to a lithographic substrate by means of spin casting, extrusion coating, spraying, dipping, or roller coating; and removing at least a portion of said organic solvent.
Claim 23
Dependent Claim
24 words
The method of claim 22 having the additional step of applying a photosensitive film forming material over said antireflective layer on a lithographic substrate.
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