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US4783391A
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Radiation-sensitive polyamide polymer composition with anthraquinone monoazide
Assignee: Toray Industries Inc
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Filing: 1986-11-25
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Granted: 1988-11-08
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Expires: 2006-11-25
Abstract
Abstract A radiation-sensitive composition is described, which is comprised of (1) a polymer containing repeating units of the formula: <IMAGE> wherein R1 is a trivalent or tetravalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R2 is a divalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R3 is hydrogen or an ammonium ion, n is 1 or 2, and COOR3 is located in an ortho or peri position with respect to the amide linkage, (2) an organic compound having a radiation-dimerizable or radiation-polymerizable olefinic double bond and an amino radical or a quaternary ammonium salt, and (3) an aromatic monoazide compound [III] having no substituent or having a neutral or acidic substituent. This composition has a highly improved radiation sensitivity and the sensitive wavelength region of this composition is very broad. This composition can give a highly heat-resistant relief pattern with a good edge sharpness. Heat-resistant relief patterns obtained from this composition are especially useful as insulating passivation or protective coatings in semiconductor devices.
Inventors
- 👤 Gentaro Ohbayashi
- 👤 Susumu Umemoto
- 👤 Hiroo Hiramoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 16:32
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/008; G03F7/012; G03F7/0125; G03F7/027; G03F7/032; G03F7/037
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
190 words
A radiation-sensitive composition comprising a mixture of: (1) a polymer containing repeating units (A) represented by the following formula: ##STR21## wherein R 1 is a trivalent or tetravalent aromatic or heteroaromatic organic group having 6 to 30 carbon atoms, R 2 is a divalent aromatic or heteroaromatic organic group having 6 to 30 carbon atoms, R 3 is a hydrogen atom or an ammonium ion, n is an integer of 1 or 2, and COOR 3 is located in an ortho or peri position with respect to the amide linkage, (2) 0.05 to 2 equivalents, to the whole carboxyl or carboxylate groups of the polymer [I], to an organic compound [II] having a radiation-dimerizable or radiation-polymerizable olefinic double bond and an amino radical or a quaternary ammonium salt, and (3) 0.1 to 30% by weight, based on the weight of the polymer [I], of an aromatic monoazide compound [III] having an aromatic component selected from the group consisting of: ##STR22## said monoazide compound having no substituent or having a neutral or acidic substituent directly attached to the aromatic ring of the monoazide compound, and having 6 to 30 carbon atoms.
Claim 2
Dependent Claim
190 words
A radiation-sensitive composition comprising a mixture of: (1) a polymer containing repeating units (A) represented by the following formula: ##STR21## wherein R 1 is a trivalent or tetravalent aromatic or heteroaromatic organic group having 6 to 30 carbon atoms, R 2 is a divalent aromatic or heteroaromatic organic group having 6 to 30 carbon atoms, R 3 is a hydrogen atom or an ammonium ion, n is an integer of 1 or 2, and COOR 3 is located in an ortho or peri position with respect to the amide linkage, (2) 0.05 to 2 equivalents, to the whole carboxyl or carboxylate groups of the polymer [I], to an organic compound [II] having a radiation-dimerizable or radiation-polymerizable olefinic double bond and an amino radical or a quaternary ammonium salt, and (3) 0.1 to 30% by weight, based on the weight of the polymer [I], of an aromatic monoazide compound [III] having an aromatic component selected from the group consisting of: ##STR22## said monoazide compound having no substituent or having a neutral or acidic substituent directly attached to the aromatic ring of the monoazide compound, and having 6 to 30 carbon atoms.
Claim 3
Dependent Claim
20 words
A composition as set forth in claim 1, wherein the polymer [I] contains at least two kinds of repeating units.
Claim 4
Dependent Claim
16 words
A composition as set forth in claim 1, wherein "n" in the formula (A) is 2.
Claim 5
Dependent Claim
48 words
A composition as set forth in claim 1, wherein R 1 is a trivalent or tetravalent aromatic residue of a formula selected from the group consisting of ##STR23## in which M is --O--, --SO 2 --, --CH 2 --, ##STR24## or ##STR25## and z is 0 or 1.
Claim 6
Dependent Claim
25 words
A composition as set forth in claim 1, wherein R 1 is an aromatic residue of a formula selected from the group consisting of ##STR26##
Claim 7
Dependent Claim
25 words
A composition as set forth in claim 1, wherein the polymer [I] of the formula (A) contains at least two kinds of R 2 s.
Claim 8
Dependent Claim
93 words
A composition as set forth in claim 1, wherein R 2 is a divalent aromatic residue selected from the group consisting of a benzene residue, a biphenyl compound residue of the formula: ##STR27## wherein M' is --O--, SO 2 --, --CH 2 --, ##STR28## or --CO-- and z is an integer of 0 or 1, and a polyphenyl compound residue of the following formula: ##STR29## wherein Y is ##STR30## each of which may have no substituent or have a nuclear substituent selected from the group consisting of amino, amide, carboxyl, and sulfone-amide groups.
Claim 9
Dependent Claim
26 words
A composition as set forth in claim 1, wherein R 2 is a divalent aromatic residue of a formula selected from the group consisting of ##STR31##
Claim 10
Dependent Claim
48 words
A composition as set forth in claim 2, wherein at least one kind of the repeating units contain as R 2 an unsubstituted divalent aromatic or heteroaromatic residue and at least one kind of the repeating units contain as R 2 a substituted divalent aromatic or heteroaromatic residue.
Claim 11
Dependent Claim
36 words
A composition as set forth in claim 1, wherein part of the R 2 s in the recurring units (A) of the polymer [I] is comprised of a divalent aliphatic residue represented by the formula: ##STR32##
Claim 12
Dependent Claim
76 words
A composition as set forth in claim 1, wherein the compound [II] is at least one compound represented by the following formula: ##STR33## wherein R 4 is hydrogen or a phenyl group, R 5 is hydrogen or an alkyl group having 1 to 2 carbon atoms, R 6 is an alkylene group having 2 to 12 carbon atoms, and each of R 7 and R 8 is an alkyl group having 1 to 6 carbon atoms.
Claim 13
Dependent Claim
38 words
A composition as set forth in claim 1, wherein the compound [II] is at least one compound represented by the following formula: ##STR34## wherein R 9 is hydrogen or an alkyl group having 1 to 6 carbon atoms.
Claim 14
Dependent Claim
50 words
A composition as set forth in claim 1, wherein the compound [II] is at least one compound represented by the following formula: ##STR35## wherein R 10 is hydrogen or a methyl group, n is an integer of from 1 to 3, and the sum of l and n is 3.
Claim 15
Dependent Claim
36 words
A composition as set forth in claim 1, wherein the compound [II] is at least one compound selected from the group consisting of diethylaminoethyl methacrylate, diethylaminoethyl acrylate, dimethylaminoethyl methacrylate, dimethylaminoethyl acrylate, 2-vinylpyridine, 2-methyl-5-vinylpyridine, allylamine and methyllylamine.
Claim 16
Dependent Claim
23 words
A composition as set forth in claim 1, wherein the compound [III] is an aromatic monoazide compound having 10 to 21 carbon atoms.
Claim 17
Dependent Claim
38 words
A radiation-sensitive polymer composition as set forth in claim 1, wherein the amount of said aromatic monoazide compound is 0.5 to 15% by weight based on the weight of the polymer [I] having the main recurring units (A).
Claim 18
Dependent Claim
29 words
A radiation-sensitive polymer composition as set forth in claim 1, wherein said radiation-sensitive polymer composition further comprises a sensitizer selected from the group consisting of Michler's ketone and 4,4'-bis(diethylamino)-benzophenone.
Claim 19
Dependent Claim
37 words
A composition as set forth in claim 1, wherein the amount of said compound [II] is 0.3 to 2 equivalents to the whole carboxyl or carboxylate groups of the polymer [I] having the main recurring units (A).
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1991-11-08 | 1992-05-09 | 1992-11-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-08 | 1996-05-09 | 1996-11-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-08 | 2000-05-09 | 2000-11-08 | $7700.00 | Window Closed / Lapsed |