US5153303A
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Polyimides prepared from disubstituted aromatic tetracarboxylic acid dianhydrides
Assignee: OCG Microelectronic Materials Inc
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Filing: 1990-01-19
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Granted: 1992-10-06
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Expires: 2010-01-19
Abstract
Abstract Fully cyclized polyimides based on aromatic tetracarboxylic acid dianhydrides with substitution in the positions ortho to the bridging moiety and aromatic diamines, exhibiting solubility in organic solvents, increased glass transition temperatures, low coefficients of thermal expansion and photoimagability; said polyimides being suitable for the production of films, protective coatings and photolithographic relief images.
Inventors
- 👤 Stanley J. Jasne
- 👤 Pasquale A. Falcigno
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 18:32
CPC Classifications
C; C07; C07C; C07C65/00; C07C65/32; C07C65/34; C07D; C07D307/00; C07D307/77; C07D307/87; C07D307/89; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1039; C08G73/1046; C08G73/1053; C08G73/1057; C08G73/106; C08G73/1064; C08G73/1067; C08G73/1071; C08G73/1096; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31721
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
141 words
A polyimide of at least one aromatic tetracarboxylic dianhydride and at least one aromatic diamine which comprises 5 to 100 mol % of at least one structural element of the formula I ##STR28## and 95 to 0 mol % of at least one structural element of the formula II ##STR29## wherein A is a direct bond or A is ##STR30## --SO 2 --, or C(CF 3 ) 2 ; R is independently halogen, OH, OR 1 , NO 2 , COOR 1 , CF 3 or (CF 2 ) 1-4 CF 3 and R 1 is C 1 -C 6 alkyl; Z is an unsubstituted or substituted tetravalent radical to which in each case two carbonyl groups are bonded in the ortho- or peri-position with the proviso that Z is not ##STR31## X is the divalent radical or an aromatic diamine.
Claim 2
Dependent Claim
141 words
A polyimide of at least one aromatic tetracarboxylic dianhydride and at least one aromatic diamine which comprises 5 to 100 mol % of at least one structural element of the formula I ##STR28## and 95 to 0 mol % of at least one structural element of the formula II ##STR29## wherein A is a direct bond or A is ##STR30## --SO 2 --, or C(CF 3 ) 2 ; R is independently halogen, OH, OR 1 , NO 2 , COOR 1 , CF 3 or (CF 2 ) 1-4 CF 3 and R 1 is C 1 -C 6 alkyl; Z is an unsubstituted or substituted tetravalent radical to which in each case two carbonyl groups are bonded in the ortho- or peri-position with the proviso that Z is not ##STR31## X is the divalent radical or an aromatic diamine.
Claim 3
Dependent Claim
20 words
The polyimide of claim 1, wherein A is the direct bond or A is ##STR32## --O-- or --SO 2 --.
Claim 4
Dependent Claim
9 words
The polyimide of claim 2, wherein A is ##STR33##
Claim 5
Dependent Claim
11 words
The polyimide of claim 1, wherein R is halogen or methoxy.
Claim 6
Dependent Claim
9 words
The polyimide of claim 4, wherein R is chlorine.
Claim 7
Dependent Claim
12 words
The polyimide of claim 1, wherein said dianhydride is 2,2'-dichloro-4,4',5,5'-benzophenonetetracarboxylic acid dianhydride.
Claim 8
Dependent Claim
19 words
The polyimide of claim 1, wherein X is a divalent, mono- or polynuclear C 6 -C 22 arylene radical.
Claim 9
Dependent Claim
11 words
The polyimide of claim 1, wherein X is a phenylene radical.
Claim 10
Dependent Claim
398 words
A polyimide according to claim 1, in which an aromatic radical X has the formulae III, IIIa or IIIb ##STR34## in which, in formula III, the free bonds are in the meta- or para-position relative to one another, in formula IIIa the free bonds are in the meta-or para-position relative to the R 11 group and R 5 and R 6 are bonded in the two ortho-positions of the free bond, and in formula IIIb the free bonds are in the 2-,3-,6- or 7-positions and R 5 and R 6 are in the two ortho-positions of the free bonds, R 11 is a direct bond or R 11 is --O--, --S--, --SS--, --SO--, --SO 2 --, --CO--, --COO--, --NH--, ##STR35## with 1 to 6 C atoms in the alkyl ##STR36## --CONH--, --CON-alkyl- with 1 to 6 C atoms in the alkyl, --CON-phenyl-, --CON-benzyl-, ##STR37## in which Y is ##STR38## and R 17 is a hydrogen atom, C 1 -C 6 -alkyl or phenyl, linear or branched alkylene with 1 to 3 C atoms, alkylidene which has 2 to 12 C atoms and is unsubstituted by Cl or F, cycloalkylidene with 5 or 6 ring carbon atoms, phenylene, phenylenedioxy or the group ##STR39## in which R 3 and R 4 are alkyl or alkoxy with 1 to 6 C atoms, phenyl, benzyl, phenoxy or benzyloxy, r is a number from 1 to 10, t is 0 or 1, s is 0 or 1, R' is --O-- or --S--, Q is C 1 -C 6 -alkylene and q is a number from 1 to 100 R 5 and R 6 are alkyl or alkoxy with 1 to 12 C atoms, alkoxyalkyl with 2 to 12 C atoms, cyclopentyl, cyclohexyl or benzyl, or, in the formula III or IIIa R 5 and R 7 are bonded in adjacent positions and together are trimethylene or tetramethylene, in which case R 6 is hydrogen, alkyl or alkoxy with 1 to 12 C atoms, alkoxyalkyl with 2 to 12 C atoms, cyclopentyl, cyclohexyl or benzyl a hydrogen atom, or R 7 and R 8 are hydrogen atoms or independently have the meanings of R 5 and R 6 , and R 9 and R 10 are hydrogen atoms or independently have the meanings of R 5 and R 6 , or R 7 and R 9 in formula IIIa together are trimethylene or tetramethylene.
Claim 11
Dependent Claim
106 words
A polyimide according to claim 9, in which X in formula I is a radical of the formula ##STR40## in which the free bonds are in the meta- or para-position relative to one another, or of the formula ##STR41## in which R 5 and R 6 independently of one another are methyl, ethyl, n-propyl or isopropyl, R 7 and R 8 are hydrogen atoms or have the meaning of R 5 , or R 5 and R 7 together are trimethylene or tetramethylene and R 6 and R 8 are hydrogen atoms, and R 11 is a direct bond or R 11 CH 2 or CO.
Claim 12
Dependent Claim
87 words
A polyimide according to claim 1, in which x has the formula ##STR42## in which R 5 , R 6 , R 7 and R 8 are hydrogen or one free bond is in the 4'- or 5'-position and the other is in the 3-, 4- or 5-position and R 5 and R 6 or R 7 and R 8 are in the ortho-positions of the free bond and are alkyl or alkoxy with 1 to 12 C atoms or alkoxyalkyl with 2 to 12 C atoms.
Claim 13
Dependent Claim
69 words
A polyimide according to claim 1, in which Z is ##STR43## in which R o is a direct bond or R o is a bridge group of the formula ##STR44## in which R 2 , R 3 and R 4 are alkyl with 1 to 6 C atoms, phenyl or benzyl, and R 3 and R 4 are also alkoxy with 1 to 6 C atoms, phenoxy or benzyloxy.
Claim 14
Dependent Claim
36 words
A polyimide according to claim 12, in which Z is a radical of the formula ##STR45## in which R o is a direct bond or R o --O--, --SO 2 --, --CH 2 -- or --CO--.
Claim 15
Dependent Claim
19 words
A polyimide according to claim 13, in which Z is a radical of the formula ##STR46## or mixtures thereof.
Claim 16
Dependent Claim
18 words
A polyimide according to claim 1 which contains 100 mol % of structural elements of the formula I.
Claim 17
Dependent Claim
14 words
The polyimide of claim 15, wherein A is ##STR47## and each R is chlorine.
Claim 18
Dependent Claim
19 words
The polyimide of claim 16, wherein X is a mixture of the divalent radicals from diaminophenylindane and 3,5-diaminobenzoic acid.
Claim 19
Dependent Claim
16 words
The polyimide according to claim 1 which contains elements of both formula (I) and formula (II).
Claim 20
Dependent Claim
17 words
The polyimide of claim 18, wherein A is ##STR48## each R is chlorine and Z is ##STR49##
Claim 21
Dependent Claim
90 words
A process for the preparation of polyimides according to claim 1, which comprises subjecting at least one compound of the formula (I) of claim 1 or at least one compound of the formula I of claim 1 together with at least one tetracarboxylic dianhydride of the formula ##STR50## to a polycondensation reaction with at least one diamine of the formula H 2 N--X--NH 2 , when X and Z are as defined in claim 1, and then cyclizing the formed polyamide acid with heat or heat and a dehydrating agent.
Claim 22
Dependent Claim
19 words
A coated substrate comprising a carrier material onto which a coating of polyimide according to claim 1 is applied.
Claim 23
Dependent Claim
41 words
The coated substrate of claim 21, wherein said polyimide contains at least 30 mol % of a divalent radical derived from aromatic diamines containing acidic or phenolic functionalities and an effective dissolution inhibiting amount of a dissolution inhibitor for said polyimide.
Claim 24
Dependent Claim
40 words
A polyimide according to claim 7, wherein X is a radical of the formula ##STR51## wherein R 11 is a direct bond, --O--, --CO-- or --CH 2 -- and R 12 is hydrogen, methyl, ethyl, isopropyl, methoxy, hydroxy or carboxy.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-10-06 | 1996-04-06 | 1996-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-10-06 | 2000-04-06 | 2000-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-10-06 | 2004-04-06 | 2004-10-06 | $7700.00 | Window Closed / Lapsed |