US5514799A
Expired / Lapsed
US
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1,1-vinyl substituted nonlinear optical materials
Assignee: Enichem SpA
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Filing: 1993-08-02
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Granted: 1996-05-07
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Expires: 2013-08-02
Abstract
Abstract Nonlinear optical compounds having structures with delocalized resonance configurations corresponding to: ##STR1## wherein A 1 and A 2 are independently selected from electron withdrawing moieties; R 1 and R 2 are independently selected from aromatic rings, heteroaromatic rings and fused ring systems consisting of two or three aromatic or heteroaromatic rings; n and m are integers from one to five, and D 1 and D 2 are independently selected from hydrogen, electron donating groups and polymer attachment groups, with the proviso that at least one of D 1 and D 2 is an electron donating group. Polymers blended with, cured with, or having pendant side chains of the disclosed nonlinear optical materials and exhibiting second order nonlinear optical properties are also disclosed.
Inventors
- 👤 Pushkara R. Varanasi
- 👤 Kwan-Yue A. Jen
- 👤 King Y. Wong
- 👤 Robert M. Mininni
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:38
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/14; C07D295/155; C07C; C07C225/00; C07C225/22; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/60; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/22; C07D333/24; C07D333/26; C07D333/30; C07D333/36; C07D409/00; C07D409/02; C07D409/06; C07D409/14; C07D495/00; C07D495/02; C07D495/04; C09; C09B; C09B23/00; C09B23/0008; C09B23/005; C09B23/0058; C09B23/10; C09B23/105; G; G02; G02F; G02F1/00; G02F1/35; G02F1/355; G02F1/361; G02F1/3613; G02F1/3614; G02F1/3615; G02F1/3616; G02F1/3617; C07C2602/00; C07C2602/02; C07C2602/04; C07C2602/08
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
156 words
A nonlinear optical compound of the formula: ##STR24## wherein A 1 and A 2 are independently selected from the group consisting of electron withdrawing moieties; R 1 and R 2 are independently selected from the group consisting of aromatic rings, heteroaromatic rings and fused ring systems consisting of two or three aromatic or heteroaromatic tings, wherein at least one of R 1 or R 2 is a five-membered heteroaromatic ring or a fused ring system comprising a five-membered heteroaromatic ring; n and m are independently integers from one to five, inclusive; D 1 and D 2 are independently selected from the group consisting of hydrogen, electron donating groups and polymer attachment groups, with the proviso that at least one of D 1 and D2 is an electron donating group; and the compound formed by A 1 , A 2 , D 1 , D 2 , R 1 and R 2 possesses a delocalized resonance configuration.
Claim 2
Dependent Claim
156 words
A nonlinear optical compound of the formula: ##STR24## wherein A 1 and A 2 are independently selected from the group consisting of electron withdrawing moieties; R 1 and R 2 are independently selected from the group consisting of aromatic rings, heteroaromatic rings and fused ring systems consisting of two or three aromatic or heteroaromatic tings, wherein at least one of R 1 or R 2 is a five-membered heteroaromatic ring or a fused ring system comprising a five-membered heteroaromatic ring; n and m are independently integers from one to five, inclusive; D 1 and D 2 are independently selected from the group consisting of hydrogen, electron donating groups and polymer attachment groups, with the proviso that at least one of D 1 and D2 is an electron donating group; and the compound formed by A 1 , A 2 , D 1 , D 2 , R 1 and R 2 possesses a delocalized resonance configuration.
Claim 3
Dependent Claim
37 words
The nonlinear optical compound of claim 1, wherein said five-membered heteroaromatic ring has the structure: ##STR25## wherein Y is C or N and X is selected from the group consisting of O, S, Se, Te and N.
Claim 4
Dependent Claim
27 words
The nonlinear optical compound of claim 2, wherein both R 1 and R 2 are five-membered heteroaromatic rings or fused ring systems containing said five-membered heteroaromatic ring.
Claim 5
Dependent Claim
49 words
The nonlinear optical compound of claim 1, wherein R 1 and R 2 are independently selected from the group consisting of pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, tetrazole, pyrazole, pyrimidine, purine, quinolines, carbazole, benzene, naphthalene, furazan, pyrazine, indole, isoindole, indazole, phenothiazine, benzotriazole, anthracine, phenanthrene, quinazoline, pteridine and azophenanthrenes.
Claim 6
Dependent Claim
27 words
The nonlinear optical compound of claim 4, wherein R 1 and R 2 are independently selected from the group consisting of pyrrole, furan, thiophene, thiazole and oxazole.
Claim 7
Dependent Claim
22 words
The nonlinear optical compound of claim 1, wherein at least one of R 1 and R 2 is a fused ring system.
Claim 8
Dependent Claim
18 words
The nonlinear optical compound of claim 6, wherein both R 1 and R 2 are fused ring systems.
Claim 9
Dependent Claim
76 words
The nonlinear optical compound of claim 1, wherein A 1 and A 2 are independently selected from the group consisting of --NO 2 , --CN, --CHO, --COR 5 , --COOR 5 , --PO(OR 5 ) 2 , --SO 2 R 5 , --SO 3 R 5 and --PO(R 5 ) 2 , wherein R 5 is an alkyl group containing up to 15 carbon atoms, or A 1 and A 2 together comprise a ring moiety.
Claim 10
Dependent Claim
139 words
The nonlinear optical compound of claim 8, wherein A 1 and A 2 together comprise a ring moiety selected from the group consisting of N,N-dialkylbarbituric acids, N,N-dialkylthiobarbituric acids, rhodamines, hydrantoins, oxazolines and ring moieties having the structure: ##STR26## wherein X 1 and X 2 form a saturated or unsaturated five- to-eight-member cyclic ring or two-ring system having five- to eight-membered rings, and R 3 and R 4 are independently selected from the group consisting of O, S and --CI 1 I 2 , wherein I 1 and I 2 of R 3 and R 4 are independently selected from the group consisting of --CN, --NO 2 , --COR 5 , --COOR 5 , --SO 2 R 5 , --PO(R 5 ) 2 and --PO(OR5) 2 , and R 5 is an alkyl group containing up to 15 carbon atoms.
Claim 11
Dependent Claim
30 words
The nonlinear optical compound of claim 9, wherein A 1 and A 2 together comprise a moiety selected from the group consisting of 3-dicyanovinyl-indane-1-sulfone, 1,3-bissulfonylindane, indane-1,3-dione, 3-dicyanovinyl-indane-1-one and 1,3-bisdicyanovinyl indane.
Claim 12
Dependent Claim
18 words
The nonlinear optical compound of claim 8, wherein A 1 and A 2 comprise --NO 2 or --CN.
Claim 13
Dependent Claim
163 words
The nonlinear optical compound of claim 1, wherein D 1 and D 2 comprise electron donating groups independently selected from the group consisting of --NR 6 R 7 , --OR 8 , --SR 8 , --TeR 8 , --SeR 8 , --CH═NR 9 , --CH═N--NR 6 R 7 and --CH═C NR 6 R 7 ! 2 , wherein R 6 and R 7 are independently selected from the group consisting of hydrogen, alkyl groups containing up to 12 carbon atoms and alkyl groups containing up to 12 carbon atoms having reactive functional groups selected from the group consisting of hydroxyl, ethylene, acetylene, amine, thiol, sulfonic acid and carboxylic acid, or R 6 and R 7 together form a cyclic group containing up to 8 carbon atoms; R 8 is selected from the group consisting of alkyl groups containing up to 6 carbon atoms; and R 9 is selected from the group consisting of hydrogen and alkyl groups containing up to 10 carbon atoms.
Claim 14
Dependent Claim
30 words
The nonlinear optical compound of claim 12, wherein R 6 and R 7 together form a cyclic group selected from the group consisting of pyrrolidine, piperidine, piperazine and morpholine groups.
Claim 15
Dependent Claim
132 words
The nonlinear optical compound of claim 1, wherein D 1 or D 2 comprise electron donating groups having the structure: ##STR27## wherein E, F, G and H are members of a saturated or unsaturated five- to eight-membered cyclic ring or two-ring system having five- to eight-membered rings that are electron donating in nature and are independently selected from the group consisting of --CH--, --CH 2 --, O, N, S, Se, Te and --NR--; and R and R 10 are independently selected from the group consisting of hydrogen, alkyl moieties containing up to 18 carbon atoms and functionalized alkyl moieties containing up to 18 carbon atoms, wherein said functionalized alkyl moieties are selected from the group consisting of alkoxy, aminoalkyl, alkylhalide, hydroxyalkyl, alkylsulfide, alkylthiol, alkylazide, alkylcarboxylic, alkylsulfonic, alkylalkene, alkylisocyanate, alkylisothiocyanate and alkylalkyne moleties.
Claim 16
Dependent Claim
29 words
The nonlinear optical compound of claim 14, wherein D 1 or D 2 comprise an electron donating group selected from the group consisting of 1,3-dithiolium, 2-benzo-1,3-dithiolium and 2-ethylenedithio-1,3-dithiolium moieties.
Claim 17
Dependent Claim
17 words
The nonlinear optical compound of claim 1, wherein said compound comprises up to two polymer attachment groups.
Claim 18
Dependent Claim
57 words
The nonlinear optical compound of claim 16, wherein said polymer attachment groups are selected from the group consisting of functionalized alkyl moieties containing between 3 and 12 carbon atoms, wherein said functionalized alkyl moieties are selected from the group consisting of alkoxy, aminoalkyl, alkylhalide, hydroxy alkyl, alkylsulfide, alkylthiol, alkylazide, alkylcarboxylic, alkylsulfonic, alkylalkene, alkylisocyanate, alkylisothiocyanate and alkylalkyne moieties.
Claim 19
Dependent Claim
21 words
The nonlinear optical compound of claim 16, wherein one of D 1 or D 2 comprises a first polymer attachment group.
Claim 20
Dependent Claim
18 words
The nonlinear optical compound of claim 18, wherein said nonlinear optical compound comprises a second polymer attachment group.
Claim 21
Dependent Claim
23 words
The nonlinear optical compound of claim 18, wherein said first polymer attachment group comprises an electron donating group having a polymer attachment group.
Claim 22
Dependent Claim
17 words
The nonlinear optical compound of claim 1, wherein n and m are, independently, one, two or three.
Claim 23
Dependent Claim
26 words
A combination exhibiting second order nonlinear optical properties comprising said nonlinear optical compound of claim 1 and a medium chemically inert to said nonlinear optical compound.
Claim 24
Dependent Claim
16 words
The combination of claim 22, wherein said nonlinear optical compound has an external field-induced molecular alignment.
Claim 25
Dependent Claim
42 words
The combination of claim 22, comprising a blend of said nonlinear optical compound in a chemically inert medium selected from the group consisting of polyacrylates, polymethacrylates, polyacrylamides, polycarbonates, polyamides, polyesters, polystyrenes, polyimides, polyether ketones, polyether ether ketones, polyphenylene ethers and copolymers thereof.
Claim 26
Dependent Claim
14 words
. The combination of claim 24, wherein said chemically inert medium comprises a polyimide.
Claim 27
Dependent Claim
73 words
The combination of claim 22, wherein said nonlinear optical compound comprises at least one polymer attachment group, and said polymer attachment groups are covalently linked to at least one polymer comprising one or more monomeric subunits having a reactive group capable of being covalently attached to a polymer attachment group, whereby said nonlinear optical compound is covalently linked to said polymers at said reactive groups of said subunits via said polymer attachment groups.
Claim 28
Dependent Claim
55 words
The combination of claim 26, wherein said polymer attachment groups are independently selected from the group consisting of functionalized alkyl moieties containing between 3 and 12 carbon atoms, wherein said functionalized alkyl moieties are selected from the group consisting of alkoxy, aminoalkyl, alkylhalide, hydroxyalkyl, alkylsulfide, alkylthiol, alkylazide, alkylcarboxylic, alkylsulfonic, alkylalkene, alkylisocyanate, alkylisothiocyanate and alkylalkyne moieties.
Claim 29
Dependent Claim
66 words
The combination of claim 26, wherein said polymers comprise a plurality of said monomeric subunits having reactive groups covalently substituted with a nonlinear optical compound via said polymer attachment groups, so that the ratio of said monomeric subunits having reactive groups covalently linked to a nonlinear optical compound to monomeric subunits without a nonlinear optical compound covalently linked thereto is between about 1:99 and about 50:50.
Claim 30
Dependent Claim
15 words
The combination of claim 28, wherein said ratio is between about 5:95 and about 40:60.
Claim 31
Dependent Claim
11 words
The combination of claim 29, wherein said ratio is about 25:75.
Claim 32
Dependent Claim
85 words
The combination of claim 28, wherein said monomeric subunits having reactive groups covalently substituted with a nonlinear optical compound via a polymer attachment group, and said monomeric subunits without a nonlinear optical compound covalently linked thereto are independently selected from the group consisting of acrylate, amide, acrylamide, styrene, vinyl halide, acrylonitrile, vinyl alcohol, vinyl acetate, monomeric subunits, and monomeric subunits of polyimides, polyesters, polyphenylene ethers, polyether ketones, polyether ether ketones, acid anhydrides, polyethylene, polypropylene, polyisobutylene, polyisoprene, polyurethanes, polyquinolines, epoxy polymers, polybenzoxazoles, polybenzothiazoles, polysulfones and polycarbonates.
Claim 33
Dependent Claim
28 words
The combination of claim 31, wherein said monomeric subunits having reactive groups covalently substituted with a nonlinear optical compound via a functionalized alkyl moiety comprise polyimide monomeric subunits.
Claim 34
Dependent Claim
22 words
The combination of claim 32, wherein said chemically inert medium comprises a polymer matrix within which said nonlinear optical compound is cured.
Claim 35
Dependent Claim
12 words
The combination of claim 33, wherein said polymer matrix comprises a polyimide.
Claim 36
Dependent Claim
11 words
The combination of claim 33, wherein said polymer matrix is crosslinked.
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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) | 1999-05-07 | 1999-11-06 | 2000-05-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-05-07 | 2003-11-06 | 2004-05-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-05-07 | 2007-11-06 | 2008-05-07 | $7700.00 | Window Closed / Lapsed |