Electroactive compounds, compositions and devices and methods of making the same

• US 5,334,333 A
• Filed: 12/17/1990
• Issued: 08/02/1994
• Est. Priority Date: 12/17/1990
• Status: Expired due to Fees

• Current Assignee: ATOFINA Chemicals, Inc. (Arkema)
• Original Assignee: Elf Atochem North America, Inc. (Totalenergies Se)
• Inventors: Goetz, Frederick J.
• Primary Examiner(s): TUCKER, PHILIP C
• Application Number:
  US07/629,781
• Time in Patent Office: 1,324 Days
• Field of Search: 568/321, 568/327, 252/582, 359/328, 359/329, 544/241, 544/224, 544/242, 544/335, 544/334, 544/298, 544/319, 546/79, 546/152, 546/153, 546/339, 548/100, 548/120, 548/121, 548/146, 548/181, 548/182, 548/215, 548/217, 548/225, 548/226, 548/300.1, 548/302.7, 548/452, 548/400, 549/29, 549/43, 549/44, 549/51, 549/460, 549/429
• US Class Current: 252/582
• CPC Class Codes: C07C 211/50 with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07C 211/52 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 255/40 the carbon skeleton being further substituted by doubly-bound oxygen atoms
• CPC Class Codes: C07C 255/42 the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 2602/08 the other ring being five-membered, e.g. indane
• CPC Class Codes: C07C 49/757 containing —CHO groups
• CPC Class Codes: C07D 213/50 Ketonic radicals
• CPC Class Codes: C07D 213/57 Nitriles
• CPC Class Codes: C07D 215/14 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 263/32 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 277/24 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 277/84 Naphthothiazoles
• CPC Class Codes: C07D 293/12 Selenazoles; Hydrogenated selenazoles
• CPC Class Codes: G02F 1/065 in an optical waveguide structure

Abstract

The present invention relates to electroactive compounds capable of undergoing a change in light absorption and refraction due to an applied electric field and a permanent change in refraction due to exposure to predetermined bands of optical radiation. The present invention also relates to electroactive compositions containing such electroactive compounds, electrooptical components comprised of such electroactive compositions and electrooptical devices comprised of such electrooptical components, as well as novel processes of making the same.

Claims

1. A process of making an aldehyde compound having a structure:

##STR174## wherein R is a diradical comprising a substituted or unsubstituted aromatic carboxyclic ring system of e members, where e is 6 to 20, or substituted or unsubstituted aromatic heterocyclic ring system of f members, where f is 4 to 20, wherein the substituents are zero to (e-2) or (f-2) same or different J, L, R¹, R², G--R³ or Q substituents for the carbocyclic and heterocyclic ring systems, respectively;

G is a diradical comprising substituted or unsubstituted --(--HC═

CH--)_m --, where m is an integer from 1 to 10, substituted or unsubstituted --(CH₂)_n --, where n is an integer from 1 to 22, a substituted or unsubstituted aromatic ring system of 6 to 16 carbons or a substituted or unsubstituted aromatic heterocyclic ring system of g members, where g is 5 to 14, the members being carbon atoms and 1 to (g-1) heteroatoms, the heteroatom being one or more of N, P, As, Sb, O, S, Se or Te, the G substitutents being J¹ and L¹ with the proviso that the maximum number of G substituents is 6;

G¹ and G² each independently have the same definition as G;

J is an electron donating group --(CH₂)_n --R¹, --S--R¹, --O--R¹, --N(R¹)(R²), --G--R¹, --(CH₂)_n --G--R¹, --S--G--R¹, --O--G--R¹, --N(G¹ --R¹)(G² --R²);

J¹ is --(CH₂)_n --R¹, --S--R¹, --O--R¹ or --N(R¹)(R²);

J², J³ and J⁴ each independently have the same definition as J;

L is --C═

N, --N═

O, --NO₂, --C(═

O)--J², ##STR175## L¹ independently has the same definition as L;

R¹ and R² are independently H, F, Cl, Br, I, Q, alkyl of 1 to 22 carbons, cycloalkyl of 3 to 22 carbons, a substituted or unsubstituted aromatic ring system of 6 to 16 carbons or a substituted or unsubstituted aromatic heterocyclic ring system of h members in the ring system, where h is 5 to 14, the members being carbon atoms and 1 to (h-1) heteroatoms, the heteroatom being one or more of N, P, As, Sb, O, S, Se or Te, the R¹ or R² substituents being J¹ or L¹ with the proviso that the maximum number of R¹ or R² substituents is 6;

R³ is H, F, Cl, Br, I, Q, alkyl of 1 to 22 carbons or cycloalkyl of 3 to 22 carbons;

Q is a polymerizable group, the polymerizable group being alpha,beta-unsaturated carbonyl of 4 to 26 carbons, vinyl ether of 3 to 25 carbons, carboxylic acid of 2 to 23 carbons, ester of 3 to 45 carbons, alcohol of 1 to 22 carbons, alkyl amine of 1 to 44 carbons, 1-substituted or 1,1-substituted alkylene of 2 to 44 carbons, or a polymerizable group of 1 to 44 carbons containing a nucleophilically replaceable group of zero to 22 carbons, the nucleophilically replaceable group being F, Cl, Br, I, an alkyl halide or an --O--L group, the Q substituents being J, L, R¹, R², G--R³,

any M⁵ independently is any of J, L, R¹, R², G--R³ or Q;

Tⁱ⊕

is a stable metallic or nonmetallic cation; and

i is an integer of 1 to 4;

the process comprising

(a) reacting a first starting material having a structure ##STR176## where J⁵ and J⁶ are independently --S--R¹, --OR¹, or --N(R¹)(R²),

with a substituted or unsubstituted phthalide having a structure ##STR177## in the presence of a strong base and an organic solvent for the reactants and base;

(b) heating the reaction mixture of step (a) at a sufficient temperature and for a sufficient time to obtain an intermediate reaction product;

(c) heating the intermediate reaction product of step (b) in the presence of a mineral acid at a sufficient temperature and for a sufficient time to obtain the aldehyde compound; and

(d) isolating the aldehyde compound.

2. The process of claim 1 wherein,

where R is a substituted or unsubstituted diradical comprising an aromatic carbocyclic ring system, the aromatic carbocyclic ring system is any R⁸ diradical as follows, where any of M, M¹, M² or M³ is independently any one of J, L, R¹, R², G--R³ or Q, and the subscript "*" signifies the number of available valences for the substituents:

##STR178## and when R is a substituted or unsubstituted aromatic heterocyclic ring system, the heterocyclic ring system is any diradical R⁹ as follows, where any E¹ is N, P or As, any E is O, S, Se or Te, any of M, M¹ or M² is independently any one of J, L, R¹, R², G--R³ or Q, and the subscript "*" signifies the number of available valences for the substituents;

##STR179## where G, G¹ or G² are independently a substituted or unsubstituted aromatic ring system, the ring system is any diradical R⁸ and where G, G¹ or G² is a substituted or unsubstituted aromatic heterocyclic ring system, the heterocyclic ring system is any diradical R⁹, and

if R¹ or R² is attached to O, N or S, R¹ and R² are independently H, Q, alkyl of 1 to 22 carbons, cycloalkyl of 3 to 22 carbons, or a substituted or unsubstituted aromatic ring system of 6 to 16 carbons or a substituted or unsubstituted aromatic heterocyclic ring system of h members in the ring system, where h is 5 to 14, the members being carbon atoms and 1 to (h-1) heteroatoams, the heteroatom being one or more of N, P, As, Sb, O, S, Se or Te, the R¹ or R² substituents being J¹ or L¹ with the proviso that the maximum number of R¹ or R² substituents is 6.

3. The process of claim 2, wherein in any R⁹ diradical, any E¹ is N and any E is O or S.

4. The process of claim 1, wherein the mineral acid of step (c) is in a solution of an organic acid.

5. The process of claim 2, wherein the mineral acid of step (c) is in a solution of an organic acid.

6. The process of claim 3, wherein the mineral acid of step (c) is in a solution of an organic acid.