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

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, R.sup.1, R.sup.2, G--R.sup.3 or Q substituents for the carbocyclic and heterocyclic ring systems, respectively;
• G is a diradical comprising substituted or unsubstituted --(--HC.dbd.CH--).sub.m --, where m is an integer from 1 to 10, substituted or unsubstituted --(CH.sub.2).sub.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 J.sup.1 and L.sup.1 with the proviso that the maximum number of G substituents is 6;
• G.sup.1 and G.sup.2 each independently have the same definition as G;
• J is an electron donating group --(CH.sub.2).sub.n --R.sup.1, --S--R.sup.1, --O--R.sup.1, --N(R.sup.1)(R.sup.2), --G--R.sup.1, --(CH.sub.2).sub.n --G--R.sup.1, --S--G--R.sup.1, --O--G--R.sup.1, --N(G.sup.1 --R.sup.1)(G.sup.2 --R.sup.2);
• J.sup.1 is --(CH.sub.2).sub.n --R.sup.1, --S--R.sup.1, --O--R.sup.1 or --N(R.sup.1)(R.sup.2);
• J.sup.2, J.sup.3 and J.sup.4 each independently have the same definition as J;
• L is --C.dbd.N, --N.dbd.O, --NO.sub.2, --C(.dbd.O)--J.sup.2, ##STR175## L.sup.1 independently has the same definition as L;
• R.sup.1 and R.sup.2 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 R.sup.1 or R.sup.2 substituents being J.sup.1 or L.sup.1 with the proviso that the maximum number of R.sup.1 or R.sup.2 substituents is 6;
• R.sup.3 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, R.sup.1, R.sup.2, G--R.sup.3,
• any M.sup.5 independently is any of J, L, R.sup.1, R.sup.2, G--R.sup.3 or Q;
• T.sup.i.sym. 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 J.sup.5 and J.sup.6 are independently --S--R.sup.1, --OR.sup.1, or --N(R.sup.1)(R.sup.2),
• 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.