US 5,688,906 AGranted

Highly efficient nonlinear optical polyimides

AssigneeEnichem S.p.A.

InventorsKwan-Yue Alex Jen, Kevin Joel Drost

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Abstract

A method for forming a polyamic acid having nonlinear optical (NLO) or pre-NLO side chains, which method includes the steps of: (1) providing a bis-(aromatic dicarboxylic acid anhydride) containing at least one NLO or pre-NLO side chain having the structure represented by: D-R-A wherein D, R and A form a delocalized resonance configuration in which R is a pi-conjugated non-centrosymmetric moiety, A is hydrogen or an electron withdrawing moiety and D is an electron donating moiety covalently linked to the bis-(aromatic dicarboxylic acid anhydride); and (2) reacting the bis-(aromatic dicarboxylic acid anhydride) with an aromatic diamine to form a polyamic acid having NLO or pre-NLO side chains. Methods for preparing polyamic acids having NLO or pre-NLO side chains by reacting aromatic diamines having NLO or pre-NLO side chains with bis-(aromatic dicarboxylic acid anhydrides) are also disclosed. Methods of forming the polyamic acids into polyimides having NLO side chains are also included.

Claims47

Dependent claims

A method for preparing a polyamic acid having nonlinear optical (NLO) or pre-NLO side chains, which method comprises:

mixing in a polar aprotic solvent a 1:1 ratio of bis-(aromatic dicarboxylic acid anhydrides) and aromatic diamines, wherein either or both of said bis-(aromatic dicarboxylic acid anhydrides) and said aromatic diamines comprise bis-(aromatic dicarboxylic acid anhydrides) and aromatic diamines having at least one NLO or pre-NLO side chain present in a ratio of between about 1:99 and about 75:25 to unsubstituted bis-(acid anhydrides) and aromatic diamines;
so that a polyamic acid having NLO or pre-NLO side chains is formed in said polar aprotic solvent by condensation of said bis-(acid anhydrides) with said aromatic diamines;
and
wherein said NLO or pre-NLO side chains have the structure represented by:
D-R-A
wherein D, R and A form a delocalized resonance configuration in which R is a pi-conjugated non-centrosymmetric moiety comprising at least one heteroaromatic ring, or at least one fused ring system comprising a heteroaromatic ring, A is hydrogen or an electron withdrawing moiety and D is an electron donating moiety covalently linked to said bis-(aromatic dicarboxylic acid anhydride) or said aromatic diamine by nucleophilic substitution, and either D or A is only substituted on said heteroaromatic ring of R.

3 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/500,384Filed 7 Aug 1995 · continuation
Priority: 12 Dec 1990
Granted: 18 Nov 1997
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

C07D 333/22
With only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms: radicals substituted by…
C07D 333/24
With only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms: radicals substituted by…
C07D 333/36
Hetero atoms other than halogen: nitrogen atoms
C07D 333/44
With nitro or nitroso radicals directly attached to ring carbon atoms: attached in position 5

Family

Serial626,358Parent of this continuation · filed 12 Dec 1990
Serial101,368Parent of this continuation-in-part · filed 2 Aug 1993
Serial132,707Parent of this continuation · filed 6 Oct 1993
Serial158,184Parent of this continuation-in-part · filed 24 Nov 1995
US 5,514,799 AParent of this continuation-in-part
US 5,688,906 AThis patent

From the US filing history. Foreign family members aren’t listed.