US 5,962,658 AGranted

(3-oxoisoindolin-1-ylidine)propandinitrile derivatives and method for preparing the same

AssigneeSamsung Electronics Co., Ltd.

InventorsDong-Hack Suh, Hyun-Cheual Choi, Tae-Hyung Rhee

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Abstract

Derivatives of (3-oxoisoindolin-1-ylidine)propandinitrile, and a method for preparing the derivatives, are disclosed herein. The (3-oxoisoindolin-1-ylidine)propandinitrile derivatives can be prepared easily and at low cost. Also, the derivatives show good heat resistance at temperatures required for manufacturing an electro-optic device, and can minimize light loss at a near infrared light wavelength range by replacing hydrogen of the C--H bond with halogen atom. As a result, the derivatives of the present invention are useful as an optical material for an electro-optic device. In addition, the (3-oxoisoindolin-1-ylidine)propandinitrile derivatives can be used as an intermediate for synthesizing a new compound having good electro-optic characteristics and heat resistance.

Claims16

Dependent claims

A compound represented by the formula ##STR8## where Y.sub.1, Y.sub.2 and Y.sub.3 are each independently selected from the group consisting of hydrogen and halogen;

where X.sub.1 is selected from the group consisting of hydrogen, halogen, --NHR.sub.1, --OR.sub.1, --COOR.sub.1, --COR.sub.1, --NO.sub.2, and --N(R.sub.1)(R.sub.2), where R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.20 unsubstituted or substituted aliphatic hydrocarbon, C.sub.1 -C.sub.20 unsubstituted or substituted aliphatic cyclic hydrocarbon, and C.sub.1 -C.sub.20 unsubstituted or substituted aromatic hydrocarbon;
and
where X.sub.2 is selected from the group consisting of hydrogen, halogen, --NHR.sub.1, --OR.sub.1, --COOR.sub.1, --COR.sub.1, --NO.sub.2, --N(R.sub.1)(R.sub.2) and moieties represented by the following formulae:
##STR9## where R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.20 unsubstituted or substituted aliphatic hydrocarbon, C.sub.1 -C.sub.20 unsubstituted or substituted aliphatic cyclic hydrocarbon, and C.sub.1 -C.sub.20 unsubstituted or substituted aromatic hydrocarbon;
Y.sub.4, Y.sub.5, Y.sub.6 and Y.sub.7 are independently selected from the group consisting of hydrogen and halogen atom;
A.sub.1 and A.sub.2 are independetly selected from the group consisting of OR.sub.5 (where R.sub.5 is a hydrogen, alkyl or halogenated alkyl group), H, F, Cl, Br and I;
and R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen, halogen atom, --NHR.sub.1, --OR.sub.1, --COOR.sub.1, --COR.sub.1, --NO.sub.2, and --N(R.sub.1)(R.sub.2);
and
where X.sub.1, X.sub.2, Y.sub.1, Y.sub.2 and Y.sub.3 are not all hydrogen.

6 more elements

A method for preparing a (3-oxoisoindolin-1-ylidine)propandinitrile derivative, comprising the steps of:

mixing a 1-imino-3-oxoisoindolin derivative, malononitrile, and a solvent;
and
allowing the mixture to react at a temperature in the range of approximately 0 to 200.degree. C. for a time in the range of approximately 0.5 to 96 hours;
said 1-imino-3-oxoisoindolin derivative being ##STR11## where Y.sub.1, Y.sub.2 and Y.sub.3 are each independently selected from the group consisting of hydrogen and halogen;
where X.sub.1 is selected from the group consisting of hydrogen, halogen, --NHR.sub.1, --OR.sub.1, --COOR.sub.1, --COR.sub.1, --NO.sub.2, and --N(R.sub.1)(R.sub.2), where R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.20 unsubstituted or substituted aliphatic hydrocarbon, C.sub.1 -C.sub.20 unsubstituted or substituted aliphatic cyclic hydrocarbon, and C.sub.1 -C.sub.2, unsubstituted or substituted aromatic hydrocarbon;
and
where X.sub.2 is selected from the group consisting of hydrogen, halogen, --NHR.sub.1, --OR.sub.1, --COOR.sub.1, --COR.sub.1, --NO.sub.2, --N(R.sub.1)(R.sub.2) and moieties represented by the following formulae:
##STR12## where R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.20 unsubstituted or substituted aliphatic hydrocarbon, C.sub.1 -C.sub.20 unsubstituted or substituted aliphatic cyclic hydrocarbon, and C.sub.1 -C.sub.2 unsubstituted or substituted aromatic hydrocarbon;
Y.sub.4, Y.sub.5, Y.sub.6 and Y.sub.7 are independently selected from the group consisting of hydrogen and halogen atom;
A.sub.1 and A.sub.2 are independently selected from the group consisting of OR.sub.5 (where R.sub.5 is a hydrogen, alkyl or halogenated alkyl group), H, F, Cl, Br and I;
and R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen, halogen atom, --NHR.sub.1, --OR.sub.1, --COOR.sub.1, --COR.sub.1, --NO.sub.2, and --N(R.sub.1)(R.sub.2), and where X.sub.1, X.sub.2, Y.sub.1, Y.sub.2, and Y.sub.3 are not all hydrogen.

8 more elements

Dependencies are inferred from the claim text.