Hydrazine → 9-Fluorenone hydrazone

Unsymmetrical charge transport materials can be prepared by using an unsymmetrical linking compound such as 6-dimethyl-1, 4-benzoquinone. Alternatively, unsymmetrical charge transport materials can be prepared by the following procedure. In the first step, a first 9-fluorenone or a derivative thereof reacts with an excess of hydrazine at 50-70° C. for 1-6 hours to produce a first 9-fluorenone hydrazone compound or a derivative thereof. Then, the first 9-fluorenone hydrazone compound can be isolated and purified. In a subsequent step, a second 9-fluorenone derivative reacts with an excess of hydrazine at 50-70° C. for 1-6 hours to produce a second 9-fluorenone hydrazone derivative. Then, the second 9-fluorenone hydrazone derivative can be isolated and purified. In another step, the first 9-fluorenone hydrazone derivative reacts with a linking compound having 2 aldehyde groups or ketone groups, such as OCH—CHO, a quinone derivative, or a diphenoquinone derivative, in a mole ratio of 1:1 to form an 9-fluorenone azine compound having one aldehyde or ketone group. In the next step, the second 9-fluorenone hydrazone derivative reacts with the 9-fluorenone azine compound in a mole ratio of 1:1 to form the desired product. The desired product can be isolated and purified by recrystalization or/and column chromatography. A person or ordinary skill in the art can reduce the amount of symmetrical by-products, and these symmetrical by-product compounds can be separated in the purification steps.

1. additionUnsymmetrical charge transport materials
2. customcan be prepared
3. customAlternatively, unsymmetrical charge transport materials can be prepared by the following procedure

ORD record

ord-a453f07d5aa04e16a4fa21fb7c6c9382

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07501216B2