US 8,741,513 B2Granted

Method for preparing alizarin derivative compound, novel alizarin derivative compound, surface modification method, photoelectric conversion film, photoelectric conversion element, and electrophotographic photoreceptor

AssigneeFUJIFILM Corporation

InventorsKeita Takahashi, Kazumi Nii, Kazunari Yagi

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Abstract

The present invention provides a novel alizarin derivative compound and a simplified and low cost method for preparing an alizarin derivative compound including: obtaining a compound represented by Formula (2) using a compound represented by Formula (3); and obtaining an alizarin derivative compound represented by Formula (1) using the compound represented by Formula (2); in Formulae (1) to (3), R1 represents a hydrogen atom or a substituent; n represents an integer of 1 to 3, L represents a specific alkyl group; Q represents an atomic group needed to form an aromatic ring or a heteroaromatic ring with adjacent carbon atoms; and P represents an atomic group which includes an atom(s) selected from a hydrogen atom, a carbon atom, an oxygen atom, a sulfur atom, a silicon atom and a boron atom, and which is needed to form a ring structure group with adjacent two oxygen atoms and two carbon atoms;

Claims11

Dependent claims

A method for preparing an alizarin derivative compound comprising:

(A) preparing a compound represented by the following Formula (2) by protecting a cathecol moiety included in a compound represented by the following Formula (3) with a protecting group containing P;
and
(B) preparing an alizarin derivative compound represented by the following Formula (1) via alkylation of a 4-position of, and deprotection of the protecting group containing P at the cathecol moiety of the compound represented by Formula (2) prepared by the step (A);
wherein, in Formula (1), R1 represents a hydrogen atom or a substituent;
n represents an integer of 1 to 3, when n is 1, L represents —C(Ra1)(Ra2)(Ra3);
Ra1, Ra2, and Ra3 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
at least one of Ra1, Ra2, and Ra3 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
when n is 2, L represents a substituted or unsubstituted divalent linkage group having 2 to 20 carbon atoms;
when n is 3, L represents a substituted or unsubstituted trivalent linkage group having 2 to 30 carbon atoms;
and Q represents an atomic group which is needed to form an aromatic ring or a heteroaromatic ring with adjacent carbon atoms;
wherein, in Formula (2), P represents an atomic group which includes an atom(s) selected from a hydrogen atom, a carbon atom, an oxygen atom, a sulfur atom, a silicon atom and a boron atom, and which is needed to form a ring structure with two adjacent oxygen atoms and two carbon atoms;
and each of R1 and Q has the same definition as R1 and Q in Formula (1) respectively;
and wherein, in Formula (3), each of R1 and Q has the same definition as R1 and Q in Formula (1) respectively.

10 more elements

An alizarin derivative compound represented by the following Formula (5);

wherein, in Formula (5), R2 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;
m represents an integer of 0 to 4;
R3 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms;
n represents an integer of 1 to 3;
when n is 1, L represents —C(Ra1)(Ra2)(Ra3);
Ra1, Ra2, and Ra3 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
at least one of Ra1, Ra2, and Ra3 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
when n is 2, L represents a substituted or unsubstituted divalent linkage group having 2 to 20 carbon atoms;
and when n is 3, L represents a substituted or unsubstituted trivalent linkage group having 2 to 30 carbon atoms.

6 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/513,197Filed 3 Dec 2010
Priority: JP 2009-2779627 Dec 2009
Published: US 2012/0244462 A127 Sep 2012
Granted: 3 Jun 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

C07C 46/00
Preparation of quinones
C09B 1/08
Preparation from starting materials already containing the anthracene nucleus: dyes containing only OH-groups
C09B 1/14
Preparation from starting materials already containing the anthracene nucleus: dyes containing ether groups
C09B 57/008
Other synthetic dyes of known constitution: triarylamine dyes containing no other chromophores