Organic compounds containing squaric acid or croconic acid moieties for application in electronic devices

Patent metadata

Field	Value
Publication number	US-9755155-B2
Application number	US-201314398291-A
Country	US
Kind code	B2
Filing date	Apr 8, 2013
Priority date	May 7, 2012
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

A compound containing a squaric acid or a croconic acid group as an anchoring group. The compound containing a squaric acid or a croconic acid group has formula 1:

where n is 1 or 2, and D is selected from an alkyl, aryl, aralkyl, heteroalkyl, heteroaryl or heteroaralkyl substituent, and each substituent is substituted or unsubstituted.

First claim

The invention claimed is:

1. A compound, comprising a squaric acid or croconic acid group as anchoring group, said compound represented by formula (2):

wherein, in formula (2), n is 1 or 2,
wherein A 1 is selected from the following moieties

wherein, at each occurrence and independently:
G is a cyclic or acyclic substituted, or straight or branched alkyl;
f=1 or 2;
K is O, S, or N;
g=0 or 1,

wherein the alkyl, alkoxy, amine, thiole group of —(K) g -(G) f can be one or more attached to the aryl and heteroaryl rings, in o-, m-, p-position.

2. The compound of claim 1 , wherein A 1 is selected from the following moieties

3. The compound of claim 1 , wherein A 1 is selected from the following moieties

4. The compound of claim 1 , which is represented by any one of

5. The compound of claim 1 , which is any one of

6. The compound of claim 1 , wherein the compound is

7. The compound of claim 1 , which is represented by

8. A light-emitting device, a Schottky barrier diode, a rectifier, a field effect transistor, a photovoltaic device, a photochemical device, a memory device, a sensing device, a display, or a photo-catalytical water splitting device that comprises:
a compound comprising a squaric acid or croconic acid group as anchoring group, said compound represented by formula (2):

wherein, in formula (2), n is 1 or 2,
wherein A 1 is selected from the following moieties

wherein, at each occurrence and independently:
G is a cyclic or acyclic substituted, or straight or branched alkyl;
f=1 or 2;
K is O, S, or N;
g=0 or 1,

wherein the alkyl, alkoxy, amine, thiole group of —(K) g -(G) f can be one or more attached to the aryl and heteroaryl rings, in o-, m-, p-position.

9. An assembly for use in an electronic device, said assembly comprising:
a) a conducting substrate, a semiconducting substrate, or an insulating organic or inorganic substrate, said substrate having a surface,
b) a layer of a compound present on said surface, wherein said layer is covalently attached to said surface via the squaric acid or croconic acid group of said compound, and
c) an organic layer, an inorganic layer, or an electrolyte layer deposited on said layer, wherein said
said compound is a compound comprising a squaric acid or croconic acid group as anchoring group, said compound represented by formula (2):

wherein, in formula (2), n is 1 or 2,
wherein A 1 is selected from the following moieties

wherein, at each occurrence and independently:
G is a cyclic or acyclic substituted, or straight or branched alkyl;
f=1 or 2;
K is O, S, or N;
g=0 or 1,

wherein the alkyl, alkoxy, amine, thiole group of —(K) g -(G) f can be one or more attached to the aryl and heteroaryl rings, in o-, m-, p-position.

Assignees

• Sony Corp

Inventors

• Fuhrmann Gerda
• Danner David
• Obermaier Markus
• Bamedi Zilai Ameneh
• Nelles Gabriele
• Scheller Lars Peter

Classifications

• C07D333/22

  Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom · CPC title

• C09B57/007 Primary

  Squaraine dyes · CPC title

• C07C2601/04

  with a four-membered ring · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0059 Primary

  Electricity · mapped topic