Additive for light-emitting layer in light-emitting electrochemical cell, composition for forming light-emitting layer in light-emitting electrochemical cell, and light-emitting electrochemical cell

Patent metadata

Field	Value
Publication number	US-2018366646-A1
Application number	US-201615739837-A
Country	US
Kind code	A1
Filing date	Jul 22, 2016
Priority date	Jul 27, 2015
Publication date	Dec 20, 2018
Grant date	—

Abstract

An additive for a light-emitting layer contains a compound represented by formula (1):

where X is P, C, or S; A is a cyclic hydrocarbon group that may have H, a direct bond, a chain hydrocarbon group, or a heteroatom; R is H or an alkyl group, and a plurality of R may link together to form a ring, and if said ring is formed, at least one R is an alkyl group; m is 0 or 1; r is 1 when X is a phosphorous atom or a carbon atom and 2 when X is a sulfur atom; n is a number represented by 3-m when X is a phosphorous atom, and a number represented by 2-m if X is a carbon atom or a sulfur atom; and p is 1 when m is 0, at least 1 when m is 1, and is a substitutable number in A.

First claim

1 . An additive for a light-emitting layer of a light-emitting electrochemical cell, comprising a compound represented by the following general formula (1):

wherein X is a phosphorus atom, a carbon atom or a sulfur atom;
A is a hydrogen atom, a direct bond, an aromatic hydrocarbon group, a chain aliphatic hydrocarbon group, an alicyclic hydrocarbon group or a heterocyclic group;
R is a hydrogen atom or a branched-chain, straight-chain or cyclic alkyl group; when a plurality of R are present, they may be identical or different; the plurality of R bonded to the same X through O may be linked mutually and form a ring; and when the ring is not formed, at least one R is an alkyl group;
m is 0 or 1;
r is 1 when X is a phosphorus atom or a carbon atom, and is 2 when X is a sulfur atom;
n is a number represented by 3-m when X is a phosphorus atom, and is a number represented by 2-m when X is a carbon atom or a sulfur atom;
p is 1 when m is 0 or when m is 1 and A is a hydrogen atom, is 2 when m is 1 and A is a direct bond, and is a substitutable number on A when m is 1 and A is not a hydrogen atom or a direct bond; provided that if X is a phosphorus atom or a sulfur atom, A is not a direct bond; and if X is a sulfur atom, A is not a hydrogen atom.

2 . The additive according to claim 1 , wherein the compound represented by the general formula (1) is represented by the following general formula (2):

wherein R is as defined in the general formula (1).

3 . The additive according to claim 1 , wherein the compound represented by the general formula (1) is represented by the following general formula (3):

wherein A, R and p are as defined in the general formula (1).

4 . The additive according to claim 1 , wherein the compound represented by the general formula (1) is represented by the following general formula (a):

wherein R and p are as defined in the general formula (1); and A is an aromatic hydrocarbon group, a chain aliphatic hydrocarbon group, an alicyclic hydrocarbon group or a heterocyclic group.

5 . The additive according to claim 1 , wherein the compound represented by the general formula (1) is represented by the following general formula (b):

wherein R is as defined in the general formula (1).

6 . The additive according to claim 1 , wherein the light-emitting electrochemical cell comprises a light-emitting layer comprising a light-emitting material and an ionic compound; and the additive is used for improving dispersibility of the ionic compound in the light-emitting material.

7 . The additive according to claim 1 , wherein the light-emitting electrochemical cell comprises a light-emitting layer comprising a light-emitting material and an ionic compound; and the compound represented by the general formula (1) is contained in an amount of 1% by mass or more and 20% by mass or less in the light-emitting layer.

8 . A composition for forming a light-emitting layer of a light-emitting electrochemical cell, comprising a compound represented by the following general formula (1), an ionic compound and a light-emitting material:

wherein X is a phosphorus atom, a carbon atom or a sulfur atom;
A is a hydrogen atom, a direct bond, an aromatic hydrocarbon group, a chain aliphatic hydrocarbon group, an alicyclic hydrocarbon group or a heterocyclic group;
R is a hydrogen atom or a branched-chain, straight-chain or cyclic alkyl group; when a plurality of R are present, they may be identical or different; the plurality of R bonded to the same X through O may be linked mutually and form a ring; and when the ring is not formed, at least one R is an alkyl group;
m is 0 or 1;
r is 1 when X is a phosphorus atom or a carbon atom, and is 2 when X is a sulfur atom;
n is a number represented by 3-m when X is a phosphorus atom, and is a number represented by 2-m when X is a carbon atom or a sulfur atom;
p is 1 when m is 0 or when m is 1 and A is a hydrogen atom, is 2 when m is 1 and A is a direct bond, and is a substitutable number on A when m is 1 and A is not a hydrogen atom or a direct bond; and
provided that if X is a phosphorus atom or a sulfur atom, A is not a direct bond; and if X is a sulfur atom, A is not a hydrogen atom.

9 . The composition for forming a light-emitting layer according to claim 8 , wherein a cation of the ionic compound is at least one selected from a phosphonium cation, an ammonium cation and an imidazolium cation.

10 . The composition for forming a light-emitting layer according to claim 8 , wherein a cation of the ionic compound is a cation of at least one metal selected from Li, Na, K, Cs, Mg and Ca.

11 . The composition for forming a light-emitting layer according to claim 8 , wherein the composition contains the compound represented by the general formula (1) in an amount of 0.0001% by mass or larger and 10% by mass or smaller.

12 . The composition for forming a light-emitting layer according to claim 8 , wherein the light-emitting material is an organic polymeric light-emitting material of a polymer of paraphenylene vinylene, fluorene, 1,4-phenylene, thiophene, pyrrole, paraphenylene sulfide, benzothiazole, biothiophine or a derivative of these, or a copolymer containing these.

13 . A light-emitting electrochemical cell, comprising a light-emitting layer and an electrode disposed on each surface thereof,
wherein the light-emitting layer comprises a light-emitting material, an ionic compound and a compound represented by the following general formula (1):

wherein X is a phosphorus atom, a carbon atom or a sulfur atom;
A is a hydrogen atom, a direct bond, an aromatic hydrocarbon group, a chain aliphatic hydrocarbon group, an alicyclic hydrocarbon group or a heterocyclic group;
R is a hydrogen atom or a branched-chain, straight-chain or cyclic alkyl group; when a plurality of R are present, they may be identical or different; the plurality of R bonded to the same X through O may be linked mutually and form a ring; and when the ring is not formed, at least one R is an alkyl group;
m is 0 or 1;
r is 1 when X is a phosphorus atom or a carbon atom, and is 2 when X is a sulfur atom;
n is a number represented by 3-m when X is a phosphorus atom, and is a number represented by 2-m when X is a carbon atom or a sulfur atom;
p is 1 when m is 0 or when m is 1 and A is a hydrogen atom, is 2 when m is 1 and A is a direct bond, and is a substitutable number on A when m is 1 and A is not a hydrogen atom or a direct bond; and
provided that if X is a phosphorus atom or a sulfur atom, A is not a direct bond; and if X is a sulfur atom, A is not a hydrogen atom.

14 . The light-emitting electrochemical cell according to claim 13 , wherein a cation of the ionic compound is at least one selected from a phosphonium cation, an ammonium cation and an imidazolium cation.

15 . The light-emitting electrochemical cell according to claim 1

Assignees

• Nippon Chemical Ind

Inventors

• Yonekawa Fumihiro
• Mizuguchi Yohei

Classifications

• C08K5/42

  Sulfonic acids; Derivatives thereof · CPC title

• C07F5/022

  without C-boron linkages · CPC title

• C09K2211/1416

  Condensed systems · CPC title

• C08K5/521

  Esters of phosphoric acids, e.g. of H3PO4 · CPC title

• C07C69/78

  Benzoic acid esters · CPC title