Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-9871213-B2
Application number	US-201615186723-A
Country	US
Kind code	B2
Filing date	Jun 20, 2016
Priority date	May 3, 2005
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

The present invention relates to the use of aromatic boronic acid or borinic acid derivatives in organic electronic devices, in particular electroluminescent devices.

First claim

The invention claimed is:

1. A compound of formulae (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), or (26)

wherein said compounds of formulae (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), or (26) are optionally substituted by R 1 , wherein
B is a boron atom;
X is, identically or differently on each occurrence, OR 2 , SR 2 , N(R 2 ) 2 , NHR 2 , or OBAr 2 ;
Y is, identically or differently on each occurrence, Ar or X;
R 1 is, identically or differently on each occurrence, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkoxy chain having up to 40 C atoms optionally substituted by R 3 , or a branched or cyclic alkyl, alkoxy, or thioalkoxy chain having 3 to 40 C atoms, optionally substituted by R 3 , wherein one or more non-adjacent C atoms of said straight-chain, branched, or cyclic alkyl, alkoxy, or thioalkoxy chain is optionally replaced by N—R 3 , O, S, CO, O—CO—O, CO—O, —CR 3 ═CR 3 —, or —C≡C—and wherein one or more H atoms of said straight-chain, branched, or cyclic alkyl, alkoxy, or thioalkoxy chain is optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more R 3 , or a combination of two, three or four of these systems; and wherein two or more R 1 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
R 3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms.
Ar 1 is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, which may be substituted by R 1 ;
G is, identically or differently on each occurrence, C—H, C—R 1 , C—BXY, or N;
J is, identically or differently on each occurrence, C—H, C—R 1 , or C—BXY;
v is, identically or differently on each occurrence, 0 or 1;
R 2 is, identically or differently on each occurrence, a straight-chain alkyl chain having up to 40 C atoms optionally substituted by R 3 or a branched or cyclic alkyl chain having 3 to 40 C atoms optionally substituted by R 3 ; wherein one or more non-adjacent C atoms is optionally replaced by N—R 3 , O, S, CO, O—CO—O, CO—O, —CR 3 ═CR 3 —, or —C≡C—, with the proviso that a heteroatom is not bonded directly to the oxygen or sulfur or nitrogen of the group X or Y; and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 3 , or a combination of two, three or four of these systems; and wherein two or more radicals R 2 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;

with the proviso when X is OR 2 and Y is OR 2 in formulae (24) and (25), the two R 2 define an aromatic ring system, and with the proviso that the following compounds are excluded:

2. A compound of formulae (27), (27a), or (28)

wherein
B is a boron atom;
X is, identically or differently on each occurrence, OR 2 , SR 2 , N(R 2 ) 2 , NHR 2 , or OBAr 2 ;
Y is, identically or differently on each occurrence, Ar or X;
Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more R 1 ;
Ar 1 is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 40 aromatic ring atoms, which may be substituted by R 1 ;
R 1 is, identically or differently on each occurrence, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkoxy chain having up to 40 C atoms optionally substituted by R 3 , or a branched or cyclic alkyl, alkoxy, or thioalkoxy chain having 3 to 40 C atoms, optionally substituted by R 3 , wherein one or more non-adjacent C atoms of said straight-chain, branched, or cyclic alkyl, alkoxy, or thioalkoxy chain is optionally replaced by N—R 3 , O, S, CO, O—CO—O,CO—O, —CR 3 ═CR 3 —, or —C≡C—and wherein one or more H atoms of said straight-chain, branched, or cyclic alkyl, alkoxy, or thioalkoxy chain is optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more R 3 , or a combination of two, three or four of these systems; and wherein two or more R 1 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
R 3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms.
v is, identically or differently on each occurrence, 0 or 1;
Z is, identically or differently on each occurrence, O, S, NR 2 , or NH;
L is, identically or differently on each occurrence, an organic group having 4 to 60 C atoms, to which at least four groups Z are bonded in such a way that they are able, with the boron atom, to form a cyclic system;
R 2 is, identically or differently on each occurrence, a straight-chain alkyl chain having up to 40 C atoms optionally substituted by R 3 or a branched or cyclic alkyl chain having 3 to 40 C atoms optionally substituted by R 3 ; wherein one or more non-adjacent C atoms is optionally replaced by N—R 3 , O, S, CO, O—CO—O, CO—O, —CR 3 ═CR 3 —, or —C≡C—with the proviso that a heteroatom is not bonded directly to the oxygen or sulfur or nitrogen of the group X or Y; and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms optionally substituted by one or more radicals R 3 , or a combination of two, three or four of these systems; and wherein two or more radicals R 2 optionally define a mono- or polycyclic, aliphatic, or aromatic ring system;
Ar 2 is, identically or differently on each occurence, a fused aryl or heteroaryl group having 9 to 20 C atoms;
Ar 3 is, identically or differently on each occurence, a flourene or spirobiflourene group optionally substituted by R 1 ;
Q is, identically or differently on each occurrence, a divalent unit selected from Ar, O, S, SO, SO 2 , Se, SeO, SeO 2 , Te, TeO, TeO 2 , NAr, PAr, P(═O)Ar, AsAr, As(═O)Ar, SbAr, Sb(═O)Ar, C(R 1 ) 2 , C═O, Si(R 1 ) 2 , and O—BAr—O;
p is, identically or differently on each occurrence, 1, 2, 3, 4, 5, or 6;
is 0 or 1;
t is 1, 2, 3, 4, or 5;
w is, identically or differently on each occurrence, 1, 2, 3, 4, 5, or 6;

with the proviso that Ar 2 in formula (27) is not naphthyl on each occurrence if all p equal 1 and at the same time s equals 0 and t equals 1, and with the proviso that boronic acid esters of formula (28) formed with pinacol, 1,2-ethanediol, 2,2-dimethyl-1,3-propanediol, 2,3-butanediol, and isopropanol are excluded.

Assignees

• Merck Patent Gmbh

Inventors

• Stoessel Philipp
• Breuning Esther
• Buesing Arne
• Parham Amir Hossain
• Heil Holger
• Vestweber Horst

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07F9/46

  Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids {including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof} · CPC title

• C07F9/5325

  Aromatic phosphine oxides or thioxides (P-C aromatic linkage) · CPC title

• C09K2211/107

  with other heteroatoms · CPC title

• H01L51/5016

  Electricity · mapped topic