Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9620722-B2
Application number	US-201214112431-A
Country	US
Kind code	B2
Filing date	Mar 26, 2012
Priority date	Apr 18, 2011
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

The present invention relates to compounds of the formula (1) and formula (2), which are suitable for use in electronic devices, in particular in organic electroluminescent devices.

First claim

The invention claimed is:

1. A compound of formula (1) or formula (2),

wherein
X is, identically or differently on each occurrence, N, P, or P═O;
Y1 is, identically or differently on each occurrence, C(R 1 ) 2 or NR 1 ;
Y 2 , Y 3 is, identically or differently on each occurrence, a single bond or C(R 1 ) 2 , NR 1 , O, S, C═O, C═NR 1 , C═C(R 1 ) 2 , Si(R 1 ) 2 , BR 1 , PR 1 , P(═O)R 1 , SO, or SO 2 ; with the proviso that if any one of Y 1 , Y 2 or Y 3 is NR 1 , then R 1 of NR 1 is an aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R 2 ;
Ar 1 is, identically or differently on each occurrence, a group of the following formula (3), formula (4), or formula (5),

wherein the group is bonded to X and to Y 1 via the two positions denoted by * and wherein the group is optionally bonded to Y 3 via a further adjacent position and wherein
W is, identically or differently on each occurrence, C or N;
V for W═C, is, identically or differently on each occurrence, CR, N, NR, S, or O, with the proviso that precisely one symbol V stands for NR, S, or O; or, for W═N is, identically or differently on each occurrence, CR or N;
Q is on each occurrence, identically or differently; CR or N;

wherein V or Q stands for C if a group Y 3 is bonded to this group V or Q;
Ar 2 , Ar 3 is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 18 aromatic ring atoms, optionally substituted by one or more radicals R;
L is a di-, tri-, tetra-, penta- or hexavalent straight-chain alkylene, alkylidene, alkyleneoxy, or thioalkyleneoxy group having 1 to 40 C atoms, or a branched or cyclic alkylene, alkylidene, alkyleneoxy, or thioalkyleneoxy group having 3 to 40 C atoms, or an alkenylene or alkynylene group having 2 to 40 C atoms, optionally substituted by in each case one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═NR 2 , P(═O)R 2 , S═O, SO 2 , —O—, —S—, or —CONR 2 —, and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , or a di-, tri-, tetra-, penta- or hexavalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, optionally substituted by one or more radicals R 2 , or P(R 2 ) 3-p , P(═O)(R 2 ) 3-p , C(R 2 ) 4-p , Si(R 2 ) 4-p , N(Ar) 3-p , or a combination of two, three, four, or five of these systems; or L is a chemical bond; L is bonded to any desired position of Ar 1 , Ar 2 , Ar 3 , Y 1 , Y 2 or Y 3 instead of a radical R or R 1 ;
R, R 1 is, identically or differently on each occurrence, selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar) 2 , N(R 2 ) 2 , C(═O)Ar, C(═O)R 2 , P(═O)(Ar) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, and an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S, or CONR 2 , and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, NO 2 , an aromatic or heteroaromatic ring system having 5 to 80, aromatic ring atoms, optionally substituted by one or more radicals R 2 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 2 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 2 , wherein two or more adjacent substituents R or two substituents R 1 which are bonded in the same group Y optionally define a mono- or polycyclic, aliphatic, aromatic, or heteroaromatic ring system, optionally substituted by one or more radicals R 2 ;
R 2 is, identically or differently on each occurrence, selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar) 2 , N(R 3 ) 2 , C(═O)Ar, C(═O)R 3 , P(═O)(Ar) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, optionally substituted by one or more radicals R 3 , wherein one or more non-adjacent CH 2 groups are optionally replaced by R 3 C═CR 3 , C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(O)(R 3 ), SO, SO 2 , NR 3 , O, S, or CONR 3 , and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, wherein two or more adjacent substituents R 2 optionally define a monocyclic or polycyclic, aliphatic, aromatic, or heteroaromatic ring system, optionally substituted by one or more radicals R 3 ;
Ar is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, optionally substituted by one or more non-aromatic radicals R 3 ; two radicals Ar which are bonded to the same N atom or P atom are optionally bridged to one another by a single bond or a bridge selected from N(R 3 ), C(R 3 ) 2 , O, or S;
R 3 is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, and an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms are optionally replaced by D, F, Cl, Br, I, or CN, wherein two or more adjacent substituents R 3 optionally define a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system;
m, n are, identically or differently on each occurrence, 0 or 1, wherein m=0 or n=0 means that no group Y is present;
p is 2, 3, 4, 5, or 6, with the proviso that p is not greater than the maximum valence of L;
wherein the following compounds are excluded from the invention:

2. The compound of claim 1 , wherein Ar 2 and Ar 3 are, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 10 aromatic ring atoms, optionally substituted by one or more radicals R.

3. The compound of claim 1 , wherein the compound is selected from the compounds of formulae (5) to (11):

wherein
A is, identically or differently on each occurrence, CR or N; or two adjacent groups A together stand for NR, O or S, so that a five-membered ring arises; A is C if a group Y 2 or Y 3 is bonded to this A;
or selected from two or more compounds of the formulae (5) to (11), identical or different on each occurrence, connected to one another via L.

4. The compound of claim 1 , wherein the compound is selected from the compounds of formulae (5a) to (11a),

Assignees

• Martynova Irina
• Pflumm Christof
• Parham Amir Hossain
• Anémian Rémi Manouk
• Mujica-Fernaud Teresa
• De Nonancourt Claire
• Merck Patent Gmbh

Inventors

• Martynova Irina
• Pflumm Christof
• Parham Amir Hossain
• Anémian Rémi Manouk
• Mujica-Fernaud Teresa
• De Nonancourt Claire

Classifications

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• H01L51/5016

  Electricity · mapped topic