Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9356243-B2
Application number	US-201414454142-A
Country	US
Kind code	B2
Filing date	Aug 7, 2014
Priority date	Mar 25, 2010
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

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

First claim

The invention claimed is:

1. An electronic device comprising a compound of the formula (1)

where the following applies to the symbols and indices used:
X is C═O, C(R) 2 , O, S, C═S, SO or SO 2 ;
Y is C;
W is on each occurrence, identically or differently, CR or N, with the proviso that not more than three groups W in a ring stand for N, and with the further proviso that W═C if a group E is bonded to this group W;
Z is, identically or differently on each occurrence, CR or N; or two adjacent groups Z stand for a group of the formula (2)

in which the dashed bonds indicate the linking of this unit;

E is, identically or differently on each occurrence, a single bond, C(R) 2 , NR, O, S, C═O, C═S, C═NR, C═C(R) 2 , Si(R) 2 , BR, PR, P(═O)R, SO or SO 2 ;

Ar is a group of one of the following formulae (7), (8), (9) or (10):

wherein the dashed bond indicates the link to N, # indicates the position of the link to X, * indicates the position of the link to E if a group E is present, and W and V stands for NR, O or S, wherein W is equal to C if a group E is bonded at this position; and wherein a maximum of one symbol W per ring stands for N and the remaining symbols W per ring stand for CR;
A is R if m=n=0, and is an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may in each case be substituted by R, or a group —CR═CR—, —CR═N— or —N═N— if an index m or n=1 and the other index m or n=0, or is an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may in each case be substituted by R, if the indices m=n=1;
R is selected on each occurrence, identically or differently, from H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , a straight-chain alkyl or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups is optionally replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , O, S or CONR 1 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 80 aromatic ring atoms, which is optionally in each case be substituted by one or more radicals R 1 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 , or a combination of these systems, where two or more adjacent substituents R may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R 1 ;
R 1 is selected on each occurrence, identically or differently, is H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 2 ) 2 , C(═O)Ar, C(═O)R 2 , P(═O)(Ar 1 ) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or 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, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is 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 where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally in each case be substituted by one or more radicals R 2 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or a combination of these systems, where two or more adjacent substituents R may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R 2 ;
R 2 is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R 2 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R 2 ; two radicals Ar 1 which are bonded to the same N atom or P atom may also be bridged to one another here by a single bond or a bridge selected from N(R 2 ), C(R 2 ) 2 or O;
m is 0;
n is 0 or 1, where, for n=0, a group R instead of the group E is bonded to A;
p is 1;
wherein said heteroaryl groups and heteroaromatic ring systems contain at least one heteroatom selected from the group consisting of N, O, and S.

2. The electronic device according to claim 1 , wherein in the compound of the formula (1) E stands, identically or differently on each occurrence, for a single bond, CR 2 , C═O, NR, O or S.

3. The electronic device according to claim 1 , wherein in the compound of the formula (1) A stands for a group of one of the following formulae (3), (4), (5) or (6):

where the dashed bond indicates the link to N, * indicates the position of the link E if a group E is present, W has the meaning given in claim 1 , and W is equal to C if a group E is bonded at this position, and V stands for NR, O or S.

4. The electronic device according to claim 1 , wherein in the compound of the formula (1) the following applies to the symbols and indices used:
X is C═O, CR 2 , S, O or SO 2 ;
E is, identically or differently on each occurrence, a single bond, CR 2 , C═O, NR, O or S;
A is an aryl or heteroaryl group having 5 to 16 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or a group —CR═CR—, —CR═N— or —N═N—;
Z═Z in the five-membered ring stands for a group of the formula (2) defined in claim 1 ;
Ar stands for a group of one of the following formulae (7) to (10):

where the dashed bond indicates the link to N, # indicates the position of the link to X, * indicates the position of the link to E if a group E is present, and W has the meaning given in claim 1 ; W here is equal to C if a group E is bonded at this position; furthermore, V stands for NR, O, S or CR 2 ;

m is 0; and
n is 1.

5. The electronic device according to claim 1 , wherein the compound of the formula (1) is selected from the compounds of the following formulae (11) to (37):

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Pflumm Christof
• Mujica-Fernaud Teresa

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D471/22 Primary

  in which the condensed systems contains four or more hetero rings · CPC title

• C07D487/16

  Peri-condensed systems · CPC title

• H01L51/5072

  Electricity · mapped topic