Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-9496504-B2
Application number	US-201013521266-A
Country	US
Kind code	B2
Filing date	Dec 17, 2010
Priority date	Jan 16, 2010
Publication date	Nov 15, 2016
Grant date	Nov 15, 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, and to electronic devices which contain these compounds.

First claim

The invention claimed is:

1. A compound of the formula (1),

where the following applies to the symbols and indices used:
Ar 1 and Ar 2 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R; Ar 1 and Ar 2 here may also be connected to one another by a single bond and thus form a carbazole;
Ar 3 and Ar 4 is on each occurrence, identically or differently, a divalent aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R, with the proviso that Ar 3 and Ar 4 do not contain any aryl groups having more than two aromatic six-membered rings condensed directly onto one another;
Ar 5 is selected from a group of formulae (3), (4), or (6),

Ar 6 is selected from any one group of formulae (3) to (15),

where the dashed bond indicates the position of the bond from the group to the nitrogen;
L is a divalent 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, which is optionally substituted in each case by one or more radicals R, where one or more CH 2 groups, is optionally replaced by Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C═O, C═S, C═Se, C═NR, P(═O)R, S═O, SO 2 , —O—, —S— or —CONR— and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a divalent aromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R, where L does not contain any aryl groups having more than two sequentially condensed aromatic six-membered rings, or L is Si(R) 2 , Ge(R) 2 , O, S, C(═O), S(═O), SO 2 , SF 4 , PR, P(═O)(R), PF 3 , P(═S)(R), AsR, As(═O)(R), As(═S)(R), Sb, Sb(═O)(R), Sb(═S)(R), N(Ar) or L is a combination of two, three, four or five of these systems;
R is on each occurrence, identically or differently, a H, D, F, Cl, Br, I, CN, NO 2 , N(Ar) 2 , N(R 1 ) 2 , C(═O)Ar, C(═O)R 1 , P(═O)(Ar) 2 , B(R 1 ) 2 , B(OR 1 ) 2 , Si(R 1 ) 3 , 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 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 60 aromatic ring atoms, which may 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 an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , where two or more adjacent substituents R may optionally form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R 1 ;
R 1 is on each occurrence, identically or differently, a 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 , B(R 2 ) 2 , B(OR 2 ) 2 , Si(R 2 ) 3 , 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 may 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 an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , where two or more adjacent substituents R 1 may optionally form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R 2 ;
Ar 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 which are bonded to the same N atom or P atom may also be bridged to one another by a single bond or a bridge selected from N(R 2 ), C(R 2 ) 2 , O or S;
R 2 is a 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;
m and n are on each occurrence, identically or differently, 0 or 1, where m=n=1 if L stands for O, S or N(Ar).

2. The compound according to claim 1 , wherein
L is a divalent 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, which is optionally substituted in each case by one or more radicals R, where one or more CH 2 groups, which are not adjacent, is optionally replaced by Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C═O, C═S, C═Se, C═NR, P(═O)R, S═O, SO 2 , —O—, —S— or —CONR— and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a divalent aromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R, where L does not contain any aryl groups having more than two sequentially condensed aromatic six-membered rings, or L is Si(R) 2 , Ge(R) 2 , O, S, C(═O), S(═O), SO 2 , SF 4 , PR, P(═O)(R), PF 3 , P(═S)(R), AsR, As(═O)(R), As(═S)(R), Sb, Sb(═O)(R), Sb(═S)(R), N(Ar) or L is a combination of two, three, four or five of these systems.

3. The compound according to claim 1 , wherein Ar 6 is selected from formulae (12), (13), or (14).

4. The compound according to claim 1 , wherein Ar 6 is selected from any one of formulae (3) to (11).

5. The compound according to claim 1 , wherein the unit —NAr 5 Ar 6 is selected from any one group of formulae (16) to (20), (22), (24), or (25);

where the symbols used have the meanings given in claim 1 , and the dashed bond indicates the bond from this group to L or Ar 4 .

Assignees

• Pan Junyou
• Buchholz Herwig
• Mujica-Fernaud Teresa
• Martynova Irina
• Merck Patent Gmbh

Inventors

• Pan Junyou
• Buchholz Herwig
• Mujica-Fernaud Teresa
• Martynova Irina

Classifications

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• H01L51/0059

  Electricity · mapped topic

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B69/109

  containing other specific dyes · CPC title