Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-10577342-B2
Application number	US-201515524389-A
Country	US
Kind code	B2
Filing date	Oct 13, 2015
Priority date	Nov 11, 2014
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

The 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 organic electroluminescent device comprising at least one compound of formula (1) used as matrix material for a fluorescent or phosphorescent compound in an emitting layer and/or in an electron blocker layer

where the symbols and indices used are as follows:
Ar 1 are the same or different at each instance and are an aromatic or heteroaromatic ring system which has 6 to 60 aromatic ring atoms and may in each case also be substituted by one or more R 2 radicals, where, in the case that q>0, at least the two Ar 1 may be joined and/or Ar 1 may be joined to Ar 2 via at least one bridge K;
K is the same or different at each instance and is a single bond or a bivalent bridge selected from N(R 2 ), B(R 2 ), O, C═O, C(R 2 ) 2 , Si(R 2 ) 2 , and S;
Ar 2 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals;
X is the same or different at each instance and is N or CR 1 ;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, CHO, C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, P(═O)(R 2 ), SO, SO 2 , O, S or CONR 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or a combination of these systems; at the same time, two or more adjacent R 1 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 6 to 60 aromatic ring atoms and may in each case also be substituted by one or more R 2 radicals;
R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, CHO, C(═O)R 3 , P(═O) (R 3 ) 2 , S(═O) R 3 , S(═O) 2 R 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 3 radicals, where one or more nonadjacent CH 2 groups may be replaced by C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, P(═O)(R 3 ), SO, SO 2 , O, S or CONR 3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals, or a combination of these systems; at the same time, two or more adjacent R 2 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
R 3 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R 4 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O) 2 Ar, CR 4 ═CR 4 Ar, CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , C═O, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 4 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or a combination of these systems; at the same time, two or more adjacent R 3 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
R 4 is the same or different at each instance and is H, D, F or an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aryl or heteroaryl group which has 5 to 40 ring atoms and may be substituted by one or more R 5 radicals, or a combination of these groups;
R 5 is the same or different at each instance and is H, D, F or an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms;
q is 0, 1 or 2;
where
Ar 2 in the case of a heteroaromatic ring system may be joined to the phenanthridine base skeleton via a C—C bond; and,
R 1 in the case of a heteroaromatic ring system may be joined to the phenanthridine base skeleton via a C—C bond.

2. The device according to claim 1 , wherein the compound is of formula (2)

where the symbols and indices have the definitions given in claim 1 .

3. The device according to claim 2 , wherein the compound isone of the formulae (3) to (8):

where the symbols and indices have the definitions given in claim 2 and, in addition, the two Ar 1 are not joined to one another and Ar 1 is not joined to Ar 2 by further K groups and, in the formulae (4), (5), (6), (7) and (8), q>0.

4. A mixture comprising at least one compound of formula (1)

where the symbols and indices used are as follows:
Ar 1 are the same or different at each instance and are an aromatic or heteroaromatic ring system which has 6 to 60 aromatic ring atoms and may in each case also be substituted by one or more R 2 radicals, where, in the case that q>0, at least the two Ar 1 may be joined and/or Ar 1 may be joined to Ar 2 via at least one bridge K;
K is the same or different at each instance and is a single bond or a bivalent bridge selected from N(R 2 ), B(R 2 ), O, C═O, C(R 2 ) 2 , Si(R 2 ) 2 , and S;
Ar 2 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals;
X is the same or different at each instance and is N or CR 1 ;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, CHO, C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 ,

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Stoessel Philipp
• Eberle Thomas
• Jatsch Anja
• Kroeber Jonas Valentin
• Pflumm Christof

Classifications

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D487/06

  Peri-condensed systems · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D491/107

  with only one oxygen atom as ring hetero atom in the oxygen-containing ring · CPC title

• C07D405/14 Primary

  containing three or more hetero rings · CPC title