Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11639339-B2
Application number	US-201816766424-A
Country	US
Kind code	B2
Filing date	Nov 22, 2018
Priority date	Nov 24, 2017
Publication date	May 2, 2023
Grant date	May 2, 2023

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 comprise 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 4 stands for a group of formula (Ar4-1),

 where the dashed bond in formula (Ar4-1) indicates the bonding to the structure of formula (1);
G is a condensed aryl group having 10 to 50 aromatic ring atoms, which can in each case be substituted by one or more radicals R 2 ;
Ar 1 , Ar 2 and Ar 3 stand on each occurrence, identically or differently, for Ar 4 , or for an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can in each case be substituted by one or more radicals R 3 ;
Ar S is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which can in each case also be substituted by one or more radicals R 3 ;
Ar 5 , Ar 6 stand on each occurrence, identically or differently, for an aryl or heteroaryl group having 5 to 18 aromatic ring atoms, which can in each case be substituted by one or more radicals R 4 ;
X stands for CR 1 or nitrogen; or X stands for carbon, if it is bonded to Ar 5 , Ar 6 , R 4 or to an adjacent fluorene derivative unit;
R, R 0 , R 1 , R 2 , R 3 , R 4 stand on each occurrence, identically or differently, for hydrogen, deuterium, fluorine, chlorine, bromine, iodine, CHO, C≡N, N(Ar 7 ) 2 , C(═O)Ar 7 , P(═O)(Ar 7 ) 2 , S(═O)Ar 7 , S(═O) 2 Ar 7 , NO 2 , Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 carbon atoms or branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 carbon atoms, each of which can be substituted by one or more radicals R 5 , where in each case one or more non-adjacent CH 2 groups can be replaced by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, P(═O)(R 5 ), SO, SO 2 , O, S or CONR 5 and where one or more H atoms can be replaced by deuterium, fluorine, chlorine, bromine, iodine, CN or NO 2 , an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which can in each case be substituted by one or more radicals R 5 , or an aryloxy groups having 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R 5 , where two adjacent substituents R, two adjacent substituents R 0 , two adjacent substituents R 1 , two adjacent substituents R 2 , two adjacent substituents R 3 and/or two adjacent substituents R 4 , can form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which can be substituted by one or more radicals R 5 ;
R 5 stands on each occurrence, identically or differently, for hydrogen, deuterium, fluorine, chlorine, bromine, iodine, CHO, C≡N, N(Ar 7 ) 2 , C(═O)Ar 7 , P(═O)(Ar 7 ) 2 , S(═O)Ar 7 , S(═O) 2 Ar 7 , NO 2 , Si(R 6 ) 3 , B(OR 6 ) 2 , OSO 2 R 6 , a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 carbon atoms, each of which can be substituted by one or more radicals R 6 , where in each case one or more non-adjacent CH 2 groups can be replaced by R 6 C═CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C═O, C═S, C═Se, P(═O)(R 6 ), SO, SO 2 , O, S or CONR 6 and where one or more hydrogen atoms can be replaced by deuterium, fluorine, chlorine, bromine, iodine, CN or NO 2 , an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which can in each case be substituted by one or more radicals R 6 , or an aryloxy group having 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R 6 , where two adjacent substituents R 5 can form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which can be substituted by one or more radicals R 6 ;
Ar 7 is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can in each case also be substituted by one or more radicals R 6 ;
R 6 stands on each occurrence, identically or differently, for hydrogen, deuterium, fluorine, chlorine, bromine, iodine, C≡N, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 20 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 carbon atoms, where in each case one or more non-adjacent CH 2 groups can be replaced by SO, SO 2 , O, S and where one or more hydrogen atoms can be replaced by deuterium, fluorine, chlorine, bromine or iodine, or an aromatic or heteroaromatic ring system having 5 to 24 carbon atoms;
n is equal to 0 or 1;
r is equal to 0, 1 or 2;
m, q are, identically or differently, an integer selected from 1 to 10;
p, s are on each occurrence, identically or differently, an integer selected from 0 to 10;
with the proviso that, if the group G is a pyrene group, then the compound of formula (1) bears at least one group R, R 0 , R 2 or R 3 , which stands for a straight-chain alkyl group having 3 to 40 carbon atoms or a branched or cyclic alkyl group having 3 to 40 carbon atoms, each of which can be substituted by one or more radicals R 6 .

2. The compound according to claim 1 , wherein s is an integer selected from 1 to 10.

3. The compound according to claim 1 , selected from compounds of formulae (2) to (5),

where the symbols and indices have the same meaning as in claim 1 .

4. The compound according to claim 1 , wherein Ar 5 and Ar 6 are selected, identically or differently, from the group consisting of the groups of formulae (Ar5-1) to (Ar5-26),

where
the dashed bonds indicate the bonding to the adjacent groups as depicted in formula (1);
the groups of formulae (Ar5-1) to (Ar5-26) can be substituted at each free position by a group R 4 , which has the same meaning as in claim 1 ; and
E 1 is selected from —B(R 0 —), —C(R 0 ) 2 —, —C(R 0 ) 2 —C(R 0 ) 2 —, —Si(R 0 ) 2 —, —C(═O)—, —C(═NR 0 )—, —C═(C(R 0 )) 2 —, —O—, —S—, —S(═O)—, —SO 2 —, —N(R 0 )—, —P(R 0 )—, and —P((═O)R 0 —, where the substituent R 0 has the same meaning as in claim 1 .

5. The compound according to claim 1 , wherein Ar 5 and Ar 6 are selected, identically or differently, from the group consisting of the groups of formulae (Ar5-27) to (Ar5-35),

where
the dashed bonds indicate the bonding to the adjacent groups depicted in formula (1);
the groups of formulae (Ar5-27) to (Ar5-35) can be substituted at each free position by a group R 4 , which has the same meaning as in claim 1 ; and the substituent E 1 in formulae (Ar5-28) to (Ar5-30) is selected from —B(R 0 —), —C(R 0 ) 2 —, —C(R 0 ) 2 —C(R 0 ) 2 —, —Si(R 0 ) 2 —, —C(═O)—, —C(═NR 0 )—, —C═(C(R 0 )) 2 —, —O—, —S—, —S(═O)—, —SO 2 —, —N(R 0 )—, —P(R 0 )— and —P((═O)R 0 )—.

6. The compound according to claim 1 , wherein the group Ar 4 is selected from the groups of formula (Ar4-2) to (Ar4-6),

Assignees

• Merck Patent Gmbh

Inventors

• Koenen Nils
• Linge Rouven
• Meyer Sebastian
• Heil Holger

Classifications

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C07C211/54 Primary

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• H10K85/633

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

• C07D493/20

  Spiro-condensed systems · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title