Materials for organic light emitting devices

Patent metadata

Field	Value
Publication number	US-12329026-B2
Application number	US-202418444810-A
Country	US
Kind code	B2
Filing date	Feb 19, 2024
Priority date	May 5, 2014
Publication date	Jun 10, 2025
Grant date	Jun 10, 2025

Abstract

The present invention describes carbazole, dibenzofuran, dibenzothiophene and fluorene derivatives which are substituted by electron-deficient heteroaryl groups, in particular for use as triplet matrix materials in organic electroluminescent devices. The invention furthermore relates to a process for the preparation of the compounds according to the invention and to electronic devices comprising these compounds.

First claim

The invention claimed is:

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

where the following applies to the symbols and indices used:
X is on each occurrence, identically or differently, CR or N, with the proviso that at least one group X stands for N;
Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R;
Y 1 is O or S
Y 2 is NR′;
R′ is a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R 1 , or is a phenylene group which is substituted with a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R 1 ;
L is a single bond;
R is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 1 ) 2 , C(═O)Ar 1 , C(═O)R 1 , P(═O)(Ar 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , Si(Ar 1 ) 3 , Si(R 1 ) 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms or an alkenyl group having 2 to 20 C atoms, each of which may be substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups may be replaced by R 1 C═CR 1 , Si(R 1 ) 2 , C═O, C═S, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , O, S or CONR 1 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 40 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 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 ; two substituents R which are bonded to the same carbon atom or to adjacent carbon atoms may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system here, which may be substituted by one or more radicals R 1 ;
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 1 ; two radicals Ar 1 which are bonded to the same N atom, P atom or B atom may also be bridged to one another here by a single bond or a bridge selected from N(R 1 ), C(R 1 ) 2 , O or S;
R 1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups, each having 1 to 4 carbon atoms; two or more adjacent substituents R 1 may form a mono- or polycyclic, aliphatic ring system with one another here.

2. The compound according to claim 1 , for which:
X is N;
Y 1 is O;
Y 2 is NR′;
R′ is a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R 1 , or is a phenylene group which is substituted with a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R 1 ; wherein the groups R 1 are selected from H, D or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms;
Ar stands, identically or differently on each occurrence, for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may be substituted by one or more radicals R;
n is, identically or differently on each occurrence, 0, 1, 2 or 3;
m is, identically or differently on each occurrence, 0, 1 or 2;
R is selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms or an alkenyl group having 2 to 10 C atoms, each of which may be substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups may be replaced by O and where one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 25 aromatic ring atoms, which may be substituted by one or more radicals R 1 ; two substituents R which are bonded to the same carbon atom or to adjacent carbon atoms may optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system here, which may be substituted by one or more radicals R 1 ;
the other symbols have the meanings as defined in claim 1 .

3. The compound according to claim 1 , for which:
X is N;
Y 1 is O;
Y 2 is NR′;
R′ is a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R 1 , or is a phenylene group which is substituted with a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R 1 ; wherein the groups R 1 are selected from H, D or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms;
Ar stands, identically or differently on each occurrence, for an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms;
n is on each occurrence, identically or differently, 0 or 1;
m is 0;
R is selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, N(Ar 1 ) 2 , a straight-chain alkyl group having 1 to 8 C atoms, a branched or cyclic alkyl group having 3 to 8 C atoms or an alkenyl group having 2 to 8 C atoms, each of which may be substituted by one or more radicals R 1 , or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R 1 ; two substituents R which are bonded to the same carbon atom or to adjacent carbon atoms may optionally form a monocyclic or polycyclic, aliphatic ring system here, which may be substituted by one or more radicals R 1 ;
the other symbols have the meanings as defined in claim 1 .

4. The compound according to claim 1 of the formula (8c),

where the following applies to the symbols and indices used:
Y 1 is O;
Y 2 is NR′;
R′ is a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R 1 , or is a phenylene group which is substituted with a 1,3,5-triazine group or a pyrimidine group, each of which may be substituted by one or more radicals R 1 ; wherein the groups R 1 are selected from H, D or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms;
Ar stands, identically or differently on each occurrence, for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R;
n is, identically or differently on each occurrence, 0, 1, 2 or 3;
m is, identically or differently on each occurrence, 0, 1 or 2;
R is selected, identically or differently on each occurrence, from the group consisting of H, D, F, CN, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched o

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Jatsch Anja
• Eberle Thomas
• Grossmann Tobias
• Kroeber Jonas Valentin
• Dobelmann-Mara Lars

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title