Materials for organic light emitting devices

Patent metadata

Field	Value
Publication number	US-11895913-B2
Application number	US-202217994035-A
Country	US
Kind code	B2
Filing date	Nov 25, 2022
Priority date	May 5, 2014
Publication date	Feb 6, 2024
Grant date	Feb 6, 2024

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 mixture comprising at least one compound of the formula (2a),

where the following applies to the symbols and indices used:
A is on each occurrence, identically or differently, CR or N, where a maximum of two groups A per ring stand for N and where A stands for C if the group comprising Y 2 is bonded at this position;
W is on each occurrence, identically or differently, CR or N, where a maximum of two groups W stand for N, or two adjacent groups W together stand for a group of the following formula (3), where the compound of the formula (1a) contains a maximum of one group of the formula (3),

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 , Y 2 , Y 3 are on each occurrence, identically or differently, O, NR, S or CR 2 , where the radical R which is bonded to N is not equal to H;
L is on each occurrence, identically or differently, a single bond or an aromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R;
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) 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, 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′, 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′), C(R 1 ) 2 , O or S;
m is 0, 1, 2 or 3;
R 1 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having t 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 carbatoms; two or more adjacent substituents R 1 may form a mono- or polycyclic, aliphatic ring system with one another here;
and at least one further compound, wherein the further compound is a matrix material and wherein the matrix material is a hole-transporting compound.

2. The mixture according to claim 1 , wherein X is on each occurrence N.

3. The mixture according to claim 1 , wherein Y 1 is O.

4. The mixture according to claim 1 , wherein Y 1 is S.

5. The mixture according to claim 1 , wherein Y 1 is NR.

6. The mixture according to claim 1 , wherein Y 1 is CR 2 .

7. The mixture according to claim 1 , wherein the hole transporting compound is a carbazole derivative.

8. The mixture according to claim 7 , wherein the carbazole derivative is a biscarbazole.

9. The mixture according to claim 1 , wherein the compound of formula (2a) is selected from the group of compounds:

10. An organic electroluminescent device comprising the mixture according to claim 1 .

11. An organic electroluminescent device comprising the mixture according to claim 8 .

12. An organic electroluminescent device comprising the mixture according to claim 9 .

13. An organic electroluminescent device comprising the mixture according to claim 1 wherein the mixture is employed in an emitting layer, in combination with a phosphorescent dopant.

14. An organic electroluminescent device comprising the mixture according to claim 8 wherein the mixture is employed in an emitting layer, in combination with a phosphorescent dopant.

15. An organic electroluminescent device comprising the mixture according g to claim 9 wherein the mixture is employed in an emitting layer, in combination with a phosphorescent dopant.

16. A mixture comprising at least one compound of the formula (2a),

where the following applies to the symbols and indices used:
A is on each occurrence, identically or differently, CR or N, where a maximum of two groups A per ring stand for N and where A stands for C if the group comprising Y 2 is bonded at this position;
W is on each occurrence, identically or differently, CR or N, where a maximum of two groups W stand for N, or two adjacent groups W together stand for a group of the following formula (3), where the compound of the formula (1a) contains a maximum of one group of the formula (3),

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 NR, S or CR 2 , where the radical R which is bonded to N is not equal to H;
Y 2 , Y 3 are on each occurrence, identically or differently, O, NR, S or CR 2 , where the radical R which is bonded to N is not equal to H;
L is on each occurrence, identically or differently, a single bond or an aromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted

Assignees

• Merck Patent Gmbh

Inventors

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

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K85/654 Primary

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• C07D403/14 Primary

  containing three or more hetero rings · CPC title

• C07D251/24

  to three ring carbon atoms · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title