Materials for organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-11760734-B2
Application number	US-202117222671-A
Country	US
Kind code	B2
Filing date	Apr 5, 2021
Priority date	Nov 17, 2009
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

The present invention relates to fluorene derivatives and to electronic devices in which these compounds are used as matrix material in the emitting layer and/or as hole-transport material and/or as electron-blocking or exciton-blocking material and/or as electron-transport material.

First claim

The invention claimed is:

1. A mixture comprising at least one compound of the formula (1) and at least one further compound

where
Y is C(R 1 ) 2 , O or NR 3 ;
X is on each occurrence, identically or differently, CR 1 or N, where a maximum of three groups X in each ring stand for N;
A is on each occurrence, identically or differently, CR 2 or N, where a maximum of three groups A in each ring stand for N;
R 1 , R 2 are on each occurrence, identically or differently, H, D, Cl, Br, I, F, CN, NO 2 , N(R 4 ) 3 , Si(R 4 ) 3 , B(OR 4 ) 2 , C(═O)R 4 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , —CR 4 ═CR 4 —, OSO 2 R 4 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R 4 , where one or more non-adjacent CH 2 groups may be replaced by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or 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 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 4 , or aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 4 ; two or more adjacent substituents R 1 together with the atoms to which they are bonded or two or more adjacent substituents R 2 together with the atoms to which they are bonded may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
characterised in that at least one R 1 which is bonded to X stands for triazine, which may be substituted by one or more radicals R 4 ,
or in that at least one R 2 stands for a 6-membered heteroaromatic group, which may be substituted by one or more radicals R 4 , and at least one radical R 1 simultaneously stands for an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 4 ;

R 3 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R 4 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 3 , or a combination of these systems;
R 4 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, NO 2 , N(R 5 ) 3 , Si(R 5 ) 3 , B(OR 5 ) 2 , C(═O)R 5 , P(═O)(R 5 ) 2 , S(═O)R 5 , S(═O) 2 R 5 , —CR 5 ═CR 5 —, OSO 2 R 5 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which may be substituted by one or more radicals R 5 , where one or more non-adjacent CH 2 groups may 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, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or 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 5 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 5 , or aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 5 ; two or more radicals R 4 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another together with the atoms to which they are bonded;
R 5 is on each occurrence, identically or differently, an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms; two or more radicals R 5 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another together with the atoms to which they are bonded.

2. The Mixture according to claim 1 , wherein the compound of formula (1) is selected from a compound of the formula (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14) or (15):

where the symbols and indices used have the meanings indicated in claim 1 .

3. The mixture according to claim 1 , wherein, if at least one group R 1 stands for triazine, this is 1,3,5-triazine or 1,2,4-triazine, which may in each case be substituted by one or more radicals R 4 and where the radicals R 4 which are not equal to hydrogen or deuterium preferably stand for an aromatic or heteroaromatic ring system; or in that, if at least one group R 2 stands for a 6-membered heteroaromatic group, this is selected from triazine, pyrimidine, pyrazine, pyridazine or pyridine, each of which may be substituted by one or more radicals R 4 and where the radicals R 4 which are not equal to hydrogen or deuterium preferably stand for an aromatic or heteroaromatic ring system.

4. The mixture according to claim 1 , wherein the triazine substituents R 1 and R 2 and the pyrimidine substituents R 2 are selected from the groups depicted below:

where the dashed bond indicates the link from this group to the skeleton.

5. The mixture according to claim 1 , wherein the compound of formula (1) is a compound of the formula (16) or (17):

6. The mixture according to claim 1 , wherein the compound of formula (1) is selected from compounds of the formulae (20), (21), (24) or (25):

7. The mixture according to claim 1 , wherein the compound of formula (1) is a compound of formulae (29) or (31):

8. The mixture according to claim 1 , wherein the at least one further material is a matrix material.

9. The mixture according to claim 8 , wherein the matrix material is a hole transport material.

10. The mixture according to claim 1 further comprising a phosphorescent or fluorescent compound.

11. A formulation comprising at least one mixture according to claim 1 and one or more solvent.

12. An electronic devices comprising at least one mixture according to claim 1 , where the electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-L

Assignees

• Merck Patent Gmbh

Inventors

• Franz Adam W
• Anémian Rémi Manouk

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• C07D251/24 Primary

  to three ring carbon atoms · CPC title

• C07D251/16

  to only one ring carbon atom · CPC title

• C07D251/22

  to two ring carbon atoms · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title