Materials for organic electroluminescent devices
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.
1. A mixture comprising at least one compound of the formula (1) and at least one further compound
where the following applies to the symbols and indices used:
Y is CO, S, SO, SO 2 , PR 3 or P(O)R 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 selected from the following compounds of the formula (16) or (17):
where the symbols used have the meanings indicated in claim 1 .
6. The mixture according to claim 1 , wherein the compound of formula (1) is selected from the following compounds of the formulae (18) to (27):
where the symbols used have the meanings indicated in claim 1 .
7. The mixture according to claim 1 , wherein the compound of formula (1) is selected from the following compounds of the formulae (28) to (34):
where the symbols and indices used have the meanings indicated in claim 1 .
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-LETs), organic integrated circuits (O-ICs), organic solar cells (O-SCs), organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and organic photoreceptors.
13. The electronic device of claim 12 , wherein the device is an organic electroluminescent device.