Materials for organic electroluminescent devices
The present invention relates to substituted benz[a]anthracene derivatives, to the preparation and use thereof in organic electroluminescent devices, and to organic electroluminescent devices, in particular blue-emitting devices, in which these compounds are used as matrix material or dopant in the emitting layer and/or as hole-transport material and/or as electron-transport material.
1. A compound of the formula (9) or (10),
where the dashes drawn as nonspecific bonds are intended to denote that the group X is bonded, in each case independently of one another, via one of positions 8 or 11 of the respective benz[a]anthracene, where the following applies to the symbols and indices:
X is selected from the units of the following formulae (24) to (25):
Ar 2 is an aryl or heteroaryl group having 5 to 16 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 ;
t is 1;
R, R 2 are, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(R 1 ) 2 , N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CR 1 ═CR 1 Ar 1 , CN, NO 2 , Si(R 1 ) 3 , B(OAr 1 ) 2 , B(OR 1 ) 2 , OSO 2 R 1 , OH, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups is optionally replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , Ge(R 1 ) 2 , Sn(R 1 ) 2 , C═O, C═S, C═Se, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , O, S or CONR 1 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO 2 , or a mono- or polycyclic aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more non-aromatic radicals R, or a combination of these systems; two or more adjacent substituents R here may also be linked to one another and form a mono- or polycyclic aliphatic ring system, with the proviso that both R 2 in a benz[a]anthracene are either equal to H or not equal to H;
Ar 1 is on each occurrence, identically or differently, a mono-or poly-cyclic aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R; two radicals Ar 1 which are bonded to the same nitrogen or phosphorus atom may also be linked to one another here by a single bond or by a bridge selected from the group consisting of B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C═O, C═NR 1 , C═C(R 1 ) 2 , O, S, S═O, SO 2 , N(R 1 ), P(R 1 ) and P(═O)R 1 ;
R 1 is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by F; two or more adjacent substituents R 1 here may also form a mono-or polycyclic aliphatic or aromatic ring system with one another.
2. The compound according to claim 1 , wherein
Ar 2 is phenyl, 1-naphthyl, 2-naphthyl, 9-anthryl, chrysenyl, 1-pyrenyl, 2-pyrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 9-phenanthrenyl, 2-benz-imidazole, 2-fluorenyl, 2-spirobifluorenyl, fluoranthenyl, 2-benz[a]anthracenyl, 3-benz[a]anthracenyl, 4-benz[a]anthracenyl, 5-benz[a]anthracenyl or 6-benz[a]anthracenyl, each of which is optionally substituted by one or more radicals R 1 .
3. A process for the preparation of the compound according to claim 1 , which comprises coupling a benz[a]anthracene which is substituted in position 8 or 11 by a reactive leaving group to a functionalised aromatic compound or to a mono- or disubstituted amine.
4. An oligomer, polymer or dendrimer comprising one or more compounds according to claim 1 , where one or more radicals R or R 2 or X represent bonds from the compound according to claim 1 to the polymer, oligomer or dendrimer.
5. An electronic device comprising at least one compound according to claim 1 .
6. The electronic device as claimed in claim 5 , wherein the device is selected from organic electroluminescent devices (OLEDs), 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) or organic photoreceptors.
7. The electronic device as claimed in claim 5 , wherein the device is an organic electroluminescent device wherein the compound of the formula (9) or (10) is employed as matrix material for fluorescent dopants, where the fluorescent dopants are selected from the class of monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styryl ethers, and arylamines, containing condensed aromatic groups, and condensed aromatic hydrocarbons, or wherein the compound of the formula (9) or (10) is employed as emitting material, as hole-transport material, as hole-injection material or as electron-transport material.
8. A solution or formulation comprising at least one compound according to claim 1 and at least one solvent.
9. The electronic device as claimed in claim 7 , wherein the compound of the formula (9) or (10) is employed as matrix material in an emitting layer comprising exactly one matrix material and one or more dopants.
10. The electronic device as claimed in claim 7 , wherein the compound of the formula (9) or (10) is employed as electron-transport material.