Benzanthracene derivatives for organic electroluminescent devices

1. An uncharged compound of the formula (1)

wherein the group Ar or Y is bonded via one of positions 2, 3, 4, 5 or 6 of the benz[a]anthracene and correspondingly no radical R is bonded at this position and where the following applies to the symbols and indices:

Ar is on each occurrence, identically or differently, a divalent aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R;

Y is a selected from the formula (25)-(31)

wherein

R is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(Ar 1 ) 2 , N(R 1 ) 2 , C(═O)Ar 1 , P(Ar 1 ) 2 , 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 or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkoxy group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 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 F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R, or a combination of these systems; two or more adjacent substituents R here optionally form a mono- or polycyclic aliphatic ring system with one another;

wherein R in positions 7 and 12 of the benzanthracene is hydrogen;

Ar 1 is on each occurrence, identically or differently, an 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 is optionally linked to one another here by a single bond or by a bridge selected from 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 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 optionally form a mono- or polycyclic aliphatic or aromatic ring system with one another;

Ar 2 is an aryl or heteroaryl group having 5 to 16 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 1 , or in formula (25) a group of the formula (32) or (33)

Ar 3 is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 20 aromatic ring atoms or a triarylamine group having 15 to 30 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 1 ;

E stands for a single bond, O, S, N(R 1 ) or C(R 1 ) 2 , where the two radicals R 1 optionally forms a Spiro system through ring formation;

q is 1, 2 or 3;

s is on each occurrence, identically or differently, 0 or 1;

m is on each occurrence, identically or differently 0 or 1; and

n is 0;

p is 0.

2. The compound according to claim 1 , wherein the compound of formula (1) is of the formula (2)

where

R is hydrogen,

the group Ar or Y is bonded via one of positions 2, 3, 4, 5 or 6 of the benz[a]anthracene and where the symbols and indices have the same meaning as described in claim 1 .

3. 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-benzimidazole, 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 , or in formula (25) a group of the formula (32) or (33); and

Ar 3 is, identically or differently on each occurrence, an aryl or heteroaryl group having 6 to 14 aromatic ring atoms or a triarylamine group having 15 to 22 aromatic ring atoms, each of which may be substituted by one or more radicals R 1 .

4. The compound according to claim 1 , wherein the symbol Ar stands, identically or differently on each occurrence, for an arylene or heteroarylene group selected from 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,4-naphthylene, 9,10-anthrylene, 2,7-phenanthrenylene, 3,6-phenanthrenylene, 1,6-pyrenylene, 2,7-pyrenylene, 2,6-pyridinylene, 2,5-pyridinylene, 2,2′-biphenyl, 3,3′-biphenyl, 4,4′-biphenyl, 2,7-fluorenyl and 2,7-spirobifluorenyl.

5. The compound according to claim 1 , wherein the compound is selected from formulae (3)-(7)

wherein the symbols and indices have the same meaning as described in claim 2 , and R is H,

wherein the benz[a]anthracene skeleton optionally carries deuterium instead of hydrogen.

6. The compound according to claim 1 , wherein

Ar 2 is an aryl or heteroaryl group having 5 to 16 aromatic ring atoms, each of which is optionally substituted by one or more radicals R 1 .

7. An organic electronic device which comprises the compound as claimed in claim 1 .

8. The organic electronic device as claimed in claim 7 , wherein the device is an organic electroluminescent device, an organic field-effect transistor (O-FET), an organic thin-film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic integrated circuit (O-IC), an organic solar cell (O-SC), an organic field-quench device (O-FQD), a light-emitting electrochemical cell (LEC), an organic laser diode (O-laser) or an organic photo receptor.

9. The organic electronic device as claimed in claim 8 , wherein the device is an electroluminescent device and the compound is employed as host material for a fluorescent dopant, wherein the fluorescent dopant is a monostyrylamine, a distyrylamine, a tristyrylamine, a tetrastyrylamine, a styrylphosphine, a styryl ether or an arylamine.

10. The organic electroluminescent device according to claim 8 , wherein the compound is employed as emitting material (dopant), as hole-transport material, as hole-injection material or as electron-transport material.

11. A process for the preparation of the compound according to claim 1 , which comprises bonding the group Ar or Y in the 6-position of the benz[a]anthracene, by reacting an optionally substituted 2-(2′-arylacetylene)phenylnaphthalene with an electrophile.

12. A process for the preparation of the compound according to claim 1 , which comprises substituting a benz[a]anthracene by a reactive leaving group and coupling to a functionalised aromatic compound or to a mono- or disubstituted amine.

13. The process according to claim 12 , wherein the reactive leaving group is chlorine, bromine, iodine, triflate, tosylate, boronic acid or boronic acid ester and the coupling is by a Suzuki coupling with palladium catalysis or by a palladium-catalysed coupling by the Hartwig-Buchwald method.

14. A compound of the formula (34)

wherein

R is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(Ar 1 ) 2 , N(R 1 ) 2 , C(═O)Ar 1 , P(Ar 1 ) 2 , 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 or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkoxy group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 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 F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more non-aromatic radicals R, or a combination of these systems; two or more adjacent substituents R here optionally form a mono- or polycyclic aliphatic ring system with one another;

Ar 1 is on each occurrence, identically or differently, an 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 is optionally linked to one another here by a single bond or by a bridge selected from B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , CO═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 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 optionally form a mono- or polycyclic aliphatic or aromatic ring system with one another;

and R 2 is bonded in position 2, 3, 4, 5 or 6 of the benz[a]anthracene and correspondingly no group R is bonded at this position, and furthermore:

R 2 stands for B(OR 1 ) 2 or B(OAr 1 ) 2 .

15. An oligomer, polymer or dendrimer which comprises one or more compounds according to claim 1 , where one or more radicals R or Ar or Y represent bonds from the compound according to claim 1 to the polymer, oligomer or dendrimer.

16. An electronic device which comprises the oligomer, dendrimer or polymer according to claim 15 .

17. The electronic device according to claim 16 wherein the electronic device is an organic electroluminescent device.