Materials for electronic devices
The present application concerns compounds for use in electronic devices, processes for preparing the compounds, and electronic devices comprising the compounds.
1. A compound of formula (I)
where:
FL is a group of formulae (FL-1)
where the dotted bond is the bond to the rest of formula (I);
Z is identically or differently at each occurrence, selected from CR 1 and N;
Y is C if a group —[Ar 2 ] n —N(Ar 3 )(Ar 4 ) or —[Ar 1 ] m -FL is bonded in this position; and Y is in all other cases selected, identically or differently at each occurrence, from CR 3 and N;
X is O or S;
Ar 1 is, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R 4 , and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R 4 ;
Ar 2 is, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R 5 , and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R 5 ;
A corresponds to the following formula
which is bonded via the dotted line;
Ar 3 and Ar 4 are, identically or differently at each occurrence, selected from aromatic ring systems having 6 to 40 aromatic ring atoms, which are substituted by radicals R 6 , and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, which are substituted by radicals R 6 ;
k is 0 which means that T does not occur and the groups Ar 3 and Ar 4 are not connected;
R 1 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 7 , CN, Si(R 7 ) 3 , N(R 7 ) 2 , P(═O)(R 7 ) 2 , OR 7 , S(═O) R 7 , S(═O) 2 R 7 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 1 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 7 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 7 C═CR 7 —, —C≡C—, Si(R 7 ) 2 , C═O, C═NR 7 , —C(═O)O—, —C(═O)NR 7 —, NR 7 , P(═O)(R 7 ), —O—, —S—, SO or SO 2 ;
R 2 is selected, identically or differently at each occurrence, from straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl, groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 7 ;
R 3 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 7 , CN, Si(R 7 ) 3 , N(R 7 ) 2 , P(═O)(R 7 ) 2 , OR 7 , S(═O)R 7 , S(═O) 2 R 7 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 3 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 7 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 7 C═CR 7 —, —C≡C—, Si(R 7 ) 2 , C═O, C═NR 7 , —C(═O)O—, —C(═O)NR 7 —, NR 7 , P(═O)(R 7 ), —O—, —S—, SO or SO 2 ;
R 4 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 7 , CN, Si(R 7 ) 3 , N(R 7 ) 2 , P(═O)(R 7 ) 2 , OR 7 , S(═O)R 7 , S(═O) 2 R 7 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 4 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 7 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 7 C═CR 7 —, —C≡C—, Si(R 7 ) 2 , C═O, C═NR 7 , —C(═O)O—, —C(═O)NR 7 —, NR 7 , P(═O)(R 7 ), —O—, —S—, SO or SO 2 ;
R 5 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 7 , CN, Si(R 7 ) 3 , N(R 7 ) 2 , P(═O)(R 7 ) 2 , OR 7 , S(═O)R 7 , S(═O) 2 R 7 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case substituted by radicals R 7 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 7 C═CR 7 —, —C≡C—, Si(R 7 ) 2 , C═O, C═NR 7 , —C(═O)O—, —C(═O)NR 7 —, NR 7 , P(═O)(R 7 ), —O—, —S—, SO or SO 2 ;
R 6 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 7 , CN, Si(R 7 ) 3 , N(R 7 ) 2 , P(═O)(R 7 ) 2 , OR 7 , S(═O)R 7 , S(═O) 2 R 7 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R 6 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case be substituted by radicals R 7 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 7 C═CR 7 —, —C≡C—, Si(R 7 ) 2 , C═O, C═NR 7 , —C(═O)O—, —C(═O)NR 7 —, NR 7 , P(═O)(R 7 ), —O—, —S—, SO or SO 2 ;
R 7 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, C(═O)R 8 , CN, Si(R 8 ) 3 , N(R 8 ) 2 , P(═O)(R 8 ) 2 , OR 8 , S(═O)R 8 , S(═O) 2 R 8 , straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems are in each case be substituted by radicals R 8 , and where one or more CH 2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R 8 C═CR 8 —, —C≡C—, Si(R 8 ) 2 , C═O, C═NR 8 , —C(═O)O—, —C(═O)NR 8 —, NR 8 , P(═O)(R 8 ), —O—, —S—, SO or SO 2 ;
R 8 is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, alkyl groups having 1 to 20 C atoms, aromatic ring systems having 6 to 40 C atoms, or heteroaromatic ring systems having 5 to 40 aromatic ring atoms; and where the said alkyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by one or more radicals selected from F and CN;
m is 1, 2, 3, or 4;
n is 0, 1, 2, 3, or 4.
2. The compound according to claim 1 , wherein it is a monoamine.
3. The compound according to claim 1 , wherein X is O.
4. The compound according to claim 1 , wherein m is 1.
5. The compound according to claim 1 , wherein —[Ar 1 ] m — for the case of m=1 is 1,4-phenylene, which is substituted with radicals R 4 .
6. The compound according to claim 1 , wherein groups —[Ar 2 ] n — for the case of n=1 are selected from divalent groups derived from phenyl, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzothiophene, and carbazole, which are substituted with radicals R 5 .
7. The compound according to claim 1 , wherein Ar 3 and Ar 4 are selected, identically or differently, from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, particularly 9,9′-dimethylfluorenyl and 9,9′-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-condensed dibenzofuranyl, benzo-condensed dibenzothiophenyl, phenyl substituted with naphthyl, phenyl substituted with fluorenyl, phenyl substituted with spirobifluorenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothiophene, phenyl substituted with carbazolyl, phenyl substituted with pyridyl, phenyl substituted with pyrimidyl, and phenyl substituted with triazinyl, where the groups are each substituted with radicals R 6 .
8. The compound according to claim 1 , wherein
R 1 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 2 is selected, identically or differently, from a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, and an aromatic ring system having 6 to 40 aromatic ring atoms; where the said alkyl group and the said aromatic ring system are substituted by radicals R 7 ; and
R 3 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 4 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 5 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 6 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl alkoxy groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 7 is selected, identically or differently, from H, D, F, CN, Si(R 8 ) 3 , N(R 8 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 8 ;
n=1;
—Ar 2 — is selected from divalent groups derived from phenyl, biphenyl, naphthyl and fluorene, which are substituted with radicals R 5 ;
Ar 3 and Ar 4 are selected, identically or differently, from phenyl, biphenyl, terphenyl quaterphenyl, naphthyl, fluorenyl, particularly 9,9′-dimethylfluorenyl and 9,9′-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-condensed dibenzofuranyl, benzo-condensed dibenzothiophenyl, phenyl substituted with naphthyl, phenyl substituted with fluorenyl, phenyl substituted with spirobifluorenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothiophene, phenyl substituted with carbazolyl, phenyl substituted with pyridyl, phenyl substituted with pyrimidyl, and phenyl substituted with triazinyl, where the groups are each substituted with radicals R 6 .
9. The compound according to claim 1 , wherein R 2 is selected, identically or differently on each occurrence, from the following groups
where the dotted bond represents the bond to the rest of the formula.
10. The compound according to claim 1 , wherein it conforms to the following formulae
where the variables occurring are defined as in claim 1 .
11. The compound according to claim 10 , wherein the compound conforms to formula (I-A-1-4) or (I-A-1-9).
12. An oligomer, polymer or dendrimer, comprising one or more compounds of formula (I) according to claim 1 , where the bond(s) to the polymer, oligomer or dendrimer may be localised at any desired positions in formula (I) substituted by R 1 , R 2 , R 3 , R 4 , R 5 or R 6 .
13. A formulation, comprising at least one compound of formula (I) according to claim 1 , and at least one solvent.
14. An electronic device, comprising at least one compound according to claim 1 .
15. The electronic device according to claim 14 , wherein the device is an organic electroluminescent device, comprising anode, cathode and at least one emitting layer, where at least one organic layer of the device, which is a hole transport layer, an electron blocking layer or a hole injection layer, comprises the at least one compound.
16. A method comprising incorporating the compound according to claim 1 in an electronic device.
17. The compound according to claim 10 , wherein
R 1 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 2 is selected, identically or differently, from a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, and an aromatic ring system having 6 to 40 aromatic ring atoms; where the said alkyl group and the said aromatic ring system are substituted by radicals R 7 ; and
R 3 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 4 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 5 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 6 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ;
R 7 is selected, identically or differently, from H, D, F, CN, Si(R 8 ) 3 , N(R 8 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 8 ;
n=1;
—Ar 2 — is selected from divalent groups derived from phenyl, biphenyl, naphthyl and fluorene, which are substituted with radicals R 5 ; and
Ar 3 and Ar 4 are selected, identically or differently, from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, particularly 9,9′-dimethylfluorenyl and 9,9′-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-condensed dibenzofuranyl, benzo-condensed dibenzothiophenyl, phenyl substituted with naphthyl, phenyl substituted with fluorenyl, phenyl substituted with spirobifluorenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothiophene, phenyl substituted with carbazolyl, phenyl substituted with pyridyl, phenyl substituted with pyrimidyl, and phenyl substituted with triazinyl, where the groups are each substituted with radicals R 6 .
18. The compound according to claim 11 , wherein
R 1 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 2 is selected, identically or differently, from a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, and an aromatic ring system having 6 to 40 aromatic ring atoms; where the said alkyl group and the said aromatic ring system are substituted by radicals R 7 ; and
R 3 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 4 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 5 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 6 is selected, identically or differently, from H, D, F, CN, Si(R 7 ) 3 , N(R 7 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 7 ; and
R 7 is selected, identically or differently, from H, D, F, CN, Si(R 8 ) 3 , N(R 8 ) 2 , straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the said alkyl groups and the said aromatic and heteroaromatic ring systems are substituted by radicals R 8
n=1;
—Ar 2 — is selected from divalent groups derived from phenyl, biphenyl, naphthyl and fluorene, which are substituted with radicals R 5 ;
Ar 3 and Ar 4 are selected, identically or differently, from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, particularly 9,9′-dimethylfluorenyl and 9,9′-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-condensed dibenzofuranyl, benzo-condensed dibenzothiophenyl, phenyl substituted with naphthyl, phenyl substituted with fluorenyl, phenyl substituted with spirobifluorenyl, phenyl substituted with dibenzofuranyl, phenyl substituted with dibenzothiophene, phenyl substituted with carbazolyl, phenyl substituted with pyridyl, phenyl substituted with pyrimidyl, and phenyl substituted with triazinyl, where the groups are each substituted with radicals R 6 .