Materials for organic electroluminescent devices
The invention relates to compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.
1. A compound of formula (1)
where the symbols and indices used are as follows:
A is O or S;
X two adjacent X are a group of the formula (2)
where ^ indicates the corresponding adjacent X groups in formula (1), and the two remaining X groups are CR;
Z is CR; or two adjacent Z are a group of the formula (2a) and the two other Z are CR,
formula (2a)
where ^ indicates the corresponding adjacent Z groups in formula (2); W here is O, S, NR or CR 2 ;
Ar is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R radicals;
R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO 2 , N(Ar 1 ) 2 , N(R 1 ) 2 , P(Ar 1 ) 2 , B(Ar 1 ) 2 , Si(Ar 1 ) 3 , Si(R 1 ) 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R 1 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═S, C═NR 1 , SO 2 , NR 1 , O, S or CONR 1 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, it is optionally possible for two adjacent R substituents to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R 1 radicals;
Ar 1 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R 1 radicals; at the same time, two Ar 1 radicals bonded to the same nitrogen, phosphorus, boron or silicon atom may also be bridged to one another by a single bond or a bridge selected from N(R 1 ), C(R 1 ) 2 , O and S;
R 1 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, CN or an alkyl group having 1 to 10 carbon atoms; at the same time, two or more adjacent R 1 substituents together may form a mono- or polycyclic, aliphatic ring system;
p is the same or different at each instance and is 0, 1, 2, 3 or 4.
2. The compound as claimed in claim 1 , where in the compound is selected from the compounds of the formulae (3) to (8)
where the symbols and indices used have the definitions given in claim 1 .
3. The compound as claimed in claim 1 , wherein p is the same or different at each instance and is 0 or 1.
4. The compound as claimed in claim 1 , wherein the compound is selected from the compounds of the formulae (3a) to (8a)
where the symbols used have the definitions given in claim 1 .
5. The compound as claimed in claim 1 , wherein the compound is selected from the compounds of the formulae (3b) to (8b)
where the symbols used have the definitions given in claim 1 .
6. The compound as claimed in claim 1 , wherein A is oxygen.
7. The compound as claimed in claim 1 , wherein the compound is selected from the compounds of the formulae (3d) to (8d)
where the symbols used have the definitions given in claim 1 .
8. The compound as claimed in claim 1 , wherein Ar is selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, inclolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, phenanthrene, triphenylene and combinations of two or three of these groups, where these groups may each be substituted by one or more R radicals.
9. The compound as claimed in claim 1 , wherein R is the same or different at each instance and is selected from the group consisting of H, D, F, CN, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)(Ar 1 ) 2 , a straight-chain alkyl or alkoxy group having 1 to 10 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, each of which may be substituted by one or more R 1 radicals, where one or more nonadjacent CH 2 groups may be replaced by O and where one or more hydrogen atoms may be replaced by D or F, or an aromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals.
10. A process for preparing the compound as claimed in claim 1 , comprising the reaction steps of:
a) synthesizing the base skeleton which does not yet contain an Ar group; and
b) converting the base skeleton from a) in a C—N coupling or in a nucleophilic aromatic substitution reaction for introduction of the Ar group.
11. A formulation comprising at least one compound as claimed in claim 1 and at least one solvent.
12. An electronic device comprising the formulation as claimed in claim 11 .
13. An electronic device comprising at least one compound as claimed in claim 1 .
14. An organic electroluminescent device which comprises the compound as claimed in claim 1 is used in an emitting layer as matrix material for phosphorescent emitters or in an electron transport layer or in a hole transport layer or in an exciton blocker layer or in a hole blocker layer.