Materials for organic electroluminescent devices
The invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices.
1. An organic electroluminescent device comprising at least one compound of formula (1) used as matrix material for a fluorescent or phosphorescent compound in an emitting layer and/or in an electron blocker layer
where the symbols and indices used are as follows:
Ar 1 are the same or different at each instance and are an aromatic or heteroaromatic ring system which has 6 to 60 aromatic ring atoms and may in each case also be substituted by one or more R 2 radicals, where, in the case that q>0, at least the two Ar 1 may be joined and/or Ar 1 may be joined to Ar 2 via at least one bridge K;
K is the same or different at each instance and is a single bond or a bivalent bridge selected from N(R 2 ), B(R 2 ), O, C═O, C(R 2 ) 2 , Si(R 2 ) 2 , and S;
Ar 2 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals;
X is the same or different at each instance and is N or CR 1 ;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, CHO, C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, P(═O)(R 2 ), SO, SO 2 , O, S or CONR 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or a combination of these systems; at the same time, two or more adjacent R 1 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 6 to 60 aromatic ring atoms and may in each case also be substituted by one or more R 2 radicals;
R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, CHO, C(═O)R 3 , P(═O) (R 3 ) 2 , S(═O) R 3 , S(═O) 2 R 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 3 radicals, where one or more nonadjacent CH 2 groups may be replaced by C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, P(═O)(R 3 ), SO, SO 2 , O, S or CONR 3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals, or a combination of these systems; at the same time, two or more adjacent R 2 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
R 3 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R 4 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O) 2 Ar, CR 4 ═CR 4 Ar, CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , C═O, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 4 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or a combination of these systems; at the same time, two or more adjacent R 3 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
R 4 is the same or different at each instance and is H, D, F or an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aryl or heteroaryl group which has 5 to 40 ring atoms and may be substituted by one or more R 5 radicals, or a combination of these groups;
R 5 is the same or different at each instance and is H, D, F or an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms;
q is 0, 1 or 2;
where
Ar 2 in the case of a heteroaromatic ring system may be joined to the phenanthridine base skeleton via a C—C bond; and,
R 1 in the case of a heteroaromatic ring system may be joined to the phenanthridine base skeleton via a C—C bond.
2. The device according to claim 1 , wherein the compound is of formula (2)
where the symbols and indices have the definitions given in claim 1 .
3. The device according to claim 2 , wherein the compound isone of the formulae (3) to (8):
where the symbols and indices have the definitions given in claim 2 and, in addition, the two Ar 1 are not joined to one another and Ar 1 is not joined to Ar 2 by further K groups and, in the formulae (4), (5), (6), (7) and (8), q>0.
4. A mixture comprising at least one compound of formula (1)
where the symbols and indices used are as follows:
Ar 1 are the same or different at each instance and are an aromatic or heteroaromatic ring system which has 6 to 60 aromatic ring atoms and may in each case also be substituted by one or more R 2 radicals, where, in the case that q>0, at least the two Ar 1 may be joined and/or Ar 1 may be joined to Ar 2 via at least one bridge K;
K is the same or different at each instance and is a single bond or a bivalent bridge selected from N(R 2 ), B(R 2 ), O, C═O, C(R 2 ) 2 , Si(R 2 ) 2 , and S;
Ar 2 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals;
X is the same or different at each instance and is N or CR 1 ;
R 1 is the same or different at each instance and is H, D, F, Cl, Br, I, CHO, C(═O)Ar, P(═O)(Ar) 2 , S(═O)Ar, S(═O) 2 Ar, CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 2 radicals, where one or more nonadjacent CH 2 groups may be replaced by C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, P(═O)(R 2 ), SO, SO 2 , O, S or CONR 2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 2 radicals, or a combination of these systems; at the same time, two or more adjacent R 1 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 6 to 60 aromatic ring atoms and may in each case also be substituted by one or more R 2 radicals;
R 2 is the same or different at each instance and is H, D, F, Cl, Br, I, CHO, C(═O)R 3 , P(═O) (R 3 ) 2 , S(═O) R 3 , S(═O) 2 R 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 3 radicals, where one or more nonadjacent CH 2 groups may be replaced by C≡C, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, P(═O)(R 3 ), SO, SO 2 , O, S or CONR 3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 3 radicals, or a combination of these systems; at the same time, two or more adjacent R 2 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
R 3 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R 4 ) 2 , C(═O)Ar, P(═O)Ar 2 , S(═O)Ar, S(═O) 2 Ar, CR 4 ═CR 4 Ar, CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R 4 radicals, where one or more nonadjacent CH 2 groups may be replaced by R 4 C═CR 4 , C≡C, Si(R 4 ) 2 , C═O, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S or CONR 4 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R 4 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R 4 radicals, or a combination of these systems; at the same time, two or more adjacent R 3 substituents may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
R 4 is the same or different at each instance and is H, D, F or an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms or an aryl or heteroaryl group which has 5 to 40 ring atoms and may be substituted by one or more R 5 radicals, or a combination of these groups;
R 5 is the same or different at each instance and is H, D, F or an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms;
q is 0, 1 or 2;
where
Ar 2 in the case of a heteroaromatic ring system may be joined to the phenanthridine base skeleton via a C—C bond; and,
R 1 in the case of a heteroaromatic ring system may be joined to the phenanthridine base skeleton via a C—C bond and at least one fluorescent or phosphorescent dopant.
5. The mixture according to claim 4 , wherein the compound is of formula (2)
where the symbols and indices have the definitions given in claim 4 .
6. The mixture according to claim 4 , wherein the compound is one of the formulae (3) to (8):
where the symbols and indices have the definitions given in claim 4 and, in addition, the two Ar 1 are not joined to one another and Ar 1 is not joined to Ar e by further K groups and, in the formulae (4), (5), (6), (7) and (8), q>0.