Composition for organic electronic devices

A composition comprising at least one compound of the formula (1) and at least one compound of the formula (2) or of the formula (3):

• wherein
• R* is a group of the following formula (1a):
• where the dashed bond represents the bond to the nitrogen atom in formula (1);
• X is the same or different at each instance and is N or CR, with the proviso that at least one X group is N and, if X is CRc, this does not form a ring with Ara or Ab;
• L is the same or different at each instance and is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals, where L, together with an R radical or Ra radical may also form an aliphatic, heteroaliphatic or heteroaromatic ring system, or L is a group of the formula -L1-Q-L2- where L2 binds to the heteroaryl group of the formula (1a), and L1 to the nitrogen atom of the main structure of the formula (1);
• Q is a group of the formula (4):
• where the dashed bonds represent the linkage to L1 or L2, and L1 and L2 at each instance may be bonded either to the same or to different phenyl rings of the group of the formula (4), with the proviso that the sum total of aromatic ring atoms including all heteroatoms in the L1, L2 and Q groups is 13 to 40;
• G is the same or different at each instance and is O or S;
• L1, L2 are the same or different at each instance and are each independently a single bond or an aryl group having 6 to 24 aromatic ring atoms or a heteroaryl group having 5 to 24 aromatic ring atoms, each of which may be substituted by one or more R1 radicals;
• Ara, Arb are the same or different at each instance and are each independently an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals;
• Arc, Ard are the same or different at each instance and are each independently an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more Rd radicals;
• Y is the same or different at each instance and is selected from O, S and C(Rg)2;
• Ar′, Ar2 are the same or different at each instance and are each independently an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals;
• R, Ra, Rb are the same or different at each instance and are each independently H, D, F, Cl, Br, I, N(Ar′)2, N(R′)2, OAr′, SAr′, B(OR1)2, CHO, C(═O)R1, CR1═C(R1)2, CN, C(═O)OR1, C(═O)NR1, Si(R1)3, NO2, P(═O)(R1)2, OSO2R1, OR1, S(═O)R1, S(═O)2R1, SR1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by —R1C═CR1—, —C≡C—, Si(R1)2, CONR1, C═O, C═S, —C(═O)O—, P(═O)(R1), O, S, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals, where two or more R and/or Ra and/or Rb radicals bonded to the same cycle may together form an aliphatic or heteroaliphatic ring system that may be substituted by one or more R1 radicals, and where two R and/or Ra and/or Rb radicals bonded to the same carbon, silicon, germanium or tin atom may together form a monocyclic or polycyclic, aliphatic or aromatic ring system that may be substituted by one or more R1 radicals;
• Rc, Re, Rf, Rg, Rh, Ri are the same or different at each instance and are each independently H, D, F, Cl, Br, I, N(Ar′)2, N(R1)2, OAr′, SAr′, B(OR1)2, CHO, C(═O)R1, CR1═C(R1)2, CN, C(═O)OR1, C(═O)NR1, Si(R1)3, NO2, P(═O)(R1)2, OSO2R1, OR1, S(═O)R1, S(═O)2R1, SR1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by —R1C═CR1—, —C≡C—, Si(R1)2, NR1, CONR1, C═O, C═S, —C(═O)O—, P(═O)(R1), O, S, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals, where two or more Rc, Re, Rf, Rg, Rh or Ri radicals bonded to the same cycle may together form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more Rr radicals, and where two Rc, Re, Rf, Rg, Rh or Ri radicals bonded to the same carbon, silicon, germanium or tin atom may together form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system that may be substituted by one or more R1 radicals;
• Rd is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar′)2, N(R1)2, OAr′, SAr′, B(OR1)2, CHO, CO(═O)R1, CR1═C(R1)2, CN, C(═O)OR1, C(═O)NR1, Si(R1)3, NO2, P(═O)(R1)2, OSO2R1, S(═O)R1, S(═O)2R1, SR1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may be substituted in each case by one or more R1 radicals, where one or more nonadjacent CI groups may be replaced by —R1C═CR1—, —C≡C—, Si(R1)2, NR1, CONR1, C═O, C═S, —C(═O)O—, P(═O)(R1), O, S, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, where two or more Rd radicals bonded to the same cycle may together form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R1 radicals, and where two R radicals bonded to the same carbon, silicon, germanium or tin atom may together form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R1 radicals;
• Rx is H, D or (Lx)y-Arx;
• Lx is the same or different at each instance and is a single bond, or an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals;
• Arx is the same or different at each instance and is an unsubstituted or substituted 9-Ard-carbazolyl or an unsubstituted or substituted carbazol-9-yl that may be substituted by one or more R1 radicals and where it may independently be the case at one or more instances that two R1 radicals or one R1 radical together with one Ard or Rf radical form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring, or, when y=0, two adjacent Rf and Arx may together form a ring of the formula (5), where the positions marked by * represent the bonds to the phenyl ring of the formula (2), and the other Rf are the same or different at each instance and are H or a substituent as defined above;
• Ar′ is the same or different at each instance and is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more R1 radicals;
• R1 is the same or different at each instance and is D, F, I, B(OR2)2, N(R2)2, CHO, C(═O)R2CR2═C(R2)2, CN, C(═O)OR2, Si(R2)3, NO2, P(═O)(R2)2, OSO2R2, SR2, OR2, S(═O)R2, S(═O)2R2, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R2 radicals and where one or more CH2 groups in the abovementioned groups may be replaced by —R2C═CR2—, —C≡C—, Si(R2)2, C═O, C═S, —C(═O)O—, NR2, CONR2, P(═O)(R2), O, S, SO or SO2, and where one or more hydrogen atoms in the abovementioned groups may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, where two or more R1 radicals together may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
• R2 is the same or different at each instance and is D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by D or F;
• at the same time, two or more R-substituents may be joined to one another and may form a ring;
• l, m, p, q are the same or different at each instance and are independently 0, 1, 2 or 3;
• n, o, r, z, s, t are the same or different at each instance and are independently 0, 1, 2, 3 or 4;
• and
• y at each instance is independently 0 or 1.

A compound of the formula (1):

• where:
• R* is a group of the following formula (1a):
• where the dashed bond represents the bond to the nitrogen atom in formula (1);
• X is the same or different at each instance and is N or CRc, with the proviso that at least one X group is N and, if X is CRc, this does not form a ring with Ara or Arb;
• L is the same or different at each instance and is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals, where L together with an R radical or Ra radical may also form an aliphatic, heteroaliphatic or heteroaromatic ring system, or L is a group of the formula -L1-Q-L2- where L binds to the heteroaryl group of the formula (1a), and L1 to the nitrogen atom of the main structure of the formula (1);
• Q is a group of the formula (4):
• where the dashed bonds represent the linkage to L1 or L2, and L1 and L2 at each instance may be bonded either to the same or to different phenyl rings of the group of the formula (4), with the proviso that the sum total of aromatic ring atoms including all heteroatoms in the L1, L2 and Q groups is 13 to 40;
• G is the same or different at each instance and is O or S;
• L1, L2 are the same or different at each instance and are each independently a single bond, an aryl group having 6 to 24 aromatic ring atoms or a heteroaryl group having 5 to 24 aromatic ring atoms, each of which may be substituted by one or more R1 radicals;
• Ara, Arb are the same or different at each instance and are each independently an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals;
• R, Ra, Rb are the same or different at each instance and are each independently H, D, F, Cl, Br, I, N(Ar′)2, N(R1)2, OAr′, SAr′, B(OR1)2, CHO), C(═O)R1, CR1═C(R1)2, CN, C(═O)OR1, C(═O)NR1, Si(R1)3, NO2, P(═O)(R1)2, OSO2R1, OR1, S(═O)R1, S(═O)2R1, SR1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by —R1C═CR1—, —C≡C—, Si(R1)2, CONR1, C═O, C═S, —C(═O)O—, P(═O)(R1), O, S, SO or SO2, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, each of which may be substituted by one or more R1 radicals, where two or more R and/or Ra and/or Rb radicals bonded to the same cycle may together form an aliphatic or heteroaliphatic ring system that may be substituted by one or more R1 radicals, and where two R and/or Ra and/or Rb radicals bonded to the same carbon, silicon, germanium or tin atom may together form a monocyclic or polycyclic, aliphatic or aromatic ring system that may be substituted by one or more R1 radicals;
• Rc is the same or different at each instance and is H, D, F, Cl, Br, I, N(Ar′)2, N(R1)2, OAr′, SAr′, B(OR1)2, CHO, C(═O)R1, CR1═C(R1)2, CN, C(═O)OR1, C(═O)NR1, Si(R1)3, NO2, P(═O)(R1)2, OSO2R1, OR1, S(═O)R1, S(═O)2R1, SR1, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may be substituted in each case by one or more R1 radicals, where one or more nonadjacent CH2 groups may be replaced by —R1C═CR1—, —C≡C—, Si(R1)2, NR1, CONR1, C═O, C═S, —C(═O)O—, P(═O)(R1), O, S, SO or SO2, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R1 radicals, where two or more Rc radicals bonded to the same cycle may together form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R1 radicals, and where two Rc radicals bonded to the same carbon, silicon, germanium or tin atom may together form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R1 radicals;
• R1 is the same or different at each instance and is D, F, I, B(OR2)2, N(R2)2, CHO, C(═O)R2, CR2═C(R2)2, CN, C(═O)OR2, Si(R2)3, NO2, P(═O)(R2)2, OSO2R2, SR2, OR2, S(═O)R2, S(═O)2R2, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R2 radicals and where one or more CH2 groups in the abovementioned groups may be replaced by —R2C═CR2—, —C≡C—, Si(R2)2, C═O, C═S, —C(═O)O—, NR2, CONR2, P(═O)(R2), O, S, SO or SO2, and where one or more hydrogen atoms in the abovementioned groups may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, where two or more R1 radicals together may form an aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
• R2 is the same or different at each instance and is D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by D or F;
• at the same time, two or more R2 substituents may be joined to one another and may form a ring;
• s, t are the same or different at each instance and are independently 0, 1, 2, 3 or 4;
• l, m are the same or different at each instance and are independently 0, 1, 2 or 3;
• n is the same or different at each instance and is independently 0, 1, 2, 3 or 4.