HETEROCYCLIC COMPOUNDS FOR ORGANIC ELECTROLUMINESCENT DEVICES
The invention relates to heterocyclic compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.
1 .- 19 . (canceled)
20 . A compound including at least one structure of formula (I)
where the rings Ar a and Ar b are the same or different at each instance and are an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or R radicals, where the rings Ar a and Ar b together may form a ring system; and where the further symbols and indices used are as follows:
Z 1 , Z 2 , Z 3 is the same or different at each instance and is N or B;
W 1 , W 2 is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) groups or the carbon atom and the nitrogen atom of the C═N group are each parts of the ring Ar a or Ar b , where the carbon atom of the C═N group binds to the V 1 or V 4 group;
V 1 , V 2 is the same or different at each instance and is —N═, —B═, ═C(Ar)— or ═C(R)—, or the V 1 , V 2 groups form a ring of the formula
where the ring Ar c is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or R radicals, where the ring Ar c may form a ring system together with an X 1 group or the rings Ar a and Ar c together may form a ring system, where W 3 binds to the W 1 group and is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) group or the carbon atom and the nitrogen atom of the C═N group are each parts of the Ar c ring, where the carbon atom of the C═N group binds to the W 1 group and the dotted lines represent the bonds to the W 1 or Z 2 group;
V 3 , V 4 is the same or different at each instance and is —N═, —B═, (Ar)C═C(Ar) or (R)C═C(R), or the V 3 , V 4 groups form a ring of the formula
where the ring Ar d is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more Ar or R radicals, where the ring Ar d may form a ring system together with an X 1 group or the rings Ar b and Ar d together may form a ring system, where W 4 binds to the W 2 group and is the same or different at each instance and is N, B, C═C(Ar), C═C(R) or C═N, where both carbon atoms of the C═C(Ar) or C═C(R) group or the carbon atom and the nitrogen atom of the C═N group are each parts of the Ar a or Ar b ring, where the carbon atom of the C═N group binds to the W 2 group and the dotted lines represent the bonds to the W 2 or Z 3 group;
Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R radicals; the Ar group here may form a ring system with at least one Ar, X 1 , R group or a further group;
X 1 is the same or different at each instance and is N, CR 1 or C if a ring system is formed by a bond to one of the rings Ar c , Ar d or a further group, with the proviso that not more than two of the X 1 , X 2 groups in one cycle are N;
X 2 is the same or different at each instance and is N or CR b , with the proviso that not more than two of the X 1 , X 2 groups in one cycle are N;
R, R a , R b is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(═O)OAr′, C(═O)OR 1 , C(═O)N(Ar′) 2 , C(═O)N(R 1 ) 2 , C(Ar′) 3 , C(R 1 ) 3 , Si(Ar′) 3 , Si(R 1 ) 3 , B(Ar′) 2 , B(R 1 ) 2 , C(═O)Ar′, C(═O)R 1 , P(═O)(Ar′) 2 , P(═O)(R 1 ) 2 , P(Ar′) 2 , P(R 1 ) 2 , S(═O)Ar′, S(═O)R 1 , S(═O) 2 Ar′, S(═O) 2 R 1 , OSO 2 Ar′, OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may in each case 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═O, C═S, C═Se, C═NR 1 , —C(═O)O—, —C(═O)NR 1 —, NR 1 , p(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, two R, R a , R b radicals may also form a ring system together or with a further group;
Ar′ is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, it is possible for two Ar′ radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or 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 the same or different at each instance and is H, D, F, Cl, Br, I, CN, NO 2 , N(Ar″) 2 , N(R 2 ) 2 , C(═O)OAr″, C(═O)OR 2 , C(═O)Ar″, C(═O)R 2 , P(═O)(Ar″) 2 , P(Ar″) 2 , B(Ar″) 2 , B(R 2 ) 2 , C(Ar″) 3 , C(R 2 ) 3 , Si(Ar″) 3 , Si(R 2 ) 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 or an alkenyl groups having 2 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 —R 2 C═CR 2 —, —C≡C, Si(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 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 60 aromatic ring atoms and may be substituted in each case by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 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 R 1 radicals together may form a ring system; at the same time, one or more R 1 radicals may form a ring system with a further part of the compound;
Ar″ 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 R 2 radicals; at the same time, it is possible for two Ar″ radicals bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom also to be joined together via a bridge by a single bond or a bridge selected from B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C═O, C═NR 2 , C═C(R 2 ) 2 , O, S, S═O, SO 2 , N(R 2 ), P(R 2 ) and P(═O)R 2 ;
R 2 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 which has 5 to 30 aromatic ring atoms and in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more substituents R 2 together may form a ring system;
where at least one V 1 , V 2 , W 1 , W 3 group represents N or B and at least one V 3 , V 4 , W 2 , W 4 group represents N or B.
21 . The compound as claimed in claim 20 , comprising at least one structure of the formula (IIa), (IIb), (IIc), (IId) and/or (IIe):
where Z 1 , Z 2 , Z 3 , X 1 and X 2 have the definitions given in claim 20 and the further symbols are as follows:
Z 4 , Z 5 is the same or different at each instance and is N or B;
W 5 , W 6 , W 7 , W 8 is the same or different at each instance and is C(Ar) or X 6 , where Ar has the definition given in claim 20 ;
X 3 is the same or different at each instance and is N or CR 1 , with the proviso that not more than two of the X 3 , X 5 groups in one cycle are N;
X 4 is the same or different at each instance and is N or CR d , with the proviso that not more than two of the X 4 , X 6 groups in one cycle are N;
X 5 is the same or different at each instance and is N, CR c or C if a ring system is formed by a bond to an Ar group or an X 5 group or an X 6 group, with the proviso that not more than two of the X 3 , X 5 groups in one cycle are N;
X 6 is the same or different at each instance and is N, CR f or C if a ring system is formed by a bond to an Ar group or an X 5 group or an X 6 group, with the proviso that not more than two of the X 4 , X 6 groups in one cycle are N;
R C , R d , R e , R f is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(═O)OAr′, C(═O)OR 1 , C(═O)N(Ar′) 2 , C(═O)N(R 1 ) 2 , C(Ar′) 3 , C(R 1 ) 3 , Si(Ar′) 3 , Si(R 1 ) 3 , B(Ar′) 2 , B(R 1 ) 2 , C(═O)Ar′, C(═O)R 1 , P(═O)(Ar′) 2 , P(═O)(R 1 ) 2 , P(Ar′) 2 , P(R 1 ) 2 , S(═O)Ar′, S(═O)R 1 , S(═O) 2 Ar′, S(═O) 2 R 1 , OSO 2 Ar′, OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case 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═O, C═S, C═Se, C═NR 1 , —C(═O)O—, —C(═O)NR 1 —, NR 1 , P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, two R c , R d , R e , R f radicals may also form a ring system together or with a further group, where the R 1 radical has the definition given in claim 20 .
22 . The compound according to claim 20 , including at least one structure of the formula (III-1) to (III-25):
where the symbols Z 1 , Z 2 , Z 3 , X 1 and X 2 have the definitions given in claim 20 ,
Z 4 , Z 5 is the same or different at each instance and is N or B;
X 3 is the same or different at each instance and is N or CR C , with the proviso that not more than two of the X 3 , X 5 groups in one cycle are N;
X 4 is the same or different at each instance and is N or CR d , with the proviso that not more than two of the X 4 , X 6 groups in one cycle are N;
X 5 is the same or different at each instance and is N, CR c or C if a ring system is formed by a bond to an Ar group or an X 5 group or an X 6 group, with the proviso that not more than two of the X 3 , X 5 groups in one cycle are N;
X 6 is the same or different at each instance and is N, CR f or C if a ring system is formed by a bond to an Ar group or an X 5 group or an X 6 group, with the proviso that not more than two of the X 4 , X 6 groups in one cycle are N;
and the further symbols are defined as follows:
p is 0 or 1,
Y 1 is the same or different at each instance and is a bond, N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R) 2 , Si(R) 2 , C═NR, C═NAr′, C═C(R) 2 , O, S, Se, S═O, or SO 2 , where the symbols R and Ar′ have the definition set out in claim 20 ;
Y 2 , Y 3 , Y 4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R) 2 , Si(R) 2 , C═NR, C═NAr′, C═C(R) 2 , O, S, Se, S═O, or SO 2 , where the symbols R and Ar′ have the definition set out in claim 20 .
23 . The compound as claimed in claim 20 , including at least one structure of the formula (IV-1) to (IV-38):
where the symbols Z 1 , Z 2 , Z 3 , R a and R b have the definitions given in claim 20 ,
Z 4 , Z 5 is the same or different at each instance and is N or B;
R c , R d , R e , R f is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(═O)OAr′, C(═O)OR 1 , C(═O)N(Ar′) 2 , C(═O)N(R 1 ) 2 , C(Ar′) 3 , C(R 1 ) 3 , Si(Ar′) 3 , Si(R 1 ) 3 , B(Ar′) 2 , B(R 1 ) 2 , C(═O)Ar′, C(═O)R 1 , P(═O)(Ar′) 2 , P(═O)(R 1 ) 2 , P(Ar′) 2 , P(R 1 ) 2 , S(═O)Ar′, S(═O)R 1 , S(═O) 2 Ar′, S(═O) 2 R 1 , OSO 2 Ar′, OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case 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═O, C═S, C═Se, C═NR 1 , —C(═O)O—,
—C(═O)NR 1 —, NR 1 , P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, two R c , R d , R e , R f radicals may also form a ring system together or with a further group, where the R 1 radical has the definition given in claim 20 ;
yl is the same or different at each instance and is a bond, N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R) 2 , Si(R) 2 , C═NR, C═NAr′, C═C(R) 2 , O, S, Se, S═O, or SO 2 , where the symbols R and Ar′ have the definition set out in claim 20 ;
Y 2 , Y 3 , Y 4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R) 2 , Si(R) 2 , C═NR, C═NAr′, C═C(R) 2 , O, S, Se, S═O, or SO 2 , where the symbols R and Ar′ have the definition set out in claim 20 ;
and the further symbols are defined as follows:
m is 0, 1, 2, 3 or 4;
n is 0, 1, 2 or 3;
j is 0, 1 or 2;
k is 0 or 1.
24 . The compound as claimed in claim 24 , wherein Z 1 is N and at least one of the Z 2 , Z 3 , Z 4 , Z 5 groups is B.
25 . The compound as claimed in claim 21 , wherein Z 1 is N and at least one of the Z 2 , Z 3 , Z 4 , Z 5 groups is N.
26 . The compound as claimed in claim 21 , wherein Z 1 is B and at least one of the Z 2 , Z 3 , Z 4 , Z 5 groups is N.
27 . The compound as claimed in claim 20 , wherein Z 1 is B and at least one of the Z 2 , Z 3 , Z 4 , Z 5 groups is B.
28 . The compound as claimed in claim 20 , wherein at least two R, R a , R b , R c , R d , R e , R f radicals together with the further groups to which the two R, R a , R b , R c , R d , R e , R f radicals bind form a fused ring, where the two R, R a , R b , R c , R d , R e , R f radicals form at least one structure of the formulae (RA-1) to (RA-12):
where R 1 has the definition set out above, the dotted bonds represent the sites of attachment to the atoms of the groups to which the two R, R a , R b , R c , R d , R e , R f radicals bind, and the further symbols have the following definition:
Y 5 is the same or different at each instance and is C(R 1 ) 2 , (R 1 ) 2 C—C(R 1 ) 2 , (R 1 )C═C(R 1 ), NR 1 , NAr′, O or S;
R g is the same or different at each instance and is F, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case by one or more R 2 radicals, where one or more adjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , p(═o)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 2 radicals; at the same time, it is also possible for two R g radicals together or one R g radical together with an R 1 radical or together with a further group to form a ring system;
S is 0, 1, 2, 3, 4, 5 or 6;
t is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.
29 . The compound as claimed in claim 20 , wherein at least two R, R a , R b , R c , R d , R e , R f radicals together with the further groups to which the two R, R a , R b , R c , R d , R e , R f radicals bind form a fused ring, where the two R, R a , R b , R c , R d , R e , R f radicals form the structures of the formula (RB):
where R 1 has the definition set out in claim 20 , the dotted bonds represent the sites of attachment to which the two R, R a , R b , R c , R d , R e , R f radicals bind, the index m is 0, 1, 2, 3 or 4 and Y 6 is C(R 1 ) 2 , NR 1 , NAr′, BR 1 , BAr′, O or S.
30 . The compound as claimed in claim 20 , comprising at least one structure of the formulae (V-1) to (V-10), where the compounds have at least one fused ring,
where the symbols Z 1 , Z 2 , Z 3 , R a and R b have the definitions given in claim 20 ,
Z 4 , Z 5 is the same or different at each instance and is N or B;
R c , R d , R e , R f is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(═O)OAr′, C(═O)OR 1 , C(═O)N(Ar′) 2 , C(═O)N(R 1 ) 2 , C(Ar′) 3 , C(R 1 ) 3 , Si(Ar′) 3 , Si(R 1 ) 3 , B(Ar′) 2 , B(R 1 ) 2 , C(═O)Ar′, C(═O)R 1 , P(═O)(Ar′) 2 , P(═O)(R 1 ) 2 , P(Ar′) 2 , P(R 1 ) 2 , S(═O)Ar′, S(═O)R 1 , S(═O) 2 Ar′, S(═O) 2 R 1 , OSO 2 Ar′, OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case 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═O, C═S, C═Se, C═NR 1 , —C(═O)O—,
—C(═O)NR 1 —, NR 1 , P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, two R c , R d , R e , R f radicals may also form a ring system together or with a further group, where the R 1 radical has the definition given in claim 20 ,
Y 3 , Y 4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R) 2 , Si(R) 2 , C═NR, C═NAr′, C═C(R) 2 , O, S, Se, S═O, or SO 2 , where the symbols R and Ar′ have the definition set out in claim 20 ,
the symbol o represents the sites of attachment, and the further symbols are defined as follows:
m is 0, 1, 2, 3 or 4;
n is 0, 1, 2 or 3;
j is 0, 1 or 2.
31 . The compound as claimed in claim 20 , comprising at least one structure of the formulae (VI-1) to (VI-9), where the compounds have at least one fused ring,
where the symbols Z 1 , Z 2 , Z 3 , R a and R b have the definitions given in claim 20 ,
Z 4 , Z 5 is the same or different at each instance and is N or B;
R c , R d , R e , R f is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(═O)OAr′, C(═O)OR 1 , C(═O)N(Ar′) 2 , C(═O)N(R 1 ) 2 , C(Ar′) 3 , C(R 1 ) 3 , Si(Ar′) 3 , Si(R 1 ) 3 , B(Ar′) 2 , B(R 1 ) 2 , C(═O)Ar′, C(═O)R 1 , P(═O)(Ar′) 2 , P(═O)(R 1 ) 2 , P(Ar′) 2 , P(R 1 ) 2 , S(═O)Ar′, S(═O)R 1 , S(═O) 2 Ar′, S(═O) 2 R 1 , OSO 2 Ar′, OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case 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═O, C═S, C═Se, C═NR 1 , —C(═O)O—,
—C(═O)NR 1 —, NR 1 , P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, two R c , R d , R e , R f radicals may also form a ring system together or with a further group, where the R 1 radical has the definition given in claim 20 ,
Y 3 , Y 4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R) 2 , Si(R) 2 , C═NR, C═NAr′, C═C(R) 2 , O, S, Se, S═O, or SO 2 , where the symbols R and Ar′ have the definition set out in claim 20 ,
the symbol o represents the sites of attachment,
and the further symbols are defined as follows:
m is 0, 1, 2, 3 or 4;
n is 0, 1, 2 or 3;
j is 0, 1 or 2.
32 . The compound as claimed in claim 20 , comprising at least one structure of the formulae (VII-1) to (VII-9), where the compounds have at least one fused ring,
where the symbols Z 1 , Z 2 , Z 3 , R a and R b have the definitions given in claim 20 ,
Z 4 , Z 5 is the same or different at each instance and is N or B;
R c , R d , R e , R f is the same or different at each instance and is H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(═O)OAr′, C(═O)OR 1 , C(═O)N(Ar′) 2 , C(═O)N(R 1 ) 2 , C(Ar′) 3 , C(R 1 ) 3 , Si(Ar′) 3 , Si(R 1 ) 3 , B(Ar′) 2 , B(R 1 ) 2 , C(═O)Ar′, C(═O)R 1 , P(═O)(Ar′) 2 , P(═O)(R 1 ) 2 , P(Ar′) 2 , P(R 1 ) 2 , S(═O)Ar′, S(═O)R 1 , S(═O) 2 Ar′, S(═O) 2 R 1 , OSO 2 Ar′, OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 carbon atoms, where the alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl group may be substituted in each case 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═O, C═S, C═Se, C═NR 1 , —C(═O)O—,
—C(═O)NR 1 —, NR 1 , P(═O)(R 1 ), —O—, —S—, SO or SO 2 , or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R 1 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R 1 radicals; at the same time, two R c , R d , R e , R f radicals may also form a ring system together or with a further group, where the R 1 radical has the definition given in claim 20 ,
Y 3 , Y 4 is the same or different at each instance and is N(Ar′), N(R), P(Ar′), P(R), P(═O)Ar′, P(═O)R, P(═S)Ar′, P(═S)R, B(Ar′), B(R), Al(Ar′), Al(R), Ga(Ar′), Ga(R), C═O, C(R) 2 , Si(R) 2 , C═NR, C═NAr′, C═C(R) 2 , O, S, Se, S═O, or SO 2 , where the symbols R and Ar′ have the definition set out in claim 20 ,
the symbol o represents the sites of attachment,
and the further symbols are defined as follows:
m is 0, 1, 2, 3 or 4;
n is 0, 1, 2 or 3;
j is 0, 1 or 2.
33 . An oligomer, polymer or dendrimer containing one or more compounds as claimed in claim 20 , wherein, rather than a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.
34 . A formulation comprising at least one compound as claimed in claim 20 and at least one further compound.
35 . A composition comprising at least one compound as claimed in claim 20 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that exhibit TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.
36 . A process for preparing a compound as claimed in claim 20 , comprising synthesizing a base skeleton having at least one of the Z 2 , Z 3 groups or a precursor of one of the Z 2 , Z 3 groups, and introducing the Z 1 group by means of a metalation reaction, a nucleophilic aromatic substitution reaction or a coupling reaction.
37 . A method comprising providing the compound as claimed in claim 20 and including the compound in an electronic device.
38 . An electronic device comprising at least one compound as claimed in claim 20 .