Polycyclic compounds for organic electroluminescent devices
The present invention relates to polycyclic compounds suitable for use in electronic devices, and to electronic devices, especially organic electroluminescent devices, comprising these compounds.
1 . A compound comprising at least one structure of the formula (I)
where the symbols and indices used are as follows:
Z is the same or different at each instance and is N or B;
Q is the same or different at each instance and is C═O, C(═O)—C(═O), (R d ) 2 C—C(R d ) 2 , (R d )C═C(R d ) or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and binds to the Y 1 and Y 2 groups via two adjacent and mutually bonded carbon atoms and may be substituted in each case by one or more R d radicals;
Y 1 , Y 2 is the same or different at each instance and is N(Ar), N(R), B(Ar), B(R), Al(Ar) or Al(R);
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 ;
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 an Ar or R radical;
X 1 is the same or different at each instance and is N, CR a , CAr, or C if a ring system is formed by a bond to an Ar or R radical, 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, CR b or CAr, with the proviso that not more than two of the X 1 , X 2 groups in one cycle are N;
X 3 is the same or different at each instance and is N, CR c , CAr, or C if a ring system is formed by a bond to an Ar or R radical;
R, R a , R b , R c , R d 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′, OSOR 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—, —Se—, —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 , R c , R d radicals may also form a ring system together;
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 wherein said bridge is selected from the group consisting of a single bond, 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 group 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, each of which may be substituted 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; 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.
2 . The compound as claimed in claim 1 , comprising at least one structure of the formula (II)
where Y 1 , Y 2 , Y 3 , Y 4 , Z, Q, R a , R b and R c have the definitions given in claim 1 and the index j is 0, 1 or 2.
3 . The compound of claim 1 , comprising at least one structure of the formulae (IIIa) to (IIIk):
where Y 1 , Y 2 , Y 3 , Y 4 , X 1 , X 2 , X 3 , R d and Z have the definitions given in claim 1 , X 4 is the same or different at each instance and is N, CR d , or C if a ring system is formed by a bond to an Ar or R radical, and Y 5 is C(R) 2 , NR, NAr′, BR, BAr′, O or S, where R and Ar′ have the definitions given in claim 1 .
4 . The compound as claimed in claim 1 , comprising at least one structure of the formula (IVa) to (IVn):
where Y 1 , Y 2 , Y 3 , Y 4 , Z, R a , R b , R c and R d have the definitions given in claim 1 , the index j is 0, 1 or 2, the index m is 0, 1, 2, 3 or 4, and Y 5 is C(R) 2 , NR, NAr′, BR, BAr′, O or S, where R and Ar′ have the definitions given in claim 1 .
5 . The compound as claimed in claim 1 , wherein Z is N and at least one of the Y 1 , Y 2 groups is B(Ar), B(R), Al(Ar), or Al(R).
6 . The compound as claimed in claim 1 , wherein Z is N and at least one of the Y 1 , Y 2 groups is N(Ar) or N(R).
7 . The compound as claimed in claim 1 , wherein at least one of the Y 1 , Y 2 groups represent(s) N(Ar) or N(R) and at least one of the Y 3 , Y 4 groups is B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), P(═O)Ar, P(═O)R, C═O, S═O or SO 2 .
8 . The compound as claimed in claim 1 , wherein Z is B and at least one of the Y 1 , Y 2 groups is N(Ar) or N(R).
9 . The compound as claimed in claim 1 , wherein Z is B and at least one of the Y 1 , Y 2 groups is B(Ar), B(R), Al(Ar), or Al(R).
10 . The compound as claimed in claim 1 , wherein at least one of the Y 1 , Y 2 groups represents B(Ar), B(R), Al(Ar) or Al(R) and at least one of the Y 3 , Y 4 groups is N(Ar), N(R), P(Ar), P(R), O, S or Se.
11 . The compound as claimed in claim 1 , comprising at least one structure of the formulae (Va) to (Vk):
where Y 3 , Y 4 , X 1 , X 2 , X 3 and Z have the definitions given in claim 1 ,
X 4 is the same or different at each instance and is N, CR d , or C if a ring system is formed by a bond to an Ar or R radical,
Y 5 is C(R) 2 , NR, NAr′, BR, BAr′, O or S, where R and Ar′ have the definitions given in claim 1 :
Z 1 , Z 2 is the same or different at each instance and is N, B or Al;
X is the same or different at each instance and is N, CR, or C if a ring system is formed by a bond to an X 3 radical, with the proviso that not more than two of the X groups in one cycle are N, where R is as defined in claim 1 ;
Y 6 , Y 7 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 R and Ar′ have the definitions given in claim 1 ;
p, q is the same or different at each instance and is 0 or 1, where 0 means that the corresponding group is absent.
12 . The compound as claimed in claim 1 , comprising at least one structure of the formulae (VI-1) to (VI-39):
where Y 3 , Y 4 , Z, R, R a , R b , R c and R d have the definitions given in claim 1 , and the further symbols have the following definition:
Z 1 , Z 2 is the same or different at each instance and is N, B or Al;
l is 0, 1, 2, 3, 4 or 5;
m is 0, 1, 2, 3 or 4;
j is 0, 1 or 2;
k is 0 or 1; and
Y 5 is C(R) 2 , NR, NAr′, BR, BAr′, O or S, where R and Ar′ have the definitions given in claim 1 .
13 . The compound as claimed in claim 1 , comprising at least one structure of the formulae (VII-1) to (VII-18):
where Z, R, R a , R b , R c and R d have the definitions given in claim 1 , and the further symbols have the following definition:
Z 1 , Z 2 , Z 3 , Z 4 is the same or different at each instance and is N, B or Al;
l is 0, 1, 2, 3, 4 or 5;
m is 0, 1, 2, 3 or 4;
j is 0, 1 or 2;
k is 0 or 1.
14 . The compound as claimed in claim 1 , wherein at least two R, R a , R b , R c , R d radicals to which the two R, R a , R b , R c , R d radicals bind form a fused ring, where the two R, R a , R b , R c , R d 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 via which the two R, R a , R b , R c , R d radicals bind, and the further symbols have the following definition:
Y 8 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 e 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 in each case 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 1 ), —O—, —S—, SO or SO 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 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, two R e radicals, or one R e radical with an R 1 radical, may also form a ring system, where R 1 and R 2 have the definitions given in claim 1 ;
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.
15 . An oligomer, polymer or dendrimer containing one or more compounds as claimed in claim 1 , wherein, in place of a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.
16 . A formulation comprising at least one compound as claimed in claim 1 and at least one further compound.
17 . A composition comprising at least one compound as claimed in claim 1 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.
18 . A process for preparing a compound as claimed in claim 1 , comprising synthesizing a base skeleton having a Z group or a precursor of the Z group, and introducing at least one of the Y 1 , Y 2 , Y 3 , Y 4 groups by means of a nucleophilic aromatic substitution reaction or a coupling reaction.
19 . A method comprising providing at least one compound as claimed in claim 1 and including the compound in an electronic device.
20 . An electronic device comprising at least one compound as claimed in claim 1 .