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US 11,447,464 B2Granted
Compounds with spirobifluorene-structures
AssigneeMerck Patent GmbH
InventorsAmir Parham, Tobias Grossmann, Aurélie Ludemann, Dominik Joosten, Jonas Kroeber
Life of this patent
Estimating the term…
Abstract
The invention relates to spirobifluorene derivatives which are substituted with electron transport groups, in particular for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention, and to electronic devices comprising the same.
Claims15
A compound comprising structures of the formula (I):
- where the symbols used are as follows:
- Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 is the same or different and is Y or C;
- Y is the same or different at each instance and is N, CR1, or two adjacent Y groups together are O, S, NR1, with the proviso that a 5- or 6-membered ring is formed;
- X is the same or different at each instance and is N or CR1;
- o, p, q, r is 0 or 1;
- L is a bond or an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may be substituted by one or more R1 radicals;
- Q is an electron transport group;
- R1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR2)2, CHO, C(═O)R2, CR2═C(R2)2, CN, C(═O)OR2, C(═O)N(R2)2, Si(R2)3, NO2, P(═O)(R2)2, OSO2R2, OR2, S(═O)R2, S(═O)2R2, 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 R5 radicals, where one or more nonadjacent CH2 groups may be replaced by —R2C≡CR2—, —C≡C—, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C≡NR2, P(═O)(R2), —C(═O)O—, —C(═O)NR2—, —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems;
- at the same time, two or more R1 radicals together may form a ring system;
- R2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR3)2, CHO, C(═O)R3, CR3═C(R3)2, CN, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, 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 R3 radicals, where one or more nonadjacent CH2 groups may be replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), —C(═O)O—, —C(═O)NR3—, —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or or a combination of these systems;
- at the same time, two or more R2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
- R3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F;
- at the same time, two or more R3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
- with the proviso that o+p=1, where, if o=1, Z1, Z2 are C and Z3, Z4 are Y, and, if p=1, Z1, Z2 are Y and Z3, Z4 are C;
- and
- with the proviso that q+r=1 where, if q=1, Z5, Z6 are C and Z7, Z8 are Y and, if r=1, Z5, Z6 are Y and Z7, Z8 are C.
13 more elements
A compound comprising structures of the formula (I):
- where the symbols used are as follows:
- Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 is the same or different and is Y or C;
- Y is the same or different at each instance and is N, CR1, or two adjacent Y groups together are O, S, NR1, with the proviso that a 5- or 6-membered ring is formed;
- X is the same or different at each instance and is N or CR1;
- o, p, q, r is 0 or 1;
- L is a bond or an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may be substituted by one or more R1 radicals;
- Q group is selected from structures of the formulae (Q-16), (Q-17) or (Q-18)
- where the dotted bond marks the attachment position and
- Ar1 is 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 adjacent R1 substituents may optionally form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R3 radicals;
- R1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR2)2, CHO, C(═O)R2, CR2═C(R2)2, CN, C(═O)OR2, C(═O)N(R2)2, Si(R2)3, N(R2)2, NO2, P(═O)(R2)2, OSO2R2, OR2, S(═O)R2, S(═O)2R2, 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 R5 radicals, where one or more nonadjacent CH2 groups may be replaced by —R2C═CR2-, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, NR2, P(═O)(R2), —C(═O)O—, —C(═O)NR2—, —O—, —s-, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems;
- at the same time, two or more R1 radicals together may form a ring system;
- R2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR3)2, CHO, C(═O)R3, CR3═C(R3)2, CN, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, 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 R3 radicals, where one or more nonadjacent CH2 groups may be replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, NR3, P(═O)(R3), —C(═O)O—, —C(═O)NR3—, —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of these systems;
- at the same time, two or more R2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
- R3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F;
- at the same time, two or more R3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
- with the proviso that o+p=1, where, if o=1, Z1, Z2 are C and Z3, Z4 are Y, and if p=1, Z1, Z2 are Y and Z3, Z4 are C;
- and
- with the proviso that q+r=1 where, if q=1, Z5, Z6 are C and Z7, Z8 are Y and, if r=1, Z5, Z6 are Y and Z7, Z8 are C.
15 more elements
An oligomer, polymer or dendrimer containing one or more compounds
- comprising structures of the formula (I):
- where the symbols used are as follows:
- Z1, Z2, Z3, Z4, Z5, Z6, Z7, Z8 is the same or different and is Y or C;
- Y is the same or different at each instance and is N, CR1, or two adjacent Y groups together are O, S, NR1, with the proviso that a 5- or 6-membered ring is formed;
- X is the same or different at each instance and is N or CR1;
- o, p, q, r is 0 or 1;
- L is a bond or an aromatic or heteroaromatic ring system which has 5 to 24 aromatic ring atoms and may be substituted by one or more R1 radicals;
- Q is an electron transport group;
- R1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR2)2, CHO, C(═O)R2, CR2═C(R2)2, CN, C(═O)OR2, C(═O)N(R2)2, Si(R2)3, N(R2)2, NO2, P(═O)(R2)2, OSO2R2, OR2, S(═O)R2, S(═O)2R2, 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 R5 radicals, where one or more nonadjacent CH2 groups may be replaced by —R2C═CR2—, —C≡C—, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, NR2, P(═O)(R2), —C(═O)O—, —C(═O)NR2—, —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of these systems;
- at the same time, two or more R1 radicals together may form a ring system;
- R2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR3)2, CHO, C(═O)R3, CR3═C(R3)2, CN, C(═O)OR3, C(═O)N(R3)2, Si(R3)3, N(R3)2, NO2, P(═O)(R3)2, OSO2R3, OR3, S(═O)R3, S(═O)2R3, 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 R3 radicals, where one or more nonadjacent CH2 groups may be replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, NR3, P(═O)(R3), —C(═O)O—, —C(═O)NR3—, —O—, —S—, SO or SO2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, 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 R3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of these systems;
- at the same time, two or more R2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
- R3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F;
- at the same time, two or more R3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system;
- with the proviso that o+p=1, where, if o=1, Z1, Z2 are C and Z3, Z4 are Y, and if p=1, Z1, Z2 are Y and Z3, Z4 are C;
- and
- with the proviso that q+r=1 where, if q=1, Z5, Z6 are C and Z7, Z8 are Y and, if r=1, Z5, Z6 are Y and Z7, Z8 are C,
- wherein, rather than a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.
15 more elements
Dependencies are inferred from the claim text.