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US 9,029,425 B2Granted
Substituted dibenzo[FG,OP]tetracenes and formulations or electronic devices containing the same
AssigneeMerck Patent GmbH
InventorsThomas Eberle, Rémi Manouk Anémian, Sigurd Hoeger, Vanessa Bobbe, Anna Jochemich
Life of this patent
Estimating the term…
Abstract
The present invention is directed to a compound of the formula (2) and its uses thereof: wherein T, U, V and W is CR1; R1 is H; X, is CR2 and N with the proviso that at least one X is equal to CR2 and at least one R2 from CR2 is equal to Z; and n and m are 0, 1, 2, 3 to 4 and either n is at least 3 or m is at least 3.
Claims19
A compound of the formula (2):
- wherein
- T, U, V and W are, on each occurrence, CR1;
- R1 is H;
- X, identically or differently on each occurrence, is CR2 or N with the proviso that at least one X is equal to CR2 and at least one R2 from CR2 is equal to Z, where Z is independently phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, pyrrolyl, thiophenyl, furanyl, naphthalenyl, quinolinyl, isoquinolinyl, quinoxalinyl, indolyl, benzothiophenyl or benzofuranyl,
- and when R2 is not Z, then R2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups may be replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R3, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3, or a combination of two or more of these groups;
- or two or more adjacent radicals R2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- R3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 40 C atoms, where one or more H atoms is optionally replaced by F;
- or two or more substituents R3 optionally form a monocyclic or polycyclic, aliphatic or aromatic ring system with one another;
- n and m are independently 0, 1, 2, 3 or 4 and either n is at least 3 or m is at least 3;
- where, in the case where a six-membered ring occurs n times, n of the groups T are equal to CR1 and the n six-membered rings replace the radicals R1 of CR1, and, in the case where a six-membered ring occurs m times, m of the groups U are equal to CR1 and the m six-membered rings replace the radicals R1 of CR1.
7 more elements
A compound of the formula (2):
- wherein
- T, U, V and W are, on each occurrence, CR1;
- R1 is H;
- X, identically or differently on each occurrence, is CR2 or N with the proviso that at least one X is equal to CR2 and at least one R2 from CR2 is equal to Z,
- where Z is selected from formula (34), formula (35), formula (36), formula (37), formula (38), formula (39), formula (40), formula (41), formula (42), formula (43), formula (44), formula (45), formula (46), formula (47) or formula (48);
- wherein Y is on each occurrence, identically or differently, CR3, N, P or P(R3)2;
- wherein
- R3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 40 C atoms, where one or more H atoms is optionally replaced by F;
- or two or more substituents R3 optionally form a monocyclic or polycyclic, aliphatic or aromatic ring system with one another;
- and when R2 is not Z, then R2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R3, where one or more non-adjacent CH2 groups may be replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R3, or an aryloxy, arylalkoxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R3, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R3, or a combination of two or more of these groups;
- or two or more adjacent radicals R2 here may form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- n and m are independently 0, 1, 2, 3 or 4 and either n is at least 3 or m is at least 3;
- where, in the case where a six-membered ring occurs n times, n of the groups T are equal to CR1 and the n six-membered rings replace the radicals R1 of CR1, and, in the case where a six-membered ring occurs m times, m of the groups U are equal to CR1 and the m six-membered rings replace the radicals R1 of CR1.
10 more elements
Dependencies are inferred from the claim text.