发明名称 Materials for organic electroluminescent devices
摘要 The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.
申请公布号 US9593087(B2) 申请公布日期 2017.03.14
申请号 US201113805943 申请日期 2011.05.30
申请人 Merck Patent GmbH 发明人 Breuning Esther;Becker Heinrich;Pan Junyou;Buchholz Herwig;Mujica-Fernaud Teresa;Martynova Irina
分类号 H01L51/50;C07D251/22;C07D251/24;C07D251/42;C07D403/12;C07D409/12;C07D409/14;C07D487/04;C07D487/16;C09K11/06;H01L51/00;H05B33/10;H05B33/14;C07D403/14;C07F7/10 主分类号 H01L51/50
代理机构 Drinker Biddle & Reath LLP 代理人 Drinker Biddle & Reath LLP
主权项 1. A compound of the formula (1), where the following applies to the symbols and indices used: Ar1 and Ar2 are identically or differently on each occurrence, a group of the following formula(3)-formula(8) or formula(10)-formula(12) where the dashed bond indicates the bond to the nitrogen; Ar3 and Ar4 are on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R; with the proviso that Ar3 and Ar4 contain no amino groups and no carbazole groups bonded via N; L is a single bond or a divalent straight-chain alkylene, alkylidene, alkyleneoxy or thioalkyleneoxy group having 1 to 40 C atoms or a branched or cyclic alkylene, alkylidene, alkyleneoxy or thioalkyleneoxy group having 3 to 40 C atoms, which is optionally substituted by in each case one or more radicals R, where one or more CH2 groups, is optionally replaced by Si(R)2, Ge(R)2, Sn(R)2, C═O, C═S, C═Se, C═NR, P(═O)R, S═O, SO2, —O—, —S— or —CONR— and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or a divalent aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R and which contains no amino groups and no carbazole groups bonded via N, or Si(R)2, Ge(R)2, O, S, C(═O), S(═O), SO2, PR, P(═O)(R), P(═S)(R) or a combination of two, three, four or five of these systems; R is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, C(═O)Ar, C(═O)R2, P(═O)(Ar)2, B(R2)2, B(OR2)2, Si(R2)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally 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), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, 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 R2 and which contains no amino groups and no carbazole groups bonded via N, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, where two or more adjacent substituents R may optionally form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R2; R1 is selected on each occurrence, identically or differently, from the group consisting of D, F, Br, I, CN, NO2, C(═O)Ar, C(═O)R2, P(═O)(Ar)2, B(R2)2, B(OR2)2, Si(R2)3, a straight-chain alkyl or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more non-adjacent CH2 groups is optionally 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), SO, SO2, NR2, O, S or CONR2 and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, 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 R2 and which contains no amino groups and no carbazole groups bonded via N, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R2, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, where two or more adjacent substituents R may optionally form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R2; with the proviso that R1 contains no condensed aryl groups; R2 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, Cl, Br, I, CN, NO2, C(═O)Ar, C(═O)R3, P(═O)(Ar)2, B(R3)2, B(OR3)2, Si(R3)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R3, where one or more non-adjacent CH2 groups is optionally 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 is optionally replaced by D, F, Cl, Br, I, CN or NO2, 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 and which contains no amino groups and no carbazole groups bonded via N, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R3, where two or more adjacent substituents R2 may optionally form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system, which is optionally substituted by one or more radicals R3; Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5-30 aromatic ring atoms, which is optionally substituted by one or more non-aro-matic radicals R3; two radicals Ar which are bonded to the same P atom may also be bridged to one another here by a single bond or a bridge selected from N(R3), C(R3)2, O or S; R3 is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms is optionally replaced by D, F, Cl, Br, I or CN, where two or more adjacent substituents R3 may form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another; n is 0 or 1; wherein at least one radical R1 stands for an aromatic or heteroaromatic ring system and/or in that Ar3 represents an aromatic or heteroaromatic ring system having at least two aryl or heteroaryl groups and/or in that n=1 and thus one group Ar4 is present; the following compounds are excluded from the invention:
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