发明名称 Materials for organic electroluminescent devices
摘要 The present invention relates to organic electroluminescent devices which comprise fluorene derivatives and spiro bifluorene derivatives as matrix material for phosphorescent emitters.
申请公布号 US9199972(B2) 申请公布日期 2015.12.01
申请号 US201013510143 申请日期 2010.10.28
申请人 Merck Patent GmbH 发明人 Parham Amir Hossain;Kaiser Joachim;Gerhard Anja;Kroeber Jonas Valentin;Anémian Rémi Manouk
分类号 H01L51/50;C07D403/10;C07D403/14;C07D471/04;C07D487/04;C07D519/00;C09K11/06;H05B33/14;C09B57/00;C09B57/10;H01L51/00 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), (2), (3a) or (3b), where the following applies to the symbols and indices used: Ar is on each occurrence, identically or differently, a heteroaryl group selected from the group consisting of triazine, pyrazine, pyrimidine, pyridazine, pyridine, pyrazole, imidazole, oxazole, 1,3,4-oxadiazole, benzimidazole or thiazole, each of which is optionally substituted by one or more groups R1; X is a group of the formula (4), where the dashed bond in each case indicates the bond to the two benzene rings: or X is on each occurrence, identically or differently, a divalent bridge selected from B(Ar2), C(Ar2)2, C(Ar1Ar2), Si(Ar2)2, C═C(Ar2)2 or C═NAr2; X1 is on each occurrence, identically or differently, X or a divalent bridge selected from B(R1), C(R1)2, Si(R1)2, C═C(R1)2, C═NR1, B(Ar1), C(Ar1)2, Si(Ar1)2, C═C(Ar1)2 or C═NAr1; R1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Ar1)2, C(═O)Ar1, P(═O)(Ar1)2, S(═O)Ar1, S(═O)2 Ar1,CR2═CR2Ar1, CN, NO2, Si(R2)3, B(OR2)2, B(R2)2, B(N(R2)2), OSO2R2, 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 or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R2, where one or more, preferably 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, 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 R2, or an aryloxy or hetero-aryloxy 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 is optionally substituted by one or more radicals R2; two or more adjacent substituents R1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; Ar1 is 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 R2; two radicals Ar1 which are bonded to the same nitrogen, phosphorus or boron atom may here also be linked to one another by a single bond or a bridge selected from B(R2), C(R2)2, Si(R2)2, C═O, C═NR2, C═C(R2)2, O, S, S═O, SO2, N(R2), P(R2) and P(═O)R2; R2is on each occurrence, identically or differently, H, D or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, H atoms is optionally replaced by D or F; two or more adjacent substituents R2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; n is 0 or 1; m is 0, 1,2 or 3; o is 0, 1, 2, 3 or 4 if m=0 and is 0, 1, 2 or 3 if m=1; p, q are on each occurrence, identically or differently, 0 or 1, with the proviso that p+q is equal to 1 or 2; where the compound of the formula (1), (2), (3a) or (3b) contains at least one group Ar2, where Ar2 is selected from a carbazole group, an azacarbazole group, a cis- or trans-indenocarbazole group, a cis- or trans-indenoazacarbazole group or a cis- or trans-indolocarbazole group, each of which is optionally substituted by one or more radicals R1, where two or more adjacent substituents R1, together with the atoms to which they are bonded, may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another, with the proviso that the group Ar2is not in conjugation with the group Ar.
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