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(19) United States (12) Patent Application Publication (10) Pub US 20120319052A1 (19) United States (12) Patent Application Publication (10) Pub. N0.: US 2012/0319052 A1 Brocke et al. (43) Pub. Date: Dec. 20, 2012 (54) COMPOUNDS FOR ELECTRONIC DEVICES Publication Classi?cation (75) Inventors: Constanze Brocke, Gross-Gerau (DE); (51) Int. Cl. Christof P?umm, Darmstatd (DE); H01 B 1/12 (2006.01) Amir Hossain Parham, Frankfurt am C07D 513/00 (200601) Main (DE); Rocco Fortte, Frankfurt am C08G 73/06 (200601) Main (DE) C07D 401/10 (2006.01) . _ (52) US. Cl. .......... .. 252/500; 546/102; 546/58; 546/38; (73) Asslgnee. Merck Patent GmbH, Darmstadt (DE) 544/14; 526/259; 526/257 (21) Appl. N0.: 13/581,543 (22) PCT Filed: Jan. 21, 2011 (57) ABSTRACT (86) PCT N0.: PCT/EP2011/000235 The present invention relates to compounds of the formula (1) (2)’§371(c)(1), (4) Date: Aug 28, 2012 or ( 2 ) d to h e use h ereo f.in'e 1 ectronic. devices, . an d to electromc devices Wh1ch comprise these compounds. The (30) Foreign Application Priority Data invention furthermore relates to the preparation of the com pounds of the formula (1) or (2) and to formulations compris Mar. 2, 2010 (DE) .................... .. 10 2010 009 903.1 ing one or more compounds of the formula (1) or (2). US 2012/0319052 A1 Dec. 20, 2012 COMPOUNDS FOR ELECTRONIC DEVICES materials in electronic devices. In the triarylamine com pounds, the individual aryl groups are bridged to one another [0001] The present invention relates to compounds of the formula (1) or (2) and to the use thereof in electronic devices, in a de?ned manner and are additionally substituted by car and to electronic devices Which comprise these compounds. baZole derivatives. HoWever, the compounds disclosed The invention furthermore relates to the preparation of the therein contain three carbaZole groups, Which are arranged compounds of the formula (1) or (2) and to formulations symmetrically around the central triarylamine group. comprising one or more compounds of the formula (1) or (2). [0011] Bridged triarylamine derivatives are furthermore [0002] The compounds of the formula (1) or (2) are used in disclosed in the application WO 2010/083871. accordance With the invention in electronic devices, prefer ably in organic electroluminescent devices (OLEDs). The [0012] HoWever, there continues to be a demand for func general structure of these devices is described, for example, in tional materials for use in OLEDs Which preferably effect Us. Pat. No. 4,539,507, US Pat. No. 5,151,629, EP improvements in relation to the performance data of the elec 0676461 and WO 98/27136. tronic devices, in particular in relation to the lifetime and [0003] Hole-transport and -injection materials Which are ef?ciency of the devices. knoWn from the prior art for organic electroluminescent devices are, inter alia, arylamine compounds. Materials of [0013] In particular, there is a demand for compounds this type based on an indeno?uorene skeleton are disclosed, Which have high hole mobility. This facilitates a loW depen for example, in WO 2006/ 100896 and WO 2006/ 122630. dence of the operating voltage on the thickness of the hole [0004] HoWever, the hole-transport materials knoWn from transport layer, Which represents a highly desirable property. the prior art frequently have loW electron stability, Which Furthermore, there is a demand for oxidation- and tempera reduces the lifetime of electronic devices comprising these ture-stable compounds, since this improves the proccessabil compounds. Overall, further improvements are desirable ity on use in electronic devices. With respect to the ef?ciency of ?uorescent organic electrolu [0014] The present invention provides compounds of the minescent devices and the lifetime, especially in the case of formula (1) and (2) in order to achieve the technical object blue-?uorescent devices. There is also potential for improve described above. ment in the operating voltage of the electronic devices. [0005] There is therefore a demand for alternative com [0015] The invention thus relates to a compound of the pounds Which can be used, inter alia, as hole-transport mate formula (1) or (2) rials in organic electroluminescent devices and Which prefer ably effect an improvement in the above-mentioned performance data of the devices. formula (1) [0006] Matrix materials Which are knoWn from the prior art for phosphorescent dopants are, inter alia, carbaZole deriva tives, for example bis(carbaZolyl)-biphenyl. The use of ketones (WO 2004/093207), phosphine oxides and sulfones (WO 2005/003253) as matrix materials for phosphorescent dopants is furthermore known. Metal complexes, for example BAlq or Zinc(II) bis[2-(2-benZothiaZolyl)phenolate], are also used as matrix materials for phosphorescent dopants. [0007] HoWever, there continues to be a demand for alter native matrix materials for phosphorescent dopants, in par ticular those Which effect an improvement in the performance data of the electronic devices. [0008] Also of particular interest is the provision of alter native materials as matrix components of mixed-matrix sys tems. A mixed-matrix system in the sense of this application formula (2) is taken to mean a system in Which tWo or more different matrix compounds are used as a mixture together With one (or more) dopant compounds in an emitting layer. These systems are, in particular, of interest in the case of phosphorescent organic electroluminescent devices. For more detailed infor mation, reference is made to the application WO 2010/ 108579. [0009] Compounds knoWn from the prior art Which may be mentioned as matrix components in mixed-matrix systems are, inter alia, CBP (biscarbaZolylbiphenyl) and TCTA (tri scarbaZolyltriphenylamine) (?rst component). Suitable as the second component are compounds such as, for example, benZophenone derivatives, diaZaphospholes (see the applica tion WO 2010/054730) and triaZines. HoWever, there contin ues to be a demand for alternative compounds for use as matrix components in mixed-matrix systems. In particular, there is a demand for compounds Which effect an improve ment in the operating voltage and lifetime of the electronic devices. [0010] The applications WO 2007/031165 and WO 2006/ 033563 disclose triarylamine derivatives for use as functional US 2012/0319052 A1 Dec. 20, 2012 Where the following applies to the symbols and indices occur stituted by one or more radicals R1, or a combination of ring: these systems, Where tWo or more radicals R may be [0016] W is on each occurrence equal to Z, linked to one another and may form a ring; [0017] Where a unit comprising tWo adjacent groups [0023] R1 is, identically or differently on each occur W may optionally be replaced by a group of the for rence, H, D, F, Cl, Br, I, CHO, N(R2)2, C(:O)R2, mula (3) P(:0)(R2)2, S(:O)R2, S(:0)2R2, CR2:C(R2)2, CN, N02, Si(R2)3, B(OR2)2, OSO2R2, OH, COOR2, CON(R2)2, a straight-chain alkyl, alkoxy or thioalkyl formula (3) 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 may be substituted by one or more radi cals R2, Where one or more non-adjacent CH2 groups may be replaced by iR2C:CR2i, 4CECi, Si(R2) [0018] Where the group of the formula (3) is arranged 2, Ge(R2)2, Sn(R2)2, C:O, C:S, C:Se, C:NR2, in such a Way that the bond betWeen the C atoms P(:O)(R2), SO, S02, NR2, iOi, iSi, iCOOi or iCONRzi and Where one or more H atoms may be labelled With * is condensed onto the six-membered replaced by D, F, Cl, Br, 1, CN or N02, or an aromatic or ring of the carbaZole derivative; heteroaromatic ring system having 5 to 60 aromatic ring [0019] X is a divalent group selected from C(R)2, Si(R)2, atoms, Which may in each case be substituted by one or NR, PR, P(:O)R, BR, 0, S, C:O, C:S, C:NR, more radicals R2, or an aryloxy or heteroaryloxy group 8:0 and S(:O)2, having 5 to 60 aromatic ring atoms, Which may be sub [0020] Z is selected on each occurrence, identically or stituted by one or more radicals R2, or a combination of differently, from CR and N, or is equal to C if a substitu these systems, Where tWo or more radicals Rl may be ent is bonded to the group Z; linked to one another and may form a ring; [0021] L is on each occurrence, identically or differently, [0024] R2 is, identically or differently on each occur a divalent group selected from C(R)2, Si(R)2, NR, PR, rence, H, D, F or an aliphatic, aromatic and/or heteroaro P(:O)R, BR, 0, S, C:O, C:S, C:NR, C:C(R)2, matic organic radical having 1 to 20 C atoms, in Which, 8:0, S(:O)2 and CR:CR; in addition, one or more H atoms may be replaced by D [0022] R is, identically or differently on each occur or F; tWo or more substituents R2 here may also be linked rence, H, D, F, Cl, Br, I, CHO, N(Rl)2, C(:O)Rl, P(:0)(R1)2, S(:0)R1, S<:0)2R1, CR1:C(R1)2, to one another and may form a ring; CN, N02, Si(Rl)3, B(ORl)2, OSOZRI, OH, COORl, [0025] i is equal to 0, 1 or 2, Where, for i:0, the tWo CON(Rl)2, a straight-chain alkyl, alkoxy or thioalkyl groups Which are bonded to the group With the index i are connected directly to one another; group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms [0026] j is equal to 0, 1 or 2, Where, for jIO, the tWo or an alkenyl or alkynyl group having 2 to 40 C atoms, groups Which are bonded to the group With the index j each of Which may be substituted by one or more radi are connected directly to one another; cals R1, Where one or more non-adjacent CH2 groups [0027] k is equal to 0 or 1, Where, for k:0,
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