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(12) Patent Application Publication (10) Pub. No.: US 2015/0340627 A1 JATSCH Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2015/0340627 A1 JATSCH Et Al US 2015 0340627A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0340627 A1 JATSCH et al. (43) Pub. Date: Nov. 26, 2015 (54) MATERIALS FOR ELECTRONIC DEVICES C07D40 L/04 (2006.01) C08G 6/12 (2006.01) (71) Applicant: MERCK PATENT GMBH, Darmstadt C07D 403/2 (2006.01) (DE) C07D 403/4 (2006.01) (72) Inventors: Anja JATSCH, Frankfurt Am Main C07D40 L/4 (2006.01) (DE); Christof PFLUMM, Darmstadt C07D 209/94 (2006.01) Frankfurt Am Main (DE); Thomas EBERLE, Landau (DE); Philipp (52) U.S. Cl. STOESSEL, Frankfurt Am Main (DE); CPC .......... HOIL 51/0072 (2013.01); C07D 209/94 Jonas Valentin KROEBER, Frankfurt (2013.01); C07D 209/86 (2013.01); C07D Am Main (DE); Rouven LINGE, 401/04 (2013.01); C07D 487/04 (2013.01); Darmstadt (DE) C07D 403/12 (2013.01); C07D 403/14 (21) Appl. No.: 14/758,978 stoo,2013.01); O 3.01); C07D HOIL 401/14 so (2013.01); tleHOIL (22) PCT Filed: Dec. 10, 2013 HOIL 51/0058 (2013.01); HOIL 51/006 (2013.01); HOIL 51/0061 (2013.01); C08G (86). PCT No.: PCT/EP2013/003722 61/124 (2013.01); C08G 2261/3241 (2013.01); S371 (c)(1), C08G 2261/3221 (2013.01); C08G 2261/312 (2) Date: Jul. 2, 2015 (2013.01); C08G 2261/314 (2013.01); C08G 2261/3142 (2013.01); C08G 2261/95 (2013.01); (30) Foreign Application Priority Data C08G 2261/5.14 (2013.01); C08G 2261/3162 Jan. 3, 2013 (EP) .................................. 13OOOO13.6 (2013.01); HOIL 5 1/5024 (2013.01) Publication Classification (57) ABSTRACT (51) Int. Cl. The present application relates to a compound of a formula HOIL 5L/00 (2006.01) (I), (II) or (III). The compound can be used in an electronic CO7D 209/86 (2006.01) device, preferably an organic electronic device. US 2015/0340627 A1 Nov. 26, 2015 MATERALS FOR ELECTRONIC DEVICES ticular in the aspects operating Voltage and power efficiency 0001. The present application relates to a compound of a of devices comprising the compounds. formula (I), (II) or (III) which contains a carbazole group and 0013 Surprisingly, it has now been found that excellent an electron-deficient heteroaryl group. The compound can be values for operating Voltage and power efficiency can be used in an electronic device, preferably an organic electronic achieved with compounds which contain a carbazole group or device. The present application furthermore relates to a pro indenocarbazole group which are connected to a donor-Sub cess for the preparation of the compound. stituted electron-deficient six-membered heteroaromatic ring 0002 Electronic devices in the sense of this application via a linker group on the Natom. are taken to mean, in particular, so-called organic electronic devices, which comprise organic semiconductor materials as 0014. The present application thus relates to a compound functional materials. They are again taken to mean, in par of a formula (I), (II) or (III) ticular, organic electroluminescent devices (OLEDs) and other electronic devices which are mentioned below in the detailed description of the invention. formula (I) 0003. The precise structure of OLEDs is described, inter R4 alia, in U.S. Pat. No. 4,539,507, U.S. Pat. No. 5,151,629, EP 0676461 and WO 98/27136. In general, the term OLED is CBZ taken to mean electronic devices which comprise at least one formula (II) organic material and emit light on application of an electrical Voltage. f R1 R1 0004. In the case of electronic devices, in particular Z N Z Z N Z OLEDs, there is great interest in improving the performance data, in particular lifetime and efficiency and operating Volt rrn Srry age. An important role is played here by organic emitter Z s Z 2 Z 2 4 Z layers, in particular the matrix materials present therein, and formula (III) organic layers having electron-transporting function. formula (I)-HT--formula (I), 0005. In order to achieve this technical object, there is a continuous search for novel materials which are suitable for use as matrix materials in emitting layers, in particular phos where: phorescent emitting layers. Furthermore, materials having electron-transporting properties for use in electron-transport 0015 Cbz is a carbazole group which is optionally substi ing layers are being sought. tuted by one or more radicals R' and which may be 0006 Phosphorescent emitting layers in the sense of the extended by means of one or more condensed-on indeno present application are organic layers which comprise at least groups to form an indenocarbazole, and in which one or one phosphorescent emitting compound (phosphorescent more aromatic groups =C(R')— or =C(H)— may be dopant). replaced by =N , and which is bonded to the group R' 0007. In accordance with the present application, the term via the carbazole nitrogen atom; phosphorescent emitters encompasses compounds in the case of which the light emission takes place through a spin-forbid 0016 formula (I) is on each occurrence, identically or den transition, for example a transition from an excited triplet differently, any desired unit of the formula (1), where the state or a state having a higher spin quantum number, Such as group T may be bonded to this unit at any desired position; a quintet state. 0017 Z is on each occurrence, identically or differently, 0008. A matrix material in a system comprising a matrix CR' or N: material and a dopant is taken to mean the component whose proportion in the mixture is the greater. Correspondingly, a I0018) R' is on each occurrence, identically or differently, dopant in a system comprising a matrix material and a dopant H, D, F, C(=O)R, CN, Si(R), N(R), P(=O)(R), is taken to mean the component whose proportion in the S(=O)R. S(=O).R., a straight-chain alkyl or alkoxy mixture is the smaller. group having 1 to 20 C atoms or a branched or cyclic alkyl 0009. In accordance with the prior art, carbazole deriva or alkoxy group having 3 to 20 C atoms or an alkenyl or tives, such as, for example, bis(carbazolyl)biphenyl, or car alkynyl group bazole compounds or indenocarbazole compounds, such as, for example, in accordance with WO 2005/039246, US 2005/ 0019 having 2 to 20 C atoms, where the above-mentioned 0069729, JP 2004/288381, EP 1205527 or WO 2008/086851, groups may each be substituted by one or more radicals R are frequently used as matrix materials for phosphorescent and where one or more CH groups in the above-mentioned emitters. groups may be replaced by R°C=CR , —C=C , 0010 Triazine compounds, for example in accordance Si(R), C=O, C-NR, C(=O)C , C(=O)NR , with WO 2010/015306, WO 2007/063754 or WO 2008/ NR, P(=O)(R), -O-, -S. , SO or SO, or an aromatic 056746, are likewise used in this function. or heteroaromatic ring system having 5 to 30 aromatic ring 0011. The prior art furthermore discloses compounds in which a carbazole group or indenocarbazole group is bonded atoms, which may in each case be substituted by one or more to a triazine group, for example in WO 2011/057706, WO radicals R. or an aryloxy or heteroaryloxy group having 5 to 2010/136109 or WO 2011 FOOO455. 30 aromatic ring atoms, which may be substituted by one or 0012 However, there continues to be a need for improve more radicals R, where two or more radicals R' may be ment over the compounds known from the prior art, in par linked to one another and may form a ring; US 2015/0340627 A1 Nov. 26, 2015 (0029 Ar' is an aromatic ring system having 6 to 30 aro formula (A) matic ring atoms, which may be substituted by one or more X radicals R'; h Sx x1's x 0030 T is a single bond or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may salsNx E. El 2 k be substituted by one or more radicals R'. inLI 0031. For the purposes of the present application, the defi nition that the group Cbz is a carbazole group, which may be extended by means of indeno groups to form an indenocar bazole, is taken to mean that indeno groups may be condensed 0021 where the dashed line denotes the bond to the onto one or both of the six-membered rings of the carbazole. remainder of the formula, or R is equal to R', where at If indeno groups are present, one or two are preferably least one group R" performula unit of the formula (I) or present. If two indeno groups are present, they are preferably (II) conforms to the formula (A): not both bonded to the same six-membered ring of the carba 0022. L' is an aromatic or heteroaromatic ring system Zole. having 6 to 30 aromatic ring atoms, which may be substi 0032. An indeno group here is taken to mean the following tuted by one or more radicals R'; Structure: 0023 E is on each occurrence, identically or differently, O, S, or NAr"; 0024 X is on each occurrence, identically or differently, N R1 RI or CR, where at least one group Xper six-membered ring R1 is equal to N: 0025 i is on each occurrence, identically or differently, 0 or 1, where at least one index i per group of the formula : R1 (A) is equal to 1; RI 0026 R is on each occurrence, identically or differently, H, D, F, C(=O)R, CN, Si(R), S(=O)R’, S(=O),R, a straight-chain alkyl group having 1 to 20 C atoms or a 0033 Condensation of the indeno group is taken to mean branched orcyclic alkyl group having 3 to 20 Catoms oran that it shares two ring atoms with two ring atoms of the alkenyl or alkynyl group having 2 to 20 C atoms, where the six-membered ring of the carbazole.
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