US 9,812,643 B2
Materials for electronic devices
Arne Buesing, Frankfurt am Main (DE); Holger Heil, Frankfurt am Main (DE); Philipp Stoessel, Frankfurt am Main (DE); Frank Voges, Bad Duerkheim (DE); Constanze Brocke, Gross-Gerau (DE); Yoonhyun Kwak, Yongin (KR); Hyein Jeong, Yongin (KR); Samil Khol, Yongin (KR); and Sunyoung Lee, Yongin (KR)
Assigned to Merck Patent GmbH, Darmstadt (DE); and Samsung Display Co., Ltd., Yongin, Gyeonggi-Do (KR)
Appl. No. 14/354,153
Filed by Merck Patent GmbH, Darmstadt (DE); and Samsung Display Co., Ltd., Yongin, Gyeonggi-Do (KR)
PCT Filed Oct. 9, 2012, PCT No. PCT/EP2012/004225
§ 371(c)(1), (2) Date Apr. 25, 2014,
PCT Pub. No. WO2013/060418, PCT Pub. Date May 2, 2013.
Claims priority of application No. 11008620 (EP), filed on Oct. 27, 2011.
Prior Publication US 2014/0291586 A1, Oct. 2, 2014
Int. Cl. H01L 51/50 (2006.01); H01L 51/00 (2006.01); C09K 11/06 (2006.01); H05B 33/22 (2006.01); C07D 487/14 (2006.01); C07D 251/24 (2006.01); C07D 209/86 (2006.01)
CPC H01L 51/0039 (2013.01) [C07D 209/86 (2013.01); C07D 251/24 (2013.01); C07D 487/14 (2013.01); C09K 11/06 (2013.01); H01L 51/0036 (2013.01); H01L 51/0059 (2013.01); H01L 51/0072 (2013.01); H05B 33/22 (2013.01); C09K 2211/1029 (2013.01); H01L 51/5056 (2013.01); H01L 51/5096 (2013.01); Y02E 10/549 (2013.01)] 24 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Drawing
wherein:
Ar1 is

OG Complex Work Unit Drawing
which is substituted by at least one radical RA at a position ortho to the nitrogen, and which Ar1-1 is optionally further substituted by one or more radicals RA or R1, and
 X is, identically or differently on each occurrence, CRA or CR1, wherein at least one group X per formula must be CRA, wherein the dashed line on the left denotes the bond from the group Ar1 to the carbazole group and the dashed line on the right denotes the bond from the group Ar1 to the nitrogen atom;
Ar2 is an aromatic in system having 6 to 12 aromatic ring atoms, optionally substituted by one or more radicals R1;
RA is, identically or differently on each occurrence, a straight-chain alkyl group having 1 to 8 C atoms, or a branched alkyl group having 3 to 8 C atoms, each of which is optionally substituted by one or more radicals R3;
R1 is, identically or differently on each occurrence, H, D, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R3, or an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, optionally substituted by one or more radicals R3;
R3 is, identically or differently on each occurrence, H, D, F or an aliphatic, aromatic and/or heteroaromatic organic radical haying 1 to 20 C atoms, in which, in addition, one or more H atoms are optionally replaced by D or F; two or more substituents R3 optionally define an aliphatic or aromatic ring;
and where a group R1 is optionally bonded to any of the free positions of the aromatic rings in formula (I).