US 9,812,648 B2
Spirobifluorene compounds for organic electroluminescent devices
Elvira Montenegro, Weinheim (DE); Amir H. Parham, Frankfurt am Main (DE); Philipp Stoessel, Frankfurt am Main (DE); Teresa Mujica-Fernaud, Darmstadt (DE); Frank Voges, Bad Duerkheim (DE); and Arne Buesing, Frankfurt am Main (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 14/378,529
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Jan. 21, 2013, PCT No. PCT/EP2013/000177
§ 371(c)(1), (2) Date Aug. 13, 2014,
PCT Pub. No. WO2013/120577, PCT Pub. Date Aug. 22, 2013.
Claims priority of provisional application 61/716,810, filed on Oct. 22, 2012.
Claims priority of application No. 12000929 (EP), filed on Feb. 14, 2012.
Prior Publication US 2015/0065730 A1, Mar. 5, 2015
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 279/22 (2006.01); C07D 333/76 (2006.01); C07D 209/88 (2006.01); C07D 307/91 (2006.01); C07D 209/86 (2006.01); C07D 265/38 (2006.01); C07C 211/61 (2006.01); C07C 211/58 (2006.01); H01L 51/00 (2006.01); C09K 11/06 (2006.01); C07C 211/54 (2006.01); H01L 51/50 (2006.01)
CPC H01L 51/0058 (2013.01) [C07C 211/54 (2013.01); C07C 211/58 (2013.01); C07C 211/61 (2013.01); C07D 209/86 (2013.01); C07D 209/88 (2013.01); C07D 265/38 (2013.01); C07D 279/22 (2013.01); C07D 307/91 (2013.01); C07D 333/76 (2013.01); C09K 11/06 (2013.01); H01L 51/006 (2013.01); H01L 51/0061 (2013.01); H01L 51/0072 (2013.01); H01L 51/0073 (2013.01); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1088 (2013.01); C09K 2211/1092 (2013.01); H01L 51/0067 (2013.01); H01L 51/5012 (2013.01); H01L 51/5016 (2013.01); H01L 51/5056 (2013.01); H01L 51/5096 (2013.01); Y02E 10/549 (2013.01)] 10 Claims
 
1. A compound of the formula

OG Complex Work Unit Drawing
where the following applies to the symbols and indices used:
Ar1 is selected from the group consisting of fluorene, biphenyl, terphenyl, quaterphenyl, dibenzofuran and dibenzothiophene, each of which is optionally substituted by one or more radicals R5;
Ar2 is selected from any one of formulae (11) to (27)

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing
where the dashed bond indicates the bond to the nitrogen, and the groups are optionally substituted by one or more radicals R5;
R1, R2, R3, R4 are on each occurrence, identically or differently, selected from the group consisting of H, D, F, Cl, Br, I, CN, Si(R6)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms, and a branched alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, and a cyclic alkyl group having 3 to 40 C atoms, each of which optionally is substituted by one or more radicals R6, where in each case one or more non-adjacent CH2 groups optionally is replaced by Si(R6)2, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6 and where one or more H atoms optionally is replaced by D, F, Cl, Br or I, an aromatic ring system having 6 to 60 C atoms, which may in each case be substituted by one or more radicals R6, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which optionally is substituted by one or more radicals R6, 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 R6, where two or more adjacent substituents R1 or R2 or R3 or R4 may optionally form a mono- or polycyclic, aliphatic ring system, which optionally is substituted by one or more radicals R6;
R5 is on each occurrence, identically or differently, selected from the group consisting of H, D, F, Cl, Br, I, CN, Si(R6)3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched alkyl, alkoxy, and thioalkyl group having 3 to 40 C atoms, and a cyclic alkyl group having 3 to 40 C atoms, each of which optionally is substituted by one or more radicals R6, where in each case one or more non-adjacent CH2 groups optionally is replaced by Si(R6)2, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6 and where one or more H atoms optionally is replaced by D, F, Cl, Br or I, an aromatic ring system having 6 to 60 C atoms, which may in each case be substituted by one or more radicals R6, an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which optionally is substituted by one or more radicals R6, 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 R6;
R6 is selected from H, D, F, an aliphatic hydrocarbon radical having 1 to 20 C atoms, or an aromatic, or heteroaromatic, ring system having 5 to 30 C atoms, in which one or more H atoms optionally is replaced by D or F, where two or more adjacent substituents R6 may form a mono- or polycyclic, aliphatic ring system with one another;
m is 0, 1 or 2;
n is on each occurrence, identically or differently, 0, 1, 2, 3 or 4; and
r, s are on each occurrence, identically or differently, 0, 1, 2, 3 or 4.