US 11,737,352 B2
Materials for organic electroluminescent devices
Philipp Stoessel, Frankfurt am Main (DE); Nils Koenen, Griesheim (DE); Christian Ehrenreich, Darmstadt (DE); Philipp Harbach, Muehltal (DE); Lara-Isabel Rodriguez, Darmstadt (DE); Rouven Linge, Darmstadt (DE); Sebastian Meyer, Aschaffenburg (DE); and Aaron Lackner, Mannheim (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 16/479,662
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Jan. 22, 2018, PCT No. PCT/EP2018/051411
§ 371(c)(1), (2) Date Jul. 22, 2019,
PCT Pub. No. WO2018/134392, PCT Pub. Date Jul. 26, 2018.
Claims priority of application No. 17152547 (EP), filed on Jan. 23, 2017.
Prior Publication US 2021/0367155 A1, Nov. 25, 2021
Int. Cl. H10K 85/60 (2023.01); C07F 15/00 (2006.01); C07J 9/00 (2006.01); C07J 43/00 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/626 (2023.02) [C07F 15/0033 (2013.01); C07J 9/00 (2013.01); C07J 43/003 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); H10K 85/622 (2023.02); H10K 85/624 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1025 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1037 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1055 (2013.01); C09K 2211/1074 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 15 Claims
 
1. A compound of one of the formulae (1) to (4),

OG Complex Work Unit Chemistry
where the following applies to the symbols and indices used:
Y is selected from the group consisting of fluorescent emitting groups, phosphorescent emitting groups, host groups for fluorescent emitting compounds and host groups for phosphorescent emitting compounds, having a molecular weight equal or less than 3000 g/mol, and which may in each case be substituted by one or more radicals R1;
Ar is on each occurrence, identically or differently, selected from the group consisting of aromatic ring systems having 6 to 18 aromatic ring atoms, which may in each case also be substituted by one or more radicals R, where two groups Ar are allowed to be connected via a single bond or a divalent bridge;
T is on each occurrence, identically or differently selected from the group consisting of T1 to T19,

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
where the symbol(s) * in T1 to T19 indicates the bonding to the group(s) —(Ar)m—Y in formulae (1) to (4);
R and R1 stand on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, NO2, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl groups having 3 to 40 C atoms, each of which may be substituted by one or more radicals R2, where in each case one or more non-adjacent CH2 groups may be replaced by R2C═CR2, C≡, C═O, C═S, SO, SO2, O or S and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R2, or an aryloxy groups having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R2, where two adjacent substituents R and/or two adjacent substituents R1 may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R2;
R2 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms;
m is on each occurrence, identically or differently, 1, 2, 3 or 4;
n is an integer from 1 to 8; and
p is on each occurrence, identically or differently, 0 or 1, with the proviso that at least one p is equal to 1 in formulae (1) and (2).