US 11,999,819 B2
Formulation containing a highly branched polymer, highly branched polymer and electro-optical device containing this highly branched polymer
Beate Burkhart, Darmstadt (DE); Miriam Engel, Darmstadt (DE); Matthias Hengst, Aschaffenburg (DE); Holger Heil, Frankfurt am Main (DE); Manuel Hamburger, Mannheim (DE); Christoph Leonhard, Otzberg (DE); and Gaelle Bealle, Heidelberg (DE)
Assigned to Merck Patent GmbH, Darmstadt (DE)
Appl. No. 17/260,202
Filed by Merck Patent GmbH, Darmstadt (DE)
PCT Filed Jul. 8, 2019, PCT No. PCT/EP2019/068227
§ 371(c)(1), (2) Date Jan. 13, 2021,
PCT Pub. No. WO2020/011701, PCT Pub. Date Jan. 16, 2020.
Claims priority of application No. 18182941 (EP), filed on Jul. 11, 2018.
Prior Publication US 2021/0277176 A1, Sep. 9, 2021
Int. Cl. C08G 61/12 (2006.01); C08G 73/02 (2006.01); C09D 165/00 (2006.01); H10K 50/15 (2023.01); H10K 71/00 (2023.01); H10K 71/15 (2023.01); H10K 85/10 (2023.01)
CPC C08G 61/12 (2013.01) [C08G 73/026 (2013.01); C09D 165/00 (2013.01); H10K 85/111 (2023.02); H10K 85/115 (2023.02); H10K 85/151 (2023.02); C08G 2261/135 (2013.01); C08G 2261/1412 (2013.01); C08G 2261/148 (2013.01); C08G 2261/312 (2013.01); C08G 2261/3142 (2013.01); C08G 2261/3162 (2013.01); C08G 2261/411 (2013.01); C08G 2261/512 (2013.01); C08G 2261/76 (2013.01); C08G 2261/95 (2013.01); H10K 50/15 (2023.02); H10K 71/00 (2023.02); H10K 71/15 (2023.02)] 12 Claims
OG exemplary drawing
 
1. A formulation comprising
A) at least one highly branched polymer which contains
30 to 70 mol % of at least one hole-transporting recurring unit A selected from triarylamine units of the following formula (A)

OG Complex Work Unit Chemistry
where
Ar1 to Ar3 are on each occurrence, in each case identically or differently, a mono- or polycyclic, aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R1)2, CN, NO2, Si(R1)3, B(OR1)2, C(═O)R1, P(═O)(R1)2, S(═O)R1, S(═O)2R1, OSO2R1, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, which may in each case be substituted by one or more radicals R1, where one or more non-adjacent CH2 groups may be replaced by R1C═CR1, C═C, Si(R1)2, C═O, C═S, C═NR1, P(═O)(R1), SO, SO2, NR1, O, S, or CONR1 and where one or more H atoms may be replaced by D, F, Cl, Br, I or CN, or a mono- or polycyclic, aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R1, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R1, or an aralkyl or heteroarylaralkyl group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R1, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R1, or a crosslinkable group Q, where two or more radicals R may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
R1 is on each occurrence, identically or differently, H, D, F or an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic and/or heteroaromatic hydrocarbon radical having 5 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; where two or more substituents R1 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; and the dashed lines represent bonds to adjacent structural units in the polymer,
wherein Ar3 is substituted by Ar4 in at least one, of the two ortho positions, where Ar4 is a mono- or polycyclic, aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R,
5 to 30 mol % of at least one branching recurring unit B,
5 to 30 mol % of at least one further recurring unit C selected from 4,5-dihydropyrene derivatives, 4,5,9,10-tetrahydropyrene derivatives, fluorene derivatives, 9,9′-spirobifluorene derivatives, phenanthrene derivatives, 9,10-dihydrophenanthrene derivatives, 5,7-dihydrodibenzoxepine derivatives and cis- and trans-indenofluorene derivatives, 1,2-: 1,3- or 1,4-phenylene, 1,2-, 1,3- or 1,4-naphthylene, 2,2′-, 3,3′- or 4,4′-biphenylylene, 2,2″-, 3,3″-, or 4,4″-terphenylylene, 2,2′-, 3,3′- or 4,4′-bi-1, 1′-naphthylylene or 2,2′″-, 3,3′″-, or 4,4″′-quaterphenylylene derivatives, and
5 to 40 mol % of at least one end group E,
where the recurring units A, B and C are different from one another, wherein the highly branched polymer has a molecular weight Mw in the range from 25,000 to 500,000 g/mol, and
B) at least one organic solvent having a boiling point of at least 200° C.,
wherein the formulation has a viscosity of from 2 to 20 mPas.