Hyperbranched polymers, process for the preparation thereof and use thereof in electronic devices

Patent metadata

Field	Value
Publication number	US-9825228-B2
Application number	US-201214354388-A
Country	US
Kind code	B2
Filing date	Oct 1, 2012
Priority date	Oct 28, 2011
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

The present invention relates to hyperbranched polymers, to a process for the preparation thereof, and to the starting compounds necessary for the preparation. The present invention furthermore relates to the use of the hyperbranched polymers according to the invention in electronic devices and to the electronic devices themselves.

First claim

The invention claimed is:

1. A hyperbranched polymer comprising at least one unit of formula (I)

wherein
A 1 is a functional structural element;
m is an integer≧3; and

the lines are connections to further units of the polymer; and at least one unit of formula (II)

wherein
A 2 is a functional structural element;
l is an integer≧1; and

the line is a connection to another unit of the polymer,
wherein at least one unit of formula (II) is selected from a solubility-promoting unit of formula (IIId2):

wherein
R 1 is, in each case, independently of one another, hydrogen, a straight-chain alkyl, alkenyl, alkoxy, or thioalkoxy group having 1 or 2 to 40 C atoms respectively or a branched or cyclic alkyl, alkenyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, or is a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxycarbonyl group having 2 to 40 C atoms, an aryloxycarbonyl group having 7 to 40 C atoms, a formyl group (—C(═O)—H), an isocyano group, a CF 3 group, Cl, Br, F, and a crosslinkable group; and
s is 0, 1, 2, 3, or 4;
t is 0, 1, 2, or 3; and
u and v
are each, independently of one another, 0, 1, 2, 3, 4, or 5;

wherein the dashed bond indicates the bond to a further unit of the hyperbranched polymer.

2. The hyperbranched polymer of claim 1 , wherein the functional structural element A l is a structural element which has hole-injection and/or hole-transport properties and is selected from the group consisting of triarylamine derivatives, benzidine derivatives, tetraaryl-para-phenylenediamine derivatives, triaryl-phosphine derivatives, phenothiazine derivatives, phenoxazine derivatives, dihydrophenazine derivatives, thianthrene derivatives, dibenzo-para-dioxin derivatives, phenoxathyine derivatives, carbazole derivatives, azulene derivatives, pyrrole derivatives, furan derivatives, and O—, S—, or N-containing heterocycles having a high HOMO.

3. The hyperbranched polymer of claim 1 , wherein the functional structural element A 1 is a structural element which has electron-injection and/or electron-transport properties and is selected from the group consisting of pyridine derivatives, pyrimidine derivatives, pyridazine derivatives, pyrazine derivatives, oxadiazole derivatives, quinolone derivatives, quinoxaline derivatives, anthracene derivatives, benzanthracene derivatives, pyrene derivatives, perylene derivatives, benz-imidazole derivatives, triazine derivatives, triphenylene derivatives, ketone derivatives, phosphine oxide derivatives, phenazine derivatives, triarylboranes, and O—, S—, or N-containing heterocycles having a low LUMO.

4. The hyperbranched polymer of claim 1 , wherein the functional structural element A 1 is a structural element which emits light and is selected from the group consisting of fluorescent emitters and phosphorescent emitters.

5. The hyperbranched polymer of claim 1 , wherein the functional structural element A 1 is a structural element which is a host material and is an oligoarylene.

6. The hyperbranched polymer of claim 1 , wherein the functional structural element A 1 or A 2 is a solubility-promoting unit of formula (IIId2):

wherein
R 1 is, in each case, independently of one another, hydrogen, a straight-chain alkyl, alkenyl, alkoxy, or thioalkoxy group having 1 or 2 to 40 C atoms respectively or a branched or cyclic alkyl, alkenyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, or is a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxycarbonyl group having 2 to 40 C atoms, an aryloxycarbonyl group having 7 to 40 C atoms, a formyl group (—C(═O)—H), an isocyano group, a CF 3 group, Cl, Br, F, and a crosslinkable group; and
s is 0, 1, 2, 3, or 4;
t is 0, 1, 2, or 3; and
u and v
are each, independently of one another, 0, 1, 2, 3, 4, or 5;

wherein the dashed bond indicates the bond to a further unit of the hyperbranched polymer.

7. The hyperbranched polymer of claim 1 , wherein the units of formula (I) are selected from the group consisting of:
units which have hole-injection and/or hole-transport properties and are selected from the group consisting of triarylamine derivatives, benzidine derivatives, tetraaryl-para-phenylenediamine derivatives, triarylphosphine derivatives, phenothiazine derivatives, phenoxazine derivatives, dihydrophenazine derivatives, thianthrene derivatives, dibenzo-para-dioxin derivatives, phenoxathyine derivatives, carbazole derivatives, azulene derivatives, pyrrole derivatives, furan derivatives, and O—, S—, or N-containing heterocycles having a high HOMO;
units which have electron-injection and/or electron-transport properties and are selected from the group consisting of pyridine derivatives, pyrimidine derivatives, pyridazine derivatives, pyrazine derivatives, oxadiazole derivatives, quinolone derivatives, quinoxaline derivatives, anthracene derivatives, benzanthracene derivatives, pyrene derivatives, perylene derivatives, benzimidazole derivatives, triazine derivatives, triphenylene derivatives, ketone derivatives, phosphine oxide derivatives, phenazine derivatives, triarylboranes, and O—, S—, or N-containing heterocycles having a low LUMO; and
units which have light-emitting properties and are selected from the groups consisting of fluorescent emitters and phosphorescent emitters; and
the units of formula (II) are selected from solubility-promoting structural units of formula -(IIId2):

wherein
R 1 is in each case, independently of one another, hydrogen, a straight-chain alkyl, alkenyl, alkoxy, or thioalkoxy group having 1 or 2 to 40 C atoms respectively or a branched or cyclic alkyl, alkenyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, or is a silyl group or a substituted keto group having 1 to 40 C atoms, an alkoxycarbonyl group having 2 to 40 C atoms, an aryloxycarbonyl group having 7 to 40 C atoms, a formyl group (—C(═O)—H), an isocyano group, a CF 3 group, Cl, Br, F, and a crosslinkable group; and
s is 0, 1, 2, 3, or 4;
t is 0, 1, 2, or 3; and
u and v
are each, independently of one another, 0, 1, 2, 3, 4, or 5;

wherein the dashed bond indicates the bond to a further unit of the hyperbranched polymer.

8. A polymer mixture comprising one or more hyperbranched polymers of claim 1 and one or more further polymeric, oligomeric, dendritic, or low-molecular-weight substances.

9. A formulation comprising one or more hyperbranched polymers of claims 1 in one or more solvents.

10. A formulation comprising a polymer mixture of claim 8 in one or more solvents.

11. An electronic or opto-electronic device comprising one or more active layers, wherein at least one of said one or more active layers comprises one or more hyperbranched polymers of claim 1 .

12. The electronic or opto-electronic device of claim 11 , wherein said electronic or opto-electronic device is selected from the group consisting of organic electroluminescent devices, polymeric organic electroluminescent devices, organic field-effect transistors, organic integrated circuits, organic thin-film transistors, organic solar cells, organic laser diodes, organic photovoltaic elements

Assignees

• Merck Patent Gmbh

Inventors

• Schulte Niels
• Reis Eva Maria

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• H01L51/0095

  Electricity · mapped topic

• H01L51/0056

  Electricity · mapped topic

• H01L51/0043

  Electricity · mapped topic