Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-9517977-B2
Application number	US-201013504553-A
Country	US
Kind code	B2
Filing date	Oct 1, 2010
Priority date	Oct 29, 2009
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

The present invention relates to compounds of the formula (I), to mixtures of the said compounds with emitter compounds, to the use of compounds of the formula (I) and the said mixtures in electronic devices, and to electronic devices containing one or more compounds of the formula (I) and/or mixtures of compounds of the formula (I) with emitter compounds.

First claim

The invention claimed is:

1. A compound of the general formula (I)
Z—(Y) n   formula (I),

where
Z is selected from terphenyl, triphenylene, benzocarbazole, benzonaphthofuran, benzophenanthrene, fluoranthene, benzanthracene, spirobidibenzosilole, spirobifluorene, indenofluorene, benzindenofluorene, indolocarbazole, indenocarbazole, quinacridones, which is optionally linear or angular, dibenzoquinoxaline, dibenzocinnoline, dibenzophthalazine, dibenzoquinazoline and benzacridine, where the said groups may optionally be substituted by one or more radicals R;
Y, identically or differently on each occurrence, represents a phenyl, tolyl, biphenyl, terphenyl, diphenyltriazinyl, pyridinyl, each of which carries two or more deuterium atoms and no further substituents apart from deuterium and hydrogen;
n can adopt a value from 1 to 15;
R is identically or differently on each occurrence, represent H, D, F, Cl, Br, I, CN, Si(R 2 ) 3 , NO 2 or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more adjacent or non-adjacent CH 2 groups is optionally replaced by —C≡C—, —R 2 C═CR 2 —, Si(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S, C(═O)O or C(═O)NR 2 , or an aromatic or heteroaromatic ring system having 5 to 60 ring atoms, which may in each case be substituted by one or more radicals R 2 ; two or more substituents R on the group Z and/or on one or more of the groups Y is optionally linked to one another and optionally form a mono- or polycyclic aliphatic, aromatic or heteroaromatic ring system, wherein the group R does not represent a deuterium atom; and
R 2 on each occurrence, identically or differently, represents H, D or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more adjacent or non-adjacent radicals R 2 here is optionally linked to one another and optionally form a mono- or polycyclic aliphatic, aromatic or heteroaromatic ring system.

2. The compound according to claim 1 , wherein for each of the groups Y, Y is fully substituted by deuterium.

3. The compound according to claim 1 , wherein the compound conforms to one of the following formulae:

where the groups Z and the index n are as defined in claim 1 .

4. The compound according to claim 1 , wherein the radical R is selected on each occurrence, identically or differently, from H, F, CN, Si(R 2 ) 3 or a straight-chain alkyl or alkoxy group having 1 to 20 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more adjacent or non-adjacent CH 2 groups is optionally replaced by —C≡C—, —R 2 C═CR 2 —, Si(R 2 ) 2 , C═O, C═NR 2 , NR 2 , O, S, C(═O)O or C(═O)NR 2 , or an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 .

5. A process for the preparation of the compound according to claim 1 , which comprises linking one or more groups Y to the group Z via an organometallic coupling reaction.

6. A mixture comprising one or more compounds of the formula (I) according to claim 1 and at least one emitter compound.

7. The mixture according to claim 6 , wherein at least one fluorescent emitter compound is present, which preferably represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more substituents R 3 , where
R 3 , identically or differently on each occurrence, represents H, D, F, Cl, Br, I, CN, N(R 4 ) 2 , N(Ar) 2 , NO 2 , Si(R 4 ) 3 or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 4 , where one or more adjacent or non-adjacent CH 2 groups is optionally replaced by —C≡C—, —R 4 C═CR 4 —, Si(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , O, S, C(═O)O or C(═O)NR 4 ; two or more substituents R 3 here is optionally linked to one another and optionally form a mono- or polycyclic aliphatic, aromatic or heteroaromatic ring system, and in addition
Ar on each occurrence, identically or differently, represents an aryl group having 6 to 60 C atoms, which may optionally be substituted by one or more substituents R 4 , and
R 4 on each occurrence, identically or differently, is H, D or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms is optionally replaced by D or F; two or more adjacent or non-adjacent radicals R 4 here is optionally linked to one another and optionally form a mono- or polycyclic aliphatic, aromatic or heteroaromatic ring system.

8. The mixture according to claim 6 , wherein at least one phosphorescent emitter compound is present.

9. The mixture according to claim 6 , wherein at least one phosphorescent emitter compound is present, and is selected from organometallic complexes having at least one metal-carbon bond which contain a metal selected from the group consisting of chromium, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, nickel, palladium, platinum, copper, silver and gold.

10. A formulation comprising at least one compound according to claim 1 and at least one solvent.

11. A formulation comprising at least one mixture according to claim 6 and at least one solvent.

12. An electronic device comprising at least one compound according to claim 1 .

13. An electronic device comprising at least one mixture according to claim 6 .

14. The electronic device according to claim 12 , wherein the device is an organic electroluminescent device (OLED), an organic field-effect transistor (O-FET), an organic thin-film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic integrated circuit (O-IC), an organic solar cell (O-SC), an organic field-quench device (O-FQD), a light-emitting electrochemical cell (LEC), an organic laser diode (O-laser) or an organic photoreceptor.

15. An electronic device comprising one or more compounds according to claim 1 as a host material in an emitting layer together with one or more emitter compounds.

16. A compound of the general formula (I)
Z—(Y) n

where
Z is terphenyl, triphenylene, spirobifluorene, benzophenanthrene, fluoranthene, benzanthracene, or a heteroaryl group having 15 to 40 aromatic ring atoms, which is optionally substituted by one or more radicals R,
Y, identically or differently on each occurrence, represents a phenyl, tolyl, biphenyl, terphenyl, diphenyltriazinyl, pyridinyl, each of which carries two or more deuterium atoms and no further substituents apart from deuterium and hydrogen;
n can adopt a value from 1 to 15;
R is identically or differently on each occurrence, represent H, D, F, Cl, Br, I, CN, Si(R 2 ) 3 , NO 2 or a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thi

Assignees

• Spreitzer Hubert
• Schwaiger Jochen
• Becker Heinrich
• Merck Patent Gmbh

Inventors

• Spreitzer Hubert
• Schwaiger Jochen
• Becker Heinrich

Classifications

• H01L51/0067

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic

• C07B59/00 Primary

  Introduction of isotopes of elements into organic compounds {; Labelled organic compounds per se} · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title