Bridged triarylamines and -phosphines as materials for electronic devices

Patent metadata

Field	Value
Publication number	US-9422287-B2
Application number	US-201113640860-A
Country	US
Kind code	B2
Filing date	Mar 16, 2011
Priority date	Apr 14, 2010
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

The present invention relates to a compound according to formula (I), to the use thereof in an electronic device and to an electronic device which comprises one or more compounds according to formula (I).

First claim

The invention claimed is:

1. A compound of formulae (I-1) to (I-4)

wherein
X is N, P, or P═O;
Y is, identically or differently on each occurrence, C(R 1 ) 2 , C═O, C═NR 1 , O, S, SO, SO 2 , PR 1 , POR 1 , NAr, NR 1 , or a single bond;
Z is identically or differently on each occurrence, CR 2 , N, or C if a group Y or T is bonded to Z;
T is, identically or differently on each occurrence, C(R 1 ) 2 , C═O, C═NR 1 , O, S, SO, SO 2 , PR 1 , POR 1 , NAr, NR 1 , or a single bond;
A is Ar 3 , which is an aryl group with 6 to 14 aromatic ring carbons, optionally substituted by one or more radicals R 2 , wherein the bond to a group T starts from the aromatic ring of the group Ar 3 ;
Ar are, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R 2 ;
R 1 and R 2 are, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, NAr 2 , N(R 3 ) 2 , C(═O)R 3 , P(═O)(R 3 ) 2 , S(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, NO 2 , Si(R 3 ) 3 , B(OR 3 ) 2 , OSO 2 R 3 , OH, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 3 , wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , Ge(R 3 ) 2 , Sn(R 3 ) 2 , C═O, C═S, C═Se, C═NR 3 , P(═O)(R 3 ), SO, SO 2 , NR 3 , —O—, —S—, —COO—, or —CONR 3 —, and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN, NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case is optionally substituted by one or more radicals R 3 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or a combination of these systems, wherein two or more radicals R 1 and R 2 optionally define a ring or ring system;
R 3 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, NAr 2 , N(R 4 ) 2 , C(═O)R 4 , P(═O)(R 4 ) 2 , S(═O)R 4 , S(═O) 2 R 4 , CR 4 ═C(R 4 ) 2 , CN, NO 2 , Si(R 4 ) 3 , B(OR 4 ) 2 , OSO 2 R 4 , OH, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, each of which is optionally substituted by one or more radicals R 4 ,
wherein one or more non-adjacent CH 2 groups are optionally replaced by —R 4 C═CR 4 —, —C═C—, Si(R 4 ) 2 , Ge(R 4 ) 2 , Sn(R 4 ) 2 , C═O, C═S, C═Se, C═NR 4 , P(═O)(R 4 ), SO, SO 2 , NR 4 , —O—, —S—, —COO—, or —CONR 4 —, and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 4 , an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, optionally substituted by one or more radicals R 4 , or a combination of these systems, wherein two or more radicals R 3 optionally define a ring or ring system;
R 4 is, identically or differently on each occurrence, H, D, F, or an aliphatic, aromatic and/or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by F, and wherein two or more identical or different substituents R 4 optionally define a ring or ring system;
n is, on each occurrence, independently of one another, 0 or 1, with the proviso that the sum of all values for n is greater than or equal to 1;
m is, on each occurrence, independently of one another, 0 or 1, with the proviso that the sum of all values for m is greater than or equal to 1;
and with the proviso that at least one group Y is a single bond.

2. The compound of claim 1 , wherein X is N.

3. The compound of claim 1 , wherein Y is, identically or differently on each occurrence, C(R 1 ) 2 , S, O, C═O, NR 1 , or a single bond, with the proviso that at least one group Y is a single bond.

4. The compound of claim 1 , wherein the sum of the values of n and m is 2 or 3.

5. The compound of claim 1 , of formula I-1.

6. The compound of claim 1 , wherein said compound is of formulae (I5) to (I-10)

wherein
Z is, identically or differently on each occurrence, CR 2 or N if no group Y or T is bonded to the group Z, or is on each occurrence C if a group Y or T is bonded to the group Z.

7. An oligomer, polymer, or dendrimer comprising one or more compounds of claim 1 , wherein one or more bonds to said oligomer, polymer or dendrimer replace one or more bonds to one or more substituents.

8. A formulation comprising at least one compound of claim 1 and at least one solvent.

9. A process for preparing the compound of claim 1 , comprising
a) synthesizing a precursor molecule unbridged in the relevant position and carrying a group Y* and/or T*; and
b) performing the ring-closure reaction, introducing the bridge Y and/or T.

10. An electronic device comprising the compound of claim 1 .

11. The electronic device of claim 10 , wherein said compound is employed as matrix material in an emitting layer, optionally comprising one or more phosphorescent emitters, and/or is employed as hole-transport material in a hole-transport layer and/or in a hole-injection layer, and/or is employed as emitting material in an emitting layer.

12. A formulation comprising at least one oligomer, polymer, or dendrimer of claim 7 and at least one solvent.

13. An electronic device comprising the oligomer, polymer, or dendrimer of claim 7 .

14. The electronic device of claim 10 , wherein said electronic device is an organic integrated circuit, organic field-effect transistor, organic thin-film transistor, organic light-emitting transistor, organic solar cell, organic optical detector, organic photoreceptor, organic field-quench device, light-emitting electrochemical cell, organic laser diode, or organic electroluminescent device.

15. The electronic device of claim 13 , wherein said electronic device is an organic integrated circuit, organic field-effect transistor, organic thin-film transistor, organic light-emitting transistor, organic solar cell, organic optical detector, organic photoreceptor, organic field-quench device, light-emitting electrochemical cell, organic laser diode, or organic electroluminescent device.

16. The compound of claim 1 of formula I-2.

17. The compound of claim 16 , wherein X is N; Y is, identically or differently on each occurrence, C(R 1 ) 2 , S, O, C═O, NR 1 , or a single bond, with the proviso that at least one group Y is a single bond; and the sum of the values of n and m is 2 or 3.

18. The compound of claim 1 of formula I-3.

19. The compound of claim 18 , wherein X is N; Y is, identically or differently on each occurrence, C(R 1 ) 2 , S, O, C═O, NR 1 , or a single bond, with the proviso that at least one group Y is a single bond; and the sum of the values of n and m is 2 or 3.

20. The compound of claim 1 of formula I-4.

21. The compound of claim 20 , wherein X is N; Y is, identically or differently on each occurr

Assignees

• Parham Amir Hossain
• Pflumm Christof
• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Pflumm Christof

Classifications

• C07D498/06

  Peri-condensed systems · CPC title

• C07D471/06

  Peri-condensed systems · CPC title

• C07D498/16

  Peri-condensed systems · CPC title

• C07D513/22

  in which the condensed system contains four or more hetero rings · CPC title

• H01L51/0072

  Electricity · mapped topic