Electronic devices

Patent metadata

Field	Value
Publication number	US-9871201-B2
Application number	US-201314384437-A
Country	US
Kind code	B2
Filing date	Mar 5, 2013
Priority date	Mar 15, 2012
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

The application relates to an electronic device comprising anode, cathode, at least one emitting layer between anode and cathode, at least one p-doped layer A which comprises a monotriarylamine as host, and at least one layer B comprising a monotriarylamine. The invention furthermore relates to a p-doped mixture comprising a monotriarylamine of the formula (II), (III) or (IV) as host and an electron-acceptor compound as dopant and to the use of the mixture in an electronic device.

First claim

The invention claimed is:

1. An electronic device comprising
anode,
cathode,
at least one emitting layer which is arranged between anode and cathode,
at least one p-doped layer A which comprises a monotriarylamine as host, and
at least one layer B comprising a monotriarylamine and wherein the dopant of layer A is selected from compounds whose LUMO is not more than 0.3 eV higher than the HOMO of the monotriarylamine.

2. The electronic device according to claim 1 , wherein layer A and layer B are arranged between anode and emitting layer.

3. The electronic device according to claim 1 , wherein layer A is arranged on the anode side of layer B.

4. The electronic device according to claim 1 , wherein layer B or another layer which comprises a monotriarylamine is directly adjacent to the emitting layer.

5. The electronic device according to claim 1 , wherein one or more identical monotriarylamines are present in all layers between anode and emitting layer.

6. The electronic device according to claim 1 , wherein the p-doped layer A comprises a dopant which is an electron-acceptor compound.

7. The electronic device according to claim 1 , wherein the dopant of layer A is selected from compounds whose LUMO is not more than 0.1 eV higher than the HOMO of the monotriarylamine.

8. The electronic device according to claim 1 , wherein the dopant of layer A is present in a concentration of 0.1 to 20% by vol.

9. The electronic device according to claim 1 , wherein the monotriarylamine is a compound of the formula (I)

where:
Ar 1 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , CR 2 ═CR 2 R 2 , CN, NO 2 , Si(R 2 ) 3 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups may be replaced by R 2 C═CR 2 , Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 , or a combination of these systems; two or more adjacent substituents R 1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; and
R 2 is on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms may be replaced by D or F; two or more adjacent substituents R 2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another.

10. The electronic device according to claim 1 , selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs).

11. The electronic device according to claim 1 , wherein the dopant of layer A is present in a concentration of 2 to 6% by vol.

12. The electronic device according to claim 11 , wherein at least one of the groups Ar 1 represents an aromatic ring system having 12 to 30 aromatic ring atoms.

13. The electronic device according to claim 11 , wherein at least one of the groups Ar 1 represents biphenyl, terphenyl, quaterphenyl, spirobifluorene, fluorene or indenofluorene, each of which may be substituted by one or more radicals R 1 .

14. A p-doped mixture comprising at least one monotriarylamine of the formula (II), (III) or (IV)

where:
Z is on each occurrence, identically or differently, N or CR 1 , where Z is equal to C if a substituent is bonded;
Ar 2 is an aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
Ar 3 is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
R 1 is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, C(═O)R 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , CR 2 ═CR 2 R 2 , CN, NO 2 , Si(R 2 ) 3 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups may be replaced by R 2 C═CR 2 , C≡C, Si(R 2 ) 2 , Ge(R 2 ) 2 , Sn(R 2 ) 2 , C═O, C═S, C═Se, C═NR 2 , P(═O)(R 2 ), SO, SO 2 , NR 2 , O, S or CONR 2 and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 , or a combination of these systems; two or more adjacent substituents R 1 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another;
R 2 is on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic and/or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms may be replaced by D or F; two or more adjacent substituents R 2 here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; and
n is 0 or 1 and

wherein the dopant of layer A is selected from compounds whose LUMO is not more than 0.3 eV higher than the HOMO of the monotriarylamine.

15. The p-doped mixture according to claim 14 , wherein a dopant which is an electron-acceptor compound is present.

16. The p-doped mixture according to claim 14 , wherein the dopant is present in a concentration of 0.1 to 20% by vol.

17. The p-doped mixture according to claim 14 , wherein the dopant is present in a concentration of 2 to 6% by vol.

18. An electric device comprising the mixture according to claim 14 .

19. An electronic device comprising
anode,
cathode,
at least one emitting layer which is arranged between anode and cathode,
at least one p-doped layer A which comprises a monotriarylamine as host, and
at least one layer B comprising a monotriarylamine
wherein the dopant of layer A is se

Assignees

• Merck Patent Gmbh

Inventors

• Pflumm Christof
• Voges Frank
• Kroeber Jonas V
• Stoessel Philipp
• Kaiser Joachim

Classifications

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09B19/00

  Oxazine dyes · CPC title