Electronic device

Patent metadata

Field	Value
Publication number	US-9917272-B2
Application number	US-201314434277-A
Country	US
Kind code	B2
Filing date	Sep 11, 2013
Priority date	Oct 9, 2012
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

Abstract

The present application relates to an electronic device comprising a hole-transport layer A, a doped hole-transport layer B and a hole-transport layer C, where hole-transport layers A, B and C are arranged between the anode and the emitting layer, and where hole-transport layer B is arranged on the cathode side of hole-transport layer A and hole-transport layer C is arranged on the cathode side of hole-transport layer B.

First claim

The invention claimed is:

1. An electronic device comprising anode, cathode and at least one emitting layer arranged between the anode and the cathode, and
at least one hole-transport layer A, comprising at least one hole-transport material which is selected from triarylamine compounds,
at least one p-doped hole-transport layer B, comprising at least one p-dopant and at least one hole-transport material matrix which is selected from triarylamine compounds,
at least one hole-transport layer C, comprising at least one hole-transport material, which is selected from triarylamine compounds,

where hole-transport layers A, B and C are arranged between the anode and the emitting layer, and
where hole-transport layer B is arranged on the cathode side of hole-transport layer A, and hole-transport layer C is arranged on the cathode side of hole-transport layer B and wherein hole-transport layers A, B and C and are directly adjacent to one another and the hole-transport layers A, B and C each comprise one or more identical or different monotriarylamine compounds.

2. The electronic device according to claim 1 , wherein the device is selected from organic light-emitting transistors (OLETs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) or organic electroluminescent devices (OLEDs).

3. The electronic device according to claim 1 , wherein the anode comprises tungsten oxide, molybdenum oxide and/or vanadium oxide, and/or in that a p-doped hole-transport layer A′, comprising at least one p-dopant and a hole-transport material matrix, is arranged between the anode and hole-transport layer A.

4. The electronic device according to claim 3 , wherein hole-transport layers A, B, C and A′ each comprise one or more identical or different monotriarylamine compounds.

5. The electronic device according to claim 3 , wherein at least one of hole-transport layers A, B, C and A′ comprises at least one compound of one of the formulae (I) to (VI)

where:
Z is on each occurrence, identically or differently, N or CR 1 , where Z is equal to C if a substituent is bonded;
X, Y are on each occurrence, identically or differently, a single bond, O, S, Se, BR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , C(R 1 ) 2 —C(R 1 ) 2 or CR 1 ═CR 1 ;
E is O, S, Se, BR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , C(R 1 ) 2 —C(R 1 ) 2 or CR 1 ═CR 1 ;
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 ; and
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 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;
i is on each occurrence, identically or differently, 0 or 1, where the sum of all i is at least equal to 1;
p is equal to 0 or 1;
m, n are, identically or differently, 0 or 1, where the sum of m and n is equal to 1 or 2.

6. The electronic device according to claim 3 , wherein each one of hole-transport layers A, B, C and A′ comprises at least one compound of one of the formulae (I) to (VI)

where:
Z is on each occurrence, identically or differently, N or CR 1 , where Z is equal to C if a substituent is bonded;
X, Y are on each occurrence, identically or differently, a single bond, O, S, Se, BR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , C(R 1 ) 2 -C(R 1 ) 2 or CR 1 ═CR 1 ;
E is O, S, Se, BR 1 , C(R 1 ) 2 , Si(R 1 ) 2 , NR 1 , PR 1 , C(R 1 ) 2 -C(R 1 ) 2 or CR 1 ═CR 1 ;
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 ; and
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 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;
i is on each occurrence, identically or differently, 0 or 1, where the sum of all i is at least equal to 1;
p is equal to 0 or 1;
m, n are, identically or differently, 0 or 1, where the sum of m and n is equal to 1 or 2.

7. The electronic device according to claim 3 , wherein at least one of hole-transport layers A, B, C and A′ comprises at least one compound of one of the formula (II) or (III)

where:
Z is on each occurrence, identically or differently, N or CR 1 , where Z is equal to C if a substituent is bonded;
X is a single bond;
Ar 1 is on each occurrence, identically or differently, an aromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 ; and
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-ch

Assignees

• Merck Patent Gmbh

Inventors

• Voges Frank
• Kroeber Jonas Valentin
• Pflumm Christof
• Kaiser Joachim
• Buesing Arne

Classifications

• A61N5/06

  using light · CPC title

• A61N2005/0653

  Organic light emitting diodes · CPC title

• H01L51/0059

  Electricity · mapped topic

• H01L51/0073

  Electricity · mapped topic

• H01L51/0094

  Electricity · mapped topic