Electronic device

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-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 ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ;

R 2 is on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms may be replaced by D or F; and

p is equal to 0 or 1.

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

9. The electronic device according to claim 8 , wherein hole-transport layer A comprises no p-dopant.

10. The electronic device according to claim 1 , wherein hole-transport layer A has a thickness of 100 to 300 nm.

11. The electronic device according to claim 1 , wherein hole-transport layer A comprises no p-dopant.

12. The electronic device according to claim 1 , wherein the p-dopant is selected from quinodimethane compounds, azaindenofluorenediones, azaphenalenes, azatriphenylenes, I 2 , metal halides, metal oxides, transition-metal complexes and transition-metal oxides.

13. The electronic device according to claim 1 , wherein the p-dopant is present in hole-transport layer B in a concentration of 0.1 to 20% by vol.

14. The electronic device according to claim 1 , wherein hole-transport layer C comprises no p-dopant.

15. The electronic device according to claim 1 , wherein hole-transport layer B comprises the same compound as hole-transport material matrix as hole-transport layer C does as hole-transport material.

16. A light source in a lighting application which comprises the electronic device according to claim 1 .

17. A light source for use in a medical application which comprises the electronic device according to claim 1 .

18. A light source in cosmetic application which comprises the electronic device according to claim 1 .

19. The electronic device according to claim 1 , 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.

20. The electronic device according to claim 16 , 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-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 ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 ;

R 2 is on each occurrence, identically or differently, H, D, CN or an aliphatic, aromatic hydrocarbon radical having 1 to 20 C atoms, in which, in addition, H atoms may be replaced by D or F; and

p is equal to 0 or 1.

21. The electronic device according to claim 20 , wherein each one of hole-transport layers A, B, C and A′ comprises at least one compound of one of the formula (II) or (III).

22. The electronic device according to claim 21 , wherein hole-transport layer A comprises no p-dopant.

23. 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

wherein the hole-transport layer A comprises the same compound as hole-transport material as hole-transport layer A′ does as hole-transport material matrix.

24. 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 wherein the hole-transport materials of hole-transport layers A and C are different.