Electronic device

Patent metadata

Field	Value
Publication number	US-9831441-B2
Application number	US-201314439098-A
Country	US
Kind code	B2
Filing date	Oct 11, 2013
Priority date	Oct 31, 2012
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

The invention relates to an electronic device containing at least one compound of formula (I) or (II) in an organic layer. The invention further relates to a method for producing the electronic device and the use of a compound of formula (I) or (II) in an electronic device.

First claim

The invention claimed is:

1. An electronic device comprising anode, cathode and at least one organic layer, which comprises at least one compound of the formula (I) or (II)

where a group selected from the groups of the formulae

is bonded at the positions denoted by *, where:
E is selected on each occurrence, identically or differently, from a single bond, C(R 1 ) 2 , Si(R 1 ) 2 , C═O, O, S, S═O, SO 2 and NR 1 ;
Z is on each occurrence, identically or differently, CR 1 or N;
W is selected on each occurrence, identically or differently, from C═O, O, S, S═O, SO 2 and NR 1 ;
Ar 1 is selected on each occurrence, identically or differently, from aryl or heteroaryl groups having 6 to 13 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 ;
Ar 2 is selected on each occurrence, identically or differently, from aryl or heteroaryl groups having 6 to 13 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 ;
X is selected on each occurrence, identically or differently, from C(R 1 ) 2 , Si(R 1 ) 2 , C═O, O, S, S═O, SO 2 and NR 1 ;
Y is a single bond;
R 1 is on each occurrence, identically or differently, H, D, F, C(═O)R 2 , CN, Si(R 2 ) 3 , N(R 2 ) 2 , P(═O)(R 2 ) 2 , S(═O)R 2 , S(═O) 2 R 2 , 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 or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 2 and where one or more CH 2 groups in the above-mentioned groups is optionally replaced by —R 2 C═CR 2 —, —C≡C—, Si(R 2 ) 2 , C═O, C═S, C═NR 2 , —C(═O)O—, —C(═O)NR 2 —, NR 2 , P(═O)(R 2 ), —O—, —S—, SO or SO 2 and where one or more H atoms in the above-mentioned groups is optionally replaced by D, F or CN, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , where two or more radicals R 1 is optionally linked to one another and may form a ring;
R 2 is on each occurrence, identically or differently, H, D, F 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 substituents R 2 here is optionally linked to one another and may form a ring;
n is on each occurrence, identically or differently, 0, 1, 2, 3 or 4;
i is on each occurrence, identically or differently, 0 or 1;
k is on each occurrence, identically or differently, 0 or 1, where at least one index k per group of the formula (C-1) must be equal to 1;
and where a group selected from groups of the formulae (A-1) and (A-2) must be bonded at at least one of the positions denoted by *,
and where furthermore no condensed aryl or heteroaryl group having 14 or more aromatic ring atoms is present in the compound.

2. The electronic device according to claim 1 , wherein the group E is selected on each occurrence, identically or differently, from a single bond, C(R 1 ) 2 , C═O, O, S and NR 1 .

3. The electronic device according to claim 1 , wherein the group Ar 1 is selected on each occurrence, identically or differently, from aryl or heteroaryl groups having 6 to 10 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 .

4. The electronic device according to claim 1 , wherein the group Ar 2 is selected on each occurrence, identically or differently, from aryl or heteroaryl groups having 6 to 10 aromatic ring atoms, which is optionally substituted by one or more radicals R 1 .

5. The electronic device according to claim 1 , wherein R 1 is on each occurrence, identically or differently, H, D, F, CN, Si(R 2 ) 3 , N(R 2 ) 2 , 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, where the above-mentioned groups may each be substituted by one or more radicals R 2 and where one or more CH 2 groups in the above-mentioned 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 aromatic or heteroaromatic ring system having 5 to 20 aromatic ring atoms, which is optionally substituted by one or more radicals R 2 , where two or more radicals R 1 is optionally linked to one another and may form a ring.

6. The electronic device according to claim 1 , wherein the index n is on each occurrence, identically or differently, 0 or 1.

7. The electronic device according to claim 1 , wherein the index i is equal to 0.

8. The electronic device according to claim 1 , wherein in compounds of the formulae (I) and (II), a group selected from groups of the formula (A-1) and (A-2) according to claim 1 is bonded at the positions denoted by *.

9. The electronic device according to claim 1 , wherein the compounds of the formulae (I) and (II) contain no further arylamino groups in addition to the groups (A-1), (A-2), (C-1) and (C-2) according to claim 1 .

10. The electronic device according to claim 1 , wherein the compounds of the formulae (I) and (II) contain no further carbazole groups in addition to the groups (A-1), (A-2), (C-1) and (C-2) according to claim 1 .

11. The electronic device according to claim 1 , wherein the compounds of the formula (I) are compounds of the following formulae (I-1) to (I-4):

where E 1 is selected from C(R 1 ) 2 , Si(R 1 ) 2 , C═O, O, S, S═O, SO 2 and NR 1 ,
where a group selected from the groups of the formulae (A-1), (A-2), (C-1) and (C-2) according to claim 1 is bonded at the positions denoted by *,
and where a group selected from groups of the formulae (A-1) and (A-2) according to claim 1 is bonded at at least one of the positions denoted by *,
and where all other groups are defined as in claim 1 .

12. The electronic device according to claim 1 , wherein the device is an organic integrated circuit (OIC), an organic field-effect transistor (OFET), an organic thin-film transistor (OTFT), an organic light-emitting transistor (OLET), an organic solar cell (OSC), an organic optical detector, an organic photoreceptor, an organic field-quench device (OFQD), an organic light-emitting electrochemical cell (OLEC), an organic laser diode (O-laser) or an organic electroluminescent device (OLED).

13. The electronic device according to claim 12 , wherein the device is an organic electro-luminescent device comprising an organic layer which comprises the compound of the formula (I) or (II) is a layer having a hole-transporting function or an emitting layer.

14. A display and/or as light source in lighting applications and/or as light source in medical or cosmetic applications which comprises the electronic device according to claim 1 .

15. An electronic device in a hole-transporting or in an emitting layer which comprises the compound of the formula (I) or (II)

where a gr

Assignees

• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Martynova Irina
• Montenegro Elvira
• Mujica-Fernaud Teresa
• Voges Frank
• Buesing Arne

Classifications

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title

• C07D333/76

  Dibenzothiophenes · CPC title

• H01L51/0059

  Electricity · mapped topic

• C07C225/22

  having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• C07D311/82

  Xanthenes · CPC title