Materials for electronic devices

Patent metadata

Field	Value
Publication number	US-9773979-B2
Application number	US-201214236640-A
Country	US
Kind code	B2
Filing date	Jul 5, 2012
Priority date	Aug 3, 2011
Publication date	Sep 26, 2017
Grant date	Sep 26, 2017

Abstract

The present invention relates to a compound of the formula (I), (II) or (III), to the use of the compound in an electronic device, and to an electronic device comprising a compound of the formula (I), (II) or (III). The present invention furthermore relates to a process for the preparation of a compound of the formula (I), (II) or (III) and to a formulation comprising one or more compounds of the formula (I), (II) or (III).

First claim

The invention claimed is:

1. A compound of formulae (II-A), (II-B) or (III-C) or formula (III)

wherein
A in the compounds of formula (II-B), formula (III-C) formula (III) is C(R 1 ) 2 or

wherein
in the formula (III), the group Ar 1 or the nitrogen atom is bonded to the fluorene ring system in the I position, in the 3-position, or in the 4-position, and in the compounds of formula (II-A), A is

where the dashed lines represent the bonds emanating from the group A;
Z is, identically or differently on each occurrence, CR 1 , or, if a group is bonded in the relevant position, C;
Ar 1 ,Ar 3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 1 ;
Ar 2 is, identically or differently on each occurrence, an arylene group having 6 to 30 aromatic ring atoms or a heteroarylene group having 5 to 14 aromatic ring atoms, optionally substituted by one or more radicals R 1 ;
Ar 4 is on each occurrence, phenyl, optionally substituted by one or more radicals R 1 ;
X is selected from the group consisting of a single bond, C(R 1 ) 2 , C═O, Si(R 1 ) 2 , NR 1 , O, S, S═O, and S(═O) 2 ;
R 1 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR 2 ) 2 , CHO, C(═O)R 2 , CR 2 ═C(R 2 ) 2 , CN, C(═O)OR 2 , C(═O)N(R 2 ) 2 , Si(R 2 ) 3 , N(R 2 ) 2 , NO 2 , P(═O)(R 2 ) 2 , OSO 2 R 2 , OR 2 , S(═O)R 2 , S(═O) 2 R 2 , a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms, a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, or an alkenyl or tilkynyl group having 2 to 20 C atoms, wherein the above-mentioned groups are optionally substituted by one or more radicals R 2 , and wherein one or more CH 2 groups in the above-mentioned groups are 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 wherein one or more H atoms in the above-mentioned groups are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 2 ;
R 2 is, identically or differently on each occurrence, H, D, F, Cl, Br, I, B(OR 3 ) 2 , CHO, C(═O)R 3 , CR 3 ═C(R 3 ) 2 , CN, C(═O)OR 3 , C(═O)N(R 3 ) 2 , Si(R 3 ) 3 , N(R 3 ) 2 , NO 2 , P(═O)(R 3 ) 2 , OSO 2 R 3 , OR 3 , S(═O)R 3 , S(═O) 2 R 3 , a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 C atoms, a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms, wherein the above-mentioned groups are optionally substituted by one or more radicals R 3 , and wherein one or more CH 2 groups in the above-mentioned groups are optionally replaced by -R 3 C═CR 3 —, —C≡C—, Si(R 3 ) 2 , C═O, C═S, C═NR 3 , —C(═O)O—, —C(═O)NR 3 —, NR 3 , P(═O)(R 3 ), —O—, —S—, SO, or SO 2 , and wherein one or more H atoms in the above-mentioned groups are optionally replaced by D, F, Cl, Br, I, CN, or NO 2 , an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 3 , or an aryloxy or heteroaryloxy group having 5 to 30 aromatic ring atoms, optionally substituted by one or more radicals R 3 , wherein two or more radicals R 2 optionally define a ring system;
R 3 is, identically or differently on each occurrence, H, D, F, or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, wherein one or more H atoms are optionally replaced by D or F; wherein two or more substituents R 3 optionally define a ring system;
m is 0, 1, 2, or 3, wherein when m═0, the group is not present;
n is 0, 1, 2, or 3, wherein when n═0, the group is not present;
wherein n in formulae (II-A), (II-B) or (II-C) must be 1 if the group X represents a single bond; and with the proviso that the compound does not contain a heteroaryl group which contains more than 14 aromatic ring atoms.

2. The compound of claim 1 , wherein the group Ar 1 or, in the case where m═0, the group N(Ar 3 ), is bonded to the fluorenyl ring system in the 3-position.

3. The compound of claim 1 , wherein A is C(R 1 ) 2 .

4. The compound of claim 1 , wherein Ar 1 represents an aromatic ring system having 6 to 12 aromatic ring atoms, optionally substituted by one or more radicals R 1 .

5. The compound of claim 1 , wherein Ar 2 represents a phenylene group, optionally substituted by one or more radicals R 1 .

6. The compound of claim 1 , wherein the group X is selected from the group consisting of a single bond, C(R 1 ) 2 , O, and S.

7. The compound of claim 1 , wherein m is zero.

8. The compound of claim 1 , wherein n is 1 or 2.

9. The compound of claim 1 , with the proviso that no condensed aryl group having more than 14 aromatic ring atoms is present in the compound.

10. The compound of claim 1 , wherein the compound cannot be represented by a mirror-symmetrical structural formula.

11. An oligomer, polymer, or dendrimer, containing one or more compounds of claim 1 , wherein the bonds to the oligomer, polymer, or dendrimer, are optionally localised at any desired positions in formula (II), or formula (III), that are substituted by R 1 .

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

13. A formulation comprising at least one polymer, oligomer, or dendrimer of claim 11 and at least one solvent.

14. An electronic device comprising at least one compound of claim 1 .

15. An electronic device comprising at least one polymer, oligomer, or dendrimer, of claim 11 .

16. The electronic device of claim 14 , wherein said electronic device is selected from the group consisting of 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, and organic electroluminescent device.

17. The electronic device of claim 15 , wherein said electronic device is selected from the group consisting of 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, and organic electroluminescent device.

18. The electronic device of claim 14 , wherein the electronic device is an organic electroluminescent device, and wherein the compound is employed in one or more of the following functions:
as hole-transport material in a hole-transport or hole-injection layer,
as matrix material in an emitting layer,
as electron-blocking material,
as exciton-blocking material,
as material for an interlayer.

19. The electronic device of claim 15 wherein the electronic device is an organic electrolutninescent device, and wherein the polymer, oligomer, or dendrime

Assignees

• Parham Amir Hossain
• Buesing Arne
• Pflumm Christof
• Mujica-Fernaud Teresa
• Stoessel Philipp
• Eberle Thomas
• Voges Frank
• Merck Patent Gmbh

Inventors

• Parham Amir Hossain
• Buesing Arne
• Pflumm Christof
• Mujica-Fernaud Teresa
• Stoessel Philipp
• Eberle Thomas
• Voges Frank

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C07C255/58

  containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton · CPC title

• C07C211/54

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title