Polymers containing structural units which have electron-transport properties

Patent metadata

Field	Value
Publication number	US-9368726-B2
Application number	US-201113813032-A
Country	US
Kind code	B2
Filing date	Jul 8, 2011
Priority date	Aug 2, 2010
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

The present invention relates to a polymer which contains at least one structural unit which has electron-transport properties, to processes for the preparation thereof and to mixtures (blends), solutions and formulations which comprise these poly mers. Furthermore, the present invention relates to the use of these polymers in electronic devices, in particular in organic electro-luminescent devices, so-called OLEDs (OLED=organic light emitting diodes), and to these organic electroluminescent devices themselves. The polymers according to the invention exhibit improved efficiency, in particular on use in OLEDs.

First claim

The invention claimed is:

1. A compound of the following formula (VIII):

where the symbols and indices used have the following meaning:
W and W′ are selected, independently of one another, from the group consisting of halogen, O-tosylate, O-triflate, O—SO 2 R 4 , B(OR 4 ) 2 and Sn(R 4 ) 3 ,
where R 4 is selected on each occurrence, independently of one another, from the group consisting of H, an aliphatic hydrocarbon radical having 1 to 20 C atoms and an aromatic hydro-carbon radical having 6 to 20 ring atoms, and where two or more radicals R 4 may also form an aliphatic ring system with one another; and
X is selected from NR 1 , C(R 1 ) 2 —C(R 1 ) 2 , CR 1 ═CR 1 and

Y 1 and Y 2 are each selected, independently of one another, from C(R 1 ) 2 , NR 1 , C(R 1 ) 2 —C(R 1 ) 2 , CR 1 ═CR 1 and a single bond, but with the proviso that either Y 1 or Y 2 is a single bond,
R 1 is in each case selected, independently of one another, from II, D, F, Cl, Br, I, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)Ar 1 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CR 2 ═CR 2 Ar 1 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally 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 is optionally replaced by F, Cl, Br, I, CN or NO 2 , an aryl, aryloxy, heteroaryl or heteroaryloxy group having 5 to 40 C atoms, which is optionally substituted by one or more non-aromatic radicals R 1 , where, in addition, two or more radicals, R 1 may form an aliphatic or aromatic, mono- or polycyclic ring system with one another, or an electron-transport unit R 3 , but with the proviso that at least one of the radicals R 1 is an electron-transport unit R 3 ,
Ar 1 is selected on each occurrence, in each case independently of one another, from an aryl or heteroaryl group or an aromatic or heteroaromatic ring system,
R 2 is in each case, independently of one another, H, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic hydrocarbon radical having 6 to 20 C atoms, where two or more radicals R 2 may also form a ring system with one another,
R 3 is an electron-transport unit,
n is in each case, independently of one another, 1, 2, 3 or 4, and
m is 1.

2. The compound according to claim 1 , wherein Y 1 and Y 2 are each selected, independently of one another, from NR 1 , C(R 1 ) 2 —C(R 1 ) 2 , CR 1 ═CR 1 and a single bond, but with the proviso that either Y 1 or Y 2 is a single bond.

3. A polymer which contains at least one structural unit of the following formula (I):

where the symbols and indices used have the following meaning:

X is NR 1 , C(R 1 ) 2 —C(R 1 ) 2 , CR 1 ═CR 1 or

Y 1 and Y 2 are each selected, independently of one another, from C(R 1 ) 2 , C(R 1 ) 2 —C(R 1 ) 2 , CR 1 ═CR 1 and a single bond, but with the proviso that either Y 1 or Y 2 is a single bond,
m is 1,
R 1 is in each case selected, independently of one another, from H, D, F, Cl, Br, I, N(Ar 1 ) 2 , C(═O)Ar 1 , P(═O)Ar 1 2 , S(═O)Ar 1 , S(═O) 2 Ar 1 , CR 2 ═CR 2 Ar 1 , CN, NO 2 , Si(R 2 ) 3 , B(OR 2 ) 2 , OSO 2 R 2 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which is optionally substituted by one or more radicals R 2 , where one or more non-adjacent CH 2 groups is optionally 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 is optionally replaced by F, Cl, Br, I, CN or NO 2 , an aryl, aryloxy, heteroaryl or heteroaryloxy group having 5 to 40 C atoms, which is optionally substituted by one or more non-aromatic radicals R 1 , where, in addition, two or more radicals, R 1 may form an aliphatic or aromatic, mono- or polycyclic ring system with one another, or an electron-transport unit R 3 , but with the proviso that at least one of the radicals R 1 is an electron-transport unit R 3 ,
Ar 1 is selected on each occurrence, in each case independently of one another, from an aryl or heteroaryl group or an aromatic or heteroaromatic ring system,
R 2 is in each case, independently of one another, H, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic hydrocarbon radical having 6 to 20 C atoms, where two or more radicals R 2 may also form a ring system with one another,
R 3 is an electron-transport unit, and
where the dashed lines represent the bonds to the adjacent structural units in the polymer.

4. The polymer according to claim 3 , wherein two adjacent radicals, R 1 form an aliphatic or aromatic, mono- or polycyclic ring system with one another, or an electron-transport unit R 3 , but with the proviso that at least one of the radicals R 1 is an electron-transport unit R 3 .

5. The polymer according to claim 3 , wherein R 3 is a unit which is selected from the group consisting of benzimidazole, triazine, pyrimidines, pyrazines, pyridazines, phenanthrolines, ketones, phosphine oxides and derivatives thereof.

6. The polymer according to claim 3 , wherein besides the structural units of the formula (I), it also contains further structural units which are different from those of the formula (I).

7. The polymer according to claim 3 , wherein the proportion of the units of the formula (I) is 0.01 to 100 mol %, based on the total number of recurring units of the polymer.

8. A process for the preparation of the polymer according to claim 3 , wherein the polymer is prepared by Suzuki, Yamamoto, Stille or Hartwig-Buchwald polymerisation.

9. A mixture of one or more polymers according to claim 3 with a further polymeric, oligomeric, dendritic and/or low-molecular-weight substance.

10. A solution or formulation comprising the mixture according to claim 9 in one or more solvents.

11. An organic electroluminescent device which comprises the mixture according to claim 9 .

12. An organic electronic device having one or more active layers, wherein at least one of these active layers comprises the mixture according to claim 9 .

13. The organic electronic device according to claim 12 , wherein the device is an organic or polymeric organic electroluminescent device (OLED, PLED), an organic integrated circuit (O-IC), an organic field-effect transistor (OFET), an organic thin-film transistor (OTFT), an organic solar cell (O-SC), an organic laser diode (O-laser), an organic photovoltaic (OPV) element or device or an organic photoreceptor (OPC).

14. The organic electronic device according to claim 12 , wherein the device is a polymeric organic electroluminescent device (PLED).

15. A solution or formulation comprising one or more polymers according to claim 3 in one or more solvents.

Assignees

• Heun Susanne
• Ludemann Aurélie
• Anémian Rémi Manouk
• Merck Patent Gmbh

Inventors

• Heun Susanne
• Ludemann Aurélie
• Anémian Rémi Manouk

Classifications

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C08G2261/514

  Electron transport · CPC title

• C08G2261/124

  alternating · CPC title

• C08G2261/1412

  Saturated aliphatic units · CPC title

• C08G2261/3142

  fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene · CPC title