Polymers containing substituted oligo-triarylamine units and electroluminescence devices containing such polymers

Patent metadata

Field	Value
Publication number	US-9745420-B2
Application number	US-201314394288-A
Country	US
Kind code	B2
Filing date	Apr 15, 2013
Priority date	Apr 17, 2012
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

The present invention relates to polymers containing oligo-triarylamine repetition units that are substituted in the ortho position, a method for the production thereof, and use thereof in electronic devices, particularly in organic electroluminescence devices, known as OLEDs (OLED=organic light emitting diodes). The present invention further relates to organic electroluminescence devices containing these polymers.

First claim

The invention claimed is:

1. A polymer comprising at least one structural unit of the following formula (I):

wherein the at least one structural unit of the formula (I) is selected from the structural units of the following formulae (I-1a), (I-1b), (I-1c) and (I-1d):

where
Ar 1 to Ar 5 is on each occurrence, in each case identically or differently, a mono- or polycyclic, aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 1 ) 2 , CN, NO 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , C(═O)R 1 , P(═O)(R 1 ) 2 , S(═O)R 1 , S(═O) 2 R 1 , OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R′, where one or more non-adjacent CH 2 groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, C═S, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , O, S or CONR 1 and where one or more H atoms may be replaced by D, F, Cl, Br, I or CN, or a mono- or polycyclic, 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 1 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or a crosslinkable group Q, where two or more radicals R may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
R 1 is on each occurrence, identically or differently, H, D, F or an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic and/or a heteroaromatic hydrocarbon radical having 5 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; where two or more substituents R 1 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; and
n=0, 1, 2 or 3,
m=0, 1, 2, 3 or 4,
X═CR 2 , NR, SiR 2 , O, S, C═O or P═O, and p and q are each 0 or 1, where the sum (p+q)=1 or 2,
where the dashed lines represent bonds to adjacent structural units in the polymer.

2. The polymer according to claim 1 , wherein the at least one structural unit of the formulae (I-1a), (I-1b), (I-1c) and (I-1d) is selected from structural units of the following formulae (II), (III), (IV), (V), (VI), (VII), (VIII) and (IX):

where p=0, 1, 2, 3, 4 or 5.

3. The polymer according to claim 2 , wherein the proportion of structural units of the formulae (I), (II), (III), (IV), (V), (VI), (VII), (VIII) and/or (IX) in the polymer is in the range from 50 to 95 mol %, based on 100 mol % of all copolymerisable monomers which are present as structural units in the polymer.

4. The polymer according to claim 2 , wherein the polymer, besides structural units of the formula (I), (II), (III), (IV), (V), (VI), (VII), (VIII) or (IX), also comprises further structural units which are different from the structural units of the formulae (I), (II), (III), (IV), (V), (VI), (VII), (VIII) or (IX).

5. A process for the preparation of a polymer according to claim 1 , comprising preparing the polymer by SUZUKI polymerisation, YAMAMOTO polymerisation, STILLE polymerisation or HARTWIG-BUCHWALD polymerisation.

6. A polymer blend comprising one or more polymer according to claim 1 which comprising at least one structural unit of the formula (I), and one or more further polymeric, oligomeric, dendritic and/or low-molecular-weight substance.

7. A solution or a formulation comprising one or more polymer according to claim 1 in one or more solvents.

8. A solution or a formulation comprising the polymer blend according to claim 6 in one or more solvents.

9. A method comprising utilizing the polymer according to claim 1 in an electronic or an opto-electronic device.

10. An electronic or an opto-electronic device, having one or more active layers, where at least one of these active layers comprises one or more polymers according to claim 1 .

11. A polymer comprising at least one structural unit of formula (I-2):

where
Ar 1 to Ar 5 is on each occurrence, in each case identically or differently, a mono- or polycyclic, aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R;
R is on each occurrence, identically or differently, H, D, F, Cl, Br, I, N(R 1 ) 2 , CN, NO 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , C(═O)R 1 , P(═O)(R 1 ) 2 , S(═O)R 1 , S(═O) 2 R 1 , OSO 2 R 1 , a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R 1 , where one or more non-adjacent CH 2 groups may be replaced by R 1 C═CR 1 , C≡C, Si(R 1 ) 2 , C═O, C═S, C═NR 1 , P(═O)(R 1 ), SO, SO 2 , NR 1 , O, S or CONR 1 and where one or more H atoms may be replaced by D, F, Cl, Br, I or CN, or a mono- or polycyclic, 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 1 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or a diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or a crosslinkable group Q, where two or more radicals R may also form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one another;
R 1 is on each occurrence, identically or differently, H, D, F or an aliphatic hydrocarbon radical having 1 to 20 C atoms, an aromatic and/or a heteroaromatic hydrocarbon radical having 5 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by F; where two or more substituents R 1 may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; and
n=1, 2 or 3,
where the dashed lines represent bonds to adjacent structural units in the polymer, characterised in that, Ar 4 and/or Ar 5 is each substituted by Ar 6 in at least one, preferably in one of the two ortho-positions, where Ar 6 is a mono- or polycyclic, aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R.

Assignees

• Merck Patent Gmbh

Inventors

• Heil Holger
• Eckes Fabrice
• Joosten Dominik
• Hayer Anna
• Stegmaier Katja

Classifications

• C08G2261/148

  Side-chains having aromatic units · CPC title

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C08G2261/411

  Suzuki reactions · CPC title

• C08G2261/76

  crosslinking · CPC title

• C08G61/12 Primary

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title