Compounds and polymers which contain substituted indenofluorene derivatives as structural unit, process for the preparation thereof, and the use thereof as electronic devices and mixtures and solutions

Patent metadata

Field	Value
Publication number	US-9349960-B2
Application number	US-201013266781-A
Country	US
Kind code	B2
Filing date	May 3, 2010
Priority date	May 29, 2009
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

The present invention relates to polymers which contain substituted indenofluorene derivatives as structural unit, to substituted indenofluorene derivatives, to a process for the preparation of the polymers according to the invention, to mixtures and solutions which comprise the polymers according to the invention, and to the use of the polymers according to the invention in electronic devices, in particular in organic electroluminescent devices, so-called OLEDs (OLED=organic light emitting diode).

First claim

The invention claimed is:

1. A polymer for use as a matrix material in electroluminescent device which consists essentially of a structural unit of the formula (I):

where the symbols and indices used have the following meanings:
the dashed lines represent, independently of one another, a bond to a further structural unit of the polymer;
L 1 and L 2 represent, independently of one another, or a unit selected from the group consisting of a C 1-10 -alkylene group, C 2-10 -alkenylene group, C 2-10 -alkynylene group and Si 1-10 -silylene group, where one or more CH 2 units is optionally replaced by NR, O or S and one or more SiH 2 units is optionally replaced by O;
W represents a tetravalent unit selected from the group consisting of C, Si, Ge and a structural element of the following formulae (II) and (III):

where
D is, identically or differently on each occurrence, a unit selected from the group consisting of CR 2 , O, S and NR,
E and J are each, independently of one another, units selected from the group consisting of CR and N,
n is 1, 2 or 3, and
m is 0, 1 or 2; where
R is a radical selected from the group consisting of H, F and C 1-6 -alkyl;
with the proviso that only one representative from E, D and J is different from CR or CR 2 ;
where, in the case where the tetravalent unit W is a unit of the formula (II) or (III), C 1 and C 3 are bonded to different atoms of the unit W;
U, V and V′ represent, independently of one another, a single covalent bond or a divalent unit selected from the group consisting of CR 1 R 2 , C═O, NR 1 , O, SiR 1 R 2 , P═O, S and GeR 1 R 2 ;
where
R 1 and R 2 are selected, independently of one another, from the group consisting of H, F, a C 1-40 -alkyl group, a C 2-40 -alkenyl group, a C 2-40 -alkynyl group, an optionally substituted C 6-40 -aryl group and an optionally substituted 5- to 25-membered heteroaryl group;
C 1 to C 8 each represent a C atom;
Ar 1 and Ar 2 each represent, independently of one another, a 5- to 25-membered, optionally substituted aromatic or heteroaromatic ring system;
Ar 3 , Ar 4 and Ar 5 represent, independently of one another, an optionally substituted C 6-40 -aryl group or an optionally substituted 5- to 25-membered heteroaryl group, where C atoms C 1 and C 2 are part of Ar 3 , C atoms C 3 to C 6 are part of Ar 4 and C atoms C 7 and C 8 are part of Ar 5 .

2. The polymer according to claim 1 , wherein U, V and V′ represent, independently of one another, a single covalent bond or CR 1 R 2 .

3. A process for the preparation of the polymer according to claim 1 , which comprises preparing the polymer by SUZUKI, YAMAMOTO, STILLE or HARTWIG-BUCHWALD polymerization.

4. A mixture comprising the polymer according to claim 1 with a low-molecular-weight substance which is a triplet emitter.

5. A solution comprising the mixture according to claim 4 in one or more solvents.

6. A solution comprising the polymer according to claim 1 in one or more solvents.

7. A polymer for use as a matrix material in electroluminescent device which consists essentially of a structural unit of the formula (I):

where the symbols and indices used have the following meanings:
the dashed lines represent, independently of one another, a bond to a further structural unit of the polymer;
L 1 and L 2 represent, independently of one another, a single covalent bond or a unit selected from the group consisting of a C 1-10 -alkylene group, C 2-10 -alkenylene group, C 2-10 -alkynylene group and Si 1-10 -silylene group, where one or more CH 2 units is optionally replaced by NR, O or S and one or more SiH 2 units is optionally replaced by O;
W represents a tetravalent unit selected from the group consisting of C, Si, Ge— and a structural element of the following formulae (II) and (III):

where
D is, identically or differently on each occurrence, a unit selected from the group consisting of CR 2 , O, S and NR,
E and J are each, independently of one another, units selected from the group consisting of CR and N,
n is 1, 2 or 3, and
m is 0, 1 or 2; where
R is a radical selected from the group consisting of H, F and C 1-6 -alkyl;
with the proviso that only one representative from E, D and J is different from CR or CR 2 ;
where, in the case where the tetravalent unit W is a unit of the formula (II) or (III), C 1 and C 3 are bonded to different atoms of the unit W;
U, V and V′ represent, independently of one another, a divalent unit selected from the group consisting of CR 1 R 2 , C═O, NR 1 , O, SiR 1 R 2 , P═O, S and GeR 1 R 2 ;
where
R 1 and R 2 are selected, independently of one another, from the group consisting of H, F, a C 1-40 -alkyl group, a C 2-40 -alkenyl group, a C 2-40 -alkynyl group, an optionally substituted C 6-40 -aryl group and an optionally substituted 5- to 25-membered heteroaryl group;
C 1 to C 8 each represent a C atom;
Ar 1 and Ar 2 each represent, independently of one another, a 5- to 25-membered, optionally substituted aromatic or heteroaromatic ring system;
Ar 3 , Ar 4 and Ar 5 represent, independently of one another, an optionally substituted C 6-40 -aryl group or an optionally substituted 5- to 25-membered heteroaryl group, where C atoms C 1 and C 2 are part of Ar 3 , C atoms C 3 to C 6 are part of Ar 4 and C atoms C 7 and C 8 are part of Ar 5 .

8. A process for the preparation of the polymer according to claim 7 , which comprises preparing the polymer by SUZUKI, YAMAMOTO, STILLE or HARTWIG-BUCHWALD polymerization.

9. A mixture comprising the polymer according to claim 7 with a low-molecular-weight substance which is a triplet emitter.

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

11. A solution comprising the polymer according to claim 7 in one or more solvents.

12. The polymer according to claim 7 , wherein U, V and V′ represent, independently of one another, a single covalent bond or CR 1 R 2 .

13. An electronic device having at least one emitting layer which comprises
a polymer which consists essentially of a structural unit of the formula (I):

where the symbols and indices used have the following meanings:
the dashed lines represent, independently of one another, a bond to a further structural unit of the polymer;
L 1 and L 2 represent a single covalent bond
W represents a tetravalent unit selected from the group consisting of C,
U, V and V′ represent, independently of one another, a single covalent bond or a divalent unit selected from the group consisting of CR 1 R 2 , C═O, NR 1 , O, SiR 1 R 2 , P═O, S and GeR 1 R 2 ;
where
R 1 and R 2 are selected, independently of one another, from the group consisting of H, F, a C 1-40 -alkyl group, a C 2-40 -alkenyl group, a C 2-40 -alkynyl group, an optionally substituted C 6-40 -aryl group and an optional

Assignees

• Heun Susanne
• Ludemann Aurélie
• Anémian Rémi Manouk
• Pan Junyou
• Eberle Thomas
• Merck Patent Gmbh

Inventors

• Heun Susanne
• Ludemann Aurélie
• Anémian Rémi Manouk
• Pan Junyou
• Eberle Thomas

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• C09B69/103

  containing a diaryl- or triarylmethane dye · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0037

  Electricity · mapped topic

• C08G2261/524

  phosphorescent · CPC title