Organometallic complexes which emit in the red to green spectral region and their use in OLEDs

Patent metadata

Field	Value
Publication number	US-9522895-B2
Application number	US-201313863407-A
Country	US
Kind code	B2
Filing date	Apr 16, 2013
Priority date	Apr 4, 2007
Publication date	Dec 20, 2016
Grant date	Dec 20, 2016

Abstract

A triphenylene derivative useful for the production of organic light emitting diodes.

First claim

The invention claimed is:

1. A triphenylene derivative of the general formula IIa

in which:
R 1 is one of the formulae

where R′, R″, R′″ and R″″ are each independently hydrogen, or alkyl,
wherein R 1 optionally comprises at least one benzofusion, or
R 1 is

R 2 , R 3 , R 4 are each independently C 1 -C 20 -alkyl, where the aforementioned radical is optionally substituted with F, Cl, C 1 -C 8 -alkyl, CN or SCN;
o is from 0 to 3, where the R 3 radicals, when o>1, may be the same or different;
p is from 0 to 2, where the R 4 radicals, when p>1, may be the same or different;
n is 0;
X 2 is N, CH or CR 2 ;
X 3 is N, CH or CR 3 ; and
X 4 are each independently N, CH or CR 4 .

2. A process for preparing triphenylene derivatives according to claim 1 , comprising:
(i) preparing an arylboronic acid derivative (V) by reacting an aromatic compound of the formula IV which has been functionalized with a Y group with a corresponding boron compound:

in which
Y is halogen and
R 5 is H, C 1 -C 6 -alkyl, or two R 5 radicals form a diatomic bridge between the oxygen atoms, where the atoms of the bridge may be substituted or unsubstituted;
(ii) reacting in the presence of a palladium catalyst one equivalent of the arylboronic acid derivative of the formula V with a biphenyl derivative of the formula VI which has been functionalized with two z groups to obtain a compound of the formula VII

in which
z is halogen or OTf; and
(iii) intramolecular cyclizing in the presence of a palladium catalyst of the compound of the formula VII to obtain the desired triphenylene derivatives of the formula IIb.

3. The triphenylene derivative according to claim 1 , wherein
R 2 , R 3 , R 4 are each independently C 1 -C 8 -alkyl, where the aforementioned radicals are optionally substituted with F, Cl, C 1 -C 8 -alkyl, F, Cl, CN or SCN.

4. The triphenylene derivative according to claim 1 , wherein
R 2 , R 3 , R 4 are each independently C 1 -C 4 -alkyl, or F substituted C 1 -C 4 -alkyl.

5. The triphenylene derivative according to claim 1 , wherein R 2 , R 3 , R 4 are each CH 3 .

6. The triphenylene derivative according to claim 1 , wherein n, o and p are each 0.

7. The triphenylene derivative according to claim 1 , having one of the following formulae:

8. A triphenylene derivative of the general formula IIa

in which:
R 1 is one of the formulae

where R′, R″, R′″ and R″″ are each independently hydrogen, or alkyl,
wherein R 1 optionally comprises at least one benzofusion, or
R 1 is

R 2 , R 3 , R 4 are each independently C 1 -C 20 -alkyl, where the aforementioned radical is optionally substituted with F, Cl, C 1 -C 8 -alkyl, CN or SCN;
o is from 0 to 3, where the R 3 radicals, when o>1, may be the same or different;
p is from 0 to 2, where the R 4 radicals, when p>1, may be the same or different;
n is 0;
X 2 is CH or CR 2 ;
X 3 is CH or CR 3 ; and
X 4 are each independently CH or CR 4 .

9. A process for preparing triphenylene derivatives according to claim 8 , comprising:
(i) preparing an arylboronic acid derivative (V) by reacting an aromatic compound of the formula IV which has been functionalized with a Y group with a corresponding boron compound:

in which
Y is halogen and
R 5 is H, C 1 -C 6 -alkyl, or two R 5 radicals form a diatomic bridge between the oxygen atoms, where the atoms of the bridge may be substituted or unsubstituted;
(ii) reacting in the presence of a palladium catalyst one equivalent of the arylboronic acid derivative of the formula V with a biphenyl derivative of the formula VI which has been functionalized with two z groups to obtain a compound of the formula VII

in which
z is halogen or OTf; and
(iii) intramolecular cyclizing in the presence of a palladium catalyst of the compound of the formula VII to obtain the desired triphenylene derivatives of the formula IIb.

10. The triphenylene derivative according to claim 8 , wherein
R 2 , R 3 , R 4 are each independently C 1 -C 8 -alkyl optionally substituted with F, Cl, C 1 -C 8 -alkyl, F, Cl, CN or SCN.

11. The triphenylene derivative according to claim 8 , wherein
R 2 , R 3 , R 4 are each independently C 1 -C 4 -alkyl, or F substituted C 1 -C 4 -alkyl.

12. The triphenylene derivative according to claim 8 , wherein
n, o and p are each 0.

Assignees

• Basf Se
• Udc Ireland Ltd

Inventors

• Boerner Herbert Friedrich
• Loebl Hans-Peter
• Salbeck Josef
• Popova Elena

Classifications

• C07F15/0033

  Iridium compounds · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07D249/08

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title