USE OF ACRIDINE DERIVATIVES AS MATRIX MATERIALS AND/OR ELECTRON BLOCKERS IN OLEDS

• US 20100219406A1
• Filed: 09/26/2008
• Published: 09/02/2010
• Est. Priority Date: 10/02/2007
• Status: Active Grant

• Current Assignee: UDC Ireland Limited
• Original Assignee: BASF SE
• Inventors: Nord, Simon, Molt, Oliver, Fuchs, Evelyn, Lennartz, Christian, Schildknecht, Christian, Kahle, Klaus, Rudolph, Jens, Langer, Nicolle
• Granted Patent: US 8,384,068 B2
• Time in Patent Office: Days
• US Class Current: 257/40
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

The present invention relates to the use of (hetero)aryl-substituted acridine derivatives as matrix materials in a light-emitting layer of organic light-emitting diodes (OLEDs) and/or in a blocking layer for electrons in organic light-emitting diodes. The present invention further relates to a light-emitting layer which comprises at least one emitter material and at least one matrix material, wherein the matrix material used is at least one (hetero)aryl-substituted acridine derivative, and to an organic light-emitting diode which comprises at least one inventive light-emitting layer, to an organic light-emitting diode which comprises at least one acridine derivative of the formula (I) in a blocking layer for electrons, and to a device selected from stationary and mobile visual display units and illumination units which comprise at least one inventive organic light-emitting diode.

Claims

1-13. -13. (canceled)

14. An organic light-emitting diode comprising an acridine derivative of the general formula (I) as matrix material in a light-emitting layer of the organic light-emitting diode and/or as electron blocker in the organic light-emitting diode

in which:

(Het)Ar¹,

(Het)Ar² are each independently an unsubstituted or substituted aryl radical or an unsubstituted or substituted heteroaryl radical;

R¹ is an unsubstituted or substituted alkyl radical which may be linear or branched, an unsubstituted or substituted cycloalkyl radical, an unsubstituted or substituted heterocycloalkyl radical, an unsubstituted or substituted aryl radical, or an unsubstituted or substituted heteroaryl radical;

R², R³ are each independently an unsubstituted or substituted alkyl radical which may be linear or branched, an unsubstituted or substituted cycloalkyl radical, an unsubstituted or substituted heterocycloalkyl radical, an unsubstituted or substituted aryl radical, an unsubstituted or substituted heteroaryl radical, or a silyl radical;

n, m are each independently 0, 1, 2, 3 or 4, where, in the case that n or m is 0, all positions in the acridine base skeleton substitutable by R² or R³ are hydrogen;

 

is not present; and

 

is an optional bridge composed of 0, 1 or 2 atoms which bonds the R¹ radical covalently to one of the substitutable carbon atoms of the acridine skeleton,

wherein the acridine derivatives of the formula (I) have an energy of the lowest triplet state of at least 2.6 eV.

15. The organic light-emitting diode according to claim 14, wherein the acridine derivatives of the formula (I) are used as matrix materials and/or electron blockers for triplet emitters.

16. The organic light-emitting diode to claim 14, wherein the R¹ radical is an unsubstituted or substituted C₁- to C₈-alkyl radical which may be linear or branched, an unsubstituted or substituted C₆-C₁₄-aryl radical or an unsubstituted or substituted heteroaryl radical having from 5 to 14 ring atoms.

17. The organic light-emitting diode to claim 16, wherein the R¹ radical is an unsubstituted C₁- to C₄-alkyl radical which may be linear or branched, an unsubstituted or substituted phenyl radical, an unsubstituted or substituted biphenyl radical, an unsubstituted or substituted pyridyl radical, an unsubstituted or substituted pyrimidyl radical, an unsubstituted or substituted benzofuryl radical, an unsubstituted or substituted dibenzofuryl radical, an unsubstituted or substituted benzothienyl radical, an unsubstituted or substituted dibenzothienyl radical, an unsubstituted or substituted carbazolyl radical or an unsubstituted or substituted triazine radical.

18. The organic light-emitting diode according to claim 14, wherein the (Het)Ar¹ and (Het)Ar² radicals are each independently selected from the group consisting of unsubstituted and substituted C₆- to C₁₄-aryl radicals and unsubstituted and substituted heteroaryl radicals having from 5 to 14 ring atoms.

19. The organic light-emitting diode according to claim 18, wherein the (Het)Ar¹ and (Het)Ar² radicals are selected from the group consisting of unsubstituted and substituted phenyl, unsubstituted and substituted biphenyl, unsubstituted and substituted pyridyl, unsubstituted and substituted pyrimidyl, unsubstituted and substituted triazinyl, unsubstituted and substituted benzofuryl, unsubstituted and substituted benzothienyl, unsubstituted and substituted benzimidazolyl, unsubstituted and substituted dibenzofuryl, unsubstituted and substituted dibenzothienyl and unsubstituted and substituted carbazolyl.

20. The organic light-emitting diode according to claim 14, wherein the radicals and symbols in the acridine derivatives of the formula (I) are each defined as follows:

(Het)Ar¹,

(Het)Ar² are each independently phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of CN, —

OC(O)Ph, carbazolyl, pyridyl, CF₃,

pyridyl, pyrimidyl, triazinyl, oxazolyl, oxadiazolyl, each of which is unsubstituted or substituted by phenyl;

benzimidazolyl which is unsubstituted or substituted by phenyl;

benzofuryl, dibenz;

ofuryl, benzothienyl, dibenzothienyl and carbazolyl, each of which is unsubstituted or substituted by phenyl;

R¹ is phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of CH₃, CN, OCH₃, carbazolyl,

biphenyl, benzofuryl or a radical of the formula

where (Het)Ar¹ and (Het)Ar² are each as defined above, and

R′

is an unsubstituted or substituted alkyl radical which may be linear or branched, an unsubstituted or substituted cycloalkyl radical, an unsubstituted or substituted heterocycloalkyl radical, an unsubstituted or substituted aryl radical, an unsubstituted or substituted heteroaryl radical;

n, m are each 0; and

are not present.

21. The organic light-emitting diode according to claim 14, wherein (Het)Ar¹ and (Het)Ar² in the acridine derivatives of the formula (I) are identical.

22. A light-emitting layer comprising at least one emitter material and at least one matrix material, wherein the matrix material used is at least one acridine derivative of the formula (I) according to claim 14.

23. An organic light-emitting diode comprising at least one light-emitting layer according to claim 22.

24. An organic light-emitting diode comprising at least one acridine derivative of the formula (I) according to claim 14 in a blocking layer for electrons.

25. A device selected from the group consisting of a stationary visual display unit, a mobile visual display unit and an illumination unit, comprising at least one organic light-emitting diode according to claim 23.

26. A device selected from the group consisting of a stationary visual display unit, a mobile visual display unit and an illumination unit, comprising at least one organic light-emitting diode according to claim 24.