IP Library Granted Patent US 8,697,255
Granted Patent B2
US 8,697,255 · App. 12/667,765 · Granted Apr 15, 2014

Organic light-emitting diodes comprising at least one disilyl compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzopholes, disilyldibenzothiophene S-oxides and disilyldibenzothiophene S,S-dioxides

Inventors: Nicolle Langer (Heppenheim, DE); Klaus Kahle (Ludwigshafen, DE); Christian Lennartz (Schifferstadt, DE); Oliver Molt (Hirschberg, DE); Evelyn Fuchs (Mannheim, DE); Jens Rudolph (Worms, DE); Christian Schildknecht (Mannheim, DE); Soichi Watanabe (Mannheim, DE); Gerhard Wagenblast (Wachenheim, DE)
Assignee: BASF SE
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Quick Facts
Patent No.
US 8,697,255
App. No.
12/667,765
Granted
Apr 15, 2014
Kind
B2
Abstract

The present invention relates to an organic light-emitting diode comprising an anode and a cathode Ka and a light-emitting layer E and if appropriate at least one further layer, where the light-emitting layer E and/or the at least one further layer comprises at least one compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophene S-oxides and disilyldibenzothiophene S,S-dioxides, to a light-emitting layer comprising at least one of the aforementioned compounds, to the use of the aforementioned compounds as matrix material, hole/exciton blocker material, electron/exciton blocker material, hole injection material, electron injection material, hole conductor material and/or electron conductor material, and to a device selected from the group consisting of stationary visual display units, mobile visual display units and illumination units comprising at least one inventive organic light-emitting diode.

Claims (36)

1. An organic light-emitting diode comprising an anode and a cathode Ka and a light-emitting layer E and optionally at least one further layer, selected from the group consisting of: at least one blocking layer for electrons/excitons, at least one blocking layer for holes/excitons, at least one hole injection layer, at least one hole conductor layer, at least one electron injection layer and at least one electron conductor layer, wherein the organic light-emitting diode comprises at least one hole/exicton blocker layer, the compound of the general formula (I) is present exclusively in the light-emitting layer and in the hole/exciton blocker layer,

in which:

X is NR 1 or O

R 1 is substituted C6-C30-aryl, or substituted or unsubstituted heteroaryl having from 5 to 30 ring atoms, wherein R 1 radical comprises N, O or F;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7

are each independently substituted or unsubstituted C 1 -C 20 -alkyl, or substituted or unsubstituted C 6 -C 30 -aryl, or a structure of the general formula (c)

R a , R b

are each independently substituted or unsubstituted C 1 -C 20 -alkyl, substituted or unsubstituted C 6 -C 30 -aryl, or substituted or unsubstituted heteroaryl having from 5 to 30 ring atoms or a substituent with donor or acceptor action selected from the group consisting of: C 1 -C 20 -alkoxy, C 6 -C 30 -aryloxy, C 1 -C 20 -alkylthio, C 6 -C 30 -arylthio, SiR 14 R 15 R 16 , halogen radicals, halogenated C 1 -C 20 -alkyl radicals, carbonyl (—CO(R 14 )), carbonylthio (—C═O(SR 14 )), carbonyloxy (—C═O(OR 14 )), oxycarbonyl (—OC═O(R 14 )), thiocarbonyl (—SC═O(R 14 )), amino (—NR 14 R 15 ), OH, pseudohalogen radicals, amido (—C═O(NR 14 )), —NR 14 C═O(R 15 ), phosphonate (—P(O)(OR 14 ) 2 , phosphate (—OP(O)(OR 14 ) 2 ), phosphine (—PR 14 R 15 ), phosphine oxide (—P(O)R 14 2 ), sulfate (—OS(O) 2 OR 14 ), sulfoxide (—S(O)R 14 ), sulfonate (—S(O) 2 OR 14 ), sulfonyl (—S(O) 2 R 14 ), sulfonamide (—S(O) 2 NR 14 R 15 ), NO 2 , boronic esters (—OB(OR 14 ) 2 ), imino (—C═NR 14 R 15 )), borane radicals, stannane radicals, hydrazine radicals, hydrazone radicals, oxime radicals, nitroso groups, diazo groups, vinyl groups, sulfoximines, alanes, germanes, boroximes and borazines;

R 14 , R 15 , R 16

are each independently substituted or unsubstituted C1-C20-alkyl, or substituted or unsubstituted C6-C30-aryl; and

q,r are each independently 0, 1, 2 or 3; where, in the case when q or r is 0, all substitutable positions of the aryl radical are substituted by hydrogen,

where the radicals and indices X′″, R 5 ′″, R 6 ′″, R 7 ′″, R a ′″, R b ′″, q′″ and r′″ in formula (c) are each independently as defined for the radicals and indices X, R 5 , R 6 , R 7 , R a , R b , q and r of the compounds of formula (I).

2. The organic light-emitting diode according to claim 1 , wherein at least one of the R 2 , R 3 and R 4 radicals and/or at least one of the R 5 , R 6 and R 7 radicals is substituted or unsubstituted C 6 -C 30 -aryl.

3. The organic light-emitting diode according to claim 1 , wherein the compound of the general formula (I) is a 3,6-disilyl-substituted compound of the general formula (Ia):

in which:

X is NR 1 or O;

R 1 is substituted C 6 -C 30 -aryl, or substituted or unsubstituted heteroaryl having from 5 to 30 ring atoms, wherein R 1 comprises N, O or F;

R 2 , R 3 , R 4 , R 5 , R 6 , R7

are each independently substituted or unsubstituted C 1 -C 20 -alkyl or substituted or unsubstituted C 6 -C 30 -aryl or a structure of the general formula (c); and

R 8 , R 9 , R 10 , R 11 , R 12 , R 13

are each independently hydrogen or are each independently substituted or unsubstituted C 1 -C 20 -alkyl, substituted or unsubstituted C 6 -C 30 -aryl, substituted or unsubstituted heteroaryl having from 5 to 30 ring atoms or a substituent with donor or acceptor action; or SiR 14 R 15 R 16 ; where R 14 , R 15 and R 16 are each independently substituted or unsubstituted C 1 -C 20 -alkyl or substituted or unsubstituted phenyl.

4. The organic light-emitting diode according to claim 3 , wherein:

X is NR 1 ;

R 1 is substituted C 6 -C 30 -aryl, wherein R 1 comprises N, O or F;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7

are each independently substituted or unsubstituted C 1 -C 20 -alkyl or substituted or unsubstituted C 6 -C 30 -aryl, or a structure of the general formula (c) where at least one of the R 2 , R 3 and R 4 radicals and/or at least one of the R 5 , R 6 and R 7 radicals is substituted or unsubstituted C 6 -C 30 -aryl;

R 8 , R 9 , R 10 , R 11 , R 12 , R 13

are each independently hydrogen or are each independently substituted or unsubstituted C 1 -C 20 -alkyl, substituted or unsubstituted C 6 -C 30 -aryl, substituted or unsubstituted heteroaryl having from 5 to 30 ring atoms or a substituent with donor or acceptor action; or SiR 14 R 15 R 16 ; and

R 14 , R 15 , R 16

are each independently substituted or unsubstituted C 1 -C 20 -alkyl or substituted or unsubstituted C 6 -C 30 -aryl.

5. The organic light-emitting diode according to claim 1 , wherein the R 1 radical is substituted C 6 -aryl of the following formula:

in which

p is 1, 2, 3, 4 or 5; and

R 17 is C 1 -C 6 alkoxy, CN, CF 3 or F.

6. A method of making the organic light-emitting diode according to claim 1 , comprising providing the compound of general formula (I) wherein the organic light-emitting diode comprises at least one hole/exciton blocker layer such that the compound of the general formula (I) is provided exclusively to the light-emitting layer and the hole/exciton blocker layer.

7. 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 1 .

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE INCORRECT APPL. NO. 14/901,736 PREVIOUSLY RECORDED AT REEL: 039460 FRAME: 0615. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 8, 2017
From: BASF SE
To: UDC IRELAND LIMITED
Reel/Frame 042740/0222 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2016
From: BASF SE
To: UDC IRELAND LIMITED
Reel/Frame 039460/0615 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 1, 2010
From: LANGER, NICOLLE; KAHLE, KLAUS; LENNARTZ, CHRISTIAN; MOLT, OLIVER; FUCHS, EVELYN; RUDOLPH, JENS; SCHILDKNECHT, CHRISTIAN; WATANABE, SOICHI; WAGENBLAST, GERHARD
To: BASF SE
Reel/Frame 025225/0602 →
Priority Claims (2)
EP 07111824 · Jul 5, 2007 · regional
EP 08153306 · Mar 26, 2008 · regional
Continuity (1)
Related Publication 20110031477A1 · Feb 10, 2011