Source: https://patents.google.com/patent/US10008677B2/en
Timestamp: 2019-09-19 06:42:07
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Matched Legal Cases: ['Application No. 2013', 'Application No. 2013', 'Application No. 2013', 'Application No. 2013', 'Application No. 201210371182', 'Application No. 201210371182']

US10008677B2 - Materials for organic light emitting diode - Google Patents
Materials for organic light emitting diode Download PDF
US10008677B2
US10008677B2 US13/932,546 US201313932546A US10008677B2 US 10008677 B2 US10008677 B2 US 10008677B2 US 201313932546 A US201313932546 A US 201313932546A US 10008677 B2 US10008677 B2 US 10008677B2
US13/932,546
US20130299795A1 (en
2013-07-01 Priority to US13/932,546 priority patent/US10008677B2/en
2013-07-09 Assigned to UNIVERSAL DISPLAY CORPORATION reassignment UNIVERSAL DISPLAY CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LI, DAVID ZENAN, ADAMOVICH, VADIM, ALLEYNE, BERT, DEANGELIS, ALAN, FIORDELISO, JAMES, MA, BIN, XIA, CHUANJUN
2013-08-01 Assigned to UNIVERSAL DISPLAY CORPORATION reassignment UNIVERSAL DISPLAY CORPORATION CORRECTIVE ASSIGNMENT TO CORRECT THE CORRECTIVE ASSIGNMENT TO CORRECT THE THE ERROR OF THE APPLICATION SERIAL NUMBER PREVIOUSLY RECORDED ON REEL 030754 FRAME 0717. ASSIGNOR(S) HEREBY CONFIRMS THE APPLICATION SERIAL NUMBER SHOULD BE CORRECTED FROM 13/932,548 TO 13/932,546.. Assignors: ADAMOVICH, VADIM, ALLEYNE, BERT, DEANGELIS, ALAN, FIORDELISO, JAMES, LI, DAVID ZENAN, MA, BIN, XIA, CHUANJUN
2013-11-14 Publication of US20130299795A1 publication Critical patent/US20130299795A1/en
2018-06-26 Publication of US10008677B2 publication Critical patent/US10008677B2/en
Compounds are provided that comprise a ligand having a 5-substituted 2-phenylquinoline. In particular, the 2-phenylquinoline may be substituted with a cycloalkyl containing group at the 5-position. These compounds may be used in organic light emitting devices, in particular as red emitters in the emissive layer of such devices, to provide devices having improved properties.
This application is a continuation-in-part of U.S. patent application Ser. No. 13/006,016, filed on Jan. 13, 2011, the entire contents of which is incorporated herein by reference.
The present invention relates to organic light emitting devices (OLEDs). More specifically, the present invention is related to phosphorescent materials comprising a ligand having 2-phenylquinoline substituted with a cylcoalkyl group at the 5-position. These materials may be used in OLEDs to provide devices having improved performance.
wherein R1, R2, R3, R5, R6 and R7 are independently selected from the group consisting of hydrogen, deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl. R4 is selected from the group consisting of alkyl having at least 2 carbon atoms, amino, alkenyl, alkynyl, arylkyl, and silyl. m is 1, 2, or 3. Preferably, each of R1 and R3 are a branched alkyl with branching at a position further than the α position to the carbonyl group.
In one aspect, R4 comprises a cycloalkyl group having at least 4 carbon atoms. Specific, non-limiting examples of the 5-substituted 2-phenylquinoline containing compound having Formula III wherein R4 comprises a cycloalkyl group having at least 4 carbon atoms is selected from the group consisting of Compound II-1-Compound II-72.
FIG. 3 shows an exemplary compound comprising a 5-substituted 2-phenylquinoline ligand (top) and a preferred embodiment of the 5-substituted 2-phenylquinoline compound (bottom).
In another aspect, R4 in compound having Formula III comprises a cycloalkyl group having at least 4 carbon atoms. The inventors have discovered that provision of cycloalkyl substituent at 5-position of the 2-phenylquinoline provides further improvement in the phosphorescent characteristics of the compound over linear or branched alkyl group substituents. This improved compound is suitable as red emitters in Phosphorescent OLEDs. Specific, non-limiting examples of the 5-substituted 2-phenylquinoline containing compound having Formula III wherein R4 comprises a cycloalkyl group having at least 4 carbon atoms is selected from the group consisting of Compound II-1-Compound II-72 shown below.
R1, R2, R3, R5, R6 and R7 are independently selected from the group consisting of hydrogen, deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl.
R4 is selected from the group consisting of alkyl having at least 2 carbon atoms, amino, alkenyl, alkynyl, arylkyl, and silyl. m is 1, 2, or 3.
In another aspect, the organic layer comprises a compound having Formula III wherein R4 is a cycloalkyl group having at least 4 carbon atoms. Specific, non-limiting examples of the compound having Formula III wherein R4 is a cycloalkyl group having at least 4 carbon atoms is selected from the group consisting of Compound II-1-Compound II-72 disclosed herein.
Ar1 to Ar9 has the similar definition as Ar's mentioned above.
Triarylamine with (di)benzothiophene/(di)ben- zofuran
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Metal coordination complexes (e.g., Zn, Al with N{circumflex over ( )}N ligands)
Blues hosts
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Zn (N{circumflex over ( )}N) complexes
EXPERIMENTAL Compound Examples Example 1. Synthesis of Compound 1
Synthesis of Iridium Dimer.
Synthesis of Compound II-2 Synthesis of 5-cyclopentyl-2-(3,5-dimethylphenyl)quinoline
5-Chloro-2-(3,5-dimethylphenyl)quinoline (14.0 g, 52.3 mmol) and [1,3-bis(diphenylphosphino)propane]-dichloronickel (II) (0.10 g, 0.19 mmol) were dissolved in 250 mL of anhydrous diethyl ether under N2 atm. The reaction mixture was degassed and solution of cyclopentylmagnesium iodide (2 M solution in ether, 52 ml, 105 mmol) was added dropwise. The reaction mixture was stirred for 1 h, quenched with 20% aq. solution of ammonium chloride and extracted with ethyl acetate. The organic solution was dried over sodium sulfate, filtered and evaporated, providing yellow solid. Purification with column chromatography on silica gel, eluted with hexane/ethyl acetate 9/1 (v/v) mixture followed by crystallization from heptanes provided 5-cyclopentyl-2-(3,5-dimethylphenyl)quinoline as colorless crystals (12 g, 76% yield).
Iridium complex dimer (2.17 g, 1.31 mmol), acetylacetonate (1.31 g, 13.1 mmol) and potassium carbonate (1.81 g, 13.1 mmol) were suspended in 70 mL of ethoxyethanol, and stirred overnight under N2 at room temperature. The reaction mixture was then filtered through a pad of Celite®, washed with MeOH. Most of the red material was solubilized and passed through the Celite®. The Celite® was suspended in DCM, containing 10% of triethylamine and this suspension was combined with filtrate and evaporated. The residue was purified by column chromatography on silica gel, pre-treated with Et3N, eluted with hexane/dichloromethane mixture, providing a dark red solid. The product was further purified by recrystallizing from dichloromethane and isopropanol mixture to give desired product (1.67 g, 72% yield).
The organic stack of the device examples consisted of sequentially, from the 1200 Å ITO surface, 100 Å of Compound A as the hole injection layer (HIL), 400 Å of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (α-NPD) as the hole transporting layer (HTL), 300 Å of the 7 wt % invention compound doped into BAlq host as the emissive layer (EML), 550 Å of Alq3 (tris-8-hydroxyquinoline aluminum) as the ETL.
Compound 1 0.665 0.331 622 58 7.8 22.2 20.5 9.0 1.08 6,852 600 66
Additional device examples were fabricated to evaluate the compound having Formula III wherein R4 comprises a cycloalkyl group. These additional example devices were fabricated by high vacuum (<10−7 Torr) thermal evaporation. The anode electrode is 1200 Å of ITO. The cathode consisted of 10 Å of LiF followed by 1,000 Å of Al. All devices are encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box (<1 ppm of H2O and O2) immediately after fabrication, and a moisture getter was incorporated inside the package.
The organic stack of the additional device examples consisted of sequentially, from the ITO surface, 100 Å of Compound A as the HIL, 400 Å of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (α-NPD) as the HTL, 300 Å of the invention compound doped in Balq as host with 6 wt % of an Ir phosphorescent compound as the EML, 550 Å of Alq3 (tris-8-hydroxyquinoline aluminum) as the ETL.
The device structures and device data from the additional device examples are summarized in Table 3 below.
Alq 1931 CIE λ max FWHM Volt LE EQE PE cd/Aper
Emitter [Å] x y [nm] [nm] [V] [cd/A] [%] [lm/W] EQE
Compound II-2 550 Å 0.662 0.335 620 60 8.3 23.2 20.4 8.8 1.1
As can be seen from Table 3, the example device with Compound II-2 showed saturated red color and high luminous efficiency. The LE was measured at 23.2 cd/A compared to 22.2 cd/A for Compound 1.
wherein R1, R2, R3, R5, R6 and R7 are independently selected from the group consisting of hydrogen, deuterium, alkyl, silyl, alkoxy, amino, alkenyl, alkynyl, arylkyl, aryl and heteroaryl;
wherein R4 comprises an unsubstituted cycloalkyl group selected from the group consisting of cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl; and
2. The compound of claim 1, wherein R4 is an unsubstituted cyclobutyl moiety.
3. The compound of claim 1, wherein R4 is an unsubstituted cylopentyl moiety.
4. The compound of claim 1, wherein R4 is an unsubstituted cyclohexyl moiety.
5. The compound of claim 1, wherein R4 is an unsubstituted cycloheptyl moiety.
6. The compound of claim 1, wherein R4 is an unsubstituted cycloalkyl group selected from the group consisting of cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.
7. The compound of claim 1, wherein each of R1 and R3 is a branched alkyl with branching at a position further than the α position to the carbonyl group.
8. The compound of claim 1, wherein each of R5 and R7 are methyl, and R6 is hydrogen.
9. The compound of claim 1, wherein each of R5 and R6 are methyl, and R7 is hydrogen.
10. The compound of claim 1, wherein each of R5, R6 and R7 are methyl.
13. The first device of claim 12, wherein each of R1 and R3 is a branched alkyl with branching at a position further than the α position to the carbonyl group.
14. The first device of claim 12, wherein each of R5, R6 and R7 are independently selected from methyl and hydrogen, and at least one of R5, R6 and R7 is methyl.
15. The first device of claim 12, wherein each of R5 and R7 are methyl, and R6 is hydrogen.
16. The first device of claim 12, wherein each of R5 and R6 are methyl, and R7 is hydrogen.
17. The first device of claim 12, wherein each of R5, R6, and R7 are methyl.
18. The first device of claim 12, wherein the compound is selected from the group consisting of:
19. The first device of claim 12, wherein the organic layer is an emissive layer and the compound is an emissive dopant.
20. The first device of claim 19, wherein the organic layer further comprises a host.
21. The first device of claim 20, wherein the host is a metal 8-hydroxyquinolate.
22. The first device of claim 21, wherein the host is
23. The first device of claim 12, wherein the first device is selected from the group consisting of a consumer product, an organic light emitting device, and combinations thereof.
US13/932,546 2011-01-13 2013-07-01 Materials for organic light emitting diode Active 2033-04-01 US10008677B2 (en)
US15/989,854 Continuation US20180277775A1 (en) 2011-01-13 2018-05-25 Materials for organic light emitting diodes
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US13/932,546 Active 2033-04-01 US10008677B2 (en) 2011-01-13 2013-07-01 Materials for organic light emitting diode
US15/989,854 Pending US20180277775A1 (en) 2011-01-13 2018-05-25 Materials for organic light emitting diodes
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