CN108164564A - A kind of metal iridium complex and the organic electroluminescence device comprising the metal iridium complex - Google Patents
A kind of metal iridium complex and the organic electroluminescence device comprising the metal iridium complex Download PDFInfo
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- CN108164564A CN108164564A CN201810134626.XA CN201810134626A CN108164564A CN 108164564 A CN108164564 A CN 108164564A CN 201810134626 A CN201810134626 A CN 201810134626A CN 108164564 A CN108164564 A CN 108164564A
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 32
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000002184 metal Substances 0.000 title claims abstract description 23
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 22
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 46
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- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
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- 238000006467 substitution reaction Methods 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 11
- -1 deuterium hydrogen Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000011368 organic material Substances 0.000 claims description 7
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- 229920002866 paraformaldehyde Polymers 0.000 description 1
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000005395 radioluminescence Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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Abstract
A kind of organic electroluminescence device the invention discloses metal iridium complex and comprising the metal iridium complex, the general structure of the metal iridium complex is shown in formula I.Metal iridium complex electroluminescent proposed by the present invention is green to red, and luminous efficiency is high, while the thermal stability of material is good, and material is easily prepared, is easily purified, and is the ideal chose as organic electroluminescence device luminescent material.
Description
Technical field
The present invention relates to organic electroluminescent LED technical fields.More particularly, to a kind of metal iridium complex and
Organic electroluminescence device comprising the metal iridium complex.
Background technology
Organic electroluminescent (abbreviation OLED) and relevant research are found that first early in pope in 1963 et al. to organise
Close the electro optical phenomenon of object monocrystalline anthracene.One kind has been made with the method for vapor deposition organic molecule in the Kodak in the U.S. in 1987
Amorphous membranous type device, driving voltage is fallen below within 20V.This kind of device is due to ultra-thin, all solidstate, self-luminous, bright
Degree is high, visual angle is wide, fast response time, and driving voltage is low, small power consumption, bright in luster, contrast is high, technical process is simple, temperature
Characteristic is good, the advantages that soft display can be achieved, and can be widely applied to flat-panel monitor and area source, therefore obtained widely grinding
Study carefully, develop and use.
Electroluminescent organic material is divided into two major class：Organic electroluminescent fluorescent materials and organic electromechanical phosphorescent material, wherein having
Machine electroluminescent fluorescent is singlet excitons Radiation-induced deactivation as a result, different from luminescence generated by light, in Organic Light Emitting Diodes, three lines
State exciton and singlet exciton generate simultaneously.The generation ratio of usual singlet exciton and triplet excitons is 1：3, and root
Prohibit effect according to what the taboo of quantum statistics was counted, non-radiative decay mainly occurs for triplet excitons, and contribution is minimum to shining, only singly
Line state exciton radioluminescence, therefore, for organic/electrostrictive polymer fluorescent device, luminous efficiency is difficult to the basic reason improved
It is luminescence process shining for singlet exciton.
Early stage organic luminescent device is studied, people are to propose the imagination of triplet emission, and Forrest groups are with eight
Red electrophosphorescence luminescent device, outer quantum has been made in ethyl porphyrin platinum dopant in small molecule host material 8-hydroxyquinoline aluminum
Efficiency reaches 4%, and so far, the research of electroluminescent phosphorescence, which starts to obtain academia, greatly to be paid close attention to, and organic in subsequent several years
Electroluminescent phosphorescence, which is studied, to be rapidly developed.Wherein complex of iridium because its triplet lifetime it is shorter, have preferable luminescent properties,
It is to develop at most to be also a kind of best phosphor material of application prospect, since phosphor material has stronger triplet state in solids
Quenching typically by the use of complex of iridium as doping guest materials, makees doped body material with the material of wider band gap, passes through energy
Exciton is directly trapped on object the acquisition high-luminous-efficiency that shines by amount transfer.
Organic electroluminescence green phosphorescent material is the earliest of research and develops most ripe a kind of material.Hino in 2004
Phosphorescent devices are made Deng with the mode of spin coating, external quantum efficiency is up to 29cd/A, the height that this simple Devices structure is realized
Efficiency is attributable to the good film forming of material and main body to the energy transfer of guest materials.Adachi etc. is by (ppy) 2Ir
(acac) it is doped in TAZ, using HMTPD as hole transmission layer, it is 20% to obtain maximum external quantum efficiency, and energy efficiency is
The green device of 65lm/W, is computed, and internal quantum efficiency is almost close to 100%, and triplet excitons and singlet exciton are simultaneously
It is utilized.
From the point of view of luminescent color, compared to the phosphor material of other colors, the development of blue light electromechanical phosphorescent material not only rises
Step is the latest, also least preferable, is still a subject for being rich in challenge so far.Mechanism study shows with triplet liter
Height, not only the rate of radiation transistion become larger, be accompanied by the increase of nonradiative transition rate, and the often increase amplitude of the latter
Become apparent from, total function and effect decline luminous efficiency instead, this result in blue light material study in emission wavelength blue shift and
High efficiency is difficult to realize simultaneously, care for often this it is thin that.Therefore there has been no the superior blue phosphor materials of comprehensive performance so far to be reported
Road.
Invention content
In order to solve the above technical problems, it shines the present invention provides a kind of as green to red and high luminous efficiency gold
Belong to complex of iridium and the organic electroluminescence device comprising the metal iridium complex.
The present invention specifically provides the metal iridium complex shown in a kind of Formulas I：
Wherein：
R1And R2Each independently represent the alkyl of C1-C10, the cycloalkyl of C4-C10, deuterium substitution C1-C10 alkyl,
The alkoxy of C1-C8, the alkylthio group of C1-C8, the deuterium that the cycloalkyl of C4-C10 of deuterium substitution, the alkoxy of C1-C8, deuterium replace take
Alkylthio group, fluorine or the cyano of the C1-C8 in generation；
R3、R4、R5Each independently represent alkyl, the C1-C8 of C1-C8 that hydrogen, deuterium hydrogen, fluorine, the alkyl of C1-C8, deuterium replace
Alkoxy, deuterium substitution the alkoxy of C1-C8, the silylation of C1-C8, substituted or unsubstituted C6-C20Aryl, substitution
Or unsubstituted C6-C20Aryloxy group, substituted or unsubstituted C6-C20Arylthio, fluorine or cyano；
The substituted C6-C20Aryl, the C of substitution6-C20Aryloxy group and the C of substitution6-C20Substitution described in arylthio
Base is each independently selected from hydrogen, deuterium hydrogen, halogen atom, hydroxyl, cyano, C1-C20Alkyl, C2-C20Alkenyl, C2-C20Alkynyl, C1-C20
Alkoxy, C3-C20Cycloalkyl group or C3-C20It is one or more in cycloalkenyl group；
A represents C or N；
X represents O, S or Se；
N each independently represents 1,2 or 3.
Preferably, the structural formula for the compound of Formulas I structural formula specifically as indicated by ii and iii, but be not limited only to
Lower institute's array structure：
Wherein,
R1、R2、R3、R4、R5, X and n respectively with R in Formulas I1、R2、R3、R4、R5, X and n it is identical.
It is further preferred that structural formula specific as follows Formula II -01~II-54 institute of the structural formula for the compound of Formula II
Show structure, but be not limited only to structure set forth below：
It is further preferred that structural formula specific as follows formula III -01~III- of the structural formula for the compound of formula III
Structure shown in 51, but it is not limited only to structure set forth below：
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device includes substrate, set on base
Anode layer on plate, the hole transmission layer on anode layer, the organic luminous layer on hole transmission layer, set on organic hair
Electron transfer layer on photosphere, the cathode layer on electron transfer layer；Wherein, the material of the organic luminous layer includes above-mentioned
It is one or more in metal complex.
Preferably, it is additionally provided with hole injection layer between the organic electroluminescence device Anodic layer and hole transmission layer.
Wherein, substrate can be glass or flexible substrate, and flexible substrate is using in polyesters, polyimide compound
A kind of material；
Preferably, anode layer can use inorganic material or organic conductive polymer, and inorganic material is tin indium oxide (abbreviation
ITO), the higher metal of the power functions such as the metal oxides such as zinc oxide, zinc tin oxide or gold, silver, copper, the selected as of optimization
ITO, organic conductive polymer are preferably polythiophene/polyvinylbenzenesulfonic acid sodium (PEDOT:PSS a kind of), material in polyaniline
Material；
Preferably, cathode layer generally using the relatively low metal of power functions such as lithium, magnesium, silver, calcium, strontium, aluminium, indium or they with
The electrode layer that copper, the alloy of gold, silver or metal are alternatively formed with metal fluoride, the present invention are preferably magnesium/ag alloy layer；
Preferably, tri-arylamine group material, preferably NPB or DNTPD can be used in hole transmission layer and hole injection layer, knot
Structure formula is as follows：
Preferably, electron transfer layer is generally metal organic complex, preferably Alq3, Liq, BPhen etc., and structural formula is as follows
It is shown：
Preferably, small molecule material generally can be used in organic luminous layer, can be with doping fluorescent material or phosphorescent coloring, this hair
Include metal complex proposed by the present invention in the material of bright organic luminous layer, which can mix as phosphorescence
Miscellaneous material shines in corresponding material of main part, and preferred material of main part is one or more in following compound：
Preferably, the preparation method of the organic electroluminescence device includes the following steps：
1) using cleaning agent, deionized water and organic solvent point a few glass substrates of the step cleaning with ITO；
2) hole injection layer of material of the present invention is included by the method for vacuum evaporation vapor deposition；
3) hole transmission layer of device is deposited by the method for vacuum evaporation；
4) it is further continued for the luminescent layer that vapor deposition includes material of the present invention；
5) continue the electron transfer layer that vapor deposition includes material of the present invention；
6) again by being deposited or sputtering or the method for spin coating prepares metallic cathode.
Preferably, the thickness of the hole injection layer is 30-50nm, and further preferred hole injection layer thickness is 40nm,
Preferably, the thickness of the hole transmission layer is 5-15nm, and further preferred thickness of hole transport layer is 10nm.
Preferably, the thickness of the organic luminous layer is 10-100nm, and further preferred organic light emission layer thickness is 50nm.
Preferably, the thickness of the electron transfer layer is 10-30nm, and further preferred electron-transport layer thickness is 20nm.
Preferably, the thickness of the cathode layer is 90-110nm, and further preferred cathode electrode layer thickness is 100nm.
The present invention also provides a kind of electroluminescent organic material, the raw material of the electroluminescent organic material includes above-mentioned gold
It is one or more in metal complex.
The present invention also provides application of the above-mentioned metal complex in organic electroluminescence device is prepared.
The present invention also provides application of the above-mentioned metal complex in electroluminescent organic material is prepared.
The metal complex of the present invention is separately as luminescent material or as the material of main part in luminescent layer or doping material
The application of material is also in protection domain.
Unless otherwise specified, the present invention in it is raw materials used can by commercially available commercially available, the present invention recorded in it is any
Any number that range is included between any numerical value and end value or end value between end value and end value is formed arbitrary
Subrange.
Beneficial effects of the present invention are as follows：
Metal iridium complex proposed by the present invention is electroluminescent for a series of pyridine metal complexs with benzheterocycle structure
Phosphorescent light-emitting materials are using the benzofuran by modification or benzothiophene as raw material, by being repaiied with substituted 2- pyridyl groups
Adorn a series of phosphor materials being prepared；Metal complex electroluminescent of the present invention is green to red, and shine effect
Rate is high, while the thermal stability of material is good, and material is easily prepared, easy sublimation purification, has boundless market prospects.
Description of the drawings
Fig. 1 is the OLED device structure diagram in the embodiment of the present invention 10.
Specific embodiment
In order to illustrate more clearly of the present invention, the present invention is done further with reference to preferred embodiments and drawings
It is bright.It will be appreciated by those skilled in the art that specifically described content is illustrative and be not restrictive below, it should not be with this
It limits the scope of the invention.
The specific embodiment of the present invention is described in further detail below in conjunction with the accompanying drawings.
Fig. 1 is the OLED device structure diagram in the embodiment of the present invention 10.Wherein, 1- substrates, 2- anode layers, 3- holes
Implanted layer, 4- hole transmission layers, 5 organic luminous layers, 6- electron transfer layers, 7- cathode layers.
In the present invention, preparation method is then conventional method unless otherwise specified.Raw material used is equal unless otherwise instructed
It can be obtained from disclosed commercial sources, the percentage is mass percent unless otherwise specified.A system provided by the invention
Row novel metal complex, all reactions were carried out under the conditions of well-known be suitble to, some are related to simply having
Prepared by machine, such as the preparation of phenyl boronic acid derivative can be synthesized by skilled operative skill, not retouched in detail in the present invention
It states.
The synthetic route of the shown compound Formula II compound of structural formula I of the present invention is as follows, those skilled in the art
It should be understood that similar route can be used for the synthesis of other compounds.
The synthetic route of the shown compound formula III compound of structural formula I of the present invention is as follows, those skilled in the art
It should be understood that similar route can be used for the synthesis of other compounds.
Above-mentioned reaction route citing gives the synthetic route of compound structure general formula I, is prepared for key intermediate Int-
1st, Int-2, Int-3 compound.Wherein R1、R2、R3、R4、R5, X and n it is identical with aforementioned definitions；
Following abbreviation has been used in embodiments of the present invention：
Table 1 is abridged and full name
| Abbreviation | Full name |
| THF | Tetrahydrofuran |
| n-BuLi | Positive group lithium |
| DCM | Dichloromethane |
| (PinB)2 | Connection boric acid pinacol ester |
| Pd(PPh3)4 | Tetrakis triphenylphosphine palladium |
| DAST | Diethylin sulfur trifluoride |
Embodiment 1
The preparation of compound II-05, structural formula are as follows：
The preparation method of above compound II-05, includes the following steps：
The first step：The preparation of the bromo- Benzaldehyde,2-hydroxies of compound 3-
The anhydrous magnesium chloride of 14.5g is dispersed in 250ml anhydrous tetrahydro furans, adds in the paraformaldehyde and 21ml of 7.5g
Triethylamine after being stirred to react 30 minutes, adds in the o-bromophenol of 17.5g, and after adding, stirring temperature rising reflux reacts 16 hours, cold
But room temperature is arrived, 500ml dilute hydrochloric acid is added in, is extracted with ethyl acetate, organic phase is dried with anhydrous sodium sulfate, is filtered, and is concentrated under reduced pressure
It is dry, with silica gel column separating purification, obtain the yellow oil of 30g.
Second step：The preparation of the bromo- 2- nitrobenzofurans of compound 7-
The acetone solution of grease 20g 250ml that the first step obtains is taken, under nitrogen protection, adds in 28g Carbon Dioxides
Potassium is cooled to 10 DEG C with ice-water bath, adds in 28g bromonitromethanes, and insulated and stirred is reacted 2 hours, filtering, filtrate decompression concentration
It is dry, the concentrated hydrochloric acid of 10ml and the methanol of 200ml are added in, temperature rising reflux reacts 30 minutes, is cooled to room temperature, filters, filter cake first
Alcohol is washed, and obtains the yellow solid of 18.5g.
Third walks：The preparation of the bromo- 2- aminobenzofurs of compound 7-
Take the ethyl alcohol of the bromo- 2- nitrobenzofurans 100ml of product 7- of the second step of 18g and the tetrahydrofuran of 100ml
Dissolving, adds in the water of 10ml and the ammonium chloride of 36g, and the lower iron powder for adding in 20g is stirred at room temperature, is stirred to react 16 hours, filters, filter
Dry, residue usable acid alkali purification is concentrated under reduced pressure in liquid, obtains the yellow solid of 11g.
4th step：The preparation of compound Int.-1
The glacial acetic acid of 600ml and the water of 20ml are added in into reaction bulb, reflux is warming up to, is slowly added dropwise under stirring into 10g
The bromo- 2- aminobenzofurs of 7- and 18.2g trifluoroacetylacetone (TFA) be dissolved in 100ml drying DMF solution, drip off after, return
Stream reacts 3 hours, is cooled to room temperature, is concentrated under reduced pressure and does, with silica gel column separating purification, obtains the Int-1 of 13g, white solid.
5th step：The preparation of compound Int-2
The triisopropyl borate ester of 10.0g compounds Int-1 and 8.5g, the tetrahydrochysene furan of 200ml dryings that 4th step is obtained
It mutters mixing, under nitrogen protection, with liquid nitrogen cooling to -78 DEG C, the 2.5M n-BuLis-hexane being slowly added dropwise into 14.5ml is molten
Liquid, insulation reaction 1 hour are raised to and reaction 30 minutes are stirred at room temperature, and the dilute hydrochloric acid for being added dropwise to 100ml is stirred to react 30 minutes, point
Go out organic phase, water phase is extracted with ethyl acetate, and organic phase drying, filtering, filtrate decompression concentration is dry, residue petroleum ether point
It dissipates, filtering, obtains the Int-2 of 7.3g, white solid.
6th step：The preparation of compound Int-3
The 2- bromopyridines of 5.5g intermediate compound Is nt-2 and 4.4g that 5th step is obtained, the natrium carbonicum calcinatum of 8.0g, 50ml first
The water mixing of the ethyl alcohol and 20ml of benzene and 20ml adds the catalyst Pd (PPh3) 4 of 40mg, under nitrogen protection, heating
Back flow reaction 12 hours, is cooled to room temperature, separates organic phase, and water phase is extracted with ethyl acetate, organic phase drying, filtering, filtrate
Dry, residue silica gel column separating purification is concentrated under reduced pressure, obtains the Int-3 of 5.0g, yellow solid.
7th step：The preparation of compound II-05
The iridium chelate SM-10 of the 6th step the compound Int-3 and 3.6g of 5.0g be dispersed in 120ml ethylene glycol ethyl ether and
In 120ml dryings DMF, under nitrogen protection, it is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, be concentrated under reduced pressure and remove
Solvent, silica gel column separating purification obtain the compound II-05 of 2.7g, yellow solid, TOF-MS：M/z (%)=829.1676 [M++
1], confirm that compound II-05 is correct.
Embodiment 2
The preparation of compound II-23, structural formula are as follows：
The preparation of above compound II-23 prepares intermediate with reference to the preparation method of the first step to the 6th step in embodiment 1
Int.-4, the preparation method of other compounds include the following steps：
The first step：The preparation of compound Int.-5
The intermediate compound I nt.-4 of 6.0g is scattered in the deuterated ethyl alcohol of 150ml, adds in the sodium ethoxide solid of 2.5g, and stirring rises
Warm back flow reaction 3 days is cooled to room temperature, is concentrated under reduced pressure and does, adds in the ice water of 150ml and the ethyl acetate of 150ml, separate organic
Phase, water phase are extracted with ethyl acetate, dry, filtering, and filtrate decompression concentration is dry, and silica gel column separating purification, the white for obtaining 5.0g is consolidated
Body.
Second step：The preparation of compound II-23
The iridium chelate SM-10 of the first step compound Int.-5 and 3.4g of 5.0g are dispersed in the ethylene glycol ethyl ether of 120ml
It is dried in DMF with 120ml, under nitrogen protection, is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, reduced pressure removes
Remove solvent, silica gel column separating purification obtains the compound II-23 of 2.0g, yellow solid, TOF-MS：M/z (%)=841.3182 [M++ 1], confirm that compound II-23 is correct.
Embodiment 3
The preparation of compound II-26, structural formula are as follows：
The preparation of above compound II-26 prepares intermediate with reference to the preparation method of the first step to the 6th step in embodiment 1
Int.-6, the preparation method of other compounds include the following steps：
The first step：The preparation of compound Int.-7
The intermediate compound I nt.-6 of 10.0g is scattered in the deuterated ethyl alcohol of 150ml, adds in the sodium ethoxide solid of 3.5g, stirring
Temperature rising reflux reacts 5 days, is cooled to room temperature, is concentrated under reduced pressure and does, adds in the ice water of 150ml and the ethyl acetate of 150ml, separated
Machine phase, water phase are extracted with ethyl acetate, dry, filtering, and filtrate decompression concentration is dry, silica gel column separating purification, obtain the white of 7.5g
Solid.
Second step：The preparation of compound II-26
The iridium chelate SM-10 of the first step compound Int.-7 and 2.7g of 5.0g are dispersed in the ethylene glycol ethyl ether of 120ml
It is dried in DMF with 120ml, under nitrogen protection, is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, reduced pressure removes
Remove solvent, silica gel column separating purification obtains the compound II-26 of 2.4g, yellow solid, TOF-MS：M/z (%)=933.4588 [M++ 1], confirm that compound II-26 is correct.
Embodiment 4
The preparation of compound II-51, structural formula are as follows：
The preparation method of above compound II-51, includes the following steps：
The first step：The preparation of compound Int.-8
The glacial acetic acid of 300ml and the water of 10ml are added in into reaction bulb, reflux is warming up to, is slowly added dropwise under stirring into 5.0g
The bromo- 2- aminobenzofurs of 7- and 11.0g 2- tetrahydrofuran formyl acetones be dissolved in 50ml drying DMF solution, drip off
Afterwards, back flow reaction 3 hours, be cooled to room temperature, be concentrated under reduced pressure dry, with silica gel column separating purification, obtain the Int.-8 of 7.5g, white
Solid.
Second step：The preparation of compound Int.-9
The 7.0g compounds Int.-8 that the first step obtains is dissolved in the tetrahydrofuran of 120ml dryings, is protected in nitrogen
Under, with liquid nitrogen cooling to -78 DEG C, 2.5M n-BuLis-hexane solution into 10ml, insulation reaction 30 minutes, drop is slowly added dropwise
The triisopropyl borate ester of 6.0g is added in, is raised to be stirred at room temperature and react 1 hour, the dilute hydrochloric acid for being added dropwise to 100ml is stirred to react 30 points
Clock separates organic phase, and water phase is extracted with ethyl acetate, and organic phase drying, filtering, filtrate decompression concentration is dry, residue oil
Ether disperses, filtering, obtains the Int.-9 of 4.5g, white solid.
Third walks：The preparation of compound Int.-10
The preparation method of compound Int.-10 please refers to the 6th step of embodiment 1, by the intermediate of the 6th step of embodiment 1
Int.-2 replaces with the product Int.-9 of second step in the present embodiment, and Formula Int.-10, white solid is prepared.
4th step：The preparation of compound II-51
The iridium chelate SM-10 of third step the compound Int.-10 and 3.6g of 5.0g are dispersed in the ethylene glycol ethyl ether of 120ml
It is dried in DMF with 120ml, under nitrogen protection, is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, reduced pressure removes
Remove solvent, silica gel column separating purification obtains the compound II-51 of 3.5g, yellow solid, TOF-MS：M/z (%)=831.2217 [M++ 1], confirm that compound II-51 is correct.
Embodiment 5
The preparation of compound II-52, structural formula are as follows：
The preparation of above compound II-52 prepares intermediate with reference to the preparation method that the first step in embodiment 4 is walked to third
Int.-10, the preparation method of other compounds include the following steps：
The first step：The preparation of compound Int.-11
The intermediate compound I nt.-10 of 10.0g is scattered in the deuterated ethyl alcohol of 150ml and the deuterated tetrahydrofuran of 10ml, is added in
The sodium ethoxide solid of 4.5g, stirring temperature rising reflux react 5 days, are cooled to room temperature, be concentrated under reduced pressure it is dry, add in 150ml ice water and
The ethyl acetate of 150ml separates organic phase, and water phase is extracted with ethyl acetate, dry, filtering, and filtrate decompression concentration is dry, silicagel column
It isolates and purifies, obtains the white solid of 9.5g.
Second step：The preparation of compound II-52
The iridium chelate SM-10 of the first step compound Int.-11 and 3.5g of 5.0g are dispersed in the ethylene glycol ethyl ether of 120ml
It is dried in DMF with 120ml, under nitrogen protection, is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, reduced pressure removes
Remove solvent, silica gel column separating purification obtains the compound II-52 of 3.0g, yellow solid, TOF-MS：M/z (%)=840.2845 [M+], confirm that compound II-52 is correct.
Embodiment 6
The preparation of compound III-01, structural formula are as follows：
The preparation method of above compound III-01, includes the following steps：
The first step：The preparation of compound Int.-12
10.0g compound SM-20 (reference literature Chemistry-A European Journal, 2016,22 (30),
It is prepared by the method for P10415) it is scattered in the ethyl alcohol of 250ml, the ethenylamidine hydrochloride of 4.5g and the potassium hydroxide of 10.0g are added in, is stirred
Temperature rising reflux reacts 2 hours, is cooled to room temperature, is concentrated under reduced pressure and does, and adds in the ice water of 150ml, filtering, and filter cake is washed with water, dry,
With silica gel column separating purification, the yellow solid of 7.3g is obtained.
Second step：The preparation of compound Int.-13
The preparation method of compound Int.-13 please refers to the second step of embodiment 4, by the intermediate of 4 second step of embodiment
Int.-8 replaces with the product Int.-12 of the first step in the present embodiment, and Formula Int.-13, white solid is prepared.
Third walks：The preparation of compound Int.-14
The preparation method of compound Int.-14 please refers to the third step of embodiment 4, the intermediate that 4 third of embodiment is walked
Int.-9 replaces with the product Int.-13 of second step in the present embodiment, and Formula Int.-14, yellow solid is prepared.
4th step：The preparation of compound III-01
The iridium chelate SM-10 of third step the compound Int.-14 and 4.3g of 5.0g are dispersed in the ethylene glycol ethyl ether of 120ml
It is dried in DMF with 120ml, under nitrogen protection, is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, reduced pressure removes
Remove solvent, silica gel column separating purification obtains the compound III-01 of 3.7g, yellow solid, TOF-MS：M/z (%)=776.1918
[M++ 1], confirm that compound III-01 is correct.
Embodiment 7
The preparation of compound III-18, structural formula are as follows：
The first step：The preparation of compound Int.-15
10.0g compound SM-30 (reference literature Chemistry-A European Journal, 2016,22 (30),
It is prepared by the method for P10415) it is scattered in the ethyl alcohol of 250ml, add in the hydrochloric acid isopropyl carbonamidine of 4.9g and the hydroxide of 8.8g
Potassium, stirring temperature rising reflux react 2 hours, are cooled to room temperature, are concentrated under reduced pressure and do, and add in the ice water of 150ml, filtering, filter cake water
It washes, it is dry, with silica gel column separating purification, obtain the yellow solid of 8.2g.
Second step：The preparation of compound Int.-16
The preparation method of compound Int.-16 please refers to the second step of embodiment 4, by the intermediate of 4 second step of embodiment
Int.-8 replaces with the product Int.-15 of the first step in the present embodiment, and Formula Int.-16, yellow solid is prepared.
Third walks：The preparation of compound Int.-17
The preparation method of compound Int.-17 please refers to the third step of embodiment 4, the intermediate that 4 third of embodiment is walked
Int.-9 replaces with the product Int.-16 of second step in the present embodiment, and Formula Int.-17, yellow solid is prepared.
4th step：The preparation of compound III-18
The iridium chelate SM-10 of third step the compound Int.-16 and 3.3g of 5.0g are dispersed in the ethylene glycol ethyl ether of 120ml
It is dried in DMF with 120ml, under nitrogen protection, is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, reduced pressure removes
Remove solvent, silica gel column separating purification obtains the compound III-18 of 2.5g, yellow solid, TOF-MS：M/z (%)=858.2692
[M++ 1], confirm that compound III-18 is correct.
Embodiment 8
The preparation of compound III-12, structural formula are as follows：
The preparation method of above compound III-12, includes the following steps：
The first step：The preparation of compound Int-18
The urea element mixing of the compound SM-20 and 100g of 10.0g, stirring, which is warming up to, is refluxed reaction 2 hours, is cooled to
100 DEG C, 10% sodium hydrate aqueous solution is added dropwise to, is stirred to room temperature, then be added dropwise to dilute hydrochloric acid neutralization, filtered, wash, do
It is dry, with ethyl alcohol recrystallization, obtain the compound Int-18 of 8.2g, white solid.
Second step：The preparation of compound Int-19
The DAST mixing of the compound Int-18 and 48ml of 8.0g, under nitrogen protection, are warming up to 40 DEG C and are stirred to react 24
Hour, room temperature is cooled to, is concentrated under reduced pressure and does, adds in the ice water of 100ml, filtering, filter cake is washed with water, and is dried in vacuo, uses silicagel column
It isolates and purifies, obtains the compound Int-19 of 7.6g, yellow solid.
Third walks：The preparation of compound Int.-20
The preparation method of compound Int.-20 please refers to the 5th step of embodiment 1, by the intermediate of the 5th step of embodiment 1
Int.-1 replaces with the product Int.-19 of second step in the present embodiment, and Formula Int.-20, yellow solid is prepared.
4th step：The preparation of compound Int.-21
The preparation method of compound Int.-21 please refers to the third step of embodiment 4, the intermediate that 4 third of embodiment is walked
Int.-9 replaces with the product Int.-20 that third walks in the present embodiment, and Formula Int.-21, yellow solid is prepared.
5th step：The preparation of compound III-12
The iridium chelate SM-10 of the 4th step the compound Int.-21 and 4.2g of 5.0g is dispersed in the ethylene glycol ethyl ether of 120ml
It is dried in DMF with 120ml, under nitrogen protection, is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, reduced pressure removes
Remove solvent, silica gel column separating purification obtains the compound III-12 of 3.3g, yellow solid, TOF-MS：M/z (%)=780.1665
[M++ 1], confirm that compound III-12 is correct.
Embodiment 9
The preparation of compound III-39, structural formula are as follows：
The preparation of above compound III-39, the preparation method walked with reference to the first step to third in embodiment 6 prepare intermediate
Body Int.-22, the preparation method of other compounds include the following steps：
The first step：The preparation of compound Int.-23
The intermediate compound I nt.-22 of 10.0g is scattered in the deuterated ethyl alcohol of 150ml, adds in the sodium ethoxide solid of 4.0g, stirring
Temperature rising reflux reacts 5 days, is cooled to room temperature, is concentrated under reduced pressure and does, adds in the ice water of 150ml and the ethyl acetate of 150ml, separated
Machine phase, water phase are extracted with ethyl acetate, dry, filtering, and filtrate decompression concentration is dry, silica gel column separating purification, obtain the yellow of 10.0g
Solid.
Second step：The preparation of compound III-39
The iridium chelate SM-10 of the first step compound Int.-23 and 3.3g of 5.0g are dispersed in the ethylene glycol ethyl ether of 120ml
It is dried in DMF with 120ml, under nitrogen protection, is warming up to 135 DEG C and is stirred to react 24 hours, be cooled to room temperature, reduced pressure removes
Remove solvent, silica gel column separating purification obtains the compound III-39 of 2.1g, yellow solid, TOF-MS：M/z (%)=858.3406
[M++ 1], confirm that compound III-39 is correct.
Embodiment 10
A kind of OLED device, as shown in Figure 1, anode layer 2 including substrate 1, on substrate 1, on anode layer 2
Hole injection layer 3, the organic luminous layer 5 on hole transmission layer 4, is set the hole transmission layer 4 on hole injection layer 3
In the electron transfer layer 6 on organic luminous layer 5, the cathode layer 7 on electron transfer layer 6.
The preparation method of above-mentioned OLED device includes the following steps：
1) glass substrate for being coated with ITO conductive layer in cleaning agent is ultrasonically treated 30 minutes, rushed in deionized water
It washes, it is 30 minutes ultrasonic in acetone/ethanol in the mixed solvent, it is baked to is completely dried under a clean environment, use ultraviolet rays cleaning
Machine irradiates 10 minutes, and with low energy cation beam bombarded surface.
2) the above-mentioned ito glass substrate handled well is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa,
Continue to be deposited compound DNTPD on above-mentioned anode tunic respectively as hole injection layer, evaporation rate 0.1nm/s, evaporation film
Thickness is 40nm；Continue to be deposited NPB on above-mentioned hole injection layer film as hole transmission layer, evaporation rate 0.1nm/s, evaporation film
Thickness is 10nm；
3) continue that the luminescent layer of one layer of the compound of the present invention Formulas I and mCBP as device is deposited on the hole transport layer,
Wherein, material and the compound of the present invention Formulas I are dopant material based on mCP, and the evaporation rate ratio of Formula I and mCBP are
1：The doping concentration of 100, Formula I in mCBP is 1%, and total rate is deposited as 0.1nm/s, and vapor deposition film thickness is 50nm；
4) electron transfer layer of the one layer of Liq material of vapor deposition as device is further continued in above-mentioned hole, plating rate is 0.1nm/
S, vapor deposition film thickness are 20nm；Finally, cathode of the magnesium/ag alloy layer as device is deposited successively on above-mentioned electron transfer layer
Layer, the wherein evaporation rate of magnesium/ag alloy layer are 2.0~3.0nm/s, and vapor deposition film thickness is 100nm；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound II-05, obtains this hair
The OLED-1 of bright offer；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound II-23, obtains this hair
The OLED-2 of bright offer；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound II-26, obtains this hair
The OLED-3 of bright offer；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound II-51, obtains this hair
The OLED-4 of bright offer；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound II-52, obtains this hair
The OLED-5 of bright offer；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound III-01, obtains this hair
The OLED-6 of bright offer；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound III-12, obtains this hair
The OLED-7 of bright offer；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound III-18, obtains this hair
The OLED-8 of bright offer；
According to upper identical step, step 3) compound used therefor Formulas I is only replaced with into compound III-39, obtains this hair
The OLED-9 of bright offer；
The performance test results of obtained device OLED-1 to OLED-9 are as shown in table 2：
2 performance test results of table
Conclusion：It is analyzed from the performance test results, metal iridium complex green light of the invention, excitation purity is preferable, and coloration is sat
Green wavelength is marked on, performance has been more than existing known green light material, and under conditions of test device is unencapsulated, device
Luminescent lifetime it is also ideal.
Obviously, the above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be pair
The restriction of embodiments of the present invention for those of ordinary skill in the art, may be used also on the basis of the above description
To make other variations or changes in different ways, all embodiments can not be exhaustive here, it is every to belong to this hair
The obvious changes or variations that bright technical solution is extended out are still in the row of protection scope of the present invention.
Claims (10)
1. a kind of metal iridium complex, which is characterized in that the metal iridium complex is compound shown in Formulas I
Wherein：
R1And R2Alkyl, the deuterium of C1-C10 that the alkyl of C1-C10, the cycloalkyl of C4-C10, deuterium replace is each independently represented to take
The cycloalkyl of the C4-C10 in generation, the alkoxy of C1-C8, the alkoxy of C1-C8 of deuterium substitution, the alkylthio group of C1-C8, deuterium replace
Alkylthio group, fluorine or the cyano of C1-C8；
R3、R4、R5Each independently represent the alkane of hydrogen, deuterium hydrogen, fluorine, the alkyl of C1-C8, the alkyl of C1-C8 that deuterium replaces, C1-C8
Oxygroup, the alkoxy of C1-C8, the silylation of C1-C8, the substituted or unsubstituted C of deuterium substitution6-C20Aryl, substitution or not
Substituted C6-C20Aryloxy group, substituted or unsubstituted C6-C20Arylthio, fluorine or cyano；
The substituted C6-C20Aryl, the C of substitution6-C20Aryloxy group and the C of substitution6-C20Substituent group described in arylthio is each
From independently selected from hydrogen, deuterium hydrogen, halogen atom, hydroxyl, cyano, C1-C20Alkyl, C2-C20Alkenyl, C2-C20Alkynyl, C1-C20Alcoxyl
Base, C3-C20Cycloalkyl group or C3-C20It is one or more in cycloalkenyl group；
A represents C or N；
X represents O, S or Se；
N each independently represents 1,2 or 3.
2. metal iridium complex according to claim 1, which is characterized in that compound described in the Formulas I be with Formula Il-
Compound shown in 01~II-45, formula III -01~III-51
3. a kind of organic electroluminescence device, successively including substrate, anode layer, hole transmission layer, organic luminous layer, electron-transport
Layer and cathode layer, which is characterized in that the material of the organic luminous layer includes the gold described in one or more claims 1 or 2
Belong to complex of iridium.
4. organic electroluminescence device according to claim 3, which is characterized in that the anode layer and the hole transport
Hole injection layer is additionally provided between layer.
5. organic electroluminescence device according to claim 4, which is characterized in that the thickness of the hole injection layer is
30-50nm。
6. organic electroluminescence device according to claim 4, which is characterized in that the thickness of the hole injection layer is
40nm。
7. organic electroluminescence device according to claim 3, which is characterized in that the thickness of the hole transmission layer is 5-
15nm；The thickness of the organic luminous layer is 10-100nm；The thickness of the electron transfer layer is 10-30nm；The cathode layer
Thickness be 90-110nm.
8. organic electroluminescence device according to claim 3, which is characterized in that the thickness of the hole transmission layer is
10nm；The thickness of the organic luminous layer is 50nm；The thickness of the electron transfer layer is 20nm；The thickness of the cathode layer is
100nm。
9. a kind of electroluminescent organic material, which is characterized in that the raw material of the electroluminescent organic material includes claim 1
It is or one or more in the metal iridium complex described in 2.
10. metal iridium complex is in organic electroluminescence device or electroluminescent organic material is prepared described in claims 1 or 2
Application.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019154159A1 (en) * | 2018-02-09 | 2019-08-15 | 石家庄诚志永华显示材料有限公司 | Metal iridium complex and organic electroluminescent device containing metal iridium complex |
| EP3623443A1 (en) * | 2018-09-15 | 2020-03-18 | Beijing Summer Sprout Technology Co., Ltd. | Metal complex with fluorine substitution |
| CN111484839A (en) * | 2019-11-01 | 2020-08-04 | 吉林奥来德光电材料股份有限公司 | Organic light-emitting compound, preparation method thereof and organic electroluminescent device |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20220043755A (en) * | 2020-09-29 | 2022-04-05 | 삼성전자주식회사 | Organometallic compound, organic light emitting device including the same and electronic apparatus including the organic light emitting device |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105367606A (en) * | 2014-08-07 | 2016-03-02 | 环球展览公司 | Organic electroluminescent materials and devices |
| US20160093815A1 (en) * | 2014-09-29 | 2016-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN105801628A (en) * | 2015-01-15 | 2016-07-27 | 环球展览公司 | Organic light emitting material |
| US20170069848A1 (en) * | 2015-09-09 | 2017-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11108000B2 (en) * | 2014-08-07 | 2021-08-31 | Unniversal Display Corporation | Organic electroluminescent materials and devices |
| CN108164564A (en) * | 2018-02-09 | 2018-06-15 | 石家庄诚志永华显示材料有限公司 | A kind of metal iridium complex and the organic electroluminescence device comprising the metal iridium complex |
-
2018
- 2018-02-09 CN CN201810134626.XA patent/CN108164564A/en active Pending
-
2019
- 2019-01-28 WO PCT/CN2019/073489 patent/WO2019154159A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105367606A (en) * | 2014-08-07 | 2016-03-02 | 环球展览公司 | Organic electroluminescent materials and devices |
| US20160093815A1 (en) * | 2014-09-29 | 2016-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN105801628A (en) * | 2015-01-15 | 2016-07-27 | 环球展览公司 | Organic light emitting material |
| US20170069848A1 (en) * | 2015-09-09 | 2017-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019154159A1 (en) * | 2018-02-09 | 2019-08-15 | 石家庄诚志永华显示材料有限公司 | Metal iridium complex and organic electroluminescent device containing metal iridium complex |
| KR20210138549A (en) * | 2018-09-15 | 2021-11-19 | 베이징 썸머 스프라우트 테크놀로지 컴퍼니 리미티드 | Metal complex with fluorine substitution |
| KR102332160B1 (en) * | 2018-09-15 | 2021-11-29 | 베이징 썸머 스프라우트 테크놀로지 컴퍼니 리미티드 | Metal complex with fluorine substitution |
| JP2021102636A (en) * | 2018-09-15 | 2021-07-15 | 北京夏禾科技有限公司 | Metal complex containing fluorine substitution structure, electroluminescent element containing the metal complex and preparation of compound |
| CN110903321B (en) * | 2018-09-15 | 2023-12-12 | 北京夏禾科技有限公司 | Containing fluorine-substituted metal complexes |
| JP7182311B2 (en) | 2018-09-15 | 2022-12-02 | 北京夏禾科技有限公司 | A metal complex containing a fluorine-substituted structure, an electroluminescent device containing the metal complex, and a formulation of the compound |
| CN110903321A (en) * | 2018-09-15 | 2020-03-24 | 北京夏禾科技有限公司 | Metal complexes containing fluorine substitution |
| EP3623443A1 (en) * | 2018-09-15 | 2020-03-18 | Beijing Summer Sprout Technology Co., Ltd. | Metal complex with fluorine substitution |
| KR102584939B1 (en) * | 2018-09-15 | 2023-10-05 | 베이징 썸머 스프라우트 테크놀로지 컴퍼니 리미티드 | Metal complex with fluorine substitution |
| EP4098716A3 (en) * | 2018-09-15 | 2023-02-15 | Beijing Summer Sprout Technology Co., Ltd. | Metal complex with fluorine substitution |
| KR20200032646A (en) * | 2018-09-15 | 2020-03-26 | 베이징 썸머 스프라우트 테크놀로지 컴퍼니 리미티드 | Metal complex with fluorine substitution |
| JP2020066622A (en) * | 2018-09-15 | 2020-04-30 | 北京夏禾科技有限公司 | Metal complex containing fluorine substituted structure |
| US11731994B2 (en) | 2018-12-05 | 2023-08-22 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound |
| EP3689889A1 (en) * | 2019-02-01 | 2020-08-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11785839B2 (en) | 2019-02-01 | 2023-10-10 | Beijing Summer Sprout Technology Co., Ltd. | Organic light-emitting materials containing cyano-substituted ligand |
| CN111518139A (en) * | 2019-02-01 | 2020-08-11 | 北京夏禾科技有限公司 | Organic luminescent material containing cyano-substituted ligand |
| CN111518140A (en) * | 2019-02-01 | 2020-08-11 | 环球展览公司 | Organic electroluminescent material and device |
| EP4301117A3 (en) * | 2019-02-01 | 2024-03-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN111518139B (en) * | 2019-02-01 | 2023-12-12 | 北京夏禾科技有限公司 | Organic luminescent material containing cyano-substituted ligand |
| US11758803B2 (en) | 2019-03-07 | 2023-09-12 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device |
| CN111484839A (en) * | 2019-11-01 | 2020-08-04 | 吉林奥来德光电材料股份有限公司 | Organic light-emitting compound, preparation method thereof and organic electroluminescent device |
| CN113121603B (en) * | 2019-12-30 | 2023-02-24 | 江苏三月科技股份有限公司 | Phosphorescent iridium complex serving as OLED (organic light emitting diode) doping material and application thereof |
| CN113121603A (en) * | 2019-12-30 | 2021-07-16 | 江苏三月光电科技有限公司 | Phosphorescent iridium complex serving as OLED (organic light emitting diode) doping material and application thereof |
| CN113735911A (en) * | 2020-05-29 | 2021-12-03 | 北京夏禾科技有限公司 | Metal complex, electroluminescent device and application thereof |
| CN113809243B (en) * | 2020-06-13 | 2023-10-03 | 北京夏禾科技有限公司 | Organic electroluminescent device |
| CN113809243A (en) * | 2020-06-13 | 2021-12-17 | 北京夏禾科技有限公司 | Organic electroluminescent device |
| CN113816997A (en) * | 2020-06-20 | 2021-12-21 | 北京夏禾科技有限公司 | Phosphorescent organic metal complex and application thereof |
| US11952390B2 (en) | 2020-06-20 | 2024-04-09 | Beijing Summer Sprout Technology Co., Ltd. | Phosphorescent organic metal complex and use thereof |
| CN113816997B (en) * | 2020-06-20 | 2024-05-28 | 北京夏禾科技有限公司 | Phosphorescent organometallic complex and application thereof |
| CN112724178A (en) * | 2020-12-01 | 2021-04-30 | 浙江华显光电科技有限公司 | Iridium metal compound with deuterium-fluorine synergistic effect and photoelectric element comprising iridium metal compound |
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