CN107915762A - One kind is used as transient metal complex, its preparation method and the application of phosphor material - Google Patents

One kind is used as transient metal complex, its preparation method and the application of phosphor material Download PDF

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Publication number
CN107915762A
CN107915762A CN201711131183.0A CN201711131183A CN107915762A CN 107915762 A CN107915762 A CN 107915762A CN 201711131183 A CN201711131183 A CN 201711131183A CN 107915762 A CN107915762 A CN 107915762A
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substituted
ligand
metal complex
transient metal
carbonyl
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陈跃
丰佩川
张国轩
王鹏程
刘鹏
李伟超
张加运
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Yantai Display Photoelectric Materials Research Institute Co Ltd
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Yantai Display Photoelectric Materials Research Institute Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/006—Palladium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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

Abstract

The invention belongs to organic photoelectrical material technical field, more particularly to a kind of transient metal complex, its preparation method and application for being used as phosphor material.Not only luminous efficiency is high for complex produced by the present invention, but also the wavelength for launching light can be in a wide range of interior adjusting.The main ligand of such complex has identical skeleton structure, by varying position of the hetero atom on main ligand and hetero atom species, so as to fulfill wavelength of transmitted light near infrared range adjusting.In addition, the preparation method of different colours luminescent material is essentially identical, it is easy to operate.

Description

One kind is used as transient metal complex, its preparation method and the application of phosphor material
Technical field
The invention belongs to organic photoelectrical material technical field, more particularly to a kind of transition gold for being used as near-infrared phosphor material Metal complex, its preparation method and application.
Background technology
Near infrared technology is owned by being widely applied prospect in multiple fields such as night vision, biology, medicine, aerospaces.And Organic electroluminescent LED (OLED) has the advantages that flexible foldable, self-luminous, low energy consumption.OLED is applied to near-infrared Field, near infrared technology will possess more wide application prospect.With deep and its application range of near-infrared area research Expansion, particularly optical communication, the development of the industry such as public safety and biologic medical and demand have good there is an urgent need to one kind The near-infrared material of luminescent properties
Organic material is since technique is simple and receives much concern the advantages that structure easy-regulating.Up to the present, near-infrared has Machine luminescent material mainly has two major classes：First, lanthanide complexes；Second, organic ion dyestuff.Due to the f-f of rare earth element Transition is that parity is prohibited, and the excitation of its molecule needs the energy transfer by ligand and central ion, and luminous efficiency is relatively low.And Organic ion dyestuff is due to electrostatic interaction, and molecule easily causes luminous extraction to be gone out because of aggregation, and host-guest system device Also there is material of main part with the problem of infraluminescence and the shortcomings of efficiency is low and preparation process is complicated.And it is organic it is non-from Subtype luminescent material then from the limitation of above-mentioned factor, can obtain higher luminous efficiency.But it is presently available for the near of OLED Infrared organic phosphorescent material is simultaneously few.New near-infrared light-emitting material is developed, the development near infrared technology has important meaning Justice.
At present, the complex with metal iridium, platinum, osmium etc. for metal center may be used as red phosphorescence material, for example use benzene Even quinoline or benzene connect the complex of iridium material that isoquinolin etc. is main ligand, and wherein quinoline and isoquinolin is risen in triplet exciton To the effect of electron acceptor.By increasing the common amount of acceptor, it can make transmitting light that red shift occur, choose suitable organic ligand Transmitting light can be made to be moved near infrared region.
The content of the invention
The present invention is in view of the deficiency of the prior art, there is provided one kind is used as the transition metal of near-infrared phosphor material Complex, its preparation method and application.
The technical solution that the present invention solves above-mentioned technical problem is as follows：One kind is used as the Transition metal complexes of phosphor material Thing, its structural formula are as follows：
Wherein, X1、X2、X3、X4、X5、X6、X7It is independently each N, C or B；
Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11、Y12It is independently each N or CR1, wherein R1For hydrogen, deuterium, substitution Or non substituted alkyl, cycloalkyl, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substitution Or non-substituted heteroaryl, alkoxy, aryloxy group, amido, silylation, halogen, CN, SCN, NO2、CR2R3NR4R5Or CF3It is any It is a kind of；
R2、R3、R4、R5It is independently each hydrogen, deuterium, substituted or non-substituted alkyl, cycloalkyl, hydroxyl, amino, sulfydryl, alkene Base, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkoxy, aryloxy group, amido, silane Base, halogen, CN, SCN, NO2Or CF3Any one；
Z1It is independently O, S, Se, N, NR6Or CR7；R6And R7It is independently each hydrogen, deuterium, substituted or non-substituted alkyl, ring Alkyl, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, Alkoxy, aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one；
M is transition metal Ir, Pd or Pt；
(L^Z) it is assistant ligand, is bidentate ligand, it is identical or different with the main ligand in left side in structure above；
m>0, and m is integer；N >=0, and n is integer.
Further, Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11、Y12、Z1Two groups of arbitrary neighborhood connect to be formed Cyclic group, two groups, which connect the cyclic group to be formed, can include one or more hetero atom.
Further, Y4And Y5Pass through-(Y)x- abutment connection, the Y is O, S, Se, CR8、NR9, carbonyl or AR10R11； X >=1, and be integer；X Y is separate；
Wherein, A C, Si or Ge；R8、R9、R10、R11It is independently each hydrogen, deuterium, substituted or non-substituted alkyl, cycloalkanes Base, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkane Epoxide, aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one.
Further, between main ligand or between main ligand and assistant ligand directly by covalent key connection or by- (W)z- abutment connect into tetradentate ligands or sexadentate ligand；The W is O, S, Se, CR12、NR13、DR14R15, carbonyl, take Generation or non-substituted aromatic radical, substituted or non-substituted heteroaryl or cycloalkyl, z >=1, and be integer；Z W is separate；
Wherein, D C, Si or Ge；R12、R13、R14、R15It is independently each hydrogen, deuterium, substituted or non-substituted alkyl, cycloalkanes Base, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkane Epoxide, aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one.
Further, the assistant ligand (L^Z) is acetylacetone,2,4-pentanedione, 2- pyridine carboxylic acids, 2- phenylpyridines, 2,2,6,6- tetra- Methyl -3,5- pimelic acid, (E)-N, N'- diisopropyl benzenecarboximidamide, (Z) -2,3- diisopropyl -1,1- diphenylguanidines or 2,8- bis- Any one in methyl -4,6- nonyl diketone.
Preferably, above-mentioned transient metal complex, its structural formula are respectively：
Second object of the present invention is the preparation method for providing above-mentioned transient metal complex, and step is as follows：
(1) under nitrogen protection, main ligand is dissolved in ethylene glycol monoethyl ether, adds hydrated iridium trichloride and deionization Water, heating reaction obtain iridium chlorine bridge complex；
(2) in alkaline conditions, by iridium chlorine bridge complex and assistant ligand (L^Z) heating reflux reaction, transition gold is obtained Metal complex；
The assistant ligand (L^Z) is bidentate ligand, it is identical with the main ligand in left side in structure above, Huo Zhewei Acetylacetone,2,4-pentanedione, 2- pyridine carboxylic acids, 2- phenylpyridines, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'- diisopropyl benzenes Any one in carbonamidine, (Z) -2,3- diisopropyl -1,1- diphenylguanidines, 2,8- dimethyl -4,6- nonyl diketone.
Third object of the present invention is to provide above-mentioned transient metal complex as electroluminescent material, in Organic Electricity Application in electroluminescence device.
The beneficial effects of the invention are as follows：Not only luminous efficiency is high for complex produced by the present invention, but also launches the wavelength of light Can be in a wide range of interior adjusting.The main ligand of such complex has identical skeleton structure, by varying hetero atom in main ligand On position and hetero atom species, so as to fulfill wavelength of transmitted light near infrared range adjusting.In addition, different colours shine The preparation method of material is essentially identical, easy to operate.
Brief description of the drawings
Fig. 1 is the OLED structure schematic diagram of electroluminescent organic material；
Fig. 2 is the emission spectroanalysis figure of application examples 1-3；
In figure, 1, glass substrate；2nd, anode layer；3rd, hole injection layer；4th, hole transmission layer；5th, luminescent layer；6th, electronics passes Defeated layer；7th, electron injecting layer；8th, cathode layer.
Embodiment
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit Determine the scope of the present invention.
Embodiment 1
The synthesis of complex of iridium Ir8, reaction equation are as follows：
(1) chlorine bridge dimer is synthesized
(2) object synthesizes
Embodiment 2
The synthesis of complex of iridium Ir14, reaction equation are as follows：
(1) chlorine bridge dimer is synthesized
(2) object synthesizes
Embodiment 3
The synthesis of complex of iridium Ir9, reaction equation are as follows：(1) chlorine bridge dimer is synthesized
(2) object synthesizes
As shown in Figure 1, the structure of organic electroluminescence device (OLED) includes stacking gradually the glass substrate 1 of combination, sun Pole layer 2, hole injection layer 3, hole transmission layer 4, luminescent layer 5, electron transfer layer 6, electron injecting layer 7 and cathode layer 8.This is sent out Bright obtained iridium phosphor material is applied in the luminescent layer of OLED, each composition of layer compositions of the OLED that table 1 is application examples 1-3.
Table 1
Application examples 1
The tin indium oxide (ITO) that a layer thickness is 100nm is deposited on glass end liner 1 and is used as transparent anode layer 2；Transparent On anode layer 2 vacuum evaporation thickness be 10nm NPB (N, N '-two (1- naphthyls)-N, N '-diphenyl -1,1 '-biphenyl -4-4 ' - Diamines) hole mobile material as hole injection layer 3, wherein doping mass ratio 3% F4-TCNQ (2,3,5,6- tetra- fluoro- 7, Tetra- cyanogen dimethyl-parabenzoquinone of 7', 8,8'-)；Be on hole injection layer 3 a layer thickness be 100nm spiro-TAD (2,2', 7, (the diphenyl amino) -9,9'- of 7'- tetra- spiro-bisfluorenes) it is used as hole transmission layer 4；Vacuum evaporation a layer thickness on hole transmission layer 4 Luminescent layer 5 is used as the Bebq2 (double (10- hydroxy benzos [h] quinoline) berylliums) of 40nm, wherein doped with 6wt% complex of iridium Ir8；The TPQ (2,3,5,8- tetraphenyls quinoxaline) that vacuum evaporation a layer thickness is 30nm successively on luminescent layer 5 again is as electricity Sub- transport layer 6, the Liq that thickness is 1nm are finally deposited as electron injecting layer 7 on electron injecting layer 7 using vacuum evaporation coating Technology deposit thickness is cathode layer 8 of the metallic aluminium (Al) of 100nm as device.
Know through performance test, the maximum luminous wavelength of the electroluminescent spectrum of the device is located at 817nm, maximum current effect Rate is 16cd/A, and maximum external quantum efficiency is 7%.
Application examples 2
It is identical with application examples 1, it is with 1 difference of application examples：Luminescent layer 5 is Bebq2 (double (10- hydroxyls of thickness 40nm Base benzo [h] quinoline) beryllium), wherein doped with 6wt% complex of iridium Ir14.
Know through performance test, the maximum luminous wavelength of the electroluminescent spectrum of the device is located at 1080nm, maximum current Efficiency is 22cd/A, and maximum external quantum efficiency is 11%.
Application examples 3
It is identical with application examples 1, it is with 1 difference of application examples：Luminescent layer 5 is Bebq2 (double (10- hydroxyls of thickness 40nm Base benzo [h] quinoline) beryllium), wherein doped with 6wt% complex of iridium Ir9.
Know through performance test, the maximum luminous wavelength of the electroluminescent spectrum of the device is located at 952nm, maximum current effect Rate is 13cd/A, and maximum external quantum efficiency is 5%.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all the present invention spirit and Within principle, any modification, equivalent replacement, improvement and so on, should all be included in the protection scope of the present invention.

Claims (9)

1. one kind is used as the transient metal complex of phosphor material, it is characterised in that its structural formula is as follows：
Wherein, X1、X2、X3、X4、X5、X6、X7It is independently each N, C or B；
Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11、Y12It is independently each N or CR1, wherein R1For hydrogen, deuterium, substitution or non- Substitute alkyl, cycloalkyl, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substitution or non- Substituted heteroaryl, alkoxy, aryloxy group, amido, silylation, halogen, CN, SCN, NO2、CR2R3NR4R5Or CF3Any one；
R2、R3、R4、R5It is independently each hydrogen, deuterium, substituted or non-substituted alkyl, cycloalkyl, hydroxyl, amino, sulfydryl, alkenyl, alkynes Base, carbonyl, carboxyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkoxy, aryloxy group, amido, silylation, halogen Element, CN, SCN, NO2Or CF3Any one；
Z1For O, S, Se, N, NR6Or CR7；R6And R7Each be independently hydrogen, deuterium, substituted or non-substituted alkyl, cycloalkyl, hydroxyl, Amino, sulfydryl, alkenyl, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkoxy, fragrant oxygen Base, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one；
M is transition metal Ir, Pd or Pt；
(L^Z) it is assistant ligand, is bidentate ligand, it is identical or different with the main ligand in left side in structure above；
m>0, and m is integer；N >=0, and n is integer.
2. transient metal complex according to claim 1, it is characterised in that Y1、Y2、Y3、Y4、Y5、Y6、Y7、Y8、Y9、 Y10、Y11、Y12、Z1Two groups of arbitrary neighborhood connect to form cyclic group.
3. transient metal complex according to claim 2, it is characterised in that two groups of arbitrary neighborhood connect to be formed Cyclic group include one or more hetero atom.
4. transient metal complex according to claim 2, it is characterised in that Y4And Y5Pass through-(Y)x- abutment connection, The Y is O, S, Se, CR8、NR9, carbonyl or AR10R11；X >=1, and be integer；X Y is separate；
Wherein, A C, Si or Ge；R8、R9、R10、R11It is independently each hydrogen, deuterium, substituted or non-substituted alkyl, cycloalkyl, hydroxyl Base, amino, sulfydryl, alkenyl, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkoxy, Aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one.
5. transient metal complex according to claim 1, it is characterised in that between main ligand or main ligand with it is auxiliary Help between ligand directly by covalent key connection or by-(W)z- abutment connect into tetradentate ligands or sexadentate ligand；It is described W be O, S, Se, CR12、NR13、DR14R15, carbonyl, substituted or non-substituted aromatic radical, substituted or non-substituted heteroaryl or cycloalkanes Base, z >=1, and be integer；Z W is separate；
Wherein, D C, Si or Ge；R12、R13、R14、R15It is independently each hydrogen, deuterium, substituted or non-substituted alkyl, cycloalkyl, hydroxyl Base, amino, sulfydryl, alkenyl, alkynyl, carbonyl, carboxyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkoxy, Aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one.
6. transient metal complex according to claim 1, it is characterised in that the assistant ligand (L^Z) is acetyl Acetone, 2- pyridine carboxylic acids, 2- phenylpyridines, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'- diisopropyl benzenecarboximidamide, (Z) any one in -2,3- diisopropyls -1,1- diphenylguanidines or 2,8- dimethyl -4,6- nonyl diketone.
7. transient metal complex according to claim 1, it is characterised in that its structural formula is：
8. the preparation method of transient metal complex described in a kind of claim 1, it is characterised in that step is as follows：
(1) under nitrogen protection, main ligand is dissolved in ethylene glycol monoethyl ether, adds hydrated iridium trichloride and deionized water, add Thermal response obtains iridium chlorine bridge complex；
(2) in alkaline conditions, by iridium chlorine bridge complex and assistant ligand (L^Z) heating reflux reaction, obtain transition metal and match somebody with somebody Compound；
The assistant ligand (L^Z) is bidentate ligand, it is identical with the main ligand in left side in structure above, or is acetyl Acetone, 2- pyridine carboxylic acids, 2- phenylpyridines, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'- diisopropyl benzenecarboximidamide, (Z) any one in -2,3- diisopropyls -1,1- diphenylguanidines, 2,8- dimethyl -4,6- nonyl diketone.
9. a kind of any one of the claim 1-7 transient metal complex is as electroluminescent material, in organic electroluminescent Application in device.
CN201711131183.0A 2017-11-15 2017-11-15 One kind is used as transient metal complex, its preparation method and the application of phosphor material Pending CN107915762A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020065443A1 (en) * 2018-09-27 2020-04-02 株式会社半導体エネルギー研究所 Light-emitting device, light-emitting apparatus, light-emitting module, electronics, lighting apparatus, organometallic complex, light-emitting material, organic compound, and dinuclear complex
EP4001286A1 (en) * 2020-11-24 2022-05-25 Universal Display Corporation Organic electroluminescent materials and devices
CN114989223A (en) * 2022-04-25 2022-09-02 上海八亿时空先进材料有限公司 Metal complex and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1626540A (en) * 2003-08-07 2005-06-15 三星Sdi株式会社 Iridium compound and organic electroluminescent device using the same
CN105524114A (en) * 2015-12-24 2016-04-27 石家庄诚志永华显示材料有限公司 Series of deep blue metal iridium phosphorescence OLED materials

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1626540A (en) * 2003-08-07 2005-06-15 三星Sdi株式会社 Iridium compound and organic electroluminescent device using the same
CN105524114A (en) * 2015-12-24 2016-04-27 石家庄诚志永华显示材料有限公司 Series of deep blue metal iridium phosphorescence OLED materials

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020065443A1 (en) * 2018-09-27 2020-04-02 株式会社半導体エネルギー研究所 Light-emitting device, light-emitting apparatus, light-emitting module, electronics, lighting apparatus, organometallic complex, light-emitting material, organic compound, and dinuclear complex
JPWO2020065443A1 (en) * 2018-09-27 2021-10-21 株式会社半導体エネルギー研究所 Light emitting devices, light emitting devices, light emitting modules, electronic devices, lighting devices, organometallic complexes, light emitting materials, organic compounds, and dinuclear complexes
JP7345487B2 (en) 2018-09-27 2023-09-15 株式会社半導体エネルギー研究所 Organometallic complexes, luminescent materials, luminescent devices, organic compounds and dinuclear complexes
EP4001286A1 (en) * 2020-11-24 2022-05-25 Universal Display Corporation Organic electroluminescent materials and devices
CN114989223A (en) * 2022-04-25 2022-09-02 上海八亿时空先进材料有限公司 Metal complex and application thereof

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Application publication date: 20180417