CN109988193B - Green phosphorescent compound and organic electroluminescent device using the same - Google Patents
Green phosphorescent compound and organic electroluminescent device using the same Download PDFInfo
- Publication number
- CN109988193B CN109988193B CN201910038120.3A CN201910038120A CN109988193B CN 109988193 B CN109988193 B CN 109988193B CN 201910038120 A CN201910038120 A CN 201910038120A CN 109988193 B CN109988193 B CN 109988193B
- Authority
- CN
- China
- Prior art keywords
- electroluminescent device
- organic electroluminescent
- light emitting
- layer
- green phosphorescent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 17
- 238000002347 injection Methods 0.000 claims abstract description 15
- 239000007924 injection Substances 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 12
- 239000002019 doping agent Substances 0.000 claims abstract description 10
- 230000005525 hole transport Effects 0.000 claims abstract description 5
- 239000003446 ligand Substances 0.000 claims description 22
- -1 methylquinolyl Chemical group 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 238000001228 spectrum Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000758 substrate Substances 0.000 description 37
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000539 dimer Substances 0.000 description 20
- 239000011521 glass Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 8
- 229940093475 2-ethoxyethanol Drugs 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910021607 Silver chloride Inorganic materials 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PTBRNAVGPWOGSE-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)pyridine Chemical compound C1=CC(C)=CC=C1C1=CC=C(C)C=N1 PTBRNAVGPWOGSE-UHFFFAOYSA-N 0.000 description 2
- ZYLPQYYLLRBVOK-UHFFFAOYSA-N 5-methyl-2-phenylpyridine Chemical compound N1=CC(C)=CC=C1C1=CC=CC=C1 ZYLPQYYLLRBVOK-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 1
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 1
- GONULLRFSHKLBS-UHFFFAOYSA-N 2-chloro-3-fluoro-4-iodopyridine Chemical compound FC1=C(I)C=CN=C1Cl GONULLRFSHKLBS-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Images
Classifications
-
- 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 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
-
- 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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a green phosphorescent compound and an organic electroluminescent device using the same, in the organic electroluminescent device including an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode deposited in sequence with each other, the organic electroluminescent device may use a compound of the following formula (I) as a dopant of the light emitting layer:
n is 1 or 2; the green phosphorescent material has high efficiency, high color purity and narrow spectrum effect.
Description
Technical Field
The present invention relates to an organic electroluminescent device, and more particularly, to a green phosphorescent compound and an organic electroluminescent device using the same. Most particularly, the present invention relates to a red phosphor used as a dopant of a light emitting layer of an organic electroluminescent device formed by sequentially depositing an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode.
Background
In recent years, as the size of display devices is getting larger, flat display devices occupying less space are more and more required. The flat panel display device includes an organic electroluminescent device, also called an Organic Light Emitting Diode (OLED). The technology of the organic electroluminescent device is developing at a great speed, and many prototypes have been disclosed.
When electric charges are injected into an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), the organic electroluminescent device emits light. More specifically, when an electron and a hole form a pair, light is emitted, and the newly generated electron-hole pair decays. The organic electroluminescent device may be formed on a flexible transparent substrate such as plastic. The organic electroluminescent device may also be driven at a lower voltage (i.e., a voltage less than or equal to 10V) than that required in a plasma display panel or an inorganic Electroluminescent (EL) display. The organic electroluminescent device is advantageous in that it consumes less power and provides excellent color display compared to other display devices. Also, since the organic electroluminescent device can reproduce pictures using three colors (i.e., green, blue, and red), the organic electroluminescent device is widely recognized as a next-generation color display device that can reproduce clear images.
The process of fabricating an organic Electroluminescent (EL) device is described as follows:
(1) the anode material is coated on a transparent substrate. Generally, Indium Tin Oxide (ITO) is used as an anode material.
(2) A Hole Injection Layer (HIL) is deposited on the anode material. The hole injection layer is formed of a copper phthalocyanine (CuPc) layer having a thickness of 10 nanometers (nm) to 30 nm.
(3) A void-transporting layer (HTL) is then deposited. The hole transport layer is mainly formed of 4, 4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), which is first treated with vacuum evaporation and then coated to have a thickness of 30 nanometers (nm) to 60 nanometers (nm).
(4) Thereafter, an organic light emitting layer is formed. At this time, a dopant may be added, if necessary. In the case of green light emission, the organic light emitting layer is typically evaporated from vacuum to tris (8-hydroxyquinolinato) aluminum (Alq) having a thickness of 30 to 60 nanometers (nm)3) And (4) forming. And, MQD (N-methyl quinacridone copper) is used as a dopant (or impurity).
(5) An Electron Transport Layer (ETL) and an Electron Injection Layer (EIL) are sequentially formed on the organic light emitting layer, or an electron injection/transport layer is formed on the organic light emitting layer. In the case of green light emission, Alq of step (4)3Has excellent electron transmission capacity. Therefore, electron injection and transport layers are not necessarily required.
(6) Finally, a cathode layer is coated, and a protective layer is coated on the whole structure.
Light emitting devices that emit (or display) blue, green, and red colors, respectively, are determined according to the method of forming the light emitting layer in the above structure. As the light emitting material, excitons are formed by recombination of electrons and holes injected from each electrode. Singlet excitons emit fluorescence and triplet excitons emit phosphorescence. Singlet excitons that emit fluorescence have a 25% formation probability, whereas triplet excitons that emit phosphorescence have a 75% formation probability. Thus, triplet excitons provide greater luminous efficiency than singlet excitons. In such a phosphorescent material, the green phosphorescent material may have greater luminous efficiency than the fluorescent material. Accordingly, as an important factor for improving the efficiency of the organic electroluminescent device, a green phosphorescent material is being widely studied.
When such a phosphorescent material is used, high luminous efficiency, high color purity and prolonged durability are required. Most particularly, when a green phosphorescent material is used, visibility is reduced as color purity increases (i.e., X value of CIE chromaticity coordinates becomes larger), thereby causing difficulty in providing high luminous efficiency. Accordingly, there is a need to develop a green phosphorescent material that can provide excellent chromaticity coordinates, improved luminous efficiency, and extended durability.
Disclosure of Invention
An object of the present invention devised to solve the problem lies on providing a green phosphorescent compound and an organic electroluminescent device using the same that substantially obviate one or more problems due to limitations and disadvantages of the related art.
Another object of the present invention devised to solve the problem lies on providing an organic electroluminescent device having high color purity, high luminance and long durability by incorporating the compound and the compound represented by formula (i) into a light-emitting layer of the organic electroluminescent device as a dopant.
The object of the present invention can be achieved by providing a green phosphorescent compound represented by the following formula (I).
A green phosphorescent compound represented by the following formula (I):
wherein LA and LB represent mono-, di-, tri-or tetra-substitution;
wherein X is selected from O, S, Se;
wherein LA, LB, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, and R18 are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
one is cycloalkyl, bicycloalkyl or polycycloalkyl; and wherein n is 1 or 2.
The green phosphorescent compound is selected from any one of the following compounds:
in another aspect of the present invention, there is provided an organic electroluminescent device comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode, which are sequentially deposited one on another, wherein the organic electroluminescent device may use any one of the above formulae as a dopant of the light emitting layer.
Here, any one of Al and Zn metal complexes and carbazole derivatives may be used as a host material of the light emitting layer, and the amount of the dopant used may be in the range of 0.1 wt% to 50 wt%. When the amount of the dopant used is within the above range, the efficiency of the present invention can be improved. And the ligand of each of the Al and Zn metal complexes may include quinolyl, biphenyl, isoquinolyl, phenyl, methylquinolyl, dimethylquinolyl, dimethylisoquinolyl, wherein the carbazole derivative may include CBP.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention, illustrate embodiments of the invention and together with the description serve to explain the principle of the invention.
In the drawings:
fig. 1 illustrates a graph showing a decrease in visibility as the color purity of an organic electroluminescent device increases (i.e., as the X value of chromaticity coordinates becomes larger).
FIG. 2 illustrates the structural formulae of the compounds copper (II) phthalocyanine (CuPc), NPB, Ir (ppy)3, BCP, Alq3 and CBP used in the embodiments of the present invention.
Detailed Description
Reference will now be made in detail to the preferred embodiments of the present invention, examples of which are illustrated in the accompanying drawings.
The method of forming the green phosphorescent compound according to the present invention is described below.
1. Synthesis of intermediate I-1
To a three-necked flask was added 2-chloro-3-fluoro-4-iodopyridine (30g, 116.5mmol), 2-methoxyphenylboronic acid (17.7g, 116.5mmol), and 2M-potassium carbonate (250mL) dissolved in tetrahydrofuran (250mL) under nitrogen.The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 mol%) as a catalyst was added. The reaction was warmed to 80 ℃ and stirred under reflux for 12 hours. After cooling to room temperature, the reaction mixture was quenched with water, and the reaction mixture was extracted with ethyl acetate and saturated brine. The mixture was washed with saturated brine two to three times, and the organic phase was taken out. The organic phase was dried over anhydrous magnesium sulfate and concentrated. Purification by silica gel column chromatography gave intermediate I-1(20.8g, yield: 75%). LC-MS: M/Z238.7(M + H))+
2. Synthesis of intermediate I-2
Me3SiSNa was prepared by adding Me3SiSSiMe3(30.0g, 168.3mmol) and NaOMe (5.0g, 92.6mmol) to dry 1, 3-dimethyl-Z-imidazolidinone (100mL) at room temperature. To this solution was then added intermediate I-1(20g, 84.2 mmol). The temperature is raised to 120 ℃ and 150 ℃ for reaction, and the intermediate I-2(8.9g, yield: 52%) is obtained after post-treatment and purification by a column. LC-MS: M/Z204.6(M + H))+
3. Synthesis of ligand L-1
Intermediate I-2(8g, 39.3mmol), phenylboronic acid (5.3g, 43.2mmol), 2M-potassium carbonate (80mL) was dissolved in tetrahydrofuran (80mL) in a three-necked flask under nitrogen. The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 mol%) as a catalyst was added. The reaction was warmed to 80 ℃ and stirred under reflux for 12 hours. After cooling to room temperature, the reaction mixture was quenched with water, and the reaction mixture was extracted with ethyl acetate and saturated brine. The mixture was washed with saturated brine two to three times, and the organic phase was taken out. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The ligand L-1(8.2g, yield: 85%) was obtained by separation and purification through a silica gel column. LC-MS: M/Z246.3(M + H))+
4. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (3g, 10mmol), 2-phenylpyridine (3.4g, 22.1mmol) and diethanol monoethyl ether in a ratio of 3/1(120mL/40mL) to distilled water was charged into a dry two-necked round-bottomed flask, and heated under reflux for 24 hours, followed by addition of an appropriate amount of distilled water, and the precipitated solid was filtered and washed with methanol and petroleum ether to obtain a dichloro-crosslinked dimer complex (3.2g, yield: 60%). LC-MS: M/Z1073.1(M + H))+
5. Synthesis of intermediate I-3
In a round bottom flask, dichloro-crosslinked dimer complex (3g, 2.8mmol) was dissolved in 200mL of dichloromethane. In a separate flask, trifluoro, silver (I) methanesulfonate (1.6g, 6.2mmol) was dissolved in 100 mM LEOH. It was added slowly to the dimer solution at room temperature with constant stirring. The reaction was stirred overnight in the dark and then filtered through celite to remove the silver chloride precipitate. The solvent was removed under reduced pressure to give intermediate I-3(4.1g, yield: 100%) which was used without further purification. LC-MS: M/Z729.8(M + H))+
Synthesis of GD-001
Intermediate I-3(4.0g, 5.5mmol) and ligand L-1(4.0g, 16.5mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using 65 to 100% dichloromethane-containing hexane eluent to obtain GD-001(2.5g, yield: 60%). LC-MS: M/Z745.9(M + H)+
7. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (3g, 10mmol), 5-methyl-2-phenylpyridine (3.7g, 22.1mmol) and diethanol monoethyl ether in a ratio of 3/1(120mL/40mL) to distilled water was charged into a dry two-necked round-bottomed flask, and heated under reflux for 24 hours, followed by addition of an appropriate amount of distilled water, and the precipitated solid was filtered and washed with methanol and petroleum ether to give a dichloro-crosslinked dimer complex (3.4g, yield: 60%). LC-MS: M/Z1129.2(M + H))+
8. Synthesis of intermediate I-4
In a round bottom flask, dichloro-crosslinked dimer complex (3g, 2.7mmol) was dissolved in 200mL of dichloromethane. In a separate flask, trifluoro, silver (I) methanesulfonate (1.5g, 5.9mmol) was dissolved in 100 mM LEOH. It was added slowly to the dimer solution at room temperature with constant stirring. The reaction was stirred overnight in the dark and then filtered through celite to remove the silver chloride precipitate. The solvent was removed under reduced pressure to give intermediate I-4(4.0g, yield: 100%) which was used without further purification. LC-MS: M/Z757.8(M + H))+
Synthesis of GD-037
Intermediate I-4(4.0g, 5.3mmol) and ligand L-1(3.9g, 15.9mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using a hexane eluent containing 65 to 100% dichloromethane to obtain GD-001(2.7g, yield: 65%). LC-MS: M/Z773.9(M + H)+
10. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (3g, 10mmol), 5-methyl-2- (4-tolyl) pyridine (4.1g, 22.1mmol) and diethanol monoethyl ether in a ratio of 3/1(120mL/40mL) to distilled water was charged into a dry two-necked round-bottomed flask, heated under reflux for 24 hours, followed by addition of an appropriate amount of distilled water, and the precipitated solid was filtered and washed with methanol and petroleum ether to give a dichloro-crosslinked dimer complex (3.9g, yield: 65%). LC-MS: M/Z1185.3(M + H))+
11. Synthesis of intermediate I-5
In a round bottom flask, dichloro-crosslinked dimer complex (3g, 2.5mmol) was dissolved in 200mL of dichloromethane. In a separate flask, trifluoro, silver (I) methanesulfonate (1.4g, 5.6mmol) was dissolved in 100 mM LEOH. It was added slowly to the dimer solution at room temperature with constant stirring. The reaction was stirred overnight in the dark and then filtered through celite to remove the silver chloride precipitate. The solvent was removed under reduced pressure to give intermediate I-5(4.0g, yield: 100%) which was used without further purification. LC-MS: M/Z785.9(M + H))+
Synthesis of GD-039
Intermediate I-5(4.0g, 5.1mmol) and ligand L-1(3.8g, 15.3mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using 65-100% dichloromethane-containing hexane eluent to obtain GD-001(2.7g, yield: 66%). LC-MS: M/Z802.0(M + H)+
13. Synthesis of ligand L-2
A solution of 5-methyl-2-phenylpyridine (10g, 59.1mmol) and NaOtBu (2.8g, 29.5mmol) in DMSO-d6(50mL) was refluxed at 80 ℃ for 12 hours. The reaction was quenched by D2O (50mL) and extracted with saturated brine and EtOAc. The combined organic layers were dried and filtered through celite. The filtrate was then concentrated and distilled to give ligand L-2(8.1g, yield: 80%). LC-MS: M/Z173.2(M + H))+
14. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (3g, 10mmol), ligand L-2(3.8g, 22.1mmol) and diethanolamoether in a ratio of 3/1(120mL/40mL) to distilled water was charged into a dry two-necked round-bottomed flask, and heated under reflux for 24 hours, then an appropriate amount of distilled water was added, and the precipitated solid was filtered and washed with methanol and petroleum ether to obtain a dichloro-crosslinked dimer complex (3.4g, yield: 60%). LC-MS: M/Z1141.3(M + H))+
15. Synthesis of intermediate I-6
In a round bottom flask, dichloro-crosslinked dimer complex (3g, 2.6mmol) was dissolved in 200mL of dichloromethane. In a separate flask, trifluoro, silver (I) methanesulfonate (1.5g, 5.8mmol) was dissolved in 100 mM LEOH. It was added slowly to the dimer solution at room temperature with constant stirring. The reaction was stirred overnight in the dark and then filtered through celite to remove the silver chloride precipitate. The solvent was removed under reduced pressure to give intermediate I-6(4.0g, yield: 100%) which was obtained without further purificationThe application is as follows. LC-MS: M/Z763.9(M + H))+
Synthesis of GD-049
Intermediate I-6(4.0g, 5.2mmol) and ligand L-1(3.9g, 15.7mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After evaporation of the solvent, the crude product was purified by column chromatography using 65-100% dichloromethane in hexane as eluent to obtain GD-049(2.7g, yield: 65%). LC-MS: M/Z780.0(M + H)+
17. Synthesis of ligand L-3
A solution of 5-methyl-2- (4-tolyl) pyridine (10g, 54.0mmol) and NaOtBu (2.6g, 23.0mmol) in DMSO-d6(50mL) was refluxed at 80 ℃ for 12 hours. The reaction was quenched by D2O (50mL) and extracted with saturated brine and EtOAc. The combined organic layers were dried and filtered through celite. The filtrate was then concentrated and distilled to give ligand L-3(7.4g, yield: 72%). LC-MS: M/Z190.3(M + H))+
18. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (3g, 10mmol), ligand L-3(4.2g, 22.1mmol) and diethanolamoether in a ratio of 3/1(120mL/40mL) to distilled water was charged into a dry two-necked round-bottomed flask, and heated under reflux for 24 hours, then an appropriate amount of distilled water was added, and the precipitated solid was filtered and washed with methanol and petroleum ether to obtain a dichloro-crosslinked dimer complex (3.6g, yield: 60%). LC-MS: M/Z1209.5(M + H))+
19. Synthesis of intermediate I-7
In a round bottom flask, dichloro-crosslinked dimer complex (3g, 2.5mmol) was dissolved in 200mL of dichloromethane. In a separate flask, trifluoro, silver (I) methanesulfonate (1.4g, 5.5mmol) was dissolved in 100 mM LEOH. It was added slowly to the dimer solution at room temperature with constant stirring. The reaction was stirred overnight in the dark and then filtered through celite to remove the silver chloride precipitate. The solvent was removed under reduced pressure to give intermediate I-7(4.0g, yield: 100%) which was used without further purification. LC-MS: M/Z798.0(M + H))+
Synthesis of GD-051
Intermediate I-7(4.0g, 5.0mmol) and ligand L-1(3.7g, 15.1mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using a hexane eluent containing 65 to 100% dichloromethane to obtain GD-051(2.7g, yield: 66%). LC-MS: M/Z814.0(M + H)+
21. Synthesis of intermediate I-8
Intermediate I-2(8g, 39.3mmol), 4-tolueneboronic acid (5.9g, 43.2mmol), 2M-potassium carbonate (80mL) was dissolved in tetrahydrofuran (80mL) in a three-necked flask under nitrogen. The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 mol%) as a catalyst was added. The reaction was warmed to 80 ℃ and stirred under reflux for 12 hours. After cooling to room temperature, the reaction mixture was quenched with water, and the reaction mixture was extracted with ethyl acetate and saturated brine. The mixture was washed with saturated brine two to three times, and the organic phase was taken out. The organic phase was dried over anhydrous magnesium sulfate and concentrated. Separation and purification by means of a silica gel column chromatography gave ligand I-8(8.6g, yield: 84%). LC-MS: M/Z260.3(M + H))+
22. Synthesis of ligand L-4
A solution of ligand I-6(10g, 38.6mmol) and NaOtBu (1.9g, 19.3mmol) in DMSO-d6(50mL) was refluxed at 80 ℃ for 12 h. The reaction was quenched by D2O (50mL) and extracted with saturated brine and EtOAc. The combined organic layers were dried and filtered through celite. The filtrate was then concentrated and distilled to give ligand L-4(7.1g, yield: 70%). LC-MS: M/Z190.3(M + H))+
Synthesis of GD-157
Intermediate I-3(4.0g, 5.5mmol) and ligand L-4(4.3g, 16.5mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using 65 to 100% dichloromethane-containing hexane eluent to obtain GD-157(2.6g, yield: 62%). LC-MS: M/Z762.9(M + H)+
Synthesis of GD-193
Intermediate I-6(4.0g, 5.2mmol) and ligand L-4(4.1g, 15.7mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using 65-100% dichloromethane in hexane as an eluent to obtain GD-193(2.6g, yield: 63%). LC-MS: M/Z780.0(M + H)+
Synthesis of GD-195
Intermediate I-7(4.0g, 5.0mmol) and ligand L-4 (3).9g, 15.1mmol) was dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using 65-100% dichloromethane-containing hexane eluent to obtain GD-195(2.5g, yield: 60%). LC-MS: M/Z831.1(M + H)+
Examples of preferred embodiments are given below to describe the present invention. It should be clearly understood that the invention is not limited to the presented embodiments only.
Example 1
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance was equal to 5210cd/m2(6.2V). In this case, CIEx is 0.365 and y is 0.608.
Example 2
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 5740cd/m2(6.0V). At this time, CIEx is 0.337 and y is 0.623.
Example 3
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. Subsequently subjecting the base toThe plate is placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance was equal to 6570cd/m2(5.6V). In this case, CIEx is 0.345 and y is 0.618.
Example 4
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 5980cd/m2(5.9V). In this case, CIEx is 0.335 and y is 0.622.
Example 5
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 6630cd/m2(5.4V). In this case, CIEx is 0.342 and y is 0.619.
Example 6
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, washingA patterned ITO glass substrate. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 5370cd/m2(5.8V). In this case, CIEx is 0.362 and y is 0.611.
Example 7
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 6020cd/m2(5.6V). In this case, CIEx is 0.338 and y is 0.622.
Example 8
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to cd/m2(5.5V). In this case, CIEx is 0.344 and y is 0.620.
Comparative example
Patterning an ITO glass substrate to haveA 3mm x 3mm light emitting area. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. On an ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. When a hole-carrying layer was formed using BALq, luminance was 4550cd/m at 0.9mA2(6.7V). In this case, CIEx is 0.332 and y is 0.618.
According to the above examples 1 to 8 and comparative examples, the characteristics of efficiency, chromaticity coordinates and luminance are shown in table 1 below.
TABLE 1
As shown in table 1, the device operates at high efficiency at low voltage even when the color purity is high. Also, the current efficiency of the second embodiment is increased by 30% or more compared to the comparative example.
It will be apparent to those skilled in the art that many modifications and variations can be made in the present invention without departing from the spirit and scope of the invention. It is therefore contemplated that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.
Industrial applicability
The present invention provides an organic electroluminescent device having excellent color purity and brightness and prolonged durability by using the compound represented by formula (i) as a light emitting layer of the organic electroluminescent device.
Claims (5)
1. A green phosphorescent compound having a structure shown below:
2. an organic electroluminescent device comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode deposited in this order, which uses the compound of claim 1 as a dopant.
3. The organic electroluminescent device as claimed in claim 2, wherein any one of Al and Zn metal complexes and CBP is used as a host material of the light emitting layer.
4. The organic electroluminescent device as claimed in claim 2, wherein any one of Al and Zn metal complexes and CBP is used as a host material of the light emitting layer, wherein the dopant is used in an amount ranging from 0.1 wt% to 50 wt%.
5. The organic electroluminescent device as claimed in claim 3 or 4, wherein the ligand of the Al and Zn metal complex is selected from the group consisting of quinolyl, isoquinolyl, methylquinolyl, dimethylquinolyl and dimethylisoquinolyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910038120.3A CN109988193B (en) | 2019-01-16 | 2019-01-16 | Green phosphorescent compound and organic electroluminescent device using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910038120.3A CN109988193B (en) | 2019-01-16 | 2019-01-16 | Green phosphorescent compound and organic electroluminescent device using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109988193A CN109988193A (en) | 2019-07-09 |
| CN109988193B true CN109988193B (en) | 2021-11-16 |
Family
ID=67130152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910038120.3A Active CN109988193B (en) | 2019-01-16 | 2019-01-16 | Green phosphorescent compound and organic electroluminescent device using the same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109988193B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111116674A (en) * | 2019-12-27 | 2020-05-08 | 吉林奥来德光电材料股份有限公司 | Iridium metal complex luminescent material and preparation method and application thereof |
| EP4039691A1 (en) | 2021-02-05 | 2022-08-10 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device |
| CN114478650A (en) * | 2022-01-28 | 2022-05-13 | 上海八亿时空先进材料有限公司 | Metal complex and organic electroluminescent device containing same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102449107A (en) * | 2009-04-06 | 2012-05-09 | 通用显示公司 | Metal complex comprising novel ligand structures |
| CN111132986A (en) * | 2017-11-24 | 2020-05-08 | 株式会社Lg化学 | Novel compound and organic light emitting device comprising the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10003035B2 (en) * | 2014-11-28 | 2018-06-19 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
-
2019
- 2019-01-16 CN CN201910038120.3A patent/CN109988193B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102449107A (en) * | 2009-04-06 | 2012-05-09 | 通用显示公司 | Metal complex comprising novel ligand structures |
| CN111132986A (en) * | 2017-11-24 | 2020-05-08 | 株式会社Lg化学 | Novel compound and organic light emitting device comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109988193A (en) | 2019-07-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20210094502A (en) | Ancillary ligands for organometallic complexes | |
| KR100803125B1 (en) | Red phosphorescent compounds and organic electroluminescence devices using the same | |
| JP4870245B2 (en) | Phosphorescent light emitting device material and organic electroluminescent device using the same | |
| KR20220000886A (en) | Organic electroluminescent materials and devices | |
| KR20220020309A (en) | Phosphorescent compound | |
| KR100662378B1 (en) | Red phosphorescene compounds and organic electroluminescence devices using the same | |
| KR101982337B1 (en) | Novel heteroleptic iridium complexes | |
| KR101950045B1 (en) | Substituted oligoazacarbazoles for light emitting diodes | |
| KR20190088453A (en) | Novel organic light emitting materials | |
| KR102637435B1 (en) | Organic electroluminescent materials and devices | |
| KR20180118253A (en) | Pyridyl carbene phosphorescent emitters | |
| KR20060098859A (en) | Red phosphorescent compounds and organic electroluminescence devices using the same | |
| WO2012064499A1 (en) | Phosphorescent materials | |
| CN111978355A (en) | Organic compound and organic electroluminescent device using the same | |
| CN110981913A (en) | Green phosphorescent compound and organic electroluminescent device using the same | |
| CN109988193B (en) | Green phosphorescent compound and organic electroluminescent device using the same | |
| CN108997438B (en) | Red phosphorescent compound and organic light emitting diode device using the same | |
| KR20140011952A (en) | Diarylamino substituted metal complexes | |
| CN109810146B (en) | Green phosphorescent compound and organic electroluminescent device using the same | |
| CN110964063A (en) | Green phosphorescent compound and organic electroluminescent device using the same | |
| CN111116673A (en) | Red phosphorescent compound and organic electroluminescent device using the same | |
| CN110724168A (en) | Red phosphorescent compound and organic electroluminescent device using the same | |
| KR20090032250A (en) | Red phosphorescence compound and organic electroluminescence device using the same | |
| CN110938097A (en) | Green phosphorescent compound and organic electroluminescent device using the same | |
| KR20130081240A (en) | Highly efficient phosphorescent materials |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |