CN105859714A - Thermal activation delayed fluorescence material containing 1, 10 phenanthroline unit and application of material - Google Patents
Thermal activation delayed fluorescence material containing 1, 10 phenanthroline unit and application of material Download PDFInfo
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- CN105859714A CN105859714A CN201610302127.8A CN201610302127A CN105859714A CN 105859714 A CN105859714 A CN 105859714A CN 201610302127 A CN201610302127 A CN 201610302127A CN 105859714 A CN105859714 A CN 105859714A
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- delayed fluorescence
- activation delayed
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- 239000000463 material Substances 0.000 title claims abstract description 88
- 230000003111 delayed effect Effects 0.000 title claims abstract description 52
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 title abstract 2
- 238000007725 thermal activation Methods 0.000 title abstract 2
- 230000004913 activation Effects 0.000 claims description 44
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical group [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 230000005540 biological transmission Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- 239000004411 aluminium Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 4
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000005525 hole transport Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000010348 incorporation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 150000002894 organic compounds Chemical class 0.000 abstract description 5
- -1 aromatic diphenylamine derivatives Chemical class 0.000 abstract description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002093 peripheral effect Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- 239000003205 fragrance Substances 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 150000007984 tetrahydrofuranes Chemical class 0.000 description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000002027 dichloromethane extract Substances 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 5
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 5
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 5
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- PPOPIFLDDYPIDD-UHFFFAOYSA-N 1h-pyrrole;silicon Chemical class [Si].C=1C=CNC=1 PPOPIFLDDYPIDD-UHFFFAOYSA-N 0.000 description 3
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 150000002991 phenoxazines Chemical class 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- HWTHOPMRUCFPBX-UHFFFAOYSA-N 9,9-diphenyl-10h-acridine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 HWTHOPMRUCFPBX-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 1
- 0 CC(Oc1c2cccc1)=C(CC*=C)N2c1ccc(ccc2ccc(N3c(cccc4)c4OC4C=CCCC34)nc22)c2n1 Chemical compound CC(Oc1c2cccc1)=C(CC*=C)N2c1ccc(ccc2ccc(N3c(cccc4)c4OC4C=CCCC34)nc22)c2n1 0.000 description 1
- ZCNVDTXCTQYFQK-ZQBXHCIJSA-N CCC(N(/C(/C)=N/C(c1nc(N2c3ccccc3C(c3ccccc3)(c3ccccc3)c3c2cccc3)ccc1CC1)=C1C=C)c1ccccc1C1(c2ccccc2)c2ccccc2)=C1/C=C\C Chemical compound CCC(N(/C(/C)=N/C(c1nc(N2c3ccccc3C(c3ccccc3)(c3ccccc3)c3c2cccc3)ccc1CC1)=C1C=C)c1ccccc1C1(c2ccccc2)c2ccccc2)=C1/C=C\C ZCNVDTXCTQYFQK-ZQBXHCIJSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
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Abstract
The invention provides a thermally-induced delayed fluorescence material and a preparation method of an organic electroluminescent device. The preparation method includes: using 1, 10 phenanthroline which is rigid as a strong-pull electron centronucleus and a diphenylamine derivative with high electron donating capability as a peripheral connecting group to form a D-A-D strong charge transfer state compound, wherein R1, R2 R3, R4, R5, R6, R7 and R8 are one of aromatic diphenylamine derivatives. The thermal activation delayed fluorescence material is simple to prepare and suitable for wide application. An organic compound obtained by the material can serve as a luminous layer material in OLEDs, and luminous efficiency and stability of the electroluminescent device can be improved by doping proper main materials.
Description
Technical field
The present invention relates to a kind of hot activation delayed fluorescence material and the OLED device using such hot activation delayed fluorescence material to prepare
Part.Hot activation delayed fluorescence material and such hot activation delayed fluorescence material of use particularly to a kind of core centered by luxuriant and rich with fragrance quinoline
The OLED of preparation.
Background technology
It is low that organic semiconducting materials has preparation cost compared with inorganic semiconductor material, the photoelectric properties that Modulatory character is good and excellent,
The Organic Light Emitting Diode (OLEDs) application aspect in the photoelectric device of the aspects such as display, illumination has bigger potentiality.
Photoelectric transformation efficiency is the important parameter of assessment OLED, since Organic Light Emitting Diode comes out, for improving organic light emission
The luminous efficiency of diode, various luminescent material systems based on fluorescence, phosphorescence are developed.OLED based on fluorescent material
Have the advantages that stability is high, but be limited to quantum statistics law, under electrical activation effect, the singlet excited exciton of generation
Being 1:3 with the ratio of triplet excited state exciton, therefore the inside electroluminescence quantum efficiency of fluorescent material is limited in 25%.Phosphorescence
Material is owing to having the Spin-orbit coupling interaction of heavy atom, and available triplet excited state exciton, its theoretical internal electron luminescent quantum is imitated
Rate is 100%, but OLED based on phosphorescence has obvious efficiency roll-off effect, and i.e. luminous efficiency is with the increasing of curtage
Reducing greatly and rapidly, this is particularly disadvantageous to the application of high brightness.
In order to overcome the shortcoming of both materials, Adachi etc. proposes and utilizes (the reverse intersystem that jumps of leaping up between reverse gap
Crossing) effect, makes full use of the thermic delayed fluorescence effect of triplet excited state exciton.The most just may utilize and do not contain heavy metal
The organic compound of atom realizes high efficiency that can be suitable with phosphorescent OLED, sees C.Adachi, et.al., Nature, Vol 492,
234,(2012).But the material doped thing of hot activation delayed fluorescence is decayed as the organic electroluminescence device of luminescent layer, its efficiency
The most quickly, device stability also has much room for improvement.Its reason is under high voltage and current, and its triplet excitons concentration increases, instead
Passing through between being that speed is limited causes Exciton quenching serious, exciton energy loss is relatively big, and device efficiency declines clearly.
Based on background above, prior art, the especially solution in terms of material could be improved and develop.
Summary of the invention
For existing hot activation delayed fluorescence material and the electroluminescent device of the existence such as hot activation delayed fluorescence OLED
The problem that material cost height, poor heat stability, efficiency roll-off are fast, the present invention provides a kind of thermic delayed fluorescence material and use
OLED prepared by such hot activation delayed fluorescence material.This material is using the 1,10 of rigidity luxuriant and rich with fragrance quinolines as haling electronic center
Core, has the diphenylamine derivative of strong electron donation as peripheral linking group, forms the strong charge transfer state of D-A-D type
Compound, R1、R2、R3、R4、R5、R6、R7And R8For having the one of armaticity diphenylamine derivatives.
The technical scheme that the present invention provides is specific as follows:
A kind of hot activation delayed fluorescence material, has a structure shown in Formulas I:
Wherein: RnForOr H, n are 1,2,3,4,5,6,7 or 8, X=O, S, C (CH3)2、
CPh2、Si(CH3)2Or SiPh2。
Work as R1And R8It is not H, R2、R3、R4、R5、R6And R7During for H, described hot activation delayed fluorescence material is
Work as R2And R7It is not H, R1、R3、R4、R5、R6And R8During for H, described hot activation delayed fluorescence material is
Work as R3And R6It is not H, R1、R2、R4、R5、R7And R8During for H, described hot activation delayed fluorescence material is
Work as R4And R5It is not H, R1、R2、R3、R6、R7And R8During for H, described hot activation delayed fluorescence material is
The application in electroluminescent field of the described hot activation delayed fluorescence material.
A kind of luminescent material, including hot activation delayed fluorescence material and organic functional material, described hot activation delayed fluorescence material
For one or more in the hot activation delayed fluorescence material shown in Formulas I, described organic functional material be hole injection layer material,
Hole transport layer material, electron transport layer materials, electron injecting layer material, electronic blocking layer material, hole barrier layer material,
One or more in luminescent material, material of main part.
A kind of electroluminescent hot activation delayed fluorescence device, substrate is glass, substrate be attached with the most successively Conducting Glass layer,
Hole transmission layer, auxiliary layer, luminescent layer, electron transfer layer, cathode layer, described luminescent layer is hot activation delayed fluorescence material
Or the activation delayed fluorescence material blends mixing material of main part forms, described hot activation delayed fluorescence material is shown in Formulas I
Electroluminescent hot activation delayed fluorescence material.
The material of main part mixed is 4-chlorobenzophenone, 4,4', 4 "-three (carbazole-9-base phenyl) amine or 4,4'-cyclohexyl two [N, N-bis-(4-
Aminomethyl phenyl) aniline].
Described hole transmission layer is 4,4 '-cyclohexyl two [N, N-bis-(4-aminomethyl phenyl) aniline]；Described auxiliary layer is 4,4 ', 4 "-
Three (carbazole-9-base) triphenylamine；Described electron transfer layer is 1,3,5-tri-(3-(3-pyridine radicals) phenyl) benzene；Described cathode layer is fluorine
Change lithium/aluminium.
According to the compound of the present invention, be conducive to obtaining thermic delayed fluorescence (TADF) characteristic of compound.According to TADF material
The principle of (seeing C.Adachi, et.al., Nature, 2012,492,234.), when singlet state and the difference of triplet of compound
(ΔEST) sufficiently small time, the triplet exciton of this compound can jump by leaping up between reverse gap (RISC) be converted to singlet excitons, from
And realize the utilization of all excitons.It is said that in general, TADF material is by electron donating group (Donor) and electron withdraw group (Acceptor)
It is connected and obtains, i.e. there is obvious D-A-D structure.
In preferred embodiments in this explanation, according to the compound of the present invention, there are obvious D-A-D structure, these compounds
All there is less Δ EST。
According to the luminescent device of the present invention, its electroluminescence wavelength is between 400nm to 900nm.
Compared with prior art, the present invention has the following advantages and beneficial effect:
1. the organic compound of the present invention is due to the rigid structure of luxuriant and rich with fragrance quinoline and big steric hindrance, can improve in molecule donor and acceptor it
Between torsion angle, thus obtain relatively low Δ EST, higher RISC speed and higher capacity usage ratio.
2. the organic compound of the present invention can be a kind of the most main by mixing as the TADF emitting layer material in OLED
Body material, can improve it and be used as the luminous efficiency in electroluminescent device and stability.
Accompanying drawing explanation
Fig. 1 is the EL device structure schematic diagram of the present invention, wherein: 1 glass and electro-conductive glass (ITO) substrate layer；2
Hole transmission layer (i.e. 4,4 '-cyclohexyl two [N, N-bis-(4-aminomethyl phenyl) aniline] TAPC)；3 auxiliary layers (i.e. 4,4 ', 4 "-three (clicks
Azoles-9-base) triphenylamine TCTA)；(present invention has the compound of delayed fluorescence or mixes as luminescent material using it 4 luminescent layers
Enter the mixture of material of main part)；5 electron transfer layers (i.e. 1,3,5-tri-(3-(3-pyridine radicals) phenyl) benzene Tm3PyPB)；6 negative electrodes
Layer (lithium fluoride/aluminium).
Fig. 2 is the luminescent spectrum of the electroluminescent device 1 of the present invention.
Fig. 3 is the luminescent spectrum of the electroluminescent device 2 of the present invention.
Detailed description of the invention
The present invention provides a kind of organic compound and the application in organic electroluminescence device thereof, the purpose of the present invention, technical side
Case and effect are clearer, clear and definite, and the present invention is described in more detail below, it will be appreciated that concrete reality described herein
Execute example only in order to explain the present invention, be not intended to limit the present invention.
The preparation of embodiment 1:2,9-bis--N-phenazinyl-1,10-phenanthrene quinoline
2,9-bis--N-phenazinyl-1,10-phenanthrene quinoline
1.3 grams of phenoxazines, 240 milligram of 70% oily scattered sodium hydride and 20 milliliters of oxolanes are added 50 milliliters of single port circles
In end flask, adding 0.75 gram 2 after refluxing 30 minutes under argon shield, the luxuriant and rich with fragrance quinoline of 9-bis-chloro-1,10, then at 60 degrees Celsius
Refluxing 24 hours, after being cooled to room temperature, saturated aqueous common salt cancellation, dichloromethane extracts, and anhydrous sodium sulfate is dried organic phase, mistake
Filter, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:20 and obtained product 1.35 grams.Greenish yellow solid, productivity 83%.1H NMR
(CDCl3, 400MHz): δ [ppm] 8.17 (d, J=8Hz, 2H), 7.77 (d, J=8Hz, 4H), 7.71 (s, 2H), 7.65 (d, J=
8Hz, 2H), 6.96 (d, J=4Hz, 8H), 6.88-6.84 (m, 4H) .MS (EI): m/z 542.3 [M]+.
The preparation of embodiment 2:4,7-bis--N-phenazinyl-1,10-phenanthrene quinoline
4,7-bis--N-phenazinyl-1,10-phenanthrene quinoline
1.30 grams of phenoxazines, 240 milligram of 70% oily scattered sodium hydride and 20 milliliters of oxolanes are added 50 milliliters of single port circles
In end flask, adding 0.75 gram 4 after refluxing 30 minutes under argon shield, the luxuriant and rich with fragrance quinoline of 7-bis-chloro-1,10, then at 60 degrees Celsius
Refluxing 24 hours, after being cooled to room temperature, saturated aqueous common salt cancellation, dichloromethane extracts, and anhydrous sodium sulfate is dried organic phase, mistake
Filter, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:30 and obtained product 1.40 grams.Light yellow solid, productivity 86%.1H NMR
(CDCl3, 400MHz): δ [ppm] 9.47 (d, J=8Hz, 2H), 8.07 (s, 2H), 7.77 (d, J=4Hz, 2H), 6.77 (d, J=
8Hz, 4H), 6.71-6.67 (m, 4H), 6.54-6.50 (m, 4H), 5.73 (d, J=8Hz, 4H) .MS (EI): m/z 542.4 [M]+.
The preparation of embodiment 3:4,7-bis--N-phenothiazinyl-1,10-phenanthrene quinoline
4,7-bis--N-phenothiazinyl-1,10-phenanthrene quinoline
1.41 grams of phenthazine, 240 milligram of 70% oily scattered sodium hydride and 20 milliliters of oxolanes are added 50 milliliters of single port circles
In end flask, adding 0.75 gram 4 after refluxing 30 minutes under argon shield, the luxuriant and rich with fragrance quinoline of 7-bis-chloro-1,10, then at 60 degrees Celsius
Refluxing 24 hours, after being cooled to room temperature, saturated aqueous common salt cancellation, dichloromethane extracts, and anhydrous sodium sulfate is dried organic phase, mistake
Filter, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:30 and obtained product 1.38 grams.Light yellow solid, productivity 80%.1H NMR
(CDCl3, 400MHz): δ [ppm] 9.48 (d, J=8Hz, 2H), 8.05 (s, 2H), 7.74 (d, J=4Hz, 2H), 7.21-7.16
(m,12H),6.97-6.87(m,4H).MS(EI):m/z 574.4[M]+.
The preparation of embodiment 4:4,7-bis--(N-9.9-dimethyl acridinium)-1,10-phenanthrene quinoline
4,7-bis--(N-9.9-dimethyl acridinium)-1,10-phenanthrene quinoline
1.46 grams of 9,9-dimethyl acridinium, 240 milligram of 70% oily scattered sodium hydride and 20 milliliters of oxolanes are added 50 millis
Rise in single necked round bottom flask, after refluxing 30 minutes under argon shield, add 0.75 gram 4, the luxuriant and rich with fragrance quinoline of 7-bis-chloro-1,10, then exist
60 degrees Celsius are refluxed 24 hours, and after being cooled to room temperature, saturated aqueous common salt cancellation, dichloromethane extracts, and anhydrous sodium sulfate is dried
Organic phase, filters, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:30 and obtained product 1.57 grams.White solid, productivity
88%.1H NMR(CDCl3, 400MHz): δ [ppm] 9.51 (d, J=4Hz, 2H), 8.07 (s, 2H), 7.74 (d, J=4Hz,
2H), 7.60 (s, 2H), 7.48 (d, J=12Hz, 4H), 6.92-6.82 (m, 8H), 5.98 (d, J=8Hz, 4H) .MS (EI): m/z
594.4[M]+.
The preparation of embodiment 5:4,7-bis--(N-9.9-diphenylacridine)-1,10-phenanthrene quinoline
4,7-bis--(N-9.9-diphenylacridine)-1,10-phenanthrene quinoline
2.33 grams of 9,9-diphenylacridine, 240 milligram of 70% oily scattered sodium hydride and 20 milliliters of oxolanes are added 50 millis
Rise in single necked round bottom flask, after refluxing 30 minutes under argon shield, add 0.75 gram 4, the luxuriant and rich with fragrance quinoline of 7-bis-chloro-1,10, then exist
60 degrees Celsius are refluxed 24 hours, and after being cooled to room temperature, saturated aqueous common salt cancellation, dichloromethane extracts, and anhydrous sodium sulfate is dried
Organic phase, filters, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:30 and obtained product 2.15 grams.White solid, productivity
85%.1H NMR(CDCl3, 400MHz): δ [ppm] 9.51 (d, J=4Hz, 2H), 8.07 (s, 2H), 7.74 (d, J=4Hz,
2H), 7.60 (s, 2H), 7.48 (d, J=12Hz, 4H), 7.33-6.98 (m, 20H), 6.92-6.82 (m, 8H), 5.98 (d, J=8Hz,
4H).MS(EI):m/z 842.3[M]+.
The preparation of embodiment 6:4,7-bis--N-10,10-dimethyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon oxazolyl-1,10-phenanthrene quinoline
4,7-bis--N-10,10-dimethyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon oxazolyl-1,10-phenanthrene quinoline
By 1.58 grams of 10,10-dimethyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon azoles, 240 milligram of 70% oily scattered sodium hydride and
20 milliliters of oxolanes add in 50 milliliters of single necked round bottom flask, add 0.75 gram 4,7-after refluxing 30 minutes under argon shield
Two chloro-1,10 luxuriant and rich with fragrance quinolines, then reflux 24 hours at 60 degrees Celsius, after being cooled to room temperature, and saturated aqueous common salt cancellation, dichloromethane
Alkane extracts, and anhydrous sodium sulfate is dried organic phase, filters, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:30 and obtained product 1.52
Gram.White solid, productivity 81%.1H NMR(CDCl3, 400MHz): δ [ppm] 9.47 (d, J=4Hz, 2H), 8.03 (s, 2H),
7.71 (d, J=4Hz, 2H), 7.54-7.41 (m, 8H), 7.21-7.10 (m, 4H), 6.97-6.89 (m, 4H), 0.57 (s, 6H) .MS
(EI):m/z 626.7[M]+.
The preparation of embodiment 7:4,7-bis--N-10,10-diphenyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon oxazolyl-1,10-phenanthrene quinoline
4,7-bis--N-10,10-diphenyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon oxazolyl-1,10-phenanthrene quinoline
By 2.44 grams of 10,10-diphenyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon azoles, 240 milligram of 70% oily scattered sodium hydride and
20 milliliters of oxolanes add in 50 milliliters of single necked round bottom flask, add 0.75 gram 4,7-after refluxing 30 minutes under argon shield
Two chloro-1,10 luxuriant and rich with fragrance quinolines, then reflux 24 hours at 60 degrees Celsius, after being cooled to room temperature, and saturated aqueous common salt cancellation, dichloromethane
Alkane extracts, and anhydrous sodium sulfate is dried organic phase, filters, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:30 and obtained product 2.18
Gram.White solid, productivity 83%.1H NMR(CDCl3, 400MHz): δ [ppm] 9.46 (d, J=4Hz, 2H), 7.99 (s, 2H),
7.65 (d, J=4Hz, 2H), 7.53-7.38 (m, 28H), 7.20-7.07 (m, 4H), 6.95-6.88 (m, 4H) .MS (EI): m/z
875.2[M]+.
The preparation of embodiment 8:3,8-bis--(N-9.9-diphenylacridine)-1,10-phenanthrene quinoline
3,8-bis--(N-9.9-diphenylacridine)-1,10-phenanthrene quinoline
2.33 grams of 9,9-diphenylacridine, 240 milligram of 70% oily scattered sodium hydride and 20 milliliters of oxolanes are added 50 millis
Rise in single necked round bottom flask, after refluxing 30 minutes under argon shield, add 0.75 gram 3, the luxuriant and rich with fragrance quinoline of 8-bis-chloro-1,10, then exist
60 degrees Celsius are refluxed 24 hours, and after being cooled to room temperature, saturated aqueous common salt cancellation, dichloromethane extracts, and anhydrous sodium sulfate is dried
Organic phase, filters, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:20 and obtained product 2.03 grams.White solid, productivity
80%.1H NMR(CDCl3, 400MHz): δ [ppm] 9.18 (d, J=4Hz, 2H), 8.35 (d, J=4Hz, 2H), 7.83 (s, 2H),
7.60 (s, 2H), 7.49 (d, J=12Hz, 4H), 7.36-6.99 (m, 20H), 6.95-6.83 (m, 8H), 6.04 (d, J=8Hz, 4H).
MS(EI):m/z 842.1[M]+.
The preparation of embodiment 9:3,8-bis--N-10,10-diphenyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon oxazolyl-1,10-phenanthrene quinoline
3,8-bis--N-10,10-diphenyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon oxazolyl-1,10-phenanthrene quinoline
By 2.44 grams of 10,10-diphenyl-5,10-dihydro-dibenzo [b, e] [1,4] silicon azoles, 240 milligram of 70% oily scattered sodium hydride and
20 milliliters of oxolanes add in 50 milliliters of single necked round bottom flask, add 0.75 gram 3,8-after refluxing 30 minutes under argon shield
Two chloro-1,10 luxuriant and rich with fragrance quinolines, then reflux 24 hours at 60 degrees Celsius, after being cooled to room temperature, and saturated aqueous common salt cancellation, dichloromethane
Alkane extracts, and anhydrous sodium sulfate is dried organic phase, filters, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:20 and obtained product 2.07
Gram.White solid, productivity 79%.1H NMR(CDCl3, 400MHz): δ [ppm] 9.21 (d, J=4Hz, 2H), 8.35 (d, J=4
Hz,2H),7.78(s,2H),7.57-7.39(m,28H),7.26-7.09(m,4H),6.97-6.89(m,4H).MS(EI):m/z 875.5
[M]+.
The preparation of embodiment 10:5,6-bis--N-phenazinyl-1,10-phenanthrene quinoline
5,6-bis--N-phenazinyl-1,10-phenanthrene quinoline
1.3 grams of phenoxazines, 240 milligram of 70% oily scattered sodium hydride and 20 milliliters of oxolanes are added 50 milliliters of single port circles
In end flask, adding 0.75 gram 5 after refluxing 30 minutes under argon shield, the luxuriant and rich with fragrance quinoline of 6-bis-chloro-1,10, then at 60 degrees Celsius
Refluxing 24 hours, after being cooled to room temperature, saturated aqueous common salt cancellation, dichloromethane extracts, and anhydrous sodium sulfate is dried organic phase, mistake
Filter, is spin-dried for.With methyl alcohol: methylene chloride volume is crossed post than 1:20 and obtained product 1.37 grams.Greenish yellow solid, productivity 84%.1H NMR
(CDCl3, 400MHz): δ [ppm] 8.97 (d, J=8Hz, 2H), 8.52 (d, J=8Hz, 2H), 8.14 (dd, 2H), 6.79-6.70
(m,8H),6.67-6.61(m,4H),6.03-5.99(m,4H).MS(EI):m/z 542.3[M]+.
Embodiment 11: the preparation of electroluminescent hot activation delayed fluorescence device
As it is shown in figure 1, the hot activation delayed fluorescence material of the present invention is as the electroluminescent hot activation delayed fluorescence device of luminescent layer, can
Including glass and electro-conductive glass (ITO) substrate layer 1, and hole transmission layer 2 (4,4 '-cyclohexyl two [N, N-bis-(4-aminomethyl phenyl) benzene
Amine] TAPC), auxiliary layer 3 (4,4 ', 4 "-three (carbazole-9-base) triphenylamine TCTA), (present invention has delayed fluorescence to luminescent layer 4
Compound or using its as luminescent material mix material of main part mixture), electron transfer layer 5 (1,3,5-tri-(3-(3-pyridine
Base) phenyl) benzene Tm3PyPB), cathode layer 6 (lithium fluoride/aluminium).
Electroluminescent hot activation delayed fluorescence device can be made by means known in the art, as by bibliography (Adv.Mater.2003,15,
277.) method disclosed in makes.Method particularly includes: in high vacuum conditions, at electro-conductive glass (ITO) substrate through over cleaning
On be deposited with successively, TAPC, TCTA, luminescent layer, the Al of LiF and 100nm of TmPyPB, 1nm.Use the party's legal system
Obtaining device as shown in Figure 1, various concrete device architectures are as follows:
Device 1 (D1):
ITO/TAPC (30nm)/TCTA (5nm)/CBP:1 (3wt.%, 15nm)/TmPyPB (65nm)/LiF (1nm)/Al (100nm)
Device 2 (D2):
ITO/TAPC (30nm)/TCTA (5nm)/CBP:2 (3wt.%, 15nm)/TmPyPB (65nm)/LiF (1nm)/Al (100nm)
Current versus brightness-the voltage characteristic of device is to be measured system by the Keithley source with corrected silicon photoelectric diode
(Keithley 2400Sourcemeter, Keithley 2000 Currentmeter) completes, and electroluminescent spectrum is by France JY
Company's SPEX CCD3000 spectrometer measurement, all measurements all complete in atmosphere at room temperature.
The performance data of device see table:
Describe the present invention above in association with preferred embodiment, but the invention is not limited in above-described embodiment, it will be appreciated that
Claims include the scope of the present invention and it should be appreciated by one skilled in the art that under the guiding of present inventive concept, to this
Certain change that each embodiment of invention is carried out, all will be covered by the spirit and scope of claims of the present invention.
Claims (7)
1. a hot activation delayed fluorescence material, it is characterised in that there is the structure shown in Formulas I:
Wherein: RnForOr H, n are 1,2,3,4,5,6,7 or 8, X=O, S, C (CH3)2、
CPh2、Si(CH3)2Or SiPh2。
Hot activation delayed fluorescence material the most according to claim 1, it is characterised in that:
Work as R1And R8It is not H, R2、R3、R4、R5、R6And R7During for H, described hot activation delayed fluorescence material is
Work as R2And R7It is not H, R1、R3、R4、R5、R6And R8During for H, described hot activation delayed fluorescence material is
Work as R3And R6It is not H, R1、R2、R4、R5、R7And R8During for H, described hot activation delayed fluorescence material is
Work as R4And R5It is not H, R1、R2、R3、R6、R7And R8During for H, described hot activation delayed fluorescence material is
3. the application in electroluminescent field of the hot activation delayed fluorescence material described in claim 1 or 2.
4. a luminescent material, including hot activation delayed fluorescence material and organic functional material, described hot activation delayed fluorescence material
Material is one or more in the hot activation delayed fluorescence material described in claim 1 or 2, and described organic functional material is empty
Cave implanted layer material, hole transport layer material, electron transport layer materials, electron injecting layer material, electronic blocking layer material, sky
One or more in cave barrier material, luminescent material, material of main part.
5. an electroluminescent hot activation delayed fluorescence device, substrate is glass, and substrate is attached with Conducting Glass the most successively
Layer, hole transmission layer, auxiliary layer, luminescent layer, electron transfer layer, cathode layer, it is characterised in that: described luminescent layer is heat
Activate delayed fluorescence material or mix the activation delayed fluorescence material blends composition of material of main part, described hot activation delayed fluorescence
Material is the electroluminescent hot activation delayed fluorescence material described in claim 1.
Electroluminescent hot activation delayed fluorescence device the most according to claim 5, it is characterised in that: the material of main part of incorporation is
4-chlorobenzophenone, 4,4 ', 4 "-three (carbazole-9-base phenyl) amine or 4,4 '-cyclohexyl two [N, N-bis-(4-aminomethyl phenyl) aniline].
7. according to the electroluminescent hot activation delayed fluorescence device described in claim 5 or 6, it is characterised in that: described hole transmission layer
It it is 4,4 '-cyclohexyl two [N, N-bis-(4-aminomethyl phenyl) aniline]；Described auxiliary layer is 4,4 ', 4 "-three (carbazole-9-base) triphenylamine；Institute
The electron transfer layer stated is 1,3,5-tri-(3-(3-pyridine radicals) phenyl) benzene；Described cathode layer is lithium fluoride/aluminium.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106831743A (en) * | 2016-12-30 | 2017-06-13 | 上海天马有机发光显示技术有限公司 | A kind of electroluminescent organic material and organic photoelectric device |
| CN107445913A (en) * | 2017-08-15 | 2017-12-08 | 武汉大学 | A kind of fluorescent material of structure containing beta diketone and its preparation and application |
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| CN111574505A (en) * | 2020-05-22 | 2020-08-25 | 西安瑞联新材料股份有限公司 | Compound with benzo [ c ] cinnoline as receptor and application thereof |
| CN116514778A (en) * | 2023-06-26 | 2023-08-01 | 季华实验室 | Organic electronic transmission material and organic electroluminescent device |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004331586A (en) * | 2003-05-08 | 2004-11-25 | Tokyo Institute Of Technology | 1,10- phenanthroline derivative, chelating ligand, and method for producing 1,10-phenanthroline derivative |
| CN103288825A (en) * | 2012-02-27 | 2013-09-11 | 海洋王照明科技股份有限公司 | Organic semiconductor material containing phenanthroline and preparation method and application thereof |
| CN105294670A (en) * | 2015-11-20 | 2016-02-03 | 上海天马有机发光显示技术有限公司 | Organic electroluminescent compound and organic photoelectric apparatus thereof |
| WO2016017688A1 (en) * | 2014-07-31 | 2016-02-04 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENCE ELEMENT, DISPLAY DEVICE, ILLUMINATION DEVICE, π-CONJUGATED COMPOUND, AND LIGHT-EMITTING THIN FILM |
| CN105418617A (en) * | 2015-12-25 | 2016-03-23 | 上海天马有机发光显示技术有限公司 | Organic electroluminescenct compound and organic photoelectric apparatus therewith |
-
2016
- 2016-05-09 CN CN201610302127.8A patent/CN105859714A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004331586A (en) * | 2003-05-08 | 2004-11-25 | Tokyo Institute Of Technology | 1,10- phenanthroline derivative, chelating ligand, and method for producing 1,10-phenanthroline derivative |
| CN103288825A (en) * | 2012-02-27 | 2013-09-11 | 海洋王照明科技股份有限公司 | Organic semiconductor material containing phenanthroline and preparation method and application thereof |
| WO2016017688A1 (en) * | 2014-07-31 | 2016-02-04 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENCE ELEMENT, DISPLAY DEVICE, ILLUMINATION DEVICE, π-CONJUGATED COMPOUND, AND LIGHT-EMITTING THIN FILM |
| CN105294670A (en) * | 2015-11-20 | 2016-02-03 | 上海天马有机发光显示技术有限公司 | Organic electroluminescent compound and organic photoelectric apparatus thereof |
| CN105418617A (en) * | 2015-12-25 | 2016-03-23 | 上海天马有机发光显示技术有限公司 | Organic electroluminescenct compound and organic photoelectric apparatus therewith |
Non-Patent Citations (1)
| Title |
|---|
| ACS: "RN66-71-7", 《REGISTRY》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10522760B2 (en) * | 2016-10-04 | 2019-12-31 | Samsung Display Co., Ltd. | Polycyclic compound and organic electroluminescence device including the same |
| US20180097181A1 (en) * | 2016-10-04 | 2018-04-05 | Samsung Display Co., Ltd. | Polycyclic compound and organic electroluminescence device including the same |
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| US20170256723A1 (en) * | 2016-12-30 | 2017-09-07 | Shanghai Tianma AM-OLED Co., Ltd. | Organic electroluminescent material and organic optoelectronic device |
| US10629822B2 (en) | 2016-12-30 | 2020-04-21 | Shanghai Tianma AM-OLED Co., Ltd. | Organic electroluminescent material and organic optoelectronic device |
| CN106831743A (en) * | 2016-12-30 | 2017-06-13 | 上海天马有机发光显示技术有限公司 | A kind of electroluminescent organic material and organic photoelectric device |
| CN107445913A (en) * | 2017-08-15 | 2017-12-08 | 武汉大学 | A kind of fluorescent material of structure containing beta diketone and its preparation and application |
| CN107445913B (en) * | 2017-08-15 | 2020-04-24 | 武汉大学 | Fluorescent material containing β -diketone structure and preparation and application thereof |
| WO2020015245A1 (en) * | 2018-07-18 | 2020-01-23 | 武汉华星光电半导体显示技术有限公司 | Thermally-activated delayed fluorescence material and synthesis method therefor |
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Application publication date: 20160817 |