CN106397490A - Iridium complex as well as preparation method thereof and electroluminescent device applied to iridium complex - Google Patents
Iridium complex as well as preparation method thereof and electroluminescent device applied to iridium complex Download PDFInfo
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- CN106397490A CN106397490A CN201610801601.1A CN201610801601A CN106397490A CN 106397490 A CN106397490 A CN 106397490A CN 201610801601 A CN201610801601 A CN 201610801601A CN 106397490 A CN106397490 A CN 106397490A
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- iridium
- pyrazine
- complex
- diphenyl
- dibenzo
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 54
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims description 53
- 238000002360 preparation method Methods 0.000 title claims description 11
- 238000010668 complexation reaction Methods 0.000 title 1
- BHHMPZQRVWVAAR-UHFFFAOYSA-N 7-bromo-8-methylpyrido[2,3-b]pyrazine Chemical compound C1=CN=C2C(C)=C(Br)C=NC2=N1 BHHMPZQRVWVAAR-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003446 ligand Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- 150000003222 pyridines Chemical class 0.000 claims description 13
- PTZIVVDMBCVSMR-UHFFFAOYSA-N 2,3-diphenylpyrazine Chemical compound C1=CC=CC=C1C1=NC=CN=C1C1=CC=CC=C1 PTZIVVDMBCVSMR-UHFFFAOYSA-N 0.000 claims description 11
- RSNQVABHABAKEZ-UHFFFAOYSA-N 2,3-diphenylquinoxaline Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 RSNQVABHABAKEZ-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 230000005540 biological transmission Effects 0.000 claims description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 238000006471 dimerization reaction Methods 0.000 claims description 6
- 150000002466 imines Chemical class 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 4
- -1 sun Pole Substances 0.000 claims description 4
- 239000010405 anode material Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000006617 triphenylamine group Chemical class 0.000 claims description 3
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- WKAXDAMWMOBXMP-UHFFFAOYSA-N 2,3-diphenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=C1 WKAXDAMWMOBXMP-UHFFFAOYSA-N 0.000 claims 2
- MKIFCLMEYDUTCD-UHFFFAOYSA-N 2,3-diphenylquinoxaline;iridium Chemical compound [Ir].C1=CC=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 MKIFCLMEYDUTCD-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 238000013461 design Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 238000000859 sublimation Methods 0.000 abstract description 3
- 230000008022 sublimation Effects 0.000 abstract description 3
- 150000002503 iridium Chemical class 0.000 abstract 3
- RYBGTOCMYDBVRW-UHFFFAOYSA-N 2,3-dibenzylpyrazine Chemical compound N=1C=CN=C(CC=2C=CC=CC=2)C=1CC1=CC=CC=C1 RYBGTOCMYDBVRW-UHFFFAOYSA-N 0.000 abstract 1
- IMOIAPIPPKKGRX-UHFFFAOYSA-N 2,3-dibenzylpyridine Chemical compound C=1C=CN=C(CC=2C=CC=CC=2)C=1CC1=CC=CC=C1 IMOIAPIPPKKGRX-UHFFFAOYSA-N 0.000 abstract 1
- PIUMNEGUDKLNJL-UHFFFAOYSA-N 2,3-dibenzylquinoxaline Chemical compound N=1C2=CC=CC=C2N=C(CC=2C=CC=CC=2)C=1CC1=CC=CC=C1 PIUMNEGUDKLNJL-UHFFFAOYSA-N 0.000 abstract 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 abstract 1
- KHPYJVQRBJJYSF-UHFFFAOYSA-N phenanthro[9,10-b]quinoxaline Chemical compound C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=CC=CC=C3C2=C1 KHPYJVQRBJJYSF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 abstract 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 18
- 238000005401 electroluminescence Methods 0.000 description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000000034 method Methods 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 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000011097 chromatography purification 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
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- QPUMEZIFDXYGPG-UHFFFAOYSA-N piperazine 1H-pyrrole Chemical compound N1CCNCC1.N1C=CC=C1 QPUMEZIFDXYGPG-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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)
Abstract
The invention relates to a kind of iridium complexes, which comprise a novel main ligand and an auxiliary ligand 4(4-trifluoromethyl-3-pyridyl)phosphonylimine or 4(4-trifluoromethyl-3,5-pyrimidinyl)phosphonylimine. The main ligand of the series of iridium complex molecules is any one of 2,3-dibenzylquinoxaline, 2,3-dibenzyl pyridine [2,3-b] pyrazine, 2,3-dibenzyl pyrazine [2,3-b] pyrazine, dibenzo[a,c]phenazine, and bipyridine[3,2-a:2',3'-c]phenazine derivatives. The novel kind of iridium complexes have the advantages of high luminous efficiency, stable chemical properties, easy sublimation and purification, excellent device performance, and the like. The molecular structure of the ligand is modified, so that luminous intensity and efficiency of the complexes are adjusted in the red light wavelength range, and convenience is provided for design and production of organic electroluminescent displays and lighting sources.
Description
【Technical field】
The present invention relates to organic electroluminescence device technical field, more particularly, to one class complex of iridium and preparation method thereof and
Apply the electroluminescent device of described complex of iridium.
【Background technology】
Under the overall background that global energy requirements are growing and ecological environment causes anxiety, national governments greatly develop base in succession
In high-tech energy sustainability technology and industry.Organic electroluminescence device (OLEDs) is because its visual angle is wide, brightness is high, energy consumption
Low and many advantages, such as flexible device can be prepared, and receive much attention, it is referred to as to dominate the key technology in the following display world.Closely
Nian Lai, numerous studies show, in numerous heavy metal element coordination compounds, complex of iridium be considered as OLEDs phosphor material
Ideal chose.There is 5d76s2The iridium atom of outer electronic structure, after formation+trivalent cation, has 5d6Electron configuration, has
Stable hexa-coordinate octahedral structure, makes material have higher chemical stability and heat stability.Meanwhile, Ir (III) has
Larger spin orbit coupling constant (ξ=3909cm-1), be conducive to improving the interior quantum yield of coordination compound and reducing the luminous longevity
Life, thus improve the overall performance of luminescent device.
As phosphor material, complex of iridium typically has Microsecond grade, easily causes the triplet-triplet of complex of iridium
And the phosphorescence of triplet-intensify between son is quenched.In addition, in current conventional material, the hole of hole mobile material
Mobility is far above the electron mobility of electron transport material, and conventional material of main part is also based on hole transport, and this can lead
Cause the gathering in luminescent layer and electric transmission bed boundary for the hole of great quantities of spare.These factors all can lead to the reduction of efficiency and tight
The efficiency roll-off of weight.Research shows, if complex of iridium has higher electron transport ability, can effectively increase electronics and exist
The transmission of luminescent layer and distribution, the region widening electron-hole, the quantity in balance electronic-hole pair, greatly improve device
Efficiency, reduces roll-offing of efficiency.
Therefore, it is necessary to provide a kind of complex of iridium with high-luminous-efficiency and electron mobility.
【Content of the invention】
It is an object of the invention to provide a class contains new main part, with four (4- trifluoromethyl -3- pyridine radicals) phosphine
Acid imide or four (4- trifluoromethyl -3,5- pyrimidine radicals) imines are complexes of red light iridium and its preparation side of assistant ligand
Method, such coordination compound can be applied in organic electroluminescence device as the centre of luminescence, and described assistant ligand is four (4- trifluoros
Methyl -3- pyridine radicals) imines or four (4- trifluoromethyl -3,5- pyrimidine radicals) imines.
The present invention provides a kind of complex of iridium, and it includes four main parts and an assistant ligand, and described main part is 2,
3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a,
C] azophenlyene, two pyridos [3,2-a:2 ', 3 '-c] any one in phenazene derivative.
Preferably, described 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine
[2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a:2 ', 3 '-c] phenazene derivative is selected from:In containing substituent group any one.
Preferably, described 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrrole
Piperazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a:2 ', 3 '-c] phenazene derivative substituent group be fluorine or
Person's trifluoromethyl.
Preferably, described complex of iridium has that to number as follows be one of structure of RIr10-01 to RIr10-32:
A kind of preparation method of complex of iridium is provided in the present invention:By the iridium dimerization bridging coordination compound containing four main parts
With assistant ligand and sodium carbonate mixing, described main part is 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrrole
Piperazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a:2 ', 3 '-c] azophenlyene derive
Any one in thing;Add cellosolvo solution, carry out reacting by heating at 120-140 DEG C, response time 12-48h,
It is cooled to room temperature, vacuum distillation removes solvent, then with dichloromethane extraction, concentrate, through column chromatography for separation, obtain the thick of coordination compound
Product, obtain pure complex of iridium through distillation.
Preferably, the mol ratio of described iridium dimerization bridging coordination compound, assistant ligand and sodium carbonate is 1: 2: 5.
The present invention also provides a kind of electroluminescent device of this complex of iridium of application, and it includes substrate, anode, hole transport
Layer, organic luminous layer, electron transfer layer and negative electrode, described substrate is glass, and anode material is tin indium oxide (ITO);Hole passes
Defeated layer uses 4,4 '-cyclohexyl two [N, N-- bis- (4- aminomethyl phenyl) aniline (TAPC), electron transport layer materials use 3,3 '-
(5 '-(3- (pyridin-3-yl) phenyl)-[1,1 ':3 ', 1 "-triphenyl] -3,3 "-diyl) two pyridines (TmPyPB), negative electrode employing
LiF/A1, organic luminous layer adopts the double emitting layers of doped structure, and described organic luminous layer includes material of main part and luminescent material,
Described material of main part is to use 4,4 ', 4 respectively " double (3- (9- carbazyl) benzene of-three (carbazole -9- base) triphenylamines (TcTa) and 2,6-
Base) pyridine (26DCzPPy), selected luminescent material is complex of iridium, mass fraction 5wt%.
Beneficial effects of the present invention:The complex of iridium that the present invention provides has luminous efficiency height, electron mobility is high and changes
Learn the features such as stable in properties, easy sublimation purification.The preparation method of described complex of iridium is simple, and yield is higher.Due to azacyclo-
Introduce, the electronic transmission performance of coordination compound can Effective Regulation, be the design of display of organic electroluminescence and lighting source
Production is provided convenience.
【Brief description】
Fig. 1 is used for the electroluminescent spectrum of organic electroluminescence device for the complex of iridium RIr10-01 that the present invention provides;
Fig. 2 is used for the brightness-voltage curve of organic electroluminescence device for the complex of iridium RIr10-01 that the present invention provides;
Fig. 3 is used for the current efficiency-brightness of organic electroluminescence device for the complex of iridium RIr10-01 that the present invention provides
Curve.
【Specific embodiment】
The present invention is described in further detail with reference to the accompanying drawings and examples.The term being used in the present invention, unless
It is otherwise noted, typically there is the implication of those of ordinary skill in the art's generally reason.
A kind of complex of iridium, it includes four main parts and an assistant ligand, and described main part is 2,3- diphenyl quinoline
Quinoline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyrroles
Pyridine simultaneously [3,2-a:2 ', 3 '-c] any one in phenazene derivative.Described 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines
[2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a:2 ', 3 '-c]
Phenazene derivative is selected from: In any one containing substituent group
Kind.Described assistant ligand is four (4- trifluoromethyl -3- pyridine radicals) imines or four (4- trifluoromethyl -3,5- pyrimidine radicals) phosphine
Acid imide.
The complex of iridium of the present invention all used in building-up process iridous chloride, ethylenediamine, 1,2- diphenylamine derivatives,
Dibenzoyl derivant, phenanthrenequione and 1,10- phenanthrolene -5,6-- diketone etc., synthetic method is similar to.
By the iridium dimerization bridging coordination compound containing four main parts and assistant ligand and sodium carbonate mixing, described main coordination compound
For 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo
[a, c] azophenlyene, two pyridos [3,2-a:2 ', 3 '-c] any one in phenazene derivative;Add cellosolvo solution,
Carry out reacting by heating, response time 12-48h at 120-140 DEG C, be cooled to room temperature, vacuum distillation removes solvent, then uses dichloro
Methane extracts, and concentrates, through column chromatography for separation, obtains the crude product of coordination compound, obtain complex of iridium through sublimation purification.Wherein, described
The mol ratio of iridium dimerization bridging coordination compound, assistant ligand and sodium carbonate is 1: 2: 5.
Described complex of iridium has that to number as follows be one of structure of RIr10-01 to RIr10-32:
Below with wherein one embodiment, numbering be RIr10-01 complex of iridium as a example illustrate present invention, lead to
Cross following embodiments to will be helpful to further understand the present invention, but do not limit present disclosure.
The synthetic method of coordination compound RIr10-01
Dibenzoyl (5.00mmol) and 1,2- phenylenediamine (5.00mmol) are dissolved in 50mL ethanol and flow back at 80 DEG C
24h, column chromatographic isolation and purification obtains the main part 2 of white, 3- diphenylquinoxaline (4.43mmol, yield:88.6%).To lead
Part (13.08mmol) and iridous chloride (6.23mmol) are dissolved in 15mL cellosolvo, 130 DEG C of reactions of mixture
12h, is subsequently adding assistant ligand (12.46mmol) and sodium carbonate (31.15mmol), continues 130 DEG C of reaction 24h.System cools down,
Add water and dichloromethane, organic layer concentrates column chromatography and obtains yellow solid RIr10-01, its yield is 45%.
Remaining method numbering the complex of iridium being RIr10-02~32 and structure and above-mentioned numbering are the iridium of RIr10-01
Coordination compound is similar, will not be described here.
The present invention with 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,
3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a:2 ', 3 '-c] any one in phenazene derivative be as master
Part, design has synthesized a series of complexes of red light iridium.By designing part or complex structure, and by simple on part
Chemical substituents modification, reach regulation and control coordination compound light and electron mobility purpose.
Described azacyclo- is all the group having stronger electron-transporting, is conducive to injection and the transmission of equilbrium carrier.
Described complex of iridium has higher luminous efficiency and electron mobility, after optimized checking, its preparation method letter
Single, and yield is higher.
The preparation of organic electroluminescence device
Present invention also offers a kind of organic electroluminescence device, it comprises any of the above-described numbering is RIr10-01~32
Complex of iridium.
As a example below organic electroluminescence device being prepared as luminescent material using RIr10-01, organic electroluminescence of the present invention is described
The preparation of luminescent device.The structure of OLEDs device includes:Substrate, anode, hole transmission layer, organic luminous layer and electric transmission
Layer/negative electrode.
In the element manufacturing of the present invention, substrate is glass, and anode material is tin indium oxide (ITO);Hole transmission layer uses
4, [N, N- bis- (4- aminomethyl phenyl) aniline (TAPC), electron transport layer materials use 3,3 '-(5 '-(3- (pyrrole to 4 '-cyclohexyl two
Pyridine -3- base) phenyl)-[1,1 ':3 ', 1 "-triphenyl] -3,3 "-diyl) two pyridines (TmPyPB), thickness is 60nm, evaporation speed
Rate is 0.05nm/s;Negative electrode adopts LiF/A1, organic luminous layer adopt doped structure double emitting layers, it include material of main part and
Luminescent material, material of main part is to use 4,4 ', 4 respectively "-three (carbazole -9- base) triphenylamines (TcTa) and double (3- (the 9- carbazole of 2,6-
Base) phenyl) pyridine (26DCzPPy), selected luminescent material is complex of iridium RIr10-01, the preferred 5wt% of mass fraction.
Different materials structure in the present invention is as follows:
The present invention selects a kind of HONGGUANG coordination compound to prepare organic electroluminescence device.See also Fig. 1, Fig. 2 and Fig. 3,
Fig. 1 is used for the electroluminescent spectrum of organic electroluminescence device for the complex of iridium that the present invention provides, Fig. 2 and Fig. 3 is the present invention
The complex of iridium providing is used for the photoelectric properties of organic electroluminescence device.As shown in Figures 2 and 3, described organic electroluminescent
The startup voltage of device is 3.8V, and its maximum power efficiency and current efficiency are respectively 57.04cd/A, high-high brightness 64589cd/
m2.By studying photophysical property, show that this kind of phosphorescent iridium complex containing azacyclo- has higher device efficiency, aobvious
The field such as show and illuminate and there is actual application value.
Such phosphor material that the present invention provides can be applied to the emission layer of phosphorescent OLED s as the centre of luminescence, by setting
Meter part or complex structure, and by modifying to the chemical substituents of described part, invention achieves regulation and control cooperation
Thing glow color and the purpose of efficiency.
Above-described is only embodiments of the present invention, it should be noted here that for those of ordinary skill in the art
For, without departing from the concept of the premise of the invention, improvement can also be made, but these belong to the protection model of the present invention
Enclose.
Claims (7)
1. it is characterised in that it includes four main parts and an assistant ligand, described main part is 2,3- to a kind of complex of iridium
Diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c]
Azophenlyene, two pyridos [3,2-a:2 ', 3 '-c] any one in phenazene derivative, described assistant ligand is four (4- fluoroforms
Base -3- pyridine radicals) imines or four (4- trifluoromethyl -3,5- pyrimidine radicals) imines.
2. complex of iridium according to claim 1 is it is characterised in that described 2,3- diphenylquinoxaline, 2,3- diphenyl
Pyridine [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a:2 ',
3 '-c] phenazene derivative is selected from: In containing substituent group appoint
Meaning is a kind of.
3. complex of iridium according to claim 1 is it is characterised in that described 2,3- diphenylquinoxaline, 2,3- diphenyl
Pyridine [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a:2 ',
3 '-c] phenazene derivative substituent group be fluorine or trifluoromethyl.
4. complex of iridium according to claim 1 is it is characterised in that described complex of iridium has one of following structure:
5. a kind of preparation method of the complex of iridium as described in any one as claim 1-4 is it is characterised in that will be containing four masters
The iridium dimerization bridging coordination compound of part and assistant ligand and sodium carbonate mixing, described main part is 2,3- diphenylquinoxaline, 2,
3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,
2-a:2 ', 3 '-c] any one in phenazene derivative;Add cellosolvo solution, heated at 120-140 DEG C
Reaction, response time 12-48h, it is cooled to room temperature, vacuum distillation removes solvent, then with dichloromethane extraction, concentrate, through post layer
Analysis separates, and obtains the crude product of coordination compound, obtains pure complex of iridium through distillation.
6. complex of iridium according to claim 5 preparation method it is characterised in that described iridium dimerization bridging coordination compound and
The mol ratio of sodium carbonate is 1: 5.
7. a kind of electroluminescent device of application complex of iridium as described in claim 1-3 any one, it includes substrate, sun
Pole, hole transmission layer, organic luminous layer, electron transfer layer and negative electrode, described substrate is glass, and anode material is tin indium oxide;
Hole transmission layer uses 4,4 '-cyclohexyl two [N, N- bis- (4- aminomethyl phenyl) aniline, electron transport layer materials use 3,3 '-
(5 '-(3- (pyridin-3-yl) phenyl)-[1,1 ': 3 ', 1 "-triphenyl] -3,3 "-diyl) two pyridines, negative electrode adopts LiF/Al,
Organic luminous layer adopts the double emitting layers of doped structure, and described organic luminous layer includes material of main part and luminescent material, described master
Body material is to use 4,4 ', 4 respectively "-three (carbazole -9- base) triphenylamines and double (3- (9- carbazyl) phenyl) pyridine of 2,6-, selected
Luminescent material is complex of iridium, mass fraction 5wt%.
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Cited By (4)
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CN109134550A (en) * | 2018-10-23 | 2019-01-04 | 常州大学 | D-A-D type ring metal iridium complex near-infrared light-emitting material and application based on aryl and quinoxaline |
WO2020136496A1 (en) * | 2018-12-28 | 2020-07-02 | 株式会社半導体エネルギー研究所 | Organic compound, light-emitting device, light-emitting apparatus, electronic instrument, and illumination apparatus |
US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11820783B2 (en) | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
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CN1890255A (en) * | 2003-12-02 | 2007-01-03 | 株式会社半导体能源研究所 | Organic metal complex and light-emitting device using same |
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CN1890255A (en) * | 2003-12-02 | 2007-01-03 | 株式会社半导体能源研究所 | Organic metal complex and light-emitting device using same |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN109134550A (en) * | 2018-10-23 | 2019-01-04 | 常州大学 | D-A-D type ring metal iridium complex near-infrared light-emitting material and application based on aryl and quinoxaline |
WO2020136496A1 (en) * | 2018-12-28 | 2020-07-02 | 株式会社半導体エネルギー研究所 | Organic compound, light-emitting device, light-emitting apparatus, electronic instrument, and illumination apparatus |
JP7478670B2 (en) | 2018-12-28 | 2024-05-07 | 株式会社半導体エネルギー研究所 | ORGANOMETAL COMPLEX, LIGHT-EMITTING DEVICE, LIGHT-EMITTING APPARATUS, ELECTRONIC DEVICE, AND LIGHTING APPARATUS |
US11820783B2 (en) | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
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