CN108484679A - A kind of thiobis diaryl/complex of iridium of the heterocyclic base phosphorimide as assistant ligand - Google Patents
A kind of thiobis diaryl/complex of iridium of the heterocyclic base phosphorimide as assistant ligand Download PDFInfo
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- CN108484679A CN108484679A CN201810099063.5A CN201810099063A CN108484679A CN 108484679 A CN108484679 A CN 108484679A CN 201810099063 A CN201810099063 A CN 201810099063A CN 108484679 A CN108484679 A CN 108484679A
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- Prior art keywords
- iridium
- complex
- azacyclo
- ligand
- heterocyclic base
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 56
- 239000003446 ligand Substances 0.000 title claims abstract description 36
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 21
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 title claims abstract description 16
- 238000005401 electroluminescence Methods 0.000 claims abstract description 20
- -1 pyrimidine radicals Chemical class 0.000 claims description 25
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 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 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 claims description 3
- 150000002240 furans Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000003851 azoles Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 38
- 238000002347 injection Methods 0.000 abstract description 8
- 239000007924 injection Substances 0.000 abstract description 8
- 238000000859 sublimation Methods 0.000 abstract description 6
- 230000008022 sublimation Effects 0.000 abstract description 6
- 230000005540 biological transmission Effects 0.000 abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 5
- 239000011574 phosphorus Substances 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 5
- 238000005286 illumination Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000006798 recombination Effects 0.000 abstract description 2
- 238000005215 recombination Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 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 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
- 0 CCCC(*)C1C=CC=C*1 Chemical compound CCCC(*)C1C=CC=C*1 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- KDOKHBNNNHBVNJ-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 KDOKHBNNNHBVNJ-UHFFFAOYSA-N 0.000 description 1
- LRTOHSLOFCWHRF-UHFFFAOYSA-N CC1c2ccccc2C=C1 Chemical compound CC1c2ccccc2C=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
- SKRKROTYQLXALL-UHFFFAOYSA-N [P]Br Chemical compound [P]Br SKRKROTYQLXALL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229930192474 thiophene Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/10—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
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- 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 present invention relates to one kind with azacyclo- for main ligand, using thiobis diaryl/heterocyclic base phosphorimide as the novel complex of iridium of assistant ligand.The azacyclo- and phosphorus methylthio group of complex of iridium intramolecular help to improve the electron mobility of material and regulation and control luminescent color widens the recombination region of carrier to balance the injection and transmission in hole and electronics, promote device efficiency, reduce efficiency roll-off.Complex of iridium synthesis of the present invention is simple, chemical property is stable, easy sublimation purification, and excellent device performance, to obtain efficient organic electroluminescence device and its providing convenience in illumination and the application of display field.
Description
Technical field
The present invention relates to organic electroluminescence device technical fields, more particularly to a kind of thiobis diaryl/heterocyclic base phosphorus
Acid imide is as the complex of iridium luminescent material of assistant ligand and the electroluminescent device of the application material.
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 (Organic Light-emitting Diode,
Abbreviation OLED), also known as Organic Light Emitting Diode is the device for applying voltage wherein and converting electrical energy into luminous energy.From 1987
Doctor Deng Qingyun of year Kodak has delivered the small molecule organic film double-layer structure of the efficient high brightness of low voltage starting
OLED since, the research of electroluminescent material and device causes world technology circle and the great interest of industrial quarters.OLEDs devices
Part is that have many advantages, such as low energy consumption, wide viewing angle, large area, the flat panel display that soft screen can be achieved, and is generally considered next
The ideal display screen that generation can replace the displays such as liquid crystal LCD, inorganic LED, can be used in mobile phone, colour TV etc., in solid-state lighting
Tempting foreground is shown in terms of FPD.
Carrier transmission material, luminescent material, electrode material and the device that the particular advantages of OLEDs devices are used with device
The structure of part has close relationship, and wherein luminescent material is the core component of OLEDs devices.Wherein due to Ir (III) complex
It is a kind of typical MLCT emitting complexes, the thermal stability having had, relatively short lifetime of excited state, high luminous efficiency,
And luminescent color easily adjust etc. various advantages and as electroluminescent material field research hotspot.
It is well known that the hole mobility of cavitation layer is far longer than the electron mobility of electronic shell, this may result in current-carrying
The imbalance of son reduces device efficiency.Therefore, if the complex of iridium luminescent material of exploitation has good electron-transporting
Can, Carrier composite can be widened with the transmission of equilbrium carrier, improve device efficiency, the performance for improving device has
Important research significance.In addition, the synthetic yield and sublimation purification yield for the material of practical application its complex are for drop
The manufacturing cost of low material and device is most important.Therefore, it is necessary to provide it is a kind of and meanwhile have electron mobility is high, synthesize and
Distil the high complex of iridium luminescent material of yield.
Invention content
The present invention is in view of the shortcomings of the prior art, devise a kind of miscellaneous containing the main ligand of azacyclo- and thiobis diaryl/virtue
The material is simultaneously applied in organic electroluminescence device by the novel complex of iridium of base phosphorimide assistant ligand.It is of the present invention
The main ligand of azacyclo- of complex of iridium can effectively improve the electron mobility of complex, and due to the radius ratio of sulphur atom S
Oxygen is big, is easily deformed, stronger than oxygen with the coordination ability of iridium atom, has significantly for the synthesis and distillation yield that improve complex
Raising acts on.
Specific technical solution of the present invention is as follows：
A kind of complex of iridium, with the azacyclo- of C^N structures for main ligand, with thiobis diaryl/heterocyclic base phosphorimide
For assistant ligand, the complex of iridium structure is as follows：
Wherein common any C^N in the complex of iridium material of various luminescent colors at present may be used in the main ligand of azacyclo-
The ligand of structure,The middle group being coordinated with C sections is substituted or non-substituted phenyl, pyridyl group, thienyl or pyrimidine radicals；N sections
The group of coordination is substituted or non-substituted pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, thiazolyl, imidazole radicals, quinolyl, different
Quinolyl, quinazolyl or pteridyl；
R represents substituted or non-substituted aryl/heterocyclic base, the aryl/heterocyclic base be selected from phenyl, pyridyl group, pyrimidine radicals,
Furyl or thienyl, it is preferred that the arbitrary position of aryl/heterocyclic base is by the alkyl of H, C1-C6, the halogen of C1-C6 alkoxies, C1-C6
Replaced for alkyl, halogen, preferred R is represented
The preferred embodiment of the present invention, the thiobis diaryl/heterocyclic base phosphorimide are selected from
Complex of iridium of the present invention, the groups of the main ligand C sections of coordinations of the azacyclo- can be selected from arbitrary position by H,
In the alkyl of C1-C6, C1-C6 alkoxies, the halohydrocarbyl of C1-C6, halogen, cyano, aniline, carbazole, oxadiazoles
Phenyl, pyridyl group, thienyl or the pyrimidine radicals of one or more substitution.It is preferred that arbitrary position is by H, methyl, methoxyl group, tertiary fourth
Phenyl, pyridyl group, the thienyl of one or more of base, fluorine, trifluoromethyl, cyano, aniline, carbazole, oxadiazoles substitution
Or pyrimidine radicals.It is furthermore preferred that the group of the main ligand C sections of coordinations of azacyclo- is selected from
The group of complex of iridium of the present invention, the main ligand N sections of coordinations of azacyclo- is selected from arbitrary position by H, C1-C6
Alkyl, the halohydrocarbyl of C1-C6, the pyridyl group of one or more of halogen substitution, pyrimidine radicals, pyridazinyl, three
Piperazine base, thiazolyl, imidazole radicals, quinolyl, isoquinolyl, quinazolyl or pteridyl.It is preferred that arbitrary position by H, methyl, fluorine,
Pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, thiazolyl, imidazole radicals, quinolyl, isoquinolyl, the quinoline of trifluoromethyl substitution
Oxazoline base or pteridyl.It is furthermore preferred that the group of the main ligand N sections of coordinations of azacyclo- is selected from
The preferred technical solution of the present invention, the main ligand of azacyclo- are selected from
The preferred technical solution of the present invention, the complex of iridium are selected from：
Thiobis diaryl/heterocyclic base phosphorimide of the present invention is commercially available, or prepares with the following method
It obtains：Then and tri-chlorination grignard reagent is obtained by the reaction in the heteroaromatic compounds and magnesium powder of bromo aromatic compound or bromo,
Phosphorus reaction is evaporated under reduced pressure out diaryl/heterocyclic base chlorination phosphorus derivant, and is further reacted with two alkanamine of hexamethyl silicon, through column
Chromatography is aoxidized to obtain product under anaerobic with sulphur powder in tetrahydrofuran.The aromatic compound, heteroaromatic definition
As it was noted above, can be arbitrary position by the alkyl of H, C1-C6, C1-C6 alkoxies, the halohydrocarbyl of C1-C6, halogen institute
Substituted benzene, pyridine, pyrimidine, furans or thiophene.
Complex of iridium of the present invention can be used conventional method and prepare, for example, by main ligand and IrCl3With 2:1
Ratio flows back 10 hours in ethoxy ethanol solution, and cold filtration obtains the chlorine bridge complex of iridium；Then the chlorine bridge cooperation of iridium
Object and thiobis diaryl/heterocyclic base phosphorimide and potassium hydroxide are with 1:2 ratio flows back two small in ethoxy ethanol
When obtain the crude product of complex of iridium, column chromatography obtains sterling, and further sublimation purification obtains meeting system under vacuum
The luminescent material of standby requirement on devices.
Another object of the present invention is to provide complex of iridium of the present invention in preparing organic electroluminescence device
Application.Complex of iridium of the present invention can be used for preparing organic electroluminescence device, for example, organic electroluminescence device packet
Include substrate, anode, hole-injecting material, hole transmission layer, organic luminous layer, electron transfer layer, electron injection material and cathode.
Substrate is glass, and anode is indium tin oxygen, 2,3,6,7,10,11- six cyano of hole injection layer-Isosorbide-5-Nitrae, 5,8,9,12- six azepines
Benzophenanthrene HAT-CN, cavitation layer use 4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyls) aniline TAPC materials, electron-transport
It is metal Al that layer, which uses 1,3,5- tri- [(3- pyridyl groups) -3- phenyl] benzene TmPyPb, electron injection material LiF, cathode,；It is organic
Luminescent layer includes material of main part and luminescent material, and the material of main part is 4,4 ', 4, and "-three (9- carbazyls) triphenylamine TCTA are sent out
Luminescent material is complex of iridium of the present invention.
Beneficial effects of the present invention：Complex of iridium provided by the invention has electron mobility height, is easily-synthesized, chemical property
The characteristics of stable, easy sublimation purification.The preparation method of the material is simple, and yield is higher.Due to azacyclo- and phosphorus sulfide linkage
Introduce, the comprehensive photoelectric properties of material can Effective Regulation, for obtain efficient organic electroluminescence device and its illumination with
The application of display field is provided convenience.
The azacyclo- and phosphorus methylthio group of complex of iridium intramolecular of the present invention are all good electron transporting groups, they
Introducing help to improve material electron mobility and regulation and control luminescent color.To balance injection and the biography in hole and electronics
It is defeated, widen the recombination region of carrier, promote device efficiency, reduce efficiency roll-off, as in the present invention with complex of iridium Stpip 1
For device prepared by the centre of luminescence, performance is far superior to non-thiobis diaryl/heterocyclic base phosphorimide assistant ligand iridium
Complex is the device performance of centre of luminescence preparation [referring to document：Yu-Cheng Zhu,Liang Zhou,Hong-Yan Li,
Qiu-Lei Xu,Ming-Yu Teng,You-Xuan Zheng,Jing-Lin Zuo,Hong-Jie Zhang,Xiao-Zeng
You,Highly Efficient Green and Blue-Green Phosphorescent OLEDs Based on
Iridium Complexes with the Tetraphenylimidodiphosphinate Ligand,Adv.Mater.,
2011,23,4041–4046].And since the radius ratio oxygen of sulphur atom is big, morphotropism is big and the combination of transition metal iridium more
What is added is secured, synthetic yield and vacuum sublimation yield higher.The synthetic yield of complex of iridium as described in the present invention is generally all
Higher than 90%, vacuum sublimation rate also above 90%, significantly larger than at present most complex of iridium synthetic yield (<And vacuum 70%)
Sublimation rate (<60%), it is very suitable for industrialization production.
Description of the drawings
Fig. 1 is the electroluminescent spectrum that complex of iridium Stpip 1 of the present invention is used for organic electroluminescence device.
Fig. 2 is brightness and voltage curve of the complex of iridium Stpip 1 of the present invention for organic electroluminescence device.
Fig. 3 is current efficiency and brightness of the complex of iridium Stpip 1 provided by the invention for organic electroluminescence device
Curve.
Specific implementation mode
Illustrate the specific steps of the present invention by the following examples, but is not limited by the example.
Term as used in the present invention generally there are those of ordinary skill in the art usually to manage unless otherwise indicated
The meaning of solution.
The present invention is described in further detail with reference to specific embodiment and with reference to data.It should be understood that the embodiment is
In order to demonstrate the invention, it rather than limits the scope of the invention in any way.
In the examples below, the various processes and method not being described in detail are conventional methods as known in the art.
With reference to specific embodiment, the present invention is further described.
The preparation of 1 assistant ligand thiobis diaryl of embodiment/heterocyclic base phosphorimide
Grignard reagent is obtained by the reaction in bromobenzene and magnesium powder, is then reacted with phosphorus trichloride, is evaporated under reduced pressure out diphenyl chlorination
Phosphorus derivant, and further reacted with two alkanamine of hexamethyl silicon, through column chromatography for separation, then under anaerobic in tetrahydrofuran
It is middle to be aoxidized to obtain thiobis diphenylphosphine acid imide with sulphur powder
Other thiobis diaryl/heterocyclic base phosphorimides can be made using the above method：
The preparation of 2 complex of iridium of the present invention of embodiment
By main ligand 2- phenylpyridines and IrCl3With 2:1 ratio flows back 10 hours in ethoxy ethanol solution, cooling
The chlorine bridge complex of iridium is obtained by filtration；Then the chlorine bridge complex of 10mmol (10.72 grams) and 20mmol's (8.99 grams) is thio
The potassium hydroxide of double diphenylphosphine acid imide assistant ligands and 20mmol (1.12 grams) flow back two hours in ethoxy ethanol
The crude product of complex of iridium is obtained, column chromatography obtains 17.28 grams of 1 (yields of sterling Stpip：91%)
Further 5 grams of Stpip 1 are placed in quartz ampoule, 10-5Pa heated under vacuum sublimation purification obtains 4.5
Gram meet prepare requirement on devices luminescent material (sublimation rate 90%).Reaction is as follows：
Gained complex of iridium Stpip 1 is analyzed as follows by nuclear magnetic resonance spectroscopy and high resolution mass spectrum：
1H NMR(400MHz,CDCl3) δ 8.56 (d, J=8.2Hz, 2H), 8.16 (t, J=7.4Hz, 2H), 7.82 (d, J
=4.3Hz, 2H), 7.52-7.24 (m, 28H), 6.95 (d, J=4.7Hz, 2H)
HRMS(ESI)m/z calcd for C46H36IrN3P2S2[M+H]:949.1455,found:949.1453.
With reference to the above method, different main ligands is selected： And implementation
Following compound is made in thiobis diaryl made from example 1/heterocyclic base phosphorimide reaction：
The preparation of 3 complex of iridium Stpip of embodiment, 1 organic electroluminescence devices
For the centre of luminescence using Stpip 1 as luminescent layer prepares organic electroluminescence device below, illustrate the present invention
The preparation of organic electroluminescence device.The structure of OLEDs devices includes：Substrate, anode, hole-injecting material, hole transmission layer,
Organic luminous layer, electron transfer layer, electron injection material and cathode.The substrate is glass, and anode is indium tin oxygen, hole injection
Layer is 2,3,6,7,10,11- six cyano-Isosorbide-5-Nitrae, and 5,8,9,12- six azepine benzophenanthrene HAT-CN (5nm), evaporation rate is
0.05nm/s；Cavitation layer is using 4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyls) aniline TAPC materials (50nm), vapor deposition speed
Rate is 0.05nm/s；Electron transfer layer uses 1,3,5- tri- [(3- pyridyl groups) -3- phenyl] benzene TmPyPb (50nm), evaporation rate
For 0.05nm/s；Electron injection material is LiF (1nm), evaporation rate 0.01nm/s；Cathode is metal Al (100nm), vapor deposition
Rate is 0.2nm/s；The organic luminous layer uses doped structure, thickness 40nm, including material of main part and luminescent material, institute
It is with 4,4 ', 4 to state material of main part, and "-three (9- carbazyls) triphenylamine TCTA, luminescent material are complex of iridium, complex of iridium quality
Score 8wt%.
Different materials structure in the present invention is as follows：
The present invention selects a kind of new complex of iridium Stpip 1 to prepare organic electroluminescence device for the centre of luminescence.It please one
And refering to fig. 1, Fig. 2 and Fig. 3, Fig. 1 be electroluminescent light that Stpip 1 provided by the invention is used for organic electroluminescence device
Spectrum, Fig. 2 and Fig. 3 are the photoelectric properties that Stpip 1 provided by the invention is used for organic electroluminescence device.Such as Fig. 2 and Fig. 3 institutes
Show, the startup voltage of the organic electroluminescence device is 3.1V, and maximum current efficiency is 91cd/A, in 1000cd/m2's
Current efficiency still may remain in 83.30cd/A when brightness, it is shown that very small efficiency roll-off.Its performance is far superior to existing
There is the device performance that technology is prepared using non-thiobis diaryl/heterocyclic base phosphorimide assistant ligand complex of iridium as the centre of luminescence
[maximum current efficiency is 67.95cd/A, in 1000cd/m2Brightness when current efficiency be 52.74cd/A, referring to document：Yu-
Cheng Zhu,Liang Zhou,Hong-Yan Li,Qiu-Lei Xu,Ming-Yu Teng,You-Xuan Zheng,Jing-
Lin Zuo,Hong-Jie Zhang,Xiao-Zeng You,Highly Efficient Green and Blue-Green
Phosphorescent OLEDs Based on Iridium Complexes with the
Tetraphenylimidodiphosphinate Ligand,Adv.Mater.,2011,23,4041–4046].By studying light
Physical property shows that this kind of complex of iridium containing the main ligand of azacyclo- and thiobis diphenylphosphine acid imide assistant ligand shines
Material has higher device efficiency, has actual application value in the fields such as display and illumination.
The complex of iridium Stpip 2-75 that the embodiment of the present invention 2 is prepared can be used the above method and organic electroluminescence hair be made
Optical device has photoelectric properties similar with Stpip 1.
Such complex of iridium provided by the invention can be used as the luminescent layer that luminescent material is applied to OLEDs, excellent by designing
The structure for changing compound, invention achieves the purposes of regulation and control device 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
It encloses.
Claims (10)
1. a kind of complex of iridium, it is characterised in that with the azacyclo- of C^N structures for main ligand, with thiobis diaryl/heterocyclic base
Phosphorimide is assistant ligand, and the complex of iridium structure is as follows：
The wherein main ligand of azacyclo-The middle group being coordinated with C sections is substituted or non-substituted phenyl, pyridyl group, thienyl or phonetic
Piperidinyl；N sections coordination groups be substituted or non-substituted pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, thiazolyl, imidazole radicals,
Quinolyl, isoquinolyl, quinazolyl or pteridyl；
R represents substituted or non-substituted aryl/heterocyclic base, and the aryl/heterocyclic base is selected from phenyl, pyridyl group, pyrimidine radicals, furans
Base or thienyl.
2. complex of iridium as described in claim 1, it is characterised in that the arbitrary position of aryl/heterocyclic base is by the alkane of H, C1-C6
Base, C1-C6 alkoxies, the halohydrocarbyl of C1-C6, halogen are replaced.
3. complex of iridium as described in claim 1, it is characterised in that R is represented
4. complex of iridium as described in claim 1, it is characterised in that the group of the main ligand C sections of coordinations of azacyclo-, which is selected from, appoints
Position anticipate by the alkyl of H, C1-C6, C1-C6 alkoxies, the halohydrocarbyl of C1-C6, halogen, cyano, aniline, carbazole, Evil bis-
Phenyl, pyridyl group, thienyl or the pyrimidine radicals of one or more of azoles substitution.
5. complex of iridium as claimed in claim 4, it is characterised in that the group of the main ligand C sections of coordinations of azacyclo- is selected from
6. complex of iridium as described in claim 1, it is characterised in that the group of the main ligand N sections of coordinations of azacyclo-, which is selected from, appoints
Meaning position is replaced by one or more of the alkyl of H, C1-C6, C1-C6 alkoxies, the halohydrocarbyl of C1-C6, halogen
Pyridyl group, pyrimidine radicals, pyridazinyl, triazine radical, thiazolyl, imidazole radicals, quinolyl, isoquinolyl, quinazolyl or pteridyl.
7. complex of iridium as claimed in claim 6, it is characterised in that the group of the main ligand N sections of coordinations of azacyclo- is selected from
8. complex of iridium as described in claim 1, it is characterised in that the main ligand of azacyclo- is selected from
9. complex of iridium as described in claim 1, it is characterised in that the complex of iridium is selected from：
10. if claim 1-9 any one of them complex of iridium is in the application in preparing organic electroluminescence device.
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