CN108690092A - One kind is used as transient metal complex, preparation method and the application of phosphor material - Google Patents
One kind is used as transient metal complex, preparation method and the application of phosphor material Download PDFInfo
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- CN108690092A CN108690092A CN201810778928.0A CN201810778928A CN108690092A CN 108690092 A CN108690092 A CN 108690092A CN 201810778928 A CN201810778928 A CN 201810778928A CN 108690092 A CN108690092 A CN 108690092A
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- 239000000463 material Substances 0.000 title claims abstract description 33
- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 23
- 230000001052 transient effect Effects 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000003446 ligand Substances 0.000 claims abstract description 36
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- -1 aliphatic radical Chemical class 0.000 claims description 62
- 239000010410 layer Substances 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 16
- 229910000077 silane Inorganic materials 0.000 claims description 16
- 238000006884 silylation reaction Methods 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 14
- 150000001491 aromatic compounds Chemical class 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052723 transition metal Inorganic materials 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000005013 aryl ether group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 239000003205 fragrance Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229930192474 thiophene Natural products 0.000 claims description 8
- 150000003624 transition metals Chemical group 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- 238000005401 electroluminescence Methods 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 150000005360 2-phenylpyridines Chemical class 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N Heptanedioic acid Natural products OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 239000003086 colorant Substances 0.000 abstract description 5
- 230000008859 change Effects 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- PMNPSCJVKKSJSG-UHFFFAOYSA-N 1,1-diphenyl-2,3-di(propan-2-yl)guanidine Chemical class C=1C=CC=CC=1N(C(=NC(C)C)NC(C)C)C1=CC=CC=C1 PMNPSCJVKKSJSG-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical group C1=CC=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC(=CC=C1C1=CC=C(C=C13)N(C=1C=CC=CC=1)C=1C=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MQRCTQVBZYBPQE-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- YMHFIWZRDQFZLW-UHFFFAOYSA-N CC1=C(C(C=CC1=O)=O)C.N#CC#N Chemical class CC1=C(C(C=CC1=O)=O)C.N#CC#N YMHFIWZRDQFZLW-UHFFFAOYSA-N 0.000 description 1
- 0 CCC1C(****)N(*C[*@](*=**)I)C(CC)(CC)N(C(C)C)C1*C Chemical compound CCC1C(****)N(*C[*@](*=**)I)C(CC)(CC)N(C(C)C)C1*C 0.000 description 1
- YOOWJTSNIZYWCT-UHFFFAOYSA-N [Ir]#P Chemical compound [Ir]#P YOOWJTSNIZYWCT-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic 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
- 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
- C07F15/006—Palladium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
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- 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
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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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
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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
- H10K85/30—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
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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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- 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
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to organic photoelectrical material technical fields, more particularly to a kind of transient metal complex, preparation method and application for being used as phosphor material.The present invention passes through Z1And Z2Collocation, the wavelength of transmitted light of material can be adjusted in larger wave-length coverage, while the wavelength of transmitting light further can be precisely adjusted by changing the hetero atom on main ligand, there is the predictable electroluminescent material of luminescent color to obtain;The main ligand skeleton structure having the same of the present invention, only position and type of the position and hetero atom of change functional group on main ligand can be realized wavelength of transmitted light and adjusted on a large scale from green light to dark red light;Complex luminous efficiency produced by the present invention is high, and the preparation method of different colours luminescent material is essentially identical, easy to operate.
Description
Technical field
The invention belongs to organic photoelectrical material technical fields, more particularly to a kind of Transition metal complexes for being used as phosphor material
Object, preparation method and application.
Background technology
Organic electroluminescent phenomenon document is reported in 1963 earliest, because its high voltage and low luminous efficiency are not affected by weight
Depending on.Until 1987, there is OLED (Organic Light Emitting Diode, the English name Organic Light- of multilayer architecture in report
Emitting Diode, abbreviation OLED) device.Compared to traditional light emitting diode (LED) and liquid crystal display (LCD), OLED
With self-luminous, clear beautiful, frivolous, fast response time, visual angle is wide, low-power consumption, Applicable temperature range is big, manufacturing process is simple
The features such as.Meet " light, thin, small, color, province, beautiful, diversification " characteristic needed for portable flat-panel monitor.In addition, OLED may be used also
For normal lighting, the characteristics of due to its area source, application prospect is boundless.It is various in addition to may be used as in terms of illumination
Gorgeous monochromatic illumination, can also be achieved white-light illuminating.RGB three-color arrangements may be used in white-light illuminating, and blue light-yellow light can also be used
Two color schemes are realized.The OLED luminescent materials of different colours play an important role the application of OLED device.
It is such as high largely studies have shown that transient metal complex has unique advantage as electroluminescent organic material
Efficiency, illuminant colour covering surface are wide etc..Due to the Rapid Popularization that OLED is shown, blue, green and red illuminating material are currently to grind
The hot spot studied carefully.Green luminescent material has basically reached practical requirement, and red light material efficiency is slightly inadequate.In addition, OLED shines
In terms of bright and monochromatic display, the luminescent material of other colors is needed, such as between Neutral colour blue, green, between red trichromatism.Mesh
Before, the concern in terms of material development is fewer.In general, in order to change the color that light occurs, it can be in the ligand of luminescent material
Upper plus electron-donating group and electron-withdrawing group adjust the color of transmitting light, but this scheme to the adjusting range of color compared with
It is small.The adjustment transmitting light color on a large scale under a kind of ligand structure, the transmitting luminescent material that can be not only needed can be with
The synthesis complexity problem for reducing different colours luminescent material, is also of great significance for large-scale industrial production.
Invention content
The present invention provides a kind of transition metal for being used as phosphor material for existing above-mentioned the shortcomings of the prior art
Complex, preparation method and application.
The technical solution that the present invention solves above-mentioned technical problem is as follows:One kind is used as the Transition metal complexes of phosphor material
Object, which is characterized in that its structural formula is as follows:
Wherein, X1,X2Separate is N, C or B;
Y1,Y2,Y3,Y4,Y5,Y6,Y7,Y8Separate is N or CR1, wherein R1For hydrogen, deuterium, halogen replaces or does not take
The aryl in generation, arlydene, heteroaryl, inferior heteroaryl, benzheterocycle aryl, polyheteroaromatic, benzheterocycle aliphatic radical, fragrant amino,
Arylthio, sub- arylthio, aryl ether group, aryl alkyl dialkyiarylsilyl, adamantane, diarye silyl, fragrance
Compound and its fragrance derivatives, alkyl, silylation, naphthenic base, cycloalkylidene, Heterocyclylalkyl, sub- Heterocyclylalkyl, two cycloalkanes
Base, trialkylsilkl, alkenyl, alkenylene, alkynyl, alkynyl, heterocycle aliphatic radical, phosphinothioyl, phosphinyl, triazine radical, triazolyl,
Morpholinyl, thio-morpholinyl, alkoxy, alkylene oxide group, alkylthio group, alkylenethio, alkylamino, benzenesulfonyl, quinoline sulfonyl,
Benzoyl, diazanyl, ester group, alkyl-carbonyl, alkoxy carbonyl, alkyl amino-carbonyl, silylation carbonyl, alkoxy silane, alkane sulphur
Base silane, acetylpyridine, fluorenes, polycyclc aromatic compound, carbazole, thiophene, hydroxyl, carboxyl, nitro or CF3In it is arbitrary
It is a kind of;
Z1And Z2For carbonyl, O, S, NR2Or CR3R4;Z1And Z2One of them is carbonyl, another is not carbonyl;R2,R3With
R4Separate is hydrogen, deuterium, halogen, substituted or unsubstituted aryl, arlydene, heteroaryl, inferior heteroaryl, benzheterocycle virtue
Base, polyheteroaromatic, benzheterocycle aliphatic radical, fragrant amino, arylthio, sub- arylthio, aryl ether group, aryl alkyl, di alkylaryl
Silicyl, adamantane, diarye silyl, aromatic compound and its fragrance derivatives, alkyl, silylation naphthenic base, Asia
It is naphthenic base, Heterocyclylalkyl, sub- Heterocyclylalkyl, bicyclic alkyl, trialkylsilkl, alkenyl, alkenylene, alkynyl, alkynylene, miscellaneous
Cycloaliphatic radical, phosphinothioyl, phosphinyl, triazine radical, triazolyl, morpholinyl, thio-morpholinyl, alkoxy, alkylene oxide group, alkylthio group,
Alkylenethio, alkylamino, benzenesulfonyl, quinoline sulfonyl, benzoyl, diazanyl, ester group, alkyl-carbonyl, alkoxy carbonyl, alkane
Amino carbonyl, silylation carbonyl, alkoxy silane, alkylthio group silane, acetylpyridine, fluorenes, polycyclc aromatic compound, click
Azoles, thiophene, hydroxyl, carboxyl, nitro or CF3In any one;
M is transition metal Ir, Pd or Pt;
(L^Z) it is assistant ligand, is that the main ligand in left side in bidentate ligand, with structure above is identical or different;
m>0, and m is integer;N >=0, and n is integer.
Further, Y1, Y2,Y3,Y4,Y5,Y6,Y7,Y8,Z1And Z2Two groups of arbitrary neighborhood connect to form cyclic group.
Further, it includes one or more hetero atom that two groups of arbitrary neighborhood, which connect the cyclic group to be formed,.
Further, Y4And Y5Pass through-(Y)xAbutment connection, the Y be O, S, Se, CR5,NR6, carbonyl or AR7R8;1
≤ x≤50, and be integer;X Y is mutual indepedent;
Wherein, A C, Si or Ge;R5,R6,R7,R8It is separate be hydrogen, deuterium, halogen, substituted or unsubstituted aryl,
Arlydene, inferior heteroaryl, heteroaryl, benzheterocycle aryl, polyheteroaromatic, benzheterocycle aliphatic radical, fragrant amino, arylthio, Asia
Arylthio, aryl ether group, aryl alkyl, dialkyiarylsilyl, adamantane, diarye silyl, aromatic compound and
Its fragrance derivatives, alkyl, silylation, naphthenic base, cycloalkylidene, Heterocyclylalkyl, sub- Heterocyclylalkyl, bicyclic alkyl, trialkyl
Silicyl, alkenyl, alkenylene, alkynyl, alkynylene, heterocycle aliphatic radical, phosphinothioyl, phosphinyl, triazine radical, triazolyl, morpholinyl,
Thio-morpholinyl, alkoxy, alkylene oxide group, alkylthio group, alkylenethio, alkylamino, benzenesulfonyl, quinoline sulfonyl, benzoyl
Base, diazanyl, ester group, alkyl-carbonyl, alkoxy carbonyl, alkyl amino-carbonyl, silylation carbonyl, alkoxy silane, alkylthio group silane,
Acetylpyridine, fluorenes, polycyclc aromatic compound, carbazole, thiophene, hydroxyl, carboxyl, nitro or CF3In any one.
Further, between main ligand or between main ligand and assistant ligand directly by be covalently keyed or by-
(W)zAbutment connect into tetradentate ligands or sexadentate ligand;The W is O, S, Se, CR9,NR10,DR11R12, carbonyl, substitution
Or non-substituted aromatic radical, substituted or non-substituted heteroaryl or naphthenic base, 1≤z≤50, and be integer;Z W is mutual indepedent;
Wherein, D C, Si or Ge;R9,R10,R11,R12Separate is hydrogen, deuterium, and halogen is substituted or unsubstituted
Aryl, arlydene, inferior heteroaryl, heteroaryl, benzheterocycle aryl, polyheteroaromatic, benzheterocycle aliphatic radical, fragrant amino, fragrant sulphur
Base, sub- arylthio, aryl ether group, aryl alkyl, dialkyiarylsilyl, adamantane, diarye silyl, aromatics
Object and its fragrance derivatives, alkyl, silylation, naphthenic base, cycloalkylidene, Heterocyclylalkyl, sub- Heterocyclylalkyl, bicyclic alkyl, three
AIkylsilyl groups, alkenyl, alkenylene, alkynyl, alkynylene, heterocycle aliphatic radical, phosphinothioyl, phosphinyl, triazine radical, triazolyl,
Quinoline base, thio-morpholinyl, alkoxy, alkylene oxide group, alkylthio group, alkylenethio, alkylamino, benzenesulfonyl, quinoline sulfonyl, benzene
Formoxyl, diazanyl, ester group, alkyl-carbonyl, alkoxy carbonyl, alkyl amino-carbonyl, silylation carbonyl, alkoxy silane, alkylthio group
Silane, acetylpyridine, fluorenes, polycyclc aromatic compound, carbazole, thiophene, hydroxyl, carboxyl, nitro or CF3In it is any one
Kind.
Further, the assistant ligand (L^Z) is acetylacetone,2,4-pentanedione, 2- pyridine carboxylic acids, 2- phenylpyridines, 2,2,6,6- tetra-
Methyl -3,5- pimelic acid, (E)-N, N'Diisopropyl benzenecarboximidamide, (Z) -2,3- diisopropyl -1,1- diphenylguanidines or 2,8- bis-
Any one in methyl -4,6- nonyl diketone.
Preferably, the transient metal complex, structural formula are:
Second object of the present invention is to provide the preparation method of above-mentioned transient metal complex, and steps are as follows:
1) under nitrogen protection, main ligand is dissolved in ethylene glycol monoethyl ether, the salt and deionized water of transition metal is added,
Transition metal chlorine bridge complex is obtained by the reaction in heating;
2) it under alkaline condition, by transition metal chlorine bridge complex and assistant ligand (L^Z) heating reflux reaction, obtained
Cross metal complex;
The assistant ligand (L^Z) is bidentate ligand, identical as the main ligand in left side in structure above, Huo Zhewei
Acetylacetone,2,4-pentanedione, 2- pyridine carboxylic acids, 2- phenylpyridines, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'Diisopropyl benzene
Any one in carbonamidine, (Z) -2,3- diisopropyl -1,1- diphenylguanidines, 2,8- dimethyl -4,6- nonyl diketone.
Third object of the present invention is to provide the transient metal complex as electroluminescent material, in Organic Electricity
Application in electroluminescence device.
The present invention is also claimed the organic electroluminescence device using above-mentioned transient metal complex, including anode layer,
Cathode layer and the functional layer between anode layer, cathode layer include transient metal complex above-mentioned in functional layer.
Further, the functional layer is luminescent layer, and luminescent layer includes main body luminescent material and guest emitting material, the present invention
The transient metal complex of offer is as guest emitting material.
The beneficial effects of the invention are as follows:The present invention passes through Z1And Z2Collocation, material can be adjusted in larger wave-length coverage
Wavelength of transmitted light, while the wavelength of transmitting light further can be precisely adjusted by changing the hetero atom on main ligand, to obtain
With the predictable electroluminescent material of luminescent color;The main ligand skeleton structure having the same of the present invention, only changes function
Wavelength of transmitted light can be realized from green light to dark red wide range in position and type of the position and hetero atom of group on main ligand
Adjusting;Complex luminous efficiency produced by the present invention is high, and the preparation method of different colours luminescent material is essentially identical, operation letter
It is single.
Description of the drawings
Fig. 1 is the OLED structure schematic diagram of electroluminescent organic material;
Fig. 2 is the emission spectroanalysis figure of application examples 1-3;
In figure, 1, glass substrate;2, anode layer;3, hole injection layer;4, hole transmission layer;5, luminescent layer;6, electronics passes
Defeated layer;7, electron injecting layer;8, cathode layer.
Specific implementation mode
Below in conjunction with example, present invention is described, and the given examples are served only to explain the present invention, is not intended to limit this
The range of invention.
Embodiment 1
The synthesis of complex of iridium Ir12, reaction equation are as follows:
(1) chlorine bridge dimer is synthesized
(2) object synthesizes
Embodiment 2
The synthesis of complex of iridium Ir10, reaction equation are as follows:
(1) chlorine bridge dimer is synthesized
(2) object synthesizes
Embodiment 3
The synthesis of complex of iridium Ir7, reaction equation are as follows:
(1) chlorine bridge dimer is synthesized
(2) object synthesizes
The transition metal that complex prepared by embodiment 1-3 is related to can also be prepared using Ir as representative using Pd or Pt
Metal complex is crossed, reaction principle and technique are identical as Ir.
As shown in Figure 1, the structure of organic electroluminescence device (OLED) includes the glass substrate 1 for stacking gradually combination, sun
Pole layer 2, hole injection layer 3, hole transmission layer 4, luminescent layer 5, electron transfer layer 6, electron injecting layer 7 and cathode layer 8.This is sent out
Bright iridium phosphor material obtained is applied in the luminescent layer of OLED, each composition of layer compositions of the OLED that table 1 is application examples 1-3.
Each composition of layer compositions of OLED of 1. application examples 1-3 of table
Application examples 1
The tin indium oxide (ITO) that a layer thickness is 100nm is deposited on glass bottom liner 1 is used as transparent anode layer 2;Transparent
Vacuum evaporation thickness is NPB (N, N '-two (1- naphthalenes)-N, the N '-diphenyl -1,1 '-biphenyl -4-4 '-of 10nm on anode layer 2
Diamines) hole mobile material as hole injection layer 3, wherein doping mass ratio 3% F4-TCNQ (2,3,5,6- tetra- fluoro- 7,
7',8,8'- four cyanogen dimethyl-parabenzoquinones);It is spiro-TAD (the 2,2&apos that a layer thickness is 100nm on hole injection layer 3;,7,
7'- four (diphenyl amino) -9,9'Spiro-bisfluorene) it is used as hole transmission layer 4;Vacuum evaporation a layer thickness on hole transmission layer 4
For the TRZ (2,4,6- tri- (9- carbazyls) -1,3,5-triazines) of 40nm, as luminescent layer 5, wherein coordinating doped with 6wt% iridium
Object Ir12;Vacuum evaporation a layer thickness is TPQ (2,3,5,8- tetraphenyls quinoxaline) conduct of 30nm successively on luminescent layer 5 again
Electron transfer layer 6, the Liq that thickness is 1nm are finally heavy using vacuum evaporation coating on electron injecting layer 7 as electron injecting layer 7
Product technology deposition thickness is cathode layer 8 of the metallic aluminium (Al) of 100nm as device.
Know through performance test, the maximum luminous wavelength of the electroluminescent spectrum of the device is located at 617nm, maximum current effect
Rate is 32cd/A, and maximum external quantum efficiency is 13%.
Application examples 2
It is identical as application examples 1, with application examples 1 the difference is that:Luminescent layer 5 is the TRZ (2,4,6- tri- of thickness 40nm
(9- carbazyls) -1,3,5-triazines), wherein doped with 6wt% complex of iridium Ir10.
Know through performance test, the maximum luminous wavelength of the electroluminescent spectrum of the device is located at 670nm, maximum current effect
Rate is 39cd/A, and maximum external quantum efficiency is 15%.
Application examples 3
It is identical as application examples 1, with application examples 1 the difference is that:Luminescent layer 5 is the TRZ (2,4,6- tri- of thickness 40nm
(9- carbazyls) -1,3,5-triazines), wherein doped with 6wt% complex of iridium Ir7.
Know through performance test, the maximum luminous wavelength of the electroluminescent spectrum of the device is located at 635nm, maximum current effect
Rate is 35d/A, and maximum external quantum efficiency is 14%.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention.
Claims (10)
1. one kind is used as the transient metal complex of phosphor material, which is characterized in that its structural formula is as follows:
Wherein, X1,X2Separate is N, C or B;
Y1,Y2,Y3,Y4,Y5,Y6,Y7,Y8Separate is N or CR1, wherein R1For hydrogen, deuterium, halogen, substituted or unsubstituted virtue
Base, arlydene, heteroaryl, inferior heteroaryl, benzheterocycle aryl, polyheteroaromatic, benzheterocycle aliphatic radical, fragrant amino, arylthio,
Sub- arylthio, aryl ether group, aryl alkyl dialkyiarylsilyl, adamantane, diarye silyl, aromatic compound and
Its fragrance derivatives, alkyl, silylation, naphthenic base, cycloalkylidene, Heterocyclylalkyl, sub- Heterocyclylalkyl, bicyclic alkyl, trialkyl
Silicyl, alkenyl, alkenylene, alkynyl, alkynyl, heterocycle aliphatic radical, phosphinothioyl, phosphinyl, triazine radical, triazolyl, morpholinyl, sulphur
For morpholinyl, alkoxy, alkylene oxide group, alkylthio group, alkylenethio, alkylamino, benzenesulfonyl, quinoline sulfonyl, benzoyl,
Diazanyl, ester group, alkyl-carbonyl, alkoxy carbonyl, alkyl amino-carbonyl, silylation carbonyl, alkoxy silane, alkylthio group silane, second
Acyl pyridine, fluorenes, polycyclc aromatic compound, carbazole, thiophene, hydroxyl, carboxyl, nitro or CF3In any one;
Z1And Z2For carbonyl, O, S, NR2Or CR3R4;Z1And Z2One of them is carbonyl, another is not carbonyl;R2,R3And R4Respectively
It is independently hydrogen, deuterium, halogen is substituted or unsubstituted aryl, arlydene, heteroaryl, inferior heteroaryl, benzheterocycle aryl, more
Ring heteroaryl, benzheterocycle aliphatic radical, fragrant amino, arylthio, sub- arylthio, aryl ether group, aryl alkyl, di alkylaryl monosilane
Base, adamantane, diarye silyl, aromatic compound and its fragrance derivatives, alkyl, silylation naphthenic base, cycloalkylidene,
Heterocyclylalkyl, sub- Heterocyclylalkyl, bicyclic alkyl, trialkylsilkl, alkenyl, alkenylene, alkynyl, alkynylene, heterocycle aliphatic radical,
Phosphinothioyl, phosphinyl, triazine radical, triazolyl, morpholinyl, thio-morpholinyl, alkoxy, alkylene oxide group, alkylthio group, alkylene sulphur
Base, alkylamino, benzenesulfonyl, quinoline sulfonyl, benzoyl, diazanyl, ester group, alkyl-carbonyl, alkoxy carbonyl, alkylamino carbonyl
Base, silylation carbonyl, alkoxy silane, alkylthio group silane, acetylpyridine, fluorenes, polycyclc aromatic compound, carbazole, thiophene
Pheno, hydroxyl, carboxyl, nitro or CF3In any one;
M is transition metal Ir, Pd or Pt;
(L^Z) it is assistant ligand, is that the main ligand in left side in bidentate ligand, with structure above is identical or different;
m>0, and m is integer;N >=0, and n is integer.
2. transient metal complex according to claim 1, which is characterized in that Y1, Y2,Y3,Y4,Y5,Y6,Y7,Y8,Z1With
Z2Two groups of arbitrary neighborhood connect to form cyclic group.
3. transient metal complex according to claim 2, which is characterized in that two groups of arbitrary neighborhood connect to be formed
Cyclic group include one or more hetero atom.
4. transient metal complex according to claim 2, which is characterized in that Y4And Y5Pass through-(Y)xAbutment connection,
The Y is O, S, Se, CR5,NR6, carbonyl or AR7R8;1≤x≤50, and be integer;X Y is mutual indepedent;
Wherein, A C, Si or Ge;R5,R6,R7,R8Separate is hydrogen, deuterium, halogen, substituted or unsubstituted aryl, sub- virtue
Base, inferior heteroaryl, heteroaryl, benzheterocycle aryl, polyheteroaromatic, benzheterocycle aliphatic radical, fragrant amino, arylthio, sub- fragrant sulphur
Base, aryl ether group, aryl alkyl, dialkyiarylsilyl, adamantane, diarye silyl, aromatic compound and its virtue
Fragrant derivative, alkyl, silylation, naphthenic base, cycloalkylidene, Heterocyclylalkyl, sub- Heterocyclylalkyl, bicyclic alkyl, trialkyl first silicon
It is alkyl, alkenyl, alkenylene, alkynyl, alkynylene, heterocycle aliphatic radical, phosphinothioyl, phosphinyl, triazine radical, triazolyl, morpholinyl, thio
Morpholinyl, alkoxy, alkylene oxide group, alkylthio group, alkylenethio, alkylamino, benzenesulfonyl, quinoline sulfonyl, benzoyl, hydrazine
Base, ester group, alkyl-carbonyl, alkoxy carbonyl, alkyl amino-carbonyl, silylation carbonyl, alkoxy silane, alkylthio group silane, acetyl
Pyridine, fluorenes, polycyclc aromatic compound, carbazole, thiophene, hydroxyl, carboxyl, nitro or CF3In any one.
5. transient metal complex according to claim 1, which is characterized in that between main ligand or main ligand with it is auxiliary
It helps between ligand directly by being covalently keyed or by-(W)zAbutment connect into tetradentate ligands or sexadentate ligand;It is described
W be O, S, Se, CR9,NR10,DR11R12, carbonyl, substituted or non-substituted aromatic radical, substituted or non-substituted heteroaryl or cycloalkanes
Base, 1≤z≤50, and be integer;Z W is mutual indepedent;
Wherein, D C, Si or Ge;R9,R10,R11,R12Separate is hydrogen, deuterium, halogen, substituted or unsubstituted aryl,
Arlydene, inferior heteroaryl, heteroaryl, benzheterocycle aryl, polyheteroaromatic, benzheterocycle aliphatic radical, fragrant amino, arylthio, Asia
Arylthio, aryl ether group, aryl alkyl, dialkyiarylsilyl, adamantane, diarye silyl, aromatic compound and
Its fragrance derivatives, alkyl, silylation, naphthenic base, cycloalkylidene, Heterocyclylalkyl, sub- Heterocyclylalkyl, bicyclic alkyl, trialkyl
Silicyl, alkenyl, alkenylene, alkynyl, alkynylene, heterocycle aliphatic radical, phosphinothioyl, phosphinyl, triazine radical, triazolyl, morpholinyl,
Thio-morpholinyl, alkoxy, alkylene oxide group, alkylthio group, alkylenethio, alkylamino, benzenesulfonyl, quinoline sulfonyl, benzoyl
Base, diazanyl, ester group, alkyl-carbonyl, alkoxy carbonyl, alkyl amino-carbonyl, silylation carbonyl, alkoxy silane, alkylthio group silane,
Acetylpyridine, fluorenes, polycyclc aromatic compound, carbazole, thiophene, hydroxyl, carboxyl, nitro or CF3In any one.
6. transient metal complex according to claim 1, which is characterized in that the assistant ligand (L^Z) is acetyl
Acetone, 2- pyridine carboxylic acids, 2- phenylpyridines, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'Diisopropyl benzenecarboximidamide,
(Z) any one in -2,3- diisopropyls -1,1- diphenylguanidines or 2,8- dimethyl -4,6- nonyl diketone.
7. transient metal complex according to claim 1, which is characterized in that its structural formula is:
8. a kind of preparation method of transient metal complex, which is characterized in that steps are as follows:
1) under nitrogen protection, main ligand is dissolved in ethylene glycol monoethyl ether, the salt and deionized water of transition metal is added, is heated
Transition metal chlorine bridge complex is obtained by the reaction;
2) under alkaline condition, by transition metal chlorine bridge complex and assistant ligand (L^Z) heating reflux reaction, transition gold is obtained
Metal complex;
The assistant ligand (L^Z) is bidentate ligand, identical as the main ligand in left side in structure above, or is acetyl
Acetone, 2- pyridine carboxylic acids, 2- phenylpyridines, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'Diisopropyl benzenecarboximidamide,
(Z) any one in -2,3- diisopropyls -1,1- diphenylguanidines, 2,8- dimethyl -4,6- nonyl diketone.
9. a kind of organic electroluminescence device, including anode layer, cathode layer and the functional layer between anode layer, cathode layer,
It is characterized in that, including claim 1~7 any one of them transient metal complex in the functional layer.
10. organic electroluminescence device according to claim 9, which is characterized in that the functional layer is luminescent layer, is shone
Layer includes main body luminescent material and guest emitting material, and the transient metal complex is as guest emitting material.
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| CN114163480A (en) * | 2021-10-26 | 2022-03-11 | 奥来德(上海)光电材料科技有限公司 | Organic iridium metal complex with long service life and high efficiency and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102264864A (en) * | 2008-10-29 | 2011-11-30 | 葛来西雅帝史派有限公司 | Novel compounds for electronic material and organic electronic device using same |
| CN103664898A (en) * | 2012-09-07 | 2014-03-26 | 三星显示有限公司 | Organometallic compound and organic light-emitting device including the same |
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| CN102264864A (en) * | 2008-10-29 | 2011-11-30 | 葛来西雅帝史派有限公司 | Novel compounds for electronic material and organic electronic device using same |
| CN103664898A (en) * | 2012-09-07 | 2014-03-26 | 三星显示有限公司 | Organometallic compound and organic light-emitting device including the same |
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| CN114163480A (en) * | 2021-10-26 | 2022-03-11 | 奥来德(上海)光电材料科技有限公司 | Organic iridium metal complex with long service life and high efficiency and application thereof |
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