CN109111480A - One kind is used as complex of iridium, preparation method and the application of phosphor material - Google Patents
One kind is used as complex of iridium, preparation method and the application of phosphor material Download PDFInfo
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- CN109111480A CN109111480A CN201710487230.9A CN201710487230A CN109111480A CN 109111480 A CN109111480 A CN 109111480A CN 201710487230 A CN201710487230 A CN 201710487230A CN 109111480 A CN109111480 A CN 109111480A
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- iridium
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- deuterium
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 30
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000003446 ligand Substances 0.000 claims abstract description 28
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- -1 Amino, sulfydryl Chemical group 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 238000006884 silylation reaction Methods 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 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
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000008367 deionised water Substances 0.000 claims 1
- 229910021641 deionized water Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 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
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture 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 compound C=1C=CC=CC=1N(C(=NC(C)C)NC(C)C)C1=CC=CC=C1 PMNPSCJVKKSJSG-UHFFFAOYSA-N 0.000 description 2
- VPYOROSRDYVFDU-UHFFFAOYSA-N 2,3,5,8-tetraphenylquinoxaline Chemical compound C1=CC=CC=C1C(C1=NC(=C(C=2C=CC=CC=2)N=C11)C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 VPYOROSRDYVFDU-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- YOOWJTSNIZYWCT-UHFFFAOYSA-N [Ir]#P Chemical compound [Ir]#P YOOWJTSNIZYWCT-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- MQRCTQVBZYBPQE-UHFFFAOYSA-N 189363-47-1 Chemical compound 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
- 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
- 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 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 125000000217 alkyl 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
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 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
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- 230000000007 visual effect Effects 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
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to organic photoelectrical material technical fields, more particularly to a kind of complex of iridium, preparation method and application for being used as phosphor material.Not only luminous efficiency is high for complex of iridium produced by the present invention, and emits light color and easily adjust.The main ligand skeleton structure having the same of such complex of iridium can be realized wavelength of transmitted light and adjust on a large scale from blue green light to feux rouges merely because position difference of the hetero atom on main ligand is different with hetero atom type.In addition, the preparation method of different colours luminescent material is essentially identical, it is easy to operate.
Description
Technical field
The invention belongs to organic photoelectrical material technical field, more particularly to a kind of complex of iridium for being used as phosphor material, its
Preparation method and application.
Background technique
Organic Light Emitting Diode (English name OrganicLight-EmittingDiode, abbreviation OLED) is one kind by organic
The solid-state devices of material film composition, can shine after applying voltage.Compared to traditional light emitting diode (LED) and liquid crystal
Show (LCD), OLED have wide self-luminous, clear beautiful, frivolous, fast response time, visual angle, low-power consumption, Applicable temperature range it is big,
The features such as manufacturing process is simple.OLED can do the dreamlike display for rolling over everywhere as imaging wallpaper, rolling up, paste, hanging, and be expected to that liquid will be replaced
Crystalline substance display, is known as " ultimate display technology ".In addition, OLED is as planar light source, either in structure or in light source matter
The advantage that all there is traditional LED illumination can not reach for amount, selling point etc..
Luminescent material is one of core material of OLED device.Largely studies have shown that transient metal complex conduct has
Electroluminescent material has a unique advantage, such as high efficiency, and illuminant colour covering surface is wide etc..Wherein iridium (III) complex has
The features such as thermostabilization is good, lifetime of excited state is short, luminous efficiency is high and luminescent color is easily adjusted.
Applied to the full-color display of OLED, the red that must be generally had excellent performance simultaneously, green and blue OLED device.
It, can also be white using blue light and yellow light complementation synthesis other than using tri- color of RGB synthesis white light in OLED white-light illuminating field
Light.In general, for the iridium phosphor material for realizing different colours, such as red, yellow, green, blue light, it needs using different structure
Main ligand.And the preparation method of different materials is also not quite similar, and increases the complexity of material production to a certain extent.
Therefore, it is similar to develop a kind of chemical structure, but emits the phosphor material that optical range can be adjusted substantially, to mass production different colours
Phosphor material has important meaning.
Summary of the invention
The present invention in view of the deficiency of the prior art, provides a kind of complex of iridium for being used as phosphor material, its system
Preparation Method and application.
The technical scheme to solve the above technical problems is that a kind of complex of iridium for being used as phosphor material, knot
Structure formula is as follows:
Wherein, R1、R2、R3、R4、R5、R6、R7、RAIndependent is hydrogen, deuterium, substituted or non-substituted alkyl, naphthenic base, hydroxyl
Base, amino, sulfydryl, alkenyl, alkynyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkoxy, aryloxy group, amine
Base, silylation, halogen, CN, SCN, NO2、CR8R9NR10R11Or CF3Any one；R8、R9、R10、R11It is independent for hydrogen,
Deuterium, substituted or non-substituted alkyl, naphthenic base, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, substituted or non-substituted aryl, substitution or non-
Substituted heteroaryl, alkoxy, aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one；
(L^Z) it is assistant ligand, is that the main ligand in left side in bidentate ligand, with structure above is identical or different；
X1、X2、X3Independent is O, S, Se, NR12Or CR13；R12And R13Independent is hydrogen, deuterium, substitution or non-
Replace alkyl, naphthenic base, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl,
Alkoxy, aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one；
RAReplace for monosubstituted, two substitutions or three；
M > 0, and m is integer；N >=0, and n is integer.
Wherein, R1、R2、R3、R4、R5、R6、R7、X1、X2And X3, two groups of arbitrary neighborhood connect to form cyclic group,
The cyclic group of formation may include one or more hetero atom.
Further, R5And R6The abutment of connection formation-(Y)-, the Y are O, S, Se or NR14；Wherein, R14For hydrogen, deuterium,
Substituted or non-substituted alkyl, naphthenic base, hydroxyl, alkenyl, alkynyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkane
Oxygroup, aryloxy group, silylation, halogen or CF3Any one.
Further, R5And R6Connect formation-(XR15R16) z- abutment；Wherein, R15And R16It is independent for hydrogen, deuterium,
Substituted or non-substituted alkyl, naphthenic base, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, substituted or non-substituted aryl, substitution non-take
For heteroaryl, alkoxy, aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one；The X be C,
Si or Ge；Z > 0, and z is integer.
Further, the assistant ligand (L^Z) be acetylacetone,2,4-pentanedione, 2- pyridine carboxylic acid, 2- phenylpyridine, 2,2,6,6- tetra-
Appointing in methyl -3,5- pimelic acid, (E)-N, N'- diisopropyl benzenecarboximidamide or (Z) -2,3- diisopropyl -1,1- diphenylguanidine
It anticipates one kind.
Preferably, above-mentioned complex of iridium, structural formula are respectively as follows:
Second object of the present invention is to provide the preparation method of above-mentioned complex of iridium, and steps are as follows:
(1) raw material I and raw material II are obtained into main ligand by C-N coupling reaction；
(2) under nitrogen protection, main ligand is dissolved in ethylene glycol monoethyl ether, hydrated iridium trichloride and deionization is added
Water, heating reaction obtain iridium chlorine bridge complex；
(3) under alkaline condition, by iridium chlorine bridge complex and assistant ligand (L^Z) heating reflux reaction, iridium phosphorescence is obtained
Material；
Wherein, the raw material I is 1H- indoles；
The raw material II is halo-furan and pyridine, halogenated thiophene and pyridine or halogenated pyrrole and pyridine；
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 acid, 2- phenylpyridine, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'- diisopropyl benzene
Any one in carbonamidine, (Z) -2,3- diisopropyl -1,1- diphenylguanidine.
Third object of the present invention is to provide above-mentioned complex of iridium as electroluminescent material, in organic electroluminescent
Application in device.
The beneficial effects of the present invention are: not only luminous efficiency is high for complex of iridium produced by the present invention, but also emit the wave of light
Length can be in a wide range of interior adjusting.The main ligand skeleton structure having the same of such complex of iridium, merely because hetero atom is in master
Position difference on ligand is different with hetero atom type, to realize that wavelength of transmitted light is adjusted on a large scale from blue green light to feux rouges
Section.In addition, the preparation method of different colours luminescent material is essentially identical, it is easy to operate.
Detailed description of the invention
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 embodiment
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit
Determine the scope of the present invention.
Embodiment 1
The synthesis of complex of iridium 1, reaction equation are as follows:
(1) main ligand is prepared
(2) chlorine bridge dimer is synthesized
(3) object synthesizes
Embodiment 2
The synthesis of complex of iridium 16, reaction equation are as follows:
(1) main ligand is prepared
(2) chlorine bridge dimer is synthesized
(3) object synthesizes
Embodiment 3
The synthesis of complex of iridium 26, reaction equation are as follows:
(1) main ligand is prepared
(2) chlorine bridge dimer is synthesized
(3) object synthesizes
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 composition of the OLED that table 1 is application examples 1-3.
Table 1
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
On anode layer 2 vacuum evaporation with a thickness of 10nm NPB (N, N '-two (1- naphthalene)-N, N '-diphenyl -1,1 '-biphenyl -4-4 ' -
Diamines) hole mobile material as hole injection layer 3, wherein doping mass ratio 3% F4-TCNQ (2,3,5,6- tetra- fluoro- 7,
Tetra- cyanogen dimethyl-parabenzoquinone of 7', 8,8'-)；Be on hole injection layer 3 a layer thickness be 100nm spiro-TAD (2,2', 7,
(the diphenyl amino) -9,9'- of 7'- tetra- spiro-bisfluorene) it is used as hole transmission layer 4；Vacuum evaporation a layer thickness on hole transmission layer 4
It is used as luminescent layer 5 for 20nm CBP (4,4 '-N, the N carbazyl of '-two biphenyl), wherein doped with 3wt% complex of iridium 1；It is sending out again
On photosphere 5 successively vacuum evaporation a layer thickness be 30nm TPQ (2,3,5,8- tetraphenyl quinoxaline) as electron transfer layer 6,
With a thickness of 1nm Liq as electron injecting layer 7, finally on electron injecting layer 7 use vacuum evaporation coating deposition technique deposition of thick
Degree 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 494nm, maximum current effect
Rate is 30cd/A, and maximum external quantum efficiency is 10%.
Application examples 2
It is identical as application examples 1, with application examples 1 the difference is that: luminescent layer 5 be thickness 40nm TCTA (4,4', 4 "-
Three (9- carbazyl) triphenylamines), wherein doped with 6wt% complex of iridium 16.
Know through performance test, the maximum luminous wavelength of the electroluminescent spectrum of the device is located at 530nm, maximum current effect
Rate is 50cd/A, and maximum external quantum efficiency is 16%.
Application examples 3
It is identical as application examples 1, with application examples 1 the difference is that: luminescent layer 5 be thickness 40nm TRZ (2,4,6- tri-
(9- carbazyl) -1,3,5-triazines), wherein doped with 2wt% complex of iridium 26.
Know through performance test, the maximum luminous wavelength of the electroluminescent spectrum of the device is located at 601nm, maximum current effect
Rate is 20cd/A, and maximum external quantum efficiency is 13%.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and
Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (9)
1. the complex of iridium that one kind is used as phosphor material, which is characterized in that its structural formula is as follows:
Wherein, R1、R2、R3、R4、R5、R6、R7、RAIt is independent for hydrogen, deuterium, substituted or non-substituted alkyl, naphthenic base, hydroxyl,
Amino, sulfydryl, alkenyl, alkynyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkoxy, aryloxy group, amido, silicon
Alkyl, halogen, CN, SCN, NO2、CR8R9NR10R11Or CF3Any one；R8、R9、R10、R11It is independent for hydrogen, deuterium, take
It is generation or non substituted alkyl, naphthenic base, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, substituted or non-substituted aryl, substituted or non-substituted
Heteroaryl, alkoxy, aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one；
(L^Z) it is assistant ligand, is that the main ligand in left side in bidentate ligand, with structure above is identical or different；
X1、X2、X3Independent is O, S, Se, NR12Or CR13；R12And R13It is independent for hydrogen, it is deuterium, substituted or non-substituted
Alkyl, naphthenic base, hydroxyl, amino, sulfydryl, alkenyl, alkynyl, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alcoxyl
Base, aryloxy group, amido, silylation, halogen, CN, SCN, NO2Or CF3Any one；
RAReplace for monosubstituted, two substitutions or three；
M > 0, and m is integer；N >=0, and n is integer.
2. complex of iridium according to claim 1, which is characterized in that R1、R2、R3、R4、R5、R6、R7、X1、X2And X3, arbitrarily
Two adjacent groups connect to form cyclic group.
3. complex of iridium according to claim 2, which is characterized in that R1、R2、R3、R4、R5、R6、R7、X1、X2And X3, arbitrarily
It includes one or more hetero atom that two adjacent groups, which connect the cyclic group to be formed,.
4. complex of iridium according to claim 2, which is characterized in that R5And R6The abutment of connection formation-(Y)-, the Y
For O, S, Se or NR14；Wherein, R14For hydrogen, deuterium, substituted or non-substituted alkyl, naphthenic base, hydroxyl, alkenyl, alkynyl, substitution or non-
Substituted aryl, substituted or non-substituted heteroaryl, alkoxy, aryloxy group, silylation, halogen or CF3Any one.
5. complex of iridium according to claim 2, which is characterized in that R5And R6Connect formation-(XR15R16) z- abutment；
Wherein, R15And R16Independent is hydrogen, deuterium, substituted or non-substituted alkyl, naphthenic base, hydroxyl, amino, sulfydryl, alkenyl, alkynes
Base, substituted or non-substituted aryl, substituted or non-substituted heteroaryl, alkoxy, aryloxy group, amido, silylation, halogen, CN, SCN,
NO2Or CF3Any one；The X is C, Si or Ge；Z > 0, and z is integer.
6. complex of iridium according to claim 1, which is characterized in that the assistant ligand (L^Z) is acetylacetone,2,4-pentanedione, 2-
Pyridine carboxylic acid, 2- phenylpyridine, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'- diisopropyl benzenecarboximidamide or (Z) -2,
Any one in 3- diisopropyl -1,1- diphenylguanidine.
7. complex of iridium according to claim 1, which is characterized in that its structural formula are as follows:
8. a kind of preparation method of complex of iridium described in claim 1, which is characterized in that steps are as follows:
(1) raw material I and raw material II are obtained into main ligand by C-N coupling reaction；
(2) under nitrogen protection, main ligand is dissolved in ethylene glycol monoethyl ether, hydrated iridium trichloride and deionized water is added, adds
Thermal response obtains iridium chlorine bridge complex；
(3) under alkaline condition, by iridium chlorine bridge complex and assistant ligand (L^Z) heating reflux reaction, complex of iridium is obtained；
Wherein, the raw material I is 1H- indoles；
The raw material II is halo-furan and pyridine, halogenated thiophene and pyridine or halogenated pyrrole and pyridine；
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 acid, 2- phenylpyridine, 2,2,6,6- tetramethyl -3,5- pimelic acid, (E)-N, N'- diisopropyl benzenecarboximidamide,
(Z) any one in -2,3- diisopropyl -1,1- diphenylguanidine.
9. a kind of any one of claim 1-7 complex of iridium is as electroluminescent material, in organic electroluminescence device
Application.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107417738A (en) * | 2017-08-30 | 2017-12-01 | 烟台显华光电材料研究院有限公司 | One kind is used as transient metal complex, its preparation method and the application of phosphor material |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011238944A (en) * | 2011-06-28 | 2011-11-24 | Konica Minolta Holdings Inc | Organic electroluminescent device and display using the same |
| CN102449107A (en) * | 2009-04-06 | 2012-05-09 | 通用显示公司 | Metal complex comprising novel ligand structures |
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2017
- 2017-06-23 CN CN201710487230.9A patent/CN109111480A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102449107A (en) * | 2009-04-06 | 2012-05-09 | 通用显示公司 | Metal complex comprising novel ligand structures |
| JP2011238944A (en) * | 2011-06-28 | 2011-11-24 | Konica Minolta Holdings Inc | Organic electroluminescent device and display using the same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107417738A (en) * | 2017-08-30 | 2017-12-01 | 烟台显华光电材料研究院有限公司 | One kind is used as transient metal complex, its preparation method and the application of phosphor material |
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