CN105440084A - Triphenylamine based trimetal core platinum complex phosphor material and synthesis method thereof - Google Patents
Triphenylamine based trimetal core platinum complex phosphor material and synthesis method thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 42
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 36
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 18
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000001308 synthesis method Methods 0.000 title claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000007787 solid Substances 0.000 claims abstract description 16
- 239000013110 organic ligand Substances 0.000 claims abstract description 15
- 239000012046 mixed solvent Substances 0.000 claims abstract description 13
- 239000003446 ligand Substances 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 10
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 238000010189 synthetic method Methods 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 150000003217 pyrazoles Chemical class 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims description 2
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 abstract description 17
- 229910052751 metal Inorganic materials 0.000 abstract description 9
- 239000002184 metal Substances 0.000 abstract description 7
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 238000005395 radioluminescence Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 description 18
- 238000001556 precipitation Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 239000011368 organic material Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- 241000024287 Areas Species 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000002194 synthesizing 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
- C07F15/0086—Platinum 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
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- 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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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a triphenylamine based trimetal core platinum complex phosphor material and a synthesis method thereof. A general structural formula of the phosphor material is represented in the specification. A direct synthesis method or a collaborative synthesis method is adopted, organic ligands react with K2PtC14, a mixed solvent is added, the mixture in the nitrogen environment is heated, cooled and added with water until solids are precipitated, the precipitated solids and auxiliary ligands are heated in nitrogen, and a product can be generated. The phosphor material contains three metal centers; by means of the molecular structure, the intersystem crossing probability from a singlet state to a triplet state in an organic metal platinum (II) complex and the radioluminescence capacity of the triplet state are improved, and the molecular structure has an important function for improvement of the luminescence property of the material.
Description
Technical field
The present invention relates to technical field of organic luminescence materials, particularly based on three metallic core platinum complex phosphor material and synthetic methods thereof of triphenylamine.
Background technology
Luminous organic material is a kind of organic compound that can be luminous when extraneous optical excitation or when external electrical field excites, usually can be divided into organic fluorescence luminescent material and Phosphorescent luminescent material according to its luminous different sources.Luminous organic material has Application Areas widely, such as sensor field, spike field and electroluminescent field etc.Especially in electroluminescent field, based on the Organic Light Emitting Diode (OrganicLightEmittingDiode of luminous organic material, OLED) have that running voltage is low, luminosity is high, luminous color enriches, can be made into the advantages such as flexible ultra-thin device, in Application Areass such as high-end new display and white-light illuminatings, there is very outstanding advantage.The achievement in research of nearly 30 years is pointed out, the Organic Light Emitting Diode theoretical internal quantum efficiency prepared by conventional fluorescent luminescent material only has 25%, and the Organic Light Emitting Diode theoretical internal quantum efficiency prepared by organometallic complex phosphorescent light-emitting materials can reach 100%, therefore research and develop the focus direction that all kinds of organometallic complex phosphorescent light-emitting materials is Organic Light Emitting Diode field always.Because of its there is good stability, luminous efficiency is high and synthesize the advantages such as simple, from phosphorescence Organic Light Emitting Diode research the earliest, organo-metallic platinum (II) complex phosphorescence luminescent material is the study hotspot of organo-metallic phosphorescent light-emitting materials always.From the octaethylporphyrin platinum (Nature being used to phosphorescence Organic Light Emitting Diode the earliest, 1998,395 (6698): 151-154) various organo-metallic platinum (II) complex phosphorescence luminescent material (PlatinumMetalsReview reported up till now, 2013,57 (1): 2-16; DaltonTransactions, 2015,44 (18): 8433-8443), its complex molecule has a common constitutional features, namely usually only contains platinum (II) metal center in these organo-metallic platinum (II) complex phosphorescence luminescent material molecular structures.For organometallic complex phosphor material, it at room temperature can produce phosphorescence, key be the existence of heavy metal element in title complex can strengthen singlet to triplet state be between alter and jump probability and strengthen the ability of triplet state attenuation, so heavy metal center is significant for the phosphorescent emissions character of luminescent material.The research starting point in view of current organo-metallic platinum (II) complex phosphorescence luminescent material is confined to the design of organic ligand substantially, does not almost have for the research with many metal centers platinum (II) complex phosphorescence luminescent material.
Summary of the invention
In order to overcome the defect of above-mentioned prior art, the object of the present invention is to provide a kind of three metallic core platinum complex phosphor material and synthetic methods thereof based on triphenylamine, develop organo-metallic platinum (II) the complex phosphorescence luminescent material with many metal centers, be organo-metallic platinum (II) the complex phosphorescence material with three metal centers, the kind of platinum complex phosphor material can be greatly enriched.
In order to achieve the above object, technical scheme of the present invention is:
Based on three metallic core platinum complex phosphor materials of triphenylamine, its general structure is:
In formula,
for nitrogenous fragrant heterocycle, comprise pyridine, pyrimidine, thiazole, benzothiazole, quinoline, isoquinoline 99.9, pyrazoles, imidazoles;
for nitrogenous fragrant heterocycle, comprise pyridine, pyrimidine, thiazole, benzothiazole, quinoline, isoquinoline 99.9, pyrazoles, imidazoles;
for nitrogenous fragrant heterocycle, comprise pyridine, pyrimidine, thiazole, benzothiazole, quinoline, isoquinoline 99.9, pyrazoles, imidazoles.
Based on the synthetic method of three metallic core platinum complex phosphor materials of triphenylamine, direct synthesis technique step is:
By organic ligand
with K
2ptCl
4according to amount of substance 1:(3 ~ 6) ratio drop in reaction vessel, under nitrogen atmosphere, adding in described reaction vessel can by the mixed solvent of the organic solvent of reactants dissolved and water again, and in mixed solvent, the volume ratio of organic solvent and water is (2 ~ 5): 1; Described organic solvent is one or more in tetrahydrofuran (THF), ethylene glycol ethyl ether, dioxane, glycol dimethyl ether; 80 DEG C to 130 DEG C reactions 5 ~ 24 hours are heated in nitrogen atmosphere; Stop heating, in reaction mixture, cold water is added after being chilled to room temperature, until there is solid to separate out, filter and dry solid of separating out, itself and assistant ligand methyl ethyl diketone are dissolved in organic solvent, the solid of separating out and assistant ligand methyl ethyl diketone are 1:(3 ~ 20 according to amount of substance ratio), being heated to 30 DEG C to 130 DEG C reactions in nitrogen atmosphere 5 ~ 24 hours can generating structure general formula be
three metallic core platinum complex phosphor materials.
Based on the synthetic method of three metallic core platinum complex phosphor materials of triphenylamine, collaborative synthesis method step is:
By organic ligand
with organic ligand L and K
2ptCl
4drop in reaction vessel, the ratio of input amount is respectively:
with organic ligand L according to amount of substance 1:3 ~ 1:6;
with K
2ptCl
4according to amount of substance 1:3 ~ 1:6; Organic ligand L is herein
in one or more, adding in described reaction vessel can by the mixed solvent of the organic solvent of reactants dissolved and water again, in mixed solvent, the volume ratio of organic solvent and water is (2 ~ 5): 1, described organic solvent is tetrahydrofuran (THF), ethylene glycol ethyl ether, dioxane, one or more in glycol dimethyl ether, 80 DEG C to 130 DEG C reactions 5 ~ 24 hours are heated in nitrogen atmosphere, stop heating, in reaction mixture, cold water is added after being chilled to room temperature, until there is solid to separate out, filter and dry solid of separating out, itself and assistant ligand methyl ethyl diketone are dissolved in organic solvent, the solid of separating out and assistant ligand methyl ethyl diketone are 1:(3 ~ 50 according to amount of substance ratio), being heated to 30 DEG C to 130 DEG C reactions in nitrogen 5 ~ 24 hours can generating structure general formula be
three metallic core platinum complex phosphor materials.
Compared with organo-metallic platinum (II) the complex phosphorescence material containing a metal center with existing, present invention obtains organo-metallic platinum (II) the complex phosphorescence material with three metal centers, the kind of platinum complex phosphor material can be greatly enriched.In addition, the existence of many metal centers makes singlet in organo-metallic platinum (II) title complex be improved to the ability of altering probability and the triplet state radioluminescence jumped between triplet state system, has vital role for the luminescent properties improving material.
Accompanying drawing explanation
Fig. 1 is for synthesizing the route map of three metallic core organo-metallic platinum (II) complex phosphorescence material Pt1 by direct synthesis technique of the present invention.
The route map that Fig. 2 synthesizes three metallic core organo-metallic platinum (II) complex phosphorescence material Pt2 for working in coordination with synthesis method by the present invention.
Fig. 3 is the luminous spectrogram of three metallic core organo-metallic platinum (II) complex phosphorescence material Pt1 and Pt2 by the embodiment synthesis of two selected by the present invention.
Embodiment
Below in conjunction with accompanying drawing, the present invention is further described.
Embodiment one:
Three metallic core organo-metallic platinum (II) the title complex Pt1 of the present embodiment, chemical formula is C
48h
42n
4o
6pt
3, structural formula is
with reference to accompanying drawing 1, the synthetic route of its direct synthesis technique comprises the following steps:
The first step: by 0.48 gram of organic ligand
with 1.21 grams of K
2ptCl
4drop in reaction vessel, add the mixed solvent of 30 milliliters of ethylene glycol ethyl ethers and water in nitrogen atmosphere, in mixed solvent, the volume ratio of ethylene glycol ethyl ether and water is 3:1, is heated to 110 DEG C in nitrogen atmosphere, stirs and is chilled to room temperature after 12 hours;
Second step: reaction mixture final in step one adds 50 ml deionized water, produces precipitation.Be precipitated by suction filtration and drying in vacuum drying oven, then precipitation and 0.5 gram of methyl ethyl diketone mixed, return stirring 12 hours in nitrogen atmosphere;
3rd step: reaction mixture final in step 2 adds 50 ml deionized water, produces precipitation.Be precipitated by suction filtration and drying can obtain thick product in vacuum drying oven, then by its purifying on self-control thin layer silica gel chromatosheet, finally obtain 0.25 gram of bright yellow solid Pt1, productive rate is 18.5%.
Its nuclear-magnetism characterization data is:
1HNMR(400MHz,CDCl
3):δ(ppm)8.90(d,J＝4.0Hz,3H),7.71(t,J＝8.0Hz,3H),7.52–7.47(m,6H),7.33(d,J＝8.0Hz,3H),7.01–6.94(m,6H),5.36(s,3H),1.95(s,9H),1.78(s,9H).
According to above-mentioned data, what illustrate that the present embodiment synthesizes is Pt1.
Embodiment two:
Three metallic core organo-metallic platinum (II) the title complex Pt2 of the present embodiment, chemical formula is C
54h
42n
4o
6pt
3s
3, structural formula is
with reference to accompanying drawing 2, the synthetic route of its collaborative synthesis method comprises the following steps:
The first step: by 0.64 gram of organic ligand
with 0.6 gram of organic ligand
and 1.21 grams of K
2ptCl
4drop in reaction vessel, add the mixed solvent of 30 milliliters of ethylene glycol ethyl ethers and water in nitrogen atmosphere, in mixed solvent, the volume ratio of ethylene glycol ethyl ether and water is 3:1, is heated to 110 DEG C in nitrogen atmosphere, stirs and is chilled to room temperature after 12 hours;
Second step: reaction mixture final in step one adds 50 ml deionized water, produces precipitation.Be precipitated by suction filtration and drying in vacuum drying oven, then precipitation and 0.5 gram of methyl ethyl diketone mixed, return stirring 12 hours in nitrogen atmosphere;
3rd step: reaction mixture final in step 2 adds 50 ml deionized water, produces precipitation.Be precipitated by suction filtration and drying can obtain thick product in vacuum drying oven, then by its purifying on self-control thin layer silica gel chromatosheet, finally obtain 0.38 gram of yellow solid Pt2, productive rate is 24.9%.
Its nuclear-magnetism characterization data is:
1hNMR (400MHz, CDCl
3): δ (ppm) 9.10 (d, J=8.4Hz, 3H), 7.75 (d, J=8.0Hz, 3H), 7.57 (s, 3H), 7.51 (t, J=8.0Hz, 3H), 7.41 – 7.35 (m, 6H), 6.97 (d, J=8.4Hz, 3H), 5.42 (s, 3H), 2.01 (s, 9H), 1.77 (s, 9H).
According to above-mentioned data, what illustrate that the present embodiment synthesizes is Pt2.
Below by reference to the accompanying drawings the specific embodiment of the present invention is described; but these explanations can not be understood to limit scope of the present invention; protection scope of the present invention is limited by the claims of enclosing, and any change on the claims in the present invention basis is all protection scope of the present invention.
Claims (3)
1., based on three metallic core platinum complex phosphor materials of triphenylamine, it is characterized in that this three metallic cores platinum complex has following general structural formula:
In formula,
for nitrogenous fragrant heterocycle, comprise pyridine, pyrimidine, thiazole, benzothiazole, quinoline, isoquinoline 99.9, pyrazoles, imidazoles;
for nitrogenous fragrant heterocycle, comprise pyridine, pyrimidine, thiazole, benzothiazole, quinoline, isoquinoline 99.9, pyrazoles, imidazoles;
for nitrogenous fragrant heterocycle, comprise pyridine, pyrimidine, thiazole, benzothiazole, quinoline, isoquinoline 99.9, pyrazoles, imidazoles.
2., based on the synthetic method of the three metallic core platinum complex phosphor materials based on triphenylamine according to claim 1, it is characterized in that,
Direct synthesis technique step is:
By organic ligand
with K
2ptCl
4according to amount of substance 1:(3 ~ 6) ratio drop in reaction vessel, under nitrogen atmosphere, adding in described reaction vessel can by the mixed solvent of the organic solvent of reactants dissolved and water again, and in mixed solvent, the volume ratio of organic solvent and water is (2 ~ 5): 1; Described organic solvent is one or more in tetrahydrofuran (THF), ethylene glycol ethyl ether, dioxane, glycol dimethyl ether; 80 DEG C to 130 DEG C reactions 5 ~ 24 hours are heated in nitrogen atmosphere; Stop heating, in reaction mixture, cold water is added after being chilled to room temperature, until there is solid to separate out, filter and dry solid of separating out, itself and assistant ligand methyl ethyl diketone are dissolved in organic solvent, the solid of separating out and assistant ligand methyl ethyl diketone are 1:(3 ~ 20 according to amount of substance ratio), being heated to 30 DEG C to 130 DEG C reactions in nitrogen atmosphere 5 ~ 24 hours can generating structure general formula be
three metallic core platinum complex phosphor materials.
3., based on the synthetic method of the three metallic core platinum complex phosphor materials based on triphenylamine according to claim 1, it is characterized in that,
Collaborative synthesis method step is:
By organic ligand
with organic ligand L and K
2ptCl
4drop in reaction vessel, the ratio of input amount is respectively:
with organic ligand L according to amount of substance 1:3 ~ 1:6;
with K
2ptCl
4according to amount of substance 1:3 ~ 1:6.
Organic ligand L is herein
in one or more, adding in described reaction vessel can by the mixed solvent of the organic solvent of reactants dissolved and water again, in mixed solvent, the volume ratio of organic solvent and water is (2 ~ 5): 1, described organic solvent is tetrahydrofuran (THF), ethylene glycol ethyl ether, dioxane, one or more in glycol dimethyl ether, 80 DEG C to 130 DEG C reactions 5 ~ 24 hours are heated in nitrogen atmosphere, stop heating, in reaction mixture, cold water is added after being chilled to room temperature, until there is solid to separate out, filter and dry solid of separating out, itself and assistant ligand methyl ethyl diketone are dissolved in organic solvent, the solid of separating out and assistant ligand methyl ethyl diketone are 1:(3 ~ 50 according to amount of substance ratio), being heated to 30 DEG C to 130 DEG C reactions in nitrogen 5 ~ 24 hours can generating structure general formula be
three metallic core platinum complex phosphor materials.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020122359A1 (en) * | 2018-12-12 | 2020-06-18 | 주식회사 랩토 | Tribenzazole amine derivative and organic electroluminescent device comprising same |
| CN113105509A (en) * | 2021-04-02 | 2021-07-13 | 西安交通大学 | Complex phosphorescent material based on electron-deficient functional group |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101973933A (en) * | 2010-10-22 | 2011-02-16 | 湘潭大学 | Bi(phenylpyridine) fluorene derivatives and binuclear liquid crystal polarized cyclometalated platinum complex |
| CN102372670A (en) * | 2010-08-20 | 2012-03-14 | 清华大学 | Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group |
-
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102372670A (en) * | 2010-08-20 | 2012-03-14 | 清华大学 | Arylamine compounds containing arylpyridine groups and application of arylamine compounds containing arylpyridine group |
| CN101973933A (en) * | 2010-10-22 | 2011-02-16 | 湘潭大学 | Bi(phenylpyridine) fluorene derivatives and binuclear liquid crystal polarized cyclometalated platinum complex |
Non-Patent Citations (1)
| Title |
|---|
| HAI-YING WANG ET AL.: "Synthesis and characterization of triphenylamine–benzothiazole-based donor and acceptor materials", 《SYNTHETIC METALS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020122359A1 (en) * | 2018-12-12 | 2020-06-18 | 주식회사 랩토 | Tribenzazole amine derivative and organic electroluminescent device comprising same |
| CN113195485A (en) * | 2018-12-12 | 2021-07-30 | 株式会社乐普拓 | Tripyrrolopyrrole amine derivative and organic electroluminescent device comprising the same |
| US11952372B2 (en) | 2018-12-12 | 2024-04-09 | Lapto Co., Ltd. | Tribenzazole amine derivative and organic electroluminescent device comprising same |
| CN113105509A (en) * | 2021-04-02 | 2021-07-13 | 西安交通大学 | Complex phosphorescent material based on electron-deficient functional group |
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