CN108047275B - Iridium complex phosphorescent luminescent material based on thianthrene oxide and preparation method thereof - Google Patents
Iridium complex phosphorescent luminescent material based on thianthrene oxide and preparation method thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 38
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 23
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 23
- NYVGTLXTOJKHJN-UHFFFAOYSA-N thianthrene 5-oxide Chemical compound C1=CC=C2S(=O)C3=CC=CC=C3SC2=C1 NYVGTLXTOJKHJN-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims abstract description 12
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims abstract description 12
- 239000013110 organic ligand Substances 0.000 claims abstract description 11
- 239000002244 precipitate Substances 0.000 claims description 31
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 18
- 239000012046 mixed solvent Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 239000011259 mixed solution Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000002347 injection Methods 0.000 abstract description 13
- 239000007924 injection Substances 0.000 abstract description 13
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 230000007547 defect Effects 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 2
- 238000001748 luminescence spectrum Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
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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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- 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
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
Iridium complex phosphorescent luminescent material based on thianthrene oxide and preparation thereofThe method has the structural general formula as follows:
and
Description
Technical Field
The invention relates to the field of organic luminescent materials, in particular to an iridium complex phosphorescent luminescent material based on thianthrene oxide and a preparation method thereof.
Background
Organic light-emitting materials are currently widely applied in the fields of novel ion detection, ultraviolet detection, cell imaging, organic light-emitting diodes and the like. Especially in the field of organic light emitting diodes known as next generation display and illumination technologies, organic light emitting materials have a core role, which determines the light emitting color of the organic light emitting diode and largely affects the light emitting efficiency of the organic light emitting diode. The high-performance organic light emitting material must at least have a high quantum efficiency and an excellent carrier injection transport property. Limited by the self-selected melody, the theoretical internal quantum efficiency of the organic light emitting diode prepared by the organic fluorescent material can only be 25% at most, and the theoretical internal quantum efficiency of the organic light emitting diode based on the organic phosphorescent material can reach 100%. Therefore, research and development of organic phosphorescent materials with high quantum efficiency are important ways to improve the light emitting performance of organic light emitting diodes. In addition to the quantum efficiency of the organic light emitting material, the carrier injection transport property in the organic light emitting diode device also has an important influence on the light emitting efficiency of the device, that is, the light emitting layer must have balanced hole and electron injection transport properties. However, for the related materials reported at present, the hole injection transport capability of the related materials is much larger than the electron injection transport capability, which often causes the carrier injection transport in the organic light emitting diode device to be unbalanced, and finally, the light emitting performance of the organic light emitting diode is adversely affected. Therefore, in order to balance the carrier injection transport property inside the organic light emitting diode device, it is necessary to improve the electron transport property of the organic light emitting material. However, the organic light emitting materials reported in the current research have poor quantum efficiency and electron injection and transport properties, and are very unfavorable for the practical application of the organic light emitting diode. Therefore, research and development of organic light emitting materials having both high quantum efficiency and electron injection transport capability are very important and urgent for the development of high performance organic light emitting diodes.
Disclosure of Invention
In order to overcome the technical defects of low quantum efficiency, weak electron injection and transmission capability and the like of the existing luminescent material, the invention aims to provide an iridium complex phosphorescent luminescent material based on thianthrene oxide and a preparation method thereof.
In order to achieve the purpose, the technical scheme applied by the invention is as follows:
the iridium complex phosphorescent light-emitting material based on thianthrene oxide has a structural general formula I:
wherein the circle
Represented by a cyclic structure containing the nitrogen atom N, i.e.
The preparation method of the iridium complex phosphorescent material with the structural general formula comprises the following steps:
the first step is as follows: an organic ligand is added
And iridium trichloride in an amount of substance 2: 1 ofPutting the mixture into a reaction container in proportion, adding a mixed solvent of glycol ether and water which can dissolve reactants into the reaction container under the nitrogen atmosphere, wherein the volume ratio of the glycol ether to the water in the mixed solvent is 3:1, heating the mixture to 100-110 ℃ in a nitrogen atmosphere, stirring the mixture for 12 hours, and then cooling the mixture to room temperature to generate a precipitate;
the second step is that: adding deionized water into the final reaction mixed solution in the first step, generating a precipitate in the reaction mixed solution, filtering to obtain a precipitate, drying the precipitate, dissolving the precipitate, acetylacetone and anhydrous sodium carbonate into ethylene glycol ethyl ether, and adding acetylacetone in a ratio of (1-20): 1, the ratio of the amount of the anhydrous sodium carbonate substance added to the amount of the iridium trichloride substance in the first step is (10-30): 1, refluxing and stirring in nitrogen atmosphere to generate a structural general formula
The iridium complex phosphorescent light-emitting material.
The iridium complex phosphorescent light-emitting material based on thianthrene oxide has a structural general formula II:
wherein the circle
Represented by a cyclic structure containing the nitrogen atom N, i.e.
Wherein the pentagon is
Representative of various aromatic structures, i.e.
The preparation method of the diidium complex phosphorescent material with the structural general formula comprises the following steps:
the first step is as follows: an organic ligand is added
With organic ligands
And iridium trichloride in an amount of substance 1: 1: 1, adding a mixed solvent of glycol ether and water which can dissolve reactants into a reaction container in a nitrogen atmosphere, wherein the volume ratio of the glycol ether to the water in the mixed solvent is 3:1, heating to 100-110 ℃ in the nitrogen atmosphere, stirring for 12 hours, and cooling to room temperature to generate a precipitate;
the second step is that: adding deionized water into the final reaction mixed solution in the first step, generating a precipitate in the reaction mixed solution, filtering to obtain a precipitate, drying the precipitate, dissolving the precipitate, acetylacetone and anhydrous sodium carbonate into ethylene glycol ethyl ether, and adding acetylacetone in a ratio of (1-20): 1, the ratio of the amount of the anhydrous sodium carbonate substance added to the amount of the iridium trichloride substance in the first step is (10-30): 1, refluxing and stirring in nitrogen atmosphere to generate a structural general formula
The iridium complex phosphorescent material.
Compared with the existing organic luminescent materials, the invention can not only improve the phosphorescence quantum efficiency of the complex to more than 95% by means of the thianthrene oxide functional group with strong electron-withdrawing capability, but also obviously enhance the electron injection transmission capability of the luminescent materials, thereby greatly improving the application value of the complexes in organic light-emitting diodes.
Drawings
FIG. 1 is a schematic diagram of a synthesis of an organometallic iridium phosphorescent complex Ir1 according to the present invention.
FIG. 2 is a schematic diagram of a synthesis of an organometallic iridium phosphorescent complex Ir2 according to the present invention.
FIG. 3 is a chart of the luminescence spectra of 2 selected examples of organometallic iridium phosphorescent complexes Ir1 and Ir2 synthesized according to the present invention. Wherein wavelength is the wavelength and PL intensity is the luminous intensity.
Detailed Description
The invention is further described below with reference to the accompanying drawings.
Example one
The organic metal iridium complex phosphorescent material Ir1 of the embodiment has a chemical formula of C39H27IrN2O10S4The molecular structural formula is:
referring to the attached figure 1, the synthesis steps are as follows:
the first step is as follows: 0.78mmol of organic ligand
Adding 0.39mmol of iridium trichloride and a mixed solvent of 30mL of ethylene glycol ethyl ether and water into a reaction container, adding the mixed solvent into a nitrogen atmosphere, heating the mixed solvent to 110 ℃ in the nitrogen atmosphere, stirring for 12 hours, and cooling to room temperature to generate a precipitate, wherein the volume ratio of the ethylene glycol ethyl ether to the water in the mixed solvent is 3: 1;
the second step is that: and (3) adding 50mL of deionized water into the final reaction mixed solution in the step one to generate a precipitate, performing suction filtration to obtain the precipitate, and drying in a vacuum drying oven. Then mixing the precipitate with 3.9mmol of acetylacetone and 7.8mmol of anhydrous sodium carbonate together, adding 20mL of ethylene glycol ethyl ether, refluxing and stirring for 12 hours in a nitrogen atmosphere, and adding 50mL of deionized water into the reaction mixed solution to generate a precipitate; the precipitate was obtained by suction filtration and dried in a vacuum oven to give a crude product which was then purified on a home-made thin layer silica gel chromatography plate to give 0.15 g of orange yellow solid Ir1 with a yield of 38.3% and a luminescence spectrum as shown in fig. 3.
The nuclear magnetic characterization data are as follows:1H NMR(400MHz,CDCl3,δ):8.48(d,J＝5.2Hz,2H),8.29(s,2H),8.18-8.14(m,4H),8.07-8.01(m,4H),7.73-7.69(m,4H),7.51-7.47(m,2H),6.93(s,2H),5.30(s,1H),1.82(s,6H)；13C NMR(100MHz,CDCl3,δ):185.62,157.65,150.24,148.77,143.42,139.26,139.13,137.01,133.27,133.17,132.23,129.23,125.74,125.34,124.79,120.98,119.87,103.77,28.41.
the synthesized product of this embodiment is Ir1 based on the above data.
Example two:
the organic metal iridium complex phosphorescent material Ir2 of the embodiment has a chemical formula of C41H32IrN3O6S2The molecular structural formula is:
referring to the attached FIG. 2, the synthesis steps are as follows:
the first step is as follows: 0.24mmol of organic ligand
With 0.24mmol of organic ligand
And 0.24mmol of iridium trichloride are put into a reaction container, 30mL of mixed solvent of ethylene glycol ethyl ether and water is added in a nitrogen atmosphere, the volume ratio of the ethylene glycol ethyl ether to the water in the mixed solvent is 3:1, the mixture is heated to 110 ℃ in the nitrogen atmosphere, stirred for 12 hours and then cooled to room temperature, and precipitation is generated;
the second step is that: and (3) adding 50mL of deionized water into the final reaction mixed solution in the step one to generate a precipitate, performing suction filtration to obtain the precipitate, and drying in a vacuum drying oven. The precipitate was then mixed with 2.4mmol of acetylacetone, 4.8mmol of anhydrous sodium carbonate and 20mL of ethylene glycol ethyl ether was added. Refluxing and stirring for 12 hours in a nitrogen atmosphere, and adding 50mL of deionized water into the reaction mixed solution to generate a precipitate; the precipitate was obtained by suction filtration and dried in a vacuum oven to obtain a crude product, which was then purified on a home-made thin layer silica gel chromatography plate to obtain 0.045 g of orange red solid Ir2 with a yield of 20.4% and a luminescence spectrum as shown in fig. 3.
The nuclear magnetic characterization data are as follows:1H NMR(400MHz,CDCl3,δ):8.69(d,J＝5.2Hz,1H),8.38(d,J＝5.6Hz,1H),8.29-8.27(m,2H),8.12-8.10(m,2H),8.06-8.01(m,2H),7.98-7.95(m,2H),7.84(t,J＝7.6Hz,1H),7.65-7.63(m,2H),7.43(t,J＝6.4Hz,1H),7.30(t,J＝7.6Hz,1H),7.22-7.15(m,3H),7.10(t,J＝6.0Hz,1H),5.88(s,1H),5.28(s,1H),3.91-3.85(m,2H),1.83(s,3H),1.81(s,3H),1.13(t,J＝7.2Hz,3H)；13C NMR(100MHz,CDCl3,δ):185.22,185.09,168.54,150.56,149.06,147.74,140.45,139.51,139.44,137.91,137.75,136.60,135.70,132.98,132.87,130.37,129.78,125.60,124.96,124.50,123.93,123.76,120.83,120.04,119.52,119.14,118.96,118.64,118.47,116.84,111.02,108.28,100.70,37.09,28.65,28.55,13.43.
the synthesized product of this embodiment is Ir2 based on the above data.
While the invention has been described in connection with specific embodiments thereof, it will be understood that these should not be construed as limiting the scope of the invention, which is defined in the following claims, and any variations which fall within the scope of the claims are intended to be embraced thereby.
Claims (4)
1. The iridium complex phosphorescent light-emitting material based on thianthrene oxide is characterized in that the structural general formula I is as follows:
wherein the circle
Represented by a cyclic structure containing the nitrogen atom N, i.e.
2. The preparation method of the iridium complex phosphorescent light-emitting material according to claim 1, characterized by comprising the steps of:
the first step is as follows: an organic ligand is added
And iridium trichloride in an amount of substance 2: 1, adding a mixed solvent of glycol ether and water which can dissolve reactants into a reaction container in a nitrogen atmosphere, wherein the volume ratio of the glycol ether to the water in the mixed solvent is 3:1, heating to 100-110 ℃ in the nitrogen atmosphere, stirring for 12 hours, and cooling to room temperature to generate a precipitate;
the second step is that: adding deionized water into the final reaction mixed solution in the first step, generating a precipitate in the reaction mixed solution, filtering to obtain a precipitate, drying the precipitate, dissolving the precipitate, acetylacetone and anhydrous sodium carbonate into ethylene glycol ethyl ether, and adding acetylacetone in a ratio of (1-20): 1, the ratio of the amount of the anhydrous sodium carbonate substance added to the amount of the iridium trichloride substance in the first step is (10-30): 1, refluxing and stirring in nitrogen atmosphere to generate a structural general formula
The iridium complex phosphorescent light-emitting material.
3. The iridium complex phosphorescent light-emitting material based on thianthrene oxide is characterized in that the structural general formula II is as follows:
wherein the circle
Represented by a cyclic structure containing the nitrogen atom N, i.e.
Wherein the pentagon is
Representative of various aromatic structures, i.e.
4. The preparation method of the iridium complex phosphorescent light-emitting material as claimed in claim 3, characterized by comprising the following steps:
the first step is as follows: an organic ligand is added
With organic ligands
And iridium trichloride in an amount of substance 1: 1: 1, adding a mixed solvent of glycol ether and water which can dissolve reactants into a reaction container in a nitrogen atmosphere, wherein the volume ratio of the glycol ether to the water in the mixed solvent is 3:1, heating to 100-110 ℃ in the nitrogen atmosphere, stirring for 12 hours, and cooling to room temperature to generate a precipitate;
the second step is that: adding deionized water into the final reaction mixed solution in the first step, generating a precipitate in the reaction mixed solution, filtering to obtain a precipitate, drying the precipitate, dissolving the precipitate, acetylacetone and anhydrous sodium carbonate into ethylene glycol ethyl ether, and adding acetylacetone in a ratio of (1-20): 1, the ratio of the amount of the anhydrous sodium carbonate substance added to the amount of the iridium trichloride substance in the first step is (10-30): 1, refluxing and stirring in nitrogen atmosphere to generate a structural general formula
The iridium complex phosphorescent material.
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| JP2008222635A (en) * | 2007-03-13 | 2008-09-25 | Osaka Prefecture Univ | Metal complex compound, coloring matter and organic electroluminescent element |
| KR20100119997A (en) * | 2009-05-04 | 2010-11-12 | 한국생산기술연구원 | Preparation and application of phenothiazine metal complex including isoquinoline structure |
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| JP2008222635A (en) * | 2007-03-13 | 2008-09-25 | Osaka Prefecture Univ | Metal complex compound, coloring matter and organic electroluminescent element |
| KR20100119997A (en) * | 2009-05-04 | 2010-11-12 | 한국생산기술연구원 | Preparation and application of phenothiazine metal complex including isoquinoline structure |
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Effective date of registration: 20210129 Address after: 044600 north of Zhenxing East Road, new material industrial park, Fenglingdu Development Zone, Ruicheng County, Yuncheng City, Shanxi Province Patentee after: Shanxi lvpu photoelectric New Material Technology Co., Ltd Address before: Beilin District Xianning West Road 710049, Shaanxi city of Xi'an province No. 28 Patentee before: XI'AN JIAOTONG University |