CN108864167A - A kind of preparation method of metal complex OLED material of main part - Google Patents
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- CN108864167A CN108864167A CN201811103517.8A CN201811103517A CN108864167A CN 108864167 A CN108864167 A CN 108864167A CN 201811103517 A CN201811103517 A CN 201811103517A CN 108864167 A CN108864167 A CN 108864167A
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- C—CHEMISTRY; METALLURGY
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- 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 System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
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- 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
Abstract
The present invention relates to field of new material preparation, particularly with regard to a kind of preparation method of metal complex OLED material of main part；A kind of preparation method of metal complex OLED material of main part disclosed in the method for the present invention, a kind of novel metal complex OLED material of main part of this patent preparation has phosphorescent lifetime short, quantum yield is high, and with the introducing of fluorine atom, the phosphorescent lifetime of material also further increases therewith.In addition, significantly improving electronic transmission performance using the stronger molecule of rigid structure, more excellent balanced charge transport is shown, advantageously reduces the efficiency roll-off of device under high illumination.
Description
Technical field
The present invention relates to field of material preparation, particularly with regard to a kind of preparation method of metal complex OLED material of main part.
Background technique
Material of main part is relative to luminescent material（Guest materials）For concept, and organic electroluminescence material in recent years
The research hotspot in material field, material category are also most.Material of main part not only plays dispersion luminescent material, reduces by three
The effect of weight state exciton concentration, and usually material of main part itself has centainly even good charge transport quality and energy
It is enough to transmit energy to luminescent material, the luminous efficiency of Qi Shi Pity luminescent material of luminescent material You can be greatlyd improve
CN106866672A discloses a kind of preparation method and applications of novel OLED material, the novel OLED material, including
With molecular structure shown in meeting formula (1), wherein Ar is selected from the cyclosubstituted nitrogen-containing heterocycle structure of benzene or C5~C60 polyaromatic
Any one of conjugated structure group, the material can be applied to field of organic electroluminescence, pass as luminescent material or carrier
Defeated materials'use has excellent photoelectric properties.
CN106366083A provide it is a kind of containing azepine carbazole and the OLED material of Phen structure, preparation method and
It is applied, and technical field of organic electroluminescence is belonged to.It is with structure as follows：Wherein, R1 is the virtue without substituent group
Perfume base group；R2 is containing substituent group or without the aromatic group of substituent group.The invention also discloses the preparation of above-mentioned OLED material
Method and its application.The OLED material of the invention can meet high efficiency and high thermal stability simultaneously, which has been used for
In organic electroluminescence devices, the efficiency of device can be significantly improved.
CN103468245A discloses a kind of with carrier transport ability, structure OLED material as shown in formula I, should
OLED material improves the luminous efficiency of carrier transport efficiency and device, is a kind of OLED material haveing excellent performance.The invention
The preparation method and application of the OLED material are also disclosed, synthetic route is simple to operation, and reaction yield is higher, has fine
Industrial prospect；The organic electroluminescent LED prepared using this OLED material is, it can be achieved that high brightness, high efficiency, low electricity
The effect of pressure, can effectively avoid screen dim spot, and performance is more excellent.
Quadripole material of main part becomes in material of main part due to that can be provided simultaneously with good hole and electron transport ability
A kind of material outstanding, but this kind of material there are quantum efficiencies not high enough, the poor disadvantage of the morphological stability of material,
It can not adapt to blue light or white light parts requirement.
Summary of the invention
To solve the above-mentioned problems, the present invention provides a kind of preparation methods of metal complex OLED material of main part.
A kind of preparation method of metal complex OLED material of main part, technology of preparing scheme are as follows：
According to mass fraction, by 12.6-16.7 parts of metal salt, 45.6-55.4 parts of organic ligand molecule, 100-150 parts
Solvent and 40-60 parts of purified water are added in reaction kettle, are vacuumized, with high pure nitrogen displaced air, and in triplicate；In height
135-140 DEG C of temperature control under purity nitrogen gas shielded, back flow reaction 24-30h；It completes reaction to be cooled to room temperature, 180- is added into system
220 parts of purified water, is then filtered, and is respectively washed three times with purified water and ethyl alcohol, obtains dimer after then drying；By what is obtained
Dimer is added in reaction kettle, and 32.6-36.8 parts of potassium carbonate, the fluoro- 2- pyridine first of 15.2-20.6 parts of 3- is then added
Acid, 0.01-0.06 parts of -5 Β of 3,7- diketone-cholestane -24- acid, 0.01-0.08 parts of tetraphenylboronic acid caesium, 0.01-0.06
Part 1- (dimethylisopropyl silane) imidazoles, bis- (2'- the ethylhexyl) -2,7- dibromo fluorenes of 0.01-0.06 part of 9,9- with
140-180 parts of solvent, vacuumizes, with high pure nitrogen displaced air, and in triplicate；The temperature control 135- under high pure nitrogen protection
140 DEG C, back flow reaction 24-30h；It completes reaction to be cooled to room temperature, 260-320 parts of purified water is added into system, then mistake
Filter is respectively washed three times with purified water and ethyl alcohol, and a kind of novel metal complex OLED material of main part can be obtained after dry.
The metal salt is ytterbium trichloride or yttrium chloride or iridium chloride.
The solvent is ethylene glycol ethyl ether or diethylene glycol dimethyl ether or ethylene glycol ether acetate.
The organic ligand molecule is prepared according to following scheme：
According to mass fraction, by the fluorine-based benzene of 10.2-15.8 parts of 1- (5- picolyl) -2,4- bis-, 9.6-15.8 parts of N-
Bromo-succinimide, 8.2-12.8 parts of azo-bis-isobutyl cyanide and 260-300 parts of carbon tetrachloride are added in reaction kettle, control
Warm 76-85 DEG C, it is stirred to react 3.5-8.5h；350-500 parts of purified water is added in reaction kettle after completing reaction, is then made
With 800-1000 parts of methylene chloride aqueous layer extracted in three times, organic layer is merged, saturated common salt washes organic layer to neutrality, so
It will be filtered after organic layer drying with desiccant afterwards, obtained solution be evaporated, it is spare to obtain intermediate；
According to mass fraction, by bis- (triphenyl the silicon substrate) -9H- carbazoles of 10.3-16.6 parts of 3,6- and 60-80 parts of N, N- diformazan
Base formamide is added in reaction kettle, and stirring 20-30min is completely dissolved；Then under condition of ice bath, in three times by 0.32-
0.86 part of sodium hydride is added in reaction kettle, and continuation reacts 30-50min under condition of ice bath；Then the 2.7-6.5 that will be obtained
The intermediate of part is added in reaction kettle, reacts 200-300min at room temperature；After completing reaction, system is poured into 300-
Precipitating in 400 parts of ice water, is then filtered, and is washed with water and is dried afterwards three times, and obtained product obtains one kind by chromatography
Organic ligand molecule.
The chromatography uses the silicagel column of 200-300 mesh, and the leacheate used is that n-hexane and methylene chloride are pressed
According to 3-7:1 ratio is formulated.
A kind of preparation method of metal complex OLED material of main part disclosed in the method for the present invention, one kind of this patent preparation
Novel metal complex OLED material of main part has phosphorescent lifetime short, and quantum yield is high, with the introducing of fluorine atom, material
Phosphorescent lifetime also further increases therewith.In addition, significantly improving electronic transmission performance, table using the stronger molecule of rigid structure
Reveal more excellent balanced charge transport, advantageously reduces the efficiency roll-off of device under high illumination.
Specific embodiment
The invention is described further below by specific embodiment：
Embodiment 1
A kind of preparation method of metal complex OLED material of main part, technology of preparing scheme are as follows：
According to mass fraction, by 14.7 parts of metal salt, 50.4 parts of organic ligand molecule, 130 parts of solvent and 50 parts it is pure
Change water to be added in reaction kettle, vacuumize, with high pure nitrogen displaced air, and in triplicate；The temperature control under high pure nitrogen protection
138 DEG C, back flow reaction 28h；It completes reaction to be cooled to room temperature, 200 parts of purified water is added into system, then filters, use is pure
Change water and ethyl alcohol respectively washs three times, obtains dimer after then drying；Obtained dimer is added in reaction kettle, then plus
Enter the fluoro- 2- pyridine carboxylic acid of 35.8 parts of potassium carbonate, 18.6 parts of 3-, 0.05 part of -5 Β of 3,7- diketone-cholestane -24- acid,
0.05 part of tetraphenylboronic acid caesium, 0.02 part of 1- (dimethylisopropyl silane) imidazoles, bis- (the 2'- ethyls of 0.03 part of 9,9-
Hexyl) -2,7- dibromo fluorenes and 160 parts of solvent, it vacuumizes, with high pure nitrogen displaced air, and in triplicate；In high pure nitrogen
Protect lower 138 DEG C of temperature control, back flow reaction 28h；It completes reaction to be cooled to room temperature, 280 parts of purified water is added into system, then
Filtering is respectively washed three times with purified water and ethyl alcohol, and a kind of novel metal complex OLED material of main part can be obtained after dry.
The metal salt is ytterbium trichloride.
The solvent is diethylene glycol dimethyl ether.
The organic ligand molecule is prepared according to following scheme：
According to mass fraction, by the fluorine-based benzene of 11.5 parts of 1- (5- picolyl) -2,4- bis-, 10.2 parts of N- bromo succinyl
Imines, 8.5 parts of azo-bis-isobutyl cyanide and 260-300 parts of carbon tetrachloride are added in reaction kettle, 80 DEG C of temperature control, are stirred to react
7.5h；430 parts of purified water is added in reaction kettle after completing reaction, is then extracted in three times using 900 parts of methylene chloride
Water intaking layer, organic layer is merged, saturated common salt washing organic layer to neutrality, then will be filtered after organic layer drying with desiccant,
Obtained solution is evaporated, it is spare to obtain intermediate；
According to mass fraction, by bis- (triphenyl the silicon substrate) -9H- carbazoles of 15.4 parts of 3,6- and 70 parts of n,N-Dimethylformamide
It is added in reaction kettle, stirring 25min is completely dissolved；Then under condition of ice bath, 0.74 part of sodium hydride is added in three times
Into reaction kettle, continuation reacts 40min under condition of ice bath；Then obtain 6.3 parts of intermediate is added in reaction kettle,
260min is reacted at room temperature；After completing reaction, system is poured into precipitating in 350 parts of ice water, then filters, is washed with water
It washs and dries afterwards three times, obtained product obtains a kind of organic ligand molecule by chromatography.
The chromatography uses the silicagel column of 200-300 mesh, and the leacheate used is that n-hexane and methylene chloride are pressed
According to 5:1 ratio is formulated.
Embodiment 2
A kind of preparation method of metal complex OLED material of main part, technology of preparing scheme are as follows：
According to mass fraction, by 12.6 parts of metal salt, 45.6 parts of organic ligand molecule, 100 parts of solvent and 40 parts it is pure
Change water to be added in reaction kettle, vacuumize, with high pure nitrogen displaced air, and in triplicate；The temperature control under high pure nitrogen protection
135 DEG C, back flow reaction is for 24 hours；It completes reaction to be cooled to room temperature, 180 parts of purified water is added into system, then filters, use is pure
Change water and ethyl alcohol respectively washs three times, obtains dimer after then drying；Obtained dimer is added in reaction kettle, then plus
Enter the fluoro- 2- pyridine carboxylic acid of 32.6 parts of potassium carbonate, 15.2 parts of 3-, 0.01 part of -5 Β of 3,7- diketone-cholestane -24- acid,
0.01 part of tetraphenylboronic acid caesium, 0.01 part of 1- (dimethylisopropyl silane) imidazoles, bis- (the 2'- ethyls of 0.01 part of 9,9-
Hexyl) -2,7- dibromo fluorenes and 140 parts of solvent, it vacuumizes, with high pure nitrogen displaced air, and in triplicate；In high pure nitrogen
Lower 135 DEG C of temperature control is protected, back flow reaction is for 24 hours；It completes reaction to be cooled to room temperature, 260 parts of purified water is added into system, then
Filtering is respectively washed three times with purified water and ethyl alcohol, and a kind of novel metal complex OLED material of main part can be obtained after dry.
The metal salt is yttrium chloride.
The solvent is ethylene glycol ether acetate.
The organic ligand molecule is prepared according to following scheme：
According to mass fraction, by the fluorine-based benzene of 10.2 parts of 1- (5- picolyl) -2,4- bis-, 9.6 parts of N- bromo succinyl
Imines, 8.2 parts of azo-bis-isobutyl cyanide and 260 parts of carbon tetrachloride are added in reaction kettle, 76 DEG C of temperature control, are stirred to react
3.5h；350 parts of purified water is added in reaction kettle after completing reaction, is then extracted in three times using 800 parts of methylene chloride
Water intaking layer, organic layer is merged, saturated common salt washing organic layer to neutrality, then will be filtered after organic layer drying with desiccant,
Obtained solution is evaporated, it is spare to obtain intermediate；
According to mass fraction, by bis- (triphenyl the silicon substrate) -9H- carbazoles of 10.3 parts of 3,6- and 60 parts of n,N-Dimethylformamide
It is added in reaction kettle, stirring 20min is completely dissolved；Then under condition of ice bath, 0.32 part of sodium hydride is added in three times
Into reaction kettle, continuation reacts 30min under condition of ice bath；Then obtain 2.7 parts of intermediate is added in reaction kettle,
200min is reacted at room temperature；After completing reaction, system is poured into precipitating in 300 parts of ice water, then filters, is washed with water
It washs and dries afterwards three times, obtained product obtains a kind of organic ligand molecule by chromatography.
The chromatography uses the silicagel column of 200-300 mesh, and the leacheate used is that n-hexane and methylene chloride are pressed
According to 3:1 ratio is formulated.
Embodiment 3
A kind of preparation method of metal complex OLED material of main part, technology of preparing scheme are as follows：
According to mass fraction, by 16.7 parts of metal salt, 55.4 parts of organic ligand molecule, 150 parts of solvent and 60 parts it is pure
Change water to be added in reaction kettle, vacuumize, with high pure nitrogen displaced air, and in triplicate；The temperature control under high pure nitrogen protection
140 DEG C, back flow reaction 30h；It completes reaction to be cooled to room temperature, 220 parts of purified water is added into system, then filters, use is pure
Change water and ethyl alcohol respectively washs three times, obtains dimer after then drying；Obtained dimer is added in reaction kettle, then plus
Enter the fluoro- 2- pyridine carboxylic acid of 36.8 parts of potassium carbonate, 20.6 parts of 3-, 0.06 part of -5 Β of 3,7- diketone-cholestane -24- acid,
0.08 part of tetraphenylboronic acid caesium, 0.06 part of 1- (dimethylisopropyl silane) imidazoles, bis- (the 2'- ethyls of 0.06 part of 9,9-
Hexyl) -2,7- dibromo fluorenes and 180 parts of solvent, it vacuumizes, with high pure nitrogen displaced air, and in triplicate；In high pure nitrogen
Protect lower 140 DEG C of temperature control, back flow reaction 30h；It completes reaction to be cooled to room temperature, 320 parts of purified water is added into system, then
Filtering is respectively washed three times with purified water and ethyl alcohol, and a kind of novel metal complex OLED material of main part can be obtained after dry.
The metal salt is iridium chloride.
The solvent is ethylene glycol ethyl ether.
The organic ligand molecule is prepared according to following scheme：
According to mass fraction, by the fluorine-based benzene of 15.8 parts of 1- (5- picolyl) -2,4- bis-, 15.8 parts of N- bromo succinyl
Imines, 12.8 parts of azo-bis-isobutyl cyanide and 300 parts of carbon tetrachloride are added in reaction kettle, 85 DEG C of temperature control, are stirred to react
8.5h；500 parts of purified water is added in reaction kettle after completing reaction, is then extracted in three times using 1000 parts of methylene chloride
Water intaking layer, organic layer is merged, saturated common salt washing organic layer to neutrality, then will be filtered after organic layer drying with desiccant,
Obtained solution is evaporated, it is spare to obtain intermediate；
According to mass fraction, by bis- (triphenyl the silicon substrate) -9H- carbazoles of 16.6 parts of 3,6- and 80 parts of n,N-Dimethylformamide
It is added in reaction kettle, stirring 30min is completely dissolved；Then under condition of ice bath, 0.86 part of sodium hydride is added in three times
Into reaction kettle, continuation reacts 50min under condition of ice bath；Then obtain 6.5 parts of intermediate is added in reaction kettle,
300min is reacted at room temperature；After completing reaction, system is poured into precipitating in 400 parts of ice water, then filters, is washed with water
It washs and dries afterwards three times, obtained product obtains a kind of organic ligand molecule by chromatography.
The chromatography uses the silicagel column of 200-300 mesh, and the leacheate used is that n-hexane and methylene chloride are pressed
According to 7:1 ratio is formulated.
Comparative example 1
The fluoro- 2- pyridine carboxylic acid of 3-, the other the same as in Example 1 is not added.
Comparative example 2
- 5 Β of 3,7- diketone-cholestane -24- acid, the other the same as in Example 1 is not added.
Comparative example 3
Tetraphenylboronic acid caesium, the other the same as in Example 1 is not added.
Comparative example 4
1- (dimethylisopropyl silane) imidazoles, the other the same as in Example 1 is not added.
Comparative example 5
Bis- (2'- ethylhexyl) -2,7- dibromo fluorenes of 9,9-, the other the same as in Example 1 is not added.
Table：The performance for the test specimen that different process is made compares.
| Number | Maximum external quantum efficiency（%） | Yield（%） |
| Embodiment 1 | 25.3 | 70.9 |
| Embodiment 2 | 25.5 | 70.2 |
| Embodiment 3 | 25.6 | 71.5 |
| Comparative example 1 | 24.1 | 61.4 |
| Comparative example 2 | 23.5 | 66.9 |
| Comparative example 3 | 23.3 | 63.1 |
| Comparative example 4 | 23.9 | 68.7 |
| Comparative example 5 | 25.1 | 58.8 |
Claims (5)
1. a kind of preparation method of metal complex OLED material of main part, technology of preparing scheme are as follows：
According to mass fraction, by 12.6-16.7 parts of metal salt, 45.6-55.4 parts of organic ligand molecule, 100-150 parts
Solvent and 40-60 parts of purified water are added in reaction kettle, are vacuumized, with high pure nitrogen displaced air, and in triplicate；In height
135-140 DEG C of temperature control under purity nitrogen gas shielded, back flow reaction 24-30h；It completes reaction to be cooled to room temperature, 180- is added into system
220 parts of purified water, is then filtered, and is respectively washed three times with purified water and ethyl alcohol, obtains dimer after then drying；By what is obtained
Dimer is added in reaction kettle, and 32.6-36.8 parts of potassium carbonate, the fluoro- 2- pyridine first of 15.2-20.6 parts of 3- is then added
Acid, 0.01-0.06 parts of -5 Β of 3,7- diketone-cholestane -24- acid, 0.01-0.08 parts of tetraphenylboronic acid caesium, 0.01-0.06
Part 1- (dimethylisopropyl silane) imidazoles, bis- (2'- the ethylhexyl) -2,7- dibromo fluorenes of 0.01-0.06 part of 9,9- with
140-180 parts of solvent, vacuumizes, with high pure nitrogen displaced air, and in triplicate；The temperature control 135- under high pure nitrogen protection
140 DEG C, back flow reaction 24-30h；It completes reaction to be cooled to room temperature, 260-320 parts of purified water is added into system, then mistake
Filter is respectively washed three times with purified water and ethyl alcohol, and a kind of novel metal complex OLED material of main part can be obtained after dry.
2. a kind of preparation method of metal complex OLED material of main part according to claim 1, it is characterised in that：It is described
Metal salt be ytterbium trichloride or yttrium chloride or iridium chloride.
3. a kind of preparation method of metal complex OLED material of main part according to claim 1, it is characterised in that：It is described
Solvent be ethylene glycol ethyl ether or diethylene glycol dimethyl ether or ethylene glycol ether acetate.
4. a kind of preparation method of metal complex OLED material of main part according to claim 1, it is characterised in that：It is described
Organic ligand molecule prepared according to following scheme：
According to mass fraction, by the fluorine-based benzene of 10.2-15.8 parts of 1- (5- picolyl) -2,4- bis-, 9.6-15.8 parts of N-
Bromo-succinimide, 8.2-12.8 parts of azo-bis-isobutyl cyanide and 260-300 parts of carbon tetrachloride are added in reaction kettle, control
Warm 76-85 DEG C, it is stirred to react 3.5-8.5h；350-500 parts of purified water is added in reaction kettle after completing reaction, is then made
With 800-1000 parts of methylene chloride aqueous layer extracted in three times, organic layer is merged, saturated common salt washes organic layer to neutrality, so
It will be filtered after organic layer drying with desiccant afterwards, obtained solution be evaporated, it is spare to obtain intermediate；
According to mass fraction, by bis- (triphenyl the silicon substrate) -9H- carbazoles of 10.3-16.6 parts of 3,6- and 60-80 parts of N, N- diformazan
Base formamide is added in reaction kettle, and stirring 20-30min is completely dissolved；Then under condition of ice bath, in three times by 0.32-
0.86 part of sodium hydride is added in reaction kettle, and continuation reacts 30-50min under condition of ice bath；Then the 2.7-6.5 that will be obtained
The intermediate of part is added in reaction kettle, reacts 200-300min at room temperature；After completing reaction, system is poured into 300-
Precipitating in 400 parts of ice water, is then filtered, and is washed with water and is dried afterwards three times, and obtained product obtains one kind by chromatography
Organic ligand molecule.
5. a kind of preparation method of metal complex OLED material of main part according to claim 4, it is characterised in that：It is described
Chromatography use the silicagel column of 200-300 mesh, the leacheate used is n-hexane and methylene chloride according to 3-7:1 ratio
It is formulated.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050186445A1 (en) * | 2004-02-25 | 2005-08-25 | Eastman Kodak Company | Electroluminescent devices including conjugated polymers containing an azole structure |
| CN1671818A (en) * | 2002-07-30 | 2005-09-21 | E·I·内穆尔杜邦公司 | Metallic complexes covalently bound to conjugated polymers and electronic devices containing such compositions |
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- 2018-09-20 CN CN201811103517.8A patent/CN108864167A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1671818A (en) * | 2002-07-30 | 2005-09-21 | E·I·内穆尔杜邦公司 | Metallic complexes covalently bound to conjugated polymers and electronic devices containing such compositions |
| US20050186445A1 (en) * | 2004-02-25 | 2005-08-25 | Eastman Kodak Company | Electroluminescent devices including conjugated polymers containing an azole structure |
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Application publication date: 20181123 |