CN110183441B - Preparation method of OLED electron transport material NBphen - Google Patents
Preparation method of OLED electron transport material NBphen Download PDFInfo
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Abstract
The invention discloses a preparation method of an OLED electron transport material NBphen. The preparation method comprises the following steps: (1) under the existence of protective gas and a first organic solvent, carrying out contact reaction on 2-bromonaphthalene and metal lithium to obtain a 2-lithium naphthalene organic solution; (2) carrying out contact reaction on a Bphen organic solution and a 2-lithium naphthalene organic solution in the presence of protective gas to obtain a reaction mixture; (3) carrying out hydrolysis reaction on the reaction mixture and water to obtain an oil-water mixture; (4) and extracting an organic phase in an aqueous layer of the oil-water mixture, and then carrying out contact reaction on the organic phase and an oxidant to obtain the NBphen. The method of the invention does not need to be cooled to-78 ℃, the reaction is more convenient and the energy is saved; the reaction has high safety and is convenient for mass preparation.
Description
Technical Field
The invention belongs to the technical field of synthesis of electron transport materials, and particularly relates to a preparation method of an OLED electron transport material NBphen.
Background
In recent years, organic light-emitting diodes (OLEDs) as representative organic photoelectric materials show great commercial application prospects, and are widely applied to the fields of flat panel display and illumination [ j.smith, e.bawolek, y.k.lee, electron.lett.,2015,51(17),1312 ], which attract extensive attention in academic and industrial fields. Organic light-emitting materials are important components for the construction of OLED devices, and the development of novel high-efficiency organic light-emitting materials plays a crucial role in improving the performance of OLED devices [ Chen and bin, Zhao Zu jin, Tang and loyal. scientific bulletin, 2016,61(32),3435 ].
Early OLED devices generally employed a single layer structure, with electron transporting, hole transporting, and light emitting materials concentrated in one material and had very low brightness. In 1987, Duncong research group introduced double-layer devices and adopted Alq3The TPD is a hole transport layer and has a luminance of over 1000cd/m at a low driving voltage of less than 10V2[C.W.Tang,S.A.Vanslyke,Appl.Phys.Lett.,1987,51(12),913.]. In 1988, 3-layer structures were proposed in japan, and the electron transport, light emission, and hole transport of the device were each composed of different materials [ c.adachi, s.tokito, t.tsutsutsutsui, jpnj.appl.phys.,1988,27(2), L269.]. Nowadays, with the application of various doping methods and new materials, researchers can develop more diversified device structures, so as to greatly improve the light emitting performance of the OLED, and an electron injection layer, an electron transport layer, an organic light emitting layer, a hole transport layer, a hole injection layer, and the like can be arranged between the metal electrode and the ITO.
In an OLED device, the majority of the hole transport material has a mobility of 10-3～10-4cm2V · s, and the mobility of the electron transport material is usually 10-4～10-6cm2/(V·s)[Z.Q.Zhang,Q.Wang,Y.F.Dai,Org.Electron.,2009,10(3),491.]. The low electron mobility, poor transmission capability and the mismatch between the electron transport material and the hole material with strong transmission capability are one of the main reasons for the low efficiency and poor stability of the device. To enhance electron transport capability, electrons are constructedBalancing with holes to improve the performance of the OLED device requires the use of electron transport materials with higher mobility and more stable performance, and the construction of electron transport layers with reasonable structure and energy level matching.
The material used to make the electron transport layer must have high film stability, thermal stability and electron transport properties. Common electron transport materials include Alq3Liq, PBD, Bebq, TAZ, Bphen, etc., the chemical structures of which are shown in the following formula 1. Recent research shows that compared with a traditional device, the brightness of the device which adopts Bphen and other materials as an electron transport layer after being doped is improved by 3.5 times, and the current efficiency is improved by 1.1-2.5 times [ Yuanqili, Wang Xiufeng, muqiang.]Bphen and derivatives thereof are explained to be a good electron transport material.
As a derivative of Bphen, NBphen (2, 9-di (2-naphthyl) -4,7-diphenyl-1,10-phenanthroline, 2,9-bis (naphthalen-2-yl) -4, 7-diphenylyl-1, 10-phenanthroline) is a novel electron transport material, and the molecular structure thereof is shown in the following formula 2. NBphen has better thermal stability than Bphen. The glass transition temperature is 105 ℃, and the Bphen is 63 ℃; in thermogravimetric analysis, NBphen reached 0.5% loss on heat at 370 ℃ while Bphen was 260 ℃. Relevant research proves that an n-type electron transport layer formed by NBphen and common doping materials such as Cs-based derivatives has the advantages of improving the electron transport efficiency, being easy to evaporate and the like, and the brightness of the OLED device prepared by the method can reach 39820 cd.m at 14V-2Is obviously superior to the brightness (25000 cd.m) of the traditional device under the same condition-2)[L.-Y.Shen,X.-M.Wu,Y.-L.Hua,Acta Phys.-Chim.Sin.,2012,28(6),1497.]。
With the coming of the commercialization of OLED materials, NBphen as an electron transport material has a very wide market prospect, but the preparation method is not reported in the published literature at present, the number of relevant foreign patents is very small, the traditional butyl lithium route is used, and the synthetic method is shown in the following formula 3.
Disclosure of Invention
The invention aims to provide a synthesis method of an OLED electronic transmission material NBphen, which solves the problems of complicated operation and high risk that butyl lithium is flammable and explosive, reaction needs strict oxygen-free and water-free operation, reaction needs to be carried out at a low temperature of-78 ℃ and the like in the traditional butyl lithium route, so that the preparation method is convenient and efficient and is beneficial to large-scale preparation.
In order to achieve the above object, the present invention provides a preparation method of an OLED electron transport material NBphen, which comprises:
(1) under the existence of protective gas and a first organic solvent, carrying out contact reaction on 2-bromonaphthalene and metal lithium to obtain a 2-lithium naphthalene organic solution;
(2) carrying out contact reaction on a Bphen organic solution and the 2-lithium naphthalene organic solution in the presence of protective gas to obtain a reaction mixture;
(3) carrying out hydrolysis reaction on the reaction mixture and water to obtain an oil-water mixture;
(4) and extracting an organic phase in an aqueous layer of the oil-water mixture, and then carrying out contact reaction on the organic phase and an oxidant to obtain the NBphen.
The technical scheme of the invention has the following beneficial effects:
(1) the method of the invention uses metal lithium to replace organolithium reagents such as n-butyllithium (tert-butyllithium) and the like to carry out lithiation reaction on 2-bromonaphthalene, and the metal lithium can be conveniently weighed and processed in the air; the lithiation reaction can be carried out at 0-50 ℃ without cooling to-78 ℃, so that the reaction is more convenient and energy is saved; even if the lithiation reaction liquid contacts air, the lithiation reaction liquid does not have the risk of burning like butyl lithium, so that the safety of the reaction is improved, and the mass preparation is convenient;
(2) the method has simple operation and post-treatment steps, does not need column chromatography purification, and is suitable for industrial production;
(3) in the prior art, butyl lithium is used for reaction, the overall yield of NBphen is only 50-70%, and the overall yield of NBphen can reach 89-92% by the method provided by the invention.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Detailed Description
Preferred embodiments of the present invention will be described in more detail below. While the following describes preferred embodiments of the present invention, it should be understood that the present invention may be embodied in various forms and should not be limited by the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.
The invention provides a preparation method of an OLED electron transport material NBphen, which comprises the following steps:
(1) under the existence of protective gas and a first organic solvent, carrying out contact reaction on 2-bromonaphthalene and metal lithium to obtain a 2-lithium naphthalene organic solution;
(2) carrying out contact reaction on a Bphen organic solution and the 2-lithium naphthalene organic solution in the presence of protective gas to obtain a reaction mixture;
(3) carrying out hydrolysis reaction on the reaction mixture and water to obtain an oil-water mixture;
(4) and extracting an organic phase in an aqueous layer of the oil-water mixture, and then carrying out contact reaction on the organic phase and an oxidant to obtain the NBphen.
According to the invention, the Bphen organic solution is preferably subjected to degassing treatment.
According to the present invention, preferably, in step (1), the first organic solvent is at least one of diethyl ether, tetrahydrofuran, benzene, toluene, dichloromethane, chloroform, DMF, and carbon tetrachloride; the first organic solvent is a dried first organic solvent;
the 2-bromonaphthalene is dropwise added into a reaction container in the form of an organic solution of the 2-bromonaphthalene formed by the 2-bromonaphthalene and a first organic solvent; in the organic solution of the 2-bromonaphthalene, the mass ratio of the 2-bromonaphthalene to the first organic solvent is 1: 3-10;
the reaction temperature of the contact reaction is 25-45 ℃, and the reaction time is 1-8 h.
According to the invention, preferably, in the organic solution of 2-bromonaphthalene, the mass ratio of 2-bromonaphthalene to the first organic solvent is 1: 4-5.
In the present invention, in the step (1), the reactant metallic lithium is added in excess, and after the reaction is completed, the excess metallic lithium is removed by filtration.
According to the present invention, preferably, in step (2), the solvent used by the Bphen organic solution is at least one of diethyl ether, tetrahydrofuran, benzene, toluene, dichloromethane, chloroform, DMF and carbon tetrachloride, the solvent is a dry solvent, and the mass ratio of Bphen to the solvent is 1: 3-6;
the molar ratio of the Bphen to the 2-lithium naphthalene is 1:2-5, preferably 1: 2.5;
the contact reaction is carried out for 1-8h at 0 ℃, and then the temperature is raised to 40-60 ℃ for continuous reaction for 8-12 h.
According to the present invention, preferably, the mass ratio of the Bphen to the solvent is 1: 8-10.
According to the present invention, preferably, in step (3), the reaction mixture is cooled to 0 ℃ and then subjected to hydrolysis reaction with water.
In the present invention, in the step (3), water is preferably deionized water, and water is added in excess.
According to the present invention, preferably, in the step (4), the oxidizing agent is manganese dioxide, SeO2At least one of dichlorodicyanobenzoquinone (DDQ) and potassium permanganate; preferably manganese dioxide;
the extraction is carried out with dichloromethane;
the reaction temperature of the contact reaction is 20-50 ℃, and the reaction time is 6-12 h.
In the present invention, in the step (4), the extraction is preferably performed a plurality of times; the oxidant is added in excess; the degree of progress of the reaction of the contact reaction in step (4) is preferably monitored by TLC.
According to the invention, preferably, the protective gas is nitrogen.
In the invention, solid matters are filtered and removed after the reaction is finished, the filtrate is concentrated and then filtered to collect the generated light yellow solid, the light yellow solid is washed by cold ethanol, and the light yellow solid is recrystallized in the ethanol after being dried to obtain the target product.
In the present invention, each raw material for preparing NBphen can be obtained commercially.
According to the preparation method of NBphen, in theory, every 1g of metal lithium sheet is used, 70ml of 2mol/l butyl lithium solution can be replaced, or 90ml of 1.6mol/l butyl lithium solution is used, under the laboratory condition, a special reaction container is not needed, 5-10 g of metal lithium scale reaction can be conveniently operated, 30-60 g of NBphen product is prepared each time, the raw material cost is reduced, and pilot scale amplification is conveniently carried out. If a reaction kettle is used for operation, the preparation scale can be improved to kilogram level only by simply scaling up.
The invention is further illustrated by the following examples:
the synthetic route of the reaction of the following examples is shown in formula I.
Example 1
The embodiment provides a preparation method of an OLED electron transport material NBphen, which specifically comprises the following steps:
(1) under the protection of nitrogen, adding a dried ether solution (30ml) of 2-bromonaphthalene (8.28g, 40mmol) into a 100ml round-bottom flask containing 1.3g of sheared metallic lithium pieces and 20ml of dried ether through a dropping funnel at 25 ℃ within 2h, continuing stirring at 25 ℃ for 2h after dropping is finished, and filtering to remove solid matters such as residual metallic lithium pieces and the like to obtain a 2-lithium naphthalene organic solution;
(2) dissolving Bphen (3.32g, 10mmol) in 20ml of dry ether, degassing for three cycles, cooling to 0 ℃ with ice water bath, adding the 2-lithium naphthalene organic solution through a dropping funnel within 1.5h under the protection of nitrogen, continuing to react for 1h after dropping is finished, and heating to 40 ℃ for 30min and keeping for 8h to obtain a reaction mixture;
(3) cooling the reaction mixture to room temperature, further cooling to 0 ℃ by using an ice water bath, then adding 20ml of deionized water for three times in 20min, and stirring for 30min to obtain an oil-water mixture;
(4) after separating the oil-water mixture, the aqueous layer was extracted with dichloromethane (25 ml. times.3), the organic phases were combined and 50g of activated manganese dioxide was added and stirred at 25 ℃ for 10 h. After the reaction is finished, black solid is removed by filtration, the filtrate is concentrated and then filtered to collect the generated light yellow solid, the light yellow solid is washed by cold ethanol, and the light yellow solid is recrystallized in ethanol after being dried to obtain the target product NBphen5.39g with the yield of 92.1%.1H NMR(600MHz,CDCl3)9.03(s,2H),8.79-8.81(dd,2H),8.31(s,2H),8.11-8.13(dd,2H),8.08-8.10(m,2H),7.95-7.96(m,2H),7.88(s,2H),7.67(d,2H),7.65-7.66(m,2H),7.54-7.62(m,10H)。
Example 2
(1) Under the protection of nitrogen, dropwise adding a dried ether solution (100ml) of 2-bromonaphthalene (20.70g, 100mmol) into a 500ml round-bottom flask containing 3.3g of sheared metallic lithium pieces and 60ml of dried ether at 25 ℃ for 4h through a dropping funnel, refluxing at 40 ℃ for 2h after dropwise adding is finished, and filtering to remove solid matters such as residual metallic lithium pieces to obtain a 2-lithium naphthalene organic solution;
(2) dissolving Bphen (13.28g, 40mmol) in 60ml of dry toluene, degassing for three cycles, cooling to 0 ℃ with an ice water bath, adding the 2-lithium naphthalene organic solution through a dropping funnel within 2h under the protection of nitrogen, continuing to react for 2h after dropping is finished, and heating to 45 ℃ for 30min and keeping for 12h to obtain a reaction mixture;
(3) cooling the reaction mixture to room temperature, further cooling to 0 ℃ by using an ice water bath, then adding 50ml of deionized water in total for three times within 45min, and stirring for 1h to obtain an oil-water mixture;
(4) after separating the oil-water mixture, the aqueous layer was extracted with dichloromethane (50 ml. times.3), the organic phases were combined and 200g of activated manganese dioxide was added and stirred at 40 ℃ for 8 h. After the reaction was completed, black was removed by filtrationAnd (3) concentrating the filtrate, filtering and collecting the generated light yellow solid, washing the light yellow solid by using cold ethanol, drying and recrystallizing in ethanol to obtain the target product NBphen20.95g with the yield of 89.5%.1H NMR(600MHz,CDCl3)9.03(s,2H),8.79-8.81(dd,2H),8.31(s,2H),8.11-8.13(dd,2H),8.08-8.10(m,2H),7.95-7.96(m,2H),7.88(s,2H),7.67(d,2H),7.65-7.66(m,2H),7.54-7.62(m,10H)。
Example 3
(1) Under the protection of nitrogen, dropwise adding a dried THF solution (250ml) of 2-bromonaphthalene (62.20g, 300mmol) into a 500ml round-bottom flask containing 10g of chopped metal lithium pieces and 100ml of dried THF through a dropping funnel at 25 ℃ within 4h, continuously stirring for 1h at 25 ℃, heating to 45 ℃ and continuously stirring for 3h, and filtering to remove solid matters such as residual metal lithium pieces and the like to obtain a 2-lithium naphthalene organic solution;
(2) dissolving Bphen (39.85g, 120mmol) in 200ml of dry THF, degassing for three cycles, cooling to 0 ℃ with ice water bath, adding the 2-lithium naphthalene organic solution through a dropping funnel within 3h under the protection of nitrogen, continuing to react for 4h after dropping is finished, heating to 60 ℃ after the reaction is finished for 30min, and keeping for 12h to obtain a reaction mixture;
(3) cooling the reaction mixture to room temperature, further cooling to 0 ℃ by using an ice water bath, then adding 120ml of deionized water in total for three times within 45min, and stirring for 3h to obtain an oil-water mixture;
(4) after separating the oil-water mixture, the aqueous layer was extracted with dichloromethane (150 ml. times.3), the organic phases were combined and 600g of activated manganese dioxide was added and stirred at 45 ℃ for 12 h. After the reaction is finished, black solid is removed by filtration, the filtrate is concentrated and then the generated light yellow solid is collected by filtration, washed by cold ethanol, dried and recrystallized twice in ethanol to obtain the target product NBphen 62.55g with the yield of 89.1%.1H NMR(600MHz,CDCl3)9.03(s,2H),8.79-8.81(dd,2H),8.31(s,2H),8.11-8.13(dd,2H),8.08-8.10(m,2H),7.95-7.96(m,2H),7.88(s,2H),7.67(d,2H),7.65-7.66(m,2H),7.54-7.62(m,10H)。
Example 4
(1) Under the protection of nitrogen, dropwise adding a dried carbon tetrachloride solution (50ml) of 2-bromonaphthalene (10.35g, 50mmol) into a 250ml round-bottom flask containing 1.7g of sheared metallic lithium pieces and 10ml of dried carbon tetrachloride through a dropping funnel within 2h at 25 ℃, continuously stirring for 2h at 35 ℃ after dropwise adding is finished, and filtering to remove solid matters such as residual metallic lithium pieces and the like to obtain a 2-lithium naphthalene organic solution;
(2) dissolving Bphen (4.32g, 13mmol) in 30ml of dry toluene, degassing for three cycles, cooling to 0 ℃ by using an ice water bath, adding the 2-lithium naphthalene organic solution through a dropping funnel within 1h under the protection of nitrogen, continuing to react for 2h after dropping is finished, heating to 45 ℃ after the reaction is finished for 30min, and keeping for 9h to obtain a reaction mixture;
(3) cooling the reaction mixture to room temperature, further cooling to 0 ℃ by using an ice water bath, then adding 30ml of deionized water in three times within 30min, and stirring for 1h to obtain an oil-water mixture;
(4) after separating the oil-water mixture, the aqueous layer was extracted with dichloromethane (40 ml. times.3), the organic phases were combined and added to a mixed solution of 50g potassium permanganate in 400ml acetone/water (3:1, v: v) and stirred for 8h at 25 ℃. After the reaction is finished, black solids are removed by filtration, the filtrate is concentrated and then dissolved in 100ml of dichloromethane again, the mixture is washed for 3 times by saturated sodium thiosulfate solution, the mixture is concentrated to 20ml on a rotary evaporator and placed in a low-speed centrifuge (4000r/min) for 4min, light yellow solids at the bottom of a centrifugal tube are collected, the mixture is washed by cold ethanol, and the product is recrystallized in ethanol after being dried, so that the target product NBphen 6.89g is obtained, and the yield is 90.5%.1H NMR(600MHz,CDCl3)9.03(s,2H),8.79-8.81(dd,2H),8.31(s,2H),8.11-8.13(dd,2H),8.08-8.10(m,2H),7.95-7.96(m,2H),7.88(s,2H),7.67(d,2H),7.65-7.66(m,2H),7.54-7.62(m,10H)。
Having described embodiments of the present invention, the foregoing description is intended to be exemplary, not exhaustive, and not limited to the embodiments disclosed. Many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the described embodiments.
Claims (10)
1. A preparation method of an OLED electron transport material NBphen is characterized by comprising the following steps:
(1) under the existence of protective gas and a first organic solvent, carrying out contact reaction on 2-bromonaphthalene and metal lithium to obtain a 2-lithium naphthalene organic solution; the first organic solvent is at least one of diethyl ether, tetrahydrofuran, benzene, toluene, dichloromethane, chloroform, DMF and carbon tetrachloride;
(2) carrying out contact reaction on a Bphen organic solution and the 2-lithium naphthalene organic solution in the presence of protective gas to obtain a reaction mixture; the solvent used by the Bphen organic solution is at least one of diethyl ether, tetrahydrofuran, benzene, toluene, dichloromethane, chloroform, DMF and carbon tetrachloride;
(3) carrying out hydrolysis reaction on the reaction mixture and water to obtain an oil-water mixture;
(4) extracting an organic phase in a water layer of the oil-water mixture, and then carrying out contact reaction on the organic phase and an oxidant to obtain the NBphen; the oxidant is manganese dioxide and SeO2At least one of dichlorodicyanobenzoquinone and potassium permanganate.
2. The production method according to claim 1, wherein the Bphen organic solution is a degassed Bphen organic solution.
3. The production method according to claim 1, wherein, in the step (1), the first organic solvent is a dried first organic solvent;
the 2-bromonaphthalene is dropwise added into a reaction container in the form of an organic solution of the 2-bromonaphthalene formed by the 2-bromonaphthalene and a first organic solvent; in the organic solution of the 2-bromonaphthalene, the mass ratio of the 2-bromonaphthalene to the first organic solvent is 1: 3-10;
the reaction temperature of the contact reaction is 25-45 ℃, and the reaction time is 1-8 h.
4. The preparation method according to claim 3, wherein in the organic solution of 2-bromonaphthalene, the mass ratio of 2-bromonaphthalene to the first organic solvent is 1: 4-5.
5. The production method according to claim 1, wherein in the step (2), the solvent is a dried solvent, and the mass ratio of Bphen to the solvent is 1: 3-6;
the molar ratio of the Bphen to the 2-lithium naphthalene is 1: 2-5;
the contact reaction is carried out for 1-8h at 0 ℃, and then the temperature is raised to 40-60 ℃ for continuous reaction for 8-12 h.
6. The preparation method according to claim 5, wherein the mass ratio of the Bphen to the solvent is 1: 8-10.
7. The production method according to claim 1, wherein, in the step (3), the reaction mixture is cooled to 0 ℃ and then subjected to hydrolysis reaction with water.
8. The production method according to claim 1, wherein, in the step (4), the extraction is performed with dichloromethane;
the reaction temperature of the contact reaction is 20-50 ℃, and the reaction time is 6-12 h.
9. The production method according to claim 8, wherein the oxidizing agent is manganese dioxide.
10. The production method according to claim 1, wherein the protective gas is nitrogen.
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| WO2018206138A1 (en) * | 2017-05-08 | 2018-11-15 | Cynora Gmbh | Organic electroluminescent device |
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