CN114044779A - Organic electron transport material containing benzodioxan and application thereof - Google Patents
Organic electron transport material containing benzodioxan and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of organic electroluminescence, in particular to an organic electron transport material containing benzodioxole and application thereof. The structural formula is shown as the following structural formula (I),
Ar1and Ar2Is C6‑C30Substituted or unsubstituted aryl of, C3‑C30Substituted or unsubstituted heteroaryl of (a); z1、Z2And Z3At least one of them is N, the others are CH; l is C6‑C30Substituted or unsubstitutedAryl group of (1).
Description
The technical field is as follows:
the invention relates to the technical field of organic electroluminescence, in particular to an organic electron transport material containing benzodioxole and application thereof.
Background art:
organic electroluminescent devices (OLEDs), as a new display technology, can be switched freely for each pixel and emit light actively, resulting in short display response time and high color contrast; the driving voltage is low, and the energy consumption can be reduced; the use of organic materials enables the device to be thinner and lighter and environment-friendly; the diversified selection of the substrate provides possibility for flexible and transparent display, and the substrate is widely applied to the fields of mobile phones, flat panel displays, televisions, lighting, vehicle-mounted display and the like.
The common organic electroluminescent device adopts a sandwich type sandwich structure, namely an organic layer is sandwiched between an anode and a cathode at two sides, and the organic layer is divided into a hole transport layer, an electron transport layer, a luminescent layer, a hole blocking layer, an electron blocking layer and the like according to different photoelectric characteristics of various materials. The light-emitting mechanism of the device is mainly as follows: under the drive of external voltage, holes and electrons overcome energy barriers, are respectively injected into the hole transport layer and the electron transport layer from the anode and the cathode, then are recombined in the light-emitting layer to release energy, and the energy is transferred to the organic light-emitting substance. The light-emitting substance receives energy and is caused to transition from a ground state to an excited state, and when excited molecules transition back to the ground state, a light-emitting phenomenon occurs.
The electron transport material is a material for transporting electrons on the cathode to the luminescent layer, is an important component of the organic electroluminescent device, is beneficial to reducing the injection energy barrier of the electrons, and can also avoid the phenomenon that the cathode is contacted with the luminescent layer to cause luminescence quenching. Electron transport materials generally require good thermal stability and film-forming properties, high electron mobility, high electron affinity, and high excited state energy levels.
Since most organic electroluminescent materials transport holes faster than electrons. This causes an imbalance in the number of electrons and holes in the light-emitting layer, resulting in a device emitting light away from the light-emitting layer and closer to the electrodes, which requires higher driving voltages and also reduces the efficiency and lifetime of the device. Although recent organic electroluminescent devices have been gradually improved, materials more excellent in light emitting efficiency, driving voltage, lifespan, and the like are required, and thus, development of an electron transport material having good thermal stability and excellent performance is required.
Tris (8-hydroxyquinoline) aluminum, TBPi, Bphen include other azoles, phenanthroline and other compounds have been used as electron transport materials in organic electroluminescent devices. Pyridine group should be widely used in Organic electroluminescent devices due to its strong electron transport property and hole blocking property, Kido et al end a series of electron transport materials (adv. func. mater, 2011,21,36) containing pyridine group, Aamer saued et al introduced the use of pyridine in blue light materials, and also introduced the characteristics of pyridine-based electron transport materials (Mini-Reviews in Organic Chemistry,2018,15, 261-. Patent (WO2011115163) describes the application of a polypyridyl substituted benzene compound as an electron transport material, and the patent introduces the application of pyridine and triazine combined as an electron transport material on an organic electroluminescent device. With the increasing demand of OLEDs, there is also a need to develop electron transport materials having excellent thermal stability, film-forming properties and electron transport properties.
The invention content is as follows:
the invention aims at the problems and provides an organic electron transport material containing benzodioxan bipyridyl with high thermal stability, film forming property and strong electron mobility and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme that the benzodioxole is introduced to improve the thermal stability and the film forming property of the electronic transmission material containing the pyridyl, increase the conjugated system of the material and enhance the electron mobility of the material, and the structural formula of the electronic transmission material is shown as the following structural formula (I),
Ar1and Ar2Is C6-C30Substituted or unsubstituted aryl of, C3-C30Is substituted orUnsubstituted heteroaryl;
Z1、Z2and Z3At least one of them is N, the others are CH;
l is C6-C30Substituted or unsubstituted aryl of (a).
Preferably, Ar1And Ar2Is phenyl, tolyl, biphenyl, naphthyl, phenanthryl, anthracyl, perylenyl, phenylnaphthyl, naphthylphenyl, diphenylphenyl, 9, 9-dimethylfluorenyl, 9, 9-diphenylfluorenyl, 9, 9-spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl or benzophenanthryl, pyridyl or aryl-substituted anthracyl.
Preferably, L is phenyl, biphenyl, binaphthyl, phenylnaphthyl, 9, 9-dialkylfluorenyl, arylphenyl or anthracenyl.
More preferably, the organic electronic material comprises any one of the following compounds ET1-ET 30.
The organic electronic material can be used for preparing an organic electroluminescent device, and the organic electroluminescent device comprises an anode, a cathode and an organic layer.
The organic layer comprises more than one of a luminescent layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer and an electron transport layer.
At least one of the organic layers contains an organic electronic material of the structural formula I.
Preferably, the electron transport layer or the electron injection layer in the organic layer contains the organic electronic material of the structural formula I.
Preferably, the hole blocking layer in the organic layer contains the organic electronic material.
When the above organic electronic material is used as an electron transporting material, an organic metal complex, such as lithium 8-hydroxyquinoline, may be doped, wherein the doping amount of the metal complex is 20 to 70 wt%.
The total thickness of the organic layer is 1-1000 nm; further preferably, the total thickness of the organic layer is 50 to 500 nm.
Each of the organic layers in the organic electroluminescent element of the present invention can be prepared by a vacuum evaporation method, a molecular beam evaporation method, a dip coating method in a solvent, a spin coating method, a bar coating method, or an inkjet printing method, and for the metal electrode, an evaporation method or a sputtering method can be used.
The organic electronic material can also be applied to organic solar cells, organic thin film transistors, organic photodetectors, organic field effect transistors, organic integrated circuits and organic photoreceptors.
The invention has the beneficial effects that:
the invention provides an organic electron transport material containing benzodioxan pyridine, and the compound has good electron transport performance and thermal stability due to the benzodioxan pyridine group; meanwhile, the pyridyl group is linked with the triazine derivative, so that the electronegativity of the material is enhanced, the electron transmission performance of the material is improved, and the stability of the material can also be improved. The organic electroluminescent material is applied to an organic electroluminescent device as an electron transport material, can improve the high luminous efficiency of the device, and prolongs the service life of the device.
Description of the drawings:
figure 1 is a hydrogen nuclear magnetic spectrum of ET2 prepared in example 1.
Fig. 2 is a schematic structural view of an organic electroluminescent device, wherein 110 is a glass substrate, 120 is an anode, 130 is a hole injection layer, 140 is a hole transport layer, 150 is a blocking layer, 160 is a light emitting layer, 170 is an electron transport layer, 180 is an electron injection layer, and 190 is a cathode.
The specific implementation mode is as follows:
the present invention will be further described with reference to the accompanying drawings and detailed description, but the following embodiments are only preferred embodiments of the present invention, and not all embodiments. Based on the embodiments in the implementation, other embodiments obtained by those skilled in the art without any creative efforts belong to the protection scope of the present invention.
Synthesis of intermediates
Synthesis of intermediate 1
10g of 2-chloro-3, 5-dibromopyridine, 4.1g of o-diphenol, 24g of cesium carbonate and 80mL of DMF were poured into a 250mL three-necked flask, heated to 140 ℃ and mechanically stirred. After 4h of reaction, the reaction was completed by spotting. Poured into water, extracted with dichloromethane, dried, concentrated, the crude product recrystallized from toluene, filtered and dried to yield 8.16g of product, yield 84%.
Synthesis of intermediate 2
10.13g of intermediate 1,11.7g of pinacol diborate and 0.2g of Pd (PPh) are successively added3)2Cl211.31g of potassium acetate are crushed, poured into a 250mL three-necked flask, poured into 130mL of dioxane, reacted for 3 hours under nitrogen, cooled, poured into water, extracted with dichloromethane, dried, concentrated, the crude product is recrystallized from toluene, filtered and the yield is 90%.
EXAMPLE 1 Synthesis of Compound ET2
5.95g of intermediate 2, 7.65g of chlorophenylbiphenyl triazine, 3.78g of potassium carbonate, 0.08g of Pd (OAc)20.16g of x-phos, 25mL of deionized water, 25mL of ethanol and 50mL of toluene were added to a 250mL three-necked flask; heating and refluxing for 2 hours under the protection of nitrogen, cooling, filtering, recrystallizing a filter cake with toluene, and drying7.1g of the product are obtained in 69% yield.1H NMR(400MHz,CDCl3,δ):8.79-8.93(m,6H),8.22(s,1H),7.42-7.83(m,13H),6.95-7.03(m,4H)。
Example 2 Synthesis of Compound ET20
Synthesis of intermediate 3
In a flask, 5g of 1, 4-dibromonaphthalene, 5.5g of intermediate 2, 5g of potassium carbonate, 60mL of toluene, 30mL of ethanol, 30mL of water, 0.2g of tetratriphenylphosphine palladium, and heating under reflux for 5 hours under nitrogen protection were added, and the mixture was cooled, extracted with dichloromethane, dried, and concentrated, and the crude product was purified by column chromatography to give 3.9g, 57% yield.
Synthesis of Compound ET20
The synthesis was the same as intermediate 3, using 3g of intermediate 3 and 3.5g of 2, 6-diphenyltriazine-6-phenylboronic acid pinacol ester, 85% yield.
1H NMR(400MHz,CDCl3,δ):8.81-8.94(m,6H),8.35-8.37(m,1H),7.47-7.89(m,15H),6.95-7.07(m,4H)。
EXAMPLE 3 Synthesis of Compound ET24
The synthesis was carried out as for intermediate 3, starting from 2.7g of intermediate 2 and 4.5g of 2- [ 3-chloro-5- (9-phenanthryl) -phenyl ] -2, 4, 6-triazine in 63% yield.
1H NMR(400MHz,CDCl3,δ):9.04(s,1H),8.96(s,1H),8.77-8.86(m,6H),8.30-8.31(m,1H),7.95-7.99(m,3H),7.97(s,1H),7.57-7.76(m,11H),6.92-7.04(m,4H)。
The effects of the compounds of the present invention are described in detail below by way of examples.
The preparation of the organic electroluminescent device and the structural schematic diagram are shown in fig. 2, and the specific device structure is as follows: glass/anode (ITO)/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/Electron Blocking Layer (EBL)/light emitting layer (host material BH: blue light emitting material BD)/electron transport layer (electron transport material: 8-hydroxyquinoline lithium)/Electron Injection Layer (EIL)/cathode (Mg: Ag,10: 1).
Example 4
An OLED was prepared using ET2 prepared in example 1.
The transparent conductive ITO glass substrate 110 (with the anode 120 on top) (south glass group ltd, china) was sonicated in a commercial detergent, rinsed in deionized water, sequentially washed with ethanol, acetone and deionized water, baked in a clean environment to completely remove moisture, cleaned with ultraviolet photosynthetic ozone, and treated with oxygen plasma for 30 seconds.
The glass substrate with the anode is placed in a vacuum chamber, vacuum pumping is carried out, HIL (5nm) is evaporated on ITO to be used as a hole injection layer 130, and the evaporation rate is 0.1 nm/s.
Evaporating compound HT on the hole injection layer to form 80nm thick hole transport layer 140 with evaporation rate of 0.1nm/s,
EB was deposited on the dummy transport layer to form an electron blocking layer 150 having a thickness of 10 nm. The evaporation rate was 0.1 nm/s.
A light-emitting layer 160 with a thickness of 30nm was deposited on the hole-blocking layer, wherein BH was the host light-emitting material and BD was 2% by weight as the doping guest material, and the deposition rate was 0.1 nm/s.
50% by weight of compound ET2 and 50% by weight of LiQ as electron transport layer 170 were deposited on the light-emitting layer to a thickness of 30 nm. The evaporation rate is 0.1nm/s,
depositing LiQ with a thickness of 1nm on the electron transport layer as an electron injection layer 180
And (3) evaporating a 100nm thick doping ratio on the electron injection layer to be 10:1 as the device cathode 190.
Example 5
The only difference from example 4 is that compound ET2 in step (6) was replaced by compound ET12 as electron transporting material.
Example 6
The only difference from example 4 is that compound ET2 in step (6) was replaced by compound ET24 as electron transporting material.
Comparative example 1
The only difference from mutexample 4 is that compound ET2 in step (6) is replaced by compound ET-a as electron transport material.
The structural formula in the device is as follows:
the organic materials are all known materials and are obtained by market purchase.
The prepared device was measured at 1000cd/m with a Photo Research PR655 spectrometer2Working voltage, efficiency, CIE coordinates, and measurement at 30mA/cm2The time (T90) at which the luminance at the current density became 90% of the initial luminance is shown in table 1.
TABLE 1 device Performance parameters
As can be seen from Table 1, the voltage of the organic electroluminescent device prepared by the electron transport material of the invention is reduced, the current efficiency is improved from 6.83cd/A to 7.93-8.98cd/A, and the voltage is reduced by 0.2-0.4V. At 30mA/cm2The current density of T90 is increased from 69 hours to 87-98 hours, and the service life is greatly improved. The compound of the invention shows good performance, because the introduction of benzodioxan pyridine is beneficial to increasing the stability of the material and improving conjugation, improving the electron mobility of the material, helping the balance of holes and electrons of the device, effectively transmitting the electrons to a light-emitting layer and further improving the performance of the device.
The foregoing detailed description of the preferred embodiments of the invention has been presented. It should be understood that numerous modifications and variations could be devised by those skilled in the art in light of the present teachings without departing from the inventive concepts. Therefore, the technical solutions available to those skilled in the art through logic analysis, reasoning and limited experiments based on the prior art according to the concept of the present invention should be within the scope of protection defined by the claims.
Claims (9)
1. An organic electron transport material containing benzodioxopyridine is characterized in that the structural formula is shown as the following structural formula (I),
Ar1and Ar2Is C6-C30Substituted or unsubstituted aryl of, C3-C30Substituted or unsubstituted heteroaryl of (a);
Z1、Z2and Z3At least one of them is N, the others are CH;
l is C6-C30Substituted or unsubstituted aryl of (a).
2. The benzodioxaepin-containing organic electron transport material according to claim 1, wherein Ar is Ar1And Ar2Is phenyl, tolyl, biphenyl, naphthyl, phenanthryl, anthracyl, perylenyl, phenylnaphthyl, naphthylphenyl, diphenylphenyl, 9, 9-dimethylfluorenyl, 9, 9-diphenylfluorenyl, 9, 9-spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl or benzophenanthryl, pyridyl or aryl-substituted anthracyl.
3. The benzodioxopyridine-containing organic electron transport material according to claim 1, wherein L is a phenyl group, a biphenyl group, a binaphthyl group, a phenylnaphthyl group, a 9, 9-dialkylfluorenyl group, an arylphenyl group or an anthracenyl group.
4. Use of the benzodioxaepin-containing organic electron transport material of claim 1 for the preparation of an organic electroluminescent device comprising an anode, a cathode and an organic layer.
5. The use of an organic electron transport material comprising benzodioxaepin according to claim 4, wherein the organic layer comprises at least one of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and an electron transport layer.
6. The use of an organic electron transport material comprising benzodioxaepins according to claim 5 wherein at least one of the organic layers comprises an organic electron material of formula I.
7. The use of the benzodioxaepin-containing organic electron transport material according to claim 6, wherein the electron transport layer or the electron injection layer in the organic layer comprises the organic electron material of formula I.
8. The use of an organic electron transport material comprising benzodioxaepin according to claim 7 wherein the hole blocking layer in the organic layer comprises the organic electron material.
9. The use of the benzodioxaepin-containing organic electron transport material according to claim 4, wherein the organic electronic material is further applicable to organic solar cells, organic thin film transistors, organic photodetectors, organic field effect transistors, organic integrated circuits, and organic photoreceptors.
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| CN1829706A (en) * | 2003-06-25 | 2006-09-06 | 日产化学工业株式会社 | 1,4-benzodioxane sulfonic acid compound and use thereof as electron-acceptor material |
| CN107406760A (en) * | 2015-03-09 | 2017-11-28 | 保土谷化学工业株式会社 | Luminescent material and organic electroluminescence device |
| CN109516923A (en) * | 2017-09-18 | 2019-03-26 | 东进世美肯株式会社 | Compounds and organic luminescent device comprising it |
| KR20200076004A (en) * | 2018-12-18 | 2020-06-29 | 두산솔루스 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
| KR20200076002A (en) * | 2018-12-18 | 2020-06-29 | 두산솔루스 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
| CN111362959A (en) * | 2018-12-25 | 2020-07-03 | 江苏三月光电科技有限公司 | Compound with olefinic bond-containing fluorene as core and application thereof |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1829706A (en) * | 2003-06-25 | 2006-09-06 | 日产化学工业株式会社 | 1,4-benzodioxane sulfonic acid compound and use thereof as electron-acceptor material |
| CN107406760A (en) * | 2015-03-09 | 2017-11-28 | 保土谷化学工业株式会社 | Luminescent material and organic electroluminescence device |
| CN109516923A (en) * | 2017-09-18 | 2019-03-26 | 东进世美肯株式会社 | Compounds and organic luminescent device comprising it |
| KR20200076004A (en) * | 2018-12-18 | 2020-06-29 | 두산솔루스 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
| KR20200076002A (en) * | 2018-12-18 | 2020-06-29 | 두산솔루스 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
| CN111362959A (en) * | 2018-12-25 | 2020-07-03 | 江苏三月光电科技有限公司 | Compound with olefinic bond-containing fluorene as core and application thereof |
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