CN113831292A - Organic electron transport material containing benzimidazole and anthracene and application thereof - Google Patents

Organic electron transport material containing benzimidazole and anthracene and application thereof Download PDF

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CN113831292A
CN113831292A CN202111200908.3A CN202111200908A CN113831292A CN 113831292 A CN113831292 A CN 113831292A CN 202111200908 A CN202111200908 A CN 202111200908A CN 113831292 A CN113831292 A CN 113831292A
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electron transport
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transport material
anthracene
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苏艳
王宜凡
周海涛
赵振宏
张大庆
黄珠菊
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Shanghai Chuanqin New Material Co ltd
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Abstract

The invention relates to the technical field of organic electroluminescence, in particular to an organic electron transport material containing benzimidazole and anthracene and application thereof. The structure of the compound is shown in a structural formula I,
Figure DDA0003302435300000011
wherein Ar is1Is C6‑C30Substituted unsubstituted aryl, C3‑C30One of substituted or unsubstituted heteroaryl; ar (Ar)2Is cyanophenyl, pyridyl, pyrimidinyl or quinolinyl; l is1And L2Is phenyl, biphenyl or naphthyl; r1‑R12Is one of hydrogen, deuterium, methyl, trideuteromethyl, trifluoromethyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, cyano, chlorine, fluorine and bromine.

Description

Organic electron transport material containing benzimidazole and anthracene and application thereof
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 benzimidazole and anthracene 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.
Benzimidazole groups have long been used as electron transport materials in organic electroluminescent devices, and in 1998 Shi et al reported in US5766779 benzimidazole electron transport materials and WO2004080975 reported the combination of benzimidazole and anthracene as electron transport materials. With the increasing demand for OLEDs, there is also a need to develop electron transport materials with better stability and electron transport properties.
The invention content is as follows:
the invention aims at the problems and provides an organic electron transport material containing benzimidazole and anthracene and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme that cyanophenyl or pyridyl is introduced into the position 2 of benzimidazole to enhance the electronegativity of the material, improve the electron transport performance of the compound, simultaneously improve the glass transition temperature of the compound and improve the thermal stability of the material, and the structure of the material is shown as the structural formula I,
Figure BDA0003302435280000031
structural formula I
Wherein Ar is1Is C6-C30Substituted unsubstituted aryl, C3-C30One of substituted or unsubstituted heteroaryl; ar (Ar)2Is cyanophenyl, pyridyl, pyrimidinyl or quinolinyl; l is1And L2Is phenyl, biphenyl or naphthyl;
R1-R12is one of hydrogen, deuterium, methyl, trideuteromethyl, trifluoromethyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, cyano, chlorine, fluorine and bromine.
Ar1Preferably one of phenyl, 1-naphthyl, 2-naphthyl, biphenyl, phenanthryl, 9, 9-dimethylfluorenyl, 9, 9-diphenylfluorenyl, 9, 9-spirofluorenyl, benzophenanthryl, dibenzofuranyl, dibenzothienyl, phenylnaphthyl, naphthylphenyl, pyridyl and benzonitrile.
Ar2Preferably a pyridyl group, a benzonitrile group.
L1And L2Preferably phenyl.
Preferably, the organic electronic material containing benzimidazole and anthracene includes, but is not limited to, any one of the following compounds 1 to 46,
Figure BDA0003302435280000032
Figure BDA0003302435280000041
Figure BDA0003302435280000051
Figure BDA0003302435280000061
Figure BDA0003302435280000071
Figure BDA0003302435280000081
Figure BDA0003302435280000091
Figure BDA0003302435280000101
the organic electronic material containing benzimidazole and anthracene can be applied to an organic electroluminescent device and comprises an anode, a cathode and an organic layer, wherein the organic layer comprises more than 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.
At least one of the organic layers contains the organic electronic material.
The light-emitting layer in the organic layer contains the organic electronic material.
The electron transport layer or the electron injection layer in the organic layer contains the organic electronic material.
The hole blocking layer in the organic layer contains the organic electronic material.
An organic metal complex can be added into the electron transport layer containing the organic electronic material, wherein the content of the metal complex is 20-70%. The organometallic complex can be lithium 8-hydroxyquinoline.
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 device may 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. The metal electrode can be prepared by an evaporation method or a sputtering method.
In addition to organic electroluminescent devices, the above organic electronic materials containing benzimidazole and anthracene may 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 benzimidazole and anthracene, which has good electron transport performance due to the benzimidazole group; the introduction of anthracene groups can improve the thermal stability of the material; meanwhile, the cyanophenyl or pyridyl is introduced into the 2-position of the benzimidazole, so that the electronegativity of the material can be enhanced, the electron transport performance of the material can be 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:
FIG. 1 is a hydrogen nuclear magnetic spectrum of Compound 1 in example 1.
Fig. 2 is a hydrogen nuclear magnetic spectrum of compound 3 in example 2.
Fig. 3 is a schematic structural diagram of an organic electroluminescent device.
Wherein 110 represents a glass substrate, 120 represents an anode, 130 represents a hole injection layer, 140 represents a hole transport layer, 150 represents a blocking layer, 160 represents a light emitting layer, 170 represents an electron transport layer, 180 represents an electron injection layer, and 190 represents 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.
Example 1
Synthesis of Compound 1
Figure BDA0003302435280000121
Synthesis of intermediate 1-1
In a flask, a bromobenzimidazole compound (10.00g, 26.179mmol), 4-cyanobenzene boronic acid (6.89g, 31.415mmol), potassium carbonate (10.80g, 78.142mmol), bis (triphenylphosphine) palladium dichloride (0.2g), toluene 60mL, ethanol 30mL and water 30mL were added, stirred in a 250mL flask, protected with nitrogen, and heated under reflux at 85 ℃ for 5 hours. After the reaction, the reaction mixture was cooled to 25 ℃ and filtered, the solid was washed with ethanol and recrystallized from toluene to obtain 8.6g of a product with a yield of 81.29%.
Synthesis of Compound 1
The flask was charged with intermediate 1-1(6.5g,16mmol), 9-phenyl-10-anthraceneboronic acid (5.3g,17.7mmol), potassium carbonate (5.67g, 41.02mmol), bis (triphenylphosphine) palladium dichloride (0.10g), X-phos (0.2g), toluene 40mL, ethanol 20mL and water 20mL, under nitrogen, and heated at 85 ℃ under reflux for 5 hours. After the reaction, the reaction mixture was cooled to 25 ℃, filtered, and the crude product was recrystallized from toluene to give 6.6g of product, with a yield of 66.2%.
1H NMR(400MHz,CDCl3δ 7.99-8.01(d, J ═ 7.2Hz,1H), 7.89-7.91(d, J ═ 8.0Hz,2H), 7.36-7.75(m,26H), as in fig. 1.
MS(ESI,m/z):[M+H]+:624.19。
Example 2
Figure BDA0003302435280000131
Compound 3 was synthesized in 74% yield, different from Compound 1 of example 1, by substituting 9- (2-naphthyl) -10-phenylboronic acid for 9-phenyl-10-anthraceneboronic acid.
1H NMR(400MHz,CDCl3δ) 7.90-8.11(m,7H), 7.54-7.78(m,18H), 7.36-7.45(m,6H), as shown in FIG. 2.
MS(ESI,m/z):[M+H]+:674.28。
Example 3
Figure BDA0003302435280000132
Synthesis of intermediate 39-1
The synthesis method is different from the intermediate 1-1 in that 3-cyanobenzene boronic acid is replaced by 3-pyridine boronic acid pinacol ester, and the yield is 67%.
Synthesis of Compound 39
The synthesis method is different from the compound 1 in that the raw materials are the intermediate 39-1 and 9- (2-naphthyl) -10-phenylboronic acid, and the yield is 54%.
1H NMR(400MHz,CDCl3,δ):7.91-8.51(m,6H)，7.41-7.83(m,12H)，7.26-7.38(m,13H)。
MS(ESI,m/z):[M+H]+:650.30。
The effects of the compounds of the present invention are described in detail below by way of examples.
The structure of the organic electroluminescent device is shown in fig. 3, 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 to Ag mass ratio 10: 1).
Example 4
Preparation of an OLED Using Compound 1 of 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.
Then, the glass substrate with the anode is placed in a vacuum chamber, vacuum pumping is carried out, HIL (5nm) is evaporated on the ITO to be used as a hole injection layer 130, and the evaporation rate is 0.1 nm/s.
A compound HT1 was deposited on the hole injection layer to form a hole transport layer 140 with a thickness of 80nm at a rate of 0.1 nm/s. EB was deposited on the hole transport layer to form an electron blocking layer 150 having a thickness of 10nm at a deposition rate of 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. An equal mass of compound 1 and LiQ 30nm thick was deposited on the light-emitting layer as the electron transport layer 170 at a deposition rate of 0.1 nm/s. LiQ having a thickness of 1nm was deposited 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 difference from example 4 is that compound 1 in step (6) is replaced with compound 3 as an electron transporting material.
Example 6
The difference from example 4 is that compound 1 in step (6) is replaced with compound 39 as an electron transporting material.
Comparative example 1
The only difference from example 4 is that compound 1 in step (6) is replaced by compound ET as the electron transporting material.
The structural formula in the device is as follows:
Figure BDA0003302435280000151
Figure BDA0003302435280000161
the organic materials are all known materials and are obtained by market purchase.
The prepared device is measured by a Photo Research PR650 spectrometer to be 1000cd/m2Working voltage, efficiency, CIE coordinates, and measurement at 30mA/cm2The time (T96) at which the luminance became 96% of the initial luminance at the current density is shown in table 1.
TABLE 1 device Performance parameters
Figure BDA0003302435280000162
Figure BDA0003302435280000171
As can be seen from Table 1, the voltage of the organic electroluminescent device prepared by using the electron transport material of the present invention is reduced, the efficiency is improved by at least 17%, the voltage is reduced by nearly 20%, and the service life is improved by at least 34%. The compound of the invention shows good performance, because of the introduction of the benzene nitrile group and the pyridyl group, the electronegativity of the material is favorably increased, the electron mobility of the material is improved, the balance of holes and electrons of a device is facilitated, the electrons can be effectively transmitted to a light-emitting layer, and the performance of the device is further improved.
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 (10)

1. An organic electron transport material containing benzimidazole and anthracene and its application, which is characterized in that its structure is shown in formula I,
Figure FDA0003302435270000011
wherein Ar is1Is C6-C30Substituted unsubstituted aryl, C3-C30One of substituted or unsubstituted heteroaryl; ar (Ar)2Is cyanophenyl, pyridyl, pyrimidinyl or quinolinyl; l is1And L2Is phenyl, biphenyl or naphthyl;
R1-R12hydrogen, deuterium, methyl, trideuteromethyl, trifluoromethyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, cyano,chlorine, fluorine and bromine.
2. The benzimidazole-and-anthracene-containing organic electron transport material of claim 1, wherein Ar is Ar1Is one of phenyl, 1-naphthyl, 2-naphthyl, biphenyl, phenanthryl, 9, 9-dimethylfluorenyl, 9, 9-diphenylfluorenyl, 9, 9-spirofluorenyl, benzophenanthryl, dibenzofuranyl, dibenzothienyl, phenylnaphthyl, naphthylphenyl, pyridyl and benzonitrile group.
3. The benzimidazole-and-anthracene-containing organic electron transport material of claim 1, wherein Ar is Ar2Is pyridyl and benzonitrile.
4. The use of the organic electron transport material according to claim 1, wherein the organic electron transport material comprises an anode, a cathode, and an organic layer, and the organic layer comprises at least one of a light emitting layer, a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron injecting layer, and an electron transporting layer.
5. The use of an organic electron transport material comprising benzimidazole and anthracene according to claim 4, wherein at least one of the organic layers comprises the organic electron material.
6. The use of the organic electron transport material according to claim 5, wherein the light-emitting layer of the organic layer contains the organic electron material.
7. The use of the organic electron transport material according to claim 5, wherein the electron transport layer or the electron injection layer of the organic layer contains the above organic electron material.
8. The use of an organic electron transport material according to claim 5, wherein the hole blocking layer in the organic layer comprises the above organic electron material.
9. The use of the organic electron transport material containing benzimidazole and anthracene according to claim 7, wherein an organic metal complex is further added into the electron transport layer, wherein the content of the metal complex is 20-70%. The organometallic complex can be lithium 8-hydroxyquinoline.
10. Use of the benzimidazole and anthracene-containing organic electron transport material according to claim 4, wherein the benzimidazole and anthracene-containing organic electron material is further applicable to organic solar cells, organic thin film transistors, organic photodetectors, organic field effect transistors, organic integrated circuits, and organic photoreceptors.
CN202111200908.3A 2021-10-13 2021-10-13 Organic electron transport material containing benzimidazole and anthracene and application thereof Pending CN113831292A (en)

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Application publication date: 20211224