CN114702489A

CN114702489A - Organic electronic material containing phenanthrene and phenanthroline and application thereof

Info

Publication number: CN114702489A
Application number: CN202210363765.6A
Authority: CN
Inventors: 苏艳; 周海涛; 吴海发; 黄泽甜; 谢启燕; 张亮; 黄珠菊
Original assignee: Shanghai Chuanqin New Material Co ltd
Current assignee: Shanghai Chuanqin New Material Co ltd
Priority date: 2022-04-07
Filing date: 2022-04-07
Publication date: 2022-07-05
Also published as: WO2023193775A8; WO2023193775A1

Abstract

The invention relates to the technical field of organic electroluminescence, in particular to an organic electronic material containing phenanthrene and phenanthroline and application thereof. The specific structural formula is shown as the following formula I,

in the formula I, R₁And R₂At least one is one of substituted or unsubstituted pyridyl, benzonitrile, fluorophenyl and trifluorophenyl, and the other is hydrogen, deuterium, cyano, C₁‑C₁₀Substituted or unsubstituted alkyl, C₆‑C₃₀Substituted or unsubstituted aryl, C₃‑C₃₀One of substituted or unsubstituted heteroaryl; l is one of a single bond, substituted or unsubstituted aryl and heteroaryl; r₃Is hydrogen, deuterium, C₁‑C₁₀Substituted or unsubstituted alkyl, C₆‑C₃₀Substituted or unsubstituted aryl, C₃‑C₃₀One of substituted or unsubstituted heteroaryl; n is an integer of 1 to 6.

Description

Organic electronic material containing phenanthrene and phenanthroline and application thereof

The technical field is as follows:

the invention relates to the technical field of organic electroluminescence, in particular to an organic electronic material containing phenanthrene and phenanthroline 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.

Phenanthroline compound Bphen

And BCP

The compound has been applied to organic electroluminescent devices as an electron transport material, but the stability, particularly the glass transition temperature, of Bphen and BCP is lower, and the application of the phenanthroline compound is influenced. 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 electronic material containing phenanthrene and phenanthroline, which has high thermal stability, film-forming property and strong electron mobility, and an application thereof.

In order to achieve the purpose, the invention adopts the following technical scheme that the thermal stability and the film forming property of the material are improved through the substituted phenanthrene group, and meanwhile, the pyridine and benzonitrile groups are introduced to increase the electron mobility of the material, and the specific structural formula is shown as the following formula I,

in the formula I, the raw materials are shown in the specification,

R₁and R₂At least one is one of substituted or unsubstituted pyridyl, benzonitrile, fluorophenyl and trifluorophenyl, and the other is hydrogen, deuterium, cyano, C₁-C₁₀Substituted or unsubstituted alkyl, C₆-C₃₀Substituted or unsubstituted aryl, C₃-C₃₀One of substituted or unsubstituted heteroaryl;

l is one of a single bond, substituted or unsubstituted aryl and heteroaryl;

R₃is hydrogen, deuterium, C₁-C₁₀Substituted or unsubstituted alkyl, C₆-C₃₀Substituted or unsubstituted aryl, C₃-C₃₀One of substituted or unsubstituted heteroaryl;

n is an integer of 1 to 6.

L is preferably a single bond, phenyl, naphthyl or biphenyl.

R₃Preferably hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, phenyl, tolyl, biphenyl or naphthyl.

More preferably, the phenanthrene-and phenanthroline-containing organic electronic material includes, but is not limited to, any one of the following compounds 1 to 120.

The organic electronic material containing phenanthrene and phenanthroline can be applied to an organic electroluminescent device, and 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 or an electron transport layer; at least one of the organic layers contains an organic electronic material of formula I above.

Preferably, the electron transport layer or the electron injection layer in the organic layer contains the organic electronic material of formula I.

Preferably, the hole blocking layer in the organic layer contains the organic electronic material.

In addition to the compound of formula I, the electron transport layer may be doped with an organometallic complex, such as lithium 8-hydroxyquinoline, wherein the doping content of the metal complex is 20-70%.

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, and for the metal electrode, an evaporation method or a sputtering method may be used.

The organic electronic material shown in the formula I can also be used for producing organic solar cells, organic thin film transistors, organic photodetectors, organic field effect transistors, organic integrated circuits or organic photoreceptors.

The invention has the beneficial effects that:

the invention provides an organic electron transport material containing phenanthrene and phenanthroline, and the phenanthrene containing substituent groups improves the thermal stability of the compound, improves the film-forming property of the material by improving the thermal stability, and reduces the form deterioration of a semiconductor layer of a prepared device. And meanwhile, phenanthroline groups are introduced, and pyridyl and benzonitrile groups are introduced into phenanthrene, so that the electron transport performance of the material is improved, and the material can be applied to a blue organic electroluminescent device as an electron transport material, so that the high luminous efficiency of the device can be improved, and the service life of the device can be prolonged, which is important for reducing the power consumption of mobile display equipment and prolonging the service life of a battery.

Description of the drawings:

FIG. 1 is a DSC of Compound 1.

FIG. 2 is a DSC of Compound 11.

FIG. 3 is a DSC of compound 61.

Figure 4 is a DSC diagram of compound 72.

Figure 5 is a DSC diagram of compound 91.

Fig. 6 is a schematic view of a device structure.

FIG. 7 is a graph of voltage versus current density for devices made from compounds of the present invention.

FIG. 8 is a graph of current density versus current efficiency for devices made with the compounds of the present invention.

Figure 9 is a graph of current density versus power efficiency for devices prepared from compounds of the present invention.

The specific implementation mode is as follows:

EXAMPLE 1 Synthesis of Compound 1

1. Synthesis of intermediate 1-1

2-chloro-9-iodo-10-phenylphenanthrene (10.0g, 24.12mmol), 4-cyanophenylboronic acid (5.3g, 36.07mmol) potassium carbonate (10.0g, 72.35mmol) were added to a three-necked flask, toluene (100mL), ethanol (50mL) and deionized water (50mL) were added, and Pd (PPh) was added under nitrogen protection₃)₂Cl₂(0.2g), refluxing for 12h, separating, concentrating the organic phase to about 30mL, stirring for crystallization, filtering, leaching and drying to obtain 7.4g of gray solid product with the yield of 79%. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₂₇H₁₆ClN,389.0971,found 389.0975.

2. Synthesis of intermediate 1-2

Adding the intermediate 1-1(7.0g, 17.95mmol), pinacol diborate (5.47g, 21.54mmol), potassium acetate (5.29g, 53.90mmol) and anhydrous toluene (70mL) into a three-neck flask, adding Pd (PPh3)2Cl2(0.14g) under the protection of nitrogen, refluxing for 6h, filtering while hot, concentrating to be nearly dry, adding ethanol (30mL), stirring, filtering, leaching with ethanol, and drying to obtain 7.8g of a product with the yield of 90%. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₃₃H₂₉BNO₂,482.2286,found 482.2284.

3. Synthesis of Compound 1

Adding 2- (3-bromophenyl) -1, 10-phenanthroline (0.5g, 1.49mmol), intermediate 1-2(0.75g, 1.58mmol) and potassium carbonate (0.41g, 2.97mmol) into a three-neck flask, adding toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), and adding Pd (PPh) under the protection of nitrogen₃)₂Cl₂(0.01g), after refluxing for 8h, cooling and separating, concentrating the organic phase to dryness, separating by column chromatography, DCM/CH₃OH (10/1) gave 0.63g of product in 69% yield. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₄₅H₂₈N₃,610.2278,found 610.2273.Anal.:calcd:C,88.64；H,4.46；N,6.89；found:C,88.58；H,4.49；N,6.88.

Example 2 Synthesis of Compounds

Adding 2- (4-bromophenyl) -1, 10-phenanthroline (0.5g, 1.49mmol), intermediate 1-2(0.75g, 1.58mmol) and potassium carbonate (0.41g, 2.97mmol) into a three-neck flask, adding toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), and adding Pd (PPh) under the protection of nitrogen gas₃)₂Cl₂(0.01g), after refluxing for 8h, cooling and separating, concentrating the organic phase to dryness, separating by column chromatography, DCM/CH₃OH (10/1) gave 0.58g of product in 63% yield. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₄₅H₂₈N₃,610.2278,found 610.2279.Anal.:calcd:C,88.64；H,4.46；N,6.89；found:C,88.61；H,4.53；N,6.82.

EXAMPLE 3 Synthesis of Compound 11

Adding 2-bromo-1, 10-phenanthroline (0.5g, 1.93mmol), intermediate 1-2(0.98g, 2.04mmol) and potassium carbonate (0.53g, 3.83mmol) into a three-neck flask, adding toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), and adding Pd (PPh) under the protection of nitrogen₃)₂Cl₂(0.01g), after refluxing for 8h, cooling and separating, concentrating the organic phase to dryness, separating by column chromatography, DCM/CH₃OH (10/1) gave 0.57g of product in 55% yield. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₃₉H₂₄N₃,534.1965,found534.1963.Anal.:calcd:C,87.78；H,4.34；N,7.87；found:C,87.73；H,4.41；N,7.81.

EXAMPLE 4 Synthesis of Compound 41

1. Synthesis of intermediate 41-1

2-chloro-9-iodo-10-phenylphenanthrene (10.0g, 24.12mmol), 3-cyanophenylboronic acid (5.3g, 36.07mmol), potassium carbonate (10.0g, 72.35mmol) were added to a three-necked flask, toluene (100mL), ethanol (50mL) and deionized water (50mL) were added, and Pd (PPh) was added under nitrogen protection₃)₂Cl₂(0.2g), refluxing for 10h, separating, concentrating the organic phase to about 30mL, stirring for crystallization, filtering, leaching and drying to obtain 8.1g of gray solid product with the yield of 86%. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₂₇H₁₆ClN,389.0971,found 389.0977.

2. Synthesis of intermediate 41-2

Adding the intermediate 41-1(7.0g, 17.95mmol), pinacol diborate (5.47g, 21.54mmol), potassium acetate (5.29g, 53.90mmol) and anhydrous toluene (70mL) into a three-neck flask, adding Pd (PPh3)2Cl2(0.14g) under the protection of nitrogen, refluxing for 5h, filtering while hot, concentrating to be nearly dry, adding ethanol (30mL), stirring, filtering, rinsing with ethanol, and drying to obtain 7.9g of a product with the yield of 91%. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₃₃H₂₉BNO₂,482.2286,found 482.2287.

3. Synthesis of Compound 41

Adding 2-bromo-9-phenyl-1, 10-phenanthroline (0.5g, 1.49mmol), intermediate 41-2(0.75g, 1.58mmol) and potassium carbonate (0.41g, 2.97mmol) into a three-neck flask, adding toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), and adding Pd (PPh) under the protection of nitrogen gas₃)₂Cl₂(0.01g), after refluxing for 8h, cooling and separating, concentrating the organic phase to dryness, separating by column chromatography, DCM/CH₃OH (10/1) gave 0.64g of product in 70% yield. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₄₅H₂₈N₃,610.2278,found 610.2280.Anal.:calcd:C,88.64；H,4.46；N,6.89；found:C,88.66；H,4.39；N,6.90.

EXAMPLE 5 Synthesis of Compound 61

1. Synthesis of intermediate 61-1

2-chloro-9-iodo-10-phenylphenanthrene (10.0g, 24.12mmol), 3-pyridineboronic acid ester (7.42g, 36.18mmol), potassium carbonate (10.0g, 72.35mmol) were added to a three-necked flask, toluene (100mL), ethanol (50mL) and deionized water (50mL) were added, and Pd (PPh) was added under nitrogen protection₃)₂Cl₂(0.2g), refluxing for 15h, separating, concentrating the organic phase to about 30mL, stirring for crystallization, filtering, leaching and drying to obtain 7.3g of gray solid product with the yield of 83%. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₂₅H₁₆ClN,365.0971,found 365.0973.

2. Synthesis of intermediate 61-2

Adding the intermediate 61-1(7.0g, 19.13mmol), pinacol diborate (5.83g, 22.96mmol), potassium acetate (5.63g, 57.37mmol) and anhydrous toluene (70mL) into a three-neck flask, adding Pd (PPh3)2Cl2(0.14g) under the protection of nitrogen, refluxing for 8h, filtering while hot, concentrating to be nearly dry, adding ethanol (30mL), stirring, filtering, eluting with ethanol, and drying to obtain 8.1g of a product with the yield of 92%. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₃₁H₂₉BNO₂,458.2286,found 458.2284.

3. Synthesis of Compound 61

Adding 2- (3-bromophenyl) -1, 10-phenanthroline (0.5g, 1.49mmol), intermediate 61-2(0.72g, 1.57mmol) and potassium carbonate (0.41g, 2.97mmol) into a three-neck flask, adding toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), and adding Pd (PPh) under the protection of nitrogen gas₃)₂Cl₂(0.01g), refluxing for 10h, cooling, separating, concentrating the organic phase to dryness, separating by column chromatography, and purifying with DCM/CH₃OH (10/1) gave 0.60g of product in 68% yield. HRMS (ESI, M/z): [ M + H]⁺calculated for C₄₃H₂₈N₃,586.2278,found 583.2275.Anal.:calcd:C,88.18；H,4.65；N,7.17；found:C,88.26；H,4.59；N,7.12.

EXAMPLE 6 Synthesis of Compound 72

Adding 2-bromo-9-phenyl-1, 10-phenanthroline (0.5g, 1.49mmol), intermediate 61-2(0.72g, 1.57mmol) and potassium carbonate (0.41g, 2.97mmol) into a three-neck flask, adding toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), and adding Pd (PPh) under the protection of nitrogen gas₃)₂Cl₂(0.01g), after refluxing for 10h, cooling and separating, concentrating the organic phase to dryness, separating by column chromatography, DCM/CH₃OH (10/1) gave 0.57g of product in 65% yield. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₄₃H₂₈N₃,586.2278,found 583.2274.Anal.:calcd:C,88.18；H,4.65；N,7.17；found:C,88.12；H,4.69；N,7.15.

EXAMPLE 7 Synthesis of Compound 91

1. Synthesis of intermediate 91-1

2-chloro-9-iodo-10-phenylphenanthrene (10.0g, 24.12mmol), 4-pyridineboronic acid ester (7.42g, 36.18mmol), potassium carbonate (10.0g, 72.35mmol) were added to a three-necked flask, toluene (100mL), ethanol (50mL) and deionized water (50mL) were added, and Pd (PPh) was added under nitrogen protection₃)₂Cl₂(0.2g), refluxing and reacting for 20h, separating, concentrating the organic phase to about 30mL, stirring and crystallizing, filtering, leaching and drying to obtain 7.1g of gray solid product with the yield of 80%. HRMS (ESI, M/z) [ M ]]⁺calculated for C₂₅H₁₆ClN,365.0971,found 365.0968.

2. Synthesis of intermediate 91-2

Adding the intermediate 91-1(7.0g, 19.13mmol), pinaboronate diborate (5.83g, 22.96mmol), potassium acetate (5.63g, 57.37mmol) and anhydrous toluene (70mL) into a three-neck flask, adding Pd (PPh3)2Cl2(0.14g) under the protection of nitrogen, refluxing for 8h, filtering while hot, concentrating to be nearly dry, adding ethanol (30mL), stirring, filtering, rinsing with ethanol, and drying to obtain 7.9g of a product with the yield of 90%. HRMS (ESI, M/z): [ M + H]⁺calculated for C₃₁H₂₉BNO₂,458.2286,found 458.2281.

3. Synthesis of Compound 91

Adding 2- (3-bromophenyl) -1, 10-phenanthroline (0.5g, 1.49mmol), an intermediate 91-2(0.72g, 1.57mmol) and potassium carbonate (0.41g, 2.97mmol) into a three-neck flask, adding toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), and adding Pd (PPh) under the protection of nitrogen gas₃)₂Cl₂(0.01g), refluxing for 10h, cooling, separating, concentrating the organic phase to dryness, separating by column chromatography, and purifying with DCM/CH₃OH (10/1) gave 0.55g of product in 63% yield. HRMS (ESI, M/z): [ M + H]⁺calculated for C₄₃H₂₈N₃,586.2278,found 583.2272.Anal.:calcd:C,88.18；H,4.65；N,7.17；found:C,88.14；H,4.69；N,7.13.

EXAMPLE 8 Synthesis of Compound 102

Adding 2-bromo-9-phenyl-1, 10-phenanthroline (0.5g, 1.49mmol), intermediate 91-2(0.72g, 1.57mmol) and potassium carbonate (0.41g, 2.97mmol) into a three-neck flask, adding toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), and adding Pd (PPh) under the protection of nitrogen gas₃)₂Cl₂(0.01g), refluxing for 10h, cooling, separating, concentrating the organic phase to dryness, separating by column chromatography, and purifying with DCM/CH₃OH (10/1) gave 0.61g of product in 70% yield. HRMS (ESI, M/z) [ M + H ]]⁺calculated for C₄₃H₂₈N₃,586.2278,found 583.2277.Anal.:calcd:C,88.18；H,4.65；N,7.17；found:C,88.15；H,4.71；N,7.10.

The performance of the compounds was also tested.

The glass transition temperature (Tg) of the compound was measured by a differential scanning calorimeter (Pyrs Diamond (DSC 2920)) under nitrogen protection at a heating and cooling rate of 10 deg.C/min.

TABLE 1 glass transition temperature of the materials

As can be seen from Table 1 and FIGS. 1-5, the glass transition temperature of the compound of the present invention reached 118-161 ℃ which is greatly improved over BCP and Bphen, indicating that the compound has good thermal stability.

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. 6, and the specific device structure is as follows: glass/anode (ITO)/Hole Injection Layer (HIL)/Hole Transport Layer (HTL)/Electron Blocking Layer (EBL)/emissive layer (EML), host material BH blue emissive material BD, 97: 3)/electron transport layer (ETL, electron transport material 8-hydroxyquinoline lithium, 50: 50)/Electron Injection Layer (EIL)/cathode (Mg: Ag,9:1)

Example 9

An OLED was prepared using compound 1 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.

A compound HT is evaporated on the hole injection layer to form a hole transport layer 140 with a thickness of 80nm, the evaporation rate is 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 by evaporation, wherein BH was the host light-emitting material and BD was 3% by weight as the dopant guest material, and the deposition rate was 0.1 nm/s.

50% by weight of Compound 1 and 50% by weight of LiQ as an electron transport layer 170 were deposited on the light-emitting layer to a thickness of 35 nm. The evaporation rate was 0.1 nm/s.

LiQ having a thickness of 1nm was deposited on the electron transport layer as an electron injection layer 180.

And evaporating a 100nm thick doping ratio on the electron injection layer to be 9:1 as the device cathode 190.

Examples 10 to 16

The difference from example 9 is only that compound 1 of the electron transport material is replaced by another compound of the present invention, and the specific device structure is as shown in table 1 below.

Comparative example 1

The only difference from example 9 is that compound 1 of the electron transport material was replaced by comparative compound BCP. The specific device structure is shown in table 1 below.

The structural formula in the device is as follows:

the organic materials are all known materials and are obtained by market purchase.

TABLE 1 device Structure

Testing the performance of the device:

the prepared device was measured for operating voltage, current efficiency, emission spectrum, and power efficiency using a Photo Research PR655 spectrometer at 20mA/cm²The luminance decays to 95% of the original luminance lifetime at the current density (T95). FIG. 7 is a graph showing the relationship between voltage and current density of examples 9 to 14, FIGS. 8 and 9 are graphs showing the relationship between current density and efficiency of examples 9 to 14, and Table 2 is a graph showing the relationship between voltage and current density at 20mA/cm²Voltage and efficiency at current density and lifetime, as shown in table 2.

TABLE 2 device Performance parameters

As can be seen from table 2 and fig. 7 to 9, compared to comparative example 1, the device of the present invention prepared by using phenanthrene and phenanthroline-based compounds as electron transport materials has significantly improved current efficiency and power efficiency, reduced voltage at the same current density, and significantly improved lifetime. The compound of the present invention shows excellent properties, and the properties of the amorphous thin film enhance the properties 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

1. An organic electronic material containing phenanthrene and phenanthroline, which is characterized in that the specific structural formula is shown as the following formula I,

in the formula I, the compound has the following structure,

l is one of a single bond, substituted or unsubstituted aryl and heteroaryl;

n is an integer of 1 to 6.

2. The phenanthrene-and phenanthroline-containing organic electronic material of claim 1, wherein L is a single bond, phenyl, naphthyl, or biphenyl.

3. The phenanthrene-and phenanthroline-containing organic electronic material of claim 1, wherein R is₃Hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, phenyl, tolyl, biphenyl, or naphthyl.

4. The use of the phenanthrene-and phenanthroline-containing organic electronic material of claim 1 in an organic electroluminescent device comprising an anode, a cathode, and an organic layer.

5. The use of the phenanthrene-and-phenanthroline-containing organic electronic material 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; at least one of the organic layers contains an organic electronic material of formula I above.

6. The use of the phenanthrene-and phenanthroline-containing organic electronic material according to claim 5, wherein the electron transport layer or the electron injection layer contains the organic electronic material of formula I.

7. The use of the phenanthrene-and phenanthroline-containing organic electronic material of claim 5, wherein the hole blocking layer comprises the organic electronic material of formula I.

8. The use of the phenanthrene-and phenanthroline-containing organic electronic material according to claim 5, wherein each of the organic layers can be prepared by vacuum evaporation, molecular beam evaporation, solvent-soluble dip coating, spin coating, bar coating, or inkjet printing, and for the metal electrode, evaporation or sputtering can be used.

9. The use of the phenanthrene-and phenanthroline-containing organic electronic material according to claim 4, wherein the organic electronic material of formula I is also used for producing organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits or organic photoreceptors.