CN114685427B - Quinoline bipyridine compound and application thereof in organic electroluminescent element - Google Patents

Quinoline bipyridine compound and application thereof in organic electroluminescent element Download PDF

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CN114685427B
CN114685427B CN202011589759.XA CN202011589759A CN114685427B CN 114685427 B CN114685427 B CN 114685427B CN 202011589759 A CN202011589759 A CN 202011589759A CN 114685427 B CN114685427 B CN 114685427B
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quinoline
electron transport
bipyridine compound
organic electroluminescent
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CN114685427A (en
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叶子勤
孙霞
王仁宗
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Changzhou Tronly New Electronic Materials Co Ltd
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Chan N Changzhou Tronly Eray Optoelectroincs Material Co ltd
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Abstract

The invention provides a quinoline bipyridine compound and application thereof in an organic electroluminescent element. The quinoline bipyridine compound has a structure shown in the following formula A:wherein Ar is 1 And Ar is a group 2 Identical or different and each independently selected from C 6 ～C 30 Unsubstituted aryl or heteroaryl groups of (a). When the quinoline bipyridine compound is used as an electron transport material in an organic electroluminescent device, the luminous efficiency can be effectively improved, and the service life of the device can be prolonged.

Description

Quinoline bipyridine compound and application thereof in organic electroluminescent element
Technical Field
The invention relates to the field of electron transport materials, in particular to a quinoline bipyridine compound and application thereof in an organic electroluminescent element.
Background
The organic electroluminescent element (organic light emitting diodes, OLED) has advantages of light weight, thin thickness, self-luminescence, low power consumption, no backlight source, wide viewing angle, fast response, flexibility, etc., has gradually replaced the liquid crystal display panel to become a new generation of flat panel display, and has great potential in flexible display. Carrier mobility (carrier mobility) of conventional electron transport materials is one thousandth of that of hole transport materials, and thermal stability is poor, often resulting in problems of rapid roll-off of light emission efficiency or poor device lifetime. The relevant literature indicates that the electron transport material occupies a charge consumption ratio of 35.9%, which is inferior to the consumption of the light emitting layer (39.8%). Therefore, development of an electron transport material with high carrier mobility and good thermal stability is one of the key points of current OLED material development.
Good electron transport materials are generally required to meet the following characteristics: (1) LUMO energy levels matched to the light emitting layer to facilitate electron transfer; (2) Lower than the HOMO energy level of the light emitting layer to facilitate confinement of excitons in the light emitting layer; (3) The triplet energy level T1 which is high enough to match with the phosphorescent material is matched, so that exciton quenching is avoided; (4) an amorphous phase, avoiding light scattering; (5) good thermal stability and high glass transition temperature.
The electron transport materials commonly used at present mainly comprise metal complexes, nitrogen-containing heterocyclic compounds, perfluorinated compounds, organic silicon compounds, organic boron compounds and the like. Among them, the nitrogen-containing heterocyclic compound is a structure which is studied more, and the Chinese patent application with the application publication number of CN102165622A discloses a4, 4' -bipyridine compound, the specific structure is as follows:
the doped metal complex is used as an electron transport layer of the red organic phosphorescent element, so that on one hand, the electron transport efficiency can be improved, and on the other hand, compared with a linear nitrogen heterocyclic bridging structure, the service life of the red organic phosphorescent element is obviously improved. Currently, the hole mobility of the hole transport material in the existing OLED device is generally far greater than the electron mobility of the electron transport material, and this imbalance in carrier transport rate can bring about a significant decrease in device performance. And therefore possess better electron mobility to be able to efficiently transport electrons to the recombination zone remote from the cathode. In addition, the electron transport material has better film forming property, otherwise, a uniform film cannot be formed during vapor deposition, crystallization is easy to generate, and the efficiency and the service life of a device are seriously affected. Therefore, the performance of the electron transport material has yet to be further optimized to achieve low voltage, high efficiency and long lifetime of the device.
Disclosure of Invention
The invention mainly aims to provide a quinoline bipyridine compound and an organic electroluminescent element, which are used for solving the problem of thermal stability of a4, 4-bipyridine compound in the prior art and prolonging the service life of a device.
In order to achieve the above object, according to one aspect of the present invention, there is provided a quinoline bipyridine compound having a structure represented by the following formula a:
wherein Ar is 1 And Ar is a group 2 Identical or different and each independently selected from C 6 ～C 30 Unsubstituted aryl or heteroaryl groups of (a).
Further, ar is as described above 1 And Ar is a group 2 Identical, is selected from C 10 ～C 18 Aryl or heteroaryl groups of (a).
Further, ar is as described above 1 And Ar is a group 2 Different, is selected from C 6 ～C 30 Aryl or heteroaryl groups of (a).
Further, ar is as described above 1 And Ar is a group 2 Selected from biphenyl, naphthyl, anthryl, phenanthryl, dimethylfluorenyl, dibenzofuranyl or dibenzothiophenyl.
Further, ar is as described above 1 And Ar is a group 2 Selected from phenyl, biphenyl, naphthyl, anthryl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl or spirobifluorenyl.
Further, the quinoline bipyridine is selected from any one of the following:
according to another aspect of the present invention, there is also provided an application of the above quinoline bipyridine compound as an electron transport material in an organic electroluminescent element.
By applying the technical scheme of the invention, different aryl or heteroaryl groups can be introduced at the ortho position of N atoms in the quinoline bipyridine compound, the molecular weight of the compound is increased, on one hand, the HOMO energy level and the LUMO energy level of the material can be regulated, on the other hand, the steric hindrance can be increased, the crystallization trend of the material can be inhibited, and the thermal stability can be improved, so that the service life of the device is obviously improved when the quinoline bipyridine compound is applied as an electron transport material in an organic electronic light-emitting element.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention. In the drawings:
fig. 1 shows a schematic structure of an organic electroluminescent device provided in embodiment 1 of the device according to the present invention.
Wherein the above figures include the following reference numerals:
1. a substrate layer; 2. a hole injection layer; 3. a hole transport layer; 4. a light emitting layer; 5. an electron transport layer; 6. and a cathode layer.
Detailed Description
It should be noted that, in the case of no conflict, the embodiments and features in the embodiments may be combined with each other. The invention will be described in detail below with reference to the drawings in connection with embodiments.
The advantageous effects of the present application will be further described below in conjunction with examples and comparative examples.
First, the synthetic method of the quinoline bipyridine compound of the present application is exemplified below.
Synthetic examples
1. Synthesis of intermediates
1.1 Synthesis of intermediate M1
2, 4-dichloropquinoline (9.9 g,50 mmol), 2-naphthaleneboronic acid (8.77 g,51 mmol), 150mL toluene, potassium carbonate (13.82 g,100 mmol), 50mL water, 50mL ethanol were charged into a 500mL round bottom flask, stirred under nitrogen to raise the temperature to 50℃and 0.58g catalyst Pd (PPh) 3 ) 4 And continuously heating to reflux reaction for 4 hours, stopping the reaction, cooling, separating liquid, adding 50mL of water into an organic phase, washing twice, heating toluene, decolorizing by using a short silica gel column, then steaming the toluene until the rest of the toluene is about 50mL, heating to 80 ℃ for complete dissolution, adding 200mL of ethanol, stirring, cooling, precipitating solid, filtering and drying to obtain 12g of white solid compound M1, wherein the yield is 83%. Intermediate M1 was further recrystallized twice by the same method to a purity of 99.2%.
1.2 Synthesis of intermediate M2
Into a 500mL round bottom flask, compound M1 (15 g,51.7 mmol), bis-pinacolato borate (14.4 g,56.9 mmol), 200mL toluene, 6.6g potassium acetate was added, stirring was continued and the temperature was increased to 50℃under nitrogen, and 0.29g catalyst Pd (dba) was added 2 And 0.48g of 2-di-tert-butylphosphine-2 ',4',6' -triisopropylbiphenyl, continuously heating to reflux for 6 hours, stopping the reaction, decoloring the organic phase by using a short silica gel column while the organic phase is hot, then rotationally evaporating toluene, cooling, adding 20mL of dichloromethane, heating to 40 ℃ for complete dissolution, adding 150mL of n-hexane, stirring, cooling, precipitating solid, filtering and drying to obtain 15g of white solid compound M2, wherein the yield is 76.1%. The purity was 99.31%.
1.3 Synthesis of intermediate M3
2, 4-dichloroquinoline (9.9 g,50 mmol), 9-dimethylfluorene-2-boronic acid (1)2.14g,51 mmol), 150mL toluene, potassium carbonate (13.82 g,100 mmol), 50mL water, 50mL ethanol were added to a 500mL round bottom flask, stirred under nitrogen to raise the temperature to 50℃and 0.58g catalyst Pd (PPh) 3 ) 4 And continuously heating to reflux reaction for 4 hours, stopping the reaction, cooling, separating liquid, adding 50mL of water into an organic phase, washing twice, heating toluene, decolorizing by using a short silica gel column, then steaming the toluene until the rest of the toluene is about 50mL, heating to 80 ℃ for complete dissolution, adding 200mL of ethanol, stirring, cooling, precipitating solid, filtering and drying to obtain 15g of white solid compound M3, wherein the yield is 84%. Intermediate M3 was further recrystallized twice by the same method to a purity of 99.5%.
1.4 Synthesis of intermediate M4
Intermediate M3 (36.8 g,103.4 mmol), bis-pinacolato borate (28.8 g,113.8 mmol), 500mL toluene, 13.2g potassium acetate were added to a 1000mL round bottom flask, stirred under nitrogen to warm to 50℃and 0.59g catalyst Pd (dba) was added 2 And 0.95g of 2-di-tert-butylphosphine-2 ',4',6' -triisopropylbiphenyl, continuously heating to reflux for 6 hours, stopping the reaction, decoloring the organic phase by using a short silica gel column while the organic phase is hot, then rotationally evaporating toluene, cooling, adding 50mL of dichloromethane, heating to 40 ℃ for complete dissolution, adding 300mL of n-hexane, stirring, cooling, precipitating a solid, filtering and drying to obtain 38.8g of white solid compound M4, wherein the yield is 79%. The purity is 99.1%.
1.5 Synthesis of intermediate M5
2,4, 6-trichloropyridine (37.24 g,204.6 mmol), phenylboronic acid (49 g,402 mmol), 400mL of tetrahydrofuran, sodium carbonate (85 g,800 mmol), 400mL of water were added to a 1000mL round bottom flask, stirred under nitrogen to raise the temperature to 40℃and 2.9g of catalyst PdCl were added 2 (PPh 3 ) 2 Continuously heating to reflux reaction for 3h, stopping the reaction, cooling, separating liquid, and rotating organic phaseAfter drying, 500mL of toluene was added and heated to a short silica gel column for decolorization, toluene was then distilled off by spin, 200mL of ethanol was added and heated to 80 ℃ for complete dissolution, and then the solid was separated out by stirring and cooling, and the solid was obtained by filtration and drying, thus 39.7g of a white solid compound M5 was obtained, and the yield was 73%. Intermediate M5 was further recrystallized once by the same method to a purity of 99.3%.
1.6 Synthesis of intermediate M6
2,4, 6-trichloropyridine (18.24 g,100 mmol), 2-naphthaleneboronic acid (36.12 g,210 mmol), 300mL toluene, sodium carbonate (31.8 g,300 mmol), 150mL water, 100mL ethanol were charged into a 1000mL round bottom flask, stirred under nitrogen to raise the temperature to 50℃and 3.4g catalyst Pd (PPh) 3 ) 4 And continuously heating to reflux reaction for 8 hours, stopping the reaction, cooling, filtering and separating liquid, washing an organic phase twice with 100mL of water, filtering, merging the organic phases, adding 500mL of toluene, heating to decolorize with a short silica gel column, then steaming out toluene to 100mL, stirring, cooling, precipitating solid, filtering and drying to obtain 28.5g of white solid compound M6, and the yield is 78%. Intermediate M6 was further recrystallized twice by the same method to a purity of 99.6%.
1.7 Synthesis of intermediate M7
2,4, 6-trichloropyridine (27.4 g,150 mmol), 9-dimethylfluorene-2-boronic acid (73.2 g,307.5 mmol), 450mL toluene, sodium carbonate (63.6 g,600 mmol), 300mL water, 300mL ethanol were added to a 2000mL round bottom flask, stirred under nitrogen to raise the temperature to 50℃and 5.2g of catalyst Pd (PPh) 3 ) 4 Continuously heating to reflux reaction for 8h, stopping the reaction, cooling, filtering, separating liquid, washing the organic phase with 300mL of water twice, filtering, combining the organic phases, adding 800mL of toluene, heating to over short silica gel column for decoloring, then steaming toluene to 150mL, heating to complete dissolution, adding 500mL of ethanol, stirring, cooling, and precipitating solidFiltration and drying gave 56g of compound M7 as a white solid in 75% yield. Intermediate M7 was further recrystallized twice by the same method to a purity of 99.1%.
1.8 Synthesis of intermediate M8
2,4, 6-trichloropyridine (18.24 g,100 mmol), dibenzofuran-2-boronic acid (41.7 g, 197mmol), 300mL toluene, sodium carbonate (42.4 g,400 mmol), 200mL water, 100mL ethanol were added to a 1000mL round bottom flask, the temperature was raised to 50℃with stirring under nitrogen, and 3.4g of catalyst Pd (PPh) 3 ) 4 And continuously heating to reflux reaction for 8 hours, stopping the reaction, cooling, filtering and separating liquid, washing an organic phase with 100mL of water twice, filtering, merging the organic phases, adding 800mL of toluene, heating to a short silica gel column for decoloring, then rotationally steaming out the toluene to 200mL, stirring, cooling, precipitating solid, filtering and drying to obtain 38.3g of white solid compound M8, wherein the yield is 86%. Intermediate M8 was further recrystallized twice by the same method to a purity of 99.7%.
2. Synthesis of target Compound
2.1 Synthesis of Compound A4
Into a 250mL round bottom flask, intermediate M2 (8.92 g,20 mmol), intermediate M6 (21 mmol), 80mL tetrahydrofuran, potassium carbonate (5.53 g,40 mmol) and 20mL water were added, and the mixture was stirred under nitrogen to 40℃and 45mg of catalyst Pd (OAc) was added 2 And (3) continuously heating 0.19g of 2-di-tert-butylphosphine-2 ',4',6' -triisopropylbiphenyl to reflux for 6 hours, stopping the reaction, cooling, filtering and separating liquid, rotationally drying an organic phase, combining with filtration, adding 500mL of toluene, heating to a short silica gel column for decoloring, then evaporating the toluene until solid is separated out, stirring and cooling to room temperature, and filtering and drying to obtain a white solid compound A4. After the compound A4 is recrystallized twice by the same method, the purity is more than 99.5 percent, and the method is further used forPurification was carried out twice by vacuum sublimation, with a purity of 99.98%.
2.2 Synthesis of other target Compounds
Different intermediates were selected, reference compound A4 was synthesized, other target compounds were synthesized, and finally purified by vacuum sublimation, see in particular table 1.
TABLE 1
The characterization of the compounds is as follows:
compound A4:1H NMR (400 MHz, CDCl) 3 )δ8.79-8.66(m,3H),8.48(dt,J＝8.6,2.0Hz,3H),8.38(d,J＝8.2Hz,1H),8.17(s,1H),8.11(s,2H),8.08-7.97(m,7H),7.97-7.89(m,3H),7.85(ddd,J＝8.3,6.9,1.3Hz,1H),7.64-7.49(m,7H)。
Compound a10:1H NMR (400 MHz, CDCl) 3 )δ8.41-8.17(m,7H),8.04(s,1H),7.97(d,J＝9.4Hz,3H),7.90(d,J＝7.9Hz,3H),7.86-7.76(m,4H),7.56(ddd,J＝8.2,6.9,1.1Hz,1H),7.53-7.45(m,3H),7.43-7.33(m,6H),1.61(s,6H),1.58(s,12H)。
Compound a21:1H NMR (400 MHz, CDCl) 3 )δ8.70(s,1H),8.43(dt,J＝9.4,4.7Hz,2H),8.30-8.19(m,4H),8.09(s,1H),8.06-7.96(m,2H),7.96-7.87(m,4H),7.82(ddd,J＝8.4,6.9,1.3Hz,1H),7.62-7.41(m,9H)。
Compound a26:1H NMR (400 MHz, CDCl) 3 )δ8.72(s,1H),8.48(dd,J＝8.6,1.8Hz,1H),8.37(d,J＝8.2Hz,1H),8.34-8.24(m,4H),8.16(s,1H),8.10-7.96(m,5H),7.96-7.88(m,3H),7.88-7.78(m,3H),7.63-7.52(m,3H),7.52-7.44(m,2H),7.44-7.32(m,4H),1.59(s,12H)。
Compound a31:1H NMR (400 MHz, CDCl) 3 )δ8.86(d,J＝1.6Hz,2H),8.72(s,1H),8.53-8.34(m,4H),8.17(s,1H),8.09(d,J＝7.1Hz,2H),8.07-7.96(m,5H),7.96-7.88(m,1H),7.85(ddd,J＝8.3,6.9,1.3Hz,1H),7.75(d,J＝8.6Hz,2H),7.67-7.46(m,7H),7.40(td,J＝7.6,0.8Hz,2H)。
Compound a37:1H NMR (400 MHz, CDCl) 3 )δ8.36(s,1H),8.30-8.17(m,5H),7.99(s,1H),7.96-7.85(m,4H),7.85-7.75(m,2H),7.60-7.44(m,8H),7.42-7.31(m,2H),1.60(s,6H)。
Compound a42:1H NMR (400 MHz, CDCl) 3 )δ8.74(d,J＝1.0Hz,2H),8.48(dd,J＝8.6,1.7Hz,2H),8.37(dd,J＝4.7,3.4Hz,2H),8.25(dd,J＝8.0,1.6Hz,1H),8.04(ddd,J＝12.2,10.1,7.9Hz,8H),7.97-7.89(m,3H),7.88-7.77(m,2H),7.63-7.44(m,6H),7.44-7.33(m,2H),1.61(s,6H)。
Compound a45:1H NMR (400 MHz, CDCl) 3 )δ8.86(d,J＝1.6Hz,2H),8.43(dd,J＝8.7,1.8Hz,2H),8.36(t,J＝4.0Hz,2H),8.25(dd,J＝8.0,1.4Hz,1H),8.13-8.05(m,3H),8.01(d,J＝9.1Hz,3H),7.89(t,J＝8.7Hz,1H),7.87-7.78(m,2H),7.75(d,J＝8.6Hz,2H),7.67-7.55(m,3H),7.50(qd,J＝8.3,2.9Hz,3H),7.38(ddd,J＝11.4,9.2,6.7Hz,4H),1.61(s,6H)。
3. Characterization of thermodynamic properties
The glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC25 differential scanning calorimeter of the company TA, USA) at a heating rate of 10 ℃/min; the decomposition temperature Td is a temperature at which the weight loss is 5% in a nitrogen atmosphere, measured on a TGA55 thermogravimetric analyzer by the company TA, USA, with a nitrogen flow of 20mL/min, the specific data being given in Table 2 below.
TABLE 2
Compounds of formula (I) Tg(℃) Td(℃)
A4 111 430
A10 169 446
A21 NA 354
A26 152 440
A31 136 460
A37 122 365
A42 137 432
A45 155 462
dPPy-dPPy NA 321
As is clear from the data in the table, the glass transition temperature of the quinoline bipyridine compound represented by the general formula A is above 110 ℃, and the quinoline bipyridine compound is not easy to crystallize and has good film forming property. The thermal decomposition temperature is above 350 ℃, is far higher than the thermal decomposition temperature of dPPy-dPPy, is not easy to decompose and has excellent thermal stability.
4. Preparation of organic electroluminescent element
The above-mentioned organic compound of the present invention is particularly suitable for an electron transport layer in an OLED device, and the effect of the organic compound of the present invention applied as an electron transport layer in an OLED device will be described in detail below by way of specific examples in conjunction with the device structure of fig. 1.
The structural formula of the organic material used therein is as follows:
an organic electroluminescent element using the quinoline bipyridine compound of the present invention as an electron transport layer may comprise a glass and transparent conductive layer (ITO) substrate layer 1, a hole injection layer 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and a cathode layer 6.
Device example 1
Referring to the structure shown in fig. 1, an OLED device is manufactured by using a Sunic sp1710 evaporator, and the specific steps are as follows: ultrasonic washing a glass substrate (corning glass 40 mm. Times.40 mm. Times.0.7 mm) coated with ITO (indium tin oxide) having a thickness of 135nm with isopropyl alcohol and pure water, respectively, for 5 minutes, washing with ultraviolet ozone, and then transferring the glass substrate into a vacuum deposition chamber; the hole transport material HT1 doped with 4% HD was evacuated at a thickness of 20nm (about 10 -7 Torr) is thermally deposited on the transparent ITO electrode to form a hole injection layer; vacuum depositing HT1 with a thickness of 120nm and HT2 with a thickness of 10nm on the hole injection layer as hole transport layers; vacuum depositing BH doped with 4% BD of 25nm on the hole transport layer as a light emitting layer; then, carrying out vacuum deposition on a compound A4 doped with 50% LiQ (8-hydroxyquinoline lithium) to form an electron transport layer, wherein the thickness of the electron transport layer is 30nm; finally, sequentially depositing 2nm thick ytterbium (Yb, electron injection layer) and 150nm magnesium-silver alloy with the doping ratio of 10:1 to form a cathode; finally, the device is transferred from the deposition chamber to a glove box and then encapsulated with a UV curable epoxy and a glass cover plate containing a moisture absorbent.
In the above manufacturing steps, the deposition rates of the organic material, ytterbium metal and Mg metal were maintained at 0.1nm/s, 0.05nm/s and 0.2nm/s, respectively.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound A4:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
Device example 2
An experiment was performed in the same manner as in device example 1, except that: as the electron transport layer, compound a10 was used instead of compound A4 in device example 1.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound A10:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
Device example 3
An experiment was performed in the same manner as in device example 1, except that: as the electron transport layer, compound a21 was used instead of compound A4 in device example 1.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound A21:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
Device example 4
An experiment was performed in the same manner as in device example 1, except that: as the electron transport layer, compound a26 was used instead of compound A4 in device example 1.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound A26:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
Device example 5
An experiment was performed in the same manner as in device example 1, except that: as the electron transport layer, compound a31 was used instead of compound A4 in device example 1.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound A31:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
Device example 6
An experiment was performed in the same manner as in device example 1, except that: as the electron transport layer, compound a37 was used instead of compound A4 in device example 1.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound A37:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
Device example 7
An experiment was performed in the same manner as in device example 1, except that: as the electron transport layer, compound a42 was used instead of compound A4 in device example 1.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound A42:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
Device example 8
An experiment was performed in the same manner as in device example 1, except that: as the electron transport layer, compound a45 was used instead of compound A4 in device example 1.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/Compound A45:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
Device comparative example 1
An experiment was performed in the same manner as in device example 1, except that: as the electron transport layer, the compound ppy-ppy was used instead of the compound A4 in device example 1.
The device structure is expressed as: ITO (135 nm)/HT 1:4% HD (20 nm)/HT 1 (120 nm)/HT 2 (10 nm)/BH 4% BD (25 nm)/dPPy-dPPy:LiQ (5:5, 30 nm) Yb (2 nm)/Mg:Ag (10:1, 150 nm).
The brightness, luminous efficiency, EQE (external quantum efficiency) of the device were measured by the french FS-100GA4 test, the device lifetime LT96 (the time taken for the initial brightness to decay to 3840nits, referenced to the device comparative example, normalized) was measured in the french FS-MP96 test, and all measurements were performed in ambient atmosphere. Further, the device was at 10mA/cm 2 Specific performance data for operating voltage (V), current efficiency (c.e.), power efficiency (p.e.), external Quantum Efficiency (EQE), and color coordinates (CIEx, CIEy) at current density are shown in table 3.
TABLE 3 Table 3
Compared with the device comparative example 1, the device using the quinoline bipyridine compound of the invention as an electron transport material has improved efficiency and service life.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (3)

1. A quinoline bipyridine compound, characterized in that the quinoline bipyridine compound has a structure represented by the following general formula a:
wherein Ar is 1 And Ar is a group 2 Identical, and Ar is as described 1 And the Ar is as described 2 Selected from naphthyl, anthryl, phenanthryl, dimethylfluorenyl, dibenzofuranyl or dibenzothiophenyl; or (b)
Ar 1 And Ar is a group 2 Different, the Ar 1 And the Ar is as described 2 Selected from naphthyl, anthryl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl or spirobifluorenyl.
2. The quinoline bipyridine compound according to claim 1, wherein the quinoline bipyridine compound is selected from any one of the following:
3. use of the quinoline bipyridine compound according to claim 1 or 2 as an electron transport material in an organic electroluminescent element.
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KR20150121394A (en) * 2014-04-18 2015-10-29 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN107417668A (en) * 2017-05-11 2017-12-01 江苏三月光电科技有限公司 A kind of organic compound based on pyridine and benzimidazole and its application on OLED
CN107602538A (en) * 2017-09-29 2018-01-19 江苏三月光电科技有限公司 A kind of organic compound based on pyridine and quinoline beautiful jade and its application on OLED
CN108727358A (en) * 2018-08-06 2018-11-02 长春海谱润斯科技有限公司 A kind of heterocyclic compound and its organic electroluminescence device
CN111362866A (en) * 2018-12-26 2020-07-03 江苏三月光电科技有限公司 Azabenzene modified organic compound and application thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150121394A (en) * 2014-04-18 2015-10-29 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN107417668A (en) * 2017-05-11 2017-12-01 江苏三月光电科技有限公司 A kind of organic compound based on pyridine and benzimidazole and its application on OLED
CN107602538A (en) * 2017-09-29 2018-01-19 江苏三月光电科技有限公司 A kind of organic compound based on pyridine and quinoline beautiful jade and its application on OLED
CN108727358A (en) * 2018-08-06 2018-11-02 长春海谱润斯科技有限公司 A kind of heterocyclic compound and its organic electroluminescence device
CN111362866A (en) * 2018-12-26 2020-07-03 江苏三月光电科技有限公司 Azabenzene modified organic compound and application thereof

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