CN111362940A - Triphenylamine derivative and application thereof in organic electroluminescent device - Google Patents
Triphenylamine derivative and application thereof in organic electroluminescent device Download PDFInfo
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Abstract
The invention relates to a triphenylamine derivative shown in a formula (1) and application thereof in an organic electroluminescent device or an organic luminescent material, wherein the compound shown in the formula (1) has the advantages of wide band gap, high triplet state energy level, high thermal stability and good hole transmission performance, and can successfully prepare a high-efficiency green light organic luminescent exciplex system.
Description
Technical Field
The invention relates to the field of organic electroluminescent materials and devices, in particular to a triphenylamine derivative and application thereof in an organic electroluminescent device.
Background
Organic electroluminescent devices (OLEDs) exhibit unique properties in optoelectronic devices because of high contrast, high efficiency, and flexibility. The development of conventional fluorescent material-based OLEDs is limited (25%) by Internal Quantum Efficiency (IQE) and cannot utilize the remaining 75% of the radiative triplet excitons. Second generation OLEDs can be fabricated by collecting sheets using phosphorescent emittersRecently, Thermally Activated Delayed Fluorescence (TADF) materials, known as Intramolecular Charge Transfer (ICT) excited states, have been referred to as efficient reverse system crossing (RISC) processes and small singlet-triplet energy splitting (△ E) to provide eqe with 100% Internal Quantum Efficiency (IQE)ST). Therefore, they have the ability to excite triplet excitons from the triplet excited state (T)1) The ability to convert to singlet state, thereby effectively utilizing excited states (S) of singlet and triplet excitons1). Accordingly, phosphorescent and TADF materials are widely considered as promising strategies to exploit excitons to achieve high performance devices.
CN102414176A discloses a class of monoamine compounds, which can be used for preparing organic electroluminescent elements, display devices and lighting elements, wherein the driving voltage of the organic electroluminescent elements is 7.12-8.63V, and the driving voltage is relatively high.
The exciplex is generally formed by combining an electron donor and an electron acceptor to form a system with TADF performance, and can form a high-efficiency fluorescent light-emitting system. And the organic electroluminescent material has charge transfer balance, low energy injection potential barrier and wide light-emitting recombination region, so that the exciplex plays an important role in the OLED. However, much work has focused on the electron acceptor materials, and relatively little research has been done on electron donor materials. In order to realize a high-efficiency light emitting device, it is necessary to design a new electron donor material and form an exciplex system, which is advantageous for the development and application of an electron light emitting device.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a triphenylamine derivative and an application thereof in an organic electroluminescent device, wherein the compound shown in the formula (1) has the advantages of wide band gap, high triplet state energy level, high thermal stability and good hole transport performance, and can successfully prepare a high-efficiency green light organic light-emitting exciplex system.
In a first aspect, the present invention discloses a compound represented by formula (1):
the preparation route of the compound represented by the formula (1) is as follows:
the preparation method of the compound shown in the formula (1) comprises the following steps:
under the protection atmosphere, bromobenzene reacts with a compound shown as a formula M1 under the action of n-butyllithium, the reaction is carried out in an organic solvent at the temperature of minus 10 ℃ to obtain an intermediate product after the reaction is completed, then the intermediate product is subjected to reflux reaction in acetic acid and hydrochloric acid at the reaction temperature of 80-110 ℃ to obtain the compound shown as the formula (1) after the reaction is completed.
In a second aspect, the invention discloses an application of the compound shown in the formula (1) in preparing an organic electroluminescent device (OLED) or an organic luminescent material.
Further, the compound represented by the formula (1) is used for preparing a light-emitting layer and/or an electron blocking layer of an organic electroluminescent device.
Further, the organic electroluminescent device comprises an organic light-emitting layer, the organic light-emitting layer comprises an organic electron donor material and an organic electron acceptor material, the organic electron donor material is selected from compounds shown in a formula (1), and the molar ratio of the organic electron donor material to the organic electron acceptor material is 0.22-0.75: 0.5.
Further, the organic electron acceptor material is 1,3, 5-triazine-2-2, 4, 6-triyl) tris (benzene-3, 1-diyl) tris (diphenylphosphine oxide) (PO-T2T).
Further, the organic electroluminescent device comprises a substrate, an anode layer, a hole injection layer, a hole transport layer, an electron blocking layer, an organic light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode layer which are arranged in sequence.
Further, the material of the substrate is glass or a flexible non-conductive material.
Further, the thickness of the hole injection layer is 2-12 nm; the thickness of the hole transport layer is 20-120 nm; the thickness of the electron blocking layer is 5-20 nm; the thickness of the organic light-emitting layer is 10-30 nm; the thickness of the hole blocking layer is 10-20 nm; the thickness of the electron transmission layer is 30-80 nm; the thickness of the electron injection layer is 1-3 nm; the thickness of the cathode layer is 70-150 nm.
Furthermore, the anode layer is made of an inorganic material or an organic conductive polymer material; the cathode layer is made of one or more of silver, gold, aluminum and magnesium.
Further, the inorganic material is one of indium tin oxide, zinc tin oxide, or a metal. The organic conductive polymer is 3, 4-ethylene dioxythiophene monomer, polyaniline, polypyrrole, polythiophene or one of sodium polyvinyl benzene sulfonate.
Further, the material of the hole injection layer is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazatriphenylene (HATCN) or molybdenum trioxide. The hole transport layer is made of 4,4 '-cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), N' -diphenyl-N, N '- (1-naphthyl) -1,1' -biphenyl-4, 4 '-diamine (NPB), or 4,4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA).
Further, the material of the electron blocking layer comprises a compound shown in a formula (1); the hole-blocking layer is made of 1,3, 5-triazine-2-2, 4, 6-triyl) tris (benzene-3, 1-diyl) tris (diphenylphosphine oxide) (PO-T2T).
Further, the material of the electron transport layer includes 1,3, 5-triazine-2-2, 4, 6-triyl) tris (benzene-3, 1-diyl) tris (diphenylphosphine oxide) (PO-T2T) or 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi).
Furthermore, the material of the electron injection layer is 8-hydroxyquinoline-lithium (Liq) or lithium fluoride.
Further, the organic light emitting material is an exciplex system, and the organic light emitting material includes the compound represented by the formula (1) and other electron type transport materials.
The chemical structure of the partial compound related by the invention is as follows:
by the scheme, the invention at least has the following advantages:
the compound shown in the formula (1) is a triphenylamine derivative, and the material has the advantages of good rigid structure and thermal stability, simple and convenient molecular synthesis route, low synthesis cost, high triplet state energy level, high mobility and proper leading edge orbital energy level. The organic electron donor can be used as an organic electron donor for an organic electroluminescent device (OLED), can effectively form a high-efficiency exciplex light-emitting system with other electron type transmission materials, and can also be used as any layer of a transmission layer, and the formed green light device has the properties of high efficiency and low voltage loss. The compound represented by the formula (1) of the present invention can also be used as an organic light-emitting material.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical solutions of the present invention more clearly understood and to implement them in accordance with the contents of the description, the following description is made with reference to the preferred embodiments of the present invention and the accompanying detailed drawings.
Drawings
FIG. 1 is an ultraviolet light spectrometer test of DEX prepared in example 1.
Fig. 2 is a schematic view of the structure of the organic electroluminescent device of the present invention.
Fig. 3 is an electro-luminescence spectrum of an electroluminescent device prepared in example 2.
Fig. 4 is a graph of current versus voltage for an electroluminescent device prepared in example 2.
Fig. 5 external quantum efficiency vs. luminance curves for electroluminescent devices prepared in example 2.
Fig. 6 is an electro-luminescence spectrum of the electroluminescent device prepared in comparative example 1.
Fig. 7 is a graph of current versus voltage for the electroluminescent device prepared in comparative example 1.
Fig. 8 is a graph of external quantum efficiency versus luminance for the electroluminescent device prepared in comparative example 1.
Description of reference numerals:
1-a glass substrate; 2-an anode layer; 3-a hole injection layer; 4-a hole transport layer; 5-an electron blocking layer; 6-an organic light-emitting layer; 7-a hole blocking layer; 8-an electron transport layer; 9-electron injection layer; 10-cathode layer.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1
This example provides an organic material, whose structural formula is shown in formula (1), and the compound is abbreviated as DEX:
the route and method for the preparation of DEX is as follows:
4.7g (30.0mmol) of bromobenzene was dissolved in 30mL of anhydrous ether in a 100mL two-neck flask under nitrogen protection, stirred and cooled to-78 ℃. 2.3mL (5.5mmol) of 2.4M n-butyllithium were added dropwise to the solution via a constant pressure dropping funnel, and stirring was continued at-78 ℃ for 1 hour. Then, 2.05g (4.9mmol) of compound M1 was dispersed in 30mL of anhydrous tetrahydrofuran under nitrogen and added dropwise to the reaction solution. After the addition, the temperature was gradually raised to-10 ℃ and the reaction was carried out for 12 hours. After the reaction was complete, 5mL of water was added to quench the reaction and the tetrahydrofuran and ether were removed by rotary drying. The crude product obtained is dissolved in 150mL of dichloromethane and washed 3 times with 60mL of water. Drying the organic phase by using anhydrous sodium sulfate, and then removing the solvent by rotary drying to obtain a secondary crude product. The secondary crude product was purified with dichloromethane: petroleum ether is 3: 1 (volume ratio) of eluent was separated and purified on a silica gel column to obtain 3.0g of an intermediate product. The resulting intermediate was dissolved in 25mL of acetic acid in a 50mL two-necked flask and 2.5mL of hydrochloric acid was added, and the mixture was heated to reflux (temperature 80-110 ℃ C.) with stirring and reacted for 6 hours. After the reaction is completed, cooling the reaction system to room temperature, pouring the reaction system into 300mL of ice water, carrying out vacuum filtration, and washing filter residues for three times. And (3) using dichloromethane for filter residue: petroleum ether is 1: 4 (volume ratio) of eluent was separated and purified on a silica gel column to obtain 2.9g of DEX as a final product with a yield of 80%.
The structural and performance test results of DEX are as follows:
(1)MS(EI):m/z 737.30[M+]. Calculated value of elemental analysis C57H39N (%): c92.77, H5.33, N1.90; measured value: c92.55, H5.29, N1.85.
(2) Decomposition temperature Td:397℃；
(3) Ultraviolet absorption wavelength: 344 nm;
(4) fluorescence emission wavelength: 370 nm;
(5) HOMO value: 5.8eV, UV photoelectron spectrometer, as shown in FIG. 1.
Example 2
This example provides an organic electroluminescent device and a method for preparing the same, prepared from the compound DEX represented by formula (1) prepared in example 1, wherein in the organic electroluminescent device, the compound represented by formula (1) of the present invention constitutes a light-emitting layer and an electron blocking layer in the organic electroluminescent device. The organic electroluminescent device is composed of a glass substrate 1, an anode layer 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, an organic light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9 and a cathode layer 10 which are arranged from bottom to top in sequence (figure 2). The preparation steps of the organic electroluminescent device are as follows: the first step is as follows: repeatedly carrying out ultrasonic treatment on the patterned ITO conductive glass substrate 1 in an ultrasonic machine for three times by using acetone, ethanol and deionized water, and then baking the patterned ITO conductive glass substrate in a baking oven at 100 ℃ until the patterned ITO conductive glass substrate is dried for later use. ITO is used as the anode layer 2.
Secondly, placing the ITO conductive glass substrate 1 in a vacuum chamber by using an ultraviolet machine for ozone for 15 minutes, and vacuumizing to 4.0 × 10-4Pa or so.
The third step: sequentially evaporating a hole injection material HAT-CN, a hole transport material TAPC with the thickness of 10nm, an electron blocking material DEX with the thickness of 30nm and the thickness of 10nm on the surface of the anode layer 2; the evaporation rate is
The fourth step: then, an organic light-emitting layer 6 was deposited on the electron blocking layer 5 by vapor deposition, and the organic light-emitting layer 6 was composed of DEX synthesized in inventive example 1 (asOrganic electron donor material) and an electron acceptor material PO-T2T material. The molar mass ratio of the organic electron donor material to the organic electron acceptor material is 1:1, and the thickness of the organic light-emitting layer 6 is 20 nm; the evaporation rate is
The fifth step: vacuum evaporating a layer of organic electron acceptor material PO-T2T as a hole blocking layer and an electron transport layer on the organic light-emitting layer 6 at a rate of
The total thickness of the PO-T2T coating film is 45 nm.
And a sixth step: vacuum evaporating an electron injection layer 9 on the electron transport layer, wherein the material is Liq, the thickness is 2nm, and the evaporation rate is
The seventh step: vacuum evaporating cathode layer 10 on the electron injection layer 9, the material is Al, the thickness is 120nm, and the speed is
The chemical structure of the material used in example 2 is as follows:
the electroluminescent device prepared in example 2 has an electro-luminescence spectrum as shown in fig. 3. The result shows that the luminous peak of the organic luminescent device prepared by the invention is 520nm, the luminescence of the exciplex is green light, the exciplex has important function in display and illumination, the mobility of the material is high, and the mobility is 0.2mA/cm2The voltage at current density drive is 2.6V (fig. 4), providing a reliable strategy for making OLEDs with low power consumption, and the highest external quantum efficiency of 11.2% can be achieved (fig. 5).
Comparative example 1
An organic electroluminescent device was prepared as in example 2, with that of example 2The difference is that in the fourth step, a commercial electron donor material TCTA and an electron acceptor material PO-T2T are co-doped in the luminescent layer to form an exciplex, the doping molar mass ratio is 1:1, and the thickness of the organic luminescent layer is 20 nm; the evaporation rate is
The molecular structure of TCTA is as follows:
an electroluminescence spectrum of the electroluminescence device prepared in comparative example 1 is shown in fig. 6; the current versus voltage curve for the device is shown in fig. 7. At 0.2mA/cm2The voltage at current density drive was 2.7V and the highest external quantum efficiency was only 4.0% (fig. 8).
Therefore, under the same current density, the device prepared in example 2 requires smaller driving voltage and higher efficiency than the device of comparative example 1, and is more suitable for being applied to a high-efficiency OLED device.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, it should be noted that, for those skilled in the art, many modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A compound represented by the formula (1):
2. use of the compound of claim 1 for the preparation of an organic electroluminescent device or an organic light-emitting material.
3. Use according to claim 2, wherein the compound of formula (1) is used for the preparation of a light-emitting layer and/or an electron blocking layer of the organic electroluminescent device.
4. Use according to claim 2, wherein the organic electroluminescent device comprises an organic light-emitting layer comprising an organic electron donor material and an organic electron acceptor material, wherein the organic electron donor material is selected from compounds of formula (1), and wherein the molar ratio of the organic electron donor material to the organic electron acceptor material is 0.22-0.75: 0.5.
5. Use according to claim 4, wherein the organic electron acceptor material is 1,3, 5-triazine-2-2, 4, 6-triyl) tris (benzene-3, 1-diyl)) tris (diphenylphosphine oxide).
6. The use according to claim 4, wherein the organic electroluminescent device comprises a substrate, an anode layer, a hole injection layer, a hole transport layer, an electron blocking layer, an organic light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode layer, which are arranged in this order.
7. Use according to claim 6, wherein the hole injection layer has a thickness of 2-12 nm; the thickness of the hole transport layer is 20-120 nm; the thickness of the electron blocking layer is 5-20 nm; the thickness of the organic light-emitting layer is 10-30 nm; the thickness of the hole blocking layer is 10-20 nm; the thickness of the electron transmission layer is 30-80 nm; the thickness of the electron injection layer is 1-3 nm; the thickness of the cathode layer is 70-150 nm.
8. The use according to claim 6, wherein the anode layer is made of an inorganic material or an organic conductive polymer material; the cathode layer is made of one or more of silver, gold, aluminum and magnesium.
9. The use according to claim 6, wherein the hole injection layer is made of 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene or molybdenum trioxide; the material of the hole transport layer is 4,4 '-cyclohexyl di [ N, N-di (4-methylphenyl) aniline ], N' -diphenyl-N, N '- (1-naphthyl) -1,1' -biphenyl-4, 4 '-diamine or 4,4' -tri (carbazole-9-yl) triphenylamine.
10. The use according to claim 6, wherein the material of the electron blocking layer comprises a compound represented by formula (1); the materials of the hole blocking layer and the electron transport layer respectively comprise 1,3, 5-triazine-2-2, 4, 6-triyl) tri (benzene-3, 1-diyl) tri (diphenyl phosphine oxide).
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