CN111205278B - Spirofluorene triphenylamine derivative and application thereof in organic electroluminescent device - Google Patents
Spirofluorene triphenylamine derivative and application thereof in organic electroluminescent device Download PDFInfo
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Abstract
The invention relates to a spirofluorene triphenylamine derivative shown in a formula (1). The invention also discloses application of the compound shown in the formula (1) in preparation of an organic electroluminescent device or an organic fluorescent material. The compound shown in the formula (1) has the advantages of simple synthetic route, high synthetic yield, wide band gap, high triplet state energy level, high carrier mobility and high thermal stability. The compounds can be suitable for use in the light emitting layer, or host, of an OLED device, as well as in any of the transport layers of the device. The organic fluorescent material has high fluorescence quantum yield and shows deep blue and high-efficiency performance in an organic electroluminescent device.
Description
Technical Field
The invention relates to the field of organic electroluminescent materials and devices, in particular to a spirofluorene triphenylamine derivative and application thereof in an organic electroluminescent device.
Background
Organic electroluminescent devices (OLEDs) are used for their unique properties, such as: the advantages of fast response time, high efficiency, flexibility and the like are receiving more and more attention. Recently, the existence of heavy metals in phosphorescent materials can break the orbital spin law to achieve 100% internal quantum efficiency, that is, 25% of singlet excitons and 75% of triplet excitons under the electro-excitation can be effectively utilized, while 75% of triplet excitons in the traditional fluorescent materials cannot be utilized, so that the efficiency is low. The phosphorescent material can realize high-efficiency devices and shows excellent performance in blue, green and red devices. CN 102911145A discloses a dibenzo-heterocyclic spiro-bifluorene compound, a preparation method thereof and an organic electrophosphorescent device. CN 104892578A discloses a fluorene spiro triphenylamine derivative and application thereof, and the compound can be used as a blue phosphorescent main body material. CN 108250214A discloses an oxaspirofluorene triphenylamine derivative, a preparation method and application thereof, and the material is also suitable for preparing organic phosphorescent light-emitting devices. However, it is considered that the presence of heavy metals in phosphorescent materials will increase the cost of the device and also cause environmental pollution.
The thermally activated delayed fluorescence material (TADF) can realize smaller singlet state and triplet state energy difference (E)ST) Thereby, a reverse intersystem crossing process can be obtained, and finally, 100% of internal quantum efficiency can be realized by using all excitons. Compared with a blue light device, the green light and the red light realize high efficiency and high stability, and the low efficiency, impure spectrum and low voltage of the blue light are always obstacles for popularizing and applying the OLED. How to design and fabricate a high-performance blue device is a matter of consideration. CN 104860884A discloses a triphenylethylene derivative and application thereof, wherein the triphenylethylene derivative has high fluorescence quantum efficiency and can be used as a luminescent material to be applied to undoped fluorescent devices.
There is a need to develop new high-performance blue light emitting materials and apply them in devices, which will have the development of illumination and display.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a spirofluorene 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 carrier mobility, high thermal stability, high fluorescence quantum yield and deep blue and high-efficiency performance in the organic electroluminescent device.
A first object of the present invention is to provide a compound represented by the formula (1):
the compound shown in the formula (1) comprises spirofluorene triphenylamine groups and dibenzothiophene sulfone units, and consists of electron donating groups and rigid electron withdrawing groups, and is accompanied with space charge transfer effect. The preparation method has the advantages of high triplet state energy level and wide band gap, high molecular mobility, simple synthesis, high synthesis yield, good thermal stability and high quantum yield.
Further, the preparation method of the compound represented by the formula (1) comprises the following steps:
(1) under the protection atmosphere, 2-bromodibenzothiophene and 1-fluorenone boric acid react in an organic solvent under the action of a catalyst at the reaction temperature of 50 ℃ to obtain a compound 2 after the reaction is completed;
(2) carrying out an oxidation reaction on the compound 2 and 30 wt% of hydrogen peroxide at 80 ℃, oxidizing sulfur atoms into sulfone groups, and obtaining a compound 3 after the reaction is completed;
(3) at-78 ℃, 2-bromotriphenylamine and n-butyl lithium reagent are subjected to nucleophilic substitution reaction, after 1 hour of reaction, the compound 3 is added into the reaction system, and the final product is obtained after the reaction is completed.
The reaction route is as follows:
further, in the step (1), the organic solvent is one of toluene, N-dimethylformamide and tetrahydrofuran.
Further, in the step (1), the protective atmosphere is inert gas, and the inert gas is nitrogen or argon.
Further, in the step (1), the catalyst is palladium acetate, tetrakis (triphenylphosphine) palladium (Pd (PPh)3)4) Bis (dibenzylideneacetone) palladium, (Pd (dba)2) One kind of (1).
Further, in the step (1), 5-bromoacenaphthylene-1, 2-dione: (4- (diphenylamine) phenyl) boronic acid: the molar ratio of the catalyst is 2-2.5:2.4:0.092, preferably one of 2:2.4:0.092, 2.2:2.4:0.092, 2.3:2.4:0.092, 2.4:2.4:0.092 and 2.5:2.4: 0.092.
The second purpose of the invention is to disclose the application of the compound shown in the formula (1) in preparing an organic electroluminescent device or an organic fluorescent material.
Further, the compound represented by the formula (1) is used for preparing a light-emitting layer of an organic electroluminescent device.
The third purpose of the invention is to disclose an organic electroluminescent device, which comprises an organic luminescent layer, wherein the organic luminescent layer comprises a host material and a guest material, the guest material is selected from the compounds shown in the formula (1), and the molar ratio of the guest material to the host material is 0.1-0.5: 1. The organic electroluminescent device is a deep blue light device, and is low in driving voltage and high in efficiency.
Further, the main material is bis [2- ((oxo) diphenylphosphino) phenyl ] ether (DPEPO).
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 thickness of the anode layer is 100-150 nm; 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 15-30 nm; the thickness of the hole blocking layer is 5-20 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, magnesium and silver.
Preferably, 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 or polypyrrole.
Furthermore, the material of the hole injection layer is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN) or molybdenum trioxide; the hole transport layer is made of 4,4 '-cyclohexyl bis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), N' -diphenyl-N, N '- (1-naphthyl) -1,1' -biphenyl-4, 4 '-diamine (NPB) or 4,4' -tris (carbazol-9-yl) triphenylamine (TCTA); the material of the electron blocking layer is 9,9' - (1, 3-phenyl) di-9H-carbazole (mCP).
Further, the hole blocking layer is made of bis [2- ((oxo) diphenylphosphino) phenyl ] ether (DPEPO); the material of the electron transport layer is 3,3'- [5' - [3- (3-pyridyl) phenyl ] [1,1':3',1 '-terphenyl ] -3,3' -diyl ] bipyridine (TmPyPb) or 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi); the material of the electron injection layer is 8-hydroxyquinoline-lithium (Liq) or lithium fluoride.
By the scheme, the invention at least has the following advantages:
the invention provides a spirofluorene triphenylamine derivative shown in a formula (1), which has the characteristics of wide band gap, high triplet state energy level, high carrier mobility and high thermal stability. The organic molecular material has great prospect in a light-emitting device, is suitable for a light-emitting layer or a main body in an OLED device, and can also be used in any layer of a device transmission layer.
The spirofluorene triphenylamine derivative shown in the formula (1) can be used as an organic fluorescent material to prepare a blue light device, and has the properties of high efficiency and low loss.
The invention provides a blue light organic electroluminescent device which is low in driving voltage and high in efficiency.
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 shows the oxidation potential test results of formula (1) prepared in example 1.
Fig. 2 is a schematic cross-sectional view of an organic electroluminescent device according to 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 is a plot of current efficiency versus current density for an electroluminescent device prepared in example 2.
Fig. 6 is an electro-luminescence spectrum of the electroluminescent device prepared in comparative example 1.
Fig. 7 is a current efficiency versus current density curve for the electroluminescent device prepared in comparative example 1.
Fig. 8 is a graph of current versus voltage 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. The following starting materials are commercially available from the open literature unless otherwise specified.
In the following examples of the invention, the compounds used and their corresponding structural formulae are as follows:
example 1
A compound represented by the formula (1), which has the following structural formula:
the reaction route and the specific preparation method of the compound represented by the formula (1) are as follows:
(1) 2-Bromobenzothiophene, 1-fluorenone boronic acid (0.69g,2.4mmol) were mixed in 60mL Tetrahydrofuran (THF) solvent under argon. To the above solution was added catalyst Pd (PPh)3)4And obtaining a mixed solution. Heating the mixed solution at 50 ℃ for 10 minutes, and adding 2M K2CO3Aqueous solution 15And (mL). The reaction time was 12 hours and the reaction temperature was 50 ℃. After waiting for the temperature of the mixed liquid to drop to room temperature, THF was removed under vacuum, and 100mL of methylene chloride was added to the residual solid, followed by washing with 100mL of water, which was repeated 3 times, and finally water was removed under vacuum. The resulting residue was purified by column on silica gel eluting with petroleum ether/dichloromethane (1/1, v/v) to give Compound 2.
(2) And (3) carrying out oxidation reaction on the compound 2 and 30 wt% of hydrogen peroxide at the temperature of 80 ℃, oxidizing sulfur atoms into sulfuryl, and obtaining a compound 3 after complete reaction.
(3) At-78 ℃, 2-bromotriphenylamine and n-butyllithium reagent are subjected to nucleophilic substitution reaction, after the reaction is carried out for 1 hour, the compound 3 is added into the reaction system, and the final product (SPIRO-SO) is obtained after the reaction is completed2-TPA)。
SPIRO-SO2The results of the structure and performance test of TPA are as follows:
(1)1H NMR(400MHz,CDCl3)δ7.95(dd,J＝7.6,0.8Hz,1H),7.88(d,J＝7.6Hz,1H),7.82(dd,J＝5.8,3.0Hz,1H),7.56–7.43(m,6H),7.42–7.32(m,2H),7.25–7.21(m,2H),7.16(dd,J＝5.7,3.0Hz,1H),7.02(dd,J＝7.5,0.8Hz,1H),6.88(d,J＝7.5Hz,2H),6.80–6.69(m,3H),6.60(dd,J＝7.8,1.2Hz,1H),6.54(t,J＝7.2Hz,2H),6.37(dd,J＝7.7,1.3Hz,2H),5.84(d,J＝8.3Hz,2H).
(2)13C NMR(101MHz,CDCl3)δ159.89,155.32,146.59,140.74–139.97,138.88,138.05,137.46,135.53,133.38,131.42,131.18–130.35,130.20,129.30,128.85,128.14,127.34,126.16,122.75,122.09,121.75,120.75,119.95,114.77,56.09.MALDI-MS(m/z)of C43H27NSO2 for[M+]calcd.621.18; found,621.45, the compound has the correct structure.
(3) Mass Spectrometry MS (MALDI-TOF) M/z 621.45[ M + ].
(4) The decomposition temperature Td is 388 ℃;
(5) ultraviolet absorption wavelength: 311nm,292nm and 282 nm;
(6) fluorescence emission wavelength: 468 nm;
(7) HOMO value: -5.32eV, cyclic voltammetry, as shown in figure 1.
Example 2
An electroluminescent device was prepared using the compound SPIRO-SO2-TPA synthesized in example 1, and its structure is shown in fig. 2, which consists 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 sequentially disposed from bottom to top. The preparation steps of the electroluminescent device are as follows:
the first step is as follows: and repeatedly carrying out ultrasonic treatment on the patterned ITO conductive glass substrate 1 in an ultrasonic machine for three times by using acetone and ethanol, 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.
The second step is that: 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 multiplied by 10-4Pa or so.
The third step: a hole injection material HAT-CN with the thickness of 10nm, a hole transport material TAPC with the thickness of 300nm, an electron blocking material mCP with the thickness of 8nm are sequentially evaporated on the surface of the anode layer 2. The evaporation rates are all
The fourth step: then, an organic light-emitting layer 6 is evaporated and plated on the electron blocking layer 5, the organic light-emitting layer 6 is co-doped by a host material DPEPO and a compound SPIRO-SO2-TPA synthesized in the embodiment 1 of the invention, the compound SPIRO-SO2-TPA synthesized in the embodiment 1 is used as a light-emitting material, the molar mass ratio of the light-emitting material to the host material is 0.25:1, and the thickness of the light-emitting layer is 20 nm; the evaporation rate is
The fifth step: a layer of a host material DPEPO is vacuum-evaporated on the organic light-emitting layer 6 as a hole blocking layer 7 at an evaporation rate of
The thickness of the coating film is 8 nm.
And a sixth step: vacuum evaporating electron transport layer 8 on the hole blocking layer 7 with material TmPyPb and thickness of 40nm, evaporatingA plating rate of
The seventh step: vacuum evaporating an electron injection layer 9 on the electron transport layer 8, wherein the material is Liq, the thickness is 2nm, and the evaporation rate is
Eighth 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 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 468nm, the spectrum of the material is very blue, and the organic luminescent device can be effectively applied to display and illumination. The material has high mobility, high quantum yield, high triplet state energy level, high efficiency and low voltage performance of 0.2mA/cm2The current density driving voltage is 4.0V (figure 4), and the current efficiency can reach 21.54cd/A (figure 5).
Comparative example 1
An electroluminescent device was produced in accordance with the method of example 2, differing from example 2 in that in the fourth step, the compound SPIRO-SO2-TPA synthesized in example 1 was replaced in the luminescent layer with a conventional fluorescent material of a non-TADF nature (Spiro-2P-SO)2TPA), the other conditions being unchanged. Spiro-2P-SO2TPA molecular structure 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 current density driving voltage was 4.5V and the current efficiency was only 12.0cd/A (FIG. 8).
The above results show that the device prepared in example 2 requires smaller driving voltage and higher efficiency than the device of comparative example 1 under the same current density, and the compound represented by formula (1) of the present invention is more suitable for blue light devices and has a bluer spectrum.
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 (9)
1. A compound represented by the formula (1):
2. the use of a compound according to claim 1 for the preparation of an organic electroluminescent device or an organic fluorescent material;
the compound shown in the formula (1) is used for preparing a guest material in a light-emitting layer of the organic electroluminescent device.
3. An organic electroluminescent device comprising an organic light-emitting layer, wherein the organic light-emitting layer comprises a host material and a guest material selected from the compounds represented by the formula (1) in claim 1, and the molar ratio of the guest material to the host material is 0.1 to 0.5: 1.
4. The organic electroluminescent device according to claim 3, wherein the host material is bis [2- ((oxo) diphenylphosphino) phenyl ] ether.
5. The organic electroluminescent device according to claim 3, 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 sequentially disposed.
6. The organic electroluminescent device as claimed in claim 5, wherein the anode layer has a thickness of 100-150 nm; 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 15-30 nm; the thickness of the hole blocking layer is 5-20 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.
7. The organic electroluminescent device according to claim 5, 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, magnesium and silver.
8. The device according to claim 5, 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',4'' -tri (carbazole-9-yl) triphenylamine; the electron blocking layer is made of 9,9' - (1, 3-phenyl) di-9H-carbazole.
9. The device according to claim 5, wherein the hole blocking layer is bis [2- ((oxo) diphenylphosphino) phenyl ] ether; the material of the electron transport layer is 3,3'- [5' - [3- (3-pyridyl) phenyl ] [1,1':3',1'' -terphenyl ] -3,3'' -diyl ] bipyridine or 1,3, 5-tri (1-phenyl-1H-benzimidazol-2-yl) benzene; the material of the electron injection layer is 8-hydroxyquinoline-lithium or lithium fluoride.
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| Bending-Type Electron Donor−Donor−Acceptor Triad: Dual ExcitedState Charge-Transfer Coupled Structural Relaxation;Jia-An Lin等;《Chem.Mater.》;20190722;第31卷;2981-5992 * |
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| CN111205278A (en) | 2020-05-29 |
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