Organic compound and application thereof

Abstract

The invention provides an organic compound and application thereof, and belongs to the technical field of organic electroluminescent materials, the organic compound has a structure as shown in a formula A. The organic compound provided by the invention can enable an organic electroluminescent device to have lower driving voltage, higher luminous efficiency and longer service life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials and relates to an organic compound and application thereof. Background Art

[0002] Pope et al. first discovered the electroluminescent properties of single crystal anthracene in 1965, which was the first electroluminescent phenomenon of organic electroluminescent compounds; in 1987, Tang et al. of Kodak Company in the United States successfully developed low-voltage, high-brightness organic light-emitting diodes (OLED) using organic small molecule semiconductor materials. Organic light-emitting diodes (OLED), as a new display technology, have many advantages such as self-luminescence, wide viewing angle, low energy consumption, rich colors, fast response speed, wide applicable temperature range and flexible display.

[0003] In order to improve the luminous efficiency of organic light-emitting diodes, various fluorescent and phosphorescent luminescent material systems have been developed. Organic light-emitting diodes using fluorescent materials have the characteristics of high reliability, but their internal electroluminescent quantum efficiency under electrical excitation is limited to 25%, because the ratio of the singlet excited state and triplet excited state of the excitons generated by the current is 1:3. In contrast, organic light-emitting diodes using phosphorescent materials have achieved an internal electroluminescent quantum efficiency of almost 100%, so the development of phosphorescent luminescent materials has been widely studied.

[0004] The luminescent material (guest) can be used together with the matrix material (host) as a luminescent material to improve color purity, luminous efficiency and stability. Since the host material has a great influence on the efficiency and characteristics of the electroluminescent device when the host material / guest system is used as the luminescent layer of the light-emitting device, the selection of the host material is very important. At present, the stacking performance of the existing organic electroluminescent materials is poor, resulting in the problems of low stability and unbalanced carrier mobility of the organic electroluminescent material, resulting in the problems of high driving voltage, low luminous efficiency and short life of the organic electroluminescent device containing the organic electroluminescent material, which seriously limits the application of organic electroluminescent devices. Summary of the invention

[0005] In view of the deficiencies in the prior art, the present invention aims to provide an organic compound and application thereof.

[0006] In order to achieve the purpose of the invention, the present invention adopts the following technical solutions:

[0007] In one aspect, the present invention provides an organic compound having a structure shown in Formula A:

[0008]

[0009] X is selected from O or NAr,

[0010] Ar is selected from phenyl, biphenyl or naphthyl,

[0011] L 1 -L 11 are each independently selected from a single bond or a naphthylene group,

[0012] R 1 -R 11 Each independently selected from hydrogen, deuterium or The wavy line represents the attachment site of the group, and R' is selected from phenyl, biphenyl or naphthyl.

[0013] Preferably, L 1 -L 11 Each is independently selected from naphthylene, wherein the naphthylene is selected from any of the following groups,

[0014]

[0015] The numbers and wavy lines represent the attachment sites of the groups.

[0016] Preferably, Selected from any of the following groups:

[0017]

[0018]

[0019] The wavy line represents the attachment site of the group.

[0020] Preferably, the organic compound has any of the following structures:

[0021]

[0022] Preferably, the organic compound is selected from any one of compounds 1-864, and the structure of compound 1-864 is substituted by LR

[0023] Formula 1, wherein L is selected from L 1 -L 4 , R is selected from R 1 -R 4 , Formula 1 is one of Formula 1-1, Formula 1-2, Formula 1-3, and Formula 1-4,

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] In another aspect, the present invention provides an organic electroluminescent material, which comprises the organic compound as described above.

[0047] On the other hand, the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the material of the organic layer comprises one or a combination of at least two of the organic compounds described above.

[0048] Preferably, the organic layer comprises one or a combination of at least two of a hole injection layer, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light emitting layer, an electron buffer layer, an electron transport layer and an electron injection layer.

[0049] Preferably, the electron transport layer comprises one or a combination of at least two of the organic compounds described above.

[0050] Preferably, the light-emitting layer comprises one or a combination of at least two of the organic compounds described above.

[0051] Preferably, the light-emitting layer further comprises an iridium-containing complex.

[0052] In another aspect, the present invention provides a product comprising the organic electroluminescent device as described above.

[0053] Preferably, the product is used in optoelectronics, medicine, biotechnology, optical fiber, lighting equipment, electronic photographic photoreceptor, photoelectric converter, organic solar cell, switching element, organic light emitting field effect transistor, image sensor or dye laser.

[0054] Compared with the prior art, the present invention has the following beneficial effects:

[0055] The organic electroluminescent compound provided by the present invention reduces the ring tension of the whole molecule through molecular modification, making the structure more stable, which is beneficial for the organic electroluminescent compound to show high electron mobility and improve the stability of the device. When the organic electroluminescent material provided by the present invention is used as the electron transport material or the main material of the organic electroluminescent device, it has the characteristics of high carrier mobility, so that the life of the device is improved; the HOMO and LUMO energy levels of the organic electroluminescent compound have a high matching degree with the adjacent energy levels, so that the organic electroluminescent compound obtains higher stability and the carrier mobility is more balanced, and thus the organic electroluminescent device containing the organic electroluminescent compound has lower driving voltage, higher luminous efficiency and longer life. BRIEF DESCRIPTION OF THE DRAWINGS

[0056] Figure 1 is a schematic structural diagram of the organic electroluminescent device of the present invention;

[0057] Among them, 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, 5 is a light emitting layer, 6 is an electron transport layer, 7 is an electron injection layer, and 8 is a cathode. DETAILED DESCRIPTION

[0058] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0059] Synthesis of compounds:

[0060]

[0061] Synthesis of intermediate 4-1: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube, add raw material 1 (1 mmol), raw material 6 (1.1 mmol), toluene (9 ml), water (3 ml), add tetrakistriphenylphosphine palladium (0.05 mmol), potassium carbonate (2 mmol), heat to 90 degrees Celsius, react for 5 hours, after the reaction is completed, cool to room temperature, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane volume ratio = 1:50) to obtain intermediate 4-1 (yield 75%).

[0062] MS (APCI) m / z [M+H] +: 484.21

[0063] Synthesis of compound 4: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube, add intermediate 4-1 (1 mmol), raw material 3 (1 mmol), toluene (9 ml), water (3 ml), add tetrakistriphenylphosphine palladium (0.05 mmol), potassium carbonate (2 mmol), heat to 90 degrees Celsius, react for 5 hours, after the reaction is completed, cool to room temperature, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane volume ratio = 1:50) to obtain compound 4 (yield 81%).

[0064] MS (APCI) m / z [M+H]+: 716.37.

[0065]

[0066] Synthesis of intermediate 8-1: The synthesis of intermediate 4-1 is the same as that of intermediate 4-1, except that raw material 2 is used instead of raw material 6 to obtain intermediate 8-1 (yield 72%). MS (APCI) m / z [M+H] +: 484.32.

[0067] Synthesis of compound 8: The synthesis was the same as that of compound 4, except that intermediate 8-1 was used instead of intermediate 4-1 to obtain compound 8 (yield 80%). MS (APCI) m / z [M+H] +: 716.30.

[0068]

[0069] Synthesis of compound 104: The synthesis was the same as compound 4, except that raw material 7 was used instead of raw material 3 to obtain compound 104 (yield 81%). MS (APCI) m / z [M+H] +: 791.30.

[0070]

[0071] Synthesis of intermediate 316-1: The synthesis of intermediate 4-1 is the same as that of intermediate 4-1, except that raw material 8 is used instead of raw material 1 to obtain intermediate 316-1 (yield 72%). MS (APCI) m / z [M+H] +: 484.16.

[0072] Synthesis of compound 316: The synthesis was the same as that of compound 4, except that intermediate 316-1 was used instead of intermediate 4-1, and raw material 7 was used instead of raw material 3 to obtain compound 316 (yield 80%). MS (APCI) m / z [M+H] +: 791.29.

[0073]

[0074] Synthesis of intermediate 391-1: The synthesis of intermediate 4-1 is the same as that of intermediate 4-1, except that raw material 4 is used instead of raw material 1 to obtain intermediate 391-1 (yield 75%). MS (APCI) m / z [M+H] +: 484.31.

[0075] Synthesis of compound 391: The synthesis was the same as that of compound 4, except that intermediate 391-1 was used instead of intermediate 4-1 to obtain compound 391 (yield 83%). MS (APCI) m / z [M+H] +: 716.27.

[0076]

[0077] Synthesis of intermediate 583-1: The synthesis of intermediate 4-1 is the same as that of intermediate 4-1, except that raw material 5 is used instead of raw material 1 to obtain intermediate 583-1 (yield 75%). MS (APCI) m / z [M+H] +: 484.26.

[0078] Synthesis of compound 583: The synthesis was the same as that of compound 4, except that intermediate 583-1 was used instead of intermediate 4-1 to obtain compound 583 (yield 83%). MS (APCI) m / z [M+H] +: 716.33.

[0079] Application Examples 1-6 and Comparative Application Example 1

[0080] The following application examples 1-6 and comparative application example 1 provide different OLEDs, and the structural schematic diagrams are as follows: Figure 1As shown, they all have the following layer structure: substrate 1 (coated glass substrate with indium tin oxide (ITO) as anode 2) / hole injection layer 3 (HIL) / hole transport layer 4 (HTL) / light-emitting layer 5 (EML) / electron transport layer 6 (ETL) / electron injection layer 7 (EIL), and finally cathode 8.

[0081] The materials used are as follows:

[0082]

[0083] The preparation of the organic electroluminescent device comprises the following steps:

[0084] (1) Substrate cleaning: The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), rinsed in deionized water, ultrasonically degreased in an acetone: ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light and ozone.

[0085] (2) Evaporation of organic light-emitting functional layer:

[0086] The glass substrate with the anode layer is placed in a vacuum chamber and evacuated to 1×10 -6 Up to 2×10 -4 Pa, vacuum evaporating a mixture of HATCN and HT on the above anode layer film, wherein the mass ratio of HATCN to HT is 3:97, as a hole injection layer, and the evaporation thickness is 10 nm;

[0087] A hole transport layer (made of HT) is evaporated on the hole injection layer, with a thickness of 80 nm.

[0088] The light-emitting layer is deposited on the hole transport layer. The specific preparation method is: vacuum-deposit the light-emitting host material (the materials are shown in Table 1) and the guest material (piq)2Ir(acac) in a co-evaporation manner, and the total film thickness of the deposition is 30 nm;

[0089] An electron transport layer is deposited on the light-emitting layer. The specific preparation method is as follows: ET and LiQ are vacuum deposited in a co-evaporation manner, and the total film thickness of the deposition is 30 nm;

[0090] An electron injection layer (made of LiQ) is vacuum-deposited on the electron transport layer, with a total film thickness of 1 nm.

[0091] Al was evaporated on the electron injection layer, and the total film thickness of the evaporated layer was 90 nm.

[0092] The parameters of each layer in the device, its material, thickness, etc. are shown in Table 1 below:

[0093] Table 1

[0094]

[0095]

[0096] Device performance test:

[0097] Test samples: organic electroluminescent devices provided in Application Examples 1-6 and Comparative Application Example 1;

[0098] Test instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K 2400 digital source meter system;

[0099] Test conditions: Photoelectric properties Test conditions: Current density is 10mA / cm 2 ;

[0100] Life test: current density is 50mA / cm 2 , record the time (in hours) when the device brightness drops to 95% of the original brightness;

[0101] The test results are shown in Table 2 below:

[0102] Table 2

[0103]

[0104]

[0105] It can be seen from the data in Table 2 that the organic compound of the present invention can enable the organic electroluminescent device to have a lower driving voltage (below 3.64V), a higher current efficiency (up to 19Cd / A or more) and a longer life (more than 265h).

[0106] The applicant declares that the present invention illustrates the organic compounds and applications of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of the raw materials selected by the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound having a structure shown in formula A: X is selected from O or NAr, Ar is selected from phenyl, biphenyl or naphthyl, L 1 -L 11 are each independently selected from a single bond or a naphthylene group, R 1 -R 11 Each independently selected from hydrogen, deuterium or The wavy lines represent the attachment sites of the groups. R' is selected from phenyl, biphenyl or naphthyl.

2. The organic compound according to claim 1, characterized in that L 1 -L 11 Each is independently selected from naphthylene, wherein the naphthylene is selected from any of the following groups, The numbers and wavy lines represent the attachment sites of the groups.

3. The organic compound according to claim 1 or 2, characterized in that: Selected from any of the following groups: The wavy line represents the attachment site of the group.

4. The organic compound according to any one of claims 1 to 3, characterized in that The organic compound has any of the following structures:

5. The organic compound according to any one of claims 1 to 4, characterized in that The organic compound is selected from any one of compounds 1-864, and the structure of compound 1-864 is formula 1 substituted by LR, wherein L is selected from L 1 -L 4 , R is selected from R 1 -R 4 , Formula 1 is one of Formula 1-1, Formula 1-2, Formula 1-3, and Formula 1-4, 6. An organic electroluminescent material, characterized in that: The organic electroluminescent material comprises the organic compound according to any one of claims 1 to 5.

7. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein a material of the organic layer comprises one or a combination of at least two of the organic compounds as described in any one of claims 1 to 5.

8. The organic electroluminescent device according to claim 7, characterized in that: The organic layer includes one or a combination of at least two of a hole injection layer, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light emitting layer, an electron buffer layer, an electron transport layer, and an electron injection layer.

9. The organic electroluminescent device according to claim 8, characterized in that: The electron transport layer comprises one or a combination of at least two of the organic compounds described in any one of claims 1 to 5; Preferably, the light-emitting layer comprises one or a combination of at least two of the organic compounds described in any one of claims 1 to 5; Preferably, the light-emitting layer further comprises an iridium-containing complex.

10. A product, characterized in that It comprises the organic electroluminescent device according to any one of claims 7 to 9.

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