Polycyclic compound containing triarylamine structure and organic electroluminescent device containing polycyclic compound

Abstract

The invention discloses a polycyclic compound containing a triarylamine structure, and the structural general formula is as shown in the formula I. The polycyclic compound containing the triarylamine structure is good in stability, and can effectively improve the luminous efficiency and the contrast ratio and remarkably improve the display effect by improving the material oscillator intensity and reducing the half-peak width of a luminescent spectrum and being used for a blue luminescent device. The defects in the prior art are overcome. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of OLED, and specifically comprises a polycyclic compound containing a triarylamine structure and an organic electroluminescent device containing the same. Background Art

[0002] Organic light emitting diode (OLED) is a very popular display technology. Due to the innovation of the structure of organic light emitting diodes and the use of efficient transmission materials, host materials, luminescent materials and injection materials, display and lighting applications based on OLED technology have become one of the most competitive technologies. Due to its high efficiency, light weight, high color display quality, viewing angle close to 180°, ultra-fast response and potential to achieve pure black display, OLED technology has attracted worldwide attention.

[0003] For full-color display research, the development of red phosphorescent OLED and green phosphorescent OLED has met the application requirements of the screen. Blue phosphorescent materials are difficult to achieve long life requirements in device applications due to their higher triplet energy level and wider band gap. Therefore, in organic electroluminescent devices, the application of blue fluorescent materials in OLED industrialization is becoming more and more important.

[0004] Existing OLED blue light fluorescent doping materials usually use pyrene compounds or boron-containing aromatic compounds. Boron-containing aromatic compounds use the multiple vibration effect (MR effect) to construct polycyclic aromatic compounds formed by condensing multiple aromatic rings with boron atoms and heteroatoms such as nitrogen and oxygen by using the opposite vibrations of boron and nitrogen and oxygen. Boron-containing aromatic compounds have obvious advantages over early pyrene materials, but their performance in half-peak width, color purity and luminous efficiency is not particularly ideal. It is urgent to develop a blue fluorescent organic electroluminescent material with high luminous efficiency and high color purity. Summary of the invention

[0005] In view of this, the present invention provides a polycyclic compound containing a triarylamine structure and an organic electroluminescent device containing the same. The polycyclic compound containing the triarylamine structure has good stability, can not only improve the oscillator strength of the material, but also can significantly improve the orientation factor of the material, and reduce the shoulder peak luminescence intensity of the luminescence spectrum. The polycyclic compound containing the triarylamine structure is used as a blue dopant in the organic light-emitting layer of the organic electroluminescent device. The blue dopant can effectively improve the luminous efficiency and contrast of the organic electroluminescent device, significantly improve the display effect, and overcome the defects of the prior art.

[0006] In order to achieve the above-mentioned object of the invention, the present invention adopts the following technical scheme: In the first aspect of the present invention, a polycyclic compound containing a triarylamine structure is provided, characterized in that the general structural formula of the compound is as shown in Formula I:

[0007]

[0008] in,

[0009] The ring M is selected from substituted or unsubstituted aryl groups having 5 to 60 carbon atoms;

[0010] The R1 is selected from any one or any combination of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms;

[0011] The R a Any one or any combination thereof selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted arylamine group having 18 to 30 carbon atoms;

[0012] The L1 is selected from a single bond or And n is selected from 0, 1, 2;

[0013] R2, R3, R4, R5, R6, and R7 are each independently selected from any one or any combination of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms;

[0014] When the rings M, R1 to R7, R a When any one of the rings M, R1 to R7, R aThe substituents may be one or more and each independently selected from deuterium, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, an alkylthio group having 1 to 15 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, an arylthio group having 6 to 12 carbon atoms, an alkylsulfonyl group having 6 to 12 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, a condensed ring aryl group having 10 to 30 carbon atoms, a condensed ring heteroaryl group having 9 to 30 carbon atoms, or a diarylamine group, wherein two or more substituents may be bonded to each other via a linking group or a single bond to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, a condensed ring, or a condensed heterocyclic ring;

[0015] Any hydrogen on the ring structure of the polycyclic compound containing a triarylamine structure as shown in Formula I can be independently replaced by deuterium, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group.

[0016] In combination with the first aspect, the ring M is selected from

[0017] The R8 is selected from any one or any combination of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0018] Preferably, R8 is selected from hydrogen, deuterium, and tert-butyl.

[0019] In combination with the first aspect, the R a Selected from

[0020] The L2 is selected from a single bond or and m is selected from 0, 1, and 2;

[0021] R9, R 10 , R 11 , R 12 , R 13 Any one or any combination thereof is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0022] Preferably, R9, R 10 , R 11 , R 12 , R 13 Selected from hydrogen, deuterium, methyl and tert-butyl.

[0023] In combination with the first aspect, the R1 is selected from hydrogen, deuterium, tert-butyl, Any one of the following: Any hydrogen on R1 can be independently replaced by deuterium.

[0024] In combination with the first aspect, the compound represented by formula I is selected from any one of the structures represented by formula I-1 to formula I-2 below:

[0025]

[0026] Any hydrogen on the ring structure of the polycyclic compound containing a triarylamine structure shown in Formula I-1 to Formula I-2 can be independently substituted by deuterium, alkyl, cycloalkyl, aryl or heteroaryl, preferably by deuterium, methyl, tert-butyl or phenyl.

[0027] In combination with the first aspect, the compound represented by formula I is selected from any one of the structures represented by the following formula I-1-1 to formula I-2-4:

[0028]

[0029] In the structures represented by Formula I-1-1 to Formula I-2-4, the n or m is independently selected from 1 or 2;

[0030] Any hydrogen on the ring structure of the polycyclic compound containing a triarylamine structure shown in Formula I-1-1 to Formula I-2-4 can be independently substituted by deuterium, alkyl, cycloalkyl, aryl or heteroaryl, preferably by deuterium, methyl, tert-butyl or phenyl.

[0031] In combination with the first aspect, the compound represented by formula I-1-1 to formula I-2-4 is any one of the following compounds:

[0032]

[0033]

[0034] Any hydrogen on the ring structure of the polycyclic compound containing a triarylamine structure shown in Formula I-1-1-1 to Formula I-2-4-2 can be independently substituted by deuterium, alkyl, cycloalkyl, aryl, heteroaryl or arylamino, preferably by deuterium, methyl, tert-butyl or phenyl.

[0035] In combination with the first aspect, the compound represented by formula I is selected from any one of the following compounds:

[0036]

[0037]

[0038]

[0039]

[0040]

[0041] The second aspect of the present invention provides the above-mentioned polycyclic compound containing a triarylamine structure for use in the field of organic electroluminescence.

[0042] The third aspect of the present invention provides an organic electroluminescent device, comprising an anode, a hole transport region, a light-emitting layer, an electron transport region and a cathode arranged in sequence on a substrate; wherein the light-emitting layer comprises a main material and a doping material, and the doping material comprises one or more polycyclic compounds containing a triarylamine structure as provided in the first aspect of the present invention.

[0043] The beneficial effects of the present invention are as follows:

[0044] The present invention provides a polycyclic compound containing multiple triarylamine structures, and the resonance effect can be enhanced by adding an aromatic amine substituent at the 20th position of the parent core structure, and the shoulder peak luminescence intensity can be reduced, but because this position is in the para position of the boron atom, the electron cloud density of the luminescence center will be affected. The present invention can not only weaken the influence of the aromatic amine substituent at the 20th position on the electron cloud density of the luminescence center by adding an aromatic amine substituent at the 15th and / or 26th position of the parent core structure, but also significantly improve the oscillator strength of the material; and the present invention has a breakthrough discovery that by adding a substituent at the 3rd, 15th, 20th, and 26th positions of the parent core structure, the planarity of the molecule can be significantly increased, the orientation factor of the molecule can be improved, and the luminescent material can be regularly arranged in the main material, thereby making the luminescence direction more concentrated; further, the present invention can further improve the oscillator strength on the one hand, and significantly improve the orientation factor of the material on the other hand by adding a biphenyl spacer between the aromatic amine substituent and the nitrogen atom.

[0045]

[0046] The polycyclic compound containing a triarylamine structure provided by the present invention is used as a blue dopant in the organic light-emitting layer of a blue light organic electroluminescent device. Since the polycyclic compound containing a triarylamine structure provided by the present invention can reduce the shoulder peak luminescence intensity, the efficiency of the organic electroluminescent device can be effectively improved. Since the polycyclic compound containing a triarylamine structure provided by the present invention has a high oscillator strength, the energy level transition within the molecule is more likely to occur, which is beneficial to the energy transfer of the host and guest materials. In addition, the molecule with a high oscillator strength can also enable the electrons in the material to release more energy faster after excitation, thereby effectively improving the luminescence efficiency of the blue light organic electroluminescent device. Since the polycyclic compound containing a triarylamine structure provided by the present invention has a high orientation factor, the luminescence direction can be more concentrated. When the luminescence direction is perpendicular to the substrate, the energy loss caused by the transmission of light in the device can be significantly reduced, thereby improving the luminescence efficiency and contrast of the blue light organic electroluminescent device, significantly improving the display effect, and overcoming the defects of the prior art. Description of the drawings:

[0047] The specific implementation modes of the present invention will be further described in detail below in conjunction with the accompanying drawings.

[0048] Figure 1 is a schematic structural diagram of an organic electroluminescent device containing the compound of the present invention;

[0049] Description of the drawings: 1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-luminescence auxiliary layer, 6-luminescent layer, 7-electron transport layer 1, 8-electron transport layer 2, 9-electron injection layer, 10-cathode. DETAILED DESCRIPTION

[0050] In order to more clearly illustrate the present invention, the present invention is further described below in conjunction with preferred embodiments and accompanying drawings. Similar components in the accompanying drawings are represented by the same figure numerals. It should be understood by those skilled in the art that the content specifically described below is illustrative and not restrictive, and the protection scope of the present invention should not be limited to this. The embodiments and comparative examples of this specification are provided to more completely explain this specification to those skilled in the art. According to the embodiments and comparative examples of this specification, various different forms can be deformed, and the protection scope of the present invention should not be limited only to the embodiments and comparative examples described in detail below.

[0051] The compounds of the present invention are suitable for use in light-emitting elements, display panels and electronic devices, and are particularly suitable for use in organic electroluminescent devices. The electronic device of the present invention is a device comprising a layer of at least one organic compound, which may also comprise an inorganic material or a layer formed entirely of an inorganic material. The electronic device is preferably an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic dye-sensitized solar cell (O-DSSC), an organic optical detector, an organic photoreceptor, an organic field quenching device (O-FQD), a light-emitting electrochemical cell (LEC), an organic laser diode (O-laser) and an organic plasma emission device. The electronic device is preferably an organic electroluminescent device (OLED).

[0052] In order to understand the content of the present invention more clearly, the polycyclic compound containing triarylamine structure, the preparation method of the compound and the luminescent characteristics of the device will be explained in detail in conjunction with the examples. Various chemical reactions can be applied to the synthesis method of the compound of one embodiment of the present invention. However, it should be noted that the synthesis method of the compound of one embodiment of the present invention is not limited to the synthesis method described below. Unless otherwise specified, the subsequent synthesis is carried out in anhydrous solvent under a protective gas atmosphere. Solvents and reagents can be purchased from conventional reagent suppliers. The compound of the present invention is prepared by using a representative reaction Buchwald-Hartwig coupling reaction, Suzuki coupling reaction or Heck coupling reaction.

[0053] Intermediate synthesis

[0054]

[0055] The general formula for the synthesis of the intermediate is as above. The target intermediate can be obtained by a two-step common Buchwald-Hartwig coupling synthesis method. The specific case is as follows:

[0056] Intermediate Example 1

[0057]

[0058] Sub1 (66.0 g; 100 mmol), Sub2 (37.2 g; 100 mmol) and sodium tert-butoxide (105 g, 110 mmol) were added to toluene (500 ml), and then bis(dibenzylideneacetonepalladium) (CAS No. 32005-36-0, 2.7 g, 3.0 mmol) and tri-tert-butylphosphine (1.2 g, 6.0 mmol) were introduced under nitrogen protection. The reaction system was then heated to reflux and maintained for 10 hours. After cooling to room temperature, water was added to quench and the liquids were separated. The organic phase was filtered and dried over anhydrous sodium sulfate. The solvent was removed by rotation, and the crude product was purified by column chromatography to obtain the product Sub3: 75.7 g (yield: 78%), MS (m / z) (M+): 971.

[0059]

[0060] Sub3 (75.7 g; 78 mmol), Sub4 (43.8 g; 78 mmol) and sodium tert-butoxide (77.0 g, 80 mmol) were added to toluene (500 ml), and then under nitrogen protection, bis(dibenzylideneacetone palladium) (2.2 g, 2.4 mmol) and 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (XantPhos, CAS No. 2161265-03, 8.7 g, 4.8 mmol) were introduced. The reaction system was then heated to reflux and maintained for 10 hours. After cooling to room temperature, water was added to quench and the liquids were separated. The organic phase was filtered and dried over anhydrous sodium sulfate. The solvent was removed by rotation, and the crude product was purified by column chromatography to obtain product A1: 49.2 g (yield: 45%), MS (m / z) (M+): 1406.

[0061] After intermediate A1 is obtained through the above process, other intermediates A2 to A13 can be obtained by using a method that is basically the same as the method for synthesizing intermediate A1, except that the reactants are different.

[0062] Compound Example 1

[0063] This example provides a compound B-1, the synthesis route of which is as follows:

[0064]

[0065] Under nitrogen protection, the system was maintained at -30°C to -40°C, and n-butyllithium solution (15.40mL, 20.00mmol) was slowly added dropwise to a solution of A1 (12.50g, 10mmol) in tert-butylbenzene (100mL), and then the temperature was raised to 60°C and stirred for 6 hours; the temperature was lowered to -30°C, boron tribromide (1.91mL, 20.00mmol) was added dropwise, and the temperature was raised to 60°C and stirred for 6 hours; the temperature was lowered to 0°C, and N,N-diisopropylethylamine (2.78mL, 20.0 0mmol), the reaction system was heated to room temperature 25°C and stirred for 2 hours; 150mL of deionized water was added to the reaction system, the mixture was extracted with 200mL of dichloromethane, the organic layers were combined, and the crude product was concentrated in vacuo to obtain the crude product, and the crude product was separated and purified by column chromatography (the mobile phase of the column chromatography was dichloromethane: petroleum ether = 1:20) to obtain a purified product, and the purified product was recrystallized from n-heptane, acetone and toluene to finally obtain 0.59g of product B-1, with a yield of 4.4%, MS (m / z) (M+): 1335.

[0066] Compound Example 2

[0067] This example provides a compound B-2, the synthesis route of which is as follows:

[0068]

[0069] The method is the same as Example 1, except that an equimolar amount of A2 (12.57 g; 10 mmol) is used to replace A1, and the final product B-2 is 0.40 g (yield: 3.4%), MS (m / z) (M+): 1186.3.

[0070] Compound Example 3

[0071] This example provides a compound B-3, the synthesis route of which is as follows:

[0072]

[0073] The method is the same as Example 1, except that an equimolar amount of A3 (11.81 g; 10 mmol) is used to replace A1, and the final product B-3 is 0.41 g (yield: 3.6%), MS (m / z) (M+): 1110.2.

[0074] Compound Example 4

[0075] This example provides a compound B-4, the synthesis route of which is as follows:

[0076]

[0077] The method is the same as Example 1, except that an equimolar amount of A4 (12.65 g; 10 mmol) is used to replace A1, and the final product B-4 is 0.57 g (yield: 4.8%), MS (m / z) (M+): 1194.4.

[0078] Compound Example 5

[0079] This example provides a compound B-5, the synthesis route of which is as follows:

[0080]

[0081] The method is the same as Example 1, except that an equimolar amount of A5 (13.90 g; 10 mmol) is used to replace A1, and the final product B-5 is 0.46 g (yield: 3.5%), MS (m / z) (M+): 1318.5.

[0082] Compound Example 6

[0083] This example provides a compound B-6, the synthesis route of which is as follows:

[0084]

[0085] The method is the same as Example 1, except that an equimolar amount of A6 (13.87 g; 10 mmol) is used to replace A1, and the final product B-6 is 0.65 g (yield: 4.9%), MS (m / z) (M+): 1316.5.

[0086] Compound Example 7

[0087] This example provides a compound B-7, the synthesis route of which is as follows:

[0088]

[0089] The method is the same as Example 1, except that an equimolar amount of A7 (13.41 g; 10 mmol) is used to replace A1, and the final product B-7 is 0.63 g (yield: 5.0%), MS (m / z) (M+): 1270.5.

[0090] Compound Example 8

[0091] This example provides a compound B-8, the synthesis route of which is as follows:

[0092]

[0093] The method is the same as Example 1, except that an equimolar amount of A8 (13.91 g; 10 mmol) is used to replace A1, and the final product B-8 is 0.94 g (yield: 7.1%), MS (m / z) (M+): 1319.7.

[0094] Compound Example 9

[0095] This example provides a compound B-9, the synthesis route of which is as follows:

[0096]

[0097] The method is the same as Example 1, except that an equimolar amount of A9 (14.45 g; 10 mmol) is used to replace A1, and the final product B-9 is 0.44 g (yield: 3.2%), MS (m / z) (M+): 1373.8.

[0098] Compound Example 10

[0099] This example provides a compound B-10, the synthesis route of which is as follows:

[0100]

[0101] The method is the same as Example 1, except that an equimolar amount of A10 (13.00 g; 10 mmol) is used to replace A1, and the final product B-10 is 0.56 g (yield: 4.5%), MS (m / z) (M+): 1228.6.

[0102] Compound Example 11

[0103] This example provides a compound B-11, the synthesis route of the compound is as follows:

[0104]

[0105] The method is the same as Example 1, except that an equimolar amount of A11 (14.25 g; 10 mmol) is used to replace A1, and the final product B-11 is 0.81 g (yield: 6.0%), MS (m / z) (M+): 1353.8.

[0106] Compound Example 12

[0107] This example provides a compound B-12, the synthesis route of which is as follows:

[0108]

[0109] The method is the same as Example 1, except that an equimolar amount of A12 (12.35 g; 10 mmol) is used to replace A1, and the final product B-12 is 0.75 g (yield: 6.5%), MS (m / z) (M+): 1164.3.

[0110] Compound Example 13

[0111] This example provides a compound B-13, the synthesis route of which is as follows:

[0112]

[0113] The method is the same as Example 1, except that an equimolar amount of A13 (12.57 g; 10 mmol) is used to replace A1, and the final product B-13 is 0.78 g (yield: 6.6%), MS (m / z) (M+): 1186.3.

[0114] Compound Comparative Example 1

[0115] This comparative example provides a compound BD1 that has been tested during the research process, and its specific structural formula is:

[0116]

[0117] Compound Comparative Example 2

[0118] This comparative example provides a compound BD2 that has been tested during the research process, and its specific structural formula is:

[0119]

[0120] Effect example

[0121] The polycyclic compound containing a triarylamine structure provided by the present invention has a high oscillator strength. The oscillator strength is a dimensionless quantity. The magnitude of the oscillator strength reflects the difficulty of the energy level transition inside the molecule when the material is excited. The larger the value, the easier it is to be excited, and thus the more conducive to the energy transfer of the host and guest materials. Using the delayed density functional method (TDDFT), the oscillator strength of the molecule is calculated at an accuracy of 6-31G*. The specific calculation results are shown in Table 1:

[0122] The polycyclic compound containing a triarylamine structure provided by the present invention has a good alignment factor. The optical path diagram and the alignment factor S value are measured using a Hamamatsu C14234-11 molecular alignment test system. The specific test results are shown in Table 1:

[0123] Table 1 Oscillator strength and orientation factor of the compounds

[0124]

[0125]

[0126]

[0127] It can be seen from the calculation results in Table 1 above that, compared with the comparative example compounds, the polycyclic compounds containing triarylamine structures provided by the present invention have obvious advantages in oscillator strength.

[0128] Compared with BD1 of the comparative example, the compounds B-1 to B-4 provided by the present invention, by adding aromatic amine substituents at positions 15 and 26 of the parent core structure, can not only improve the influence of the aromatic amine substituent at position 20 on the electron cloud density of the luminescent center, but also significantly improve the oscillator strength of the material; compared with BD2 of the comparative example, the compounds B-1 to B-4 provided by the present invention, by adding aromatic amine substituents at position 20 of the parent core structure, can enhance the resonance effect, reduce the shoulder peak luminescence intensity, and improve the efficiency of the organic electroluminescent device. Further, by adding substituents at positions 3, 15, 20, and 26 of the parent core structure, the planarity of the molecule can be significantly increased, the luminescent material is arranged regularly in the main material, and the luminescent material is arranged in a certain direction, which can make the luminescent direction more concentrated. When the luminescent direction is perpendicular to the substrate, the energy loss caused by the transmission of light in the device can be significantly reduced, thereby improving the luminescent efficiency of the luminescent material in the device.

[0129] Compared with BD2 of the comparative example, the compounds B-5 and B-6 provided by the present invention can further improve the oscillator strength on the one hand, and can significantly improve the orientation factor of the material on the other hand by adding a biphenyl spacer between the aromatic amine substituent and the nitrogen atom at positions 15 and 26. The polycyclic compound containing a triarylamine structure provided by the present invention is applied as a blue dopant to the organic light-emitting layer of a blue light organic electroluminescent device. Since the polycyclic compound containing a triarylamine structure provided by the present invention has a high oscillator strength, the energy level transition within the molecule is more likely to occur, which is beneficial to the energy transfer of the host-guest material, and the molecule with high oscillator strength can also enable the electrons in the material to release more energy faster after excitation, thereby effectively improving the luminous efficiency of the blue light organic electroluminescent device; since the polycyclic compound containing a triarylamine structure provided by the present invention has a high orientation factor, the luminous direction can be more concentrated, and when the luminous direction is perpendicular to the substrate, the energy loss caused by the transmission of light in the device can be significantly reduced, further improving the luminous efficiency of the blue light organic electroluminescent device, and improving the contrast of the OLED device.

[0130] Device Embodiment

[0131] The organic electroluminescent device of the following embodiment includes an anode 2, a hole transport region, a light-emitting layer 5, an electron transport region, and a cathode 8 arranged in sequence on a substrate 1; wherein: the hole transport region includes a hole transport layer 3 and a light-emitting auxiliary layer 4; the electron transport region includes an electron transport layer 6 and an electron injection layer 7; the light-emitting layer 5 is composed of a host and a doped guest, and the host of the light-emitting layer can be composed of one molecular material or multiple molecular materials. The typical structure of an organic electroluminescent device is as follows Figure 1 shown.

[0132] The anode of the following embodiments adopts anode materials commonly used in the art, such as ITO, Ag or their multilayer structures. The hole injection unit adopts hole injection materials commonly used in the art, and F4TCNQ, HATCN, NDP-9, etc. are added for doping. The hole transport unit adopts hole transport materials commonly used in the art. The light-emitting unit adopts light-emitting materials commonly used in the art, for example, it can be composed of a host material and an emitted guest material doped, and the emitted guest material can be an organic material such as a pyrene compound, or it can be a metal complex (such as metal Ir, Pt, etc.). The electron transport unit adopts electron transport materials commonly used in the art. The electron injection layer adopts electron injection materials commonly used in the art, such as Liq, LiF, Yb, etc. The cathode adopts materials commonly used in the art, such as metal Al, Ag or metal mixtures (Ag-doped Mg, Ag-doped Ca, etc.).

[0133] The electrode preparation methods and the deposition methods of each functional layer in the following embodiments are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, etc., which will not be described in detail here. Only some process details and test methods in the preparation process are supplemented as follows:

[0134] Device Example 1

[0135] The present embodiment provides a blue light organic electroluminescent device, and the preparation method thereof is as follows: first, on the ITO layer (anode) formed on the substrate, HTL-1 and F4TCNQ (the mass ratio of HTL-1 to F4TCNQ is 97:3) are vacuum deposited with a thickness of 10 nm to form a hole injection layer; secondly, on the hole injection layer, HTL-1 is vacuum deposited with a thickness of 120 nm to form a hole transport layer; secondly, on the hole transport layer, HTL-2 is vacuum deposited with a thickness of 10 nm to form a light-emitting auxiliary layer; thirdly, on the light-emitting auxiliary layer, a mixture of BH and compound B-1 provided in compound embodiment 1 is vacuum deposited with a thickness of 20 nm. A light-emitting layer is formed by vacuum depositing ET-01 with a thickness of 5 nm on the light-emitting layer to form an electron transport layer 1, and vacuum depositing ET-02 and Liq (the mass ratio of ET-02 to Liq is 1:1) with a thickness of 30 nm to form an electron transport layer 2; then, LiF is deposited with a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and finally, aluminum (Al) is deposited with a thickness of 150 nm on the electron injection layer to form a cathode, thereby preparing a blue light-emitting organic electroluminescent device.

[0136] Except for the blue light doping material, the molecular structures of the remaining layers of materials are as follows:

[0137]

[0138] Device Examples 2-13

[0139] This embodiment provides a blue light organic electroluminescent device, and its preparation method is: the compound B-1 in the blue light device embodiment 1 is replaced by the compounds B-2 to B-13 provided in the compound embodiments 2 to 13 to form a light-emitting layer, and the other preparation steps are the same as those in the blue light device embodiment 1, and the blue light organic electroluminescent devices are prepared respectively.

[0140] Device Comparison Example 1-2

[0141] The method is the same as that of device example 1, except that compound B-1 in example 1 is replaced by compounds BD1 and BD2 provided in compound comparative examples 1 to 2, respectively.

[0142] Performance evaluation of organic electroluminescent devices

[0143] The organic electroluminescent devices provided in device examples 1-13 and device comparative examples 1-2 were tested by standard methods. 2The driving voltage, brightness, electroluminescent current efficiency (measured in cd / A) and external quantum efficiency (EQE, measured in percentage) of the organic electroluminescent device are determined at a current density of 500 mA / cm2, which are calculated from a current / voltage / luminescent density characteristic line (IVL characteristic line) showing Lambertian emission characteristics as a function of luminous density. The lifetime LT is defined as the time after which the brightness drops from the initial luminous brightness L0 to a specific proportion L1 when operating at a constant current J; J = 50 mA / cm2 2 The expression L1 = 90% means that at 50 mA / cm 2 When working under LT, the luminance drops to 90% of its initial value L0 after time LT. Similarly, J = 20 mA / cm 2 , L1 = 80% means, at 20mA / cm 2 When working under LT, the luminous brightness drops to 80% of its initial value L0 after time LT.

[0144] The data of various OLED devices are summarized in Table 1. Various parameters of the embodiments are compared with those of the comparative examples, and the performance data of various OLED devices are shown.

[0145] The test instruments and methods for testing the performance of the OLED devices in the above embodiments and comparative examples are as follows:

[0146] Brightness was tested using a spectral scanner PhotoResearch PR-635;

[0147] Current density and lighting voltage: tested using a digital source meter Keithley 2400;

[0148] Life test: Use LT-96ch life test device.

[0149] The performance test results of the above devices are listed in Table 2.

[0150] Table 2 Blue light device performance test results

[0151]

[0152] It can be seen from the device performance test results in Table 2 that, compared with the comparison compounds BD1 and BD2, the luminous efficiency of the organic electroluminescent device using the polycyclic compound containing a triarylamine structure provided by the present invention as a blue light doping material is significantly improved, the driving voltage is significantly reduced, and it also has a certain life advantage. This shows that the polycyclic compound containing a triarylamine structure provided by the present invention solves the technical problems of the limitations of the current OLED blue light doping materials in terms of luminous efficiency and service life. In addition, the organic electroluminescent device using the polycyclic compound containing a triarylamine structure provided by the present invention as a blue light dopant also has the advantages of higher light stability, stronger brightness and better color saturation, which can meet the needs of future high-performance display devices and has important application prospects. This shows that the polycyclic compound containing a triarylamine structure provided by the present invention is a blue dopant material with good performance, which can meet the performance requirements of blue organic electroluminescent devices and has practical value.

[0153] The above is only a preferred specific embodiment of the present invention, but the protection scope of the present invention is not limited thereto. Any changes or substitutions that can be easily thought of by a person skilled in the art within the technical scope disclosed by the present invention should be included in the protection scope of the present invention. Therefore, the protection scope of the present invention should be based on the protection scope of the claims.

Claims

1. A polycyclic compound containing a triarylamine structure, characterized in that: The general structural formula of the compound is shown in Formula I: in, The ring M is selected from substituted or unsubstituted aryl groups having 5 to 60 carbon atoms; The R1 is selected from any one or any combination of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; The R a Any one or any combination thereof selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted arylamine group having 18 to 30 carbon atoms; The L1 is selected from a single bond or And n is selected from 0, 1, 2; R2, R3, R4, R5, R6, and R7 are each independently selected from any one or any combination of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; When the rings M, R1 to R7, R a When any one of the rings M, R1 to R7, R a The substituents may be one or more and each independently selected from deuterium, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, an alkylthio group having 1 to 15 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryloxy group having 6 to 12 carbon atoms, an arylthio group having 6 to 12 carbon atoms, an alkylsulfonyl group having 6 to 12 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, a condensed ring aryl group having 10 to 30 carbon atoms, a condensed ring heteroaryl group having 9 to 30 carbon atoms, or a diarylamine group, wherein two or more substituents may be bonded to each other via a linking group or a single bond to form an aliphatic ring, an aromatic ring, a heteroaromatic ring, a condensed ring, or a condensed heterocyclic ring; Any hydrogen on the ring structure of the polycyclic compound containing a triarylamine structure as shown in Formula I can be independently replaced by deuterium, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group.

2. The polycyclic compound containing a triarylamine structure according to claim 1, characterized in that: The ring M is selected from The R8 is selected from any one or any combination of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

3. The polycyclic compound containing a triarylamine structure according to claim 1, characterized in that: The R a Selected from The L2 is selected from a single bond or and m is selected from 0, 1, and 2; R9, R 10 , R 11 , R 12 , R 13 Any one or any combination thereof is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

4. The polycyclic compound containing a triarylamine structure according to claim 1, characterized in that: The R1 is selected from hydrogen, deuterium, tert-butyl, Any one of the following: Any hydrogen on R1 can be independently replaced by deuterium.

5. The polycyclic compound containing a triarylamine structure according to claim 1, characterized in that: The compound represented by formula I is selected from any one of the structures represented by formula I-1 to formula I-2 below: Any hydrogen on the ring structure of the polycyclic compound containing a triarylamine structure represented by Formula I-1 to Formula I-2 can be independently replaced by deuterium, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group.

6. The polycyclic compound containing a triarylamine structure according to claim 5, characterized in that: The compound represented by formula I is selected from any one of the structures represented by the following formula I-1-1 to formula I-2-4: In the structures represented by Formula I-1-1 to Formula I-2-4, the n or m is independently selected from 1 or 2; Any hydrogen on the ring structure of the polycyclic compounds containing a triarylamine structure represented by Formula I-1-1 to Formula I-2-4 can be independently replaced by deuterium, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group.

7. The polycyclic compound containing a triarylamine structure according to claim 6, characterized in that: The compounds represented by formula I-1-1 to formula I-2-4 are any one of the following compounds: Any hydrogen on the ring structure of the polycyclic compounds containing a triarylamine structure represented by Formula I-1-1-1 to Formula I-2-4-2 can be independently substituted by deuterium, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group or an arylamino group.

8. The polycyclic compound containing a triarylamine structure according to claim 1, characterized in that: The compound represented by formula I is selected from any one of the following compounds:

9. The polycyclic compound containing a triarylamine structure according to any one of claims 1 to 8, characterized in that: The polycyclic compound containing a triarylamine structure is applied in the field of organic electroluminescence.

10. An organic electroluminescent device, characterized in that: It includes an anode, a hole transport region, a light-emitting layer, an electron transport region and a cathode arranged in sequence on a substrate; wherein the light-emitting layer includes a main material and a doping material, and the doping material includes one or more polycyclic compounds containing a triarylamine structure as described in any one of claims 1 to 8.

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