Organic electroluminescent material composition and organic electroluminescent device containing same

Abstract

The invention provides an organic electroluminescent material composition and an organic electroluminescent device comprising the same, the composition comprises a first compound shown in a chemical formula I and a second compound shown in a chemical formula II, a layer where the first compound is located is tightly attached to a layer where the second compound is located, the energy level of the composition is matched, and the energy level of the composition is matched with the energy level of the second compound. The absolute value of the energy range delta HOMO is small, and the hole mobility and the interface contact condition are good; the first compound provided by the invention is used as a hole transport layer, and the second compound is used as a light-emitting auxiliary layer to be applied to the organic electroluminescent device, so that the organic electroluminescent material composition can obviously reduce the driving voltage of the organic electroluminescent device, improve the current efficiency of the organic electroluminescent device, and improve the luminous efficiency of the organic electroluminescent device. According to the organic electroluminescent material composition provided by the invention, the service life of the organic electroluminescent device is prolonged, and the threshold voltage of the organic electroluminescent device can be improved, so that the crosstalk phenomenon is effectively avoided, and the defects in the prior art are overcome. [Chemical Formula I] # imgabs0 # [Chemical Formula II] # imgabs1 #

Description

Technical Field

[0001] The present invention belongs to the technical field of OLED, and in particular relates to an organic electroluminescent material composition and an organic electroluminescent device comprising the same. Background Art

[0002] As a new generation of flat panel display technology, organic electroluminescent devices have many advantages such as self-luminescence, low driving voltage, low power consumption, fast response speed, high color purity, simple preparation process, wide viewing angle, rollability, and environmental friendliness, making them one of the hottest topics in the field of information display. Organic electroluminescent devices can be used in various fields such as televisions, smart phones, smart wearables, small displays, and indoor lighting. At present, almost all internationally renowned electronics and chemical companies have invested huge manpower and financial resources in the research and development of organic electroluminescent device materials and product development. Organic electroluminescent devices have become one of the most competitive frontier scientific fields in the world.

[0003] Organic electroluminescent devices are usually composed of an ITO transparent anode, a hole transport layer, an organic light-emitting layer, an electron transport layer and a metal cathode. Among them, the hole transport layer can enhance the hole transport ability of the device, reduce the energy barrier of holes during the injection process, ensure that holes can be effectively injected and transported between the functional layers, and block electrons in the light-emitting layer to achieve maximum recombination between carriers and improve luminescence efficiency. However, existing hole transport materials all have a low highest occupied molecular orbital (HOMO) value. The excitons generated in the light-emitting layer can easily diffuse to the hole transport layer interface or the hole transport layer side, resulting in luminescence at the interface of the light-emitting layer or charge imbalance in the light-emitting layer, which reduces the color purity and efficiency of the organic electroluminescent device, and ultimately leads to reduced luminescence efficiency and shortened service life of the organic electroluminescent device. In order to solve this problem, it is necessary to add a luminescent auxiliary layer between the hole transport layer and the light-emitting layer. The luminescent auxiliary layer can block the excitons from diffusing to the hole transport layer interface or the hole transport layer side, avoiding luminescence at the interface of the light-emitting layer. However, the HOMO energy level of the existing light-emitting auxiliary layer material cannot match the HOMO energy level of the existing hole transport layer material, thereby increasing the driving voltage of the organic electroluminescent device.

[0004] Since the pixel points corresponding to the three colors of red, green and blue have different turn-on voltages, when a certain pixel is lit, the adjacent pixels that share the hole transport layer also have lateral current transmission. If the turn-on voltage of red light is too small or the turn-on voltage of blue light is too large, the adjacent pixels will be lit secretly. When the organic electroluminescent devices of the three colors are made into OLED display panels to display images, if part of the pixel area in the display panel is lit, the adjacent pixel area that should not be lit will also emit light slightly, reducing the display effect of the display panel. It is urgent to develop a new type of organic material for organic electroluminescent devices. Summary of the invention

[0005] In view of this, the present invention provides an organic electroluminescent material composition and an organic electroluminescent device comprising the same. The organic electroluminescent material composition comprises a first compound and a second compound, and the layer formed by the first compound and the layer formed by the second compound are tightly attached. The organic electroluminescent material composition provided by the present invention has energy level matching, a small absolute value of the energy range difference ΔHOMO, and good hole mobility and interface contact. The first compound provided by the present invention is used as a hole transport layer, and the second compound is used as a light-emitting auxiliary layer in an organic electroluminescent device. The organic electroluminescent material composition can significantly reduce the driving voltage of the organic electroluminescent device, improve the current efficiency of the organic electroluminescent device, and extend the life of the organic electroluminescent device. The organic electroluminescent material composition provided by the present invention can also increase the threshold voltage of the organic electroluminescent device, thereby effectively avoiding the occurrence of crosstalk, thereby overcoming the defects of the prior art.

[0006] In order to achieve the above-mentioned object, the present invention adopts the following technical solution: In a first aspect, the present invention provides an organic electroluminescent material composition, the composition comprises a first compound and a second compound, the first compound and the second compound are closely attached, wherein the first compound is as shown in Chemical Formula I:

[0007] [Chemical formula I]

[0008]

[0009] In the chemical formula I, Ar1 and Ar2 are selected from any one or any combination of substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted condensed ring aryl groups having 10 to 30 carbon atoms;

[0010] The second compound is shown in Chemical Formula II:

[0011] [Chemical formula II]

[0012]

[0013] In the chemical formula II, Ar3 and Ar4 are selected from any one or any combination of substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, substituted or unsubstituted condensed ring aryl having 10 to 30 carbon atoms, and substituted or unsubstituted condensed ring heteroaryl having 9 to 30 carbon atoms;

[0014] When Ar1, Ar2, Ar3, Ar4 have substituents, the substituents of Ar1, Ar2, Ar3, Ar4 are independently selected from any one or a combination of deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; two or more adjacent substituents may be bonded to each other through a linking group or a single bond to form an aliphatic ring having 6 to 15 carbon atoms or an aromatic ring having 6 to 30 carbon atoms;

[0015] Any hydrogen on the first compound and the second compound can be independently replaced by deuterium, alkyl or cycloalkyl.

[0016] In combination with the first aspect, Ar1 and Ar2 in the first compound are selected from any one of phenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, and alkylphenyl.

[0017] In combination with the first aspect, the first compound is selected from any one of the structures shown in the following formula I-1 to formula I-5:

[0018]

[0019] The number of R1 and R2 is one or more, and each is independently selected from one or a combination of two of hydrogen, deuterium, adamantyl or phenyl.

[0020] In combination with the first aspect, the first compound is selected from any one of the following compounds C-1 to C-30:

[0021]

[0022]

[0023]

[0024] In combination with the first aspect, Ar3 and Ar4 in the second compound are selected from any one of phenyl, alkylphenyl, 9,9-dimethylfluorenyl, dimethylbenzofluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirobifluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, spiro[fluorene-9,9'-oxanthene]yl and spiro[fluorene-9,9'-thioanthene]yl.

[0025] In combination with the first aspect, the second compound is selected from any one of the structures shown in the following formula II-1 to formula II-15:

[0026]

[0027]

[0028] The number of R3, R4, R5, R6, R7 and R8 is one or more, and each is independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a phenyl group having 6 to 30 carbon atoms or an adamantyl group, or a combination of two of them; wherein two or more adjacent substituents may be bonded to each other through a linking group or a single bond to form any one or a combination of any several of an aliphatic ring having 6 to 15 carbon atoms, an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 5 to 30 carbon atoms, a condensed aromatic group having 10 to 30 carbon atoms, and a condensed heteroaromatic group having 9 to 30 carbon atoms; and X is selected from O or S.

[0029] In combination with the first aspect, the second compound is selected from any one of the following compounds F-1 to F-40:

[0030]

[0031]

[0032] A second aspect of the present invention provides an organic electroluminescent device, comprising an anode sequentially arranged on a substrate;

[0033] A cathode, disposed face to face with the anode;

[0034] A light-emitting layer, located between the anode and the cathode;

[0035] a hole transport layer located between the anode and the light-emitting layer; and

[0036] A light-emitting auxiliary layer, located between the light-emitting layer and the hole transport layer;

[0037] The hole transport layer comprises one or more first compounds described in the first aspect.

[0038] In combination with the second aspect, the light-emitting auxiliary layer comprises one or more second compounds described in the first aspect.

[0039] The beneficial effects of the present invention are as follows:

[0040] The present invention provides an organic electroluminescent material composition and an organic light-emitting device comprising the same. The organic material composition comprises a first compound and a second compound that are closely attached. The first compound provided by the present invention contains a fragment A, which has a large planar long conjugated carbazole structure, and the terphenyl structure connected by the nitrogen atom and the carbazole structure present a certain angle due to steric hindrance, so that the carbazole ring retains a large electron cloud density. The fragment A can ensure that the first compound has a good hole mobility on the one hand, and on the other hand, it plays a role in regulating the orbital energy level of the triarylamine material; the second compound provided by the present invention contains a fragment B, and the four phenyl substituents of the fragment are all ortho-substituted, and the fragment B has both large steric hindrance and high electron cloud density;

[0041]

[0042] The energy levels of the first compound and the second compound provided by the present invention are matched, the absolute value of the energy range difference ΔHOMO is small, the potential barrier is small, and the accumulation of holes at the interface of the two layers can be effectively avoided, so that the holes can quickly diffuse to the light-emitting area for recombination, thereby reducing the driving voltage of the organic electroluminescent device; in addition, the organic electroluminescent material composition provided by the present invention is more suitable in terms of hole mobility and interface contact, and the holes can be uniformly and stably diffused from the hole transport material to the electron blocking material, which can significantly reduce the driving voltage of the organic electroluminescent device; finally, the first compound provided by the present invention has a large hole reorganization energy λh, and the first compound and the second compound have ... small hole reorganization energy λh, and the first compound and the second compound have a small hole reorganization energy λh, and the first compound and the second compound have a small hole reorganization energy λh, and the first compound and the second compound have a small hole reorganization energy λh, and the first compound and the second compound have a small hole reorganization energy λh, and the first compound and the second compound have a small hole reorganization energy The second compound provided by the present invention can be used together to block electron diffusion and increase the threshold voltage, thereby avoiding the occurrence of crosstalk. The first compound provided by the present invention is used as a hole transport layer, and the second compound is used as a light-emitting auxiliary layer in an organic electroluminescent device. The organic electroluminescent material composition can significantly reduce the driving voltage of the organic electroluminescent device, improve the current efficiency of the organic electroluminescent device, and extend the life of the organic electroluminescent device. The organic electroluminescent material composition provided by the present invention can also increase the threshold voltage of the organic electroluminescent device, thereby effectively avoiding the occurrence of crosstalk, thereby overcoming the defects of the prior art. Description of the drawings:

[0043] The specific implementation modes of the present invention are further described in detail below in conjunction with the accompanying drawings.

[0044] Figure 1 is a schematic structural diagram of an organic electroluminescent device containing the polycyclic compound of the present invention;

[0045] 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, 8-electron injection layer, 9-cathode.

[0046] Among them, the hole injection layer 3, the hole transport layer 4, and the light-emitting auxiliary layer 5 constitute a hole transport region; the electron transport layer 7 and the electron injection layer 8 constitute an electron transport region. DETAILED DESCRIPTION

[0047] In order to more clearly illustrate the present invention, the present invention is further described below in conjunction with preferred embodiments and accompanying drawings. 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, and can be deformed into various different forms according to the embodiments and comparative examples of this specification, and the protection scope of the present invention should not be limited only to the embodiments and comparative examples described in detail below.

[0048] 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).

[0049] In order to understand the content of the present invention more clearly, the first compound, the second compound, the preparation method of the first compound and the second 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 synthetic method of the compound of one embodiment of the present invention. However, it should be noted that the synthetic method of the compound of one embodiment of the present invention is not limited to the synthetic method described below. Unless otherwise stated, the subsequent synthesis is carried out in an anhydrous solvent under a protective gas atmosphere. Solvents and reagents can be purchased from conventional reagent suppliers.

[0050] Synthesis of compound intermediates

[0051] Intermediate Example 1

[0052]

[0053] Under nitrogen protection, J-1 (24.80 g, 0.1 mol), potassium hydroxide (8.40 g, 0.15 mol) and K-1 (24.60 g, 0.1 mol) were added to a 1.5 L round-bottom flask, followed by addition of dimethyl sulfoxide (500 mL), and the temperature was slowly raised to 160 ° C and maintained for 24 h, then lowered to 25 ° C, 5 L of water was added and the liquids were separated to obtain an aqueous phase and a first organic phase. The aqueous phase was extracted with dichloromethane to obtain a second organic phase. The first organic phase was combined with the second organic phase and dehydrated with anhydrous sodium sulfate. The solvent was removed by rotation and purified by column chromatography to finally obtain A-1: ​​34.60 g, with a yield of 73%, a purity of 99%, and MS (m / z) (M+): 474.

[0054] Intermediate Example 2

[0055]

[0056] Under nitrogen protection, G-1 (71.80 g, 0.2 mol), potassium carbonate (69 g, 0.5 mol), PdCl2(PPh3)2 (2.81 g, 4 mmol) and H-1 (47.52 g, 0.24 mol) were added to a 2 L round-bottom flask, followed by addition of toluene (335 mL), deionized water (85 mL) and ethanol (85 mL), and the temperature was slowly raised to 80 ° C. and maintained for 16 h. The reaction was confirmed to be completed by TLC spotting. The temperature was cooled to room temperature, 1 L of water was added and the liquids were separated to obtain an aqueous phase and a first organic phase. The aqueous phase was extracted with dichloromethane to obtain a second organic phase. The first organic phase and the second organic phase were combined and dehydrated with anhydrous sodium sulfate. The solvent was removed by rotation and purified by column chromatography to finally obtain D-1: 61.60 g, with a yield of 80%, a purity of 99%, and MS (m / z) (M+): 385.

[0057] First Compound Synthesis Example

[0058] Example 1

[0059] This example provides a compound C-1, the synthesis route of which is as follows:

[0060]

[0061] A-1 (4.74 g, 10 mmol), B-1 (3.21 g, 10 mmol) and sodium tert-butoxide (1.06 g, 11 mmol) were added to toluene (100 mL), and then bis(dibenzylideneacetonepalladium) (0.01 g, 0.1 mmol) and tri-tert-butylphosphine (0.01 g, 0.2 mmol) were introduced under nitrogen protection, and then the reaction system was heated to 110°C, refluxed and maintained for 8 hours, cooled to room temperature, 100 mL of water was added to quench the reaction and separate the liquids to obtain an organic phase, 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. Finally, the product C-1: 4.93 g (yield: 69%), MS (m / z) (M+): 715 was obtained.

[0062] Example 2

[0063] This embodiment provides a compound C-2, the synthesis route of which is as follows:

[0064]

[0065] Using the same method as Example 1, an equimolar amount of B-2 (3.61 g, 10 mmol) was used to replace B-1, and finally the product C-2 was obtained: 5.21 g (yield: 69%), MS (m / z) (M+): 755.

[0066] Example 3

[0067] This example provides a compound C-3, the synthesis route of which is as follows:

[0068]

[0069] Using the same method as Example 1, an equimolar amount of B-3 (3.21 g, 10 mmol) was used to replace B-1, and finally the product C-3 was obtained: 5.65 g (yield: 79%), MS (m / z) (M+): 715.

[0070] Example 4

[0071] This example provides a compound C-4, the synthesis route of which is as follows:

[0072]

[0073] Using the same method as Example 1, an equimolar amount of B-4 (3.80 g, 10 mmol) was used to replace B-1, and finally the product C-4 was obtained: 5.57 g (yield: 72%), MS (m / z) (M+): 773.

[0074] Example 5

[0075] This embodiment provides a compound C-5, the synthesis route of the compound is as follows:

[0076]

[0077] Using the same method as Example 1, an equal molar amount of B-5 (3.61 g, 10 mmol) was used to replace B-1, and finally the product C-5 was obtained: 5.81 g (yield: 77%), MS (m / z) (M+): 755.

[0078] Second Compound Synthesis Example

[0079] Example 6

[0080] This example provides a compound F-1, the synthesis route of which is as follows:

[0081]

[0082] D-1 (3.85 g, 10 mmol), E-1 (5.24 g, 10 mmol) and sodium tert-butoxide (1.06 g, 11 mmol) were added to toluene (100 mL), and then bis(dibenzylideneacetonepalladium) (0.01 g, 0.1 mmol) and tri-tert-butylphosphine (0.01 g, 0.2 mmol) were introduced under nitrogen protection, and then the reaction system was heated to 110 ° C, refluxed and maintained for 8 hours, cooled to room temperature, 100 mL of water was added to quench the reaction and separate the liquids, 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. Finally, the product F-1: 7.45 g (yield: 90%), MS (m / z) (M+): 828 was obtained.

[0083] Example 7

[0084] This example provides a compound F-2, the synthesis route of which is as follows:

[0085]

[0086] Using the same method as Example 6, an equimolar amount of E-2 (4.20 g, 10 mmol) was used to replace E-1, and the final product F-2 was obtained: 6.44 g (yield: 89%), MS (m / z) (M+): 724.

[0087] Example 8

[0088] This embodiment provides a compound F-3, the synthesis route of the compound is as follows:

[0089]

[0090] Using the same method as Example 6, an equimolar amount of E-3 (5.44 g, 10 mmol) was used to replace E-1, and the final product F-3 was obtained: 6.78 g (yield: 80%), MS (m / z) (M+): 848.

[0091] Example 9

[0092] This example provides a compound F-4, the synthesis route of which is as follows:

[0093]

[0094] Using the same method as Example 6, an equimolar amount of E-4 (4.38 g, 10 mmol) was used to replace E-1, and the final product F-4 was obtained: 6.01 g (yield: 81%), MS (m / z) (M+): 742.

[0095] Example 10

[0096] This embodiment provides a compound F-5, the synthesis route of the compound is as follows:

[0097]

[0098] Using the same method as Example 6, an equimolar amount of E-5 (4.87 g, 10 mmol) was used to replace E-1, and the final product F-5 was obtained: 6.96 g (yield: 88%), MS (m / z) (M+): 791.

[0099] Embodiment 11

[0100] This example provides a compound F-6, the synthesis route of which is as follows:

[0101]

[0102] Using the same method as Example 6, an equimolar amount of E-6 (3.61 g, 10 mmol) was used to replace E-1, and the final product F-6 was obtained: 5.53 g (yield: 83%), MS (m / z) (M+): 666.

[0103] Example 12

[0104] This embodiment provides a compound F-7, the synthesis route of the compound is as follows:

[0105]

[0106] Using the same method as Example 6, an equimolar amount of E-7 (5.00 g, 10 mmol) was used to replace E-1, and the final product F-7 was obtained: 6.43 g (yield: 80%), MS (m / z) (M+): 804.

[0107] Example 13

[0108] This embodiment provides a compound F-8, the synthesis route of the compound is as follows:

[0109]

[0110] Using the same method as Example 6, an equimolar amount of E-8 (3.80 g, 10 mmol) was used to replace E-1, and the final product F-8 was obtained: 5.54 g (yield: 81%), MS (m / z) (M+): 684.

[0111] Embodiment 14

[0112] This embodiment provides a compound F-9, the synthesis route of the compound is as follows:

[0113]

[0114] Using the same method as Example 6, an equimolar amount of E-9 (5.24 g, 10 mmol) was used to replace E-1, and the final product F-9 was obtained: 7.45 g (yield: 90%), MS (m / z) (M+): 828.

[0115] Embodiment 15

[0116] This example provides a compound F-10, the synthesis route of which is as follows:

[0117]

[0118] Using the same method as Example 6, an equimolar amount of E-10 (5.14 g, 10 mmol) was used to replace E-1, and the final product F-10 was obtained: 6.79 g (yield: 83%), MS (m / z) (M+): 818.

[0119] Preparation Example of Organic Electroluminescent Material Composition

[0120] Example 16

[0121] This embodiment provides a composition R-1, comprising compound C-1 provided in embodiment 1 and compound F-1 provided in embodiment 6; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-1 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-1.

[0122] Embodiment 17

[0123] This embodiment provides a composition R-2, comprising compound C-1 provided in embodiment 1 and compound F-2 provided in embodiment 7; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-2 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-2.

[0124] Embodiment 18

[0125] This embodiment provides a composition R-3, comprising compound C-1 provided in Example 1 and compound F-3 provided in Example 8; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-3 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-3.

[0126] Embodiment 19

[0127] This embodiment provides a composition R-4, comprising compound C-1 provided in Example 1 and compound F-4 provided in Example 9; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-4 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-4.

[0128] Embodiment 20

[0129] This embodiment provides a composition R-5, comprising compound C-2 provided in Example 2 and compound F-2 provided in Example 7; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-2 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-2 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-5.

[0130] Embodiment 21

[0131] This embodiment provides a composition R-6, comprising compound C-3 provided in Example 3 and compound F-2 provided in Example 7; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-2 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-6.

[0132] Embodiment 22

[0133] This embodiment provides a composition R-7, comprising compound C-3 provided in Example 3 and compound F-3 provided in Example 8; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-3 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-7.

[0134] Embodiment 23

[0135] This embodiment provides a composition R-8, comprising compound C-3 provided in Example 3 and compound F-4 provided in Example 9; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-4 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-8.

[0136] Embodiment 24

[0137] This embodiment provides a composition R-9, comprising compound C-3 provided in Example 3 and compound F-5 provided in Example 10; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-5 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-9.

[0138] Embodiment 25

[0139] This embodiment provides a composition R-10, comprising compound C-4 provided in Example 4 and compound F-3 provided in Example 8; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-4 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-3 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-10.

[0140] Embodiment 26

[0141] This embodiment provides a composition R-11, comprising compound C-5 provided in Example 5 and compound F-2 provided in Example 7; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-5 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-2 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-11.

[0142] Embodiment 27

[0143] This embodiment provides a composition R-12, comprising compound C-5 provided in Example 5 and compound F-3 provided in Example 8; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-5 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-3 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain composition R-12.

[0144] Embodiment 28

[0145] This embodiment provides a composition G-1, comprising compound C-1 provided in embodiment 1 and compound F-6 provided in embodiment 11; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-6 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-1.

[0146] Embodiment 29

[0147] This embodiment provides a composition G-2, comprising compound C-1 provided in embodiment 1 and compound F-7 provided in embodiment 12; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-7 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-2.

[0148] Embodiment 30

[0149] This embodiment provides a composition G-3, comprising compound C-1 provided in Example 1 and compound F-8 provided in Example 13; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-8 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-3.

[0150] Embodiment 31

[0151] This embodiment provides a composition G-4, comprising compound C-1 provided in Example 1 and compound F-10 provided in Example 15; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-10 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-4.

[0152] Embodiment 32

[0153] This embodiment provides a composition G-5, comprising compound C-2 provided in Example 2 and compound F-6 provided in Example 11; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-2 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-6 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-5.

[0154] Embodiment 33

[0155] This embodiment provides a composition G-6, comprising compound C-3 provided in Example 3 and compound F-6 provided in Example 11; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-6 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-6.

[0156] Embodiment 34

[0157] This embodiment provides a composition G-7, comprising compound C-3 provided in Example 3 and compound F-8 provided in Example 13; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-8 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-7.

[0158] Embodiment 35

[0159] This embodiment provides a composition G-8, comprising compound C-3 provided in Example 3 and compound F-9 provided in Example 14; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-9 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-8.

[0160] Embodiment 36

[0161] This embodiment provides a composition G-9, comprising compound C-3 provided in Example 3 and compound F-10 provided in Example 15; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-10 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-9.

[0162] Embodiment 37

[0163] This embodiment provides a composition G-10, comprising compound C-4 provided in Example 4 and compound F-10 provided in Example 15; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-4 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-10 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-10.

[0164] Embodiment 38

[0165] This embodiment provides a composition G-11, comprising compound C-5 provided in Example 5 and compound F-6 provided in Example 11; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-5 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-6 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-11.

[0166] Embodiment 39

[0167] This embodiment provides a composition G-12, comprising compound C-5 provided in Example 5 and compound F-10 provided in Example 15; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-5 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-10 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition G-12.

[0168] Compound Comparative Example

[0169] Comparative Example 1

[0170] This comparative example provides a compound HT-1 that has been tested during the research process, and its specific structural formula is:

[0171]

[0172] Comparative Example 2

[0173] This comparative example provides a compound PM-1 that has been tested during the research process, and its specific structural formula is:

[0174]

[0175] Comparative Example 3

[0176] This comparative example provides a compound PM-2 that has been tested during the research process, and its specific structural formula is:

[0177]

[0178] Comparative Example of Preparation of Organic Electroluminescent Material Composition

[0179] Comparative Example 4

[0180] This embodiment provides a composition DR-1, comprising the compound HT-1 provided in Comparative Example 1 and the compound F-1 provided in Example 6; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-1 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain a composition DR-1.

[0181] Comparative Example 5

[0182] This embodiment provides a composition DR-2, comprising the compound HT-1 provided in Comparative Example 1 and the compound F-2 provided in Example 7; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-2 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain a composition DR-2.

[0183] Comparative Example 6

[0184] This embodiment provides a composition DR-3, comprising the compound HT-1 provided in Comparative Example 1 and the compound F-3 provided in Example 8; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-3 with a thickness of 80 nm to form a luminescence auxiliary layer, to obtain a composition DR-3.

[0185] Comparative Example 7

[0186] This embodiment provides a composition DR-4, comprising the compound HT-1 provided in Comparative Example 1 and the compound F-4 provided in Example 9; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-4 with a thickness of 80 nm to form a luminescence auxiliary layer to obtain a composition DR-4.

[0187] Comparative Example 8

[0188] This embodiment provides a composition DR-5, comprising the compound HT-1 provided in Comparative Example 1 and the compound F-5 provided in Example 10; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-5 with a thickness of 80 nm to form a luminescence auxiliary layer, to obtain a composition DR-5.

[0189] Comparative Example 9

[0190] This embodiment provides a composition DR-6, comprising compound C-1 provided in Example 1 and compound PM-1 provided in Comparative Example 2; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-1 with a thickness of 80 nm to form a luminescence auxiliary layer, to obtain composition DR-6.

[0191] Comparative Example 10

[0192] This embodiment provides a composition DR-7, comprising compound C-2 provided in Example 2 and compound PM-1 provided in Comparative Example 2; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-2 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-1 with a thickness of 80 nm to form a luminescence auxiliary layer, to obtain composition DR-7.

[0193] Comparative Example 11

[0194] This embodiment provides a composition DR-8, comprising compound C-3 provided in Example 3 and compound PM-1 provided in Comparative Example 2; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-1 with a thickness of 80 nm to form a luminescence auxiliary layer, to obtain composition DR-8.

[0195] Comparative Example 12

[0196] This embodiment provides a composition DR-9, comprising compound C-4 provided in Example 4 and compound PM-1 provided in Comparative Example 2; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-4 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-1 with a thickness of 80 nm to form a luminescence auxiliary layer, to obtain a composition DR-9.

[0197] Comparative Example 13

[0198] This embodiment provides a composition DR-10, comprising compound C-5 provided in Example 5 and compound PM-1 provided in Comparative Example 2; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-5 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-1 with a thickness of 80 nm to form a luminescence auxiliary layer, to obtain a composition DR-10.

[0199] Comparative Example 14

[0200] This embodiment provides a composition DG-1, comprising the compound HT-1 provided in Comparative Example 1 and the compound F-6 provided in Example 11; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-6 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain a composition DG-1.

[0201] Comparative Example 15

[0202] This embodiment provides a composition DG-2, comprising the compound HT-1 provided in Comparative Example 1 and the compound F-7 provided in Example 12; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-7 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain a composition DG-2.

[0203] Comparative Example 16

[0204] This embodiment provides a composition DG-3, including the compound HT-1 provided in Comparative Example 1 and the compound F-8 provided in Example 13; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-8 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain a composition DG-3.

[0205] Comparative Example 17

[0206] This embodiment provides a composition DG-4, comprising the compound HT-1 provided in Comparative Example 1 and the compound F-9 provided in Example 14; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-9 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain a composition DG-4.

[0207] Comparative Example 18

[0208] This embodiment provides a composition DG-5, including the compound HT-1 provided in Comparative Example 1 and the compound F-10 provided in Example 15; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit HT-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing F-10 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain a composition DG-5.

[0209] Comparative Example 19

[0210] This embodiment provides a composition DG-6, comprising compound C-1 provided in Example 1 and compound PM-2 provided in Comparative Example 3; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-1 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum deposit PM-2 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition DG-6.

[0211] Comparative Example 20

[0212] This embodiment provides a composition DG-7, comprising compound C-2 provided in Example 2 and compound PM-2 provided in Comparative Example 3; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-2 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-2 with a thickness of 30 nm to form a luminescence auxiliary layer, to obtain composition DG-7.

[0213] Comparative Example 21

[0214] This embodiment provides a composition DG-8, comprising compound C-3 provided in Example 3 and compound PM-2 provided in Comparative Example 3; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-3 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-2 with a thickness of 30 nm to form a luminescence auxiliary layer, to obtain composition DG-8.

[0215] Comparative Example 22

[0216] This embodiment provides a composition DG-9, comprising compound C-4 provided in Example 4 and compound PM-2 provided in Comparative Example 3; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-4 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-2 with a thickness of 30 nm to form a luminescence auxiliary layer to obtain composition DG-9.

[0217] Comparative Example 23

[0218] This embodiment provides a composition DG-10, comprising compound C-5 provided in Example 5 and compound PM-2 provided in Comparative Example 3; the composition is prepared by at least the following steps: using an evaporation preparation method to vacuum deposit C-5 with a thickness of 120 nm to form a hole transport layer, and then on the above-mentioned hole transport layer, vacuum depositing PM-2 with a thickness of 30 nm to form a luminescence auxiliary layer, to obtain composition DG-10.

[0219] Effect example

[0220] The composition provided by the invention has matching energy levels and a small potential barrier, and can significantly reduce the driving voltage of an organic electroluminescent device.

[0221] 1. In order to illustrate that the composite material selected by the present invention has unique advantages in energy level matching, the molecular structure characteristics of the first compounds C-1 to C-5 provided in Examples 1 to 5 and the second compounds F-1 to F-10 provided in Examples 6 to 15 are calculated respectively. The molecular structure is geometrically optimized (Optimization) by Gaussian 09W software based on the density functional theory (DFT) calculation method (the basis set level is set to: b3lyp / 6-31g(d)), and the HOMO energy level and LUMO energy level of the first compounds C-1 to C-5 and the second compounds F-1 to F-10 molecules, and the hole reorganization energy (λh) data are obtained. By subtracting the HOMO energy levels of the first compound and the second compound, the energy level difference ΔHOMO between the composites can be obtained. Generally, the smaller the absolute value of the energy extreme difference ΔHOMO, the smaller the potential barrier between the two layers of materials, and the smaller the driving voltage. The specific calculation results are shown in Table 1:

[0222] 2. In order to illustrate that the composition provided by the present invention has a unique advantage in driving voltage, a semi-device is designed for verification. The structure of the semi-device is: anode (ITO layer) / hole injection layer (thickness 10nm) / hole transport layer (thickness 95nm) / luminescent auxiliary layer (thickness 85nm) / auxiliary layer (thickness 1nm) / cathode (thickness 13nm); the above device is prepared by evaporation, wherein the material of the hole injection layer is a mixture of HTL and p-dopant, and the mass ratio of HTL to p-dopant is 97:3; the material of the hole transport layer is HTL, and HTL is selected from the first compounds C-1 to C-5 provided in Examples 1 to 5; the luminescent auxiliary layer is selected from the second compounds F-1 to F-10 provided in Examples 6 to 15; the material of the auxiliary layer is p-dopant; the cathode is a magnesium-silver mixture, and the mass ratio of magnesium to silver is 2:8; after the above semi-device is made, it is tested at J=@10mA / cm 2 The voltage value V HOD The specific test results are shown in Table 1 and Table 2. The composition in Table 1 is suitable for red organic electroluminescent devices, and the composition in Table 2 is suitable for green organic electroluminescent devices:

[0223] Table 1

[0224]

[0225]

[0226] It can be seen from the results in Table 1 that, compared with the comparative composition, the absolute value of the energy range difference ΔHOMO of the composition provided by the present invention in the red light device is less than 0.02 eV, which is smaller than the absolute value of the energy range difference ΔHOMO of the comparative composition, indicating that the composition provided by the present invention can effectively avoid the accumulation of holes at the interface between the two layers, so that the holes can quickly diffuse to the light-emitting area for recombination, thereby reducing the driving voltage of the organic electroluminescent device.

[0227] Table 2

[0228]

[0229]

[0230] It can be seen from the results in Table 2 that, compared with the comparative composition, the absolute value of the energy range difference ΔHOMO of the composition provided by the present invention in the green light device is less than 0.1 eV, which is smaller than the absolute value of the energy range difference ΔHOMO of the comparative composition, indicating that the composition provided by the present invention can effectively avoid the accumulation of holes at the interface between the two layers, so that the holes can quickly diffuse to the light-emitting area for recombination, thereby reducing the driving voltage of the organic electroluminescent device.

[0231] It can be seen from the results of Table 1 and Table 2 that, compared with the comparative compounds, the first compound provided by the present invention has a larger hole reorganization energy, which can avoid excessive lateral leakage, and the second compound provided by the present invention has shallower LUMO and HOMO values, which can block electron diffusion and increase the threshold voltage; compared with the comparative composition, the absolute value of the energy range difference ΔHOMO of the composition provided by the present invention is smaller, which can effectively avoid the accumulation of holes at the interface between the two layers, so that the holes can quickly diffuse to the light-emitting area for recombination, thereby reducing the driving voltage of the organic electroluminescent device. Since the driving voltage of the organic electroluminescent device is affected by many factors, such as the contact barrier, hole mobility and interface contact conditions of the composition, but the interface contact conditions are difficult to characterize through physical property tests. Therefore, the present invention designs a semi-device experiment to prove that the composition provided by the present invention has unique advantages. From the voltage V of the semi-device test HOD The data show that, compared with the comparative composition, the composition provided by the present invention has a lower voltage V HOD , indicating that the composition provided by the present invention not only has a suitable energy level combination and a small potential barrier, but also has good hole mobility and interface contact, so it can significantly reduce the voltage of the organic electroluminescent device. For example, the energy range difference ΔHOMO of the comparative composition 2, the comparative composition 4, and the comparative composition 5 is exactly the same as that of the composition 16 provided by the present invention, but the voltage V HOD Compared with the composition 16 provided by the present invention, it is significantly increased, indicating that in addition to the barrier factor, the composition of the present invention is more suitable in terms of hole mobility and interface contact. Holes can diffuse uniformly and stably from the hole transport material to the electron blocking material, which can significantly reduce the driving voltage of the organic electroluminescent device.

[0232] Furthermore, compared with comparative example HT-1, the first compounds C-1 to C-5 provided by the present invention have a larger hole reorganization energy λh. The first compound, when combined with the second compound provided by the present invention, can block electron diffusion and increase the threshold voltage, thereby avoiding the occurrence of crosstalk.

[0233] Red light device embodiment 1

[0234] The present embodiment provides a red light organic electroluminescent device, and the preparation method thereof is as follows: first, on the ITO layer (anode) formed on the substrate, a first compound C-1 and p-dopant (the mass ratio of C-1 to p-dopant is 97:3) are vacuum deposited with a thickness of 10 nm to form a hole injection layer; secondly, on the hole injection layer, the first compound C-1 is vacuum deposited with a thickness of 120 nm to form a hole transport layer; secondly, on the hole transport layer, a second compound F-1 is vacuum deposited with a thickness of 80 nm to form a light-emitting auxiliary layer; thirdly, on the light-emitting auxiliary layer, A mixture of RH and RD was vacuum deposited at a thickness of 40 nm to form a light-emitting layer, wherein RH was used as a host, RD was used as a dopant, and the mass ratio of the host to the dopant was 97:3; then, a mixture of ET-01 and Liq (the mass ratio of ET to Liq was 1:1) was vacuum deposited at a thickness of 35 nm on the light-emitting layer to form an electron transport layer; then, LiF was deposited at a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and finally, aluminum (Al) was deposited at a thickness of 150 nm on the electron injection layer to form a cathode, thereby preparing a red light organic electroluminescent device.

[0235] Except for the hole transport layer and the light-emitting auxiliary layer, the molecular structures of the remaining layers are as follows:

[0236]

[0237] The electrode preparation method and the deposition method of each functional layer in this embodiment are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, etc., which will not be described in detail here.

[0238] Red light device embodiment 2-12

[0239] The method is the same as that of the red light device embodiment 1, except that the first compound C-1 and the second compound F-1 are replaced by the materials shown in Table 3 below.

[0240] Table 3

[0241] Serial number First Compound Second compound Red light device embodiment 2 C-1 F-2 Red light device embodiment 3 C-1 F-3 Red light device embodiment 4 C-1 F-4 Red light device embodiment 5 C-2 F-2 Red light device embodiment 6 C-3 F-2 Red light device embodiment 7 C-3 F-3 Red light device embodiment 8 C-3 F-4 Red light device embodiment 9 C-3 F-5 Red light device embodiment 10 C-4 F-3 Red light device embodiment 11 C-5 F-2 Red light device embodiment 12 C-5 F-3

[0242] Red light device comparative examples 1-10

[0243] The method is the same as that of the red light device embodiment 1, except that the first compound C-1 and the second compound F-1 are replaced by the materials shown in Table 4 below.

[0244] Table 4

[0245] Serial number First Compound Second compound Red light device comparative example 1 HT-1 F-1 Red light device comparative example 2 HT-1 F-2 Red light device comparative example 3 HT-1 F-3 Red light device comparative example 4 HT-1 F-4 Red light device comparative example 5 HT-1 F-5 Red light device comparative example 6 C-1 PM-1 Red light device comparative example 7 C-2 PM-1 Red light device comparative example 8 C-3 PM-1 Red light device comparative example 9 C-4 PM-1 Red light device comparative example 10 C-5 PM-1

[0246] Green light device embodiment 1

[0247] The present embodiment provides a green light organic electroluminescent device, and the preparation method thereof is as follows: first, on the ITO layer (anode) formed on the substrate, a first compound C-1 and p-dopant (the mass ratio of C-1 to p-dopant is 97:3) are vacuum deposited with a thickness of 10 nm to form a hole injection layer; secondly, on the hole injection layer, the first compound C-1 is vacuum deposited with a thickness of 120 nm to form a hole transport layer; secondly, on the hole transport layer, a second compound F-6 is vacuum deposited with a thickness of 30 nm to form a light-emitting auxiliary layer; thirdly, on the light-emitting auxiliary layer, a second compound F-6 is vacuum deposited with a thickness of 35 nm. A mixture of GPH, GNH and GD forms a light-emitting layer, wherein GPH and GNH are mixed evenly at a mass ratio of 4:6 as the main body, GD is used as the dopant, and the mass ratio of the main body to the dopant is 95:5; then, on the light-emitting layer, a mixture of ET-01 and Liq (the mass ratio of ET to Liq is 1:1) is vacuum deposited at a thickness of 35nm to form an electron transport layer; then, on the electron transport layer, LiF is deposited at a thickness of 0.2nm to form an electron injection layer, and finally, on the electron injection layer, aluminum (Al) is deposited at a thickness of 150nm to form a cathode, and a green light organic electroluminescent device is prepared. Except for the hole transport layer and the light-emitting auxiliary layer, the molecular structure formulas of the remaining layers are as follows:

[0248]

[0249] Green light device embodiment 2-12

[0250] The method is the same as that of green light device embodiment 1, except that the first compound C-1 and the second compound F-6 are replaced by the materials shown in Table 5 below.

[0251] Table 5

[0252]

[0253]

[0254] Green light device comparison examples 1-10

[0255] The method is the same as that of green light device embodiment 1, except that the first compound C-1 and the second compound F-6 are replaced by the materials shown in Table 6 below.

[0256] Table 6

[0257] Serial number First Compound Second compound Green light device comparative example 1 HT-1 F-6 Green light device comparative example 2 HT-1 F-7 Green light device comparative example 3 HT-1 F-8 Green light device comparative example 4 HT-1 F-9 Green light device comparative example 5 HT-1 F-10 Green light device comparative example 6 C-1 PM-2 Green light device comparison example 7 C-2 PM-2 Green light device comparison example 8 C-3 PM-2 Green light device comparative example 9 C-4 PM-2 Green light device comparative example 10 C-5 PM-2

[0258] Device performance effect example

[0259] The organic electroluminescent devices provided in the red light device embodiments 1 to 12, the red light device comparative examples 1 to 10, the green light device embodiments 1 to 12 and the green light device comparative examples 1 to 10 were tested by a standard method. For this purpose, at J = 10 mA / cm 2 The 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 the device is operated at a current density of 10 mA / cm2, the luminance drops to 80% of its initial value L0 after time LT. The driving voltage (Vop) in Table 7 and Table 8 refers to the device at a current density of 10 mA / cm2. 2 The threshold voltage (Vth) in Table 7 and Table 8 refers to the voltage under the condition of 1cd / m 2 The device life (LT95) in Table 7 and Table 8 refers to the device life at 20mA / cm 2 When working under low temperature, the time required for the luminance to drop to 95% of its initial value L0. The current efficiency (CE) in Table 7 and Table 8 refers to the ratio of the device emission brightness to the injection current density, expressed in cd / A.

[0260] The test instruments and methods for testing the performance of the OLED devices in the above embodiments and comparative examples are as follows:

[0261] Brightness was tested using a spectral scanner PhotoResearch PR-635;

[0262] Current density and lighting voltage: tested using a digital source meter Keithley 2400;

[0263] Life test: Use LT-96ch life test device.

[0264] The performance test results of the above devices are listed in Table 7 and Table 8.

[0265] Table 7 Red light device performance test results

[0266]

[0267]

[0268] Table 8 Green light device performance test results

[0269]

[0270]

[0271] It can be seen from the device performance test results of Tables 7 and 8 above that, compared with the comparative example device, the driving voltage of the organic electroluminescent device provided by the present invention is significantly reduced, and the current efficiency and life are significantly improved. This is due to the energy level matching of the composition provided by the present invention, and the absolute value of the energy range difference ΔHOMO is small, which can effectively avoid the accumulation of holes at the interface of the two layers, so that the holes can quickly diffuse to the light-emitting area for recombination, and the composition provided by the present invention is more suitable in terms of hole mobility and interface contact, and the holes can be uniformly and stably diffused from the hole transport material to the electron blocking material, so that the voltage of the organic electroluminescent device can be significantly reduced. Further, it can be seen from the device performance test results of Tables 7 and 8 above that, compared with the comparative example device, the organic electroluminescent device provided by the present invention has a larger threshold voltage, which can effectively avoid the occurrence of crosstalk, and overcome the defects of the prior art.

[0272] 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. An organic electroluminescent material composition, characterized in that: The composition includes a first compound and a second compound, wherein the layer where the first compound is located is closely attached to the layer where the second compound is located, wherein the first compound is as shown in Chemical Formula I: [Chemical formula I] In the chemical formula I, Ar1 and Ar2 are selected from any one or any combination of substituted or unsubstituted cycloalkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted condensed ring aryl groups having 10 to 30 carbon atoms; The second compound is shown in Chemical Formula II: [Chemical formula II] In the chemical formula II, Ar3 and Ar4 are selected from any one or any combination of substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms, substituted or unsubstituted condensed ring aryl having 10 to 30 carbon atoms, and substituted or unsubstituted condensed ring heteroaryl having 9 to 30 carbon atoms; When Ar1, Ar2, Ar3, Ar4 have substituents, the substituents of Ar1, Ar2, Ar3, Ar4 are independently selected from any one or a combination of deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; two or more adjacent substituents may be bonded to each other through a linking group or a single bond to form an aliphatic ring having 6 to 15 carbon atoms or an aromatic ring having 6 to 30 carbon atoms; Any hydrogen on the first compound and the second compound can be independently replaced by deuterium, alkyl or cycloalkyl.

2. The organic electroluminescent material composition according to claim 1, characterized in that: In the first compound, Ar1 and Ar2 are selected from any one of phenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl and alkylphenyl.

3. The organic electroluminescent material composition according to claim 1, characterized in that: The first compound is selected from any one of the structures shown in the following formula I-1 to formula I-5: The number of R1 and R2 is one or more, and each is independently selected from one or a combination of two of hydrogen, deuterium, adamantyl or phenyl.

4. The organic electroluminescent material composition according to claim 1, characterized in that: The first compound is selected from any one of the following compounds C-1 to C-30:

5. The organic electroluminescent material composition according to claim 1, characterized in that: In the second compound, Ar3 and Ar4 are selected from any one of phenyl, alkylphenyl, 9,9-dimethylfluorenyl, dimethylbenzofluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirobifluorenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, spiro[fluorene-9,9'-oxanthene]yl and spiro[fluorene-9,9'-thioanthene]yl.

6. The organic electroluminescent material composition according to claim 1, characterized in that: The second compound is selected from any one of the structures shown in the following formula II-1 to formula II-15: The number of R3, R4, R5, R6, R7 and R8 is one or more, and each is independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a phenyl group having 6 to 30 carbon atoms or an adamantyl group, or a combination of two of them; wherein two or more adjacent substituents may be bonded to each other through a linking group or a single bond to form any one or a combination of any several of an aliphatic ring having 6 to 15 carbon atoms, an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 5 to 30 carbon atoms, a condensed aromatic group having 10 to 30 carbon atoms, and a condensed heteroaromatic group having 9 to 30 carbon atoms; and X is selected from O or S.

7. The organic electroluminescent material composition according to claim 1, characterized in that: The second compound is selected from any one of the following compounds F-1 to F-40:

8. An organic electroluminescent device, characterized in that: comprising sequentially arranged on a substrate anode; A cathode, disposed face to face with the anode; A light-emitting layer, located between the anode and the cathode; A hole transport layer, located between the anode and the light-emitting layer; and A light-emitting auxiliary layer, located between the light-emitting layer and the hole transport layer; The hole transport layer comprises the first compound according to any one of claims 1 to 4.

9. The organic electroluminescent device according to claim 8, characterized in that: The light-emitting auxiliary layer comprises the second compound according to any one of claims 1 and claims 5 to 7.

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