An organic electroluminescent compound and its preparation method and application

Abstract

The present invention discloses an organic electroluminescent compound. When the organic electroluminescent compound is used as a hole transport material or other organic compound layer of an OLED light-emitting device, the high hole transport rate can reduce the starting voltage of the device, improve the efficiency of the organic electroluminescent device, and greatly extend the service life.

Description

Technical Field

[0001] The present invention relates to the technical field of photoelectric materials, and more particularly to an organic electroluminescent compound and a preparation method and application thereof. Background Art

[0002] With the advent of the information age, people's living standards have changed rapidly, and the requirements for display technology are constantly increasing. Among existing technologies, OLED technology has the advantages of high contrast, flexibility, wide viewing angle, and fast response speed. This makes OLED technology have great potential to replace traditional display technology.

[0003] Typically, OLED light-emitting devices have a stacked structure, consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer stacked in sequence. The hole transport layer (HTL) is responsible for regulating the injection rate and injection amount of holes, and the hole transport material directly affects the efficiency and lifespan of the OLED. In the prior art, commonly used compounds in the hole transport region include copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (MTDATA), and the like.

[0004] However, OLEDs using these materials have problems with quantum efficiency and lifetime. This is because hole-transport materials typically have low highest occupied molecular orbital (HOMO) values. Excitons generated in the light-emitting layer diffuse to the hole-transport layer interface or to the side of the hole-transport layer, ultimately leading to light emission at the interface within the light-emitting layer or charge imbalance within the light-emitting layer. This leads to light emission at the hole-transport layer interface, reducing the color purity and efficiency of the organic electroluminescent device.

[0005] Therefore, how to provide a hole transport material with high luminous efficiency, good lifespan and low voltage is a technical problem that needs to be solved urgently by those skilled in the art. Summary of the Invention

[0006] The purpose of the present invention is to provide an organic electroluminescent compound and a preparation method and application thereof, so as to solve the problems raised in the above background technology.

[0007] In order to achieve the above object, the present invention adopts the following technical solutions:

[0008] An organic electroluminescent compound, characterized in that its general structural formula is shown in Chemical Formula 1:

[0009]

[0010] Among them, a and b are 0 or 1 respectively, and a and b cannot be 0 at the same time;

[0011] R1, R4 and R5 are at any position of the ring, and the number of substituents of R1, R4 and R5 is an integer of 0-4;

[0012] R2 and R3 are at any position of the ring, and the number of substituents of R2 and R3 is an integer of 0-3;

[0013] R1-R5 are each independently selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group;

[0014] or,

[0015] Connected with adjacent substituents to form a monocyclic or polycyclic ring, specifically a C3-C30 alicyclic ring or aromatic ring;

[0016] Ar1-Ar4 are each independently selected from a substituted or unsubstituted C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 3-30 membered heteroaryl group, a substituted or unsubstituted 3-30 membered heteroarylamine group, a substituted or unsubstituted C6-C60 arylamine group, a C1-C30 alkoxy group, and a C6-C60 aryloxy group;

[0017] or,

[0018] Connected with adjacent substituents to form a monocyclic or polycyclic C3-C30 aliphatic ring or a 3- to 30-membered aromatic ring, wherein the carbon atoms thereof may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur;

[0019] L1 and L2 are each independently selected from a linking bond or a substituted or unsubstituted C6-C30 aryl group.

[0020] Preferably, R1-R5 are 0-1 substituents respectively, and R1-R5 are each independently selected from substituted or unsubstituted C1-C30 alkyl or substituted or unsubstituted C6-C30 aryl.

[0021] Preferably, Ar1-Ar4 are each independently selected from a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C15-C26 heteroaryl group or a triarylamine group.

[0022] More preferably, the Ar1-Ar4 are each independently selected from a substituted or unsubstituted C10-C14 aryl group, a substituted or unsubstituted C18-C22 heteroaryl group or a triphenylamino group.

[0023] Preferably, L1 and L2 are each independently selected from benzene or deuterated benzene.

[0024] Furthermore, the organic electroluminescent compound is one of Formula H001 to Formula H129:

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031] The preparation method of the above-mentioned organic electroluminescent compound has the following synthesis path:

[0032] In the above formula, R1 to R5, Ar1 to Ar4, L1 and L2 and a and b are identical to those in the above Chemical Formula 1, and c is 1 or 2; wherein Chemical Formula 2 indicates that L1 and L2 in Chemical Formula 1 are both connecting bonds;

[0033] The specific preparation method is:

[0034] Step 1, preparation of intermediate 1

[0035] Raw material 2 was dissolved in THF, and then ventilated three times, cooled to -78°C, and n-BuLi was added. The reaction was continued for 2 h. Then, raw material 1 was added under N2 protection, and the temperature was raised to 25°C and stirred for 10 h to prepare intermediate 1.

[0036] Step 2, preparation of intermediate 2

[0037] Add intermediate 1 to a reaction flask, add glacial acetic acid, raise the temperature to 80°C, and dropwise add concentrated sulfuric acid to prepare intermediate 2;

[0038] Step 3, preparation of chemical formula 1

[0039] Add intermediate 2 and raw material 3 to a mixed solution of toluene, ethanol and water, then ventilate three times, add palladium catalyst and potassium carbonate under nitrogen protection, stir evenly, heat to 95°C, and react for 10 hours to prepare chemical formula 1;

[0040] or,

[0041] Preparation of Chemical Formula 2

[0042] Intermediate 2 and raw material 4 were added to a toluene solution, followed by venting three times. Palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide were added under nitrogen protection, stirred evenly, heated to 110° C., and reacted for 8 h to prepare Chemical Formula 2.

[0043] Preferably, the above step 1 specifically includes:

[0044] Raw material 2 was dissolved in THF, followed by venting three times, cooling to -70 to -80°C, slowly adding n-BuLi, and reacting for 1-3 hours. Raw material 1 was added under N2 protection, slowly warming to 20-30°C, and stirring for 8-10 hours. Distilled water was then slowly added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM; the extracted organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator; the solid was precipitated with DCM and PE (1:6) to obtain intermediate 1.

[0045] Preferably, the above step 2 specifically includes:

[0046] Add intermediate 1 to a reaction flask, add 10 times the volume of glacial acetic acid and heat to 80°C, slowly add concentrated sulfuric acid (1 volume) dropwise until the reaction is complete, then add distilled water (20 times the volume of concentrated sulfuric acid), completely precipitate the solid, filter and dry to obtain intermediate 2.

[0047] Preferably, the above step 3 specifically includes:

[0048] Preparation of Chemical Formula 1

[0049] Intermediate 2 and raw material 3 were added to a mixed solution of toluene, ethanol and water, followed by venting three times. Palladium catalyst and potassium carbonate were added under nitrogen protection, stirred evenly, heated to 95° C., reacted for 10 hours, and then the mixture was extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography to obtain the compound shown in Chemical Formula 1.

[0050] or,

[0051] Preparation of Chemical Formula 2

[0052] Intermediate 2 and raw material 4 were added to a toluene solution, followed by venting three times. Palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide were added under nitrogen protection, stirred evenly, heated to 110° C., reacted for 10 hours, and then the mixture was extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography to obtain the compound shown in Chemical Formula 2.

[0053] Another object of the present invention is to provide an organic electroluminescent device containing the above-mentioned organic electroluminescent compound, comprising: a first electrode, a second electrode, and one or more organic compound layers disposed between the first electrode and the second electrode;

[0054] The organic compound layer includes a hole transport layer, and the hole transport layer includes the above-mentioned organic electroluminescent compound.

[0055] The hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light emitting layer, and has high hole mobility.

[0056] Preferably, it further comprises one or more layers of a hole injection layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0057] Preferably, the first electrode serves as an anode, which preferably comprises a material with a high work function, such as indium tin oxide (ITO) or indium zinc oxide (IZO). Since the lifetime of the device of the present invention is shortened in the presence of water and / or air, the device is appropriately structured (depending on the application), provided with contacts, and finally sealed.

[0058] The electron blocking layer may be provided between the hole transport layer and the light emitting layer. As the electron blocking layer, materials known in the art, such as arylamine-based organic materials, may be used.

[0059] The material of the light emitting layer is a material that can emit visible light by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the received holes and electrons.

[0060] The light-emitting layer comprises a host material and a dopant material;

[0061] The mass ratio of the main material to the doping material is 90-99.5:0.5-10;

[0062] The host material includes a fluorescent host and a phosphorescent host;

[0063] Doping materials include fluorescent doping and phosphorescent doping;

[0064] The hole blocking layer material may be any compound known in the art that has a hole blocking effect, for example, phenanthroline derivatives such as bathocuproine (BCP), oxazole derivatives, triazole derivatives, triazine derivatives, etc., but is not limited thereto.

[0065] The electron transport layer can promote electron transport and can use compounds known in the prior art that have electron transport properties, such as Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes, etc.

[0066] The electron injection layer facilitates electron injection. It has the ability to transport electrons, preventing excitons generated in the light-emitting layer from migrating to the hole injection layer. Electron injection materials used in the present invention include, but are not limited to, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and their derivatives, metal complexes, and nitrogen-containing five-membered ring derivatives.

[0067] The second electrode, serving as the cathode, is preferably made of a material with a small work function to facilitate electron injection into the organic material layer, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof.

[0068] It can be seen from the above technical solutions that compared with the prior art, the present invention has the following beneficial effects:

[0069] The π conjugation effect in organic electroluminescent compounds gives them strong hole transport capabilities. When these organic electroluminescent compounds are used as hole transport materials or other organic compound layers in OLED light-emitting devices, the high hole transport rate can reduce the starting voltage of the device, improve the efficiency of the organic electroluminescent device, and significantly extend its service life. DETAILED DESCRIPTION

[0070] The following is a clear and complete description of the technical solutions in the embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making any creative efforts are within the scope of protection of the present invention.

[0071] Example 1

[0072] A method for preparing an organic electroluminescent compound, using the above-mentioned synthesis route, comprises the following steps:

[0073] Add raw material 2 (44.6 mmol) and 100 ml of THF to the reaction vessel, ventilate 3 times and cool to -78 ° C. Under a nitrogen atmosphere, add 2.5 mol / L n-BuLi (17.8 ml, 44.6 mmol) and stir for 2 h. Add raw material 1 (37 mmol) and raise the temperature to 25 ° C. Stir for 10 h. The reaction is complete. Distilled water is then added to the reaction solution to quench the reaction, and the reaction solution is extracted with DCM. The extracted organic layer is then dried over magnesium sulfate, and the solvent is removed using a rotary evaporator. The solid is precipitated with DCM and PE (1:6) to obtain intermediate 1 (12.8 g, yield 75.7%, MW: 457.91).

[0074] Intermediate 1 (26.2 mmol) was added to a reaction flask, 240 ml of glacial acetic acid was added, the temperature was raised to 80°C, and 12 ml of concentrated sulfuric acid was added dropwise. The reaction was completed after the addition was completed. Then 240 ml of distilled water was added, and a solid precipitated. The solid was dried to obtain intermediate 2 (8.9 g, yield 77.23%, MW: 439.88).

[0075] Intermediate 2 (18.1 mmol) and raw material 3 (21.8 mmol) were added to 300 ml of toluene solution, followed by venting three times. Palladium catalyst (0.181 mmol), tri-tert-butylphosphine (0.905 mmol) and sodium tert-butoxide (36.2 mmol) were added under nitrogen protection, stirred evenly, heated to 110° C., reacted for 10 h, and then extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography (the volume ratio of DCM to PE was 1:11) to obtain an organic electrogenic compound, see formula H048 (9.88 g, yield 71.3%, MW: 764.97), the reaction scheme is as follows:

[0076]

[0077] Example 2

[0078] A method for preparing an organic electroluminescent compound, using the above-mentioned synthesis route, comprises the following steps:

[0079] Add raw material 2 (44.6 mmol) and 100 ml of THF to the reaction vessel, ventilate 3 times and cool to -78 ° C. Under a nitrogen atmosphere, add 2.5 mol / L n-BuLi (17.8 ml, 44.6 mmol) and stir for 2 h. Add raw material 1 (37 mmol) and raise the temperature to 25 ° C. Stir for 10 h. The reaction is complete. Distilled water is then added to the reaction solution to quench the reaction, and the reaction solution is extracted with DCM. The extracted organic layer is then dried over magnesium sulfate, and the solvent is removed using a rotary evaporator. The solid is precipitated with DCM and PE (1:6) to obtain intermediate 1 (12.4 g, 73.4% yield, MW: 457.92).

[0080] Intermediate 1 (26.2 mmol) was added to a reaction flask, 240 ml of glacial acetic acid was added, the temperature was raised to 80°C, and 12 ml of concentrated sulfuric acid was added dropwise. The reaction was completed after the addition was completed. Then 240 ml of distilled water was added, and a solid precipitated. The solid was dried to obtain intermediate 2 (8.4 g, yield 72.8%, MW: 439.89).

[0081] Intermediate 2 (18.1 mmol) and raw material 3 (21.8 mmol) were added to a mixed solution of toluene (180 ml), ethanol (60 ml), and water (60 ml), followed by venting three times. Palladium catalyst (0.181 mmol) and potassium carbonate (54.3 mmol) were added and stirred evenly. The temperature was raised to 100° C. and the reaction was carried out for 10 h. The mixture was then extracted with dichloromethane and water. The extracted organic layer was then dried over sodium sulfate, and the solvent was removed using a rotary evaporator. The remaining substance was purified by column chromatography (the volume ratio of DCM to PE was 1:11) to obtain an organic electrogenic compound, formula H033 (10.1 g, yield 69.8%, MW: 801.05). The reaction scheme is as follows:

[0082]

[0083] Example 3

[0084] A method for preparing an organic electroluminescent compound, using the above-mentioned synthesis route, comprises the following steps:

[0085] Add raw material 2 (44.6 mmol) and 100 ml of THF to the reaction vessel, ventilate 3 times and cool to -78 ° C. Under a nitrogen atmosphere, add 2.5 mol / L n-BuLi (17.8 ml, 44.6 mmol) and stir for 2 h. Add raw material 1 (37 mmol) and raise the temperature to 25 ° C. Stir for 10 h. The reaction is complete. Distilled water is then added to the reaction solution to quench the reaction, and the reaction solution is extracted with DCM. The extracted organic layer is then dried over magnesium sulfate, and the solvent is removed using a rotary evaporator. The solid is precipitated with DCM and PE (1:6) to obtain intermediate 1 (14.3 g, 72.4% yield, MW: 536.11).

[0086] Intermediate 1 (26.2 mmol) was added to a reaction flask, 240 ml of glacial acetic acid was added, the temperature was raised to 80°C, and 12 ml of concentrated sulfuric acid was added dropwise. The reaction was completed after the addition was completed. Then 240 ml of distilled water was added, and a solid precipitated. The solid was dried to obtain intermediate 2 (10.4 g, yield 76.5%, MW: 518.10).

[0087] Intermediate 2 (18.1 mmol) and raw material 3 (21.8 mmol) were added to 300 ml of toluene solution, followed by venting three times. Palladium catalyst (0.181 mmol), tri-tert-butylphosphine (0.905 mmol) and sodium tert-butoxide (36.2 mmol) were added under nitrogen protection, stirred evenly, heated to 110° C., reacted for 10 h, and then extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography (the volume ratio of DCM to PE was 1:11) to obtain an organic electrogenic compound, see formula H067 (11.2 g, yield 70.1%, MW: 883.18), the reaction scheme is as follows:

[0088]

[0089] Example 4

[0090] A method for preparing an organic electroluminescent compound, using the above-mentioned synthesis route, comprises the following steps:

[0091] Add raw material 2 (44.6 mmol) and 100 ml of THF to the reaction vessel, ventilate 3 times and cool to -78 ° C. Under a nitrogen atmosphere, add 2.5 mol / L n-BuLi (17.8 ml, 44.6 mmol) and stir for 2 h. Add raw material 1 (37 mmol) and raise the temperature to 25 ° C. Stir for 10 h. The reaction is complete. Distilled water is then added to the reaction solution to quench the reaction, and the reaction solution is extracted with DCM. The extracted organic layer is then dried over magnesium sulfate, and the solvent is removed using a rotary evaporator. The solid is precipitated with DCM and PE (1:6) to obtain intermediate 1 (14.2 g, 75.5% yield, MW: 508.05).

[0092] Intermediate 1 (26.2 mmol) was added to a reaction flask, 240 ml of glacial acetic acid was added, the temperature was raised to 80°C, and 12 ml of concentrated sulfuric acid was added dropwise. The reaction was completed after the addition was completed. Then 240 ml of distilled water was added, and a solid precipitated. The solid was dried to obtain intermediate 2 (9.8 g, yield 76.1%, MW: 490.08).

[0093] Intermediate 2 (18.1 mmol) and raw material 3 (21.8 mmol) were added to 300 ml of toluene solution, followed by venting three times. Palladium catalyst (0.181 mmol), tri-tert-butylphosphine (0.905 mmol) and sodium tert-butoxide (36.2 mmol) were added under nitrogen protection, stirred evenly, heated to 110° C., reacted for 10 h, and then extracted with dichloromethane and water; the extracted organic layer was then dried over sodium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography (volume ratio of DCM to PE: 1:11) to obtain an organic electrogenic compound, see formula H093 (10.7 g, yield: 71.1%, MW: 829.08), and the reaction scheme is as follows:

[0094]

[0095] Example 5-20

[0096] Compounds 2, 6, 11, 18, 26, 47, 60, 70, 76, 82, 85, 92, 95, 100, 105, and 123 were synthesized by referring to the synthesis method of Example 1. The mass spectra, molecular formulas, and yields of Examples 5-20 are shown in Table 1 below. In addition, it should be noted that other compounds of the present application can be obtained by referring to the synthesis methods of the above-listed examples.

[0097] Table 1

[0098]

[0099]

[0100] Application Example 1

[0101] An organic electroluminescent device is prepared by the following method:

[0102] a. ITO anode: the coating thickness is The ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate was cleaned twice in distilled water, ultrasonically washed for 30 minutes, and then repeatedly cleaned twice with distilled water, ultrasonically washed for 10 minutes. After washing, it was ultrasonically washed with methanol, acetone, and isopropanol in sequence (5 minutes each time), dried, and then transferred to a plasma cleaning machine for washing for 5 minutes. It was then sent to a vapor deposition machine, and the substrate was used as the anode, and other functional layers were evaporated on it in sequence.

[0103] b. HIL (hole injection layer): The hole injection layer material HT (the compound provided in Example 1 of the present invention) and P-dopant were vacuum evaporated at a deposition rate of 98:2, and the thickness was 10 nm;

[0104] c. HTL (hole transport layer): The compound provided in Example 1 of the present invention is vacuum evaporated on the hole injection layer to form a hole transport layer with a thickness of 120 nm at a deposition rate of ;

[0105] d. EML (Emitting Layer): Then on the hole transport layer, The host material and dopant material were vacuum-deposited to a thickness of 25 nm as the light-emitting layer. The chemical formulas of the host and dopant are shown below. The evaporation rate ratio of the host to dopant was 97:3.

[0106] e. ETL (Electron Transport Layer): ET and Liq were vacuum-deposited at a thickness of 35 nm as an electron transport layer. The chemical formula of ET is shown below. The ET and Liq deposition rate ratio was 50:50.

[0107] f. EIL (electron injection layer): The evaporation rate is 1.0 nm, and a Yb film layer is evaporated to form an electron injection layer.

[0108] g. Cathode: The evaporation rate ratio is 1:9, and 18nm of magnesium and silver are evaporated, and the evaporation rate ratio is 1:9 to obtain an OLED device.

[0109] h. Light extraction layer: At a deposition rate of , a CPL with a thickness of 70 nm was vacuum-deposited on the cathode as a light extraction layer.

[0110] i. Encapsulate the vapor-deposited substrate. First, use the glue coating equipment to coat the cleaned cover with UV glue. Then move the coated cover to the pressing section, place the vapor-deposited substrate on the upper end of the cover, and finally, bond the substrate and cover together using the bonding equipment, while simultaneously curing the UV glue with light.

[0111]

[0112] Comparative Example 1

[0113] According to the method of Application Example 1, the material of the hole transport layer is replaced by the compound in Application Example 1 with chemical A. The structural formula of compound A is as follows:

[0114]

[0115] Comparative Example 2

[0116] According to the method of Application Example 1, the material of the hole transport layer is replaced by the compound in Application Example 1 with chemical B. The structural formula of compound B is as follows:

[0117]

[0118] The driving voltage, luminous efficiency, BI value and life of the organic electroluminescent devices obtained from the above device examples and device comparison examples were characterized at a brightness of 1000 (nits). The test results are shown in Table 2 below:

[0119] Table 2

[0120]

[0121]

[0122] As can be seen from Table 2, the π-conjugation effect in the organic electroluminescent compound proposed in the present invention gives it a strong hole transport ability. By introducing aromatic amine side chains, the overall spatial structure of the compound is made radial, which increases the distance between molecules, thereby reducing the cohesive force between molecules and reducing the possibility of crystallization. When the organic electroluminescent compound is used as a hole transport material or other organic compound layer in an OLED light-emitting device, the high hole transport rate can reduce the starting voltage of the device, improve the efficiency of the organic electroluminescent device, and significantly extend the service life.

[0123] The various embodiments in this specification are described in a progressive manner, with each embodiment focusing on the differences from other embodiments. Reference can be made to the common and similar parts between the various embodiments. For the devices disclosed in the embodiments, since they correspond to the methods disclosed in the embodiments, the description is relatively simple, and the relevant parts can be referred to the method description.

[0124] The above description of the disclosed embodiments is intended to enable one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be readily apparent to one skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention is not limited to the embodiments shown herein but is intended to conform to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. An organic electroluminescent compound, characterized in that Any one selected from Formula H001 to Formula H129:

2. A hole transport layer in an organic electroluminescent device, characterized in that: The hole transport layer in the organic electroluminescent device comprises the organic electroluminescent compound according to claim 1 .

3. An organic electroluminescent device, characterized in that: The method comprises the hole transport layer according to claim 2.

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