An organic compound, an organic light-emitting material, and an organic electroluminescent device

Abstract

The present invention provides an organic compound, an organic light-emitting material and an organic electroluminescent device. The organic compound has a structure shown by Chemical Formula I. The organic compound of the present invention can enable the organic light-emitting device to have a lower driving voltage, a higher current efficiency and a longer lifespan.

Description

Technical Field

[0001] The present invention belongs to the technical field of electroluminescent materials, and relates to an organic compound, an organic light-emitting material, and an organic electroluminescent device. Background Art

[0002] As early as the 1960s, the phenomenon of organic electroluminescence was discovered. In 1963, Pope et al. from New York University in the United States found in the study of organic aromatic anthracene crystals that when a voltage of several hundred volts was applied to the anthracene crystals, a weak blue light emission phenomenon could be observed in the crystals, thus opening up the road for the research and development of optoelectronic materials. However, due to the too high driving voltage required and low luminous efficiency, etc., this discovery did not attract much attention. In 1987, Dr. Ching W. Tang reported the electroluminescent diode technology based on organic light-emitting materials, mainly using the vacuum evaporation method to prepare a bilayer device with a transport layer and a light-emitting layer. The quantum efficiency was increased to 1%, and the brightness of 1000 cd / m 2 could be achieved at a working voltage of less than 10V, which attracted wide attention from scientific enthusiasts around the world and promoted the pace of the organic electroluminescence technology towards the practical stage.

[0003] With the continuous development of the organic electroluminescent diode technology, organic light-emitting devices (Organic Light-Emitting Diodes, abbreviated as OLEDs) have been widely used in the fields of information display and lighting due to their advantages such as self-luminescence, wide viewing angle, light and thin, low driving voltage, fast response speed, and bendable and foldable. The light-emitting layer, as an important part of OLEDs, is composed of three organic electroluminescent materials of red, green, and blue. Among these light-emitting materials, organic materials can be used as materials required for lighting and are also particularly important materials in display technology. Although organic electroluminescent materials were discovered very early, the various performance aspects of the existing publicly disclosed organic materials have not fully met the requirements of large-scale production and applications. It is difficult to provide a high luminous efficiency at a low voltage. Therefore, finding high-performance and stable organic electroluminescent materials has become the key and difficult problem for major breakthroughs in the field of OLEDs. Summary of the Invention

[0004] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide an organic compound, an organic light-emitting material, and an organic electroluminescent device. The organic compound of the present invention, as an organic light-emitting material, can have the advantages of high luminous efficiency, high color saturation, good film-forming property, and good thermal stability, etc., and can enable the organic light-emitting device to have a low driving voltage, a high current efficiency, and a long lifespan.

[0005] To achieve this purpose, the present invention adopts the following technical solutions:

[0006] On the one hand, the present invention provides an organic compound having a structure represented by Chemical Formula I:

[0007]

[0008] Wherein, A1, A2, A3, B1 and B2 are the same as or different from each other, and are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted pyridyl group; or combine with adjacent substituents to form a substituted or unsubstituted aromatic ring or aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms and containing one or more of N, O and S as heteroatoms;

[0009] R1, R2, R3, R4 and R5 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 60 carbon atoms, a substituted or unsubstituted amino group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combine with adjacent substituents to form a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms;

[0010] n1 to n5 are each an integer from 0 to 5 (for example, 0, 1, 2, 3, 4 or 5).

[0011] In the present invention, "substituted" means substituted by at least one substituent selected from: hydrogen, deuterium, a nitrile group, a halogen group, a C1-C20 alkyl group, a C6-C30 aryl group, a C6-C30 heteroaryl group, and the heteroatoms in the heteroaryl group are selected from oxygen, nitrogen, sulfur or silicon.

[0012] In the present invention, A1, A2 and A3 are represented by a dashed circle, and the arc of the circle intersects with the connected ring, indicating that A1, A2 and A3 are fused with the connected ring respectively; B1 and B2 are represented by a dashed circle and are connected to the N atom by a single bond.

[0013] In the present invention, the range of the number of carbon atoms in the defined group represents any integer within the defined range. For example, when the number of carbon atoms is from 3 to 30, it means the number of carbon atoms can be 3, 4, 5, 8, 10, 13, 16, 19, 20, 22, 25, 28, or 30, etc.; when the number of carbon atoms is from 1 to 20, it means the number of carbon atoms can be 1, 3, 5, 8, 10, 12, 14, 16, 18, or 20, etc., and so on.

[0014] Preferably, A1 and A2 are selected from phenyl, benzofuranyl, or benzothiophenyl.

[0015] Preferably, A3 is selected from benzofuranyl or benzothiophenyl.

[0016] Preferably, B1 and B2 are selected from phenyl.

[0017] Preferably, R1, R2, R3, R4, and R5 are selected from fluorine, methyl, ethyl, biphenyl, terphenyl, isopropyl, tert-butyl, phenyl, cyclohexane, cyclopentane, adamantyl, cyano, trifluoromethyl, pentafluorophenyl, trimethylsilyl, triphenylsilyl, naphthyl, dibenzofuranyl, dimethylfluorenyl, carbazolyl, or phenyl in which all hydrogen atoms on the benzene ring are replaced by deuterium.

[0018] Preferably, the organic compound has a structure shown in any one of Chemical Formulas 1-1 to 1-16:

[0019]

[0020]

[0021]

[0022] In the above Chemical Formulas 1-1 to 1-16, R1-R5 and n1-n5 have the same defined range as in Chemical Formula I. As a preferred technical solution, the organic compound of the present invention is any one of the following compounds L001 to L420:

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] On the other hand, the present invention provides a method for preparing the organic compound as described above, and the synthetic reaction route is as follows:

[0046]

[0047] R1-R5, A1-A3, B1, B2 and n1-n5 are the same as those defined in Chemical Formula 1.

[0048] X1, X2, X3 are selected from halogens, and the halogens are Cl, Br or I.

[0049] The synthetic route of the organic compound provided by the present invention is short, the process is simple, the raw materials are easy to obtain, the cost is low, and it is suitable for industrial production.

[0050] On the other hand, the present invention provides an organic optoelectronic material, and the organic optoelectronic material includes any one or a combination of at least two of the organic compounds as described above.

[0051] On the other hand, the present invention provides an organic electroluminescent device, which includes a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode. The organic thin film layer includes the organic compound having the chemical formula I as described above.

[0052] Preferably, the organic thin film layer includes a light-emitting layer, and the light-emitting layer contains a host material and a doping material. The doping material includes the organic compound having the chemical formula I as described above.

[0053] Preferably, the percentage of the doping material in the total material of the light-emitting layer is 0.5 - 10%, such as 0.5%, 0.8%, 1%, 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9% or 10%.

[0054] Preferably, the organic thin film layer further includes any one layer or a combination of at least two layers selected from a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.

[0055] The first electrode serves as an anode, and the anode preferably contains a material having a high work function. For example, indium tin oxide (ITO) or indium zinc oxide (IZO). Since the lifetime of the device of the present invention will be shortened in the presence of water and / or air, the device is appropriately (depending on the application) structured, provided with contacts, and finally sealed.

[0056] 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 a high hole mobility. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both a conjugated part and a non-conjugated part, etc., but are not limited thereto.

[0057] An electron blocking layer can be disposed between the hole transport layer and the light-emitting layer. As the electron blocking layer, materials known in the art can be used, such as arylamine-based organic materials.

[0058] 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.

[0059] The light-emitting layer contains a host material and a doping material, and the mass ratio of the host material to the doping material is (90 - 99.5):(0.5 - 10). In the present invention, the doping material contains the organic compound having the chemical formula I described in the present invention. The host material is not particularly limited, and examples of the material include: carbazole group derivatives, aryl silicon derivatives, aromatic derivatives, metal complex derivatives. The aromatic derivatives are derivatives of anthracene, pyrene, naphthalene, phenanthrene, fluorene, etc.

[0060] For the hole blocking layer material, compounds with hole blocking effects known in the prior art can be used. For example, phenanthroline derivatives such as bathocuproine (BCP), oxazole derivatives, triazole derivatives, triazine derivatives, etc., but not limited thereto.

[0061] The electron transport layer can play a role in promoting electron transport. Compounds with electron transport effects known in the prior art can be used. For example, Al complex of 8-hydroxyquinoline; complex containing Alq3; organic radical compounds; metal complexes of hydroxyflavone, etc.

[0062] The electron injection layer can play a role in promoting electron injection. It has the ability to transport electrons and prevent excitons generated in the light-emitting layer from migrating to the hole injection layer. The electron injection materials used in the present invention include fluorenone, anthraquinone dimethane, biphenyl, quinone, thiopyran dioxide, oxazole, dioxazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, etc. and their derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, etc., but not limited thereto.

[0063] The second electrode serves as the cathode and usually preferably uses materials with a small work function to enable smooth electron injection into the organic material layer. For example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys.

[0064] Compared with the prior art, the present invention has the following beneficial effects:

[0065] Due to the specific boron-nitrogen compound structure, the organic compound of the present invention can enable the organic light-emitting device to have a lower driving voltage, higher current efficiency, and longer lifespan after being used in the organic light-emitting device. Specific Embodiments

[0066] The technical solution of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be regarded as specific limitations to the present invention.

[0067] Example 1

[0068] This example provides an organic light-emitting compound with a chemical structural formula of Formula L001. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0069]

[0070] Its specific preparation method includes the following steps:

[0071] Step 1: Heat a flask containing A-001 (10.46 g, 50 mmol), B-001 (16.6 g, 50 mmol), Pd-132 (0.35 g, 0.5 mmol), sodium tert-butoxide (9.6, 100 mmol) and toluene (90 mL) to 120 °C and stir the reaction for 8 hours. Cool the reaction solution to room temperature, add water and ethyl acetate to separate the liquid layers. Distill off the solvent under reduced pressure and purify it by silica gel column chromatography (eluent: hexane / ethyl acetate = 50% / 50% (v / v)) to obtain intermediate C-001 (18.34 g). Measure the mass spectrum of the obtained solid, and as a result, MS(EI) m / z: [M]+445.24.

[0072] Step 2: Heat a flask containing C-001 (17.77 g, 40 mmol), D-002 (6.78 g, 40 mmol), Pd-132 (0.28 g, 0.04 mmol), sodium tert-butoxide (7.68 g, 80 mmol) and toluene (90 mL) to 120 °C and stir for 8 hours. Cool the reaction solution to room temperature, add water and ethyl acetate to separate the liquid layers. Then distill off the solvent under reduced pressure and purify it by silica gel column chromatography (eluent: hexane / ethyl acetate = 50% / 50% (v / v)) to obtain intermediate E-001 (19.6 g). Measure the mass spectrum of the obtained solid, and as a result, MS(EI) m / z: [M] + 578.34.

[0073] Step 3: Add a 1.3 M solution of tert-butyllithium in pentane (78.16 mL) to a flask containing intermediate E-001 (19.6 g, 33.9 mmol) and tert-butylbenzene (150 mL) at -30 °C under a nitrogen atmosphere. After completion of the addition, raise the temperature to 70 °C and stir the mixture for 1 hour, then distill off the pentane. After cooling to -30 °C, add boron tribromide (25.38 g, 101.61 mmol) thereto, and raise the mixture to room temperature and stir for 1 hour. Thereafter, cool the mixture again to 0 °C, add N,N-diisopropylethylamine (13.13 g, 101.61 mmol) thereto and stir at room temperature, then stir at 100 °C for 3 hours. Cool the reaction solution to 0 °C, and add saturated potassium acetate solution and ethyl acetate to separate the liquid layers. Then distill off the solvent under reduced pressure. Purify it by silica gel column chromatography (eluent: hexane / dichloromethane = 40 / 1 (v / v)) to obtain compound L002 (8.6 g). Measure the mass spectrum of the obtained solid, and as a result, MS(EI) m / z: [M] + 551.3.

[0074] 11H NMR (500 MHz, CDCl3) δ 7.92 (dd, J = 7.5, 1.6 Hz, 1H), 7.76–7.71 (m, 1H), 7.58 (ddd, J = 7.5, 3.8, 1.6 Hz, 2H), 7.44 (td, J = 7.4, 1.6 Hz, 1H), 7.41–7.34 (m, 1H), 7.37–7.27 (m, 7H), 7.30–7.22 (m, 2H), 7.18 (dd, J = 7.5, 1.6 Hz, 1H), 7.14–7.02 (m, 7H).

[0075] Example 2

[0076] This example provides an organic light-emitting compound with a chemical structural formula of Formula L022. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0077]

[0078] Compound L022 (15.9 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-022 (24.3 g) and compound D-001 was changed to intermediate D-022 (9.8 g). The mass spectrum of the obtained solid was measured, and as a result, MS (EI) m / z: [M] + 663.8.

[0079] 1 1H NMR (500 MHz, CDCl3) δ 7.92 (dd, J = 7.9, 1.6 Hz, 1H), 7.73 (dd, J = 7.7, 1.6 Hz, 1H), 7.58 (dd, J = 7.5, 1.6 Hz, 1H), 7.52–7.41 (m, 2H), 7.38–7.31 (m, 2H), 7.34–7.28 (m, 2H), 7.31–7.21 (m, 5H), 7.15–7.04 (m, 5H), 7.03–6.95 (m, 2H), 1.35 (s, 9H), 1.29 (s, 9H).

[0080] Example 3

[0081] This example provides an organic light-emitting compound with a chemical structural formula of Formula L043. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0082]

[0083] Compound L043 (17.6 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-043 (22.6 g) and compound D-001 was changed to intermediate D-043 (7.6 g). The mass spectrum of the obtained solid was measured, and as a result, MS (EI) m / z: [M] + 719.5

[0084] 1 H NMR (500 MHz, CDCl3) δ 7.90–7.89 (dd, 1H), 7.64–7.63 (s, 1H), 7.58–7.56 (dd, 1H), 7.5–7.49 (dd, 1H), 7.52–7.41 (m, 1H), 7.39–7.21 (m, 9H), 7.12–7.04 (m, 4H), 6.97 (s, 2H), 1.36 (s, 18H), 1.30 (s, 9H).

[0085] Example 4

[0086] This example provides an organic light-emitting compound with a chemical structural formula of formula L063. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0087]

[0088] Compound L063 (13.2 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-063 (22.6 g) and compound D-001 was changed to intermediate D-063 (8.4 g). The mass spectrum of the obtained solid was measured, and as a result, MS (EI) m / z: [M] + 755.6

[0089] 1 H NMR (500 MHz, CDCl3) δ 8.03–8.03 (s, 1H), 7.97–7.87 (m, 2H), 7.80 (dd, J = 7.5, 1.5 Hz, 1H), 7.60–7.53 (m, 3H), 7.48–7.37 (m, 4H), 7.40–7.34 (m, 6H), 7.33–7.22 (m, 4H), 7.12–7.03 (m, 3H), 7.01–6.95 (m, 1H), 1.36 (s, 9H), 1.30 (s, 9H).

[0090] Example 5

[0091] This example provides an organic light-emitting compound with a chemical structural formula of Formula L069. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0092]

[0093] Compound L069 (16.4 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-069 (22.1 g) and compound D-001 was changed to intermediate D-069 (7.8 g). The mass spectrum of the obtained solid was measured, and as a result, MS(EI) m / z: [M] + 739.5.

[0094] 1 H NMR (500 MHz, CDCl3) δ 7.90 (dd, J = 7.3, 1.6 Hz, 1H), 7.67 (d, J = 7.4 Hz, 1H), 7.57 (dd, J = 7.3, 1.6 Hz, 1H), 7.55–7.49 (m, 3H), 7.45 (td, J = 7.5, 1.6 Hz, 1H), 7.42–7.37 (m, 1H), 7.41–7.32 (m, 3H), 7.36–7.26 (m, 3H), 7.26–7.20 (m, 2H), 7.20–7.15 (m, 2H), 7.17–7.12 (m, 1H), 7.12–7.05 (m, 5H), 6.97 (s, 1H), 2.72–2.62 (m, 1H), 2.57 (hept, J = 6.5 Hz, 1H), 1.64–1.46 (m, 4H), 1.19 (dd, J = 6.8, 2.7 Hz, 6H), 0.80 (td, J = 8.0, 3.4 Hz, 6H).

[0095] Example 6

[0096] This example provides an organic light-emitting compound with a chemical structural formula of Formula L078. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0097]

[0098] Compound L078 (12.3 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-078 (18.1 g) and compound D-001 was changed to intermediate D-078 (7.7 g). The mass spectrum of the obtained solid was measured, and as a result, MS(EI) m / z: [M] + 700.6.

[0099] 1 1H NMR (500 MHz, CDCl3) δ 7.91 (dd, J = 7.6, 1.5 Hz, 1H), 7.82 (d, J = 7.6 Hz, 1H), 7.67 (d, J = 7.5 Hz, 1H), 7.57 (dd, J = 7.6, 1.5 Hz, 1H), 7.55–7.50 (m, 2H), 7.48–7.26 (m, 9H), 7.26–7.20 (m, 2H), 7.18 (dd, J = 7.5, 1.5 Hz, 1H), 7.12–7.00 (m, 8H), 6.97 (s, 1H), 1.30 (s, 7H).

[0100] Example 7

[0101] This example provides an organic light-emitting compound with a chemical structural formula of Formula L112. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0102]

[0103] Compound L112 (13.3 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-112 (18.6 g) and compound D-001 was changed to intermediate D-112 (9.1 g). The mass spectrum of the obtained solid was measured, and as a result, MS (EI) m / z: [M] + 767.2.

[0104] 1 1H NMR (500 MHz, CDCl3) δ 7.91 (dd, J = 7.4, 1.5 Hz, 1H), 7.74–7.68 (m, 1H), 7.58 (dd, J = 7.4, 1.5 Hz, 1H), 7.44 (td, J = 7.5, 1.5 Hz, 1H), 7.38–7.28 (m, 3H), 7.25 (dd, J = 7.5, 1.8 Hz, 5H), 7.10–7.04 (m, 4H), 6.98 (s, 1H), 1.36 (d, J = 0.7 Hz, 18H).

[0105] Example 8

[0106] This example provides an organic light-emitting compound with a chemical structural formula of Formula L135. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0107]

[0108] Compound L135 (13.3 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-135 (20.6 g) and compound D-001 was changed to intermediate D-135 (16.2 g). The mass spectrum of the obtained solid was measured, and as a result, MS (EI) m / z: [M] + 731.7

[0109] 1 H NMR (500 MHz, CDCl3) δ 7.90 (dd, J = 7.6, 1.5 Hz, 1H), 7.63 (d, J = 1.6 Hz, 1H), 7.57 (dd, J = 7.5, 1.7 Hz, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.45 (td, J = 7.4, 1.5 Hz, 1H), 7.36 (td, J = 7.4, 1.6 Hz, 1H), 7.33–7.21 (m, 6H), 7.13–7.04 (m, 6H), 6.97 (s, 1H), 6.79 (ddd, J = 7.5, 1.5, 0.7 Hz, 1H), 2.93–2.84 (m, 1H), 2.01–1.90 (m, 2H), 1.90–1.78 (m, 2H), 1.68 (tdd, J = 6.5, 3.2, 1.9 Hz, 4H), 1.36 (s, 18H).

[0110] Example 9

[0111] This example provides an organic light-emitting compound with a chemical structural formula of Formula L42. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0112]

[0113] Compound L142 (12.9 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-142 (18.3 g) and compound D-001 was changed to intermediate D-142 (17.4 g). The mass spectrum of the obtained solid was measured, and as a result, MS (EI) m / z: [M] + 707.6

[0114] 11H NMR (500 MHz, CDCl3) δ 7.95 (dd, J = 7.8, 1.6 Hz, 1H), 7.81 (dd, J = 8.7, 1.5 Hz, 1H), 7.64–7.58 (m, 2H), 7.55 (dd, J = 6.8, 1.4 Hz, 1H), 7.51 (dd, J = 6.7, 1.7 Hz, 1H), 7.44 (ddd, J = 8.1, 6.8, 1.3 Hz, 1H), 7.40–7.20 (m, 10H), 7.14–7.08 (m, 2H), 6.98 (s, 1H), 6.97 (td, J = 7.0, 1.8 Hz, 1H), 1.36 (s, 7H), 1.05 (s, 2H).

[0115] Example 10

[0116] This example provides an organic light-emitting compound with the chemical structural formula of formula L155. The reaction route of the preparation method of this organic light-emitting compound is as follows:

[0117]

[0118] Compound L155 (12.2 g) was obtained in the same manner as in the step for synthesizing intermediate L-001, except that compound A-001 was changed to compound A-155 (24.2 g) and compound D-001 was changed to intermediate D-155 (6.9 g). The mass spectrum of the obtained solid was measured, and as a result, MS (EI) m / z: [M] + 781.6

[0119] 1 1H NMR (500 MHz, CDCl3) δ 7.92–7.87 (m, 2H), 7.60–7.53 (m, 6H), 7.55–7.42 (m, 3H), 7.42–7.34 (m, 5H), 7.32–7.22 (m, 8H), 7.12–7.03 (m, 2H), 6.97 (s, 1H), 6.80–6.79 (m, 1H), 2.63 (m, 2H). 1.77–1.61 (m, 4H), 1.63–1.42 (m, 2H), 1.36 (s, 9H).

[0120] Example 11

[0121] An organic electroluminescent device was prepared using the compound L001 prepared in Example 1. Specifically:

[0122] The coating thickness was The ITO glass substrate was washed twice in distilled water, ultrasonically washed for 30 minutes, and then washed twice in distilled water, ultrasonically washed for 10 minutes. After the distilled water washing, it was ultrasonically washed in isopropyl alcohol, acetone, methanol and other solvents in sequence. After drying, it was transferred to a plasma cleaning machine and washed for 5 minutes before being sent to a vapor deposition machine. First, 4,4,4'-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA) was vapor-deposited on the ITO (anode) As a hole injection layer, N-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB) was vacuum-deposited on the formed hole injection layer. As the hole transport layer. On the hole transport layer, the host material BH-1 and the dopant material L001 were mixed and deposited in a weight ratio of 98:2. Then, the electron transport layer is vacuum-deposited on the above-mentioned light-emitting layer. Evaporated electron injection layer Evaporated cathode An organic electroluminescent device was prepared and its luminous properties were tested using a KEITHLEY 2400 source measurement unit and a CS-2000 spectroradiometer to evaluate the driving voltage and luminous efficiency.

[0123]

[0124] Examples 12-20:

[0125] Referring to the above method, compound L001 was replaced by L022, L043, L063, L069, L078, L112, L135, L142 and L155, respectively, to prepare organic electroluminescent devices of the corresponding compounds.

[0126] Comparative Example 1

[0127] An organic electroluminescent device was prepared in the same manner as in Example 11. The structure of the doping material compound of the light-emitting layer was as follows:

[0128]

[0129] Comparative Example 2

[0130] An organic electroluminescent device was prepared in the same manner as in Example 11. The structure of the doping material compound of the light-emitting layer was as follows:

[0131]

[0132] Comparative Example 3

[0133] An organic electroluminescent device was prepared in the same manner as in Example 11, and the structure of the light-emitting layer doping material compound was as follows:

[0134]

[0135] Comparative Example 4

[0136] An organic electroluminescent device was prepared in the same manner as in Example 11, and the structure of the light-emitting layer doping material compound was as follows:

[0137]

[0138] The prepared organic electroluminescent device was tested in the same manner as in Example 11. The driving voltage and luminous efficiency were measured at a current of 10 mA / cm2, and the time (LT95) when the luminance became 95% of the initial luminance was measured at a current density of 20 mA / cm2. The above results are shown in Table 1 below.

[0139] Table 1

[0140]

[0141]

[0142] As can be seen from Table 1, compared with the comparative compounds D1 and D2 with similar structures, the organic electroluminescent device prepared using the compound provided by the present invention as the fluorescent doping material has significantly improved efficiency and lifetime, and also improved in terms of driving voltage.

[0143] Generally, the lifetime of the compound is increased by 8 - 98 h compared with the comparative example. The luminous efficiency is increased by 0.1 - 3.7 cd / A, and the driving voltage is reduced by 0.1 - 1.2 V.

[0144] The applicant declares that the present invention uses the above embodiments to illustrate the organic compounds, organic light-emitting materials and organic electroluminescent devices of the present invention, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of each raw material of the products of the present invention, the addition of auxiliary components, and the selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Chemical Formula 1-1: Wherein, R1 is selected from: hydrogen, deuterium, cyano, a halogen group, or a C1-C20 alkyl group; R2, R3, R4, and R5 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, cyano, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms; n1 to n5 are each an integer from 0 to 5; Among R2, R3, R4, and R5, the substitution is substituted by at least one substituent selected from: hydrogen, deuterium, cyano, a halogen group, a C1-C20 alkyl group, a C6-C30 aryl group, a C6-C30 heteroaryl group, and the heteroatom in the heteroaryl group is selected from oxygen, nitrogen, sulfur, or silicon.

2. The organic compound according to claim 1, wherein R1 is selected from fluorine, methyl, ethyl, isopropyl, tert-butyl, or cyano; R2, R3, R4, and R5 are selected from fluorine, methyl, ethyl, biphenyl, terphenyl, isopropyl, tert-butyl, phenyl, cyclohexane, cyclopentane, adamantyl, cyano, trifluoromethyl, pentafluorophenyl, trimethylsilyl, triphenylsilyl, naphthyl, dibenzofuranyl, dimethylfluorenyl, carbazolyl, or phenyl in which all hydrogen atoms on the benzene ring are replaced by deuterium.

3. An organic compound, characterized in that, The organic compound is any one of the following compounds:

4. An organic optoelectronic material, characterized in that, The organic optoelectronic material includes any one or at least two combinations of the organic compounds described in any one of Claims 1-2 or the organic compound described in Claim 3.

5. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode, and the organic thin film layer includes the organic compound described in any one of Claims 1-2 or the organic compound described in Claim 3.

6. The organic electroluminescent device according to claim 5, wherein The organic thin film layer includes a light-emitting layer, the light-emitting layer contains a host material and a doping material, and the doping material includes the organic compound described in any one of Claims 1-2 or the organic compound described in Claim 3.

7. The organic electroluminescent device according to claim 6, characterized in that, The percentage of the doping material in the light-emitting layer in the total mass of the light-emitting layer materials is 0.5-10%.

8. The organic electroluminescent device according to claim 6, characterized in that, The organic thin film layer further includes any one layer or at least two combinations of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.

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