An organic compound containing a naphthoxazolocarbazole and application thereof

Abstract

The application relates to a naphthoxazolocarbazole-containing organic compound and application thereof, and belongs to the technical field of organic electroluminescent devices. The naphthoxazolocarbazole-containing organic compound has a structural formula I: R is any one of C1-C12 alkyl, substituted or unsubstituted C6-C36 aryl, or substituted or unsubstituted C6-C36 heterocyclic aryl; wherein the substituent group is selected from deuterium and C1-C8 alkyl; the heteroatom in the heterocyclic aryl is selected from oxygen, nitrogen and sulfur; and any H in the structural formula 1 can be independently substituted with deuterium or not. The naphthoxazolocarbazole-containing organic compound is applied to an organic electroluminescent device as an electron transport layer material and / or a host light-emitting material. The prepared organic electroluminescent device can improve the light-emitting performance of the light-emitting device; the light-emitting performance can be current efficiency, driving voltage size, light-emitting life of the device and the like.

Description

TECHNICAL FIELD

[0001] The present application relates to a kind of organic compound containing naphthoxazole and carbazole and its application, belong to organic electroluminescent device technical field. BACKGROUND

[0002] Organic light-emitting device (OLED) is a kind of organic semiconductor material-based light-emitting device, its basic principle is that under electric field driving, electron and hole are injected from cathode and anode respectively, and recombine in light-emitting layer to form exciton, and exciton radiative transition emits visible light. With the continuous progress of material science, device process and driving technology, OLED has realized large-scale industrialization application, and is widely used in smart phones, televisions, wearable devices, vehicle-mounted display and flexible lighting and other fields. OLED has the advantages of simple structure, high yield, low cost, active light-emitting, fast response speed, high resolution and the like.

[0003] In the multilayer thin film structure of OLED device, the selection and design of light-emitting material is particularly important, and its photoelectric property directly determines the final performance of the device. Generally speaking, the functional layer of OLED device includes hole injection layer, hole transport layer, light-emitting layer, electron transport layer and electron injection layer, etc., wherein the light-emitting material not only affects the light-emitting color, efficiency and color purity, but also relates to the working stability and service life of the device.

[0004] The three major problems of OLED at present are still poor stability, low luminous efficiency and insufficient service life. These problems will also restrict the application effect of OLED.

[0005] In OLED, electroluminescent material plays a decisive role in its light-emitting performance. A kind of excellent electroluminescent material is the key to solve the problems faced by OLED, therefore, how to develop an excellent electroluminescent material, especially an electron transport type light-emitting material, is the key work at present. SUMMARY

[0006] The present application provides a kind of organic compound containing naphthoxazole and carbazole and its application, the organic compound containing naphthoxazole and carbazole is used in OLED device electron transport layer and / or light-emitting layer, can significantly improve the luminous efficiency and service life of device.

[0007] The technical scheme for solving the above technical problems of the present application is as follows: an organic compound containing naphthoxazole and carbazole, the structure formula I of the organic compound containing naphthoxazole and carbazole is as follows:

[0008] Structure formula I;

[0009] R is any one of C1-C12 alkyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C6-C36 heterocyclic aryl;

[0010] wherein the substituent is selected from deuterium, C1-C8 alkyl; and the heteroatom in the heterocyclic aryl is selected from oxygen, nitrogen, sulfur;

[0011] Any H in Structural Formula 1 can be independently substituted with deuterium or not substituted with deuterium.

[0012] Further, R is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, pyrenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, 9-phenylcarbazolyl, 11,11-dimethylbenzofluorenyl, 2,4,6-triphenyl-1,3,5-triazinyl; and H in the R group can be independently substituted with deuterium or not substituted with deuterium.

[0013] Further, R is selected from any one of the following groups:

[0014] and H in the R group can be independently substituted with deuterium or not substituted with deuterium.

[0015] Further, the naphthoxazolocarbazole-containing organic compound is selected from any one of the following structural formulas:

[0016] .

[0017] The application also discloses an application of the naphthoxazolocarbazole-containing organic compound, and the naphthoxazolocarbazole-containing organic compound is applied to an organic electroluminescent device.

[0018] Further, the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic compound layer between the two electrodes.

[0019] Further, the naphthoxazolocarbazole-containing organic compound is applied to at least one organic compound layer of the organic electroluminescent device.

[0020] Further, the organic electroluminescent device comprises an anode electrode layer, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode reflection electrode layer.

[0021] Further, the naphthoxazolocarbazole-containing organic compound is applied to an electron transport layer of the organic electroluminescent device.

[0022] Further, the naphthoxazolecarbazole-containing organic compound is applied to a light-emitting layer of an organic electroluminescent device.

[0023] That is, the naphthoxazolecarbazole-containing organic compound is applied to an electron transport layer and / or a light-emitting layer of an organic electroluminescent device.

[0024] The present application has the following advantages:

[0025] The naphthoxazolecarbazole-containing organic compound is applied to an electron transport layer and / or a light-emitting layer of an organic electroluminescent device. The prepared organic electroluminescent device can improve the light-emitting performance of the light-emitting device, and the light-emitting performance can be current efficiency, driving voltage size, and light-emitting life of the device.

[0026] The naphthoxazolecarbazole-containing organic compound of the present application can effectively improve the electron sub-transmission efficiency and deepen the HOME level by introducing nitrogen-containing groups such as carbazole, oxazole, and pyrazine into the parent structure to enhance the local electron cloud density and the n-type conductive ability of the material, so that the thermal stability of the material is significantly improved, and the service life of the device is greatly improved. The introduction of the carbazole structure utilizes the SP 3 hybridization of the nitrogen atom and the SP 2 hybridization of the carbon atom, which weakens the conjugation effect of the whole molecule, thereby maintaining a high triplet energy level and balancing the hole and electron transport abilities, and further improving the light-emitting efficiency and service life of the device. BRIEF DESCRIPTION OF DRAWINGS

[0027] Figure 1 The figure is a schematic diagram of the structure of the organic electroluminescent device described in the application examples.

[0028] In the figure, 1 is a transparent substrate layer, 2 is a transparent anode electrode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode reflection electrode layer. DETAILED DESCRIPTION

[0029] In order to make the above-mentioned objects, features, and advantages of the present application more apparent and easy to understand, the specific embodiments of the present application are described in detail below. In the following description, a large number of specific details are set forth in order to fully understand the present application. However, the present application can be implemented in many other ways different from those described herein, and those skilled in the art can make similar improvements without departing from the scope of the present application, so the present application is not limited to the specific embodiments disclosed below.

[0030] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used in the description herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.

[0031] I. Preparation Examples

[0032] The common intermediate compound C was prepared, and the specific synthesis method was as follows:

[0033] ;

[0034] (1) Preparation of compound A:

[0035] Under the protection of inert gas, 4-chloro-diphenyl-oxazole, bis(pinacolato)diboron, potassium acetate, palladium acetate, 2-dicyclohexylphosphine-2',4',6'-triisopropyl biphenyl (X-phos) and toluene were sequentially added into a three-neck flask, wherein the reaction material ratio was 4-chloro-2-phenyl-oxazole: bis(pinacolato)diboron: potassium acetate: palladium acetate: X-phos = 1.0 eq: 1.2 eq: 4.0 eq: 0.01 eq: 0.02 eq, after the addition of the materials, the stirring was started and the temperature was raised to 100-105°C, and the reaction was completed after 10 h of incubation, and the post-treatment was carried out by hydrolysis, water washing and column treatment, to obtain white solid compound A with a total yield of 67.7% and a GC purity of 98.16%, and the theoretical value of GC-MS was 371.17 and the measured value was 371.20.

[0036] The nuclear magnetic resonance data of compound A were as follows:

[0037] 1 H NMR (500 MHz, Chloroform-d) δ 8.12 – 8.04 (m, 2H), 7.92 (d, J =1.4 Hz, 1H), 7.87 – 7.79 (m, 2H), 7.53 – 7.42 (m, 5H), 1.24 (s, 12H).

[0038] (2) Preparation of compound B:

[0039] Under an inert gas atmosphere, compound A, 5-chloro-6-nitroquinoxaline, potassium carbonate, palladium acetate, X-phos, and toluene were added sequentially to a three-necked flask. The reactant ratio was: compound A: 5-chloro-6-nitroquinoxaline: potassium carbonate: palladium acetate: X-phos = 1.0 eq: 1.0 eq: 3.0 eq: 0.01 eq: 0.02 eq. After the addition was complete, stirring was started, and the temperature was raised to 60–70 °C and maintained for 5 hours until the reaction was complete. The reaction was then post-treated by hydrolysis, extraction, washing with water, column chromatography, solvent removal, and recrystallization to obtain a brownish-yellow compound B. The overall yield was 89.1%, and the GC purity was 96.28%. The theoretical GC-MS value was 418.41, and the measured value was 418.11.

[0040] The NMR data for compound B are as follows:

[0041] 1 H NMR (500 MHz, Chloroform-d) δ 9.34 (d, J = 7.6 Hz, 1H), 8.89 (d, J= 7.6 Hz, 1H), 8.47 (d, J = 7.6 Hz, 1H), 8.30 (d, J = 1.5 Hz, 1H), 8.14 –8.03 (m, 3H), 7.96 –7.90 (m, 1H), 7.85 – 7.79 (m, 1H), 7.54 – 7.43 (m, 5H).

[0042] (3) Preparation of compound C:

[0043] Under an inert gas atmosphere, compound B, triphenylphosphine, and o-dichlorobenzene were added sequentially to a three-necked flask, with a reactant ratio of compound B:triphenylphosphine = 1.0 eq:3.0 eq. After the addition was complete, stirring was started, and the temperature was raised to 175–180 °C and maintained for 20 hours until the reaction was successful. Post-processing yielded a light yellow solid, compound C, with an overall yield of 70.7% and an HPLC purity of 97.32%. The theoretical value of HPLC-MS was 386.41, and the measured value was 387.12.

[0044] The NMR data for compound C are as follows:

[0045] 1H NMR (500 MHz, Chloroform-d) δ 10.93 (s, 1H), 9.34 (d, J = 7.6 Hz,1H), 9.05 (d, J = 7.3 Hz, 1H), 8.15 – 8.07 (m, 2H), 7.94 (ddd,J = 7.8, 6.6,1.5 Hz, 2H), 7.90 (d, J = 7.3 Hz, 1H), 7.83 (d, J = 7.3 Hz, 1H), 7.54 – 7.43(m, 4H), 7.34 (td, J = 7.5, 1.5 Hz, 1H).

[0046] Example 1

[0047] Synthesis of compound A-2:

[0048] ;

[0049] Under inert gas protection, 38.6 g (0.1 mol) of compound C, 28.0 g (0.12 mol) of m-bromobiphenyl, 19.2 g (0.2 mol) of sodium tert-butoxide, 0.915 g (1.0 mmol) of tris(dibenzylacetone)dipalladium, and 0.952 g (2.0 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-phos) were weighed sequentially into a 2 L three-necked flask. Then, 800 g of xylene was added, the temperature was raised to 125.0 °C, and the reaction was maintained at this temperature for 10 h. The reaction was successful, and the HPLC purity was 90.2%. After washing with water, column chromatography, solvent removal, and recrystallization from toluene, 43.0 g of a pale yellow solid compound A-1 was obtained, with a total yield of 80.0% and an HPLC purity of 97.5%. The theoretical value of HPLC-MS was 538.61, and the measured value was 539.20.

[0050] The NMR data for compound A-2 are as follows:

[0051] 1 H NMR (500 MHz, Chloroform-d) δ 9.34 (d, J = 7.6 Hz, 1H), 8.90 (d, J= 7.3 Hz, 1H), 8.15 (dd, J = 7.5, 1.6 Hz, 1H), 8.14 –8.07 (m, 2H), 8.01 –7.94 (m, 2H), 7.90 (dd, J = 7.4, 1.5 Hz, 1H), 7.69 – 7.63 (m, 2H), 7.59 –7.49 (m, 3H), 7.49 –7.33 (m, 9H).

[0052] Example 2

[0053] Synthesis of compound A-5:

[0054] ;

[0055] Under inert gas protection, 38.6 g (0.1 mol) of compound C, 30.7 g (0.1 mol) of 2-bromotriphenylene, 19.2 g (0.2 mol) of sodium tert-butoxide, 0.915 g (1.0 mmol) of tris(dibenzylacetone)dipalladium, and 0.952 g (2.0 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-phos) were weighed sequentially into a 2 L three-necked flask. Then, 1000 g of xylene was added, the temperature was raised to 125.0 °C, and the reaction was maintained at this temperature for 10 h. The reaction was successful, and the HPLC purity was 91.1%. After washing with water, column chromatography, solvent removal, and recrystallization from toluene, 50.1 g of compound A-5 was obtained, with a total yield of 81.8% and an HPLC purity of 97.64%. The theoretical value of HPLC-MS was 612.69, and the measured value was 613.2.

[0056] The NMR data for compound A-5 are as follows:

[0057] 1 H NMR (500 MHz, Chloroform-d) δ 9.34 (d, J = 7.6 Hz, 1H), 8.94 (d, J= 2.1 Hz, 1H), 8.90 (d, J = 7.3 Hz, 1H), 8.20 (dd, J = 7.3, 1.7 Hz, 1H), 8.17– 8.12 (m, 2H), 8.12 –8.08 (m, 2H), 7.97 (d, J = 7.6 Hz, 1H), 7.89 (dd, J =7.4, 1.5 Hz, 1H), 7.86 – 7.80 (m, 1H), 7.66 – 7.61 (m, 1H), 7.61 – 7.46 (m,8H), 7.43 (pd, J = 3.5, 1.5 Hz, 3H), 7.37 (td, J = 7.5, 1.5 Hz, 1H).

[0058] Example 3

[0059] Synthesis of compound A-13:

[0060] ;

[0061] Under inert gas protection, 38.6 g (0.1 mol) of compound C, 23.7 g (0.1 mol) of 1-chloropyrene, 19.2 g (0.2 mol) of sodium tert-butoxide, 0.915 g (1.0 mmol) of tris(dibenzylacetone)dipalladium, and 0.952 g (2.0 mmol) of 2-dicyclohexylphospho-2',4',6'-triisopropylbiphenyl were weighed sequentially into a 2 L three-necked flask. Then, 800 g of xylene was added, the temperature was raised to 125.0 °C, and the reaction was maintained at this temperature for 10 h. The reaction was successful, and the HPLC purity was 90.2%. After washing with water, column chromatography, solvent removal, and recrystallization from toluene, 51.0 g of a light yellow solid compound A-13 was obtained, with a total yield of 86.9% and an HPLC purity of 95.9%. The theoretical value of HPLC-MS was 586.65, and the measured value was 587.20.

[0062] The NMR data for compound A-13 are as follows:

[0063] 1 H NMR (500 MHz, Chloroform-d) δ 9.34 (d, J = 7.6 Hz, 2H), 8.90 (d, J= 7.3 Hz, 2H), 8.18 – 8.15 (m, 1H), 8.15 – 8.08 (m, 7H), 8.08 (d, J = 1.4 Hz,1H), 8.03 – 7.93 (m, 8H), 7.90 (dd, J = 7.4, 1.5 Hz, 2H), 7.84 – 7.78 (m,2H), 7.66 (t, J = 7.7 Hz, 4H), 7.65 – 7.57 (m, 4H), 7.55 (td, J = 7.5, 1.5Hz, 2H), 7.47 – 7.39 (m, 6H), 7.37 (td, J = 7.5, 1.5 Hz, 2H).

[0064] Example 4

[0065] Synthesis of compound A-14:

[0066] ;

[0067] Under inert gas protection, 38.6 g (0.1 mol) of compound G, 32.7 g (0.1 mol) of 2-(3-fluorophenyl)-4,6-diphenyl-1,3,5-triazine, and 97.5 g (0.3 mol) of cesium carbonate were weighed sequentially into a 2 L three-necked flask. Then, 500 g of N,N-dimethylformamide (DMF) was added, and the mixture was stirred and heated to 125.0 °C. The reaction was maintained at this temperature for 20 h, and the result was satisfactory (HPLC: 94.3%). After extraction, washing with water, column chromatography, and recrystallization from o-dichlorobenzene, 60.2 g of a white solid compound A-14 was obtained, with an overall yield of 86.7% (HPLC: 99.9%). The theoretical value of HPLC-MS was 693.77, and the measured value was 694.23.

[0068] The NMR data for compound A-14 are as follows:

[0069] 1 H NMR (500 MHz, Chloroform-d) δ 9.34 (d, J = 7.6 Hz, 1H), 8.90 (d, J= 7.3 Hz, 1H), 8.60 – 8.53 (m, 4H), 8.52 (t, J = 1.5 Hz, 1H), 8.28(dt, J =7.3, 1.5 Hz, 1H), 8.15 (dd, J = 7.4, 1.5 Hz, 1H), 8.12 – 8.07 (m, 2H), 7.97(d, J = 7.3 Hz, 1H), 7.88 (dd, J = 7.5, 1.5 Hz, 1H), 7.66 (t, J = 7.5 Hz,1H), 7.59 –7.49 (m, 3H), 7.49 – 7.39 (m, 9H), 7.36 (td, J = 7.5, 1.5 Hz, 1H).

[0070] Example 5

[0071] Synthesis of compound A-18:

[0072] ;

[0073] Under inert gas protection, 38.6 g (0.1 mol) of compound C, 32.2 g (0.1 mol) of 2-iodo-9-phenyl-9H-carbazole, 19.2 g (0.2 mol) of sodium tert-butoxide, 0.915 g (1.0 mmol) of tris(dibenzylacetone)dipalladium, and 0.952 g (2.0 mmol) of 2-dicyclohexylphospho-2',4',6'-triisopropylbiphenyl were added sequentially to a 2 L three-necked flask. Then, 1500 g of toluene was added, and the mixture was heated to 135.0 °C and maintained at this temperature for 15 h. The reaction was successful, and the HPLC purity was 89.5%. After extraction, washing with water, column chromatography, and recrystallization from o-dichlorobenzene, 48.2 g of compound A-18 was obtained, with a total yield of 76.9% and an HPLC purity of 98.37%. The theoretical value of HPLC-MS was 627.71, and the measured value was 628.21.

[0074] The NMR data for compound A-18 are as follows:

[0075] 1 H NMR (500 MHz, Chloroform-d) δ 9.34 (d, J = 7.6 Hz, 1H), 8.90 (d, J= 7.3 Hz, 1H), 8.17 – 8.07 (m, 4H), 8.00 (d, J = 7.6 Hz, 1H), 7.96(d, J = 7.6Hz, 1H), 7.89 (dd, J = 7.3, 1.5 Hz, 1H), 7.64 – 7.58 (m, 1H), 7.57 – 7.48 (m,4H), 7.48 – 7.39 (m, 6H), 7.39 – 7.24 (m, 5H).

[0076] Example 6

[0077] Synthesis of compound A-22:

[0078] ;

[0079] Under inert gas protection, 38.6 g (0.1 mol) of compound C, 25.4 g (0.1 mol) of 1-bromodibenzo[b,d]furan-2,3,4,6,7,8,9-d7, 19.2 g (0.2 mol) of sodium tert-butoxide, 0.915 g (1.0 mmol) of tris(dibenzylacetone)dipalladium, and 0.952 g (2.0 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were weighed sequentially into a 2 L three-necked flask. Then, 1200 g of xylene was added, the temperature was raised to 130.0 °C, and the reaction was maintained at this temperature for 10 h. The reaction was successful, and the HPLC purity was 92.3%. After extraction, washing with water, column chromatography, and recrystallization from o-dichlorobenzene, 51.5 g of a white solid compound A-22 was obtained, with an overall yield of 92.0% and an HPLC purity of 97.5%. The theoretical value of HPLC-MS is 559.64, and the measured value is 560.20.

[0080] The NMR data for compound A-22 are as follows:

[0081] 1H NMR (500 MHz, Chloroform-d) δ 9.34 (d, J = 7.6 Hz, 1H), 8.90 (d, J= 7.3 Hz, 1H), 8.16 (dd, J = 7.7, 1.6 Hz, 1H), 8.14 –8.07 (m, 2H), 8.05 (d, J = 7.3 Hz, 1H), 7.85 (dd, J = 7.6, 1.4 Hz, 1H), 7.59 – 7.52 (m, 2H), 7.46 –7.40 (m, 3H), 7.37 (td, J = 7.5, 1.5 Hz, 1H).

[0082] Example 7

[0083] Synthesis of compound A-23:

[0084] ;

[0085] (1) Compound A-1 was synthesized using the synthesis method of compound A-1 in Example 1.

[0086] Under inert gas protection, 38.6 g (0.1 mol) of compound C, 18.8 g (0.12 mol) of bromobenzene, 19.2 g (0.2 mol) of sodium tert-butoxide, 0.915 g (1.0 mmol) of tris(dibenzylacetone)dipalladium, and 0.952 g (2.0 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-phos) were weighed sequentially into a 2 L three-necked flask. Then, 200 g of xylene was added, and the mixture was heated to 125–130 °C and maintained at this temperature for 10 h. The reaction was successful, and the HPLC purity was 93.6%. After washing with water, column chromatography, solvent removal, and recrystallization from toluene, 35.0 g of compound A-1 was obtained, with a yield of 75.8% and an HPLC purity of 97.2%. The theoretical value of HPLC-MS was 462.51, and the measured value was 463.21.

[0087] (2) A-23 was synthesized by deuteration reaction.

[0088] 46.2 g (0.1 mol) of compound A-1, 105.0 g (0.7 mol) of trifluoromethanesulfonic acid, and 579 g (6.88 mol) of deuterated benzene were added to a 1 L three-necked flask under nitrogen atmosphere. The mixture was then heated to 40–50 °C and reacted for 36 h. After the reaction was complete, 100 g of heavy water was added for hydrolysis, followed by dissolution with 1000 g of dichloromethane and washing with water. After washing four times with water, the organic phase was dried and passed through a silica gel column, then purified by recrystallization from toluene to obtain 35.4 g of compound A-23, with a total yield of 73.8% and an HPLC purity of 97.50% (mass spectrometry, calculated value 480.62; measured value 475.2). NMR analysis showed a deuteration rate of 70.8%.

[0089] The synthesis methods of other compounds included in this invention are the same as or similar to those in the specific implementation examples, and will not be listed one by one. The mass spectrometry test data of the synthesized organic compounds are shown in Table 1 below. The main raw materials and some excipients used to synthesize the compounds in the specific implementation examples are all known compounds, and the specific information CAS numbers are shown in Table 2.

[0090] Table 1 Mass-to-nucleus ratio of compounds

[0091]

[0092] Table 2 CAS Numbers of Relevant Main Raw Materials and Auxiliary Materials

[0093]

[0094] II. Fabrication and Evaluation of Organic Electroluminescent Devices

[0095] The following application examples 1-15 and comparative examples 1-4 illustrate in detail the application effects of the OLED luminescent materials synthesized in this invention on devices.

[0096] Application Example 1

[0097] The structure of organic electroluminescent devices is as follows Figure 1 As shown, the transparent anode electrode layer 2 (film thickness of 205 nm, indium tin oxide) with a transparent substrate layer 1 is processed as follows: First, photolithography and etching are performed to form the required regular transparent anode electrode layer 2. Then, the glass transparent substrate layer 1 is washed, namely, by sequentially performing alkaline washing, distilled water washing, isopropanol ultrasonic cleaning, acetone ultrasonic cleaning, ethanol ultrasonic cleaning, ultrapure water cleaning, and drying. Finally, the transparent anode electrode layer 2 is subjected to ultraviolet-ozone washing to ensure the removal of organic residues on the surface of the transparent anode electrode layer 2. After the above treatment, a hole injection layer 3 is deposited on the transparent anode electrode layer 2 by evaporation. Using a vacuum evaporation apparatus, structure type one (NPB) material is deposited (evaporation conditions: molybdenum crucible, evaporation rate 0.1 nm / s, vacuum degree 4.0 × 10⁻⁶). -5 The organic material, with a thickness of 55 nm, is used as hole injection layer 3. Immediately following hole injection layer 3, a 25 nm thick mCP material is deposited as hole transport layer 4. Following hole transport layer 4, a 20 nm thick TCTA material is deposited as electron blocking layer 5. After electron blocking layer 5 is deposited, A-2 material is deposited onto the empty electron blocking layer 5 (deposition conditions: molybdenum crucible, deposition rate 0.1 nm / s, vacuum degree 4.0 × 10⁻⁶). -5 Pa) yielded a light-emitting layer 6 with a thickness of 35 nm.

[0098] A hole-blocking layer 7 material (the material shown in structural formula five (TmPyPB)) is deposited on the light-emitting layer 6 by vapor deposition (deposition conditions: using a molybdenum crucible, deposition rate 0.1 nm / s, vacuum degree 4.0*10). -5 The vacuum-deposited film of this material (DPyPA) is 20 nm thick. After the deposition, the material shown in structure six (DPyPA) is then deposited to obtain electron transport layer 8 with a film thickness of 85 nm. On electron transport layer 8, a lithium fluoride (LiF) layer with a thickness of 1.0 nm is fabricated as electron injection layer 9 using a vacuum deposition apparatus.

[0099] A cathode reflective electrode layer 10 is deposited on the electron injection layer 9 by vacuum evaporation. The cathode reflective electrode layer 10 is an aluminum (Al) layer with a film thickness of 148 nm.

[0100] The structural formulas of the raw materials involved in the fabrication of organic electroluminescent devices are as follows:

[0101] .

[0102] After completing the organic OLED electroluminescent device as described above, the anode and cathode are connected using a known driving circuit, and then the current-voltage performance, luminous efficiency, and emission spectrum of the device are measured.

[0103] Application Examples 2 through 17 were carried out using the same method as Application Example 1, except that different compounds or deuterated compounds, such as A-3 to A-24, were used instead of compound A-2 provided in Example 1 of Application Example 1 as the main material.

[0104] According to the above-described OLED device fabrication process, the fabrication processes of the devices described in Comparative Examples 1-5 and Application Examples 1-17 of the present invention are completely identical, and the same substrate material and electrode material are used. The film thickness of the electrode material is the same. The only difference is that the light-emitting layer and / or electron transport layer are replaced with the materials of the present invention. The compounds used in the main structural layers of the devices fabricated in Comparative Examples 1-5 and Application Examples 1-17 are shown in Table 3.

[0105] Table 3. Structural materials of different OLED devices

[0106]

[0107] The above-mentioned OLED devices were subjected to device performance and lifetime tests according to the above test methods to evaluate the driving voltage, current efficiency, external quantum efficiency and emission color of the light-emitting devices; the test results of the light-emitting characteristics of the obtained devices are shown in Table 4.

[0108] Application Examples 1-17 and Comparative Examples 1-4 are used when the brightness is the same (1000 cd / m²). 2 The test results under the same ambient temperature (25.0℃) and humidity (30.0%) are shown in Table 4.

[0109] Table 4 Device performance test results

[0110]

[0111] According to the data comparison in Table 4, the compounds obtained in this invention (application examples A-1 to A-24) and the organic compounds with structures provided by this invention are excellent performance when applied to OLED devices as the main material and light-emitting material of the light-emitting layer. The luminous efficiency and lifetime characteristics of organic light-emitting devices are significantly improved.

[0112] The organic light-emitting device using a light-emitting layer material containing a naphthooxazolocarbazole structure, as described in this invention, can achieve a structure with good luminous efficiency and lifetime, and therefore can be applied to the highly practical OLED industry.

[0113] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0114] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the protection scope of the present invention. Therefore, the protection scope of this invention patent should be determined by the appended claims.

Claims

1. An organic compound containing naphthooxazolocarbazole, characterized in that, The structural formula I of the organic compound containing naphthooxazolocarbazole is as follows: Structural Formula I; R is any one of C1-C12 alkyl, substituted or unsubstituted C6-C36 aryl, or substituted or unsubstituted C6-C36 heterocyclic aryl; Wherein, the substituents are selected from deuterium and C1-C8 alkyl groups; the heteroatoms in the heterocyclic aryl group are selected from oxygen, nitrogen, and sulfur; In structural formula 1, any H can be independently substituted by deuterium or not substituted by deuterium.

2. An organic compound containing naphthooxazolocarbazole according to claim 1, characterized in that, The R is selected from any one of phenyl, naphthyl, phenanthryl, pyrene, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, and 11,11-dimethylbenzofluorenyl; and the H in the R group may be independently substituted with deuterium or not substituted with deuterium.

3. An organic compound containing naphthooxazolocarbazole according to claim 1, characterized in that, The R is selected from any one of the following groups: Furthermore, the H in the R group can be independently substituted by deuterium or not substituted by deuterium.

4. An organic compound containing naphthooxazolocarbazole, characterized in that, The organic compounds containing naphthooxazolocarbazole are selected from any one of the following structural formulas: 。 5. The application of an organic compound containing a naphthooxazolocarbazole class according to any one of claims 1-4, characterized in that, The organic compounds containing naphthooxazolocarbazole are used in organic electroluminescent devices.

6. The application of the organic compound containing naphthooxazolocarbazole as described in claim 5, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and at least one layer of organic compound located between the two electrodes.

7. The application of the organic compound containing naphthooxazolocarbazole according to claim 6, characterized in that, The organic compound containing naphthooxazolocarbazole is applied to at least one organic compound layer in the organic electroluminescent device.

8. The application of the organic compound containing naphthooxazolocarbazole according to claim 5, characterized in that, The organic electroluminescent device includes an anode electrode layer, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode reflective electrode layer.

9. The application of the organic compound containing naphthooxazolocarbazole according to claim 5, characterized in that, The organic compounds containing naphthooxazol and carbazole are used in the electron transport layer of organic light-emitting devices.

10. The application of the organic compound containing naphthooxazolocarbazole according to claim 5, characterized in that, The organic compounds containing naphthooxazol and carbazole are used in the light-emitting layer of organic electroluminescent devices.

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