Organic compound containing triphenylene group, electroluminescent device and display device
By providing an organic compound containing triphenylene groups, the electron barrier layer and hole transport layer used in the OLED device, the shortcomings of existing OLED materials in terms of current efficiency, driving voltage and lifetime are solved, and OLED devices with higher performance and longer lifetime are achieved.
Patent Information
- Application Number
- CN202111355621.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2021-11-16
- Publication Date
- 2025-04-04
- Estimated Expiration
- 2041-11-16
Smart Images

Figure BDA0003356972190000021 
Figure BDA0003356972190000032 
Figure BDA0003356972190000041
Abstract
Description
Technical Field
[0001] The present invention belongs to the field of electroluminescence, and particularly relates to an organic compound, an organic electroluminescent device and a display device, and more particularly to an organic compound containing a triphenylene group, an electroluminescent device and a display device. Background Art
[0002] Currently, organic electroluminescent (OLED) display technology has been applied in fields such as smartphones and tablets, and is expected to expand into larger display applications such as televisions. Over the past 30 years, researchers have developed a variety of high-performance OLED materials. Through diverse device structural designs and optimization of performance factors such as device lifespan and efficiency, OLED's commercialization has been accelerated, leading to its widespread application in the display and lighting fields.
[0003] The selection of materials for the hole layer, light-emitting layer, and other organic functional layers also has a significant impact on the current efficiency, driving voltage, and lifespan of the device. Currently, we are still exploring functional layer materials with higher performance.
[0004] Therefore, in order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of OLED materials with higher performance. Summary of the Invention
[0005] To address the shortcomings of the prior art, the present invention provides an organic compound, an organic electroluminescent device, and a display device, particularly an organic compound containing a triphenylene group, an electroluminescent device, and a display device. The organic compound of the present invention can be used as an electron-blocking layer material and a hole-transporting layer material for OLED light-emitting devices.
[0006] To achieve this object, the present invention adopts the following technical solutions:
[0007] In one aspect, the present invention provides an organic compound having a structure shown in Formula I:
[0008]
[0009] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C40 aryl groups, substituted or unsubstituted C5-C40 heteroaryl groups; and when one of Ar1 and Ar2 is selected from biphenyl, the other is not The wavy lines represent the attachment sites of the groups;
[0010] R1, R2, R3 and R4 are independently selected from H, F, CN, D (deuterium), substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C6-C40 aryl;
[0011] When the substituted or unsubstituted group contains a substituent, the substituent is selected from F, CN, D (deuterium), C1-C6 alkyl, C1-C6 alkoxy, and C6-C40 aryl.
[0012] Preferably, the C6 to C40 aromatic group is selected from one or a combination of two or more of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthacenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthacenyl, and benzonaphthofluorenyl.
[0013] Preferably, the C5-C40 heteroaryl group is selected from dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, dibenzodibenzofuranyl, dibenzodibenzothiophenyl, naphthodibenzofuranyl, naphthodibenzothiophenyl, benzonaphthodibenzofuranyl or benzonaphthodibenzothiophenyl.
[0014] Preferably, Ar1 and Ar2 are the same.
[0015] Preferably, Ar1 and Ar2 are different.
[0016] Preferably, Ar1 and Ar2 are independently selected from wherein each occurrence of R is hydrogen, C1-C5 (e.g., C1, C2, C3, C4, or C5) alkyl, or C6-C12 (e.g., C6, C7, C8, C9, C10, C11, or C12) aryl, X is O or S, and the wavy line represents the point of attachment of the group.
[0017] Preferably, at least one of Ar1 and Ar2 is selected from substituted or unsubstituted C5-C40 heteroaryl groups.
[0018] More preferably, at least one of Ar1 and Ar2 is selected from a triphenylene group or a fluoranthene group.
[0019] Preferably, the organic compound has the structure shown in Formula I-1:
[0020]
[0021] where R 11 , R 12 Independently selected from H, substituted or unsubstituted C6-C20 aryl groups; when the substituted or unsubstituted group contains a substituent, the substituent is selected from F, CN, D (deuterium), C1-C6 alkyl, C1-C6 alkoxy, and C6-C40 aryl groups.
[0022] Further preferably, the organic compound has a structure shown in Formula I-2:
[0023]
[0024] where R 11 、R 12 、R 13 and R 14 Independently selected from H, substituted or unsubstituted C6-C20 aryl groups; when the substituted or unsubstituted group contains a substituent, the substituent is selected from F, CN, D (deuterium), C1-C6 alkyl, C1-C6 alkoxy, and C6-C40 aryl groups.
[0025] In the present invention, the range of carbon atom number is defined in the definition of the group, and the carbon atom number is any integer within the defined range. For example, C6-C40 aromatic group, the carbon atom number of the aromatic group can be any integer within the range of 6-40, such as 6, 8, 10, 15, 20, 30, 35, 38 or 40, etc. The carbon atom number definition range of other groups has the same meaning by analogy.
[0026] Preferably, the organic compound is any one of the following compounds:
[0027]
[0028]
[0029]
[0030]
[0031]
[0032]
[0033]
[0034] In the present invention, the synthesis path of the organic compound is as follows:
[0035]
[0036] That is, using bromine and iodine substituted benzene ring compounds to react with Ar-B(OH)2 to generate Then and Reaction to generate the compound shown in formula I.
[0037] When R1 and R4 are the same, and R2 and R3 are the same, the following synthetic route can be used:
[0038]
[0039] In another aspect, the present invention provides an electron blocking layer comprising the organic compound as described above.
[0040] In another aspect, the present invention provides a hole transport layer, comprising the organic compound as described above.
[0041] In another aspect, the present invention provides an organic electroluminescent device, comprising the organic compound as described above.
[0042] Preferably, the organic electroluminescent device comprises an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, and the organic thin film layer comprises the organic compound described above.
[0043] Preferably, the organic thin film layer includes an electron blocking layer, and the electron blocking layer includes the organic compound as described above.
[0044] Preferably, the organic electroluminescent device comprises a hole transport layer.
[0045] Preferably, the hole transport layer comprises an organic compound as described above.
[0046] In another aspect, the present invention provides a display device, comprising the organic electroluminescent device as described above.
[0047] Compared with the prior art, the present invention has the following beneficial effects:
[0048] The organic compound of the present invention can be used as an electron blocking layer and a hole transport layer of an OLED device to improve material properties. The organic electroluminescent device prepared using the compound of the present application as the electron blocking layer of the OLED device has a longer lifespan, and the organic electroluminescent device prepared using the compound of the present application as the hole transport layer of the OLED device has a higher efficiency. DETAILED DESCRIPTION
[0049] The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.
[0050] Synthesis Example 1 Synthesis of Compound 1
[0051]
[0052] (1) Synthesis of intermediate M-1-1:
[0053] To a 250 ml three-necked flask, under nitrogen protection, were added 50 ml of toluene, 30 ml of ethanol, and 15 ml of water, followed by 2.36 g (0.01 mol) of o-dibromobenzene, 2.72 g (0.01 mol) of triphenylene-2-boric acid, 2.12 g (0.02 mol) of sodium carbonate, and 0.115 g (0.0001 mol) of tetrakistriphenylphosphine palladium. The temperature was slowly raised to 60°C for reaction for 4 hours, then raised to reflux for reaction for 4 hours, cooled, and separated by adding water. The organic layer was washed with water and dried over magnesium sulfate. The magnesium sulfate was removed by filtration, and the solvent was removed under reduced pressure. The obtained solid was separated by column chromatography and eluted with petroleum ether to obtain 2.7 g of the intermediate shown in M-1-1.
[0054] The intermediate shown in M-1-1 was detected by mass spectrometry. The two peaks with the largest m / z values were 382 and 384, and the molecular formula of the product was determined to be C 24 H 15 Br.
[0055] (2) Synthesis of Compound 1:
[0056] To a 500 ml three-necked flask, under nitrogen protection, were added 200 ml of dry toluene, 3.83 g (0.01 mol) of the compound shown in M-1-1, 3.21 g (0.01 mol) of diphenylamine, 0.0575 g (0.0001 mol) of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 0.4 g (0.0002 mol) of a toluene solution containing 10% tri-tert-butylphosphine, and 1.44 g (0.015 mol) of sodium tert-butoxide. The mixture was heated to reflux for 6 hours, cooled, and separated by adding water. The organic layer was washed with water until neutral, dried over magnesium sulfate, filtered to remove magnesium sulfate, and concentrated to dryness. The mixture was separated by silica gel column chromatography and eluted with petroleum ether:ethyl acetate = 10:0.5 (volume ratio) to obtain 5.1 g of compound 1.
[0057] Compound 1 was detected by mass spectrometry, and the m / z of the molecule was determined to be 623.
[0058] Compound 1 was subjected to nuclear magnetic resonance detection, and the data analysis is as follows: 1H-NMR (Bruker, Switzerland, AvanceⅡ400MHz nuclear magnetic resonance spectrometer, CDCl3), δ9.58 (m, 1H), δ9.10 (d, 1H), δ8.68 (d, 1H), δ8.40 (m, 1H), δ8.31 (m, 1H), δ8.11 (m, 1H), δ7.78~7.60 (m, 8H), δ7.59~7.34 (m, 18H), δ7.15 (m, 1H).
[0059] Synthesis Example 2 Synthesis of Compound 5
[0060]
[0061] (1) Synthesis of intermediate M-5-1:
[0062] The synthesis method refers to the synthesis of intermediate M-1-1 in Example 1, except that the triphenylene-2-boronic acid is replaced with 7-(2-naphthyl)-triphenylene-2-boronic acid to obtain the intermediate shown in M-5-1.
[0063] The intermediate shown in M-5-1 was detected by mass spectrometry. The two peaks with the largest m / z values were 508 and 510. The molecular formula of the product was determined to be C 34 H 21 Br.
[0064] (2) Synthesis of compound 5:
[0065] The synthesis method refers to the synthesis of compound 1 in Example 1, except that the intermediate M-1-1 is replaced by intermediate M-5-1, and the diphenylamine is replaced by N-phenylbenzidine to obtain compound 5.
[0066] Compound 5 was detected by mass spectrometry, and the m / z of the molecule was determined to be 673.
[0067] Synthesis Example 3 Synthesis of Compound 21
[0068]
[0069] (1) Synthesis of intermediate M-21-1:
[0070] In a 250 ml three-necked flask, under nitrogen protection, were added 80 ml of dry toluene, 2.54 g (0.015 mol) of benzidine, 3.89 g (0.01 mol) of 2-bromo-6,6,12,12-tetramethyl-6,12-dihydroindole[1,2-b]fluorene, 0.0575 g (0.0001 mol) of Pd(dba)2 (bis(dibenzylideneacetonepalladium), 0.4 g (0.0002 mol) of a toluene solution containing 10% tri-tert-butylphosphine, and 1.44 g (0.015 mol) of sodium tert-butoxide. The mixture was heated to reflux for 8 hours, cooled, and separated by adding water. The organic layer was washed twice with 2% hydrochloric acid and washed with water until neutral, dried over magnesium sulfate, filtered to remove the magnesium sulfate, concentrated to dryness, and recrystallized from a mixed solvent of methanol and toluene to obtain 3.1 g of the intermediate represented by formula M-21-1.
[0071] The intermediate represented by formula M-21-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 477.
[0072] (2) Synthesis of Compound 21:
[0073] The synthesis method refers to the synthesis of compound 1 in Example 1, except that the diphenylamine therein is replaced with the intermediate shown in M-21-1 to obtain compound 21.
[0074] Compound 21 was detected by mass spectrometry, and the m / z of the molecule was determined to be 779.
[0075] Synthesis Example 4 Synthesis of Compound 33
[0076]
[0077] (1) Synthesis of intermediate M-33-1:
[0078] Referring to the synthesis of intermediate M-21-1, except that the corresponding bromide and amine were selected, intermediate M-33-1 was obtained.
[0079] The intermediate represented by formula M-33-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 369.
[0080] (2) Synthesis of compound 33:
[0081] Referring to the synthesis of compound 1, compound 33 was obtained by using the corresponding bromide and diarylamine.
[0082] Compound 33 was detected by mass spectrometry, and the m / z of the molecule was determined to be 671.
[0083] Synthesis Example 5 Synthesis of Compound 37
[0084]
[0085] Referring to the synthesis of compound 1, except that the corresponding bromide and diarylamine were used, compound 37 was obtained.
[0086] Compound 37 was detected by mass spectrometry, and the m / z of the molecule was determined to be 771.
[0087] Synthesis Example 6 Synthesis of Compound 45
[0088]
[0089] (1) Synthesis of intermediate M-45-1:
[0090] Refer to the synthesis of intermediate M-1-1, except that 3-bromo-4-iodotoluene is used instead of o-dibromobenzene, and the reaction conditions are 60°C for 8 hours to obtain intermediate M-45-1.
[0091] The intermediate shown in formula M-45-1 was detected by mass spectrometry. The two peaks with the largest m / z values were 396 and 398. The molecular formula of the product was determined to be: C 25 H 17 Br.
[0092] (2) Synthesis of compound 45:
[0093] Referring to the synthesis of compound 1, except that the corresponding bromide and diarylamine were used, compound 45 was obtained.
[0094] Compound 45 was detected by mass spectrometry, and the m / z of the molecule was determined to be 637.
[0095] Synthesis Example 7 Synthesis of Compound 49
[0096]
[0097] (1) Synthesis of intermediate M-49-1:
[0098] Referring to the synthesis of intermediate M-1-1, except that 4,5-diphenyl-1,2-dibromobenzene is used instead of o-dibromobenzene, intermediate M-49-1 is obtained.
[0099] The intermediate shown in formula M-49-1 was detected by mass spectrometry. The two peaks with the largest m / z values were 534 and 536. The molecular formula of the product was determined to be: C 36 H 23 Br.
[0100] (2) Synthesis of compound 49:
[0101] Referring to the synthesis of compound 1, except that the corresponding bromide and diarylamine were used, compound 49 was obtained.
[0102] Compound 49 was detected by mass spectrometry, and the m / z of the molecule was determined to be 775.
[0103] Synthesis Example 8 Synthesis of Compound 56
[0104]
[0105] (1) Synthesis of intermediate M-56-1:
[0106] Referring to the synthesis of intermediate M-45-1, except that the corresponding bromide (iodide) was selected, intermediate M-56-1 was obtained.
[0107] The intermediate shown in formula M-56-1 was detected by mass spectrometry. The two peaks with the largest m / z values were 442 and 440. The molecular formula of the product was determined to be: C 27 H 21 BrO.
[0108] (2) Synthesis of compound 56:
[0109] The synthesis of compound 1 was followed, except that the corresponding bromide and diarylamine were used to obtain compound 56. Compound 56 was subjected to mass spectrometry and the molecular m / z was determined to be 681.
[0110] Synthesis Example 9 Synthesis of Compound 66
[0111]
[0112] The synthesis of compound 1 was followed, except that the corresponding bromide and diarylamine were used to obtain compound 66. Compound 66 was detected by mass spectrometry, and the molecular m / z was determined to be 763.
[0113] Synthesis Example 10 Synthesis of Compound 72
[0114]
[0115] (1) Synthesis of intermediate M-72-1:
[0116] Referring to the synthesis of intermediate M-21-1, except that the corresponding bromide and amine were selected, intermediate M-72-1 was obtained.
[0117] The intermediate represented by formula M-72-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 487.
[0118] (2) Synthesis of Compound 72:
[0119] Referring to the synthesis of compound 1, except that the corresponding bromide and diarylamine were used, compound 72 was obtained.
[0120] Compound 72 was detected by mass spectrometry, and the m / z of the molecule was determined to be 789.
[0121] Synthesis Example 11 Synthesis of Compound 76
[0122]
[0123] (1) Synthesis of intermediate M-76-1:
[0124] Referring to the synthesis of intermediate M-21-1, except that the corresponding bromide and amine were selected, intermediate M-76-1 was obtained.
[0125] The intermediate represented by formula M-76-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be: 501.
[0126] (2) Synthesis of Compound 76:
[0127] Referring to the synthesis of compound 1, except that the corresponding bromide and diarylamine were used, compound 76 was obtained.
[0128] Compound 76 was detected by mass spectrometry, and the m / z of the molecule was determined to be 803.
[0129] Synthesis Example 12 Synthesis of Compound 91
[0130]
[0131] (1) Synthesis of intermediate M-91-1:
[0132] Referring to the synthesis of intermediate M-21-1, except that the corresponding bromide and amine were selected, intermediate M-91-1 was obtained.
[0133] The intermediate represented by formula M-91-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 577.
[0134] (2) Synthesis of Compound 91:
[0135] Referring to the synthesis of compound 1, except that the corresponding bromide and diarylamine were used, compound 91 was obtained.
[0136] Compound 91 was detected by mass spectrometry, and the m / z of the molecule was determined to be 879.
[0137] Synthesis Example 13 Synthesis of Compound 106
[0138]
[0139] (1) Synthesis of intermediate M-106-1:
[0140] Referring to the synthesis of intermediate M-21-1, except that the corresponding bromide and amine were selected, intermediate M-106-1 was obtained.
[0141] The intermediate represented by formula M-106-1 was subjected to mass spectrometry detection, and the molecular m / z was determined to be 425.
[0142] (2) Synthesis of Compound 106:
[0143] Referring to the synthesis of compound 1, except that the corresponding bromide and diarylamine were used, compound 106 was obtained.
[0144] Compound 106 was detected by mass spectrometry, and the m / z of the molecule was determined to be 727.
[0145] Other compounds in the present invention can be synthesized by referring to the above methods in combination with common knowledge in the art, and are not listed here one by one.
[0146] Materials used in the device examples:
[0147]
[0148]
[0149] Device Example 1
[0150] In the examples, the compounds of the present application were used as hole transport materials in organic electroluminescent devices. In the comparative examples, HT-1 to HT-4 were used as hole transport materials in organic electroluminescent devices.
[0151] The structure of the organic electroluminescent device is: ITO / HIL02 (80 nm) / hole transport material (35 nm) / EM1 (30 nm) / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).
[0152] The preparation process of organic electroluminescent devices is as follows:
[0153] A glass substrate coated with an ITO transparent conductive layer (as an anode) was ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, and baked in a clean environment until the water was completely removed. The substrate was then cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the surface properties and enhance its binding ability with the hole injection layer.
[0154] The glass substrate was placed in a vacuum chamber and evacuated to 1×10 -5 ~9×10 -4 Pa, vacuum evaporate HIL02 on the anode as a hole injection layer, the evaporation rate is 0.01nm / s, and the evaporated film thickness is 80nm;
[0155] The compound of the present application or the comparative material was vacuum evaporated on the hole injection layer as a hole transport layer at a deposition rate of 0.01 nm / s and a deposition film thickness of 35 nm;
[0156] EM1 was vacuum evaporated on the hole transport layer as the organic light-emitting layer of the device at a deposition rate of 0.01 nm / s and a total film thickness of 30 nm.
[0157] TPBI was vacuum-deposited on the organic light-emitting layer as an electron transport layer of the organic electroluminescent device; the evaporation rate was 0.01 nm / s, and the total film thickness was 30 nm;
[0158] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer to serve as the electron injection layer and cathode.
[0159] The only difference between other examples and comparative examples and Example 1 is that the hole transport materials used are shown in Table 1.
[0160] The devices obtained from the above device examples and comparative examples were characterized for brightness, driving voltage, and current efficiency using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang.
[0161] The performance results of the organic electroluminescent device are shown in Table 1.
[0162] Table 1
[0163]
[0164]
[0165] As can be seen from the data in Table 1, the organic electroluminescent devices using the compounds of the present application as hole transport materials reduce the driving voltage to below 4.92 V and the current efficiency is above 1.08 cd / A. In particular, the devices corresponding to compounds 66 to 106 have a significant reduction in driving voltage while significantly improving efficiency, making the driving voltage as low as below 4.11 V and the current efficiency as high as above 1.42 cd / A.
[0166] Device Example 14
[0167] In the examples, the compounds of the present application were used as electron blocking layer materials in organic electroluminescent devices. In the comparative examples, HT-1 to HT-2 were used as electron blocking layer materials in organic electroluminescent devices.
[0168] The structure of the organic electroluminescent device is: ITO / HIL02 (80 nm) / NPB (35 nm) / electron blocking layer (15 nm) / / EM1 (30 nm) / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).
[0169] The preparation process of organic electroluminescent devices is as follows:
[0170] A glass substrate coated with an ITO transparent conductive layer (as an anode) was ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, and baked in a clean environment until the water was completely removed. The substrate was then cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the surface properties and enhance its binding ability with the hole injection layer.
[0171] The glass substrate was placed in a vacuum chamber and evacuated to 1×10 -5 ~9×10 -4 Pa, vacuum evaporate HIL02 on the anode as a hole injection layer, the evaporation rate is 0.01nm / s, and the evaporated film thickness is 80nm;
[0172] NPB was vacuum evaporated on the hole injection layer as a hole transport layer at a rate of 0.01 nm / s and a film thickness of 35 nm.
[0173] The compound of the present invention and the comparative compound were vacuum-deposited on the hole transport layer as the electron blocking layer of the device, respectively, at a deposition rate of 0.01 nm / s and a total deposition thickness of 15 nm;
[0174] EM1 was vacuum evaporated on the electron blocking layer as the organic light-emitting layer of the device at a deposition rate of 0.01 nm / s and a total film thickness of 30 nm.
[0175] TPBI was vacuum-deposited on the organic light-emitting layer as an electron transport layer of the organic electroluminescent device; the evaporation rate was 0.01 nm / s, and the total film thickness was 30 nm;
[0176] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer to serve as the electron injection layer and cathode.
[0177] The only difference between Examples 15-18 and Comparative Examples 3-4 and Example 14 is that the electron blocking materials used are shown in Table 2.
[0178] The devices obtained from the above device examples and comparative examples were characterized in terms of brightness, driving voltage, current efficiency and LT95 performance using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang. LT95 refers to maintaining an initial brightness of 1000 cd / m 2 The time (hours) required for the device brightness to drop to 95% of the initial brightness when the current density remains unchanged is shown in Table 2.
[0179] Table 2
[0180]
[0181]
[0182] From the data in Table 2, it can be seen that the organic electroluminescent device using the chemical combination of the present application as the electron blocking material can reduce the driving voltage to below 5.02V, the current efficiency is above 1.09cd / A, and the life span reaches more than 44h.
[0183] The applicant states that while the present invention uses the aforementioned embodiments to illustrate the organic compounds, organic electroluminescent devices, and display devices of the present invention, the present invention is not limited to these embodiments, nor does it necessarily rely on these embodiments for implementation. Persons skilled in the art should understand that any improvements to the present invention, equivalent substitutions for raw materials in the products of the present invention, additions of auxiliary components, and selection of specific methods, etc., fall within the scope of protection and disclosure of the present invention.
Claims
1. An organic compound, characterized in that The organic compound has a structure shown in Formula I: Ar1 and Ar2 are independently selected from and at least one of Ar1 and Ar2 is selected from wherein R at each occurrence is hydrogen, C1-C5 alkyl or C6-C12 aryl, X is O or S, and the wavy line represents the attachment site of the group; R1, R2, R3 and R4 are independently selected from H, F, CN, deuterium or phenyl.
2. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are the same.
3. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are not the same.
4. The organic compound according to claim 1, characterized in that At least one of Ar1 and Ar2 is selected from triphenylene or fluoranthene.
5. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in Formula I-1: Where R 11 , R 12 Independently selected from H, phenyl, biphenyl.
6. The organic compound according to claim 5, characterized in that The organic compound has a structure shown in Formula I-2: Where R 11 , R 12 , R 13 and R 14 Independently selected from H, phenyl, biphenyl.
7. An organic compound, characterized in that The organic compound is any one of the following compounds:
8. An electron blocking layer, characterized in that: The electron blocking layer comprises the organic compound according to any one of claims 1 to 7.
9. An organic hole transport layer, characterized in that: The hole transport layer comprises the organic compound according to any one of claims 1 to 7.
10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the organic compound according to any one of claims 1 to 7.
11. The organic electroluminescent device according to claim 10, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, and the organic thin film layer comprises the organic compound according to any one of claims 1 to 7.
12. The organic electroluminescent device according to claim 11, characterized in that: The organic thin film layer comprises an electron blocking layer, and the electron blocking layer comprises the organic compound according to any one of claims 1 to 7.
13. The organic electroluminescent device according to claim 10, characterized in that: The organic electroluminescent device includes a hole transport layer.
14. The organic electroluminescent device according to claim 13, characterized in that: The hole transport layer comprises the organic compound according to any one of claims 1 to 7.
15. A display device, characterized in that: The display device comprises the organic electroluminescent device according to any one of claims 10 to 14.
Citation Information
Patent Citations
Compound, application thereof and organic electroluminescent device containing compound
CN110317139A
Novel compound and organic light emitting element using same
CN110799487A
Compound containing silafluorenyl and fluorenyl structures and electroluminescent device containing compound
CN111196822A
Compound, organic electronic light-emitting device comprising the same and application
CN111606813A
Organic light emitting diode
CN112424965A