Organic compound containing triphenylene group, electroluminescent device and display device

Abstract

The present invention provides 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 a main material of a light-emitting layer or a doping material of a light-emitting layer or an electron transport material of an OLED light-emitting device. The obtained organic electroluminescent device has a lower driving voltage and a higher current efficiency.

Description

Technical Field

[0001] The invention belongs to the field of electroluminescence, and relates to an organic compound, an organic electroluminescent device and a display device, and in particular 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 smart phones, tablet computers and other fields, and will be further expanded to large-size application fields such as televisions. In the past 30 years of development, people have developed various OLED materials with excellent performance, and through different designs of device structures and optimization of device performance such as life and efficiency, the commercialization process of OLED has been accelerated, making OLED widely used 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 life 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 is in urgent need of developing more types of OLED materials with higher performance. Summary of the invention

[0005] In view of the shortcomings of the prior art, the object of the present invention is to provide an organic compound, an organic electroluminescent device and a display device, in particular, to provide a compound containing a triphenylene group, an electroluminescent device and a display device. The organic compound of the present invention can be used as a main material or a doping material or an electron transport material of an OLED light-emitting device, and the obtained organic electroluminescent device has a lower driving voltage and a higher current efficiency.

[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] wherein Ar1, Ar2, Ar3 and Ar4 are independently selected from substituted or unsubstituted C6-C40 aryl groups, substituted or unsubstituted C5-C40 heteroaryl groups; Ar1, Ar2, Ar3 and Ar4 are each independently present, or wherein Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar4, or Ar3 and Ar4 are bridged to form a ring;

[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, deuterium, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C6-C40 aryl group.

[0012] 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 representing 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 defined range of carbon atom number of other groups has the same meaning by analogy.

[0013] Preferably, the C6 to C40 aromatic group is selected from one or a combination of two or more of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthfluoroenyl, pyrene, perylenyl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthfluoroenyl and benzonaphthofluorenyl.

[0014] Preferably, the C5-C40 heteroaryl group is selected from dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, dibenzodibenzofuranyl, dibenzodibenzothiophenyl, naphthodibenzofuranyl, naphthodibenzothiophenyl, benzonaphthodibenzofuranyl or benzonaphthodibenzothiophenyl.

[0015] In the present invention, the sp2 hybridized carbon atoms in Ar1 and Ar2 are connected by a single bond to form a five-membered nitrogen-containing heterocyclic ring; similarly, Ar1 and Ar3, Ar1 and Ar4, or Ar3 and Ar4 can also be connected by a single bond to form a five-membered nitrogen-containing heterocyclic ring. For example:

[0016] When Ar1 and Ar2 are selected from benzene rings, Ar1 and Ar2 are bridged to form a ring to form the following structure:

[0017]

[0018] When Ar1 is selected from a benzene ring and Ar2 is selected from a biphenyl ring, Ar1 and Ar2 are bridged to form a ring to form the following structure:

[0019]

[0020] The fact that Ar1 and Ar3, Ar1 and Ar4, and Ar3 and Ar4 can be bridged to form a ring can be understood by referring to this.

[0021] Preferably, Ar1 and Ar2 are the same.

[0022] Preferably, Ar1 and Ar2 are different.

[0023] Preferably, Ar1 is selected from phenyl, biphenyl, 9,9-dimethylfluorenyl, phenylnaphthyl, binaphthyl, dimethylbenzofluorenyl, dimethylhydrogenated benzanthryl, terphenyl, 2-phenyl-9,9-dimethylfluorenyl, 1,4-diphenylnaphthyl, naphthyl, anthracenyl, phenanthryl, dimethylanthryl, 9,9-diphenylfluorenyl, spirofluorenyl, fluoranthenyl, triphenylene or tetramethylindenofluorenyl.

[0024] Preferably, Ar2 is selected from phenyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, benzofluorenyl, terphenyl, 2-phenyl-9,9-dimethylfluorenyl, tetramethylindenofluorenyl, fluoranthenyl, triphenylene or dimethylhydrogenated benzanthryl.

[0025] Preferably, at least one of Ar1 and Ar2 is selected from substituted or unsubstituted C5-C40 heteroaryl groups.

[0026] Further preferably, at least one of Ar1 and Ar2 is selected from triphenylene or fluoranthene.

[0027] Preferably, Ar3 and Ar4 are the same.

[0028] Preferably, Ar3 and Ar4 are different.

[0029] Preferably, Ar3 and Ar4 are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl. When the substituent group has a substituent, the substituent is selected from C1-C6 alkyl or C3-C6 cycloalkyl, for example, it can be methyl, ethyl, butyl, pentyl, cyclohexyl, etc.

[0030] Further preferably, the organic compound is as shown in I-1:

[0031]

[0032] Wherein at least one of Ar2, Ar3 and Ar4 is selected from dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, dibenzodibenzofuranyl, dibenzodibenzothiophenyl, naphthodibenzofuranyl, naphthodibenzothiophenyl, benzonaphthodibenzofuranyl or benzonaphthodibenzothiophenyl.

[0033] Preferably, the organic compound is any one of the following compounds:

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049] In the present invention, the synthesis path of the organic compound is as follows:

[0050]

[0051] Wherein X is selected from bromine and iodine.

[0052] Carry out carbon-nitrogen coupling reaction to generate the compound represented by formula (I).

[0053] In another aspect, the present invention provides a hole transport layer, which comprises the organic compound as described above.

[0054] In another aspect, the present invention provides a light-emitting layer, comprising the organic compound as described above.

[0055] In another aspect, the present invention provides an organic electroluminescent device, comprising the organic compound as described above.

[0056] 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 as described above.

[0057] Preferably, the organic thin film layer comprises a hole transport layer, and the hole transport layer comprises the organic compound as described above.

[0058] Preferably, the organic thin film layer comprises a light-emitting layer, and the light-emitting layer comprises the organic compound as described above.

[0059] In the present invention, the organic compound is used as a host material of the light-emitting layer or a doping material of the light-emitting layer.

[0060] In another aspect, the present invention provides a display device, comprising the organic electroluminescent device as described above.

[0061] Compared with the prior art, the present invention has the following beneficial effects:

[0062] The organic compound of the present invention can be used as the main material of the light-emitting layer or the doping material of the light-emitting layer or the hole transport material of the OLED light-emitting device, and the obtained organic electroluminescent device has a lower driving voltage and a higher current efficiency. DETAILED DESCRIPTION

[0063] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0064] Synthesis Example 1 Synthesis of Compound 1:

[0065]

[0066]

[0067] (1) Synthesis of intermediate M-1-1:

[0068] In a 250 ml three-necked flask, under nitrogen protection, add 50 ml toluene, 30 ml ethanol, 15 ml water, and then add 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. Slowly raise the temperature to 60 ° C and react for 4 hours, then raise the temperature to reflux and react for 4 hours, cool, add water to separate, wash the organic layer with water, dry it with magnesium sulfate, filter to remove the magnesium sulfate, and remove the solvent under reduced pressure. The obtained solid is separated by column chromatography and eluted with petroleum ether to obtain 2.7 g of the intermediate shown in M-1-1.

[0069] The intermediate shown in M-1-1 was detected by mass spectrometry. The two peaks with the largest m / z were 382 and 384. The molecular formula of the product was determined to be C 24 H 15 Br.

[0070] (2) Synthesis of Compound 1:

[0071] In a 500 ml three-necked flask, under nitrogen protection, add 200 ml of dry toluene, 3.83 g (0.01 mol) of the compound shown in M-1-1, 4.89 g (0.01 mol) of the compound shown in M-1-2, 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. Heat to reflux for 6 hours, cool, add water to separate, wash the organic layer with water until neutral, dry with magnesium sulfate, filter to remove magnesium sulfate, concentrate to dryness, separate by silica gel column chromatography, and elute with petroleum ether:ethyl acetate = 10:0.5 (volume ratio) to obtain 7.1 g of compound 1.

[0072] The mass spectrometry of compound 1 was performed to determine the m / z of the molecule to be 790.

[0073] Compound 1 was subjected to NMR detection, and the data analysis is as follows: 1H-NMR (Bruker, Switzerland, AvanceⅡ400MHz NMR spectrometer, CDCl3), δ9.56 (m, 1H), δ9.11 (d, 1H), δ8.65 (d, 1H), δ8.41 (m, 1H), δ8.32 (m, 1H), δ8.11 (m, 1H), δ7.79~7.60 (m, 6H), δ7.59~7.33 (m, 19H), δ7.22 (m, 4H), δ7.13 (m, 1H), δ7.09 (m, 4H), δ7.01 (m, 2H).

[0074] Synthesis Example 2 Synthesis of Compound 23:

[0075]

[0076] The synthesis method refers to the synthesis of compound 1 in Example 1, except that the compound represented by M-1-2 is replaced by the compound represented by M-23-2 to obtain compound 23.

[0077] The mass spectrometry of compound 23 was performed to determine the m / z of the molecule to be 906.

[0078] Synthesis Example 3 Synthesis of Compound 37:

[0079]

[0080] The synthesis method refers to the synthesis of compound 1 in Example 1, except that the compound represented by M-1-2 is replaced by the compound represented by M-37-2 to obtain compound 37.

[0081] The mass spectrometry of compound 37 was performed to determine the m / z of the molecule to be 754.

[0082] Synthesis Example 4 Synthesis of Compound 61:

[0083]

[0084] (1) Synthesis of intermediate M-61-1

[0085] In a 250 ml three-necked flask, under nitrogen protection, add 100 ml of dry toluene, 1.4 g (0.015 mol) of aniline, 3.83 g (0.01 mol) of the intermediate shown in M-1-1, 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. Heat to reflux for 8 hours, cool, add water to separate, wash the organic layer twice with 2% hydrochloric acid, wash with water until neutral, dry with magnesium sulfate, filter to remove the magnesium sulfate, concentrate to dryness, and recrystallize with a mixed solvent of ethanol and toluene to obtain 2.7 g of the intermediate shown in formula M-61-1.

[0086] The intermediate represented by formula M-61-1 was subjected to mass spectrometry detection, and the m / z of the molecule was determined to be 395.

[0087] (2) Synthesis of intermediate M-61-2

[0088] A 500 ml three-necked flask was charged with nitrogen and 300 ml of dry toluene, 16.8 g (0.05 mol) of 9,10-dibromoanthracene, 3.95 g (0.01 mol) of the intermediate shown in M-61-1, and 2.6 g (0.022 mol) of N1,N1,N2,N2-tetramethylethane-1,2-diamine ( CAS:110-18-9 ), 0.0575 g (0.0001 mol) Pd(dba)2 (bis(dibenzylideneacetonepalladium), 0.4 g (0.0002 mol) of a toluene solution containing 10% tri-tert-butylphosphine, 1.44 g (0.015 mol) of sodium tert-butoxide, heated to reflux for 8 hours, cooled, separated by adding water, the organic layer was washed with water until neutral, dried over magnesium sulfate, filtered to remove the magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, and eluted with petroleum ether to obtain 0.9 g of the intermediate represented by formula M-61-2.

[0089] The intermediate shown in formula M-61-2 was detected by mass spectrometry. The two peaks with the largest m / z were 649 and 651. The molecular formula of the product was determined to be C 44 H 28 BrN.

[0090] (3) Synthesis of Compound 61

[0091] The synthesis method refers to the synthesis of compound 1 in Example 1, except that the corresponding bromide and amine compounds are used to obtain compound 61.

[0092] Compound 61 was detected by mass spectrometry, and the m / z of the molecule was determined to be 814.

[0093] Compound 61 was subjected to NMR detection, and the data analysis was as follows: 1H-NMR (Bruker, Switzerland, AvanceⅡ400MHz NMR spectrometer, CDCl3), δ9.58 (m, 1H), δ9.11 (d, 1H), δ9.03 (d, 1H), δ8.42 (m, 1H), δ8.32 (m, 1H), δ8.18~8.08 (m, 5H), δ7.78~7.60 (m, 6H), δ7.57~7.45 (m, 10H), δ7.44~7.34 (m, 5H), δ7.26 (m, 4H), δ7.16 (m, 1H), δ7.11 (m, 4H), δ7.02 (m, 2H).

[0094] Synthesis Example 5 Synthesis of Compound 77:

[0095]

[0096] (1) Synthesis of intermediate M-77-1

[0097] The synthesis method refers to the synthesis of intermediate M-61-1 in Example 4, except that the corresponding bromide and amine compounds are used to obtain intermediate M-77-1.

[0098] The intermediate M-77-1 was subjected to mass spectrometry and the m / z of the molecule was determined to be 485.

[0099] (2) Synthesis of intermediate M-77-2

[0100] The synthesis method refers to the synthesis of intermediate M-61-2 in Example 4, except that the corresponding bromide and amine compounds are used to obtain intermediate M-77-2.

[0101] The intermediate shown in formula M-77-2 was detected by mass spectrometry. The two peaks with the largest m / z were 739 and 741. The molecular formula of the product was determined to be C 50 H 30 BrNO.

[0102] (3) Synthesis of Compound 77

[0103] The synthesis method refers to the synthesis of compound 1 in Example 1, except that the corresponding bromide and amine compounds are used to obtain compound 77.

[0104] Compound 77 was detected by mass spectrometry, and the m / z of the molecule was determined to be 856.

[0105] Synthesis Example 6 Synthesis of Compound 125:

[0106]

[0107] (1) Synthesis of intermediate M-45-1:

[0108] Referring to the synthesis of intermediate M-1-1, except that 3-bromo-4-iodotoluene was used instead of o-dibromobenzene, the reaction conditions were 60°C for 8 hours to obtain intermediate M-45-1.

[0109] The intermediate shown in formula M-45-1 was subjected to mass spectrometry detection. The two peaks with the largest m / z were 396 and 398. The molecular formula of the product was determined to be: C 25 H 17 Br.

[0110] (2) Synthesis of Compound 125:

[0111] Referring to the synthesis of compound 1, compound 125 was obtained by using the corresponding bromide and diarylamine.

[0112] The mass spectrometry of compound 125 was performed to determine the m / z of the molecule to be 804.

[0113] Synthesis Example 7 Synthesis of Compound 253:

[0114]

[0115] Referring to the synthesis of compound 1, compound 253 was obtained by using the corresponding bromide and amine compounds.

[0116] The mass spectrometry of compound 253 was performed to determine the m / z of the molecule to be 790.

[0117] Synthesis Example 8 Synthesis of Compound 149:

[0118]

[0119] Referring to the synthesis of compound 1, compound 149 was obtained by using the corresponding bromide and amine compounds.

[0120] The mass spectrometry of compound 149 was performed to determine the m / z of the molecule to be 828.

[0121] Synthesis Example 9 Synthesis of Compound 150:

[0122]

[0123] Referring to the synthesis of compound 1, compound 150 was obtained by using the corresponding bromide and amine compounds.

[0124] The mass spectrometry of compound 150 was performed to determine the m / z of the molecule to be 788.

[0125] Synthesis Example 10 Synthesis of Compound 213:

[0126]

[0127] Referring to the synthesis of compound 1, compound 213 was obtained by using the corresponding bromide and amine compounds.

[0128] The mass spectrometry of compound 213 was performed to determine the m / z of the molecule to be 752.

[0129] Synthesis Example 11 Synthesis of Compound 225:

[0130]

[0131] Referring to the synthesis of compound 1, compound 225 was obtained by replacing the intermediate represented by M-1-2 with the intermediate represented by M-225-1.

[0132] The mass spectrometry of compound 225 was performed to determine the m / z of the molecule to be 710.

[0133] Synthesis Example 12 Synthesis of Compound 230:

[0134]

[0135] Referring to the synthesis of compound 1, compound 230 was obtained by using the corresponding bromide and amine compounds.

[0136] The mass spectrometry of compound 230 was performed to determine the m / z of the molecule to be 712.

[0137] Synthesis Example 13 Synthesis of Compound 237:

[0138]

[0139] Referring to the synthesis of compound 1, compound 237 was obtained by using the corresponding bromide and amine compounds.

[0140] The compound 237 was detected by mass spectrometry, and the m / z of the molecule was determined to be 712.

[0141] The materials used in the following device examples and comparative examples are as follows:

[0142]

[0143]

[0144] Device Examples 1-20 and Comparative Examples 1-4

[0145] The examples use the compounds of the present application as hole transport materials in organic electroluminescent devices, and the comparative examples use HT-1 to H-4 as hole transport materials in organic electroluminescent devices.

[0146] The structure of the organic electroluminescent device is: ITO / HIL02 (80nm) / hole transport material (35nm) / EM1 (30nm) / TPBI (30nm) / LiF (0.5nm) / Al (150nm).

[0147] The preparation process of organic electroluminescent device is as follows:

[0148] The glass substrate coated with an ITO transparent conductive layer (as an anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, baked in a clean environment until the water is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the properties of the surface and enhance the binding ability with the hole injection layer;

[0149] 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 evaporation film thickness is 80nm;

[0150] The compound of the present application or the comparative material is vacuum-deposited on the hole injection layer as a hole transport layer, the deposition rate is 0.01 nm / s, and the deposition film thickness is 35 nm;

[0151] Vacuum evaporate EM1 on the hole transport layer as the organic light-emitting layer of the device, the evaporation rate is 0.01nm / s, and the total evaporation film thickness is 30nm;

[0152] Vacuum evaporation of TPBI on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device; the evaporation rate is 0.01nm / s, and the total evaporation film thickness is 30nm;

[0153] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer to serve as an electron injection layer and a cathode.

[0154] The devices obtained from the above device embodiments and comparative examples were characterized in terms of brightness, driving voltage, and current efficiency, and tested using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang.

[0155] The performance of the organic electroluminescent device is shown in Table 1 below.

[0156] Table 1

[0157] Hole transport materials <![CDATA[Required luminance cd / m 2 > Drive voltage V Current efficiency cd / A Device Comparison Example 1 HT-1 1000 5.22 1.38 Device Comparison Example 2 HT-2 1000 5.38 1.33 Device Comparison Example 3 HT-3 1000 5.29 1.59 Device Comparison Example 4 HT-4 1000 4.62 1.01 Device Example 1 Compound 1 1000 4.66 1.68 Device Example 2 Compound 2 1000 4.49 1.77 Device Example 3 Compound 8 1000 4.59 1.81 Device Example 4 Compound 23 1000 4.56 1.68 Device Example 5 Compound 25 1000 4.48 1.58 Device Example 6 Compound 37 1000 4.44 1.19 Device Example 7 Compound 49 1000 4.07 1.9 Device Example 8 Compound 101 1000 4.42 2 Device Example 9 Compound 102 1000 4.58 1.7 Device Example 10 Compound 110 1000 4.62 1.77 Device Example 11 Compound 125 1000 4.85 1.62 Device Example 12 Compound 189 1000 4.46 1.66 Device Example 13 Compound 209 1000 4.24 1.51 Device Example 14 Compound 253 1000 4.15 1.6 Device Example 15 Compound 149 1000 4.49 1.63 Device Example 16 Compound 150 1000 4.25 1.81 Device Example 17 Compound 213 1000 4.34 1.34 Device Example 18 Compound 230 1000 4.28 1.77 Device Example 19 Compound 237 1000 4.58 1.64 Device Example 20 Compound 245 1000 4.5 1.39

[0158] It can be seen from Table 1 that, compared with the comparative example, the driving voltage of the organic electroluminescent device prepared using the compounds of the examples of the present application is significantly reduced (as low as below 4.85 V) and the current efficiency is significantly improved (as high as 1.19 cd / A or more, and even as high as 1.68 cd / A or more).

[0159] Device Examples 21-25 and Device Comparative Example 5

[0160] The example uses the compound of the present application as the doping material (dye) of the light-emitting layer in the organic electroluminescent device, and the comparative example uses GD-1 as the doping material of the light-emitting layer in the organic electroluminescent device.

[0161] The structure of the organic electroluminescent device is: ITO / HIL02 (80 nm) / NPB (40 nm) / EM1 (30 nm): doping material 6% / TPBI (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0162] The preparation process of organic electroluminescent device is as follows:

[0163] The glass substrate coated with an ITO transparent conductive layer (as an anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, baked in a clean environment until the water is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the properties of the surface and enhance the binding ability with the hole injection layer;

[0164] 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 evaporation film thickness is 80nm;

[0165] NPB was vacuum evaporated on the hole injection layer as a hole transport layer, with an evaporation rate of 0.01 nm / s and an evaporation film thickness of 40 nm;

[0166] A light layer was vacuum evaporated on the hole transport layer, the evaporation rate was 0.01 nm / s, the total evaporation film thickness was 30 nm, the main material of the light-emitting layer was EM1, and the doping materials were the compound of the present invention and the comparative material GD-1, 6% refers to the doping ratio of the doping material, that is, the volume ratio of the main material of the light-emitting layer to the doping material was 100:6;

[0167] Vacuum evaporation of TPBI on the organic light-emitting layer as the electron transport layer of the organic electroluminescent device; the evaporation rate is 0.01nm / s, and the total evaporation film thickness is 30nm;

[0168] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer to serve as an electron injection layer and a cathode.

[0169] The brightness, driving voltage and current efficiency of the prepared organic electroluminescent devices were also measured using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang in the same way.

[0170] The performance of the organic electroluminescent device is shown in Table 2 below.

[0171] Table 2

[0172]

[0173] It can be seen from the data in Table 2 that, compared with the comparative example, the driving voltage of the organic electroluminescent device prepared using the compounds of the examples of the present application is significantly reduced (as low as below 4.21 V) and the current efficiency is significantly improved (as high as above 6.88 V).

[0174] Device Examples 26-30 and Comparative Examples 6-7

[0175] The examples use the compounds of the present application as the red light host materials in the organic electroluminescent device, and the comparative examples use GH-1 and GH-2 as the red light host materials in the organic electroluminescent device.

[0176] The structure of the organic electroluminescent device is: ITO / HIL02 (50nm) / NPB (20nm) / red light host material (35nm): Ir (piq) 3 [10%] / TPBI (10nm) / Alq3 (15nm) / LiF (0.5nm) / Al (150nm). "Ir (piq) 3 [10%]" refers to the doping ratio of the red light dye, that is, the volume ratio of the red light host material to Ir (piq) 3 is 100:10.

[0177] The organic electroluminescent device was prepared as follows: a glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0178] Place the glass substrate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -4 Pa, vacuum evaporating a hole injection layer HIL02 on the above anode layer film, the evaporation rate is 0.01nm / s, and the evaporation film thickness is 50nm;

[0179] A hole transport layer NPB is vacuum-deposited on the hole injection layer at a rate of 0.01 nm / s and a thickness of 20 nm;

[0180] Vacuum evaporate the red light host material and dye Ir(piq)3 on the hole transport layer as the light-emitting layer of the organic electroluminescent device, the evaporation rate is 0.01nm / s, and the total evaporation film thickness is 35nm;

[0181] The electron transport layer TPBI and Alq3 were vacuum-deposited on the light-emitting layer in sequence, with the evaporation rate of both being 0.01 nm / s and the thickness of the evaporated films being 10 nm and 15 nm respectively;

[0182] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer as the electron injection layer and cathode.

[0183] All organic electroluminescent devices are prepared by the above method, and the only difference is the selection of green light host materials, as shown in Table 3 below.

[0184] Performance Test:

[0185] The brightness, driving voltage and current efficiency of the prepared organic electroluminescent device were measured using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang. The test results are shown in Table 3 below.

[0186] Table 3

[0187] Red light main material <![CDATA[Required luminance cd / m 2 > Drive voltage V Current efficiency cd / A Device Comparative Example 6 GH-1 1000 5.01 39.93 Device Comparison Example 7 GH-2 1000 5.13 31.02 Device Example 26 225 1000 4.29 50.12 Device Example 27 228 1000 4.32 51.55 Device Example 28 237 1000 4.36 43.29 Device Example 29 245 1000 4.67 40.18 Device Example 30 248 1000 4.98 45.26

[0188] It can be seen from the above table that compared with the comparative compounds, the compounds provided in the present application as red light host materials of organic electroluminescent devices can improve the luminous efficiency to more than 40 cd / A and reduce the driving voltage to below 4.98 V.

[0189] Device Examples 31-32 and Comparative Examples 8-9

[0190] The examples use the compounds of the present application as the blue light host materials in the organic electroluminescent device, and the comparative examples use GH-1 and GH-2 as the blue light host materials in the organic electroluminescent device.

[0191] The structure of the organic electroluminescent device is: ITO / HIL02 (50nm) / NPB (20nm) / blue light host material (35nm): Firpic [8%] / TPBI (10nm) / Alq3 (15nm) / LiF (0.5nm) / Al (150nm). "Firpic [8%]" refers to the doping ratio of the blue light dye, that is, the volume ratio of the blue light host material to Firpic is 100:8.

[0192] The organic electroluminescent device was prepared as follows: a glass plate coated with an ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0193] Place the glass substrate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -4 Pa, vacuum evaporating a hole injection layer HIL02 on the above anode layer film, the evaporation rate is 0.01nm / s, and the evaporation film thickness is 50nm;

[0194] A hole transport layer NPB is vacuum-deposited on the hole injection layer at a rate of 0.01 nm / s and a thickness of 20 nm;

[0195] The blue light host material and the dye Firpic are vacuum-deposited on the hole transport layer as the light-emitting layer of the organic electroluminescent device, with a deposition rate of 0.01 nm / s and a total deposition film thickness of 35 nm;

[0196] The electron transport layer TPBI and Alq3 were vacuum-deposited on the light-emitting layer in sequence, with the evaporation rate of both being 0.01 nm / s and the thickness of the evaporated films being 10 nm and 15 nm respectively;

[0197] 0.5 nm of LiF and 150 nm of Al were vacuum-deposited on the electron transport layer as the electron injection layer and cathode.

[0198] All organic electroluminescent devices are prepared by the above method, and the only difference is the selection of blue light host materials, as shown in Table 4 below.

[0199] Performance Test:

[0200] The brightness, driving voltage and current efficiency of the prepared organic electroluminescent device were measured using the OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang. The test results are shown in Table 4 below.

[0201] Table 4

[0202] Blu-ray main material <![CDATA[Required brightness cd / m 2 > Drive voltage V Current efficiency cd / A Device Comparison Example 8 GH-1 1000 6.31 10.45 Device Comparative Example 9 GH-2 1000 7.22 8.11 Device Example 31 225 1000 5.67 13.34 Device Example 32 228 1000 5.89 16.21

[0203] It can be seen from the above table that compared with the comparative compounds, the compounds provided in the present application as blue light host materials of organic electroluminescent devices can improve the luminous efficiency to above 13cd / A and reduce the driving voltage to below 5.89V.

[0204] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the organic compound, organic electroluminescent device and display device of the present invention, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, 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 a structure shown in Formula I: wherein Ar2 is selected from phenyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, benzofluorenyl, terphenyl, 2-phenyl-9,9-dimethylfluorenyl, tetramethylindenofluorenyl, fluoranthene, triphenylene, dimethylhydrogenated benzanthryl, dibenzodibenzofuranyl, dibenzodibenzothiophenyl, naphthodibenzofuranyl, naphthodibenzothiophenyl, benzonaphthodibenzofuranyl or benzonaphthodibenzothiophenyl; Ar1 is selected from C6-C40 arylene, C5-C40 heteroarylene, 9,9-dimethylfluorenyl, dimethylbenzofluorenyl, dimethylhydrobenzanthryl, 2-phenyl-9,9-dimethylfluorenyl, dimethylanthryl, tetramethylindenofluorenyl; The C6-C40 arylene group is selected from phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylene, spirofluorenyl, triphenylene, fluoranthenyl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthofluorenyl, phenylene naphthyl, binaphthyl, 1,4-diphenylnaphthyl, 9,9-diphenylfluorenyl, benzonaphthofluorenyl, or a combination of two or more groups; The C5-C40 heteroarylene group is selected from dibenzofuranylene, dibenzothiophenylene, benzodibenzofuranylene, benzodibenzothiophenylene, dibenzodibenzofuranylene, dibenzodibenzothiophenylene, naphthodibenzofuranylene, naphthodibenzothiophenylene, benzonaphthodibenzofuranylene or benzonaphthodibenzothiophenylene; Ar3 and Ar4 are independently selected from C6-C40 aryl, C5-C40 heteroaryl, 9,9-dimethylfluorenyl; Ar1, Ar2, Ar3 and Ar4 are each independently present, or Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar4, or Ar3 and Ar4 are bridged to form a ring; The C6-C40 aryl group is selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthfluoroenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthfluoroenyl, benzonaphthfluoroenyl, or a combination of two or more thereof; The C5-C40 heteroaryl group is selected from dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, dibenzodibenzofuranyl, dibenzodibenzothiophenyl, naphthodibenzofuranyl, naphthodibenzothiophenyl, benzonaphthodibenzofuranyl or benzonaphthodibenzothiophenyl; R1, R2, R3 and R4 are independently selected from H, F, CN, deuterium, C1-C6 alkyl, C1-C6 alkoxy, C6-C15 aryl.

2. The organic compound according to claim 1, characterized in that The SP2 hybridized carbon atoms in Ar1 and Ar2, or the SP2 hybridized carbon atoms in Ar1 and Ar3, or the SP2 hybridized carbon atoms in Ar1 and Ar4, or the SP2 hybridized carbon atoms in Ar3 and Ar4 are connected by a single bond to form a five-membered nitrogen-containing heterocyclic ring.

3. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are the same.

4. The organic compound according to claim 1, characterized in that Ar1 and Ar2 are not the same.

5. The organic compound according to claim 1, characterized in that Ar1 is selected from phenylene, biphenylene, 9,9-dimethylfluorenylene, phenylene naphthyl, binaphthylene, dimethylbenzofluorenylene, dimethylhydrobenzanthrylene, terphenylene, 2-phenyl-9,9-dimethylfluorenylene, 1,4-diphenylnaphthylene, naphthylene, anthracenylene, phenanthrenylene, dimethylanthrylene, 9,9-diphenylfluorenylene, spirofluorenylene, fluoranthenylene, triphenylene or tetramethylindenofluorenylene.

6. The organic compound according to claim 1, characterized in that Ar1 is selected from a triphenylene group or a fluoranthenylene group.

7. The organic compound according to claim 1, characterized in that Ar2 is selected from triphenylene or fluoranthenyl.

8. The organic compound according to claim 1, characterized in that Ar1 is selected from a triphenylene group or a fluoranthenylene group, and Ar2 is selected from a triphenylene group or a fluoranthenyl group.

9. The organic compound according to claim 1, characterized in that Ar3 and Ar4 are the same.

10. The organic compound according to claim 1, characterized in that Ar3 and Ar4 are not the same.

11. The organic compound according to claim 1, characterized in that Ar3 and Ar4 are independently selected from phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, terphenyl, dibenzofuranyl or dibenzothiophenyl.

12. The organic compound according to claim 1, characterized in that The organic compound is shown in I-1: Wherein at least one of Ar2, Ar3 and Ar4 is selected from dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, dibenzodibenzofuranyl, dibenzodibenzothiophenyl, naphthodibenzofuranyl, naphthodibenzothiophenyl, benzonaphthodibenzofuranyl or benzonaphthodibenzothiophenyl.

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

14. A hole transport layer, characterized in that: The hole transport layer comprises the organic compound according to any one of claims 1 to 13.

15. A light-emitting layer, characterized in that: The light-emitting layer comprises the organic compound according to any one of claims 1 to 13.

16. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the organic compound according to any one of claims 1 to 13.

17. The organic electroluminescent device according to claim 16, 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, wherein the organic thin film layer comprises the organic compound according to any one of claims 1 to 13.

18. The organic electroluminescent device according to claim 17, characterized in that: The organic thin film layer comprises a hole transport layer, and the hole transport layer comprises the organic compound according to any one of claims 1 to 13.

19. The organic electroluminescent device according to claim 17, characterized in that: The organic thin film layer comprises a light-emitting layer, and the light-emitting layer comprises the organic compound according to any one of claims 1 to 13.

20. The organic electroluminescent device according to claim 16, characterized in that: The organic compound is used as a main material of the light-emitting layer or a doping material of the light-emitting layer.

21. A display device, characterized in that: The display device comprises the organic electroluminescent device according to any one of claims 16 to 20.

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