Organic compound and organic electroluminescent device

Abstract

The invention belongs to the technical field of organic compounds, and particularly relates to an organic compound and an organic electroluminescent device. The structural general formula of the organic compound is as shown in formula (I): # imgabs0. The organic compound has the characteristic of high electron mobility, and is beneficial to reducing the power consumption of a device.

Description

Technical Field

[0001] The present application belongs to the technical field of organic compounds, and in particular relates to an organic compound and an organic electroluminescent device. Background Art

[0002] Organic light emitting diodes (OLEDs) have the advantages of self-luminescence, wide viewing angle, high contrast, fast response speed, and the ability to prepare flexible devices. Therefore, they are widely used in the display and lighting industries.

[0003] As OLED technology continues to advance in the fields of lighting and display, people are putting forward higher requirements on the performance of OLED devices, requiring low power consumption, high efficiency and long life. However, the mobility of N-type charge generation layer materials used in existing organic electroluminescent devices is relatively low, resulting in the need for improvement in OLED power consumption, efficiency and life.

[0004] Therefore, there is an urgent need to provide a new organic compound or organic electroluminescent device to solve the electron mobility of OLED devices, thereby solving the problem of device power consumption. Summary of the invention

[0005] The present application aims to solve at least one of the technical problems existing in the above-mentioned prior art. To this end, the present application proposes an organic compound and an organic electroluminescent device.

[0006] A first aspect of the present application provides an organic compound.

[0007] In some embodiments, an organic compound has a general structural formula as shown in formula (I):

[0008]

[0009] Wherein, L1-L3 are independently selected from a single bond, an R-substituted or unsubstituted arylene group having 6 to 60 ring carbon atoms, and an R-substituted or unsubstituted heteroarylene group having 2 to 60 ring carbon atoms;

[0010] Ar1-Ar3 are independently selected from hydrogen, deuterium, R substituted or unsubstituted C6 to C60 aryl, R substituted or unsubstituted C3 to C60 heteroaryl, R substituted or unsubstituted C6-C30 arylphosphinoyl;

[0011] The R is selected from at least one of a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a deuterium group, a cyano group, a nitro group, a hydrazine group, a sulfonic acid group, a C1 to C20 alkylsilyl group, a C1 to C20 alkoxysilyl group, a C3 to C30 cycloalkylsilyl group, a C6 to C30 arylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a C1 to C20 alkylamino group, and an unsubstituted amine group;

[0012] The substitution in R is substituted by at least one of halogen, C1-C4 alkyl, deuterium, C6 to C30 aryl or C3 to C30 heteroaryl;

[0013] m1-m3 are independently selected from integers from 0 to 3;

[0014] X is an oxygen group element;

[0015] The organic compound is not

[0016] Wherein, Q includes a straight chain or branched alkylene, a C1 to C8 alkyl-substituted arylene or a C1 to C8 alkyl-substituted heteroarylene, A is hydrogen, alkyl, amino, carboxyl, halogen, acyl, NR1R2, R1 and R2 are independently selected from phenyl substituted by an alkyl group, and X' represents an oxygen atom or a sulfur atom.

[0017] In some embodiments, the heteroatom in the heteroarylene group and the heteroaryl group is an oxygen or nitrogen element.

[0018] In some embodiments, the heteroatom in the heteroarylene group and the heteroaryl group is at least one of N, O and S.

[0019] In some embodiments, L1-L3 are independently selected from a single bond, an R-substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, and an R-substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms.

[0020] In some embodiments, L1-L3 are independently selected from a single bond, an R-substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, and an R-substituted or unsubstituted heteroarylene group having 5 to 23 ring carbon atoms.

[0021] In some embodiments, Ar1-Ar3 are independently selected from R substituted or unsubstituted C6 to C30 aryl, R substituted or unsubstituted C3 to C30 heteroaryl, and R substituted or unsubstituted C6-C20 arylphosphinoyl.

[0022] In some embodiments, Ar1-Ar3 are independently selected from R substituted or unsubstituted C6 to C20 aryl, R substituted or unsubstituted C3 to C26 heteroaryl, and R substituted or unsubstituted C6-C18 arylphosphinoyl.

[0023] In some embodiments, Ar1-Ar3 are independently selected from hydrogen, C6 to C18 aryl, C5 to C26 heteroaryl, C6-C18 arylphosphinoyl.

[0024] In some embodiments, m1-m3 are independently selected from 0 or 1.

[0025] In some embodiments, R is selected from at least one of substituted or unsubstituted C1 to C15 alkyl, substituted or unsubstituted C1 to C15 alkoxy, deuterium, cyano, nitro, hydrazine, sulfonic acid, C1 to C15 alkylsilyl, C1 to C15 alkoxysilyl, C3 to C20 cycloalkylsilyl, C6 to C20 arylsilyl, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C15 alkylamine and unsubstituted amine;

[0026] In some embodiments, R is selected from at least one of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a deuterium group, a cyano group, a nitro group, a hydrazine group, a sulfonic acid group, a C1 to C10 alkylsilyl group, a C1 to C10 alkoxysilyl group, a C3 to C10 cycloalkylsilyl group, a C6 to C10 arylsilyl group, a substituted or unsubstituted C6 to C10 aryl group, a substituted or unsubstituted C3 to C10 heteroaryl group, a C1 to C10 alkylamine group, and an unsubstituted amine group;

[0027] In some embodiments, the substitution in R is substituted by at least one of halogen, C1-C4 alkyl, and deuterium.

[0028] In some embodiments, formula (I) is represented by the following formula (II):

[0029]

[0030] In formula (II), L1, Ar1-Ar3 and X are the same as defined in formula (I).

[0031] In some embodiments, L1-L3 is a single bond or at least one of the following structures:

[0032]

[0033]

[0034] In some embodiments, Ar1-Ar3 are independently selected from R substituted or unsubstituted C6 to C20 aryl, R substituted or unsubstituted C3 to C20 heteroaryl, R substituted or unsubstituted C6 to C20 arylphosphinoyl, wherein R is selected from at least one of substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkoxy, halogen, cyano, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C20 alkylamine and unsubstituted amine.

[0035] In some embodiments, the heteroaryl group is a group containing one or more SP 2 Hybridized nitrogen atoms.

[0036] In some embodiments, Ar1-Ar3 are independently selected from at least one of the following structures.

[0037] When Ar1-Ar3 are independently selected from two or more groups in the following structures, the two or more groups can be formed by bonding, and the bonding method can be single bonded or condensed as long as it does not violate the group connection rules. In some embodiments, multiple groups are connected by single bonds. Ar1, Ar2, and Ar3 can be the same or different from each other.

[0038]

[0039]

[0040] In some embodiments, the structure of the organic compound described in the present application is one of the following structural formulas:

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] A second aspect of the present application provides an organic electroluminescent device.

[0047] There are many forms of organic electroluminescent devices, and the organic electroluminescent devices are divided into upright structures and inverted structures. The organic electroluminescent device of the upright structure includes a substrate, an anode, a light-emitting structure, and a cathode stacked from bottom to top. The organic electroluminescent device of the inverted structure may include a substrate, a cathode, a light-emitting structure, and an anode stacked from bottom to top.

[0048] In some embodiments, the light emitting structure may include a plurality of light emitting units arranged in a stacked manner.

[0049] In some embodiments, an organic electroluminescent device comprises:

[0050] anode;

[0051] a first light emitting stack disposed on the anode;

[0052] a charge generation layer disposed on the first light-emitting stack, the charge generation layer comprising the organic compound;

[0053] a second light emitting stack disposed on the charge generation layer;

[0054] and a cathode disposed on the second light emitting stack.

[0055] In some embodiments, the charge generation layer includes an N-type charge generation layer and a P-type charge generation layer that are stacked, and the organic compound is located in the N-type charge generation layer.

[0056] In some embodiments, the first light-emitting stack includes a first hole transport layer, a first light-emitting layer, and a first electron transport layer arranged in a stacked manner, and the first hole transport layer is close to the anode; the second light-emitting stack includes a second hole transport layer, a second light-emitting layer, and a second electron transport layer arranged in a stacked manner, and the second hole transport layer is close to the first electron transport layer. In this embodiment, the N-type charge generation layer in the charge generation layer is close to the first electron transport layer.

[0057] In some embodiments, at least one of the first electron transport layer, the second electron transport layer, and the charge generation layer includes the organic compound.

[0058] In some embodiments, a first hole injection layer is further disposed between the anode and the first hole transport layer.

[0059] In some embodiments, a first electron blocking layer is further disposed between the first hole transport layer and the first light-emitting layer.

[0060] In some embodiments, a second electron blocking layer is further disposed between the second hole transport layer and the second light-emitting layer.

[0061] In some embodiments, a second electron injection layer is further disposed between the second electron transport layer and the cathode.

[0062] In some embodiments, the N-type charge generation layer further comprises at least one of a lanthanide metal, a transition metal, an alkali metal, or an alkaline earth metal.

[0063] A display or lighting element comprises the above organic electroluminescent device.

[0064] Compared with the prior art, the beneficial effects of this application are as follows:

[0065] The organic compound described in the present application is an organic compound of a phenanthroline derivative, which has the characteristics of high electron mobility and is beneficial to reducing the power consumption and voltage of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0066] Figure 1 Schematic diagram of the structure of the organic electroluminescent device in the embodiment of the present application. DETAILED DESCRIPTION

[0067] In order to make the technical solution described in this application more clearly understood by those skilled in the art, the following examples are listed for illustration. It should be noted that the following examples do not limit the scope of protection claimed in this application.

[0068] In the description of the present application, it should be understood that the orientation or positional relationship indicated by the terms "upper" and "lower" and the like is based on the orientation or positional relationship shown in the accompanying drawings, and is only for the convenience of describing the present application and simplifying the description, rather than indicating or implying that the device or element referred to must have a specific orientation, be constructed and operated in a specific orientation, and therefore cannot be understood as a limitation on the present application. In addition, the terms "first" and "second" are used for descriptive purposes only, and cannot be understood as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Therefore, the features defined as "first" and "second" may explicitly or implicitly include one or more of the said features.

[0069] In the present application, unless otherwise clearly specified and limited, a first feature being "above" or "below" a second feature may include that the first and second features are in direct contact, or may include that the first and second features are not in direct contact but are in contact through another feature between them. Moreover, a first feature being "above" a second feature includes that the first feature is directly above and obliquely above the second feature, or simply means that the first feature is higher in level than the second feature. A first feature being "below" a second feature includes that the first feature is directly below and obliquely below the second feature, or simply means that the first feature is lower in level than the second feature.

[0070] In the present application, "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, for example, aryl is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, tetraphenyl, pyrene, perylene, The invention may be substituted with any of the following: 1) a benzo[c]phenanthrenyl group, 2) a benzo[g]chrysene group, 3) a fluorenyl group, 4) a spirobifluorenyl group, 5) a benzofluorenyl group, 6) a dibenzofluorenyl group, 7) a biphenyl group, 8) a terphenyl group, 9) a quaterphenyl group or 10) a fluoranthene group.

[0071] "Heteroaryl" refers to a monovalent group in which at least one carbon atom based on an aromatic group is replaced by a non-carbon atom, wherein the non-carbon atom can be selected from a heterocyclic aromatic system of O, S, N, P, B, Se, Si or Ge, but does not include the case where the aromatic group is connected to the main structure through a non-carbon atom group (for example, aryloxy, arylsilyl, arylboryl, arylphosphino, arylamine). For example, the heteroaryl group is selected from pyrrolyl, pyrrolopyrrolyl, furopyrrolyl, thienopyrrolyl, pyridinyl, pyrazolyl, pyrimidinyl, pyrazinyl, triazinyl, pyridazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furofuranyl, azadibenzofuranyl, thienofuranyl, diazadibenzofuranyl, benzo[B]naphtho[1,2-D] furanyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, quinazolinonyl, carbazolyl, azacarbazolyl, diazacarbazolyl, phenanthridinyl, primary pyridinyl, acridinyl, dihydroacridinyl, phenanthrolinyl, oxazolinyl, oxazolyl, oxadiazolyl, benzisoxazolyl, thiazolyl, benzothiazolyl, benzisothiazolyl, pyrroloimidazolyl, furazanyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, diazadibenzothienyl, thienothiphenyl or o-naphthyridinyl.

[0072] The "arylene group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing two hydrogen atoms.

[0073] The "heteroarylene group" refers to a divalent group having the same structure as a heteroaryl group.

[0074] Unless otherwise specified, the raw materials, reagents or devices used in the following examples can be obtained from conventional commercial sources or by existing known methods.

[0075] The synthetic route of organic compound C2 is as follows:

[0076]

[0077] Pour 5 g of reactants C2-1, 9.9 g of K2CO3 and 2.0 g of iodine into a 500 mL three-necked flask, add 150 mL of DMF (dimethylformamide), slowly add 5.6 g of C2-2 dropwise at room temperature, raise the temperature to 63°C, react overnight, wait until the reaction cools to room temperature, then pour into a beaker, add 700 mL of H2O, stir for 30 min, and filter to obtain a crude product; the crude product is separated by column using a mixed solvent of dichloromethane and methanol to obtain 8.0 g of white powder (organic compound C2), with a yield of 65%.

[0078] The hydrogen spectrum data of the white powder (organic compound C2) are as follows:1 H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.64(t,J=1.9Hz,1H),8.59(dd,J=8.6,1.8Hz,1H),8.31 –8.21(m,2H),8.11–8.03(m,2H),7.94–7.87(m,1H),7.62(dd,J=8.5,4.1Hz,1H),7.58–7.46(m,3H).

[0079] According to the synthesis method of organic compound C2, organic compound (C13-1) is used to replace organic compound (C2-2) in the synthesis process of organic compound C2. The other processes are the same as the synthesis process of organic compound C2 to synthesize organic compound (C13). The structural formulas of organic compounds (C13-1) and (C13) are as follows:

[0080]

[0081] The hydrogen spectrum data of organic compounds (C13) are as follows: 1 H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.59(dd,J=8.6,1.8Hz,1H),8.29–8.17(m,6H),8.16–8.11(m,2H),8.07(d,J=8. 0Hz,1H),8.01–7.89(m,2H),7.82–7.76(m,2H),7.72(dd,J=8.0,2.0Hz,1H),7.62(dd,J=8.5,4.1Hz,1H),7.56–7.44(m,7H).

[0082] According to the synthesis method of organic compound C2, organic compound (C19-1) is used to replace organic compound (C2-2) in the synthesis process of organic compound C2. The other processes are the same as the synthesis process of organic compound C2 to synthesize organic compound (C19). The structural formulas of organic compounds (C19-1) and (C19) are as follows:

[0083]

[0084] The hydrogen spectrum data of organic compounds (C19) are as follows: 1H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.78–8.68(m,3H),8.60(m,3H),8.25(dd,J=9.2,2.2Hz,1H),8.18–8. 10(m,2H),7.78(m,2H),7.74–7.68(m,2H),7.62(dd,J=8.5,4.1Hz,1H),7.50(dd,J=9.0,4.0Hz,1H),7.22(m,2H).

[0085] According to the synthesis method of organic compound C2, organic compound (C25-1) is used to replace compound (C2-2) in the synthesis process of organic compound C2. The other processes are the same as the synthesis process of organic compound C2 to synthesize organic compound (C25). The structural formulas of organic compounds (C25-1) and (C25) are as follows:

[0086]

[0087] The hydrogen spectrum data of the organic compound (C25) are as follows: 1 H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.59(dd,J=8.6,1.8Hz,1H),8.29–8.19( m,2H),8.17–8.10(m,2H),8.01–7.93(m,1H),7.89–7.77(m,2H),7.65–7.45(m,6H).

[0088] The synthetic route of organic compound (C27) is as follows:

[0089]

[0090] According to the synthesis method of organic compound C2, organic compound (C27-2) is synthesized by using organic compound (C27-1) to replace organic compound (C2-2) in the synthesis process of organic compound C2.

[0091] The organic compound (C27-2) (5 g) and tetrahydrofuran (500 mL) were added to a 2L three-necked flask, replaced with N2 three times, and the ethanol bath was lowered to below -80°C with liquid nitrogen. n-BuLi (n-butyllithium, 6.9 mL) was added dropwise and maintained below -80°C with stirring for 0.5 h. Diphenylphosphine chloride (3.5 g) was added dropwise for 0.5 h and the temperature was naturally raised to room temperature for reaction for 2 h. 100 mL of ethanol was added to quench, the obtained organic liquid was spin-dried, 3L of dichloromethane was added and stirred, and then washed with water three times. The obtained organic suspension was spin-dried, 1L of dichloromethane was added to the obtained solid, H2O2 (13 g) was added dropwise at room temperature with stirring, and the reaction was continued at room temperature with stirring for 2 h. After the reaction was completed, the organic liquid was directly mixed with a sample and separated by a column purification column to obtain an organic compound (C27) with a yield of 63%.

[0092] The hydrogen spectrum data of organic compounds (C27) are as follows: 1 H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.59(dd,J=8.6,1.8Hz,1H),8.25(dd,J=9.2, 2.2Hz,1H),8.04–7.98(m,2H),7.81–7.77(m,2H),7.70–7.60(m,5H),7.58–7.45(m,7H).

[0093] According to the synthesis method of organic compound C2, organic compound (C44-1) is used to replace compound (C2-2) in the synthesis process of organic compound C2. The other processes are the same as the synthesis process of organic compound C2 to synthesize organic compound (C44). The structural formulas of organic compounds (C44-1) and (C44) are as follows:

[0094]

[0095] The hydrogen spectrum data of the organic compound (C44) are as follows: 1 H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.59

[0096] (dd,J=8.6,1.8Hz,1H),8.25(dd,J=9.2,2.2Hz,1H),8.15–8.07(m,2H),8.01–7.89(m,2H),

[0097] 7.84(dd,J=6.6,1.4Hz,3H),7.67–7.60(m,3H),7.50(dd,J=9.0,4.0Hz,1H),7.41–7.30(m,

[0098] 6H), 7.22 (d, J = 2.0Hz, 1H), 6.83 (m, 3H).

[0099] According to the synthesis method of organic compound C2, organic compound (C50-1) is used to replace compound (C2-2) in the synthesis process of organic compound C2. The other processes are the same as the synthesis process of organic compound C2 to synthesize organic compound (C50). The structural formulas of organic compounds (C50-1) and (C50) are as follows:

[0100]

[0101] The hydrogen spectrum data of organic compounds (C50) are as follows: 1 H NMR(400MHz,Chloroform-d)δ9.05(dd,J=4.0,

[0102] 1.8Hz,1H),8.98(m,2H),8.59(dd,J=8.6,1.8Hz,1H),8.42(dd,J=8.2,1.8Hz,1H),8.28–

[0103] 8.14(m,4H),8.05–7.85(m,5H),7.62m,2H),7.50(dd,J=9.0,4.0Hz,1H).

[0104] According to the synthesis method of organic compound C2, organic compound (C55-1) is used to replace compound (C2-2) in the synthesis process of organic compound C2. The other processes are the same as the synthesis process of organic compound C2 to synthesize organic compound (C55). The structural formulas of organic compounds (C55-1) and (C55) are as follows:

[0105]

[0106] The hydrogen spectrum data of organic compounds (C55) are as follows: 1 H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.77

[0107] –8.55(m,3H),8.29–7.96(m,5H),7.84(dd,J=6.8,1.3Hz,1H),7.67–7.58(m,3H),7.57–

[0108] 7.28(m,8H),6.97(dd,J=7.0,1.6Hz,1H).

[0109] The synthetic route of organic compound (C67) is as follows:

[0110]

[0111] The organic compound (C2-1) (5 g) and Lawesson's reagent (4.8 g) were placed in a 250 mL reaction bottle, 100 mL of tetrahydrofuran was added, the system was evacuated, and the temperature was raised to reflux for reaction for 5 hours under a nitrogen atmosphere. After the reaction, deionized water and dichloromethane were added, the organic phase was extracted and dried, and column separation was performed to obtain 5.8 g of white powder organic compound (C67) with a yield of 68%.

[0112] According to the synthesis method of organic compound C2, organic compound (C67-1) is used to replace compound (C2-1) in the synthesis process of organic compound C2, and other processes are the same as the synthesis process of organic compound C2 to synthesize organic compound (C67).

[0113] The hydrogen spectrum data of organic compounds (C67) are as follows: 1 H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.66

[0114] (dd,J=8.4,1.8Hz,1H),8.45–8.31(m,2H),8.05–7.87(m,4H),7.64(dd,J=8.5,4.1Hz,1H),7.57–7.47(m,3H).

[0115] According to the synthesis method of organic compound (C67), compound (C19-1) is used to replace compound (C2-2) in the synthesis process of organic compound (C67), and the other steps are the same as the synthesis process of organic compound C67, to synthesize organic compound (C84);

[0116]

[0117] The hydrogen spectrum data of organic compounds (C84) are as follows: 1 H NMR(400MHz,Chloroform-d)δ8.98(m,2H),8.79–8.59(m,7H),8.41(dd,J=7.3,2.2Hz,1H),7.9 2–7.85(m,2H),7.81–7.77(m,2H),7.71–7.61(m,3H),7.51(dd,J=7.3,4.0Hz,1H),7.22(m,2H).

[0118] The organic compound of the present application is used to prepare an organic electroluminescent device.

[0119] Figure 1 Schematic diagram of the structure of the organic electroluminescent device in the embodiment of the present application. Figure 1 1 represents an anode, 2 represents a first hole injection layer, 3 represents a first hole transport layer, 4 represents a first electron blocking layer, 5 represents a first light-emitting layer, 6 represents a first electron transport layer, 7 represents an N-type charge generation layer, 8 represents a P-type charge generation layer, 9 represents a second hole transport layer, 10 represents a second electron blocking layer, 11 represents a second light-emitting layer, 12 represents a second electron transport layer, 13 represents a second electron injection layer, and 14 represents a cathode.

[0120] An organic electroluminescent device with a positive structure is used as a specific embodiment. First, a transparent conductive ITO glass substrate (as an anode) is washed with deionized water, ethanol, acetone, and deionized water in sequence, dried at 80°C, treated with oxygen plasma for 30 minutes, and then placed in a vacuum evaporator at a temperature of <4*10 -4 Under the conditions of Pa, the first hole injection layer (20nm HAT-CN), the first hole transport layer (10nm HTL), the first electron blocking layer (5nm EBL), the first light-emitting layer (20nm BH:BD, the mass ratio of BH to BD is 97:3), the first electron transport layer (35nm ET:LiQ, 50%), the N-type charge generation layer (10nm n-CGL), the P-type charge generation layer (10nm HAT-CN), the second hole transport layer (10nm HTL), the second electron blocking layer (5nm EBL), the second light-emitting layer (20nm BH:BD, the mass ratio of BH to BD is 97:3), the second electron transport layer (35nm ET:LiQ, the mass ratio of ET to LiQ is 50:50), the second electron injection layer (1nm Yb), and the cathode (1000nm Ag) are sequentially deposited. Among them, n-CGL is a mixture of the organic compound of the present application and ytterbium, and the mass fraction of ytterbium is 5%.

[0121] The material structure used in the above-mentioned organic electroluminescent device is as follows:

[0122]

[0123] The organic electroluminescent devices of Examples 1-10 and Comparative Examples 1-2 are prepared by the above method, the difference being that the organic compounds of the present application in n-CGL are organic compound C2, organic compound C13, organic compound C19, organic compound C25, organic compound C27, organic compound C44, organic compound C50, organic compound C55, organic compound C67, organic compound C84, comparison compound 1, and comparison compound 2, respectively.

[0124] The above organic electroluminescent device was measured at 10 mA / cm 2 The electrical and optical properties at 50 mA / cm 2The device life under the condition is as shown in Table 1 (the voltage, current efficiency, and T90 life values ​​in Table 1 are expressed in percentages, which are based on the voltage, current efficiency, and T90 life corresponding to Comparative Example 1, and are used to measure the voltage, current efficiency, and T90 life of other embodiments or comparative examples. Taking the voltage of 92%, the current efficiency of 101%, and the T90 life of 130% of Example 1 as an example, it means that the voltage of the organic electroluminescent device of Example 1 under the same test conditions is only 92% of that of Comparative Example 1, the current efficiency is 101%, and the T90 life is 130% of that of Comparative Example 1).

[0125] Table 1

[0126] serial number Voltage (V) Current efficiency (cd / A) T90 life (h) Comparative Example 1 100％ 100％ 100％ Comparative Example 2 95％ 102％ 120％ Example 1 92％ 101％ 130％ Example 2 92％ 101％ 130％ Example 3 90％ 101％ 150％ Example 4 90％ 101％ 130％ Example 5 93％ 102％ 130％ Example 6 90％ 101％ 140％ Example 7 93％ 102％ 130％ Example 8 91％ 102％ 130％ Example 9 92％ 101％ 130％ Example 10 90％ 101％ 150％

[0127] As can be seen from Table 1, the voltage of the organic electroluminescent device prepared by using the organic compound of the present application as a component of n-CGL is significantly lower than that of Comparative Example 1, thereby reducing the power consumption of the device and improving the device life. Compared with Comparative Example 2, the voltage of the device corresponding to the embodiment is also lower.

Claims

1. An organic compound, characterized in that Its general structural formula is shown in formula (I): Wherein, L1-L3 are independently selected from a single bond, an R-substituted or unsubstituted arylene group having 6 to 60 ring carbon atoms, and an R-substituted or unsubstituted heteroarylene group having 2 to 60 ring carbon atoms; Ar1-Ar3 are independently selected from hydrogen, deuterium, R substituted or unsubstituted C6 to C60 aryl, R substituted or unsubstituted C3 to C60 heteroaryl, R substituted or unsubstituted C6-C30 arylphosphinoyl; The R is selected from at least one of a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a deuterium group, a cyano group, a nitro group, a hydrazine group, a sulfonic acid group, a C1 to C20 alkylsilyl group, a C1 to C20 alkoxysilyl group, a C3 to C30 cycloalkylsilyl group, a C6 to C30 arylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a C1 to C20 alkylamino group, and an unsubstituted amine group; The substitution in R is substituted by at least one of halogen, C1-C4 alkyl, deuterium, C6 to C30 aryl or C3 to C30 heteroaryl; m1-m3 are independently selected from integers from 0 to 3; X is an oxygen group element; The organic compound is not Wherein, Q includes a straight chain or branched alkylene, a C1 to C8 alkyl-substituted arylene or a C1 to C8 alkyl-substituted heteroarylene, A is hydrogen, alkyl, amino, carboxyl, halogen, acyl, NR1R2, R1 and R2 are independently selected from phenyl substituted by an alkyl group, and X' represents an oxygen atom or a sulfur atom.

2. The organic compound according to claim 1, characterized in that L1-L3 are independently selected from a single bond, an R-substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, and an R-substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms; and / or, Ar1-Ar3 are independently selected from R substituted or unsubstituted C6 to C30 aryl, R substituted or unsubstituted C3 to C30 heteroaryl, R substituted or unsubstituted C6-C20 arylphosphinoyl; and / or, R is selected from at least one of a substituted or unsubstituted C1 to C15 alkyl group, a substituted or unsubstituted C1 to C15 alkoxy group, a deuterium group, a cyano group, a nitro group, a hydrazine group, a sulfonic acid group, a C1 to C15 alkylsilyl group, a C1 to C15 alkoxysilyl group, a C3 to C20 cycloalkylsilyl group, a C6 to C20 arylsilyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heteroaryl group, a C1 to C15 alkylamino group, and an unsubstituted amine group; And / or, m1-m3 are independently selected from 0 or 1.

3. The organic compound according to claim 1, characterized in that Formula (I) is represented by the following formula (II): In formula (II), L1, Ar1-Ar3 and X are the same as defined in formula (I).

4. The organic compound according to claim 1, characterized in that L1-L3 is a single bond or at least one of the following structures:

5. The organic compound according to claim 1, characterized in that Ar1-Ar3 are independently selected from hydrogen, deuterium, R substituted or unsubstituted C6 to C20 aryl, R substituted or unsubstituted C3 to C20 heteroaryl, R substituted or unsubstituted C6 to C20 arylphosphinoyl, wherein R is selected from at least one of substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkoxy, halogen, cyano, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C20 alkylamine and unsubstituted amine.

6. The organic compound according to claim 1, characterized in that Ar1-Ar3 are independently selected from at least one of the following structures:

7. The organic compound according to claim 1, characterized in that The heteroatom in the heteroarylene group and the heteroaryl group is an oxygen group or a nitrogen group element.

8. The organic compound according to claim 1, characterized in that The structure of the organic compound is one of the following structural formulas:

9. An organic electroluminescent device, characterized in that: It includes: anode; a first light emitting stack disposed on the anode; a charge generation layer disposed on the first light-emitting stack, the charge generation layer comprising the organic compound according to any one of claims 1 to 8; a second light emitting stack disposed on the charge generation layer; and a cathode disposed on the second light emitting stack.

10. The organic electroluminescent device according to claim 9, characterized in that: The charge generation layer comprises an N-type charge generation layer and a P-type charge generation layer which are stacked, and the organic compound is located in the N-type charge generation layer; And / or, the first light-emitting stack includes a first hole transport layer, a first light-emitting layer, and a first electron transport layer that are stacked, and the first hole transport layer is close to the anode; the second light-emitting stack includes a second hole transport layer, a second light-emitting layer, and a second electron transport layer that are stacked, and the second hole transport layer is close to the first electron transport layer.

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