Hole transport material, organic light-emitting device and display or lighting apparatus

Abstract

The present invention relates to the technical field of organic optoelectronic material preparation, and in particular to a hole transport material, an OLED containing the compound, and an organic light-emitting apparatus. The hole transport material uses triphenylamine as a core, with three side chains formed by an aromatic group, an alkyl-substituted fluorenyl group and heteroaryl group, and an ortho-substituted aryl group, enabling the compound to maintain high stability. In addition, when used to fabricate an organic EL element, the material effectively increases the luminous efficiency and operational lifetime of an organic light-emitting device, and has promising application prospects.

Description

A hole transport material, an organic light-emitting device, and a display or illumination device TECHNICAL FIELD

[0001] The present application relates to the technical field of organic optoelectronic material preparation, in particular to a hole transport material, an organic light-emitting device, and a display or illumination device. BACKGROUND

[0002] An organic electroluminescence diode (OLED) is also known as an organic electroluminescence device, which is a technology that converts electrical energy into light energy through an organic light-emitting material by applying a voltage to an organic electroluminescence element to inject holes from an anode and electrons from a cathode into a light-emitting layer, and then recombine the injected holes and electrons to form excitons to cause light emission.

[0003] Generally, the organic material layer has a multi-layer structure composed of different materials to improve the efficiency and stability of the organic light-emitting device, for example, the organic material layer can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. At present, the hole transport material generally has the problems of poor thermal stability, low HOMO value and triplet energy level, and when it is applied to an organic light-emitting device, there are still problems of improving the driving voltage, light-emitting efficiency and working life of the device.

[0004] Therefore, it is necessary to develop an organic optoelectronic material with good stability and excellent light-emitting performance, and to find a suitable OLED optoelectronic functional material for an OLED device to solve the above problems. SUMMARY

[0005] The purpose of the present application is to provide one or more hole transport materials for an organic electroluminescence device. In order to solve the above technical problems, the present application provides a triarylamine hole transport material obtained by combining an ortho-substituted aryl group with a substituted fluorene group, an OLED having the compound, and a display or illumination device. The provided hole transport material has a triarylamine as a mother nucleus, a heteroaryl group, an aromatic group, and an alkyl-substituted fluorene group as three side chains combined with an ortho-substituted aryl group, so that the compound can maintain high stability, and at the same time, the device can have high efficiency.

[0006] The hole transport material provided by the present application is realized by the following technical scheme:

[0007] A hole transport material has a compound with the structure shown in the following formula (I):

[0008] In formula (I), X1independently represents CR a R b , NR c , or O, S atom, R a , Rb , R c each independently selected from the group consisting of C1-C24alkyl, C6-C30aryl, C5-C30heteroaryl; R a , R b may be mutually linked to form a C3-C20cycloalkyl group;

[0009] L1is selected from the group consisting of a single bond, substituted or unsubstituted C6-C30arylene, which can be mono-, di- or maximally possible substituted, and when containing substituents, the substituents can be hydrogen, deuterium, C1-C24alkyl, C3-C20cycloalkyl;

[0010] R1is selected from the group consisting of substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C4-C36heteroaryl, and when containing substituents, the substituents can be C1-C24alkyl, C3-C20cycloalkyl, C6-C30aryl;

[0011] L2, L3are each independently selected from the group consisting of a single bond, C1-C24alkyl, C3-C20cycloalkyl, substituted or unsubstituted C6-C30aryl, and the group consisting of; and when containing substituents, the substituents can be hydrogen, deuterium, C1-C24alkyl, C3-C20cycloalkyl;

[0012] R2, R3are each independently selected from the group consisting of C1-C10alkyl, C6-C30aryl.

[0013] Preferably, the compound of formula (I) can be partially or fully deuterated.

[0014] Preferably, a hole transport material, a compound having a structure as shown in formula (i) or formula (ii):

[0015] In formula (i) or formula (ii), X1independently represents CR a R b , NR c or O, S atom, R a , R b , R c each independently selected from the group consisting of C1-C24alkyl, C6-C30aryl, C5-C30heteroaryl;

[0016] L1is selected from the group consisting of a single bond, substituted or unsubstituted C6-C30arylene, which can be mono-, di- or maximally possible substituted, and when containing substituents, the substituents can be hydrogen, deuterium, C1-C24alkyl, C3-C20cycloalkyl; R1is selected from the group consisting of C6-C30aryl substituted or unsubstituted with C1-C24alkyl, C3-C20cycloalkyl, C6-C30aryl substituted or unsubstituted C4-C36heteroaryl;

[0017] L2, L3 are each independently selected from the group consisting of a single bond, C1-C24 alkyl, C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and when substituted, the substituents are selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl; R2, R3 are each independently selected from the group consisting of C1-C10 alkyl, C6-C30 aryl.

[0018] Preferably, in the formula (I), L2, L3 are each independently selected from the group consisting of a single bond, n-propyl, i-propyl, C3-C6 cycloalkyl, C1-C6 alkyl substituted phenyl; R2, R3 are each independently selected from the group consisting of methyl or phenyl.

[0019] Preferably, the structure of formula (I) can be represented by any one of formula (I-1) to formula (I-2):

[0020] wherein X1, L1, R1 are defined as above in formula I.

[0021] More preferably, the structure of formula (I) can be represented by any one of formula (I-1) to formula (I-2):

[0022] wherein X1, L1, R1 are defined as above in formula I. More preferably, when X1 is represented as CR a R b , R a , R b are each independently selected from the group consisting of methyl, phenyl or R a , R b are each independently selected from the group consisting of methyl, phenyl or R c , R c are each independently selected from the group consisting of methyl, phenyl or R

[0023] Preferably, in the formula (I), L1 is selected from the group consisting of a single bond or C1-C10 alkyl substituted C6-C30 aryl; R1 is independently selected from the group consisting of C6-C30 aryl substituted or unsubstituted by C1-C5 alkyl or C3-C10 cycloalkyl, C4-C36 heteroaryl substituted or unsubstituted by C6-C30 aryl.

[0024] More preferably, L1 is independently selected from the group consisting of a single bond, phenyl, biphenyl, methylphenyl, dimethylphenyl, adamantyl substituted phenyl; R1 is independently selected from the group consisting of phenyl, methylphenyl, dimethylphenyl, phenylcarbazolyl, dibenzofuranyl, adamantyl substituted phenyl.

[0025] According to one or more embodiments, the present application provides a hole transport material selected from any one of the following chemical structures:

[0026] The application also provides use of the hole transport material as described above in an organic electroluminescent device.

[0027] The application also provides an organic electroluminescent device, comprising:

[0028] a substrate layer;

[0029] a first electrode on the substrate;

[0030] an organic light-emitting functional layer on the first electrode;

[0031] a second electrode on the organic light-emitting functional layer;

[0032] The organic light-emitting functional layer comprises a hole transport layer; the hole transport layer comprises the hole transport material as described above.

[0033] The application also provides a composition comprising the hole transport material as described above.

[0034] The application also provides a preparation comprising the hole transport material as described above or the composition as described above and at least one solvent. The solvent is not particularly limited, and any solvent known to those skilled in the art can be used, such as unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran, tetrahydropyran, and ester solvents such as benzoic acid alkyl ester.

[0035] The organic electroluminescent device of the application can be used in an OLED lighting or display device.

[0036] The application also provides a display or lighting device comprising one or more of the organic electroluminescent devices as described above.

[0037] In summary, compared with the prior art, the application has the following beneficial effects:

[0038] The hole transport material provided by the present application takes triarylamine as a mother nucleus, is substituted by aryl and alkyl on a fluorene group, and is combined with heteroaryl and aryl on other side chain substitution sites, so that the compound structure is changed, and the compound has excellent light emitting efficiency and better evaporation stability; meanwhile, the hole transport material provided by the present application is used in a device, which is convenient for improving the hole transport efficiency in the device, thereby effectively improving the light emitting efficiency and working service life of the organic light emitting device. DETAILED DESCRIPTION

[0039] The technical solutions of the embodiments of the present application will be described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work are within the protection scope of the present application.

[0040] The aryl group refers to a general term of a monovalent group left after removing a hydrogen atom from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, which can be a monocyclic aryl group or a fused ring aryl group. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples can include a phenyl group, a biphenyl group, a terphenyl group, a triphenylene group, a tetraphenylene group, a naphthyl group, an anthryl group, a phenanthryl group or a pyrenyl group, but are not limited thereto. The aryl group or aromatic group, as used herein, contemplates non-fused and fused systems. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, pyrene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, and m-quaterphenyl.

[0041] The heteroaryl group according to the present application refers to a group in which one or more of the aromatic ring carbons in an aryl group is replaced by a heteroatom, including but not limited to an oxygen, sulfur, silicon, or nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl group or a fused ring heteroaryl group, and can be a heteroaryl group having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms. Examples can include a pyridyl group, a pyrrolyl group, a pyridyl group, a thienyl group, a furanyl group, an indolyl group, a quinolyl group, an isoquinolyl group, a benzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, and the like, but are not limited thereto.

[0042] The alkyl group according to the present application includes straight chain and branched chain alkyl groups. The alkyl group can be an alkyl group having 1 to 24 carbon atoms, and the preferred alkyl group is an alkyl group having 1 to 10 carbon atoms, including a methyl group, an ethyl group, a propyl group, a 1-methylethyl group, a butyl group, a 1-methylpropyl group, a 2-methylpropyl group, a pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, and the like. In addition, the alkyl group can be optionally substituted.

[0043] The cycloalkyl group according to the present application refers to any functional group or substituent derived from an alicyclic ring. The cycloalkyl group is a saturated cycloalkyl group having 3 or more and 20 or less ring carbon atoms. The cycloalkyl group can be a monocyclic, a bicyclic, a bridged, or a spirocyclic ring, and for example, can be a cyclohexane, a bicyclohexane, an adamantane, a bicyclo[2.2.2]octane, a norbornyl group, and the like, but is not limited thereto.

[0044] Throughout the specification, unless explicitly described to the contrary, the inclusion of any component will be understood to imply the inclusion of other elements, rather than the exclusion of any other elements. In addition, it will be understood that, throughout the specification, when an element such as a layer, film, region, or substrate is referred to as being "on" or "over" another element, it can be "directly on" the other element, or an intervening element can also be present. In addition, "on" or "over" refers to a position above the target portion, and does not necessarily refer to a position above in the direction of gravity.

[0045] An object of the present application is to provide an organic electroluminescent device including: a substrate layer; a first electrode over the substrate; an organic light-emitting functional layer over the first electrode; a second electrode over the organic light-emitting functional layer; the organic light-emitting functional layer containing a hole transport layer; and the hole transport layer containing a hole transport material represented by Formula (I).

[0046] In one embodiment of the present application, a hole transport layer in an organic electroluminescent (OLED) device contains one or more of the compounds represented by the above general formula (I) as a hole transport material.

[0047] In a preferred embodiment of the present application, an OLED is provided, which comprises a substrate, an anode, a cathode, an organic light-emitting functional layer, and a cover layer, wherein the organic light-emitting functional layer can comprise a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc., and can also comprise only a light-emitting layer and one or more other layers; wherein the hole transport layer comprises one or more of the compounds represented by the general formula (I) as described above. Optionally, there is also a protective layer and / or an encapsulating layer on the cover layer.

[0048] The substrate described in the present application can be any substrate used in a typical organic light-emitting device. It can be a glass or transparent plastic substrate, or a substrate of non-transparent material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water resistance, and the use direction is different depending on the properties of the substrate.

[0049] As the material for the hole injection layer, the electron injection layer, and the light-emitting layer, any material known for use in OLED devices can be selected and used.

[0050] As the host-guest material capable of generating blue fluorescence, green fluorescence, and blue-green fluorescence, not only is it necessary to have extremely high fluorescence quantum yield efficiency, but it is also necessary to have appropriate energy levels.

[0051] The present application will be described in detail below with reference to specific examples. All the raw materials and solvents used in the synthesis examples were commercially available and were used directly without further treatment, unless otherwise specified.

[0052] Examples

[0053] Example 1: Synthesis of compound H001

[0054] Synthetic route:

[0055] Synthetic method:

[0056] 1) H001-1 (18.3 g), H001-2 (27.3 g), pd2(dba)3 (1.2 g), X-Phos (1.5 g), sodium tert-butoxide (10 g) were sequentially added to a 500-milliliter solution of toluene, stirred at room temperature, and replaced with nitrogen five times, and then reacted at 80°C for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, washed with water, and separated into organic and aqueous phases. The organic phase was concentrated, and the intermediate product H001-S1 (30 g) was separated by column chromatography.

[0057] 2) Intermediate product H001-S1 (30 g), H001-3 (48 g), pd2(dba)3 (1 g), X-Phos (1.3 g), sodium tert-butoxide (9 g) were added into 400 mL of dimethylbenzene solution in turn, stirred at room temperature, replaced with nitrogen for five times, then refluxed for 12 hours. After the reaction was completed, it was cooled to room temperature, washed with water, separated, the organic phase was concentrated, and column chromatography was used to separate to obtain the target product 1-001 (55 g). LC-MS (m / z) (M+) analysis by liquid chromatography-mass spectrometry showed that the theoretical value was 899.45, and the test value was 900.15.

[0058] Example 2: Synthesis of compound H005

[0059] According to the synthesis steps and reaction conditions of Example 1, compound H005 was synthesized. LC-MS (m / z) (M+) analysis by liquid chromatography-mass spectrometry showed that the theoretical value was 699.39, and the test value was 699.95.

[0060] Example 3: Synthesis of compound H016

[0061] According to the synthesis steps and reaction conditions of Example 1, compound H016 was synthesized. LC-MS (m / z) (M+) analysis by liquid chromatography-mass spectrometry showed that the theoretical value was 985.43, and the test value was 986.17.

[0062] Example 4: Synthesis of compound H027

[0063] According to the synthesis steps and reaction conditions of Example 1, compound H027 was synthesized. LC-MS (m / z) (M+) analysis by liquid chromatography-mass spectrometry showed that the theoretical value was 951.48, and the test value was 952.08.

[0064] Example 5: Synthesis of compound H038

[0065] According to the synthesis steps and reaction conditions of Example 1, compound H038 was synthesized. LC-MS (m / z) (M+) analysis by liquid chromatography-mass spectrometry showed that the theoretical value was 847.42, and the test value was 848.06.

[0066] Example 6: Synthesis of compound H047

[0067] According to the synthesis steps and reaction conditions of Example 1, compound H047 was synthesized. LC-MS (m / z) (M+) analysis by liquid chromatography-mass spectrometry showed that the theoretical value was 964.48, and the test value was 965.10.

[0068] Example 7: Synthesis of compound H052

[0069] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H052 was synthesized. LC-MS (m / z) (M+): 901.43 calculated, 902.09 found.

[0070] Example 8: Synthesis of compound H057

[0071] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H057 was synthesized. LC-MS (m / z) (M+): 976.48 calculated, 977.12 found.

[0072] Example 9: Synthesis of compound H058

[0073] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H058 was synthesized. LC-MS (m / z) (M+): 915.44 calculated, 916.12 found.

[0074] Example 10: Synthesis of compound H064

[0075] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H064 was synthesized. LC-MS (m / z) (M+): 927.48 calculated, 928.20 found.

[0076] Example 11: Synthesis of compound H065

[0077] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H065 was synthesized. LC-MS (m / z) (M+): 851.45 calculated, 852.11 found.

[0078] Example 12: Synthesis of compound H068

[0079] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H068 was synthesized. LC-MS (m / z) (M+): 912.54 calculated, 913.26 found.

[0080] Example 13: Synthesis of compound H070

[0081] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H070 was synthesized. LC-MS (m / z) (M+): 845.41 calculated, 846.11 found.

[0082] Example 14: Synthesis of compound H080

[0083] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H080 was synthesized. LC-MS (m / z) (M+): 793.46 calculated, 794.10 found.

[0084] Example 15: Synthesis of compound H085

[0085] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H085 was synthesized. LC-MS (m / z) (M+): 687.39 calculated, 687.95 found.

[0086] Example 16: Synthesis of compound H086

[0087] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H086 was synthesized. LC-MS (m / z) (M+): 735.39 calculated, 736.07 found.

[0088] Example 17: Synthesis of compound H089

[0089] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H089 was synthesized. LC-MS (m / z) (M+): 925.46 calculated, 926.20 found.

[0090] Example 18: Synthesis of compound H091

[0091] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H091 was synthesized. LC-MS (m / z) (M+): 801.43 calculated, 802.05 found.

[0092] Example 19: Synthesis of compound H095

[0093] Following the synthetic procedure and reaction conditions of Reference Example 1, compound H095 was synthesized. LC-MS (m / z) (M+): 739.42 calculated, 740.04 found.

[0094] Example 20: Synthesis of compound H112

[0095] Following the procedure and reaction conditions of Reference Example 1, compound H112 was synthesized. LC-MS (m / z) (M+): 901.43 calculated, 902.09 found.

[0096] Example 21: Synthesis of compound H124

[0097] Following the procedure and reaction conditions of Reference Example 1, compound H124 was synthesized. LC-MS (m / z) (M+): 927.48 calculated, 928.20 found.

[0098] Example 22: Synthesis of compound H144

[0099] Following the procedure and reaction conditions of Reference Example 1, compound H144 was synthesized. LC-MS (m / z) (M+): 901.43 calculated, 902.09 found.

[0100] Example 23: Synthesis of compound H156

[0101] Following the procedure and reaction conditions of Reference Example 1, compound H156 was synthesized. LC-MS (m / z) (M+): 927.48 calculated, 928.20 found.

[0102] Example 24: Synthesis of compound H176

[0103] Following the procedure and reaction conditions of Reference Example 1, compound H176 was synthesized. LC-MS (m / z) (M+): 901.43 calculated, 902.09 found.

[0104] Example 25: Synthesis of compound H188

[0105] Following the procedure and reaction conditions of Reference Example 1, compound H188 was synthesized. LC-MS (m / z) (M+): 927.48 calculated, 928.20 found.

[0106] The following are several application examples of the hole transport material of the present application in OLED devices, to further illustrate the beneficial effects of the compounds of the present application. The materials used in the examples were either purchased commercially or synthesized in-house.

[0107] Fabrication of OLED devices:

[0108] As a reference preparation method of a device embodiment, the present application evaporates 50-500 nm of ITO / Ag / ITO as an anode on an alkali-free glass substrate, sequentially stacks and evaporates a hole injection layer (5-20 nm), a hole transport layer (50-150 nm), a light emitting auxiliary layer (5-120 nm), a light emitting layer (20-50 nm), a hole blocking layer (5-20 nm), an electron transport layer (20-80 nm), an electron injection layer (0.5-10 nm), and then co-evaporates Mg and Ag (weight ratio 1:9, 10-50 nm) to form a semi-transparent cathode, and then evaporates a cover layer compound. Finally, the light emitting device is encapsulated using an epoxy resin adhesive under a nitrogen atmosphere.

[0109] In a preferred embodiment, the structure of the OLED device provided by the present application is as follows: first, the alkali-free glass substrate is washed with isopropyl alcohol for 15 minutes using an ultrasonic cleaner, and then subjected to UV ozone washing treatment in air for 30 minutes. The treated substrate is evaporated using a vacuum evaporation method, first evaporating ITO / Ag / ITO 100 nm as an anode, and then sequentially stacking and evaporating a hole injection layer (HT:PD=97:3, 10 nm), a hole transport layer (compound H001, 135 nm), a light emitting auxiliary layer (BP, 5 nm), a blue light emitting layer (host material:doping material=compound BH:compound BD (weight ratio 98:2, 20 nm)), a hole blocking layer (HBL, 5 nm), an electron transport layer (compound ET:Liq=1:1, 30 nm), and an electron injection layer (Yb, 10 nm) on the anode, and then co-evaporating Mg and Ag (weight ratio 1:9, 14 nm) to form a semi-transparent cathode, and then evaporating compound CPL (70 nm) as a cover layer. This is denoted as Application Example 1, and the molecular structure of the relevant materials is shown below (particularly preferably selected from the following structures, but not limited to the following structures):

[0110] Application Examples 2-25 and Comparative Example 1 are prepared by the method provided in Application Example 1 described above, with the only difference being that the compounds listed in Table 1 are used as hole transport materials to replace compound H001 in Application Example 1. The structure of Ref-1 used in Comparative Example 1 is as follows:

[0111] Performance evaluation of OLED devices:

[0112] The OLED device was tested by Keithley 2365A digital nanovoltmeter at different voltages, and then the current was divided by the light-emitting area to obtain the current density of the OLED device at different voltages; the luminance and radiant energy flow density of the OLED device at different voltages were tested by Konicaminolta CS-2000 spectroradiometric luminance meter; according to the current density and luminance of the OLED device at different voltages, the operating voltage Volt and current efficiency (cd / A) at the same current density (10 mA / cm 2 ) were obtained, BI = E / CIEy, which refers to Blue Index in blue light, and is also a parameter for measuring the luminous efficiency of blue light, E refers to current efficiency, and CIEy refers to the ordinate color point obtained by bringing the half-peak width wavelength of the light-emitting device into CIE1930 software. The test data are shown in Table 1.

[0113] Table 1. Device and electron luminescence characteristics of application example of hole transport layer material

[0114] As can be seen from Table 1, compared with Comparative Example 1, Application Examples 1 to 25 have lower operating voltage and higher BI luminous efficiency. The performance improvement of each application example is based on the better film stability and transportability of the compound material of the application. The hole transport material in the application has a triarylamine as a mother nucleus, a co-substituted fluorenyl group of aromatic group and alkyl group and a heteroaryl group and an ortho-substituted aryl group as three side chains, which enhances the rigid conjugation effect of the compound, so that the compound has good thermal stability, which can greatly affect the luminescent properties of the compound, thereby improving the luminous efficiency of the device, better realizing the balance of electron and hole transport and the exciton conversion rate, and reducing the power consumption of the device.

[0115] The specific embodiments are only an explanation of the application, and are not a limitation of the application. Those skilled in the art can make modifications to the embodiments without creative contribution after reading the specification, as long as the modifications are within the scope of the claims of the application, and are protected by the patent law.

Claims

1. A hole transporting material, characterized by, The hole transport material has a compound having a structure represented by formula (I) below: In formula (I), X1independently represents CR a R b , NR c or an O, S atom, R a , R b , R c each independently selected from C1-C24alkyl, C6-C30aryl, C5-C30heteroaryl; R a , R b may be linked to each other to form a C3-C20cycloalkyl group; L1is selected from the group consisting of a single bond, substituted or unsubstituted C6-C30arylene, which can be mono-, di- or maximally possible number of substituted, when containing substituents, which can be hydrogen, deuterium, C1-C24alkyl, C3-C20cycloalkyl; R1is selected from the group consisting of substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C4-C36heteroaryl, when containing substituents, which can be C1-C24alkyl, C3-C20cycloalkyl, C6-C30aryl; L2, L3are each independently selected from the group consisting of a single bond, C1-C24alkyl, C3-C20cycloalkyl, substituted or unsubstituted C6-C30aryl, and the group consisting of; when containing substituents, which can be hydrogen, deuterium, C1-C24alkyl, C3-C20cycloalkyl; R2, R3are each independently selected from the group consisting of C1-C10alkyl, C6-C30aryl.

2. The hole transport material according to claim 1, wherein The compound of formula (I) can be partially or fully deuterated.

3. The hole transport material according to claim 1, wherein Compounds having the structure of Formula (i) or Formula (ii) below: wherein X1independently represents CR a R b , NR c or O, S atom, R a , R b , R c each independently selected from C1-C24alkyl, C6-C30aryl, C5-C30heteroaryl; L1is selected from the group consisting of a single bond, substituted or unsubstituted C6-C30arylene, which can be mono-, di- or maximally possible number of substituted, when containing substituents, which can be hydrogen, deuterium, C1-C24alkyl, C3-C20cycloalkyl; R1is selected from the group consisting of C6-C30aryl substituted or unsubstituted with C1-C24alkyl, C3-C20cycloalkyl, C6-C30aryl substituted or unsubstituted C4-C36heteroaryl; L2, L3are each independently selected from the group consisting of a single bond, C1-C24alkyl, C3-C20cycloalkyl, substituted or unsubstituted C6-C30aryl, and the group consisting of; when containing substituents, which can be hydrogen, deuterium, C1-C24alkyl, C3-C20cycloalkyl; R2, R3are each independently selected from the group consisting of C1-C10alkyl, C6-C30aryl.

4. The hole transport material according to claim 1, wherein In the formula (I), L2, L3are each independently selected from the group consisting of a single bond, n-propyl, i-propyl, C3-C6cycloalkyl, C1-C6alkyl substituted phenyl; R2, R3are each independently selected from the group consisting of methyl or phenyl.

5. The hole transport material according to claim 1, wherein The structure represented by formula (I) can be represented by any one of formula (I-1) to formula (I-2): wherein X1, L1, R1are as defined in claim 1.

6. The hole transport material according to claim 1, wherein The structure represented by formula (I) can be represented by any one of: wherein X1, L1, R1are as defined in claim 1.

7. The hole transport material according to claim 1, wherein when X1is represented by CR a R b , R a , R b are each independently selected from the group consisting of methyl, phenyl or R a , R b are each independently selected from the group consisting of methyl, phenyl or R c , R c are each independently selected from the group consisting of methyl, phenyl or R 8. The hole transport material according to claim 1, wherein In the formula (I), L1is selected from the group consisting of a single bond or C1-C10alkyl substituted C6-C30aryl; R1is independently selected from the group consisting of C6-C30aryl substituted or unsubstituted with C1-C5alkyl or C3-C10cycloalkyl, C6-C30aryl substituted or unsubstituted C4-C36heteroaryl.

9. The hole transport material according to claim 1, wherein In the formula (I), L1is independently selected from the group consisting of a single bond, phenyl, biphenyl, methylphenyl, dimethylphenyl, adamantyl substituted phenyl; R1is independently selected from the group consisting of phenyl, methylphenyl, dimethylphenyl, phenylcarbazolyl, dibenzofuranyl, adamantyl substituted phenyl.

10. The hole transport material according to claim 1, wherein The compound is selected from any one of the chemical structures shown below, wherein Ad represents "adamantyl":

11. Use of the hole transport material according to any one of claims 1 to 10 in the preparation of an organic electroluminescence device.

12. An organic electroluminescent device, characterized by The organic electroluminescence device comprises: a substrate layer; a first electrode on the substrate; an organic light-emitting functional layer on the first electrode; a second electrode on top of the organic light-emitting functional layer; The organic light-emitting functional layer comprises a hole transport layer; the hole transport layer comprises the hole transport material according to any one of claims 1-10.

13. A formulation characterized in that, The preparation comprises the hole transport material according to any one of claims 1-10 and at least one solvent.

14. A composition characterized in that, The composition comprises the hole transport material according to any one of claims 1-10.

15. Use of the organic electroluminescence device according to claim 12 in a display or illumination device.

16. A display or illumination device, characterized in that The device comprises the organic electroluminescence device according to claim 12.

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