Triphenylene compound and organic electroluminescent device containing triphenylene compound

Abstract

The invention provides a triphenylene compound and an organic electroluminescent device containing the triphenylene compound. The triphenylene compound has a structure as shown in a formula I. The structure of the triphenylene compound is designed, so that the triphenylene compound is suitable for being used as a main body material of a light-emitting layer of the organic light-emitting device, and the organic light-emitting device has relatively high current efficiency and relatively long service life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a triphenylene compound and an organic electroluminescent device containing the same. Background Art

[0002] Electroluminescence, also known as electric field luminescence, or EL for short, is a luminescence phenomenon in which a solid directly converts electrical energy into light energy under the action of an electric field generated by a voltage applied to two electrodes. Among them, the electroluminescence of organic materials belongs to injection-type composite luminescence. Organic electroluminescent materials can be divided into hole injection layer (HIL), hole transport layer (HTL), light-emitting layer (EML), electron transport layer (ETL), electron injection layer (EIL) and other materials according to their functions and device structures in organic electroluminescent (OLED) devices.

[0003] Currently, organic electroluminescence (OLED) has become the mainstream display technology, and accordingly, various new OLED materials have also been developed. However, its various performances need to be improved, especially in terms of efficiency, life, voltage, etc. In order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of blue light host materials with higher performance. Summary of the invention

[0004] In view of the shortcomings of the prior art, the present invention aims to provide a triphenylene compound and an organic electroluminescent device containing the same. In the present invention, the structure of the triphenylene compound is designed to make it suitable for use as a main material of the light-emitting layer of the organic electroluminescent device, and the organic electroluminescent device prepared thereby has a higher current efficiency and a longer lifespan.

[0005] To achieve this object, the present invention adopts the following technical solutions:

[0006] In a first aspect, the present invention provides a triphenylene compound having a structure as shown in the following formula I

[0007]

[0008] Wherein, any one of Ar1 and Ar2 is selected from -H or -D, and the other is selected from the group shown in formula I-1, and "*" represents the connection site;

[0009] R1, R 2、 R3 and R4 are each independently selected from any one of -H, C6-C40 aryl or C6-C30 heteroaryl;

[0010] m, n, o, and p are each independently selected from integers of 0 to 4;

[0011] The hydrogen atoms in the compound of formula I may each independently be substituted by at least one of -D (deuterium atom), -CN, -F, C6-C20 aryl, C1-C12 alkyl or C1-C12 alkoxy.

[0012] In the present invention, the structure of the triphenylene compound is designed so that two carbazole rings therein are in the ortho-substituted position, the two carbazole rings are in an approximately parallel state, the spatial structure is more regular, the charge transfer performance is better, and the triphenylene compound is more suitable for being used as a main material of a light-emitting layer of an organic electroluminescent device. Moreover, when m, n, o, and p are not all 0 at the same time, the charge density of the material molecule is increased, the charge transfer performance is stronger, and the voltage, efficiency, and life of the organic electroluminescent device prepared by using the material are further improved.

[0013] In the present invention, C6-C40 can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.

[0014] C6-C30 can be C6, C8, C10, C12, C16, C20, C24, C28 or C30, etc.

[0015] C6-C20 can be C6, C8, C10, C12, C16 or C20, etc.

[0016] C1-C12 can be C1, C2, C4, C6, C8, C10 or C12, etc.

[0017] It should be noted that, in the present invention, "-D" represents a deuterium atom, and the same applies hereinafter.

[0018] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0019] As a preferred technical solution of the present invention, the C6-C40 aromatic group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthanofluorenyl, pyrene, perylenyl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthanofluorenyl or benzonaphthofluorenyl.

[0020] Preferably, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl and dinaphthothiophenyl.

[0021] Preferably, the C6-C20 aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, triphenylene and fluoranthene.

[0022] Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl or decyl.

[0023] Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy.

[0024] As a preferred technical solution of the present invention, the Ar1 is selected from Formula I-1, and the Ar2 is selected from -H or -D.

[0025] As a preferred technical solution of the present invention, the Ar2 is selected from Formula I-1, and the Ar1 is selected from -H or -D.

[0026] Preferably, the triphenylene compound has a structure as shown in the following formula A:

[0027]

[0028] Among them, R1, R 2、 R3 and R4 have the same definitions as above, and R1 and R 2、 R3 and R4 are not -H at the same time.

[0029] As a preferred technical solution of the present invention, the R1, R 2、 R3 and R4 are each independently selected from any one of -H, phenyl, carbazolyl, biphenyl, fluorenyl, naphthyl, triphenylene, fluoranthenyl, indenofluorenyl, dibenzofuranyl, dibenzothienyl, naphthiobenzofuranyl or naphthiobenzothienyl.

[0030] Preferably, R1, R 2、 R3 and R4 are each independently selected from any one of -H, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0031] Preferably, R1, R 2、 R3 and R4 are each independently selected from any one of -H, phenyl, naphthyl, biphenyl, dibenzofuranyl or carbazolyl.

[0032] Preferably, R1 or R2 is a carbazole group, and R3 or R4 is a carbazole group.

[0033] As a preferred technical solution of the present invention, m, n, o, and p are each independently selected from 0 or 1.

[0034] As a preferred technical solution of the present invention, the hydrogen atoms in the compound of formula I can be independently replaced by at least one of -D, -CN, -F, phenyl, naphthyl, biphenyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy or butoxy.

[0035] Preferably, the hydrogen atoms in the compound of formula I may be independently substituted by at least one of -D, -F, -CN, methyl, tert-butyl, methoxy, propoxy or phenyl.

[0036] Preferably, the hydrogen atoms in the compound of formula I may be independently substituted by at least one of -CN, methoxy, ethoxy or propoxy.

[0037] As a preferred technical solution of the present invention, the triphenylene compound is selected from the following substituted or unsubstituted compounds:

[0038]

[0039]

[0040]

[0041] The substitution means that the hydrogen atoms in the above compounds can be independently replaced by deuterium atoms. Preferably, the triphenylene compound is selected from any one of the following compounds:

[0042]

[0043]

[0044] It should be noted that the present invention does not have any special limitation on the preparation method of triphenylene compounds, and all commonly used preparation methods in the art are applicable.

[0045] In a second aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode;

[0046] The organic thin film layer includes the triphenylene compound as described in the first aspect.

[0047] As a preferred technical solution of the present invention, the organic thin film layer includes a light-emitting layer;

[0048] The main material of the light-emitting layer includes the triphenylene compound as described in the first aspect.

[0049] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0050] As a preferred technical solution of the present invention, the organic electroluminescent device is a blue light organic electroluminescent device.

[0051] The luminescent layer in the present invention includes a luminescent layer main material and a doping material, wherein the doping material is also called a dye or a phosphorescent luminescent material. The luminescent layer main material can be a single compound or a mixture of two or more compounds.

[0052] The light-emitting layer includes a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer includes a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, a yellow phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

[0053] The volume percentage of the main material in the phosphorescent layer is 60% to 99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%, etc.), preferably 70% to 99.5%, and more preferably 85% to 95%.

[0054] In the present invention, the doping material of the light-emitting layer may be a phosphorescent material, which is also called a triplet light-emitting material, and refers to the light emitted from a triplet excited state. The specific selection of the phosphorescent material in the present invention is not particularly limited, and the doping materials of the light-emitting layer commonly used in the art are applicable, including but not limited to: a compound having a structure shown in Formula PD:

[0055]

[0056] Wherein, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0057] Y1-Y4 are each independently selected from carbon or nitrogen;

[0058] Y1 and Y2 can be connected by a single bond or a double bond, and Y3 and Y4 can be connected by a single bond or a double bond;

[0059] Cy1 and Cy2 are each independently selected from phenyl, naphthyl, fluorenyl, spirofluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothienyl, benzimidazolyl, benzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, N-heterocarbazolyl, N-heterodibenzofuranyl, wherein Cy1 and Cy2 may be optionally linked to each other via a single bond or an organic linking group;

[0060] Any two ligands of M, or more than two ligands, may be connected by a single bond or a double bond, or may be bridged by O or S, or may be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0061] R 91 and R 92 each independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid, carboxylate, sulfonic acid, sulfonate, phosphoric acid, phosphate, -SF5, substituted or unsubstituted C1-C60 (e.g., C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, substituted or unsubstituted C2-C6 C2-C60 (for example, C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) C2-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryl, substituted or unsubstituted C6-C60 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) For example, it can be any one of C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryloxy, substituted or unsubstituted C6-C60 (for example, it can be C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) arylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0062] a1 and a2 are each independently an integer selected from 1-5, for example, 1, 2, 3, 4 or 5;

[0063] b is an integer selected from 0-4, for example, 0, 1, 2, 3 or 4;

[0064] a is selected from 1, 2 or 3;

[0065] L1 is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0066] Preferably, the compound of formula PD is selected from any one of the following compounds:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] In the present invention, the organic thin film layer includes a hole layer, and the hole layer includes a hole injection layer, a hole transport layer and an electron blocking layer.

[0074] The hole injection layer material includes a P-type dopant. The P-type dopant refers to a dopant that coexists with the hole injection layer material in the OLED device and can oxidize the hole injection layer material, thereby acting as an electron acceptor and promoting the movement of holes in the hole injection layer to the anode. In the present invention, the difference between the absolute value of the LUMO of the P-type dopant and the absolute value of the HOMO of the hole layer material is greater than -0.2V, preferably greater than -0.1eV, more preferably greater than 0eV, more preferably greater than 0.1eV, and more preferably greater than 0.2eV.

[0075] The P-type dopant is present in the hole injection layer in a volume percentage of 1% to 10% (e.g., 1%, 2%, 4%, 6%, 8% or 10%). In the present invention, there is no particular limitation on the type of the P-type dopant, and illustratively, the compounds D-1 to D-13 disclosed in CN113728453A or the compounds HI-1 to HI-9 described below can be selected:

[0076]

[0077]

[0078] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) has a structure shown in the following formula HT-GH4:

[0079]

[0080] Among them, L 41is selected from a single bond, a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, or a C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;

[0081] Ar 41 ,Ar 42 Each is independently selected from C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, C6-C20 (for example, C6, C8, C10, C12, C16 or C20, etc.) heteroaryl;

[0082] X is selected from CR 41 R 42 or NR 43 , where R 41 , R 42 , R 43 Each independently selected from substituted or unsubstituted phenyl (the substituted substituent is selected from C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkoxy, dibenzofuranyl), naphthyl, triphenylene, fluoranthene, 9,9-dimethylfluorenyl, biphenyl, substituted or unsubstituted dibenzofuranyl (the substituted substituent is phenyl), substituted or unsubstituted dibenzothiophene (the substituted substituent is phenyl), dibenzofuran-substituted thienyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, any one of R 41 , R 42 They can be linked to form rings via single bonds.

[0083] The compound of formula HT-GH4 is selected from any one of the following compounds:

[0084]

[0085]

[0086]

[0087]

[0088]

[0089] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) also includes a compound having a structure shown in the following formula IA or a compound having a structure shown in the following formula IB:

[0090]

[0091] Wherein, L is selected from any one of C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) arylene, dibenzofuranyl or dibenzothiophenylene;

[0092] m is selected from an integer between 0 and 4 (for example, 0, 1, 2, 3 or 4), and n is selected from 0 or 1;

[0093] Ar is selected from any one of triphenylene, fluoranthenylene, dibenzofuranylene or dibenzothiophenylene;

[0094] Ar1 and Ar2 are each independently selected from any one of a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl group, a dibenzofuranyl group or a dibenzothiophenyl group;

[0095] Ar1 and Ar, Ar2 and Ar, and Ar1 and Ar2 can each independently be connected or bridged by a single bond, O, S, CR1R2, or NR.

[0096] R, R1, and R2 are each independently selected from any one of C1-C20 (for example, C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, or C20, etc.) alkyl, C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, dibenzofuranyl, or dibenzothiophenyl;

[0097] H in the compound of formula IB and the compound of formula IA can each independently be replaced by at least one of -F, -CN, -D (deuterium atom), C1-C6 alkyl, C1-C6 alkoxy, phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrenyl, perylenyl, spirofluorenyl, indenofluorenyl or hydrogenated benzanthryl.

[0098] Preferably, Ar is a fluoranthenyl group, and m+n>1.

[0099] Preferably, H in the compound of formula IB and the compound of formula IA can be replaced by at least one of -F, -CN, -D, C1-C3 alkyl (for example, methyl, ethyl or propyl), C1-C3 alkoxy (for example, methoxy, ethoxy or propoxy), phenyl, biphenyl, triphenylene, and fluoranthene.

[0100] Preferably, L, Ar1, Ar2 are each independently selected from at least one of phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrene, perylenyl, spirofluorenyl, indenofluorenyl or hydrogenated benzanthryl.

[0101] Preferably, the compound of formula IB is selected from the following structures:

[0102]

[0103] Wherein, L is phenylene;

[0104] Ar1, Ar2, and m have the same protection scope as described above.

[0105] Preferably, the compound of formula IB is selected from any one of the following compounds 1-112:

[0106]

[0107]

[0108]

[0109] In the OLED device provided by the present invention, the hole layer material may include conventional hole materials in the art in addition to the compound described in formula HT-GH4, the compound of formula IB, and the compound of formula IA, without special restrictions. Exemplary includes but is not limited to: triarylamine compounds or triphenylene compounds. Triarylamine compounds or triphenylene compounds containing more than 3 N atoms are preferred, because the HOMO of triarylamine compounds or triphenylene compounds containing more than 3 N atoms is higher (smaller absolute value), and is more suitable for use as hole injection layer materials. Triarylamine compounds or triphenylene compounds containing 2 or 1 N atoms can be used as hole transport layer materials. Some compounds or triphenylene compounds containing 1 N atom, if they have a higher LUMO, can also be used as electron blocking layer materials.

[0110] The triarylamine compound or triphenylene compound is used as the hole layer material, and the hole layer material includes the following structure:

[0111]

[0112]

[0113] Among them, Ar 601 ~Ar 609Each independently selected from any one of substituted or unsubstituted C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted naphthobenzothiophenyl, substituted or unsubstituted dinaphthofuranyl, substituted or unsubstituted dinaphthothiophenyl;

[0114] And Ar 601 ~Ar 609 Ar atoms adjacent to or connected to the same N atom 601 ~Ar 609 , can be connected by single key or through O, S, CR 701 R 702 NR 703 bridging;

[0115] R 701 , R 702 , R 703 is selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aromatic groups, C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl groups, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl groups, and R 701 , R 702 Can connect via one-touch.

[0116] The hole blocking layer (HBL) can confine holes and / or excitons within the EL to improve the current efficiency and lifetime of the device. Compared with the EL material closest to the HBL interface, the HBL material has a lower HOMO (larger absolute value) and / or higher triplet energy.

[0117] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped, and doping may be used to enhance conductivity. In the present invention, there is no particular restriction on the ETL material, and any metal complex or organic compound may be used as long as it can transport electrons. The general electron transport layer material contains the following structural fragments: at least one of a pyridine structure, a pyrimidine structure, a triazine structure, a benzimidazole structure, a benzoxazole structure, a benzothiazole structure, an N-naphthalene structure, an N-coffee structure, an N-carbazole structure, an N-dibenzofuran structure, and an N-dibenzothiophene structure.

[0118] In the present invention, there is no special restriction on the electron transport layer material, which exemplarily includes but is not limited to:

[0119]

[0120]

[0121] In the present invention, the material of the cathode is a metal with a low work function (e.g., alkaline earth metal, alkali metal, main group metal or lanthanide element (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.)), a metal alloy composed of multiple metals (alloy composed of alkali metal or alkaline earth metal and silver, such as an alloy composed of magnesium and silver) or a multilayer structure. If the cathode material is a multilayer structure, in addition to the metals mentioned above, other metals with relatively high work functions, such as Ag or Al, can also be used. In this case, a combination of the metals is usually used, such as Ca / Ag, Mg / Ag or Ba / Ag.

[0122] It is also possible to introduce a thin intermediate layer of a material with a high dielectric constant between the metal cathode and the organic semiconductor to form a multilayer structure; the material with a high dielectric constant can also be called an electron injection material, and fluorides of alkali metals or alkaline earth metals, and corresponding oxides or carbonates (such as LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.) or lithium quinoline (LiQ) can be selected.

[0123] Compared with the prior art, the present invention has the following beneficial effects:

[0124] The invention designs the structure of the triphenylene compound so that the triphenylene compound is suitable for being used as the main material of the light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer life. DETAILED DESCRIPTION

[0125] For the convenience of understanding the present invention, the present invention lists the following embodiments. 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.

[0126] Example 1

[0127] This example provides compound P1, the synthesis method of which is as follows:

[0128]

[0129] Under a nitrogen atmosphere, dry toluene (60 mL), intermediate M1 (3.8 g), carbazole (3.4 g), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 g), 10% tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine solution is 0.8 g) and sodium tert-butoxide (1.2 g) were added into a three-necked flask, heated to reflux reaction for 12 h, cooled to room temperature, and divided by adding water. The organic layer was then washed with water until neutral, dried with magnesium sulfate, filtered to remove the magnesium sulfate, concentrated to dryness, and crystallized from toluene to obtain compound P1 (4.7 g).

[0130] The mass spectrometry detection of compound P1: the mass-to-charge ratio (m / z) was measured to be 558.21.

[0131] Embodiment 2-9

[0132] Examples 2-9 provide a compound respectively. The synthesis method of the compound can refer to the synthesis method of compound P1 provided in Example 1, and the corresponding raw materials are used to react to prepare the corresponding compound, as shown in Table 1 below.

[0133] The obtained compounds were subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) data are shown in Table 1 below.

[0134] Table 1

[0135]

[0136]

[0137]

[0138] Other compounds whose specific synthesis methods are not listed can be synthesized by referring to the above embodiments in combination with common knowledge in the art.

[0139] The specific structures of some compositions used in the following application examples and comparative application examples are as follows:

[0140]

[0141]

[0142] Application Example 1

[0143] This application example provides a blue light organic electroluminescent device, using the compound P1 provided by the present invention as a main material of the light-emitting layer, and the structure of the blue light organic electroluminescent device is:

[0144] ITO / HT-1: HI-2 [5%] (70nm) / HT-1 (35nm) / host material: PBD-1 [5%] (35nm) / ETL-1 (25nm) / LiF (0.5nm) / Al (150nm).

[0145] The preparation method of the blue light organic electroluminescent device is as follows:

[0146] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate in sequence to prepare an OLED device.

[0147] Among them, PBD-1[5%] refers to the doping ratio of the dye, that is, the volume ratio of the main material to the dye PBD-1 is 95:5; HT-1:HI-2[5%] refers to the ratio of the P-type dopant, that is, the volume ratio of the hole material HT-1 and the P-type dopant HI-2 is 95:5, and HT-1 is a hole transport material; HT-1:HI-2[5%] are used as materials for forming a hole injection layer.

[0148] Application Example 2-10

[0149] Application Examples 2-10 respectively provide an organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced by other compounds (see Table 2 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0150] Comparative application example 1

[0151] Comparative Application Example 1 provides an organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced by other compounds (see Table 2 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0152] Performance Testing

[0153] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the current efficiency is the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density, where the current efficiency and LT95 are relative values. The specific test results are shown in Table 2 below:

[0154] Table 2

[0155] Main material dye <![CDATA[Luminance / (cd / m 2 )]]> Current efficiency LT95 Application Example 1 P1 PBD-1 1000 1 1 Application Example 2 P2 PBD-1 1000 0.96 1.07 Application Example 3 P3 PBD-1 1000 1.02 1.26 Application Example 4 P4 PBD-1 1000 0.99 1.11 Application Example 5 P5 PBD-1 1000 0.97 1.09 Application Example 6 P6 PBD-1 1000 0.98 1.22 Application Example 7 P7 PBD-1 1000 1.21 1.39 Application Example 8 P8 PBD-1 1000 1.33 1.16 Application Example 9 P9 PBD-1 1000 1.16 0.89 Application Example 10 P10 PBD-1 1000 1.47 1.02 Comparative application example 1 D1 PBD-1 1000 0.88 0.67

[0156] From the above content, it can be known that the present invention designs the structure of triphenylene compounds to make them suitable as the main material of the light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer life.

[0157] From the comparison between Application Example 1 and Application Example 9, it can be seen that in the present invention, by designing the compound of Formula I, Ar1 is selected from the group shown in Formula I-1, and the current efficiency of the organic electroluminescent device prepared by using this triphenylene compound as the main material of the light-emitting layer is improved.

[0158] From the comparison between Application Example 3 and Application Example 2, it can be seen that when the triphenylene compound having the structure shown in Formula A is selected as the main material of the light-emitting layer, the prepared organic electroluminescent device has a longer lifespan.

[0159] It can be seen from Application Examples 4-5 that when at least one hydrogen atom in the compound of Formula I is replaced by -CN or -F, the life of the organic electroluminescent device can be further improved.

[0160] It can be seen from Application Examples 7-8 that when R1 or R2 in the compound of Formula I is a carbazole group, and R3 or R4 is a carbazole group, using such triphenylene compounds as the main material of the light-emitting layer can further improve the current efficiency and life of the organic electroluminescent device.

[0161] From the above content, it can be known that the present invention designs the structure of triphenylene compounds to make them suitable as the main material of the light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer life.

[0162] The applicant declares that the present invention illustrates the detailed process flow of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed process flow, that is, it does not mean that the present invention must rely on the above-mentioned detailed process flow 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. A triphenylene compound, It is characterized in that The triphenylene compound has a structure as shown in the following formula I: Among them, Ar 1 ,Ar 2 Any one of them is selected from -H or -D, and the other is selected from the group shown in formula I-1, and "*" represents the connection site; R 1 , R 2、 R 3 , R 4 Each is independently selected from any one of -H, C6-C40 aryl or C6-C30 heteroaryl; m, n, o, and p are each independently selected from integers of 0 to 4; The hydrogen atoms in the compound of formula I may each independently be substituted by at least one of -D, -CN, -F, C6-C20 aryl, C1-C12 alkyl or C1-C12 alkoxy.

2. The triphenylene compound according to claim 1, It is characterized in that The C6-C40 aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthofluorenyl or benzonaphthofluorenyl; Preferably, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl and dinaphthothiophenyl; Preferably, the C6-C20 aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, triphenylene, and fluoranthenyl; Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl or decyl; Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy.

3. The triphenylene compound according to claim 1 or 2, It is characterized in that The Ar 1 Selected from formula I-1, said Ar 2 Select from -H or -D.

4. The triphenylene compound according to any one of claims 1 to 3, It is characterized in that The Ar 2 Selected from formula I-1, said Ar 1 Selected from -H or -D; Preferably, the triphenylene compound has a structure as shown in the following formula A: Among them, R 1 , R 2、 R 3 , R 4 has the same definition as in claim 1, and R 1 , R 2、 R 3 , R 4 Not at the same time -H.

5. The triphenylene compound according to any one of claims 1 to 4, It is characterized in that The R 1 , R 2、 R 3 , R 4 Each is independently selected from any one of -H, phenyl, carbazolyl, biphenyl, fluorenyl, naphthyl, triphenylene, fluoranthenyl, indenofluorenyl, dibenzofuranyl, dibenzothienyl, naphthobenzofuranyl or naphthobenzothienyl; Preferably, the R 1 , R 2、 R 3 , R 4 Each is independently selected from any one of -H, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; Preferably, the R 1 , R 2、 R 3 , R 4 Each is independently selected from any one of -H, phenyl, naphthyl, biphenyl, dibenzofuranyl or carbazole; Preferably, the R 1 or R 2 is carbazole, R 3 or R 4 It is a carbazolyl group.

6. The triphenylene compound according to any one of claims 1 to 5, It is characterized in that m, n, o, and p are each independently selected from 0 or 1.

7. The triphenylene compound according to any one of claims 1 to 6, It is characterized in that The hydrogen atoms in the compound of formula I may be independently substituted by at least one of -D, -CN, -F, phenyl, naphthyl, biphenyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy or butoxy; Preferably, the hydrogen atoms in the compound of formula I can each independently be substituted by at least one of -D, -F, -CN, methyl, tert-butyl, methoxy, ethoxy, propoxy or phenyl; Preferably, the hydrogen atoms in the compound of formula I may be independently substituted by at least one of -CN, methoxy, ethoxy or propoxy.

8. The triphenylene compound according to any one of claims 1 to 7, It is characterized in that The triphenylene compound is selected from the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the above compounds can each be independently replaced by a deuterium atom.

9. An organic electroluminescent device, It is characterized in that The organic electroluminescent device comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode; The organic thin film layer comprises the triphenylene compound according to any one of claims 1 to 8; Preferably, the organic thin film layer includes a light-emitting layer; The main material of the light-emitting layer includes the triphenylene compound as described in any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, It is characterized in that The light-emitting layer is a phosphorescent light-emitting layer; Preferably, the organic electroluminescent device is a blue organic electroluminescent device.

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