Organic light-emitting device

Abstract

The present invention relates to an organic electroluminescent device, comprising: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layer at least includes a light-emitting layer, and the material of the light-emitting layer includes a host material and a guest material. The guest material includes at least one of a compound of formula (I) and a compound of formula (II), and the host material includes a compound of formula (III): The organic electroluminescent device has high luminous efficiency and long lifespan.

Description

Technical Field

[0001] The present invention relates to the field of light-emitting devices, and particularly to an organic electroluminescent device. Background Art

[0002] Due to the diversity of organic semiconductor materials, relatively low manufacturing costs, and excellent optical and electrical properties, etc., there is great potential in the preparation of organic light-emitting diodes (OLEDs) or optoelectronic devices, such as organic electronic devices like flat panel displays and lighting devices.

[0003] The principle of light emission of organic electronic devices is organic electroluminescence, which refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic electroluminescent device using organic electroluminescence usually has a positive electrode and a negative electrode, and a functional layer containing an organic substance in between. To improve the efficiency and lifespan of the organic electroluminescent element, the functional layer has a multi-layer structure, and each functional layer contains different organic substances. Specifically, it includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, or an electron injection layer, etc. In an organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic layer, and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when these excitons transition back to the ground state, light is emitted. Such an organic electroluminescent element has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] To improve the light-emitting efficiency of organic electroluminescent devices, various light-emitting material systems based on fluorescence and phosphorescence have been developed. Currently, organic light-emitting diodes using blue fluorescent materials have higher reliability. However, the development of blue fluorescent materials with excellent optical and electrical properties faces a huge challenge. In traditional technologies, the emission spectra of most blue fluorescent materials are too wide, and the color purity is poor, which is not conducive to high-end displays. Moreover, the light-emitting efficiency of OLED devices made using such blue fluorescent materials is poor, and the service life is low, and there is a need for further improvement.

[0005] Therefore, it is of great significance to develop electronic devices with high light-emitting efficiency and long service life. Summary of the Invention

[0006] Based on this, it is necessary to provide an organic electroluminescent device with high light-emitting efficiency and long service life.

[0007] The technical solution of the present invention is as follows:

[0008] One aspect of the present invention provides an organic electroluminescent device, which comprises: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode, the organic functional layer at least comprising a light-emitting layer, the light-emitting layer material comprising a host material and a guest material, the guest material comprising at least one of a compound of formula (I) and a compound of formula (II), and the host material comprising a compound of formula (III):

[0009]

[0010] wherein Ar 1 ~Ar 7 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0011] Each occurrence of X is independently selected from CR1 or N;

[0012] Z is selected from NR2, PR2, CR3R4, SiR3R4, O, S, S(=O)2 or S(=O);

[0013] Each occurrence of R1~R4 is independently selected from: H, D, a straight-chain alkyl having 1 to 20 C atoms, a straight-chain alkoxy having 1 to 20 C atoms, a straight-chain thioalkoxy having 1 to 20 C atoms, a branched-chain alkyl having 3 to 20 C atoms, a cycloalkyl having 3 to 20 C atoms, a branched-chain alkoxy having 3 to 20 C atoms, a cyclic alkoxy having 3 to 20 C atoms, a branched-chain thioalkoxy having 3 to 20 C atoms, a cyclic thioalkoxy having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, OCF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms, a substituted or unsubstituted aryloxy having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaryloxy having 5 to 40 ring atoms, or a combination of these systems;

[0014] Two adjacent R1s are connected to form a ring or do not form a ring;

[0015] m(A)-L-(D) n (III);

[0016] wherein L is selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0017] D, at each occurrence, is independently selected from a substituted or unsubstituted electron-donating aromatic group having 6 to 40 ring atoms, a substituted or unsubstituted electron-donating heteroaromatic group having 5 to 40 ring atoms, or an electron-donating amine;

[0018] Each occurrence of A is independently selected from an electron withdrawing group;

[0019] m is selected from any integer from 1 to 5; n is selected from any integer from 1 to 5;

[0020] The difference (ΔEst) between the singlet energy level and the triplet energy level of the compound of formula (III) is less than or equal to 0.3 eV.

[0021] Another aspect of the present invention provides a light-emitting device, which comprises a light-emitting layer, wherein the light-emitting layer contains the light-emitting layer material as described above.

[0022] Beneficial Effects

[0023] The light-emitting layer material of the present invention comprises a host material and a guest material, wherein the guest material comprises at least one of a compound of formula (I) and a compound of formula (II), and the host material comprises a compound of formula (III); wherein, in the compound of formula (I) or (II), at least one nitrogen atom and two boron atoms are included in the same rigid plane, and the two are not twisted and staggered, and the planar arrangement of the molecules is beneficial to structural stability and light output, and at the same time, the compound can better utilize the energy of the triplet state, can realize the anti-system crossing from the triplet state to the singlet state, and has a high internal quantum efficiency; the host material of the compound of formula (III) also has the characteristic of high energy utilization rate of anti-system crossing from the triplet state to the singlet state, and the efficiency and service life of the light-emitting device are better improved by matching the host / guest with high energy utilization rate. DETAILED DESCRIPTION

[0024] In order to facilitate the understanding of the present invention, the present invention will be described more fully below. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the understanding of the disclosure of the present invention more thorough and comprehensive.

[0025] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terms used in the specification of the present invention are for the purpose of describing specific embodiments only and are not intended to limit the present invention. The term "and / or" used herein includes any and all combinations of one or more of the related listed items.

[0026] Terms and Definitions

[0027] In the present invention, "substituted" means that a hydrogen atom in a substituent is replaced by a substituent.

[0028] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple R1s, then each R1 can be independently selected from different groups.

[0029] In the present invention, "substituted or unsubstituted" means that the defined group can be either substituted or unsubstituted. When the defined group is substituted, it should be understood as being optionally substituted by groups acceptable in the art, including but not limited to: deuterium atom, cyano group, isocyano group, nitro group, halogen atom, C 1-10 alkyl of 1-10 alkoxy of 1-10 alkylthio of 6-30 aryl of 6-30 aryloxy of 6-30 arylthio of 3-30 heteroaryl of 1-30 silyl of 2-10 alkylamino of 6-30 arylamino of, or a combination of the above groups, etc.

[0030] In the present invention, "the number of ring atoms" refers to the number of atoms that form a ring structure by bonding atoms (for example, monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, heterocyclic compounds). When the ring is substituted by substituents, the atoms contained in the substituents are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thiophenyl group is 5.

[0031] In the present invention, "alkyl" can represent straight-chain, branched-chain, and / or cyclic alkyl. The number of carbon atoms in the alkyl can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" means an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group or C9 alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, n-triacontyl, adamantane, etc.

[0032] "Aryl or aromatic group" means an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, or a fused-ring aryl group, or a polycyclic aryl group. For polycyclic ring species, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group having 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include but are not limited to: benzene, biphenyl, terphenyl, naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dibenzo[a,h]anthracene, tetracene, pyrene, benzo[a]pyrene, acenaphthene, fluorene and their derivatives. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0033] "Heteroaryl or heteroaromatic group" means that at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" means a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted. Suitable examples include but are not limited to: triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thiophenopyrrole, thiophenothiophene, furanopyrrole, furanofuran, thiophenofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, perimidine, quinazoline, quinazolinone, dibenzothiophene, dibenzofuran, carbazole and their derivatives.

[0034] "Amino group" refers to derivatives of amines, having a structural feature of the formula -N(X)2, where each "X" is independently H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0035] In the present invention, "*" connected to a single bond represents a connection or fusion site.

[0036] In the present invention, when the connection site is not specified in a group, it means that any optional connection site in the group can be used as the connection site;

[0037] In the present invention, when the fusion site is not specified in a group, it means that any optional fusion site in the group can be used as the fusion site, and preferably two or more sites adjacent to each other in the group are the fusion sites;

[0038] In the present invention, the single bond to which a substituent is connected passes through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring. For example in which R is connected to any substitutable site of the benzene ring, such as in is fused to any optional fusion site of the benzene ring.

[0039] In the present invention, "adjacent groups" refer to two substituents without any substitutable sites between them.

[0040] In the present invention, "#" represents the site where a group is connected to other partial groups in the compound where the group is located; for example, in the compound of formula (Ⅲ), when A is A is connected to other groups in the compound of formula (Ⅲ) through three connection sites; when the connection site is not specified, it means that the group is connected to other partial groups in the compound where it is located through any one or more optional connection sites.

[0041] In the present invention, the host material, matrix material, Host or Matrix material have the same meaning and can be interchanged with each other.

[0042] In the embodiments of the present invention, the energy level structure of the organic material, the triplet energy level ET, HOMO, and LUMO play a key role. The determination of these energy levels is introduced below.

[0043] The HOMO and LUMO energy levels can be measured by photoelectric effect, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or by cyclic voltammetry (hereinafter referred to as CV). Recently, quantum chemical methods, such as density functional theory (hereinafter referred to as DFT), have also become effective methods for calculating the energy levels of molecular orbitals.

[0044] The triplet energy level ET1 of the organic material can be measured by low-temperature time-resolved luminescence spectroscopy or obtained by quantum simulation calculations (such as by Time-dependent DFT), such as through commercial software Gaussian 09W (Gaussian Inc.). The specific simulation method can be referred to WO2011141110 or as described in the following examples.

[0045] It should be noted that the absolute values of HOMO, LUMO, and ET1 depend on the measurement method or calculation method used. Even for the same method, different evaluation methods, such as the starting point and peak point on the CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement method and the same evaluation method. In the description of the embodiments of the present invention, the values of HOMO, LUMO, and ET1 are based on the simulation of Time-dependent DFT, but it does not affect the application of other measurement or calculation methods.

[0046] One embodiment of the present invention provides an organic electroluminescent device, which includes: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layer at least includes a light-emitting layer. The light-emitting layer material includes a host material and a guest material. The guest material includes at least one of the compound of formula (Ⅰ) and the compound of formula (Ⅱ), and the host material includes the compound of formula (Ⅲ):

[0047]

[0048] Wherein, Ar 1 ~Ar 7 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0049] Each occurrence of X is independently selected from CR1 or N;

[0050] Z is selected from NR2, PR2, CR3R4, SiR3R4, O, S, S(=O)2 or S(=O);

[0051] Each occurrence of R1 to R4 is independently selected from: H, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, a linear thioalkoxy group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, a cycloalkyl group having 3 to 20 C atoms, a branched alkoxy group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a branched thioalkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, OCF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 40 ring atoms, or a combination of these systems;

[0052] Two adjacent R1s are connected to form a ring or not;

[0053] m(A)-L-(D) n (III);

[0054] Wherein, L is selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0055] Each occurrence of D is independently selected from a substituted or unsubstituted aromatic group having 6 to 40 ring atoms and having an electron-donating property, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms and having an electron-donating property, or an amino group having an electron-donating property;

[0056] Each occurrence of A is independently selected from an electron-withdrawing group;

[0057] m is selected from any integer from 1 to 5; n is selected from any integer from 1 to 5;

[0058] And the singlet-triplet energy level difference (△Est) of the compound of formula (III) is less than or equal to 0.3 eV.

[0059] In one embodiment, each occurrence of R1 to R4 is independently selected from: H, D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cycloalkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms, or a combination of these systems.

[0060] In one embodiment, each occurrence of R1 to R4 is independently selected from: H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cycloalkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 5 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these systems.

[0061] In one embodiment, Ar 1 ~Ar 7 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 25 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 25 ring atoms.

[0062] In one embodiment, Ar 1 ~Ar 7 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms.

[0063] In one embodiment, Ar 1 ~Ar 7 are each independently selected from any one of formulas (B-1) to (B-12):

[0064]

[0065] Wherein:

[0066] Each occurrence of X1 is independently selected from CR5 or N; when X1 is a connection site, X1 is selected from C;

[0067] Each occurrence of Y is independently selected from NR6, PR6, CR7R8, SiR7R8, O, S, S(=O)2 or S(=O);

[0068] Each occurrence of R5 to R8 is independently selected from: H, D, a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain thioalkoxy group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cycloalkyl group having 3 to 20 C atoms, a branched-chain alkoxy group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a branched-chain thioalkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, OCF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 40 ring atoms, or a combination of these systems;

[0069] Two adjacent R5s are connected to form a ring or not; R7 and R8 are connected to form a ring or not. In some embodiments, in formula (I), Ar 1 ~Ar 3 are independently selected from formulae (B-2) to (B-9).

[0070] In some embodiments, in formula (I), at least one of Ar 1 ~Ar 3 is selected from formula (B-2); further, Ar 2 is selected from (B-2).

[0071] In some embodiments, in formula (I), at least two of Ar 1 ~Ar 3 are selected from formula (B-2); further, Ar 2 and Ar 3 are selected from (B-2).

[0072] In some embodiments, in formula (I), Ar 1 ~Ar 3 are all selected from formula (B-2).

[0073] In some embodiments, in formula (I), at least one of Ar 1 ~Ar 3 is selected from formula (B-2), and at least one other is selected from formula (B-6). Further, Ar 1 ~Ar 3Any two of them are each independently selected from formula (B-2), and the other is selected from formula (B-6).

[0074] In some embodiments, in formula (I), Ar 1 ~Ar 3 At least one of them is selected from formula (B-2), and at least one other is selected from formula (B-4). Further, Ar 1 ~Ar 3 Any two of them are each independently selected from formula (B-2), and the other is selected from formula (B-4).

[0075] In some embodiments, in formula (I), Ar 1 ~Ar 3 At least one of them is selected from formula (B-2), and at least one other is selected from formula (B-3). Further, Ar 1 ~Ar 3 Any two of them are each independently selected from formula (B-2), and the other is selected from formula (B-3).

[0076] In some embodiments, in formula (I), Ar 1 ~Ar 3 At least one of them is selected from formula (B-2), and at least one other is selected from formula (B-7). Further, Ar 1 ~Ar 3 Any two of them are each independently selected from formula (B-2), and the other is selected from formula (B-7).

[0077] In some embodiments, in formula (I), Ar 1 ~Ar 3 At least one of them is selected from formula (B-2), and at least one other is selected from formula (B-9). Further, Ar 1 ~Ar 3 Any two of them are each independently selected from formula (B-2), and the other is selected from formula (B-9).

[0078] In some preferred embodiments, Ar 1 is selected from (B-4). Further, Ar 2 is selected from (B-2). Still further, Ar 3 is selected from (B-2), (B-3) or (B-6). The reason is that introducing heteroatoms into the framework structure near the B atom can better regulate the optoelectronic properties of the molecule.

[0079] In some of the preferred embodiments, when the above-mentioned guest material is selected from formula (I), Ar 1 and Ar 3 At least one of them is selected from Further preferably, Ar 2 is

[0080] In some embodiments, in formula (II), Ar 4 ~Ar 7 are each independently selected from formulae (B-2) to (B-9).

[0081] In some embodiments, formula (II) is a symmetric structure compound.

[0082] In some preferred embodiments, formula (II) is an asymmetric structure compound.

[0083] In some embodiments, in formula (II), Ar 4 and Ar 7 are selected from (B-2)-(B-6); further, Ar 4 and Ar 7 are selected from the same group; further, Ar 4 and Ar 7 are selected from

[0084] In one embodiment, in formula (II), Ar 5 and Ar 6 are selected from (B-2)-(B-6); further, Ar 5 and Ar 6 are selected from the same group; further, Ar 5 and Ar 6 are selected from

[0085] In one embodiment, in formula (II), Ar 4 is selected from (B-3); further, Ar 5 ~Ar 7 are independently selected from (B-2).

[0086] In one embodiment, in formula (II), Ar 5 is selected from (B-4); further, Ar 4 , Ar 6 , Ar 7 are independently selected from (B-2).

[0087] In one of the embodiments, Ar 1 ~Ar 7 are each independently selected from any one of formulae (C-1) to (C-22):

[0088]

[0089]

[0090] Among them, * represents the fusion site.

[0091] In a preferred embodiment, Ar 1 is selected from (C-5); further, Ar 2 is selected from (C-2). Further, the compound of formula (I) is selected from any one of formulas (1-1) to (1-16):

[0092]

[0093]

[0094] Further, Z is selected from NR2, CR3R4, O or S; further, Z is selected from NR2 or S; further, R2 is selected from: H, D, a straight-chain alkyl having 1 to 10 carbon atoms, a branched-chain alkyl having 3 to 10 carbon atoms, a cyclic alkyl having 3 to 10 carbon atoms, an aromatic group having 5 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms substituted by a straight-chain alkyl having 1 to 10 carbon atoms, a branched-chain alkyl having 3 to 10 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms substituted by a branched-chain alkyl having 3 to 10 carbon atoms or a cyclic alkyl having 3 to 10 carbon atoms.

[0095] Further, R2 is selected from H, D, a straight-chain alkyl having 1 to 5 carbon atoms, a branched-chain alkyl having 3 to 10 carbon atoms, or the following structure:

[0096]

[0097] wherein, R 19 each occurrence is independently selected from: H, D, a straight-chain alkyl having 1 to 10 carbon atoms, an aromatic group having 5 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms substituted by a straight-chain alkyl having 1 to 10 carbon atoms, a branched-chain alkyl having 3 to 10 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms, a heteroaromatic group having 5 to 20 ring atoms substituted by a branched-chain alkyl having 3 to 10 carbon atoms or a cyclic alkyl having 3 to 10 carbon atoms.

[0098] n3 is selected from any integer from 1 to 4.

[0099] In some embodiments, n3 is selected from any integer from 1 to 3.

[0100] In some embodiments, n3 is selected from 1; in other embodiments, n3 is selected from 2.

[0101] In one embodiment, R 19 is independently selected from: H, D, a straight-chain alkyl group having 1 to 5 C atoms, an aromatic group having 6 to 10 ring atoms, a heteroaromatic group having 5 to 10 ring atoms; further, r1 is independently selected from: H, D, methyl, isopropyl, tert-butyl or phenyl.

[0102] In one embodiment, the compound of formula (II) is selected from any one of formulas (2-1) to (2-13):

[0103]

[0104]

[0105]

[0106] In some embodiments, each occurrence of X1 is selected from CR5; further, each occurrence of R5 is independently selected from: H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 5 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these systems.

[0107] Further, each occurrence of R5 is independently selected from: H, D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms; still further, at least one R5 is selected from a straight-chain alkyl group having 1 to 8 C atoms or a branched-chain alkyl group having 3 to 8 C atoms; still further, at least one R5 is selected from methyl, isopropyl or as shown in the following formula:

[0108] wherein n is selected from any integer from 0 to 4.

[0109] It is understood that when n is 0, R5 is tert-butyl.

[0110] In some embodiments, each occurrence of X is selected from CR1, and each occurrence of R1 is independently selected from H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cycloalkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 5 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these systems.

[0111] Further, each occurrence of R1 is independently selected from: H, D, a straight-chain alkyl group having 1 to 8 C atoms, a branched-chain alkyl group having 3 to 8 C atoms; further, at least one R1 is independently selected from: methyl, isopropyl or the following structure:

[0112] wherein n is any integer selected from 0 - 4.

[0113] It is understood that when n is selected as 0, R1 is tert-butyl.

[0114] In some embodiments, each occurrence of Y is independently selected from NR6, CR7R8, O or S; further, each occurrence of R6 - R8 is independently selected from H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cycloalkyl group having 3 to 10 C atoms, an unsubstituted aromatic group having 6 to 20 ring atoms, an unsubstituted heteroaromatic group having 5 to 20 ring atoms, or an aromatic group having 6 to 20 ring atoms substituted by a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms or a cycloalkyl group having 3 to 10 C atoms, or a heteroaromatic group having 5 to 20 ring atoms substituted by a branched-chain alkyl group having 3 to 10 C atoms or a cycloalkyl group having 3 to 10 C atoms.

[0115] In some embodiments, when Ar 1 ~Ar 7 is selected from formula (C-2), formula (C-2) is selected from the following structures:

[0116]

[0117] wherein: the meaning of R5 is as described above. Further, (C-2) is selected from the following structures:

[0118]

[0119] In some embodiments, the compound of formula (I) is as shown in formula (I-2) or (II-2):

[0120]

[0121] Preferably, each R1 is independently selected from: methyl, isopropyl or the following structure:

[0122] wherein n is any integer selected from 0 - 4.

[0123] In some embodiments, in the compound of formula (III), D is selected from any one of formulas (3-1) to (3-3):

[0124]

[0125] Wherein, each occurrence of Y2 is independently selected from a single bond, NR 12 , CR 13 R 14 , O or S;

[0126] R9 - R 14 Each occurrence is independently selected from: H, D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cycloalkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 40 ring atoms, or a combination of these systems;

[0127] R 13 and R 14 are connected to form a ring or not to form a ring.

[0128] In one embodiment, when R 13 and R 14 form a ring with each other, D is selected from the following groups:

[0129]

[0130] Wherein: Y5 has the same meaning as Y2.

[0131] In some embodiments, D is selected from any one of the following groups:

[0132]

[0133] In some embodiments, A is selected from any one of formulas (4 - 1) to (4 - 12):

[0134]

[0135] Wherein, each occurrence of Y3 is independently selected from absent, a single bond, NR 15 , CR 15 R 16 , O or S;

[0136] Each occurrence of Y4 is independently selected from NR 15 , CR 15 R 16 , O or S;

[0137] Each occurrence of X2 is independently selected from CR 17 or N, and at least one X2 is selected from N;

[0138] Each occurrence of X3 is independently selected from CR 18 or N;

[0139] R 15 ~R 18 Each occurrence is independently selected from: H, D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cycloalkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms, or a combination of these systems; R 15 and R 16 either form a ring or do not form a ring with each other;

[0140] * represents a connection site.

[0141] In some embodiments, R 15 ~R 18 Each occurrence is independently selected from: H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cycloalkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0142] In some embodiments, when R 15 and R 16 form a ring with each other, A is selected from the following groups:

[0143]

[0144] Y4 has the same meaning as Y; X2 and X3 have the same meaning as X.

[0145] In some embodiments, A is selected from any one of the following groups:

[0146]

[0147]

[0148] wherein, # represents the site where the group is connected to other partial groups in the compound of formula (Ⅲ).

[0149] In some embodiments, the above compound of formula (Ⅲ) is selected from any one of (Ⅲ-1) to (Ⅲ-7):

[0150]

[0151] In the present invention, it should be noted that when L is not directly connected to the electron-donating group D or the electron-withdrawing group A, it means that L can be connected to any connectable site on the electron-donating group D or the electron-withdrawing group A.

[0152] Preferably, A is selected from Further, D is selected from

[0153] In some embodiments, each occurrence of Y2 is independently selected from a single bond, NR 12 , CR 13 R 14 or O; further, each occurrence of R9-R 14 is independently selected from: H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 20 ring atoms; still further, each occurrence of R9-R 14 is independently selected from: H, D, a straight-chain alkyl group having 1 to 5 C atoms, a branched-chain alkyl group having 3 to 5 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms.

[0154] In some embodiments, L is selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0155] In some embodiments, L is selected from a single bond and any one of the following groups:

[0156] W is selected from N, O or S.

[0157] In one embodiment, the above host material is selected from formula (III-2) or formula (III-4); preferably, the above host material is selected from at least one of formulas (III-a) to (III-c):

[0158]

[0159] Preferably, the above guest material is selected from at least one of formula (1-2), formula (2-2), formula (2-7), formula (2-9), formula (2-11) and formula (2-13);

[0160] Further, the above guest material is selected from formula (2-7) or formula (2-11).

[0161] In one embodiment, the host material is selected from (III-c), and the guest material is selected from formula (2-7) or formula (2-11).

[0162] Further, formula (III-c) is selected from the following general formula:

[0163]

[0164] Preferably, Y2 is selected from NR 12; Further, R 12 each occurrence is independently selected from: H, D, a linear alkyl group having 1 to 5 C atoms, a branched alkyl group having 3 to 5 C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms.

[0165] Further, ΔEst of the compound of formula (III) is ≤ 0.25 eV; preferably, ΔEst of the compound of formula (III) is ≤ 0.15 eV.

[0166] Further, examples of the compound of formula (I) and the compound of formula (II) of the present invention include, but are not limited to, the structures shown in formulas (1) to (226):

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] Examples of the compound of formula (III) are given here, including but not limited to the following compounds:

[0174]

[0175]

[0176] In one embodiment, the compounds of formula (I), formula (II) and formula (III) of the present invention may be partially deuterated. Preferably, 10% of H is deuterated, more preferably 20% of H is deuterated, still more preferably 30% of H is deuterated, and most preferably 40% of H is deuterated.

[0177] In some embodiments, the mass ratio of the above-mentioned host material to the guest material is 99:1 to 80:20; further, the mass ratio of the host material to the guest material is 99:1 to 90:10.

[0178] In some of these embodiments, the above-mentioned organic electroluminescent device further includes other functional layers, including a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Materials suitable for preparing the hole injection layer, hole transport layer, electron blocking layer, electron injection layer, electron transport layer, and hole blocking layer can be found in the following patent documents: WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of the above-listed patent documents are hereby incorporated herein by reference.

[0179] In some embodiments, the organic functional layer includes a hole transport layer, a light-emitting layer, and an electron transport layer.

[0180] In other embodiments, the organic functional layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0181] In one embodiment, the organic electroluminescent device further includes a light extraction layer, which is located on the surface of the electrode and on the side away from the organic functional layer; further, the light extraction layer is located on the surface of the cathode.

[0182] In one embodiment, the organic multi-functional layer is prepared by vacuum evaporation, coating, or printing.

[0183] Further, the coating method includes at least one of dip coating, spin coating, blade coating, spraying, brush coating, and slot die coating.

[0184] Further, the printing method includes at least one of inkjet printing, inkjet printing, letterpress printing, screen printing, roller printing, rotary screen printing, lithographic printing, flexographic printing, gravure printing, rotary printing, and pad printing. In some embodiments, the printing method is at least one of gravure printing, inkjet printing, and inkjet printing.

[0185] The organic electroluminescent device described in the present invention can be selected from an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor, or an organic plasmonic emitter diode. Preferably, the organic electroluminescent device described in the present invention is selected from an organic light-emitting diode (OLED).

[0186] In the above-mentioned organic electroluminescent device, especially an OLED, it includes a substrate, an anode, at least one light-emitting layer, a cathode, and the light-emitting layer contains the light-emitting layer material as described above.

[0187] Specifically, the substrate can be opaque or transparent. A transparent substrate can be used to fabricate a transparent light-emitting device. See, for example, Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface. A substrate without surface defects is a particularly ideal choice. In a preferred embodiment, the substrate is flexible and can be selected from polymer films or plastics with a glass transition temperature Tg above 150 °C, preferably above 200 °C, more preferably above 250 °C, and most preferably above 300 °C. Examples of suitable flexible substrates include poly(ethylene terephthalate) (PET) and poly(ethylene 2,6-naphthalate) (PEN).

[0188] The anode can include a conductive metal, metal oxide, or conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known and can be easily selected and used by those of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the light-emitting devices according to the present invention.

[0189] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the light-emitting substance in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as the cathode of an OLED may be used as the cathode material of the device of the present invention. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0190] For the light-emitting device according to the present invention, its emission wavelength is between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm.

[0191] The present invention also relates to the use of the light-emitting device according to the present invention in the preparation of light-emitting electronic devices.

[0192] The above-mentioned light-emitting electronic devices include, but are not limited to: display devices, lighting devices, light sources, and sensors, etc.

[0193] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims define the scope of the present invention. Under the guidance of the inventive concept of the present invention, those skilled in the art should be aware that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention. Specific Embodiments

[0195] Synthesis Example 1

[0196] Synthesis of Compound M1:

[0197]

[0198] The specific synthesis steps are as follows:

[0199] 1) Synthesis of intermediate M1-3: Under nitrogen environment, (32.1 g, 100 mmol) of compound M1-1, (14.9 g, 100 mmol) of compound M1-2, (0.92 g, 1 mmol) of compound Pd2(dba)3, (0.4 g, 2 mmol) of compound tri-tert-butylphosphine, (13.7 g, 150 mmol) of compound sodium tert-butoxide and 200 mL of anhydrous toluene solvent were added to a 500 mL two-necked flask, heated to 60°C, stirred for reaction for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane and washed 3 times, the organic liquid was collected and mixed with silica gel and passed through a column for purification to obtain intermediate M1-3, the eluent was petroleum ether: dichloromethane in a volume ratio of 3:1, and the yield was 80%.

[0200] 2) Synthesis of intermediate M1-6: Under nitrogen environment, (39.6 g, 100 mmol) of compound M1-4, (17.8 g, 100 mmol) of compound M1-5, (3.31 g, 3 mmol) of tetrakistriphenylphosphine palladium, (27.6 g, 200 mmol) of potassium carbonate in 50 mL of aqueous solution and 200 mL of toluene were added to a 500 mL three-necked flask, heated and stirred to 110 ° C for 12 hours, the reaction was terminated, cooled to room temperature, the filtrate was filtered, most of the solvent was evaporated by rotary evaporation, dissolved in dichloromethane and washed three times, the organic liquid was collected and mixed with silica gel column for purification to obtain intermediate M1-6, the eluent was petroleum ether: dichloromethane in a volume ratio of 5:1, and the yield was 70%.

[0201] 3) Synthesis of intermediate M1-7: Under nitrogen environment, (24.2 g, 60 mmol) of compound M1-6, (23.4 g, 60 mmol) of compound M1-3, (0.55 g, 0.6 mmol) of compound Pd2(dba)3, (0.24 g, 1.2 mmol) of compound tri-tert-butylphosphine, (8.2 g, 90 mmol) of compound sodium tert-butoxide and 150 mL of anhydrous toluene solvent were added to a 300 mL two-necked flask, heated to 60 ° C, stirred for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane and washed 3 times, the organic liquid was collected and mixed with silica gel column for purification to obtain intermediate M1-7, the eluent was petroleum ether: dichloromethane in a volume ratio of 4:1, and the yield was 70%.

[0202] 4) Synthesis of intermediate M1-9: Under nitrogen environment, (28.5 g, 40 mmol) of compound M1-7, (11.3 g, 40 mmol) of compound M1-8, (0.37 g, 0.4 mmol) of compound Pd2(dba)3, (0.16 g, 0.8 mmol) of compound tri-tert-butylphosphine, (5.5 g, 60 mmol) of compound sodium tert-butoxide and 100 mL of anhydrous toluene solvent were added to a 250 mL two-necked flask, heated to 60 ° C, stirred for 6 hours, cooled to room temperature, quenched with water, and the reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane and washed 3 times, the organic liquid was collected and mixed with silica gel column for purification to obtain intermediate M1-9, the eluent was petroleum ether: dichloromethane in a volume ratio of 2.5:1, and the yield was 70%.

[0203] 5) Synthesis of Compound M1: Under nitrogen environment, (18.3 g, 20 mmol) Compound M1-9 and 100 mL of anhydrous toluene solvent were added to a 300 mL three-necked flask, stirred to dissolve, cooled to -78°C, slowly added 45 mmol of tert-butyl lithium, reacted for 2 hours, added 50 mmol of boron tribromide at one time, allowed the reaction solution to slowly rise to room temperature, continued to stir and react for 3 hours, added 80 mmol of diisopropylethylamine at one time, heated to 100°C and reacted for 4 hours, after the reaction was completed, the reaction solution was rotary evaporated to remove most of the solvent, washed 3 times with dichloromethane, collected the organic solution, mixed with silica gel and purified by column to obtain Compound M1, the eluent was petroleum ether: dichloromethane in a volume ratio of 3.5:1, and the yield was 53%. MS (ASAP): 894.

[0204] Synthesis of compound M2:

[0205]

[0206]

[0207] (1) Synthesis of intermediate M2-2: According to the synthesis method of compound M1-3, compound M2-1 was used instead of compound M1-1, with a yield of 85%.

[0208] (2) Synthesis of intermediate M2-3: According to the synthesis method of compound M1-7, compound M2-2 was used instead of compound M1-3, with a yield of 72%.

[0209] (3) Synthesis of intermediate M2-4: According to the synthesis method of compound M1-9, compound M2-3 was used instead of compound M1-7, with a yield of 68%.

[0210] (4) Synthesis of compound M2: According to the synthesis method of compound M1, compound M2-4 was used instead of compound M1-9, with a yield of 55%, MS (ASAP): 779.

[0211] Synthesis of Compound M3:

[0212]

[0213] (1) Synthesis of Intermediate M3-3: According to the synthesis method of Compound M1-3, replace Compounds M1-1 and M1-2 with Compounds M3-1 and M3-2 respectively, with a yield of 82%.

[0214] (2) Synthesis of Intermediate M3-6: According to the synthesis method of Compound M1-6, replace Compounds M1-4 and M1-5 with Compounds M3-5 and M3-4 respectively, with a yield of 75%.

[0215] (3) Synthesis of Intermediate M3-7: According to the synthesis method of Compound M1-6, replace Compound M1-5 with Compound M3-4, with a yield of 68%.

[0216] (4) Synthesis of Intermediate M3-8: According to the synthesis method of Compound M1-7, replace Compounds M1-6 and M1-3 with Compounds M3-7 and M3-3 respectively, with a yield of 72%.

[0217] (5) Synthesis of Intermediate M3-9: According to the synthesis method of Compound M1-9, replace Compounds M1-7 and M1-8 with Compounds M3-8 and M3-6 respectively, with a yield of 73%.

[0218] (6) Synthesis of Compound M3: According to the synthesis method of Compound M1, replace Compound M1-9 with Compound M3-9, with a yield of 54%, MS(ASAP): 839.

[0219] Synthesis of Compound M4:

[0220]

[0221] (1) Synthesis of Intermediate M4-2: According to the synthesis method of Compound M1-3, replace Compounds M1-1 and M1-2 with Compounds M4-1 and M3-2 respectively, with a yield of 78%.

[0222] (2) Synthesis of Intermediate M4-4: According to the synthesis method of Compound M1-7, replace Compounds M1-6 and M1-3 with Compounds M4-3 and M4-2 respectively, with a yield of 73%.

[0223] (3) Synthesis of Intermediate M4-5: According to the synthesis method of Compound M1-9, replace Compounds M1-7 and M1-8 with Compounds M4-4 and M3-6 respectively, with a yield of 71%.

[0224] (4) Synthesis of Compound M4: According to the synthesis method of Compound M1, replace Compound M1-9 with Compound M3-9, with a yield of 52%, MS(ASAP): 763.

[0225] Synthesis of Compound M5:

[0226]

[0227] (1) Synthesis of Intermediate M5-3: According to the synthesis method of Compound M1-3, replace Compound M1-1 with Compound M5-1, with a yield of 86%.

[0228] (2) Synthesis of Intermediate M5-5: According to the synthesis method of Compound M1-6, replace Compound M1-4 and M1-5 with Compound M5-4 and M5-3 respectively, with a yield of 75%.

[0229] (3) Synthesis of Intermediate M5-6: According to the synthesis method of Compound M1-7, replace Compound M1-3 with Compound M5-2, with a yield of 70%.

[0230] (4) Synthesis of Intermediate M5-7: According to the synthesis method of Compound M1-9, replace Compound M1-7 and M1-8 with Compound M5-6 and M5-5 respectively, with a yield of 70%.

[0231] (5) Synthesis of Compound M5: According to the synthesis method of Compound M1, replace Compound M1-9 with Compound M5-7, with a yield of 50%, MS(ASAP): 894.

[0232] Synthesis of Compound M6:

[0233]

[0234] (1) Synthesis of Intermediate M6-2: According to the synthesis method of Compound M1-3, replace Compound M1-1 with Compound M6-1, with a yield of 85%.

[0235] (2) Synthesis of Intermediate M6-4: According to the synthesis method of Compound M1-6, replace Compound M1-4 and M1-5 with Compound M3-5 and M6-3 respectively, with a yield of 77%.

[0236] (3) Synthesis of Intermediate M6-5: According to the synthesis method of Compound M1-7, replace Compound M1-6 and M1-3 with Compound M3-7 and M6-2 respectively, with a yield of 73%.

[0237] (4) Synthesis of Intermediate M6-6: According to the synthesis method of Compound M1-9, replace Compound M1-7 and M1-8 with Compound M6-5 and M6-4 respectively, with a yield of 71%.

[0238] (5) Synthesis of Compound M6: According to the synthesis method of Compound M1, using Compound M6-6 to replace Compound M1-9, with a yield of 53%, MS (ASAP): 723.

[0239] Synthesis of Compound M7:

[0240]

[0241] (1) Synthesis of Intermediate M7-2: Under a nitrogen atmosphere, add (19.4 g, 100 mmol) of Compound M7-1, (3.6 g, 150 mmol) of sodium hydride, and 200 mL of tetrahydrofuran solvent to a 500 mL two-necked flask, stir and react for 1 h, add (40.3 g, 100 mmol) of Compound M1-6, continue to stir and react for 6 h, quench with water, rotary evaporate most of the solvent from the reaction solution, dissolve with dichloromethane, wash with water 3 times, collect the organic layer, mix with silica gel and purify by column chromatography to obtain Intermediate M7-2. The eluent is petroleum ether:dichloromethane = 4:1 by volume, with a yield of 70%.

[0242] (2) Synthesis of Intermediate M7-3: According to the synthesis method of Compound M1-9, using Compound M7-2 to replace Compound M1-7, with a yield of 72%.

[0243] (3) Synthesis of Compound M7: According to the synthesis method of Compound M1, using Compound M7-3 to replace Compound M1-9, with a yield of 54%, MS (ASAP): 698.

[0244] Synthesis of Compound M8:

[0245]

[0246] The specific synthesis steps are as follows:

[0247] 1) Synthesis of Intermediate M8-2: Under a nitrogen atmosphere, add (28.8 g, 100 mmol) of Compound M8-1 and 150 mL of anhydrous tetrahydrofuran solvent to a 500 mL two-necked flask, stir to dissolve, cool down to -78 °C, slowly dropwise add 100 mmol of n-butyllithium, maintain the temperature, continue to stir and react for 2 h, add 100 mmol of sulfur powder at one time, let the reaction naturally rise to room temperature, continue to stir and react for 4 h, add 100 mL of 2 mmol / mL ammonium chloride aqueous solution, stir and react for 0.5 h, rotary evaporate most of the solvent from the reaction solution, dissolve with dichloromethane, wash with water 3 times, collect the organic layer, mix with silica gel and purify by column chromatography to obtain Intermediate M8-2. The eluent is petroleum ether:dichloromethane = 3:1 by volume, with a yield of 70%.

[0248] 2) Synthesis of Intermediate M8-3: Referring to the synthesis method of Compound M7-2, replacing Compound M7-1 with Compound M8-2, with a yield of 68%.

[0249] 3) Synthesis of Intermediate M8-5: Referring to the synthesis method of Compound M1-9, replacing Compound M1-7 and Compound M1-8 with Compound M8-3 and Compound M8-4 respectively, with a yield of 70%.

[0250] 4) Synthesis of Compound M8: Referring to the synthesis method of Compound M1, replacing Compound M1-9 with Compound M8-5, with a yield of 52%. MS(ASAP): 703.

[0251] Synthesis of Compound M9:

[0252]

[0253]

[0254] (1) Synthesis of Intermediate M9-2: According to the synthesis method of Compound M1-3, replacing Compound M1-1 with Compound M9-1, with a yield of 78%.

[0255] (2) Synthesis of Intermediate M9-3: According to the synthesis method of Compound M1-7, replacing Compound M1-3 with Compound M9-2, with a yield of 69%.

[0256] (3) Synthesis of Intermediate M9-4: According to the synthesis method of Compound M1-9, replacing Compound M1-7 with Compound M9-3, with a yield of 65%.

[0257] (4) Synthesis of Compound M9: According to the synthesis method of Compound M1, replacing Compound M1-9 with Compound M9-4, with a yield of 50%, MS(ASAP): 841.

[0258] Synthesis of Compound M10:

[0259]

[0260] (1) Synthesis of Intermediate M10-3: According to the synthesis method of Compound M1-3, replacing Compound M1-1 and M1-2 with Compound M10-1 and M10-2 respectively, with a yield of 75%.

[0261] (2) Synthesis of Intermediate M10-5: According to the synthesis method of Compound M1-6, replacing Compound M1-4 and M1-5 with Compound M5-4 and M10-4 respectively, with a yield of 70%.

[0262] (3) Synthesis of intermediate M10-6: According to the synthesis method of compound M1-7, compound M10-3 was used instead of compound M1-3, with a yield of 70%.

[0263] (4) Synthesis of intermediate M10-7: According to the synthesis method of compound M1-9, compounds M10-6 and M10-5 were used to replace compounds M1-7 and M1-8, with a yield of 67%.

[0264] (5) Synthesis of compound M10: According to the synthesis method of compound M1, compound M10-7 was used instead of compound M1-9. The yield was 54%, MS (ASAP): 747.

[0265] Synthesis of compound M11:

[0266]

[0267] (1) Synthesis of intermediate M11-3: Under nitrogen environment, (48.8 g, 100 mmol) of compound M11-1, (24.4 g, 200 mmol) of compound M11-2, (3.31 g, 3 mmol) of tetrakistriphenylphosphine palladium, (27.6 g, 200 mmol) of potassium carbonate aqueous solution (50 mL) and 200 mL of toluene were added to a 500 mL three-necked flask, heated and stirred to 80°C for 12 h, and then cooled to room temperature. The filtrate was filtered, most of the solvent was evaporated by rotary evaporation, and the mixture was washed three times with dichloromethane and dissolved in water. The organic liquid was collected and mixed with silica gel column for purification to obtain intermediate M11-3. The eluent was petroleum ether: dichloromethane in a volume ratio of 4.5:1, and the yield was 67%.

[0268] (2) Synthesis of intermediate M11-5: Under nitrogen, (23.3 g, 60 mmol) of compound M11-3, (20.3 g, 120 mmol) of compound M11-4, (1.1 g, 1.2 mmol) of compound Pd2(dba)3, (0.48 g, 2.4 mmol) of compound tri-tert-butylphosphine, (13.7 g, 90 mmol) of compound sodium tert-butoxide and 150 mL of anhydrous toluene solvent were added to a 300 mL two-necked flask, heated to 60°C, stirred for reaction for 6 h, cooled to room temperature, and quenched with water. The reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane and washed three times, the organic solution was collected and mixed with silica gel column for purification to obtain intermediate M11-5, the eluent was petroleum ether: dichloromethane in a volume ratio of 1.5:1, and the yield was 65%.

[0269] (3) Synthesis of Compound M11: Under a nitrogen atmosphere, (11.3 g, 20 mmol) of Compound M11-5 and 100 mL of anhydrous toluene solvent were added to a 300 mL three-necked flask, stirred and dissolved, cooled to -78 °C, 65 mmol of tert-butyllithium was slowly added dropwise, reacted for 2 h, 70 mmol of boron tribromide was added, the reaction solution was slowly raised to room temperature, and the reaction was continued with stirring for 3 h. 100 mmol of diisopropylethylamine was added, and the reaction was heated at 100 °C for 4 h. Most of the solvent was removed by rotary evaporation of the reaction solution, washed three times with dichloromethane, and the organic layer was collected and purified by silica gel column chromatography to obtain Compound M11. The eluent was petroleum ether:dichloromethane = 3:1 (v / v), and the yield was 45%. MS(ASAP): 588.

[0270] Synthesis of Compound M12:

[0271]

[0272] (1) Synthesis of Intermediate M12-2: According to the synthesis method of Compound M1-6, Compound M5-4 and M12-1 were used to replace Compound M1-4 and M1-5 respectively, and the yield was 69%.

[0273] (2) Synthesis of Intermediate M12-3: According to the synthesis method of Compound M11-3, Compound M1-5 was used to replace Compound M11-2, and the yield was 70%.

[0274] (3) Synthesis of Intermediate M12-4: According to the synthesis method of Compound M11-5, Compound M12-3 and M12-2 were used to replace Compound M11-3 and M11-4 respectively, and the yield was 63%.

[0275] (4) Synthesis of Compound M12: According to the synthesis method of Compound M11, Compound M12-4 was used to replace Compound M11-5, and the yield was 42%, MS(ASAP): 913.

[0276] Synthesis of Compound M13:

[0277]

[0278] (1) Synthesis of Intermediate M13-2: According to the synthesis method of Compound M1-6, Compound M5-4 and M13-1 were used to replace Compound M1-4 and M1-5 respectively, and the yield was 69%.

[0279] (2) Synthesis of Intermediate M13-3: According to the synthesis method of Compound M11-5, Compound M12-3 and M13-2 were used to replace Compound M11-3 and M11-4 respectively, and the yield was 60%.

[0280] (3) Synthesis of Compound M13: According to the synthesis method of Compound M11, using Compound M13-3 to replace Compound M11-5, with a yield of 46%, MS(ASAP): 1025.

[0281] Synthesis of Compound M14:

[0282]

[0283]

[0284] (1) Synthesis of Intermediate M14-2: According to the synthesis method of Compound M1-6, using Compounds M5-4 and M14-1 to replace Compounds M1-4 and M1-5 respectively, with a yield of 70%.

[0285] (2) Synthesis of Intermediate M14-3: According to the synthesis method of Compound M11-5, using Compounds M12-3 and M14-2 to replace Compounds M11-3 and M11-4 respectively, with a yield of 62%.

[0286] (3) Synthesis of Compound M14: According to the synthesis method of Compound M11, using Compound M14-3 to replace Compound M11-5, with a yield of 44%, MS(ASAP): 1103.

[0287] Synthesis of Compound M15:

[0288]

[0289] (1) Synthesis of Intermediate M15-2: According to the synthesis method of Compound M1-6, using Compounds M5-4 and M15-1 to replace Compounds M1-4 and M1-5 respectively, with a yield of 72%.

[0290] (2) Synthesis of Intermediate M15-3: According to the synthesis method of Compound M11-5, using Compounds M12-3 and M15-2 to replace Compounds M11-3 and M11-4 respectively, with a yield of 61%.

[0291] (3) Synthesis of Compound M15: According to the synthesis method of Compound M11, using Compound M15-3 to replace Compound M11-5, with a yield of 47%, MS(ASAP): 893.

[0292] Synthesis of Compound M16:

[0293]

[0294] (1) Synthesis of Intermediate M16-1: According to the synthesis method of Compound M11-3, using Compound M12-1 to replace Compound M11-2, with a yield of 68%.

[0295] (2) Synthesis of Intermediate M16-2: According to the synthesis method of Compound M11-5, replace Compounds M11-3 and M11-4 with Compounds M16-1 and M1-8 respectively, with a yield of 64%.

[0296] (3) Synthesis of Compound M16: According to the synthesis method of Compound M11, replace Compound M11-5 with Compound M16-2, with a yield of 46%, MS(ASAP): 913.

[0297] Synthesis of Compound M17:

[0298]

[0299] (1) Synthesis of Intermediate M17-2: According to the synthesis method of Compound M11-3, replace Compound M11-2 with Compound M17-1, with a yield of 69%.

[0300] (2) Synthesis of Intermediate M17-3: According to the synthesis method of Compound M11-5, replace Compounds M11-3 and M11-4 with Compounds M17-2 and M1-8 respectively, with a yield of 66%.

[0301] (3) Synthesis of Compound M17: According to the synthesis method of Compound M11, replace Compound M11-5 with Compound M17-3, with a yield of 41%, MS(ASAP): 1075.

[0302] Synthesis of Compound M18:

[0303]

[0304] (1) Synthesis of Intermediate M18-2: According to the synthesis method of Compound M11-3, replace Compound M11-2 with Compound M18-1, with a yield of 67%.

[0305] (2) Synthesis of Intermediate M18-3: According to the synthesis method of Compound M11-5, replace Compounds M11-3 and M11-4 with Compounds M18-2 and M1-8 respectively, with a yield of 64%.

[0306] (3) Synthesis of Compound M18: According to the synthesis method of Compound M11, replace Compound M11-5 with Compound M18-3, with a yield of 40%, MS(ASAP): 925.

[0307] Synthesis of Compound M19:

[0308]

[0309] (1) Synthesis of Intermediate M19-1: According to the synthesis method of Compound M1-6, replace Compound M1-4 with Compound M11-1, with a yield of 63%.

[0310] (2) Synthesis of Intermediate M19-2: According to the synthesis method of Compound M1-6, replace Compound M1-4 with Compound M19-1 and Compound M1-5 with Compound M6-3 respectively, with a yield of 68%.

[0311] (3) Synthesis of Intermediate M19-3: According to the synthesis method of Compound M11-5, replace Compound M11-3 with Compound M19-2 and Compound M11-4 with Compound M1-8 respectively, with a yield of 65%.

[0312] (4) Synthesis of Compound M19: According to the synthesis method of Compound M11, replace Compound M11-5 with Compound M19-3, with a yield of 44%, MS(ASAP): 917.

[0313] Synthesis of Compound M20:

[0314]

[0315] (1) Synthesis of Intermediate M20-1: According to the synthesis method of Compound M1-6, replace Compound M1-4 with Compound M5-4 and Compound M1-5 with Compound M18-1 respectively, with a yield of 73%.

[0316] (2) Synthesis of Intermediate M20-2: According to the synthesis method of Compound M1-7, replace Compound M1-6 with Compound M12-3 and Compound M1-3 with Compound M1-8 respectively, with a yield of 64%.

[0317] (3) Synthesis of Intermediate M20-3: According to the synthesis method of Compound M1-7, replace Compound M1-6 with Compound M20-2 and Compound M1-3 with Compound M20-1 respectively, with a yield of 68%.

[0318] (4) Synthesis of Compound M20: According to the synthesis method of Compound M11, replace Compound M11-5 with Compound M20-3, with a yield of 42%, MS(ASAP): 925.

[0319] Synthesis of Compound M21:

[0320]

[0321] The specific synthesis steps are as follows:

[0322] 1) Synthesis of Compound M21: Under a nitrogen atmosphere, (10 g, 50 mmol) of Compound M21-1, (68 g, 410 mmol) of Compound M21-1, potassium carbonate (55.2 g, 400 mmol), and 200 mL of N,N-dimethylformamide solvent were added to a 500 mL three-necked flask. The mixture was stirred at 155 °C for 12 hours, cooled to room temperature, and the reaction solution was poured into 300 mL of pure water. The mixture was extracted with dichloromethane and washed three times with water. The organic layer was collected, mixed with silica gel, and purified by column chromatography. The eluent was a mixture of petroleum ether:dichloromethane = 2:1 (v / v), and Compound M21 was obtained with a yield of 56%. MS (ASAP): 789.

[0323] Synthesis of Compound M22:

[0324]

[0325] The specific synthesis steps are as follows:

[0326] 1) Synthesis of Compound M22: Under a nitrogen atmosphere, (20.5 g, 50 mmol) of Compound M22-1, (2.4 g, 100 mmol) of sodium hydride, and 150 mL of tetrahydrofuran solvent were added to a 300 mL three-necked flask. The mixture was stirred for 1 hour, and then (13.4 g, 50 mmol) of Compound M22-2 was added all at once. The mixture was stirred for an additional 6 hours. Most of the solvent was removed by rotary evaporation. The reaction solution was poured into 300 mL of pure water. The mixture was extracted with dichloromethane and washed three times with water. The organic layer was collected, mixed with silica gel, and purified by column chromatography. The eluent was a mixture of petroleum ether:dichloromethane = 3:1 (v / v), and Compound M22 was obtained with a yield of 81%. MS (ASAP): 640.

[0327] Synthesis of Compound M23:

[0328]

[0329] The specific synthesis steps are as follows:

[0330] 1) Synthesis of Compound M23: According to the synthesis method of Compound M22, Compound M23-1 was used instead of Compound M22-1, and the yield was 76%. MS (ASAP): 564.

[0331] Synthesis of Compound M24:

[0332]

[0333] The specific synthesis steps are as follows:

[0334] 1) Synthesis of Compound M24: Under a nitrogen atmosphere, (28.3 g, 50 mmol) of Compound M24-1, (9.9 g, 110 mmol) of cuprous cyanide, and 100 mL of N-methyl-2-pyrrolidone solvent were added to a 300 mL three-necked flask. The mixture was stirred at 170 °C for 24 hours. After the reaction was completed, the reaction solution was allowed to cool to room temperature. The reaction solution was poured into 200 mL of aqueous sodium hydroxide solution, stirred, and then aqueous sodium hypochlorite solution was added. Stirring was continued for 30 minutes. The mixture was extracted with dichloromethane and washed three times with water. The organic layer was collected, stirred with silica gel, and purified by column chromatography. The eluent was petroleum ether:dichloromethane = 4:1 (v / v), and Compound M24 was obtained with a yield of 83%. MS (ASAP): 457.

[0335] Synthesis of Compound M25:

[0336]

[0337] The specific synthesis steps are as follows:

[0338] 1) Synthesis of Compound M25: According to the synthesis method of Compound M1-7, Compound M25-1 and M25-2 were used to replace Compound M1-3 and M1-6 respectively, with a yield of 78%. MS (ASAP): 728.

[0339] Synthesis of Compound M26:

[0340]

[0341] The specific synthesis steps are as follows:

[0342] 1) Synthesis of Compound M26: According to the synthesis method of Compound M1-7, Compound M26-2 and twice the amount of Compound M26-1 were used to replace Compound M1-6 and M1-3 respectively, with a yield of 73%. MS (ASAP): 673.

[0343] Synthesis of Compound M27:

[0344]

[0345] The specific synthesis steps are as follows:

[0346] 1) Synthesis of Compound M27: According to the synthesis method of Compound M1-7, Compound M27-1 and M27-2 were used to replace Compound M1-3 and M1-6 respectively, with a yield of 84%. MS (ASAP): 639

[0347] Synthesis of Compound M28:

[0348]

[0349] The specific synthesis steps are as follows:

[0350] 1) Synthesis of Compound M28: According to the synthesis method of Compound M1-7, replace Compound M1-6 and M1-3 with Compound M28-2 and twice the amount of Compound M28-1 respectively, with a yield of 75%. MS(ASAP): 585.

[0351] Synthesis of Compound M29:

[0352]

[0353] The specific synthesis steps are as follows:

[0354] 1) Synthesis of Intermediate M29-2: Under a nitrogen atmosphere, add (30.4 g, 90 mmol) of Compound M29-1 and 150 mL of tetrahydrofuran solvent to a 300 mL three-necked flask, stir to dissolve, cool down to -78 °C, slowly dropwise add 90 mmol of n-butyllithium, stir and react for 1 hour, add (1 g, 30 mmol) of phosphine compound at once, continue to stir and react for 4 hours, rotary evaporate most of the solvent, pour the reaction solution into 300 mL of pure water, extract and wash with dichloromethane 3 times, collect the organic solution, rotary evaporate to dryness, and recrystallize with a mixture of ethyl acetate and ethanol solvents to obtain Intermediate M29-2, with a yield of 73%.

[0355] 2) Synthesis of Compound M29: Add (12.1 g, 15 mmol) of Compound M29-2, 30 mL of hydrogen peroxide and 60 mL of dichloromethane solvent to a 300 mL three-necked flask, stir and react for 4 hours. After the reaction, pour the reaction solution into 200 mL of pure water, extract and wash with dichloromethane 3 times, collect the organic solution, rotary evaporate to dryness, and recrystallize with a mixture of toluene and ethanol solvents to obtain Compound M29, with a yield of 90%. MS(ASAP): 822.

[0356] Synthesis of Compound M30:

[0357]

[0358] The specific synthesis steps are as follows:

[0359] 1) Synthesis of Compound M30: According to the synthesis method of Compound M21, replace Compound M21-2 and M21-1 with (51.4 g, 200 mmol) of Compound M30-1 and (16.4 g, 100 mmol) of Compound M30-2 respectively, with a yield of 74%. MS(ASAP): 639

[0360] Energy Structure of Organic Compounds

[0361] The energy levels of organic materials can be obtained through quantum calculations. For example, using TD-DFT (Time-Dependent Density Functional Theory) via Gaussian09W (Gaussian Inc.). The specific simulation method can be referred to WO2011141110. First, the molecular geometry is optimized using the density functional method "Ground State / DFT / Default Spin / B3LYP / 6-31G(d)" (Charge 0 / Spin Singlet), and then the energy structure of the organic molecule is calculated by the TD-DFT (Time-Dependent Density Functional Theory) method "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated according to the following calibration formulas, and S1 and T1 are used directly.

[0362] HOMO (eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206

[0363] LUMO (eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385

[0364] Where HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 03W, in Hartree. The results are shown in Table 1:

[0365] Table 1

[0366] Material HOMO [eV] LUMO [eV] T1 [eV] S1 [eV] <![CDATA[△E ST [eV]]]> M21 -6.27 -3.58 2.38 2.44 0.06 M22 -5.58 -2.80 2.80 3.02 0.23 M23 -5.57 -2.81 2.81 2.89 0.09 M24 -5.75 -3.15 2.51 2.52 0.01 M25 -5.53 -2.84 2.63 2.71 0.08 M26 -5.53 -2.90 2.48 2.63 0.15 M27 -5.49 -2.91 2.62 2.64 0.02 M28 -5.43 -3.14 2.06 2.30 0.24 M29 -5.57 -2.66 2.73 2.84 0.11 M30 -6.11 -3.40 2.41 2.44 0.03 Ref-1 -5.56 -2.71 1.67 3.46 1.79

[0367] Example 1

[0368] Preparation and Characterization of OLED Devices

[0369] (1) Materials used for each layer of the OLED device:

[0370] Structural formula of the materials used:

[0371] Materials used for the hole injection layer: Materials used for the hole transport layer: Materials used for the electron transport layer: The guest materials for the light-emitting layer are M1 to M20 and Ref-2: The host materials for the light-emitting layer are M21 to M30 and Ref-1: The structure of LiQ is: The structure of the OLED device is:

[0372] ITO / HIL(40nm) / HTL(100nm) / EML(50nm) / ETL(25nm) / LiQ(1nm) / Al(150nm) / Cathode, the preparation steps are as follows:

[0373] a. Cleaning of the conductive glass substrate: When used for the first time, it can be cleaned with various solvents, such as chloroform, ketone, isopropyl alcohol, and then treated with ultraviolet ozone plasma;

[0374] b. Film formation in sequence according to HIL(40nm), HTL(100nm), EML(50nm) by solution processing method; In EML, M1 is selected as the guest material and M29 is selected as the host material, and it is prepared into a film by solution processing method; The weight ratio of the host material to the guest material is: 95:5;

[0375] c. ETL(25nm): Thermally evaporated in a high vacuum of 1×10 -6 mbar;

[0376] d. Cathode: LiQ / Al(1nm / 150nm) thermally evaporated in a high vacuum (1×10 -6 mbar);

[0377] e. Encapsulation: The device is encapsulated with ultraviolet curable resin in a nitrogen glove box.

[0378] Examples 2 to 32, Comparative Examples 1 - 4

[0379] The preparation method is basically the same as that of Example 1, except that the host and guest materials of the light-emitting layer are different, as shown in Table 2 below.

[0380] The current-voltage (J-V) characteristics of the organic light-emitting diodes of Examples 1 to 32 and Comparative Examples 1 - 4 of the device are tested using a characterization device, and important parameters such as efficiency, lifetime (see Table 1) and external quantum efficiency are recorded at the same time. In Table 1, all external quantum efficiencies and lifetimes are relative values relative to the organic light-emitting diode of Comparative Example 1.

[0381] Table 2

[0382]

[0383] As can be seen from Table 1, the light-emitting devices based on the present invention are superior to the comparative examples in terms of light-emitting efficiency and lifetime.

[0384] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of brevity of description, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, it should be considered as the scope described in this specification.

[0385] The embodiments described above merely represent several implementation manners of the present invention. The description is relatively specific and detailed, but it should not be construed as a limitation on the scope of the invention patent. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can still be made, and these all fall within the protection scope of the present invention. Therefore, the protection scope of the present invention patent shall be subject to the appended claims.

Claims

1. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode. The organic functional layer at least includes a light-emitting layer. The light-emitting layer material includes a host material and a guest material. The guest material includes at least one of a compound of formula (I) and a compound of formula (II). The host material includes a compound of formula (III): Among them, Ar 1 is selected from any one of the following groups: Ar 2 selected from the groups represented by formula (B-2); Ar 3 selected from any one of the groups represented by formula (B-2), formula (B-3) and formula (B-6); Ar 4 ~Ar 7 selected from any one of the groups represented by formula (B-2), formula (B-3), formula (B-4) and formula (B-6); X1 is selected from CR5, and R5 is selected from H, tert-butyl or isopropyl; Y is selected from NR6, CR7R8, O or S, R6 is selected from phenyl, tert-butyl or isopropyl, and R7 and R8 are selected from methyl; Each occurrence of X is independently selected from CR1 or N; R1 is selected from H, tert-butyl or isopropyl; Z is selected from NR2, O, S; R2 is selected from phenyl, a group represented by formula (B-2) or formula (B-6); wherein, L is selected from a single bond or phenyl; D is selected from any one of formula (3-1) or formula (3-2): Y2 is selected from a single bond, NR 12 , CR 13 R 14 or O, and R 12 is selected from phenyl, and R 13 and R 14 are each independently selected from phenyl, phenol or methyl; When R 13 and R 14 are selected from phenyl or phenol group, R 13 and R 14 are connected to each other to form a ring; R9 represents a connection site, H or phenyl; R 10 and R 11 represent a linking site or H; Each occurrence of A is independently selected from an electron-withdrawing group; The electron-withdrawing group includes any one of the following groups: Y3 is selected from CR 15 R 16 , R 15 and R 16 are each independently selected from methyl; Y4 is selected from O; X2 is selected from CR 17 or N, and at least one X2 is selected from N; R 17 is selected from phenyl; X3 is selected from CR 18 , R 18 is selected from H or isopropyl; * represents a connection site; m is selected from any integer from 1 to 5; n is selected from any integer from 1 to 5; And the singlet energy level and triplet energy level difference of the compound of formula (III) is less than or equal to 0.3 eV.

2. The organic electroluminescent device according to claim 1, wherein The compound of formula (I) is selected from any one of formula (1-1) to (1-16), and the compound of formula (II) is selected from any one of formula (2-1) to (2-13):

3. The organic electroluminescent device according to claim 1, characterized in that, D is selected from any one of the following groups:

4. The organic electroluminescent device according to claim 1, wherein A is selected from any one of the following groups: wherein, # represents a connection site.

5. The organic electroluminescent device according to claim 2, characterized in that, The compound of formula (III) is selected from any one of (III-1) to (III-7):

6. The organic electroluminescent device according to claim 5, characterized in that, The host material is selected from formula (III-2) or formula (III-4); the guest material is selected from at least one of formula (1-2), formula (2-2), formula (2-7), formula (2-9), formula (2-11) and formula (2-13).

7. The organic electroluminescent device according to claim 5, characterized in that, The host material is selected from at least one of formula (III-a) to (III-c): The guest material is selected from formula (2-7) or formula (2-11).

8. The organic electroluminescent device according to any one of claims 1 to 7, characterized in that, The organic functional layer further includes at least one layer of an electron injection layer, an electron transport layer, an electron blocking layer, a hole injection layer, a hole transport layer and a hole blocking layer.

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