Mixture, composition, and use thereof in electronic device

Abstract

Disclosed is a mixture, comprising: at least one first compound H1 represented by formula (I) and at least one second compound H2, the second compound H2 being preferentially selected from bicarbazole derivatives. An organic compound or mixture of the present invention, when used as a phosphorescent light-emitting host material, can improve the efficiency of devices and the service life of devices. In particular, an organic mixture can strike a good balance between electron holes and electron transport speed, and achieve low efficiency roll-off and a long service life of OLED devices at high brightness. Moreover, the material provided by the invention has a relatively simple synthesis process and is low cost, so that the material has huge application potential and application range. The invention further relates to a composition and an organic electronic device, and in particular relates to an organic electroluminescent device.

Description

A mixture, a composition and its application in organic electronic devices Technical Field

[0001] The present invention relates to the field of electroluminescent materials, in particular to a mixture, a composition containing the mixture, and applications of the mixture in organic electronic devices, in particular in organic electroluminescent devices. Background Art

[0002] Organic semiconductor materials have the characteristics of structural diversity, relatively low manufacturing cost, and excellent optoelectronic properties. They have great potential for application in optoelectronic devices such as organic light-emitting diodes (OLEDs), such as flat panel displays and lighting.

[0003] Organic electroluminescence (OLED) refers to the conversion of electrical energy into light energy using organic substances. OLED elements that utilize this phenomenon typically have a positive electrode and a negative electrode with an organic layer between them. To improve the efficiency and lifespan of OLED elements, the organic layer has a multilayer structure, with each layer containing different organic substances. Specifically, it may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In such an OLED element, 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, which then emit light when they transition back to the ground state. Such OLED elements exhibit characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0004] To improve the luminescence performance of organic light-emitting diodes (OLEDs) and promote their large-scale industrialization, various organic optoelectronic material systems have been extensively developed. The host material plays a crucial role in the luminous efficiency and lifespan of OLED devices. For example, patents such as US2016141505A1, WO2015111848A1, and KR2022139504A disclose triazine or pyrimidine derivatives as host materials. However, the resulting device performance, particularly the lifespan, needs further improvement.

[0005] In order to meet practical requirements, it is necessary to further develop higher performance OLED materials, especially host materials.

[0006] Summary of the Invention

[0007] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a mixture, a composition comprising the same, and applications thereof in organic electronic devices, aiming to solve the problems of poor stability and short device life of existing organic electronic devices.

[0008] The technical solutions of the present invention are as follows:

[0009] A mixture comprising a first compound H1 and a second compound H2, wherein min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T1 (H1), E T1 (H2))+0.1eV, where LUMO(H1), HOMO(H1) and E T1 (H1) are the highest occupied molecular orbital, lowest unoccupied molecular orbital, triplet energy level of the first compound H1, LUMO (H2), HOMO (H2) and E T1 (H2) are the highest occupied orbital, the lowest unoccupied orbital, and the triplet energy level of the second compound H2, respectively; the first compound H1 has the structure shown in formula (I):

[0010] wherein two adjacent * in formula (I) are connected to two * in formula (Ia); X are independently N or CR1, and at least one X is N; Y is the same or different in each case and is CR2 or N, wherein no more than two Ys in each ring are N; Z is independently N or CR3; Ar1 ​​is selected from a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring bonded to the group; R1-R3, when they appear each time, are the same or different and are selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group containing 1 to 10 carbon atoms, a substituted or unsubstituted aromatic ring system or heteroaromatic ring system containing 5 to 60 ring atoms, or a combination thereof.

[0011] The present invention also provides a composition comprising the mixture as described above and at least one organic solvent.

[0012] The present invention also provides an organic electronic device comprising at least one of the above-mentioned mixtures.

[0013] The present invention also provides an organic compound having a structure represented by general formula (VI).

[0014] wherein X is independently N or CR1, and at least one X is N; Y is in each case the same or different and is CR2 or N, wherein not more than two Ys per ring are N; Ar1 ​​is selected from a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded;

[0015] The D ring is represented by the structures shown in the general formula (VI-1) to the general formula (VI-3):

[0016] wherein Z is independently N or CR3; R1-R3, at each occurrence, are the same or different and are selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group containing 1 to 10 carbon atoms, a substituted or unsubstituted aromatic ring system or heteroaromatic ring system containing 5 to 60 ring atoms, or a combination thereof.

[0017] Beneficial Effects: The mixture of the present invention includes a first compound H1 and a second compound H2 capable of forming a composite excited state. The first compound H1 and the second compound H2 exhibit a type II semiconductor heterojunction structure, resulting in excellent stability. The mixture or organic compound of the present invention can be used as a host material or co-host material for electrophosphorescent light. When combined with a suitable guest material, it can improve the luminous efficiency and lifespan of organic electroluminescent devices, thereby providing a material solution for high-efficiency, long-life light-emitting devices. DETAILED DESCRIPTION

[0018] The present invention provides a mixture, a composition containing the same, and use in an organic electroluminescent device. To make the objectives, technical solutions, and effects of the present invention more clear and explicit, the present invention is described in further detail below. It should be understood that the specific embodiments described herein are merely illustrative of the present invention and are not intended to limit the present invention.

[0019] In the present invention, composition, printing ink, or ink have the same meaning and can be used interchangeably.

[0020] In the present invention, main material, matrix material, host or matrix material have the same meaning and can be interchanged.

[0021] In the present invention, metal organic complex, metal organic complex and organometallic complex have the same meaning and can be used interchangeably.

[0022] In this context, a heterojunction refers to the interface region formed by the contact of two different semiconductors. Based on the alignment of the conduction band (LUMO) and valence band (HOMO) of the two materials within the heterojunction, heterojunctions can be divided into Type I and Type II heterojunctions. The fundamental characteristic of a Type II heterojunction is the spatial separation of electrons and holes near the interface and their localization within a self-consistent quantum well. Due to the overlap of wave functions near the interface, the number of optical matrix elements is reduced, thereby extending the radiative lifetime and reducing the exciton binding energy.

[0023] The present invention provides a mixture comprising a first compound H1 and a second compound H2, wherein min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T1 (H1), E T1 (H2))+0.1eV, where LUMO(H1), HOMO(H1) and E T1 (H1) are the highest occupied molecular orbital, lowest unoccupied molecular orbital, triplet energy level of the first compound H1, LUMO (H2), HOMO (H2) and E T1 (H2) are the highest occupied orbital, the lowest unoccupied orbital, and the triplet energy level of the second compound H2, respectively; the first compound H1 has the structure shown in formula (I):

[0024] wherein two adjacent * in formula (I) are connected to two * in formula (Ia); X are independently N or CR1, and at least one X is N; Y is the same or different in each case and is CR2 or N, wherein no more than two Ys in each ring are N; Z is independently N or CR3; Ar1 ​​is selected from a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring bonded to the group; R1-R3, when they appear each time, are the same or different and are selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group containing 1 to 10 carbon atoms, a substituted or unsubstituted aromatic ring system or heteroaromatic ring system containing 5 to 60 ring atoms, or a combination thereof.

[0025] In a preferred embodiment, Ar1 is selected from a substituted or unsubstituted aromatic or heteroaromatic ring having 5 to 30 ring atoms. In a preferred embodiment, Ar1 is selected from a substituted or unsubstituted aromatic or heteroaromatic ring having 5 to 20 ring atoms.

[0026] In a more preferred embodiment, R1-R3, at each occurrence, are selected from hydrogen or deuterium.

[0027] In a preferred embodiment, R1-R3 are identical or different at each occurrence and are substituted or unsubstituted aromatic or heteroaromatic ring systems containing 5 to 50 ring atoms, or combinations thereof. In a preferred embodiment, R1-R3 are identical or different at each occurrence and are substituted or unsubstituted aromatic or heteroaromatic ring systems containing 5 to 40 ring atoms, or combinations thereof. In a preferred embodiment, R1-R3 are identical or different at each occurrence and are substituted or unsubstituted aromatic or heteroaromatic ring systems containing 5 to 30 ring atoms, or combinations thereof.

[0028] In a preferred embodiment, the aromatic ring system comprises 5 to 25 ring atoms in the ring system, and the heteroaromatic ring system comprises 5 to 25 ring atoms and at least one heteroatom in the ring system, provided that the total number of carbon atoms and heteroatoms is at least 5. In a more preferred embodiment, the aromatic ring system comprises 5 to 20 ring atoms in the ring system, and the heteroaromatic ring system comprises 5 to 20 ring atoms and at least one heteroatom in the ring system. In a more preferred embodiment, the aromatic ring system comprises 5 to 16 ring atoms in the ring system, and the heteroaromatic ring system comprises 5 to 16 ring atoms and at least one heteroatom in the ring system. The heteroatoms are preferably selected from Si, N, P, O, S and / or Ge, and particularly preferably selected from Si, N, P, O and / or S.

[0029] An aromatic ring system or aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including monocyclic and polycyclic ring systems. A heteroaromatic ring system or heteroaromatic group refers to a hydrocarbon group (containing heteroatoms) containing at least one heteroaromatic ring, including monocyclic and polycyclic ring systems. These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. At least one of these polycyclic rings is aromatic or heteroaromatic. For the purposes of this invention, an aromatic or heteroaromatic ring system includes not only systems containing aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups are interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N, or O atoms). Thus, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, and diaryl ethers are also considered aromatic ring systems for the purposes of this invention.

[0030] Specific examples of the aromatic group are benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, pyrene, benzopyrene, triphenylene, acenaphthene, fluorene, and derivatives thereof.

[0031] Specific examples of heteroaromatic groups include furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-naphthyridine, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, and derivatives thereof.

[0032] In certain embodiments, the first compound H1 is selected from the following structures represented by formula (I-1) to formula (I-10):

[0033] Wherein, X, Y, Ar1, and Z are as defined above;

[0034] Wherein Ar1 in formula (1-5) and (1-10) is selected from the following groups: wherein Y is as defined above.

[0035] In certain preferred embodiments, according to the mixture of the present invention, wherein Ar1 in the first compound H1 is selected from one or a combination of the following groups:

[0036] When V occurs multiple times, it is independently selected from CR4 or N;

[0037] W, when present multiple times, is independently selected from CR5R6, SiR7R8, NR9, C(=O), S or O;

[0038] R4-R9, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, or a substituted or unsubstituted silyl group, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, an amino group, or a substituted or unsubstituted silyl group. 40 ring atoms, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which the groups are bonded.

[0039] In another more preferred embodiment, Ar1 comprises the following structural formula and may be substituted by 0, 1, 2 or 3 groups selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl and C3-C10 cycloalkyl:

[0040] Among them, R 12 、R 13 The definition of is the same as above R4.

[0041] In a more preferred embodiment, no more than 3 Zs are N, preferably no more than 2 Zs are N, more preferably no more than 1 Z is N, and most preferably no more than 3 Zs are CH.

[0042] In certain embodiments, in the mixture according to the present invention, the first compound H1 and / or the first compound H2 has a higher triplet energy level E T1 , usually E T1 ≥2.2eV, preferably E T1 ≥2.4eV, preferably E T1 ≥2.5eV, better is E T1 ≥2.6eV, the best is E T1 ≥2.8eV.

[0043] In a more preferred embodiment, in the mixture according to the present invention, the first compound H1 and / or the first compound H2 is at least partially deuterated, preferably 10% or more of the H is deuterated, more preferably 20% or more of the H is deuterated, most preferably 30% or more of the H is deuterated, and most preferably 40% or more of the H is deuterated.

[0044] In certain embodiments, the mixture according to the present invention facilitates the realization of thermally activated delayed fluorescence effect, wherein the first compound H1 and / or the first compound H2 have a ΔE (E S1 -E T1 ) is small enough to allow triplet excitons to undergo reverse internal conversion to singlet excitons, resulting in efficient luminescence. Generally speaking, such materials are formed by linking electron-donating (Donor) groups with electron-deficient or electron-withdrawing (Acceptor) groups, i.e., they have a distinct DA structure.

[0045] Preferred examples of the first compound H1 in the mixture according to the invention are the following structures, which may be substituted at all possible substitution points.

[0046] In a preferred embodiment, the mixture according to the present invention is used in vapor-deposited OLED devices. For this purpose, the first compound H1 and / or the second compound H2 in the mixture according to the present invention have a molecular weight of ≤1000 g / mol, preferably ≤900 g / mol, very preferably ≤850 g / mol, more preferably ≤800 g / mol, and most preferably ≤750 g / mol.

[0047] In certain preferred embodiments, the mixture, wherein the first compound H1 and the second compound H2 form a type II heterojunction structure.

[0048] In a preferred embodiment, the mixture, wherein min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T1 (H1), E T1 (H2))+0.05eV.

[0049] In another preferred embodiment, the mixture, wherein min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T1 (H1), E T1 (H2)).

[0050] In a more preferred embodiment, the mixture, wherein min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T1 (H1), E T1 (H2))-0.05eV.

[0051] In a more preferred embodiment, the mixture, wherein min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T1 (H1), E T1 (H2))-0.1eV.

[0052] In a very preferred embodiment, the mixture, wherein min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T (H1), E T1 (H2))-0.15eV.

[0053] In a most preferred embodiment, the mixture, wherein min((LUMO(H1)-HOMO(H2), LUMO(H2)-HOMO(H1))≤min(E T1 (H1), E T1 (H2))-0.2eV.

[0054] In other embodiments, the mixture, wherein the first compound H1 and the second compound H2 form an I-type heterojunction structure; preferably, the energy gap of the second compound H2 is larger than that of the first compound H1. In some more preferred embodiments, the ΔE (E S1 -E T1 )≤0.3eV, preferably ≤0.2eV, most preferably ≤0.1eV.

[0055] In the embodiment of the present invention, the energy level structure of the organic material, the singlet energy level E S1 , triplet energy level E T1 , HOMO, and LUMO play a key role. The following is an introduction to the determination of these energy levels.

[0056] HOMO and LUMO energy levels can be measured by photoelectric effects, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or by cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0057] The singlet energy level E of organic materials S1 The triplet energy level E can be determined by the luminescence spectrum. T1 It can be measured by low-temperature time-resolved luminescence spectroscopy, E S1 and E T1 It can also be obtained by quantum simulation calculation (such as by Time-dependent DFT), such as by the commercial software Gaussian09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110 or described below in the examples.

[0058] It should be noted that HOMO, LUMO, E S1 、E T1 The absolute value of depends 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. S1 、ET1 The values ​​are based on Time-dependent DFT simulations and do not affect the application of other measurement or calculation methods.

[0059] In the mixture according to the present invention, one possible benefit is that the excited state of the system will preferentially occupy the lowest energy composite excited state or facilitate the energy transfer of the triplet excited state on the first compound H1 or the second compound H2 to the composite excited state, thereby increasing the concentration of the composite excited state.

[0060] In a preferred embodiment, the mixture according to the invention serves as phosphorescent host material.

[0061] In the present invention, (HOMO-1) is defined as the second-highest occupied molecular orbital energy level, (HOMO-2) is the third-highest occupied molecular orbital energy level, and so on. (LUMO+1) is defined as the second-lowest unoccupied molecular orbital energy level, (LUMO+2) is the third-lowest occupied molecular orbital energy level, and so on.

[0062] In a preferred embodiment, the mixture according to the present invention is characterized in that min((LUMO H1 -HOMO H2 ), (LUMO H2 -HOMO H1 )) is less than or equal to the triplet excited state energy level of the first compound H1 and the triplet excited state energy level of the second compound H2. The energy of the composite excited state formed by the first compound H1 and the second compound H2 depends on min((LUMO H1 -HOMO H2 ), (LUMO H2 -HOMO H1 )).

[0063] In certain embodiments, according to the mixture of the present invention, at least one of the first compound H1 and the second compound H2 has a (HOMO-(HOMO-1)) ≥ 0.2 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, even better ≥ 0.35 eV, very preferably ≥ 0.4 eV, and most preferably ≥ 0.45 eV.

[0064] In a preferred embodiment, the second compound H2 is an organic compound containing an electron-donating group. A possible benefit of such a combination is that the first compound H1 and the second compound H2 are likely to form a type II semiconductor heterojunction.

[0065] In a more preferred embodiment, according to the mixture of the present invention, the (HOMO-(HOMO-1)) of the second compound H2 is ≥0.2eV, preferably ≥0.25eV, better ≥0.3eV, even better ≥0.35eV, very best ≥0.4eV, and most preferably ≥0.45eV.

[0066] In a more preferred embodiment, in the mixture, the second compound H2 is selected from the compounds represented by one of the following chemical formulas (II) to (V):

[0067] Where: L 1 represents an aromatic group or aromatic hetero group having 5 to 60 ring atoms; L 2 represents a single bond, an aromatic group or an aromatic hetero group having 5 to 30 ring atoms, L 1 , L 2 The connection position of Ar can be on any carbon atom on the benzene ring; 4 、Ar 5 、Ar 6 、Ar 7 、Ar 8 、Ar 9 Each independently represents an aromatic group or aromatic hetero group having 5 to 30 ring atoms; X 1 represents a single bond, N(R), C(R)2, Si(R)2, O, C=N(R), C=C(R)2, P(R), P(=O)R, S, S=O or SO2; X 2 、X 3 、X 4 、X 5 、X 6 、X 7 、X 8 、X 9 Each independently represents a single bond, N(R), C(R)2, Si(R)2, O, C=N(R), C=C(R)2, P(R), P(=O)R, S, S=O or SO2, but X 2 and X 3 Not single bond at the same time, X 4 and X 5 Not single bond at the same time, X 6 and X 7 Not single bond at the same time, X 8 and X 9 Not single bond at the same time; R 1 、R 2R and R independently represent H, D, F, CN, alkenyl, alkynyl, nitrile, amino, nitro, acyl, alkoxy, carbonyl, sulfone, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, aromatic hydrocarbon or aromatic heterocyclic group having 5 to 60 ring atoms, wherein R 1 、R 2 The connection position can be any carbon atom on the condensed ring, and R 1 、R 2 The number of substituted carbon atoms may be arbitrary; n1 represents an integer of 1 to 4.

[0068] In a very preferred embodiment, the second compound H2 has a structure shown by one of formula (II-1) to formula (V-1):

[0069] Among them, X 2 -X 4 , L 1 、R 1 、R 2 The definitions of n1 and L2 are the same as above; the definitions of L3 and L 1 ; A 1 、A 2 Each independently represents an aromatic group or aromatic hetero group having 5 to 30 ring atoms; Y1-Y8 each independently represents N or CR, and two adjacent Y1-Y8 are not N at the same time.

[0070] Preferably, the second compound H2 represented by formula (II-1) to (V-1) is selected from one of the following structural formulas:

[0071] In a preferred embodiment, the mixture according to the present invention can be used as a host material of the light-emitting layer in an organic electroluminescent device, wherein min((LUMO H1 -HOMO H2 ), (LUMO H2 -HOMO H1 )) is less than or equal to the triplet excited state energy level of the first compound H1 and the triplet excited state energy level of the second compound H2.

[0072] When a single material with electron-biased or hole-biased characteristics is used to form the light-emitting layer, a relatively high number of excitons can form at the interface between the light-emitting layer and the electron-transport layer and the hole-transport layer. Consequently, these excitons in the light-emitting layer may interact with interfacial charges in the electron-transport layer or the hole-transport layer, causing a sharp drop in device efficiency at high brightness and shortening device lifetime. To address this issue, a mixture of the first compound H1 and the second compound H2 is introduced into the light-emitting layer to balance the mobility of holes and electrons in the light-emitting layer, locating the emission region in the center of the light-emitting layer, thereby improving device efficiency and lifetime. The preferred mass ratio of the first compound H1 and the second compound H2 to form a mixture is 2:8 to 8:2, more preferably 3:7 to 7:3, even more preferably 4:6 to 6:4, most preferably 4.5:5.5 to 5.5:4.5, and most preferably 5:5.

[0073] In a preferred embodiment, the first compound H1 and the second compound H2 according to the present invention are small molecule materials, and the mixture of the present invention is also a small molecule mixture.

[0074] As defined herein, the term "small molecule" refers to a molecule that is not a polymer, oligomer, dendrimer, or blend. In particular, a small molecule lacks a repeating structure. A small molecule has a molecular weight of ≤4000 g / mole, preferably ≤3000 g / mole, more preferably ≤2000 g / mole, and most preferably ≤1500 g / mole.

[0075] Polymers include homopolymers, copolymers, and block copolymers. In the present invention, polymers also include dendrimers. For information on the synthesis and application of dendrimers, please refer to [Dendrimers and Dendrons, Wiley-VCH Verlag GmbH & Co. KGaA, 2002, Ed. George R. Newkome, Charles N. Moorefield, Fritz Vogtle.].

[0076] Conjugated polymer is a polymer whose main chain backbone is mainly composed of sp 2 Hybrid orbitals are formed. Famous examples include polyacetylene and poly(phenylenevinylene). The C atoms on the main chain can also be replaced by other non-C atoms, and when the sp 2When hybridization is interrupted by some natural defects, it is still considered a conjugated polymer. In addition, the conjugated polymers in the present invention also include those containing arylamine, arylphosphine, other heteroaromatics, organometallic complexes, etc. in the main chain.

[0077] In certain embodiments, to improve material evaporation efficiency, enhance material utilization, and simplify the material evaporation process, the molecular weight difference between the first compound H1 and the second compound H2 is less than or equal to 100 Dalton. Preferably, the molecular weight difference is less than or equal to 90 Dalton, more preferably less than or equal to 70 Dalton, even more preferably less than or equal to 560 Dalton, most preferably less than or equal to 50 Dalton, and most preferably less than or equal to 20 Dalton.

[0078] In certain embodiments, in the mixture according to the present invention, the difference in sublimation temperature between the first compound H1 and the second compound H2 is less than or equal to 40 K. Preferably, it is less than or equal to 30 K, more preferably, it is less than or equal to 25 K, even more preferably, it is less than or equal to 20 K, most preferably, it is less than or equal to 18 K, and most preferably, it is less than or equal to 15 K.

[0079] Examples of second compounds H2 according to the invention are the following structures, which can be substituted at all possible substitution points.

[0080] The present invention also relates to an organic compound having a structure shown in general formula (VI):

[0081] wherein X is independently N or CR1, and at least one X is N; Y is in each case the same or different and is CR2 or N, wherein not more than two Ys per ring are N; Ar1 ​​is selected from a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded;

[0082] The D ring is represented by the structure shown in the general formula (VI-1) to (VI-3):

[0083] wherein Z is independently N or CR3; R1-R3, at each occurrence, are the same or different and are selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group containing 1 to 10 carbon atoms, a substituted or unsubstituted aromatic ring system or heteroaromatic ring system containing 5 to 60 ring atoms, or a combination thereof.

[0084] In certain preferred embodiments, according to the organic compound of the present invention, wherein Ar1 is selected from one or a combination of the following groups:

[0085] When V occurs multiple times, it is independently selected from CR4 or N;

[0086] W, when present multiple times, is independently selected from CR5R6, SiR7R8, NR9, C(=O), S or O;

[0087] R4-R9, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms, or a substituted or unsubstituted silyl group, or a substituted keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, an amino group, or a substituted or unsubstituted silyl group. 40 ring atoms, or a substituted or unsubstituted aromatic or heteroaromatic ring system having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which the groups are bonded.

[0088] In another more preferred embodiment, Ar1 comprises the following structural formula and may be substituted by 0, 1, 2 or 3 groups selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl and C3-C10 cycloalkyl:

[0089] Among them, R 12 、R 13 Same as above R4.

[0090] In a more preferred embodiment, no more than 3 Z's in the D ring are N, preferably two are N, more preferably one is N, and most preferably all Z's are CH.

[0091] Preferred examples of the organic compounds according to the present invention are the following structures, which may be substituted at all possible substitution points.

[0092] The present invention also relates to a polymer, wherein at least one repeating unit comprises a structure as shown in formula (VI). In certain embodiments, the polymer is a non-conjugated polymer, wherein the structural unit as shown in formula (VI) is on a side chain. In another preferred embodiment, the polymer is a conjugated polymer.

[0093] The present invention also relates to another mixture, including a mixture and at least another organic functional material. The other organic functional material includes a hole (also known as a hole) injection or transport material (HIM / HTM), a hole blocking material (HBM), an electron injection or transport material (EIM / ETM), an electron blocking material (EBM), an organic host material (Host), a singlet light emitter (fluorescent light emitter), a heavy light emitter (phosphorescent light emitter), an organic thermally excited delayed fluorescence material (TADF material), and in particular a luminescent organometallic complex. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference. The organic functional material can be a small molecule or a polymer material.

[0094] In a preferred embodiment, the other mixture comprises a mixture according to the present invention and a phosphorescent emitter. Here, the mixture according to the present invention can be used as the main body, wherein the weight percentage of the phosphorescent emitter is ≤20wt%, preferably ≤15wt%, and more preferably ≤10wt%.

[0095] In another preferred embodiment, the other mixture comprises a mixture according to the present invention and a fluorescent light emitter. Here, the mixture according to the present invention can be used as a fluorescent host material, wherein the weight percentage of the fluorescent light emitter is ≤15wt%, preferably ≤10wt%, and more preferably ≤8wt%.

[0096] In a preferred embodiment, the other mixture comprises a mixture according to the present invention, a phosphorescent emitter, and a phosphorescent host material. In this embodiment, the mixture according to the present invention can be used as an auxiliary luminescent material, and the weight ratio of the mixture to the phosphorescent emitter is from 1:2 to 2:1.

[0097] In another preferred embodiment, the other mixture comprises a mixture according to the present invention and a TADF material. Here, the mixture according to the present invention can be used as the main material of TADF, wherein the weight percentage of the TADF material is ≤ 15 wt%, preferably ≤ 10 wt%, and more preferably ≤ 8 wt%.

[0098] For detailed descriptions of phosphorescent host materials, phosphorescent luminescent materials, fluorescent host materials, fluorescent luminescent materials and TADF materials, please refer to WO2018095395. The entire contents of this patent document are hereby incorporated herein by reference.

[0099] Another object of the present invention is to provide a material solution for printed OLEDs.

[0100] For this purpose, the organic compounds or the first compound H1 or the second compound H2 in the mixture according to the invention have a molecular weight of ≥700 g / mol, preferably ≥800 g / mol, very preferably ≥900 g / mol, more preferably ≥1000 g / mol and most preferably ≥1100 g / mol.

[0101] In certain embodiments, the solubility of the organic compound or mixture according to the present invention in any one solvent of toluene, xylene, mesitylene, cyclohexylbenzene, or methyl benzoate, or a mixture of any two or more thereof at 25° C. is ≥10 mg / mL, preferably ≥15 mg / mL, and most preferably ≥20 mg / mL.

[0102] The present invention further relates to a composition or ink comprising an organic compound or mixture as described above and at least one organic solvent.

[0103] When used in printing processes, ink viscosity and surface tension are important parameters. The appropriate surface tension parameters of the ink are suitable for a specific substrate and a specific printing method.

[0104] In a preferred embodiment, the surface tension of the ink according to the present invention at operating temperature or at 25°C is approximately in the range of 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; and most preferably in the range of 25 dyne / cm to 33 dyne / cm.

[0105] In another preferred embodiment, the viscosity of the ink according to the present invention at operating temperature or 25° C. is in the range of about 1 cps to 100 cps; more preferably, in the range of 1 cps to 50 cps; more preferably, in the range of 1.5 cps to 20 cps; and most preferably, in the range of 4.0 cps to 20 cps. Such a formulated composition will facilitate inkjet printing.

[0106] Viscosity can be adjusted by various methods, such as by selecting the appropriate solvent and adjusting the concentration of the functional material in the ink. The ink containing the mixture according to the present invention facilitates adjusting the printing ink within an appropriate range according to the printing method used. Generally, the weight ratio of the functional material contained in the composition of the present invention is in the range of 0.3% to 30% by weight, preferably in the range of 0.5% to 20% by weight, more preferably in the range of 0.5% to 15% by weight, even more preferably in the range of 0.5% to 10% by weight, and most preferably in the range of 1% to 5% by weight.

[0107] In some embodiments, according to the ink of the present invention, the at least one organic solvent is selected from aromatic or heteroaromatic based solvents, in particular aliphatic chain / ring substituted aromatic solvents, or aromatic ketone solvents, or aromatic ether solvents.

[0108] Examples of solvents suitable for the present invention include, but are not limited to: aromatic or heteroaromatic based solvents: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-xylene, m-xylene, p-xylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, 1-methoxynaphthalene, cyclohexylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1 , 2,4-trichlorobenzene, 1,3-dipropoxybenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, dibenzyl ether, etc.; ketone-based solvents: 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylphenylacetone Ketone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, isophorone, 2,6,8-trimethyl-4-nonanone, fenchone, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, phorone, di-n-amyl ketone; aromatic ether solvents: 3-phenoxytoluene, butoxybenzene, benzylbutylbenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylphenyl ether, 1,2,4-trimethyl Oxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether; ester solvents: octanoic acid alkyl esters, sebacate alkyl esters, stearic acid alkyl esters, Alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc.

[0109] Further, according to the ink of the present invention, the at least one organic solvent can be selected from: aliphatic ketones, for example, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, phorone, di-n-amyl ketone, etc.; or aliphatic ethers, for example, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0110] In some other embodiments, the ink further comprises another organic solvent. Examples of the other organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene, and / or mixtures thereof.

[0111] In a preferred embodiment, the composition according to the present invention is a solution.

[0112] In another preferred embodiment, the composition according to the present invention is a suspension.

[0113] The composition in the embodiment of the present invention may include 0.01 to 20 wt% of the organic compound or mixture according to the present invention, preferably 0.1 to 15 wt%, more preferably 0.2 to 10 wt%, and most preferably 0.25 to 5 wt% of the organic compound or mixture.

[0114] The present invention also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices, and particularly preferably a preparation method by printing or coating.

[0115] Suitable printing or coating techniques include, but are not limited to, gravure printing, inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roll printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush or pad printing, slot die coating, and the like. Gravure printing, nozzle printing, and inkjet printing are preferred. The solution or suspension may further include one or more components, such as a surfactant, lubricant, wetting agent, dispersant, hydrophobic agent, adhesive, etc., to adjust viscosity, film-forming properties, and enhance adhesion. For detailed information on printing techniques and their requirements for the relevant solutions, such as solvent concentration, viscosity, etc., please refer to "Handbook of Print Media: Technologies and Production Methods," edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0116] The present invention also provides a use of the organic compound or mixture described above, i.e., applying the organic compound or mixture to an organic electronic device. The organic electronic device may be selected from, but not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLED), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode (OPED), particularly an OLED. In embodiments of the present invention, the mixture or organic compound is preferably used in the light-emitting layer of an OLED device.

[0117] The present invention further relates to an organic electronic device comprising at least one organic compound or mixture as described above. Generally, such an organic electronic device comprises at least a cathode, an anode, and a functional layer located between the cathode and the anode, wherein the functional layer comprises at least one mixture as described above. The organic electronic device may be selected from, but not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors (OLEDs), organic lasers, organic spintronic devices, organic sensors, organic plasmon emitting diodes (OPEDs), and the like. Particularly preferred are organic electroluminescent devices, such as OLEDs, OLEECs, and OLEDs.

[0118] In certain particularly preferred embodiments, the organic electronic device is an organic electroluminescent device and comprises a light-emitting layer, an electron transport layer, or a hole blocking layer. In certain particularly preferred embodiments, the light-emitting layer of the organic electroluminescent device comprises one of the organic compounds or mixtures, or comprises one of the organic compounds or mixtures and a phosphorescent emitter, or comprises one of the organic compounds or mixtures and a host material, or comprises one of the organic compounds or mixtures, a phosphorescent emitter, and a phosphorescent host material. In other particularly preferred embodiments, the electron transport layer of the organic electroluminescent device comprises one of the organic compounds or mixtures. In other particularly preferred embodiments, the hole blocking layer of the organic electroluminescent device comprises one of the organic compounds or mixtures.

[0119] The light-emitting device described above, in particular the OLED, includes a substrate, an anode, at least one light-emitting layer, and a cathode.

[0120] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting element. For example, see Bulovic et al. Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or elastic. The substrate can be plastic, metal, semiconductor wafer or glass. It is best if the substrate has a smooth surface. Substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is flexible and can be selected from a polymer film or plastic with a glass transition temperature Tg of above 150°C, preferably above 200°C, more preferably above 250°C, and most preferably above 300°C. Examples of suitable flexible substrates are polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0121] The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can readily inject holes into the hole injection layer (HIL) or 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 energy level or valence band energy level of the light-emitting material in the light-emitting layer or the p-type semiconductor material serving as the HIL or 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), and the like. Other suitable anode materials are known and can be readily selected for use by one 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), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

[0122] The cathode may comprise a conductive metal or metal oxide. The cathode can readily inject electrons into the EIL or ETL or directly into the light-emitting layer. In one embodiment, the absolute difference between the work function of the cathode and the LUMO energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), 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 cathodes in OLEDs may be used as cathode materials for the devices of the present invention. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material may 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), and the like.

[0123] OLEDs may also include other functional layers, such as 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 use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated by reference.

[0124] In another preferred embodiment, in the organic electroluminescent device according to the present invention, its electron transport layer (ETL) or hole blocking layer (HBL) comprises a mixture, organic compound, or polymer according to the present invention. In a preferred embodiment, in the light-emitting device according to the present invention, its light-emitting layer is prepared from the composition according to the present invention.

[0125] In a preferred embodiment, in the organic electroluminescent device according to the present invention, the light-emitting layer comprises the organic compound, mixture or polymer according to the present invention. The light-emitting layer can be preferably prepared by a method comprising the following two steps:

[0126] (1) A mixture comprising the first compound H1 and the second compound H2 is deposited as a source. This can be prepared by printing the composition according to the present invention, or by vacuum evaporating the mixture as a source.

[0127] (2) The first compound H1 and the second compound H2 are deposited from two separate sources.

[0128] In some particularly preferred embodiments, the molecular weights of the first compound H1 and the second compound H2 differ slightly, and their sublimation temperatures are correspondingly low. In order to further simplify the material evaporation process and reduce the production cost of OLED display devices, when preparing the light-emitting layer using the mixture according to the present invention, the two main materials, the first compound H1 and the second compound H2, can be first mixed uniformly according to a certain ratio and then evaporated using a single evaporation heat source.

[0129] According to the light emitting device of the present invention, the light emission wavelength is between 300nm and 1000nm, preferably between 350nm and 900nm, and more preferably between 400nm and 800nm.

[0130] The present invention also relates to applications of the organic electronic device according to the present invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0131] The present invention also relates to electronic devices comprising the organic electronic device according to the present invention, including, but not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0132] Example

[0133] 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 summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should realize 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.

[0134] Synthesis of the second compound H2 (i.e., the second organic host material)

[0135] Example 1, Synthesis of Compound 1:

[0136] Under a nitrogen atmosphere, 1-2 (3.63 g, 10 mmol), 1-1 (3.98 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), 100 mL of toluene, 25 mL of water, and 25 mL of ethanol were added sequentially to a 250 mL three-necked flask. The reaction was heated to 110°C and the reaction progress was monitored by TLC. After the reaction was completed, the mixture was cooled to room temperature. The reaction solution was poured into water, washed to remove K2CO3, and then filtered to obtain a solid product, which was washed with dichloromethane. The crude product was recrystallized from dichloromethane and methanol to obtain 5.8 g of compound 1, MS (ASAP) = 637.4.

[0137] Example 2, Synthesis of Compound 2:

[0138] Under a nitrogen atmosphere, 2-1 (3.63 g, 10 mmol), 1-1 (3.98 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), 100 mL of toluene, 25 mL of water, and 25 mL of ethanol were added sequentially to a 250 mL three-necked flask. The mixture was heated to 110°C for reaction. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature. The reaction solution was poured into water, washed to remove K2CO3, and then filtered to obtain a solid product, which was washed with dichloromethane. The crude product was recrystallized from dichloromethane and methanol to obtain 5.4 g of compound 2, MS (ASAP) = 637.8.

[0139] Example 3, synthesis of compound 3:

[0140] Under a nitrogen atmosphere, 1-2 (3.63 g, 10 mmol), 3-1 (3.98 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), 100 mL of toluene, 25 mL of water, and 25 mL of ethanol were added sequentially to a 250 mL three-necked flask. The reaction was heated to 110°C and the reaction progress was monitored by TLC. After the reaction was completed, the mixture was cooled to room temperature. The reaction solution was poured into water, washed to remove K2CO3, and then filtered to obtain a solid product, which was washed with dichloromethane. The crude product was recrystallized from dichloromethane and methanol to obtain 5.4 g of compound 3, MS (ASAP) = 636.6.

[0141] Example 4, Synthesis of Compound 4:

[0142] Under a nitrogen atmosphere, 1-2 (3.63 g, 10 mmol), 4-1 (3.98 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), 100 mL of toluene, 25 mL of water, and 25 mL of ethanol were added sequentially to a 250 mL three-necked flask. The mixture was heated to 110°C for reaction. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature. The reaction solution was poured into water, washed to remove K2CO3, and then filtered to obtain a solid product, which was washed with dichloromethane. The crude product was recrystallized from dichloromethane and methanol to obtain 5.5 g of compound 4, MS (ASAP) = 637.4.

[0143] Example 5, Synthesis of Compound 5:

[0144] Under a nitrogen atmosphere, 1-2 (3.63 g, 10 mmol), 5-1 (3.98 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), 100 mL of toluene, 25 mL of water, and 25 mL of ethanol were added sequentially to a 250 mL three-necked flask. The mixture was heated to 110°C for reaction. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature. The reaction solution was poured into water, washed to remove K2CO3, and then filtered to obtain a solid product, which was washed with dichloromethane. The crude product was recrystallized from dichloromethane and methanol to obtain 6.2 g of compound 5, MS (ASAP) = 636.2.

[0145] Example 6, Synthesis of Compound 6:

[0146] Under a nitrogen atmosphere, 6-1 (3.63 g, 10 mmol), 6-2 (3.98 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), 100 mL of toluene, 25 mL of water, and 25 mL of ethanol were added sequentially to a 250 mL three-necked flask. The mixture was heated to 110°C for reaction. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature. The reaction solution was poured into water, washed to remove K2CO3, and then filtered to obtain a solid product, which was washed with dichloromethane. The crude product was recrystallized from dichloromethane and methanol to obtain 5.2 g of compound 6, MS (ASAP) = 484.6.

[0147] Example 7, Synthesis of Compound 7:

[0148] Under a nitrogen atmosphere, 7-1 (3.63 g), 7-2 (3.98 g), potassium carbonate (6.9 g, 50 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), 100 mL of toluene, 25 mL of water, and 25 mL of ethanol were added sequentially to a 250 mL three-necked flask. The mixture was heated to 110°C for reaction. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature. The reaction solution was poured into water, washed to remove K2CO3, and then filtered to obtain a solid product, which was washed with dichloromethane. The crude product was recrystallized from dichloromethane and methanol to obtain 3.2 g of compound 7, MS (ASAP) = 725.9.

[0149] Example 8, Synthesis of Compound 8:

[0150] Under a nitrogen atmosphere, 7-1 (3.63 g), 8-1 (3.98 g), potassium carbonate (6.9 g, 50 mmol), Pd(PPh3)4 (0.58 g, 0.5 mmol), 100 mL of toluene, 25 mL of water, and 25 mL of ethanol were added sequentially to a 250 mL three-necked flask. The mixture was heated to 110°C for reaction. The reaction progress was monitored by TLC. After completion, the mixture was cooled to room temperature. The reaction solution was poured into water and washed to remove K2CO3. The solid product was then filtered and washed with dichloromethane. The crude product was recrystallized from dichloromethane and methanol to yield 4.3 g of compound 8, with MS (ASAP) = 757.9.

[0151] Synthesis of the first compound H1 (i.e., the first organic host material)

[0152] Synthesis of intermediate 1b:

[0153] In a dry three-necked flask, 1c (18 g), pinacol diboronate (20 g), potassium acetate (15 g), catalyst Pd(dppf)Cl2 (1 g), and 300 mL of toluene were added. The atmosphere was replaced with nitrogen three times, and the mixture was heated to 100°C. Stirring and refluxed for 24 h before the reaction was terminated. Column chromatography (petroleum ether / ethyl acetate 25:1) was used to obtain 19.5 g of intermediate 1b. The yield was 89%. The molecular mass of the product, as determined by mass spectrometry, was 384 (calculated: 384.24).

[0154] Synthesis of intermediate 4b:

[0155] In a dry three-necked flask, 4a (20 g), pinacol diboronate (20 g), potassium acetate (15 g), catalyst Pd(dppf)Cl2 (1 g), and 300 mL of toluene were added. The atmosphere was replaced with nitrogen three times, and the reaction was heated to 100°C. Stirring and refluxed for 24 h before terminating the reaction. Column chromatography (petroleum ether / ethyl acetate 25:1) afforded 16 g of intermediate 4b. The yield was 75%. Mass spectrometry analysis confirmed a molecular mass of 384 (calculated: 384.24).

[0156] Synthesis of intermediate 5b:

[0157] In a dry three-necked flask, 5a (20 g), pinacol diboronate (20 g), potassium acetate (15 g), catalyst Pd(dppf)Cl2 (1 g), and 300 mL of toluene were added. The atmosphere was replaced with nitrogen three times, and the mixture was heated to 100°C. The reaction was stirred and refluxed for 24 h. The reaction was terminated and separated by column chromatography (petroleum ether / ethyl acetate 25:1) to obtain 14.5 g of intermediate 5b. The yield was 68%. The molecular mass of the product, determined by mass spectrometry, was 384 (calculated value: 384.24).

[0158] Synthesis of intermediate 13b:

[0159] In a dry three-necked flask, 13a (18 g), pinacol diboronate (20 g), potassium acetate (15 g), catalyst Pd(dppf)Cl2 (1 g), and 300 mL of toluene were added. The atmosphere was replaced with nitrogen three times, and the mixture was heated to 100°C and refluxed with stirring for 24 h. The reaction was terminated and separated by column chromatography (petroleum ether / ethyl acetate 25:1) to obtain 20.1 g of intermediate 13b. The yield was 91%. The molecular mass of the product, as determined by mass spectrometry, was 384 (calculated: 384.24).

[0160] Synthesis of intermediate 19b:

[0161] In a dry three-necked flask, 13a (18 g), pinacol diboronate (20 g), potassium acetate (15 g), catalyst Pd(dppf)Cl2 (1 g), and 300 mL of toluene were added. The atmosphere was replaced with nitrogen three times, and the mixture was heated to 100°C and refluxed with stirring for 24 h. The reaction was terminated and separated by column chromatography (petroleum ether / ethyl acetate 25:1) to obtain 20.1 g of intermediate 13b. The yield was 91%. The molecular mass of the product, as determined by mass spectrometry, was 384 (calculated: 384.24).

[0162] Example 9, Synthesis of Compound 9:

[0163] Under nitrogen, 1a (30 g), 1b (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 hours, and the temperature was then lowered. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 28 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 25.7 g of compound 9. The yield was 87%. Mass spectrometry analysis determined the molecular mass of the product to be 579 (calculated: 578.63).

[0164] Example 10, Synthesis of Compound 10:

[0165] Under nitrogen, 2a (30 g), m-pyridine boronic acid (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The mixture was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 25 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 22.6 g of 2b. The yield was 70%. Mass spectrometry confirmed the molecular ion mass to be 358 (calculated mass: 357.8).

[0166] Under nitrogen, 2b (30 g), 1b (35 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 28 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 25.8 g of compound 10. The yield was 87%, and the molecular mass determined by mass spectrometry was 579 (calculated value: 579.6).

[0167] Example 11, Synthesis of Compound 11:

[0168] Under nitrogen, 3a (30 g), 1b (35 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 27.3 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 26.5 g of compound 11. The yield was 85%. Mass spectrometry analysis determined the molecular mass of 667 (calculated value: 667.73).

[0169] Example 12, Synthesis of Compound 12:

[0170] Under nitrogen, 1a (30 g), 4b (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 26 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 23.6 g of compound 12. The yield was 82%. Mass spectrometry analysis determined the molecular mass of the product to be 579 (calculated value: 578.63).

[0171] Example 13, Synthesis of Compound 13:

[0172] Under nitrogen, 2a (30 g), m-pyridine boronic acid (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The reaction was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 25 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 22.6 g of 2b. The yield was 70%. Mass spectrometry analysis determined the molecular mass of 2b to be 358 (calculated value: 357.8).

[0173] Under nitrogen, 2b (30 g), 4b (35 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, the temperature was raised to 100°C, the reaction was stopped by heating under reflux for 12 h, and the temperature was cooled. The mixture was extracted with ethyl acetate and deionized water, the organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 27 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 25.4 g of compound 13. The yield was 86%. Mass spectrometry analysis determined the molecular mass of 579 (calculated value: 579.6).

[0174] Example 14, Synthesis of Compound 14:

[0175] Under nitrogen, 1a (30 g), 5b (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 25 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 23.3 g of compound 14. The yield was 80%. Mass spectrometry analysis determined the molecular mass of 579 (calculated value: 578.63).

[0176] Example 15, Synthesis of Compound 15:

[0177] Under nitrogen, 1a (30 g), 12a (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 22 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 21.1 g of compound 15. The yield was 72%. Mass spectrometry analysis determined the molecular mass of the product to be 580 (calculated value: 579.62).

[0178] Example 16, Synthesis of Compound 16:

[0179] Under nitrogen, 1a (30 g), 13b (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 27 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 24.6 g of compound 16. The yield was 85%. Mass spectrometry analysis determined the molecular mass of 579 (calculated value: 578.63).

[0180] Example 17, Synthesis of Compound 17:

[0181] Under nitrogen, 12a (30 g), 13b (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then cooled. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 24 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 23.2 g of compound 17. The yield was 80%. Mass spectrometry analysis determined the molecular mass of 578 (calculated value: 577.64).

[0182] Example 18, Synthesis of Compound 18:

[0183] Under nitrogen, 3a (30 g), 13b (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The product was extracted with ethyl acetate and deionized water, and the organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 27 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 21 g of compound 18. The yield was 72%. Mass spectrometry analysis determined the molecular mass of 667 (calculated value: 667).

[0184] Example 19, Synthesis of Compound 19:

[0185] Under nitrogen, 3a (30 g), 13b (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then cooled. The product was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 25 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 20 g of compound 19. The yield was 67%, and the molecular mass determined by mass spectrometry was 667 (calculated value: 667).

[0186] Example 20, Synthesis of Compound 20:

[0187] Under nitrogen, 2a (30 g), azacarbazole (40 g), sodium tert-butoxide (10 g), and 300 mL of DMF were added to a three-necked flask. The atmosphere was replaced with nitrogen three times. The mixture was stirred at room temperature for 12 hours, then heated to 100°C for another 12 hours before being stopped and cooled. The reaction was then extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 40 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 20 g of compound 20a in 50% yield.

[0188] Under nitrogen, 20a (30 g), 13b (30 g), potassium carbonate (25 g), tetrakistriphenylphosphine palladium (1 g), and 300 mL of toluene / 50 mL of ethanol / 50 mL of water were added to a three-necked flask. The atmosphere was replaced with nitrogen three times, and the reaction temperature was raised to 100°C. The reaction was stopped by heating under reflux for 12 h, and the temperature was then lowered. The mixture was extracted with ethyl acetate and deionized water. The organic phase was washed twice, dried, filtered, and the filtrate was spin-dried to obtain 27 g of crude product. Column chromatography (petroleum ether / ethyl acetate 15:1) yielded 15 g of compound 20. The yield was 60%, and the molecular mass determined by mass spectrometry was 668 (calculated value: 668).

[0189] Preparation process of the mixture: firstly mix the first organic host material and the second organic host material in a mass ratio of 1:1 as uniformly as possible, and then place the mixture in a temperature less than or equal to 10 -3 In a vacuum environment of Torr, the temperature in the vacuum environment is increased to completely melt the two main materials, and after being mixed evenly, the mixture is cooled to room temperature to solidify, and then ground into powder using a ball mill for standby use.

[0190] The energy levels of organic compound materials can be obtained through quantum calculations, such as using TD-DFT (time-dependent density functional theory) or Gaussian09W (Gaussian Inc.). For specific simulation methods, please refer to WO2011141110. First, the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet) is used to optimize the molecular geometry. 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" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated according to the following calibration formula: E S1 , E T1 Use directly.

[0191] HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206

[0192] LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0193] The HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 1:

[0194] Table 1

[0195] Compounds 1 to 8 can be used as the second organic host material, and compounds 9 to 20 can be used as the first organic host material. The numbers and compositions of the mixtures are shown in Table 2. The mass ratio of the first organic host material to the second organic host material in all mixtures is 1:1.

[0196] Table 2

[0197] Compared with the above-mentioned mixed phosphorescent host material, the host material of the currently commonly used carbazole material system structure is marked as Ref 1:

[0198] Preparation of OLED devices:

[0199] The OLED device has ITO / NPB:HATCN(3wt%)(10nm) / NPB(50nm) / TCTA(40nm) / (A-1)~(A-22):5wt%Ir(ppy)3 / B3PYMPM(40nm) / LiQ(2nm) / Al(100nm), and the preparation steps are as follows;

[0200] a. Cleaning of conductive glass substrate: When used for the first time, it can be cleaned with a variety of solvents, such as chloroform, ketone, isopropyl alcohol, and then treated with ultraviolet ozone plasma.

[0201] b、HIL(10nm), HTL(50nm), Prime(40nm), EML(35nm), ETL(40nm): In high vacuum (1×10 -6 It is made by thermal evaporation in millibar (mbar).

[0202] c. Cathode: LiQ / Al (2nm / 100nm) in high vacuum (1×10 -6 It is made by medium thermal evaporation (millibar).

[0203] d. Packaging: The device is encapsulated with UV curable resin in a nitrogen glove box.

[0204] The current-voltage (JV) characteristics of each OLED device were characterized using a characterization instrument, while also recording key parameters such as efficiency, lifetime, and external quantum efficiency. Testing revealed that OLED4 (corresponding to hybrid host (A-4)) exhibited over three times the luminous efficiency and lifetime of OLEDRef1 (corresponding to hybrid host (Ref1)). OLED10 (corresponding to hybrid host (A-10)) exhibited over three times the luminous efficiency and over eight times the lifetime of OLEDRef1. In particular, OLED10 achieved a maximum external quantum efficiency exceeding 20%. This demonstrates that OLED devices prepared using the mixtures of the present invention exhibit significantly improved luminous efficiency and lifetime, as well as significantly enhanced external quantum efficiency.

[0205] In addition, compounds 9, 11, and 14 were also used as single hosts in the preparation of OLEDs, with efficiency and lifetimes 2.5 times higher than those of Ref 1. However, in this device structure, a co-host can achieve even better performance.

[0206] It should be understood that the application of the present invention is not limited to the above examples. For those skilled in the art, improvements or changes can be made based on the above description. All these improvements and changes should fall within the scope of protection of the claims attached to the present invention.

Claims

1. A mixture comprising a first compound H1 and a second compound H2, characterized in that: min((LUMO(H1)-HOMO(H2),LUMO(H2)-HOMO(H1))≤min(E T1 (H1), E T1 (H2))+0.1eV, where LUMO(H1), HOMO(H1) and E T1 (H1) are the highest occupied orbital, lowest unoccupied orbital, triplet energy level of the first compound H1, LUMO (H2), HOMO (H2) and E T1 (H2) are the energy levels of the highest occupied orbital, the lowest unoccupied orbital, and the triplet state of H2 of the second compound, respectively; The first compound H1 has a structure shown in formula (I): in, Two adjacent * in formula (I) are connected to two * in formula (Ia); X are independently represented by N or CR1, and at least one X is N; Y may be identical or different in each case and may represent CR2 or N, wherein not more than two Ys per ring are N; Z is independently represented by N or CR3; Ar1 is selected from a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded; R1-R3, at each occurrence, are the same or different and are selected from hydrogen, deuterium, substituted or unsubstituted alkyl containing 1 to 10 carbon atoms, substituted or unsubstituted aromatic ring system or heteroaromatic ring system containing 5 to 60 ring atoms, or combinations thereof.

2. The mixture according to claim 1, characterized in that The first compound H1 is selected from the structures shown in the following formula (I-1) to formula (I-10): Wherein, X, Y, Ar1, and Z are as defined in claim 1; Wherein Ar1 in formula (1-5) and (1-10) is selected from the following groups: The definition of Y is the same as that of claim 1.

3. The mixture according to claim 1 or 2, characterized in that Ar1 is selected from one or a combination of the following groups: When V appears multiple times, it is independently selected from CR4 or N; W, when present multiple times, is independently selected from CR5R6, SiR7R8, NR9, C(=O), S or O; R4-R9, at each occurrence, may be identical or different and be selected from H, D, or a linear alkyl, alkoxy or thioalkoxy radical having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy radical having 3 to 20 C atoms, or a substituted or unsubstituted silyl radical, or a substituted keto radical having 1 to 20 C atoms, or an alkoxycarbonyl radical having 2 to 20 C atoms, or an aryloxycarbonyl radical having 7 to 20 C atoms, or a cyano, an amino 4-1,4-dihydro-2-nitro ...

4. The mixture according to any one of claims 1 to 3, characterized in that Ar1 is selected from the following structural formulas and may be substituted by 0, 1, 2 or 3 groups selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl and C3-C10 cycloalkyl: Among them, R 12 , R 13 The definition is the same as R4 in claim 3.

5. The mixture according to any one of claims 1 to 4, characterized in that The second compound H2 has a structure shown in one of formula (II) to formula (V): in, L 1 represents an aromatic group or an aromatic hetero group having 5 to 60 ring atoms; L 2 represents a single bond, an aromatic group or an aromatic hetero group having 5 to 30 ring atoms, L 1 , L 2 The connection position can be on any carbon atom on the benzene ring; Ar 4 ,Ar 5 ,Ar 6 ,Ar 7 ,Ar 8 ,Ar 9 Each independently represents an aromatic group or an aromatic hetero group having 5 to 30 ring atoms; X 1 represents a single bond, N(R), C(R)2, Si(R)2, O, C=N(R), C=C(R)2, P(R), P(=O)R, S, S=O or SO2; X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 Each independently represents a single bond, N(R), C(R)2, Si(R)2, O, C=N(R), C=C(R)2, P(R), P(=O)R, S, S=O or SO2, but X 2 and X 3 Not single bond at the same time, X 4 and X 5 Not single bond at the same time, X 6 and X 7 Not single bond at the same time, X 8 and X 9 Not single bond at the same time; R 1 , R 2 , R independently represent H, D, F, CN, alkenyl, alkynyl, nitrile, amine, nitro, acyl, alkoxy, carbonyl, sulfone, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, aromatic hydrocarbon or aromatic heterocyclic having 5 to 60 ring atoms, wherein R 1 , R 2 The connection position can be any carbon atom on the condensed ring, and R 1 , R 2 There can be any number of substituted carbon atoms; n1 represents an integer from 1 to 4.

6. A composition comprising a mixture as claimed in any one of claims 1 to 5, and at least one organic solvent.

7. An organic electronic device comprising a mixture as claimed in any one of claims 1 to 5.

8. The organic electronic device according to claim 7, characterized in that: The organic electronic device is an organic electroluminescent device and comprises a light-emitting layer, wherein the light-emitting layer comprises at least one mixture according to any one of claims 1 to 5.

9. The organic electronic device according to claim 7, characterized in that: The organic electronic device is an organic electroluminescent device and comprises a light-emitting layer, an electron transport layer or a hole blocking layer, wherein the light-emitting layer, the electron transport layer or the hole blocking layer comprises a mixture as claimed in any one of claims 1 to 5.

10. An organic compound having a structure represented by the general formula (VI): in, X are independently represented by N or CR1, and at least one X is N; Y may be identical or different in each case and may represent CR2 or N, wherein not more than two Ys per ring are N; Ar1 is selected from a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 40 ring atoms, or a combination of these groups, wherein one or more of the groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded; The D ring is represented by the structure shown in the general formula (VI-1) to the general formula (VI-3): in, Z is independently represented by N or CR3; R1-R3, at each occurrence, are the same or different and are selected from hydrogen, deuterium, substituted or unsubstituted alkyl containing 1 to 10 carbon atoms, substituted or unsubstituted aromatic ring system or heteroaromatic ring system containing 5 to 60 ring atoms, or combinations thereof.

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