Organic mixture, organic compound, and use thereof in organic electronic device

Abstract

Disclosed in the present invention is an organic mixture, comprising a first compound H1 and a second compound H2, wherein the first compound H1 is a p-type material using bicarbazole as a core structure, and the second compound H2 is an n-type material using biindolo[3,2,1-jk]carbazole as a core structure. A combination of the two main materials allows for maximized utilization of excitons, achieves a relatively balanced transmission property, reduces the concentration of the excitons and the working voltage of a device, and can effectively improve the efficiency of related electronic devices, especially (blue phosphorescence) OLEDs and prolong the service life thereof, thereby providing an effective solution for improving the overall performance of an organic electronic device. The present invention further relates to a printing ink comprising the organic mixture. The present invention further relates to an organic compound using biindolo[3,2,1-jk]carbazole as a core structure and a use thereof in an organic electronic device.

Description

An organic mixture, an organic compound and their application in organic electronic devices Technical Field

[0001] The present invention relates to an organic mixture, an organic compound, a composition containing the same and an optoelectronic device. The present invention also relates to an electronic device containing the organic mixture or organic compound and applications thereof, in particular, applications in electroluminescent devices. Background Art

[0002] Organic light-emitting diodes (OLEDs) are considered by the industry to be the most promising next-generation display and lighting technology due to their lightweight, active luminescence, high color purity, wide viewing angle, high contrast, high luminous efficiency, low energy consumption, and ease of fabrication for flexible and large-scale panels. To promote the large-scale industrialization of OLEDs, further improving their luminous performance and lifespan is a key challenge that needs to be addressed. The development of high-performance organic optoelectronic materials is crucial to addressing this issue.

[0003] Organic light-emitting diodes (OLEDs) are electroluminescent devices that convert electrical energy into light. To further improve the luminous efficiency of OLEDs, it is necessary to maximize energy conversion efficiency and minimize energy loss. For electroluminescent devices, according to the statistical laws of electron spin in quantum mechanics, singlet and triplet excitons are generated in a ratio of 1:3. This results in a maximum energy utilization rate (internal quantum efficiency) of only 25% for conventional fluorescent materials. However, phosphorescent materials, due to the heavy atom effect, enhance spin-orbit coupling in the triplet state, enabling the previously spin-forbidden transition from the triplet state to the ground state. Both singlet and triplet excitons can radiate light, and the energy utilization rate can theoretically reach 100%. Currently, significant progress has been made in red and green phosphorescent materials, both in terms of host and guest properties, leading to industrialization. However, the performance of phosphorescent blue OLEDs, particularly their lifetime, remains far below commercial standards, forcing the use of fluorescent blue OLEDs in current commercial displays. Due to their low efficiency, fluorescent blue OLEDs are the primary limiting factor in OLED display energy consumption. Blue phosphorescent materials have become the last holy grail of OLED materials.

[0004] Blue phosphorescent OLEDs depend on the host and guest materials. The host material can achieve a balance between energy level matching and charge transfer, preventing exciton aggregation quenching, and is an indispensable component for improving the device lifespan and stability of organic light-emitting diodes. Using exciplexes as phosphorescent host materials is a relatively common method. This method can use two organic compounds of different polarities to form an intermediate state, namely an exciplex, to improve the device lifespan (see, for example, Kim et al., Adv. Mater., Vol 26, 5864, (2014)). To date, many companies have reported technologies using exciplexes as co-hosts. For example, Rohm and Haas Electronic Materials Korea Ltd. disclosed a co-host in which the first host and the second host are a bicarbazole derivative and a carbazole derivative, respectively (US2017 / 0062730). Samsung disclosed a co-host in which the two host materials are selected from an electron transport host and a hole transport host, respectively (KR20160026744). Recently, Sun et al. reported a blue phosphorescent device (DOI: 10.1038 / s41566-022-00958-4) that achieved a significant breakthrough in lifetime. The device utilizes SiCzCz as a p-type host and SiTrzCz2 as an n-type host, effectively forming an exciplex. However, its lifetime still falls short of commercialization requirements.

[0005] Therefore, more stable host materials still need to be developed. Summary of the Invention

[0006] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide an organic mixture, namely a co-host material, comprising a first compound H1 and a second compound H2, wherein the first compound H1 is a p-type material with biindole [3,2,1-jk] carbazole as the core structure, and the second compound H2 is an n-type material with biindole [3,2,1-jk] carbazole as the core structure, and an organic compound with biindole [3,2,1-jk] carbazole as the core structure, aiming to solve the problems of low stability and device life of existing organic electronic devices.

[0007] The technical solutions of the present invention are as follows:

[0008] An organic mixture comprises a first compound H1 and a second compound H2, wherein the lowest unoccupied molecular orbital (LUMO) energy level (H1) of the first compound H1 is higher than the LUMO (H2) of the second compound H2, the first compound H1 is selected from chemical formula (I-1) or (I-2), and the second compound H2 is selected from chemical formula (II-1):

[0009] Ar1-Ar3 are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 40 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 ring atoms, or combinations of these groups, wherein one or more of these groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded;

[0010] R1-R6 are substituents which, at each occurrence, may be identical or different and are selected from D, or linear alkyl, alkoxy or thioalkoxy groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy or silyl groups having 3 to 20 carbon atoms, or keto groups having 1 to 20 carbon atoms, or alkoxycarbonyl groups having 2 to 20 carbon atoms, or aryloxycarbonyl groups having 7 to 20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a crosslinkable group, 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 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;

[0011] n1, n3, n4 are integers selected from 0 to 7;

[0012] n2 is an integer selected from 0 to 8;

[0013] n5 and n6 are selected from integers from 0 to 10.

[0014] Preferably, in the organic mixture, the first compound H1 and the second compound H2 form a type II heterojunction structure, and min(LUMO(H1)-HOMO(H2),LUMO(H2)-HOMO(H1))≤min(E T1 (H1),E T1 (H2))+0.1eV, where HOMO(H1), LUMO(H1) and E T1 (H1) are the highest occupied molecular orbital, lowest unoccupied molecular orbital, and triplet energy level of the first compound H1; HOMO(H2), LUMO(H2) and E T1 (H2) are the highest occupied molecular orbital, the lowest unoccupied molecular orbital, and the triplet energy level of H2 of the second compound, respectively.

[0015] The organic mixture further comprises another organic functional material; the another organic functional material is preferably a self-luminous body, and the luminous body is preferably a self-fluorescent luminous body, a phosphorescent luminous body or a TADF material.

[0016] The present invention also relates to a composition comprising an organic mixture as described above and at least one organic solvent.

[0017] The present invention further relates to an organic compound having a structure shown in chemical formula (II-1), wherein: 1) n5≥1, and at least one R5 contains an electron-withdrawing group; 2) n6≥1, and at least one R6 contains an electron-withdrawing group.

[0018] The present invention further relates to an optoelectronic device comprising an organic mixture or organic compound as described above.

[0019] Preferably, the above-mentioned optoelectronic device is an organic electroluminescent device, and comprises a substrate, an anode, at least one light-emitting layer and a cathode arranged in sequence, wherein the light-emitting layer comprises at least one organic mixture or organic compound as described above, or is prepared using the composition as described above.

[0020] Beneficial Effects: The organic mixture or organic compound according to the present invention, when applied to organic electronic devices, such as electroluminescent devices, can provide high luminous efficiency and device life. This may be due to, but not limited to, the following: the indole[3,2,1-jk]carbazole core structure contained in the second compound H2 is an n-type structure with large delocalized frontier electron orbitals. Furthermore, compared to the CN bond in SiTrzCz2, the C-C bond connecting the indole[3,2,1-jk]carbazole core structure to other groups has a larger dissociation energy; thus, the device life and stability can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] FIG1 is a diagram of a heterojunction structure, showing two possible types of relative positions of the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) when two organic semiconductor materials H1 and H2 are in contact, wherein the semiconductor heterojunction structure of type II is the energy level structure of the organic mixture according to the present invention;

[0022] FIG2 is a schematic cross-sectional view of a test element for measuring sheet resistance;

[0023] FIG3 is a schematic diagram of an interdigitated electrode used in a test element for measuring sheet resistance;

[0024] FIG4 is a diagram showing an example of a current-voltage test;

[0025] FIG5 is an example diagram of calculating the square resistance of a component by fitting;

[0026] FIG6 is an example diagram showing the calculation of the equivalent square resistance of a single-section CGL by fitting. DETAILED DESCRIPTION

[0027] The present invention provides an organic mixture, namely a co-host material, comprising a first compound H1 and a second compound H2. The first compound H1 is a p-type material with a bicarbazole core structure, the second compound H2 is an n-type material with a biindole[3,2,1-jk]carbazole core structure, and an organic compound with a biindole[3,2,1-jk]carbazole core structure. To further clarify the objectives, technical solutions, and effects of the present invention, the present invention is described in further detail below. It should be understood that the specific embodiments described herein are intended solely to illustrate the present invention and are not intended to limit the present invention.

[0028] In the description of the embodiments of the present invention, a numerical range represented by “~” refers to a range that includes the numerical values ​​described before and after “~” as the lower limit and the upper limit.

[0029] In this disclosure, the term "and / or" describes the relationship between associated objects, indicating that three possible relationships exist. For example, "A and / or B" can represent: A exists alone, A and B exist simultaneously, and B exists alone. A and B can be singular or plural. The character " / " generally indicates that the associated objects are in an "or" relationship.

[0030] In the present invention, "at least one" means one or more, and "plurality" means two or more. "At least one of the following" or similar expressions refers to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c" or "at least one of a, b, and c" can all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can each be single or plural.

[0031] It should be understood that in various embodiments of the present invention, the size of the serial number of each process does not mean the order of execution. Some or all steps can be executed in parallel or sequentially. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of the present invention.

[0032] The terms used in the embodiments of the present invention are only for the purpose of describing specific embodiments and are not intended to limit the present invention. The singular forms "a", "an", "the" and "the" used in the embodiments of the present invention and the appended claims are also intended to include plural forms unless the context clearly indicates otherwise.

[0033] The term "OLED" is an abbreviation for "Organic Light Emitting Diode," which stands for organic electroluminescent diode, also known as organic electric laser display or organic light-emitting semiconductor (Organic Electroluminescence Display, OLED). OLED is a current-type organic light-emitting device that emits light through the injection and recombination of carriers, and the luminous intensity is proportional to the injected current. Under the action of the electric field, the holes generated by the anode and the electrons generated by the cathode will move, and are injected into the hole transport layer and the electron transport layer respectively, and migrate to the light-emitting layer. When the two meet in the light-emitting layer, energy excitons are generated, which excite the light-emitting molecules and ultimately produce visible light.

[0034] The term "TADF," short for "Thermally Activated Delayed Fluorescence," refers to thermally activated delayed fluorescence, which occurs when the triplet excited state and singlet excited state are close in energy, allowing the triplet excited state to transition to the singlet excited state through thermally activated reverse intersystem crossing (ISC). Conventional luminescence occurs as fluorescence and phosphorescence, respectively, where the exciton returns to the ground state via radiative emission from the singlet and triplet states. Furthermore, the energy difference between the lower singlet and triplet states is typically large, resulting in an inability to return the exciton to the singlet state once it reaches the triplet state through ISC.

[0035] In the present invention, main material, matrix material, host or matrix material have the same meaning and can be interchanged.

[0036] In the present invention, metal organic complex, metal organic complex and organometallic complex have the same meaning and can be used interchangeably.

[0037] In the present invention, the term "substituted or unsubstituted" means that a hydrogen atom in the compound is replaced by a substituent, and "unsubstituted" means that a hydrogen atom on the group is not replaced by a substituent. The substituent may be selected from the following groups: D, F, CN, alkenyl, alkynyl, amine, nitro, acyl, alkoxy, carbonyl, sulfone, boron-containing group, silicon-containing group, alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8), cycloalkyl group having 3 to 50 ring atoms (preferably 3 to 10, more preferably 3 to 8, and even more preferably 5 or 6), aromatic hydrocarbon group or aromatic heterocyclic group having 3 to 50 ring atoms (preferably 3 to 25, more preferably 3 to 18).

[0038] In the present invention, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below also applies unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0039] For purposes of the present invention, an "aromatic hydrocarbon group" refers to a hydrocarbon group containing at least one aromatic ring, including monocyclic and polycyclic ring systems. An "aromatic heterocyclic group" refers to a hydrocarbon group containing at least one aromatic heterocyclic ring (containing heteroatoms), 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., a fused ring. At least one of these polycyclic rings is aromatic or heteroaromatic. For the purposes of the present 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.

[0040] Specific examples of the aromatic hydrocarbon group include benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, pyrene, benzopyrene, triphenylene, acenaphthene, fluorene, and derivatives thereof.

[0041] Specific examples of aromatic heterocyclic 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-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, and derivatives thereof.

[0042] 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.

[0043] 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.

[0044] The singlet energy level E of organic materials S1 It can be measured by fluorescence luminescence spectrum at room temperature or low temperature; the triplet energy level E T1 It can be measured by low-temperature time-resolved luminescence spectroscopy; or obtained by quantum simulation calculation (such as by Time-dependent DFT), such as by the commercial software Gaussian 09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110 or as described below in the examples.

[0045] 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 、E T1 The value is based on the Time-dependent DFT simulation and does not affect the application of other measurement or calculation methods.

[0046] 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.

[0047] The present invention provides an organic mixture comprising a first compound H1 and a second compound H2, wherein the lowest unoccupied molecular orbital (LUMO) energy level (H1) of the first compound H1 is higher than the LUMO (H2) of the second compound H2, the first compound H1 is selected from chemical formula (I-1) or (I-2), and the second compound H2 is selected from chemical formula (II-1):

[0048] Ar1-Ar3 are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 40 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 ring atoms, or combinations 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.

[0049] R1-R6 are substituents which, at each occurrence, may be identical or different and are selected from D, or linear alkyl, alkoxy or thioalkoxy groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy or silyl groups having 3 to 20 carbon atoms, or keto groups having 1 to 20 carbon atoms, or alkoxycarbonyl groups having 2 to 20 carbon atoms, or aryloxycarbonyl groups having 7 to 20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a crosslinkable group, 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 of the 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.

[0050] n1, n3, and n4 are selected from integers from 0 to 7; n2 is selected from integers from 0 to 8; and n5 and n6 are selected from integers from 0 to 10.

[0051] In a preferred embodiment, the organic mixture, wherein the first compound H1 and the second compound H2 form a type II heterojunction structure, i.e., the highest occupied molecular orbital energy level (HOMO) (H1) of the first compound H1 is higher than the HOMO (H2) of the second compound H2, and the lowest unoccupied molecular orbital energy level (LUMO) (H1) of the first compound H1 is higher than the LUMO (H2) of the second compound H2. In certain embodiments, the energy gap of the first compound H1 is smaller than that of the second compound H2. In certain more preferred embodiments, the energy gap of the first compound H1 is larger than that of the second compound H2.

[0052] In certain embodiments, for the organic mixture, HOMO(H1)≥HOMO(H2)+0.10 eV, and / or LUMO(H1)≥LUMO(H2)+0.10 eV.

[0053] In a more preferred embodiment, for the organic mixture, HOMO(H1)≥HOMO(H2)+0.20 eV, and / or LUMO(H1)≥LUMO(H2)+0.20 eV.

[0054] In a more preferred embodiment, for the organic mixture, HOMO(H1)≥HOMO(H2)+0.25eV, and / or LUMO(H1)≥LUMO(H2)+0.25eV.

[0055] In a most preferred embodiment, for the organic mixture, HOMO(H1)≥HOMO(H2)+0.30 eV, and / or LUMO(H1)≥LUMO(H2)+0.30 eV.

[0056] In certain embodiments, the first compound H1 and the second compound H2, wherein E ex =min(LUMO(H1)-HOMO(H2),LUMO(H2)-HOMO(H1))≤min(E T1 (H1),E T1 (H2))+0.2eV, where HOMO(H1), LUMO(H1) and E T1 (H1) are the highest occupied molecular orbital, lowest unoccupied molecular orbital, and triplet energy level of the first compound H1; HOMO(H2), LUMO(H2) and E T1 (H2) are the highest occupied molecular orbital, the lowest unoccupied molecular orbital, and the triplet energy level of H2 of the second compound, respectively.

[0057] In a more preferred embodiment, E ex ≤min(E T1 (H1),ET1 (H2))+0.1eV, better is E ex ≤min(E T1 (H1),E T1 (H2)), particularly preferably ≤min(E T1 (H1),E T1 (H2))-0.1eV, the best is ≤min(E T1 (H1),E T1 (H2))-0.2eV.

[0058] In certain embodiments, E ex ≥2.6eV, preferably E ex ≥2.7eV, preferably E ex ≥2.75eV, especially E ex ≥2.8eV, the best is E ex ≥2.85eV.

[0059] In a more preferred embodiment, the first compound H1 is selected from any one of chemical formulas (I-1a), (I-1b) or (I-2a):

[0060] In a particularly preferred embodiment, the first compound H1 is selected from chemical formula (I-1a) or (I-2a).

[0061] In certain preferred embodiments, the above-mentioned Ar1, Ar2, and Ar3 are independently represented by substituted or unsubstituted aromatic groups or aromatic hetero groups with 5 to 30 ring atoms; in more preferred embodiments, Ar1, Ar2, and Ar3 are independently represented by substituted or unsubstituted aromatic groups or aromatic hetero groups with 5 to 20 ring atoms; in the most preferred embodiment, Ar1, Ar2, and Ar3 are independently represented by substituted or unsubstituted aromatic groups or aromatic hetero groups with 5 to 15 ring atoms.

[0062] In some preferred embodiments, the above-mentioned Ar1, Ar2, and Ar3 may comprise one or more combinations of the following structural groups:

[0063] in,

[0064] A 1 、A 2 、A 3 、A 4 、A 5 、A 6 、A 7 、A 8 Independently selected from CR 7 or N;

[0065] W 1 、W 2 Independently selected from CR 8 R 9 、SiR 8 R 9 NR 7 , C(=O), S or O;

[0066] R 7 、R 8 、R 9 The radicals may be selected, at each occurrence, identically or differently, from H, D, or straight-chain alkyl, alkoxy or thioalkoxy radicals having 1 to 20 C atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy or silyl radicals having 3 to 20 C atoms, or keto radicals having 1 to 20 C atoms, or alkoxycarbonyl radicals having 2 to 20 C atoms, or aryloxycarbonyl radicals having 7 to 20 C atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a crosslinkable group, 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 radicals, where one or more of the radicals can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or the ring to which the radicals are bonded.

[0067] In a more preferred embodiment, the above-mentioned Ar1, Ar2, and Ar3 comprise one of the following structural groups, wherein the H on the ring can be arbitrarily substituted:

[0068] Furthermore, the above-mentioned Ar1, Ar2, and Ar3 are selected from benzene, biphenyl, naphthalene, anthracene, phenanthrene, pyrene, pyridine, pyrimidine, triazine, fluorene, dibenzothiazolidine, silylation, carbazole, thiophene, furan, thiazole, triphenylamine, triphenylphosphine, tetraphenylsilane, spirofluorene, spirosilicon fluorene and other groups and any combination thereof; more preferably, benzene, biphenyl, pyridine, pyrimidine, triazine, furan, carbazole and other groups and any combination thereof.

[0069] In a preferred embodiment, Ar2 or Ar3 in Formula (I-2) or Formula (I-2a) contains an electron-withdrawing group, in particular a weak electron-withdrawing group, preferably pyridine, pyrimidine and pyrazine.

[0070] In a more preferred embodiment, n1, n3, and n4 are 0, that is, there is no corresponding substitution.

[0071] In certain preferred embodiments, the substituents R1-R6 are independently selected from H, D, CN, substituted or unsubstituted alkyl groups with 1 to 18 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 18 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups or aromatic heterocyclic groups with 5 to 30 ring atoms; in more preferred embodiments, R1-R6 are independently selected from H, D, substituted or unsubstituted alkyl groups with 1 to 12 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups or aromatic heterocyclic groups with 5 to 20 ring atoms; in the most preferred embodiment, R1-R6 are independently selected from H, D, substituted or unsubstituted alkyl groups with 1 to 6 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups or aromatic heterocyclic groups with 5 to 15 ring atoms.

[0072] In certain embodiments, E T1 (H1) ≥ 2.7 eV, preferably ≥ 2.8 eV, more preferably ≥ 2.85 eV, most preferably ≥ 2.9 eV.

[0073] In a preferred embodiment, the exciplex formed between the first compound H1 and the second compound H2 has a singlet energy level E S1 and triplet energy level E T1 The difference is ≤0.3 eV, preferably ≤0.25 eV, more preferably ≤0.2 eV, particularly preferably ≤0.15 eV.

[0074] Preferred examples of the first compound H1 according to the chemical formula (I-1), (I-1a), (I-1b), (I-2) and (I-2a) are shown below, but are not limited to:

[0075] According to the second compound H2 of chemical formula (II-1), its core is composed of two indole[3,2,1-jk]carbazoles connected by a single bond, and the connection method can be arbitrary.

[0076] In some preferred embodiments, the connection positions in the connection method are (2, 5, 10) and (2', 5', 10'):

[0077] In some preferred embodiments, the second compound H2 is selected from any one of chemical formulas (II-1a) to (II-1e):

[0078] In certain more preferred embodiments, the second compound H2 is selected from chemical formulas (II-1a) to (II-1c).

[0079] In a more preferred embodiment, according to the organic mixture of the present invention, wherein, in the chemical formula (II-1) and chemical formulas (II-1a)-(II-1e), n5+n6≥1, and at least one of R5 and R6 contains an electron-withdrawing group.

[0080] Examples of suitable groups having electron-withdrawing properties are shown below, but are not limited thereto, which may be further substituted optionally:

[0081] wherein n is selected from an integer from 1 to 3; X 1 -X 8 is selected from CR or N, and at least one of them is N, Z1, Z2, and Z3 are independently selected from N(R), C(R)2, Si(R)2, O, C=N(R), C=C(R)2, P(R), P(=O)R, S, S=O, SO2 or none, but at least one of them is not none; wherein R can be selected from the following groups: hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl.

[0082] Further electron withdrawing groups may be selected from F, cyano or a structure comprising the following groups, which may be further optionally substituted:

[0083] In some particularly preferred embodiments, the electron-withdrawing group is selected from CN or one or more combinations of the structures shown below:

[0084] In some other preferred embodiments, according to the organic mixture of the present invention, the second compound H2 is selected from the chemical formula (II-1a-1) to (II-1e-1):

[0085] Among them, Ar a1 -Ar a4 ,Ar b1 -Ar b4 ,Ar c1 -Ar c4 ,Ar d1 -Ar d4 ,Ar e1 -Ar e4 Each of the alkyl groups is independently selected from H, D, F, cyano, and a substituted or unsubstituted aromatic group or aromatic hetero group having 5 to 30 ring atoms.

[0086] More preferably, Ar a1 -Ar a4 ,Ar b1 -Ar b4 ,Ar c1 -Ar c4 ,Ard1 -Ar d4 ,Ar e1 -Ar e4 Selected from benzene, biphenyl, pyridine, pyrimidine, triazine, furan, carbazole and any combination thereof

[0087] In certain preferred embodiments, Ar a1 -Ar a4 At least one of them contains the above electron-withdrawing group; Ar b1 -Ar b4 At least one of them contains the above electron-withdrawing group; Ar c1 -Ar c4 At least one of them contains the above electron-withdrawing group; Ar d1 -Ar d4 At least one of them contains the above electron-withdrawing group; Ar e1 -Ar e4 At least one of them contains the above-mentioned electron-withdrawing group.

[0088] In certain embodiments, E T1 (H2) ≥ 2.65 eV, preferably ≥ 2.7 eV, more preferably ≥ 2.75 eV, most preferably ≥ 2.85 eV.

[0089] In certain embodiments, the above-mentioned Ar1-Ar3, R5, R6, Ar a1 -Ar a4 ,Ar b1 -Ar b4 ,Ar c1 -Ar c4 ,Ar d1 -Ar d4 ,Ar e1 -Ar e4 Can be further selected from the following chemical formula (A):

[0090] Wherein L0 is selected from a single bond or any divalent linking group; the dotted line represents the linking bond; Ar7-Ar9 are selected from a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 30 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, or a combination of these groups; preferably a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 20 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 20 ring atoms, or a combination of these groups; more preferably a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 15 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 15 ring atoms, or a combination of these groups.

[0091] In a more preferred embodiment, Ar7-Ar9 are selected from benzene, biphenyl, pyridine, pyrimidine, triazine, furan, carbazole or indolecarbazole; particularly preferably benzene, biphenyl, pyridine, pyrimidine, triazine or furan.

[0092] Preferred examples of the second compound H2 according to formula (II-1), formula (II-1a)-(II-1e) and formula (II-1a-1)-(II-1e-1) are shown below, but are not limited to:

[0093] In a very preferred embodiment, the organic mixture is used for the light-emitting layer of an organic electroluminescent device. In some embodiments, due to stability or process considerations, there may be some special requirements for the first compound H1 and the second compound H2.

[0094] In a preferred embodiment, according to the organic mixture of the present invention, at least one of the first compound H1 and the second compound H2 has ((LUMO+1)-LUMO) ≥ 0.1eV, preferably ≥ 0.15eV, better ≥ 0.20eV, even better ≥ 0.25eV, and most preferably ≥ 0.30eV.

[0095] In a more preferred embodiment, according to the organic mixture of the present invention, the second compound H2 has ((LUMO+1)-LUMO) ≥ 0.1eV, preferably ≥ 0.15eV, better ≥ 0.20eV, even better ≥ 0.25eV, and most preferably ≥ 0.30eV.

[0096] In another preferred embodiment, according to the organic 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, better ≥ 0.30 eV, even better ≥ 0.35 eV, and most preferably ≥ 0.40 eV.

[0097] In another more preferred embodiment, according to the organic mixture of the present invention, the first compound H1 has (HOMO-(HOMO-1)) ≥ 0.2eV, preferably ≥ 0.25eV, better ≥ 0.30eV, even better ≥ 0.35eV, and most preferably ≥ 0.40eV.

[0098] In a preferred embodiment, in the organic mixture, the molar ratio of the first compound H1 to the second compound H2 is from 2:8 to 8:2; the preferred molar ratio is 3:7 to 7:3; and the more preferred molar ratio is 4:6 to 6:4.

[0099] In a preferred embodiment, at least one of the first compound H1 and the second compound H2 in the organic mixture of the present invention has a glass transition temperature (Tg) ≥ 100°C; in a more preferred embodiment, at least one has a Tg ≥ 120°C; in a more preferred embodiment, at least one has a Tg ≥ 140°C; in a further more preferred embodiment, at least one has a Tg ≥ 160°C; in a most preferred embodiment, at least one has a Tg ≥ 180°C.

[0100] In a more preferred embodiment, at least one of the first compound H1 and the second compound H2 in the organic mixture according to the present invention is partially H-deuterated, preferably ≥10% H-deuterated, more preferably ≥20% H-deuterated, most preferably ≥30% H-deuterated, and most preferably ≥40% H-deuterated.

[0101] In a preferred embodiment, in the organic mixture according to the present invention, both the first compound H1 and the second compound H2 are small molecule materials.

[0102] One object of the present invention is to provide a material solution for vapor deposition type OLEDs.

[0103] In a preferred embodiment, the organic mixture according to the present invention is used in an evaporation-type OLED device. For this purpose, the molecular weight of the first compound H1 and the second compound H2 in the organic mixture material according to the present invention is ≤1000 g / mol, preferably ≤900 g / mol, more preferably ≤850 g / mol, even more preferably ≤800 g / mol, and most preferably ≤700 g / mol.

[0104] The following are more important preferred embodiments:

[0105] Embodiment I: The organic mixture, wherein the difference in molecular weight between the first compound H1 and the second compound H2 does not exceed 80 Dalton; preferably, the difference in molecular weight does not exceed 60 Dalton; more preferably, the difference in molecular weight does not exceed 30 Dalton.

[0106] Embodiment II: The organic mixture, wherein the difference in sublimation temperature between the first compound H1 and the second compound H2 is no more than 30K; preferably, the difference in sublimation temperature is no more than 20K; more preferably, the difference in sublimation temperature is no more than 10K.

[0107] Example III: The organic mixture, wherein the difference in evaporation rate between the first compound H1 and the second compound H2 at a certain vacuum degree and a certain evaporation temperature does not exceed 5% (based on the evaporation rate of the first compound H1), more preferably does not exceed 4%, and most preferably does not exceed 3%.

[0108] The present invention also relates to an organic mixture, in particular to a preparation method (premix preparation method) according to Example I and / or Example II and / or Example III: a first compound H1 and a second compound H2 in a certain mass ratio are mixed as uniformly as possible, and then the mixture is placed 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.

[0109] Another object of the present invention is to provide a material solution for printed OLEDs.

[0110] For this purpose, at least one, preferably both, of the first compound H1 and the second compound H2 in the organic mixture according to the invention have a molecular weight of ≥700 g / mol, preferably ≥800 g / mol, more preferably ≥900 g / mol, even more preferably ≥1000 g / mol, and most preferably ≥1100 g / mol.

[0111] In a premixed co-host in vapor-deposited OLEDs, the two host materials are required to have similar chemical or physical properties, such as molecular weight and sublimation temperature. The present invention has discovered that in solution-processed OLEDs, two host materials with different properties may enhance film-forming performance, thereby improving device performance. In addition to molecular weight and sublimation temperature, these properties may also include other properties, such as glass transition temperature and molecular volume. Therefore, for printed OLEDs, preferred embodiments of the organic mixture according to the present invention include:

[0112] The difference in molecular weight between the first compound H1 and the second compound H2 is ≥120 g / mol, preferably ≥140 g / mol, more preferably ≥160 g / mol, most preferably ≥180 g / mol.

[0113] The difference in sublimation temperature between the first compound H1 and the second compound H2 is ≥60K, preferably ≥70K, more preferably ≥75K, most preferably ≥80K.

[0114] The difference in glass transition temperature between the first compound H1 and the second compound H2 is ≥20K, preferably ≥30K, more preferably ≥40K, most preferably ≥45K.

[0115] The difference in molecular volume between the first compound H1 and the second compound H2 is ≥20%, preferably ≥30%, more preferably ≥40%, most preferably ≥45%.

[0116] In other embodiments, at least one, and preferably both, of the first compound H1 and the second compound H2 in the organic mixture of the present invention has a solubility in toluene of ≥2 mg / mL, preferably ≥3 mg / mL, more preferably ≥4 mg / mL, and most preferably ≥5 mg / mL at 25°C.

[0117] 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 ≤3000 g / mol, preferably ≤2000 g / mol, and most preferably ≤1500 g / mol.

[0118] 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.].

[0119] 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(phenylene vinylene). The C atoms on the main chain can also be replaced by other non-C atoms, and when the sp 2 When 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 aryl amines, aryl phosphine, other heteroaromatics, organometallic complexes, etc. in the main chain.

[0120] In a particularly preferred embodiment, the organic mixture further comprises another organic functional material. The another organic functional material comprises a hole (also known as an electron 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 triplet 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.

[0121] In certain preferred embodiments, the organic mixture further comprises a light-emitting body, and the light-emitting body is selected from phosphorescent light-emitting bodies or TADF materials.

[0122] In a preferred embodiment, the organic mixture further comprises a phosphorescent light emitting body, wherein the weight percentage of the phosphorescent light emitting body is ≤20 wt%, preferably ≤15 wt%, and more preferably ≤10 wt%.

[0123] Phosphorescent emitters are also called triplet emitters. In a preferred embodiment, the phosphorescent emitter has the general formula M(L): n0 wherein M is a metal atom, L can be the same or different at each occurrence, is an organic ligand, which is bonded or coordinated to the metal atom M through one or more positions, and n0 is an integer greater than 1, preferably 1, 2, 3, 4, 5 or 6. Alternatively, these metal complexes are linked to a polymer through one or more positions, preferably through the organic ligand.

[0124] In a preferred embodiment, the metal atom M is selected from transition metal elements, lanthanides or actinides, preferably from Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag, particularly preferably from Os, Ir, Ru, Rh, Re, Pd or Pt, most preferably from Ir or Pt.

[0125] Typically, phosphorescent emitters contain chelating ligands, i.e., ligands that coordinate to the metal via at least two binding points. Particularly preferred are triplet emitters containing two or three identical or different bidentate or polydentate ligands. Chelating ligands contribute to increasing the stability of the metal complex.

[0126] Examples of organic ligands may be selected from phenylpyridine derivatives, 7,8-benzoquinoline derivatives, 2(2-thienyl)pyridine derivatives, 2(1-naphthyl)pyridine derivatives, or 2-phenylquinoline derivatives. All of these organic ligands may be substituted, for example, with fluorine-containing or trifluoromethyl groups. The auxiliary ligand may preferably be selected from acetic acid, acetone, or picric acid.

[0127] In a preferred embodiment, the metal complex useful as triplet emitter has the following form:

[0128] The metal atom M1 is selected from transition metal elements, lanthanides or actinides, preferably from Ir, Pt, Pd, Au, Rh, Ru, Os, Re, Cu, Ag, Ni, Co, W or Eu, and particularly preferably from Ir, Au, Pt, W or Os.

[0129] Ar4 and Ar5 may be the same or different at each occurrence and are cyclic groups, wherein Ar4 contains at least one donor atom (i.e., an atom with a lone pair of electrons, such as nitrogen), through which the cyclic group coordinates to the metal; wherein Ar5 contains at least one carbon atom, through which the cyclic group is bonded to the metal; Ar4 and Ar5 are covalently bonded together and may each carry one or more substituents, which may be further bonded together by substituents; L' may be the same or different at each occurrence and is a bidentate chelating ancillary ligand, preferably a monoanionic bidentate chelating ligand; q1 may be 0, 1, 2, or 3, preferably 2 or 3; q2 may be 0, 1, 2, or 3, preferably 1 or 0. Examples of organic ligands may be selected from phenylpyridine derivatives or 7,8-benzoquinoline derivatives. All of these organic ligands may be substituted, for example, with alkyl chains or fluorine- or silicon-containing substitutions. The ancillary ligand may preferably be selected from acetone acetate or picric acid.

[0130] In a particularly preferred embodiment, the phosphorescent emitter is a transition metal complex (preferably a metal complex of Ir or Pt) comprising at least one ligand or part of a ligand selected from the group consisting of:

[0131] Wherein T is selected from B, Al, Ga or In; K 1’ Is a direct bond selected from NR e PR e , O, S or Se; Y 1 -Y 15 are selected from C or N; Y ’ Selected from BR e NR e PR e ,O,S,Se,C=O,C=S,C=Se,C=NR e、C=CR e R f 、S=O、SO2、CR e R f 、P(O)R e 、SiR e R f or GeR e R f； ; R e and R f Can be fused or linked to form a ring; R a 、R b 、R c and R d are represented as a single to the maximum possible number of substituents or unsubstituted, respectively;

[0132] R a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d 、R e and R f are independently selected from H, D, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boron, arylalkyl, alkoxy, aryl, alkenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfonamide, sulfoxide, phosphorus, selenoyl, or a combination of these groups; and R a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d Any two adjacent substituents may be fused or linked to form a ring or to form a multidentate ligand.

[0133] Examples of some phosphorescent materials and their applications can be found in the following patent documents and literature: WO200070655, WO200141512, WO200202714, WO200215645, EP1191613, EP1191612, EP1191614, WO2005033244, WO2005019373, US20050258742, WO200914 6770, WO2010015307, WO2010031485, WO2010054731, WO2010054728, WO2010086089, WO2010099 852, WO2010102709, US20070087219A1, US20090061681A1, US20010053462A1, Baldo, Thompson et al.Nature 403,(2000),750-753, Adachi et al.Appl.Phys.Lett.78(2001),1622-1624, J.Kido et al.Appl.Phys.Lett.65(1994),2124, Kido et al. al.Chem.Lett.657,1990,US20070252517A1,Johnson et al.,JACS105,1983,1795,Wrighton,JACS 96,1974,998,Ma et al.,Synth.Metals The entire contents of the above-listed patent documents and literature are hereby incorporated by reference into this document.

[0134] Some examples of suitable metal complexes as phosphorescent emitters are listed below, but are not limited to:

[0135] In another preferred embodiment, the organic mixture further comprises a fluorescent light emitting body, wherein the weight percentage of the fluorescent light emitting body is ≤15 wt%, preferably ≤10 wt%, and more preferably ≤8 wt%.

[0136] In another preferred embodiment, the organic mixture further comprises a TADF luminescent material, wherein the weight percentage of the TADF luminescent material is ≤15 wt%, preferably ≤10 wt%, and more preferably ≤8 wt%.

[0137] The following is a more detailed description of fluorescent luminescent materials (singlet luminophores) and TADF luminescent materials (but not limited to these).

[0138] 1. Singlet Emitter

[0139] Singlet emitters often have longer conjugated π-electron systems. To date, there have been many examples, such as styrylamine and its derivatives disclosed in JP2913116B and WO2001021729A1, and indenofluorene and its derivatives disclosed in WO2008 / 006449 and WO2007 / 140847.

[0140] In a preferred embodiment, the singlet emitter can be selected from monostyrylamine, distyrylamine, tertiary styrylamine, tetrastyrylamine, styrylphosphine, styryl ether and aromatic amine.

[0141] A monostyrylamine is a compound comprising an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine. A distyrylamine is a compound comprising two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tert-styrylamine is a compound comprising three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tetrastyrylamine is a compound comprising four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A preferred styrene is diphenylethylene, which may be further substituted. The corresponding phosphines and ethers are defined similarly to the amines. An arylamine or aromatic amine is a compound comprising three unsubstituted or substituted aromatic or heterocyclic rings directly attached to nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably a fused ring system and preferably has at least 14 aromatic ring atoms. Preferred examples include aromatic anthracenamines, aromatic anthracenediamines, aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines, and aromatic chrysenediamines. An aromatic anthracenamine is a compound in which one diarylamine group is directly attached to anthracene, preferably at the 9 position. An aromatic anthracenediamine is a compound in which two diarylamine groups are directly attached to anthracene, preferably at the 9 and 10 positions. Aromatic pyreneamines, aromatic pyrenediamines, aromatic chrysamines, and aromatic chrysenediamines are similarly defined, with the diarylamine groups preferably attached to the 1 or 1,6 positions of the pyrene group.

[0142] Examples, also preferred examples, of singlet emitters based on vinylamine and aromatic amines can be found in the following patent documents: WO 2006 / 000388, WO 2006 / 058737, WO 2006 / 000389, WO 2007 / 065549, WO 2007 / 115610, US 7250532 B2, DE 10 2005 058557 A1, CN 1583691 A, JP 08053397 A, US 6251531 B1, US 2006 / 210830 A, EP 1957606 A1 and US 2008 / 0113101 A1. The entire contents of the above-mentioned patent documents are hereby incorporated herein by reference.

[0143] Examples of singlet emitters based on stilbene and its derivatives are disclosed in US Pat. No. 5,121,029.

[0144] Further preferred singlet emitters can be selected from indenofluorene-amines and indenofluorene-diamines, as disclosed in WO 2006 / 122630, benzindenofluorene-amines and benzindenofluorene-diamines, as disclosed in WO 2008 / 006449, and dibenzoindenofluorene-amines and dibenzoindenofluorene-diamines, as disclosed in WO 2007 / 140847.

[0145] Other materials that can be used as singlet emitters are polycyclic aromatic hydrocarbon compounds, especially derivatives of the following compounds: anthracene such as 9,10-di(2-naphthyl)anthracene, naphthalene, tetracene, xanthene, phenanthrene, pyrene (such as 2,5,8,11-tetra-t-butylperylene), indenopyrene, benzo-fused ring such as (4,4'-bis(9-ethyl-3-carbazolylvinyl)-1,1'-biphenyl), diindenopyrene, decacycloene, hexabenzophenone, fluorene, spirobifluorene, arylpyrene (such as US20060222886), arylenevinyl (such as US5121 029, US5130603), cyclopentadiene such as tetraphenylcyclopentadiene, rubrene, coumarin, rhodamine, quinacridone, pyran such as 4-(dicyanomethylene)-6-(4-(p-dimethylaminophenyl)-2-methyl)-4H-pyran (DCM), thiopyran, bis(azinyl)imine boron compounds (US2007 / 0092753A1), bis(azinyl)methylene compounds, carbostyryl compounds, oxazinones, benzoxazoles, benzothiazoles, benzimidazoles, and dione pyrrolopyrroles. Some materials for singlet emitters can be found in the following patent documents: US20070252517A1, US4769292, and US6020078. The entire contents of the above-listed patent documents are hereby incorporated herein by reference.

[0146] Some examples of suitable singlet emitters are listed below:

[0147] 2. Thermally activated delayed fluorescence materials (TADF materials)

[0148] Traditional organic fluorescent materials can only utilize 25% of the singlet excitons formed by electrical excitation for luminescence, resulting in a low internal quantum efficiency (up to 25%). Although phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom center, enhance intersystem crossing, they can effectively utilize singlet and triplet excitons formed by electrical excitation for luminescence, achieving a device internal quantum efficiency of 100%. However, the high cost, poor material stability, and severe device efficiency roll-off of phosphorescent materials limit their application in OLEDs. Thermally activated delayed fluorescence (TADF) materials are the third generation of organic light-emitting materials developed after organic fluorescent and organic phosphorescent materials. These materials generally have a small singlet-triplet energy level difference (ΔEst), allowing triplet excitons to be converted to singlet excitons through anti-TAF crossing. This fully utilizes the singlet and triplet excitons formed by electrical excitation, resulting in a device internal quantum efficiency of 100%. Furthermore, the materials offer controllable structure, stable properties, low cost, and the absence of precious metals, making them promising for application in OLEDs.

[0149] TADF materials need to have a small singlet-triplet energy level difference, preferably ΔEst < 0.3 eV, second preferably ΔEst < 0.25 eV, more preferably ΔEst < 0.20 eV, and most preferably ΔEst < 0.1 eV. In a preferred embodiment, the TADF material has a relatively small ΔEst. In another preferred embodiment, TADF has a good fluorescence quantum efficiency. Some TADF luminescent materials can be found in the following patent documents: CN103483332(A), TW201309696(A), TW201309778(A), TW201343874(A), TW201350558(A), US20120217869(A1), WO2013133359(A1), WO2013154064(A1), Adachi, et al. Adv. Mater.,21,2009,4802,Adachi,et.al.Appl.Phys.Lett.,98,2011,083302,Adachi,et.al.Appl.Phys.Lett.,101,2012,093306,Adachi,et.al.Chem.Commun.,48,2012,11392,Adachi,et.al.Nature Photonics, 6, 2012, 253, Adachi, et.al. Nature, 492, 2012, 234, Adachi, et.al. J. Am. Chem. Soc, 134, 2012, 14706, Adachi, et. al. Angew. Chem. Int.Ed,51,2012,11311,Adachi,et.al.Chem.Commun.,48,2012,9580,Adachi,et.al.Chem.Commun.,49,2013,10385,Adachi,et.al.Adv.Mate r., 25, 2013, 3319, Adachi, et.al. Adv. Mater., 25, 2013, 3707, Adachi, et.al. Chem. Mater., 25, 2013, 3038, Adachi, et.al. Chem. Mater., 25, 2013, 3766, Adachi, et.al. J. Mater. Chem. C., 1, 2013, 4599, Adachi, et.al. J. Phys. Chem. A., 117, 2013, 5607, the entire contents of the above-listed patents or article documents are hereby incorporated herein by reference.

[0150] Some examples of suitable TADF emitters are listed below:

[0151] In certain embodiments, the organic mixture according to the present invention has a solubility in toluene at 25° C. of ≥10 mg / mL, preferably ≥15 mg / mL, and most preferably ≥20 mg / mL.

[0152] The present invention further relates to a composition or ink comprising an organic mixture as described above and at least one organic solvent.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] Viscosity can be adjusted by various methods, such as by selecting the appropriate solvent and the concentration of the functional material in the ink. The ink comprising the organic mixture according to the present invention facilitates adjustment of the printing ink within an appropriate range depending on 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 wt% to 30 wt%, preferably in the range of 0.5 wt% to 20 wt%, more preferably in the range of 0.5 wt% to 15 wt%, even more preferably in the range of 0.5 wt% to 10 wt%, and most preferably in the range of 1 wt% to 5 wt%.

[0157] 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.

[0158] 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, 1-methoxynaphthalene, cyclohexylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, 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-methylacetophenone, 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-trimethoxybenzene, 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: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc.

[0159] 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.

[0160] In some other embodiments, the printing 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.

[0161] In a preferred embodiment, the composition according to the present invention is a solution.

[0162] In another preferred embodiment, the composition according to the present invention is a suspension.

[0163] The composition in the embodiment of the present invention may include 0.01wt% to 20wt% of the organic mixture according to the present invention, preferably 0.1wt% to 15wt%, more preferably 0.2wt% to 10wt%, and most preferably 0.25wt% to 5wt% of the organic mixture.

[0164] 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.

[0165] Among them, 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, blade coating, roller printing, twist roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brushing or pad printing, slot extrusion coating, etc. Gravure printing, nozzle printing and inkjet printing are preferred. The solution or suspension may further include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. For detailed information on relevant printing techniques and their requirements for relevant solutions, such as solvents and concentrations, viscosity, etc., please refer to "Handbook of Print Media: Technologies and Production Methods" edited by Helmut Kipphan, ISBN 3-540-67326-1.

[0166] The present invention further relates to an organic compound having a structure represented by chemical formula (II-1), wherein: 1) n5+n6≥1, and at least one R5 or R6 contains an electron-withdrawing group.

[0167] In another preferred embodiment, the organic compound has a structure shown in chemical formula (II-1), wherein: 1) n5≥1, and at least one R5 contains an electron-withdrawing group; 2) n6≥1, and at least one R6 contains an electron-withdrawing group.

[0168] Suitable and preferred electron withdrawing groups are described above.

[0169] In another preferred embodiment, the organic compound is selected from the chemical formula (II-1a-1)-(II-1e-1), wherein Ar a1 -Ar a4 At least two of them contain an electron-withdrawing group; Ar b1 -Ar b4 At least two of them contain an electron-withdrawing group; Ar c1 -Ar c4 At least two of them contain an electron-withdrawing group; Ar d1 -Ar d4 At least two of them contain an electron-withdrawing group; Ar e1 -Ar e4 At least two of them contain an electron-withdrawing group.

[0170] In a more preferred embodiment, the organic compound according to the present invention is at least partially deuterated, preferably ≥10% of the H is deuterated, more preferably ≥20% of the H is deuterated, most preferably ≥30% of the H is deuterated, and most preferably ≥40% of the H is deuterated.

[0171] Based on the above-mentioned organic mixture and organic compound, the present invention further provides an application of the above-mentioned organic mixture and organic compound, i.e., applying the organic mixture or organic compound 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, or an organic sensor and an organic plasmon emitting diode (OPED), in particular an OLED. In an embodiment of the present invention, the organic mixture or organic compound is preferably used in the light-emitting layer of an OLED device.

[0172] The present invention further provides a photovoltaic device comprising at least one organic mixture or organic compound as described above.

[0173] In some preferred embodiments, the optoelectronic device is 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, an organic sensor or an organic plasmon emitting diode (Organic Plasmon Emitting Diode).

[0174] In some more preferred embodiments, the optoelectronic device is an organic electroluminescent device and comprises a substrate, an anode, at least one light-emitting layer, a cathode, and optionally a hole transport layer or an electron transport layer. In certain embodiments, the hole transport layer comprises an organic mixture or organic compound according to the present invention. In a preferred embodiment, the light-emitting layer comprises an organic mixture or organic compound according to the present invention. More preferably, the light-emitting layer comprises an organic mixture or organic compound according to the present invention and at least one light-emitting material, which may be a fluorescent light emitter, a phosphorescent light emitter, or a TADF material.

[0175] The device structure of the organic electroluminescent device is described below, but is not limited thereto.

[0176] The substrate can be opaque or transparent. A transparent substrate can be used to make a transparent light-emitting device. 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 (2,6-naphthalene) (PEN).

[0177] 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), 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, 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.

[0178] 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 are possible 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 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.

[0179] 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.

[0180] In a preferred embodiment, in the organic electroluminescent device according to the present invention, the light-emitting layer thereof comprises the organic mixture or organic compound of the present invention.

[0181] In another preferred embodiment, the light-emitting layer of the organic electroluminescent device can be formed by one of the following two methods: (1) the first compound H1 and the second compound H2 containing a co-host are deposited as one source; (2) the first compound H1 and the second compound H2 are evaporated as two separate sources.

[0182] In another preferred embodiment, in the organic electroluminescent device according to the present invention, the electron transport layer thereof comprises the organic mixture or organic compound according to the present invention.

[0183] According to the organic electroluminescent device of the present invention, the 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.

[0184] The present invention also relates to applications of the organic electroluminescent 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.

[0185] In OLED displays, crosstalk caused by lateral leakage current can negatively impact pixel display quality, including, but not limited to, reduced effective resolution and color accuracy. The magnitude of lateral leakage current in organic thin films is correlated with the sheet resistance (or square resistance) of the film layer. It is generally believed that organic layers with greater square resistance have less lateral leakage current under the same conditions. The square resistance of organic thin films can be measured using the transmission line method (as described in CN116868703A and US12161008B2). The following is a detailed introduction to this method.

[0186] Transmission Line Method

[0187] The square resistance Rs is measured for a given stack of deposited layers on a test element set (see Figure 2), which consists of test elements called channels (two highly conductive electrodes with a gap "l" between them and a width "w" for each electrode). To improve the noise level, a large "w" can be used and the electrodes can be formed in an interdigitated structure to reduce the area requirement (see Figure 3). By having x pairs of parallel interdigitated electrodes with a cross-section length we, 2x-1 conductive areas can be formed, thereby increasing the equivalent channel width w to w=we*(2x-1). Reliable square resistance calculations require multiple such channels with different channel lengths "l".

[0188] The specific measurement is carried out in the following way:

[0189] First, the voltage is swept from -5V to +5V in steps of less than 1V and the current is measured. A linear fit is performed on the data, and the slope of the fit between the current on the x-axis and the voltage on the y-axis gives the channel resistance, "R." This procedure is repeated for each channel, "n," resulting in an "Rn" for channel "n" with a gap, "ln," and a width, "w." For Rs calculations, the width, "w," must remain constant across all channels.

[0190] The resistance "Rn" is then plotted for the channel with gap "ln," and a linear fit is performed. The slope of this fit, multiplied by the channel width "w," yields the sheet resistance Rs of the deposited layer stack. This eliminates the effects of contact resistance and series resistance in the measurement setup.

[0191] Measurements were performed on glass substrates with ITO electrodes. The samples were wet cleaned using a Decon 90 surfactant solution, followed by three rinses with water and isopropyl alcohol, respectively. The substrates were dried with nitrogen gas and then baked at 120°C for 20 minutes before being treated with nitrogen plasma. After deposition of the organic layers and prior to measurement, the samples were encapsulated using UV-curable adhesive using a glass cover containing a desiccant.

[0192] In a stacked device, the equivalent square resistance of a single CGL is confirmed by analyzing the square resistance of different numbers of adjacent CGL bilayers using the transmission line method, as follows: First, different numbers of CGL bilayers are deposited on a substrate having the aforementioned interdigitated electrode structure (see Figure 2). In an embodiment of the present invention, the number of continuously deposited CGL bilayers is 1, 2, and 3, respectively (i.e., comprising 1-3 pairs of mutually contacting P-CGL and N-CGL layers, respectively). As a result, the number of mutually contacting P-CGL / N-CGL interfaces is 1, 3, and 5, respectively. Here, the conductive characteristics of a single CGL can be represented by the P-CGL and N-CGL in contact with each other at half the thickness of the deposited CGL bilayer (i.e., in the CGL bilayer deposited for the equivalent square resistance test, the deposition thickness of the corresponding CGL film layer is twice that of the actual stacked device). By plotting the reciprocal of the element's square resistance against the number of PN interfaces and calculating the slope through a linear fit, we can determine the reciprocal of the equivalent square resistance of a single-cell CGL, and thus the equivalent square resistance of the single-cell CGL. This process eliminates the effects of the electrode-CGL interface and the CGL-encapsulation atmosphere interface.

[0193] Example

[0194] 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.

[0195] 1. Synthesis of compounds

[0196] Synthesis of compound H2-1

[0197] Synthesis of Compound 1-1: In a dry three-necked flask, place 4-aminobiphenyl (16.3 g, 1.0 eq), 2,6-dichloroiodobenzene (29 g, 1.1 eq), palladium acetate (1.1 g, 0.05 eq), sodium tert-butoxide (13.9 g, 1.5 eq), and Xantphos (5.58 g, 0.1 eq). Dissolve the mixture in 300 mL of toluene. Vacuum and refill with nitrogen three times. Heat the reaction mixture to 110°C and stir for 3 hours. After completion of the reaction, cool to room temperature, wash with water, and separate the layers. The aqueous phase is extracted with dichloromethane. The combined organic phases are concentrated and the crude product is passed through a silica gel column (DCM:PE = 1:10) to yield approximately 25 g of Compound 1-1, with a yield of 83%. MS (ASAP) = 314.2.

[0198] Synthesis of Compound 1-2: In a dry three-necked flask, 4,4'-dibromobiphenyl (10 g, 1.0 eq), Compound 1-1 (25 g, 2.5 eq), sodium tert-butoxide (9.23 g, 3.0 eq), tri-tert-butylphosphine tetrafluoroborate (1.85 g, 0.2 eq), and Pd(PPh3)2Cl2 (2.24 g, 0.1 eq) were placed. 250 mL of toluene was then added for dissolution. The mixture was evacuated and filled with nitrogen three times. The temperature was raised to 110°C and stirred overnight. The mixture was cooled to room temperature, washed with water, and separated. The aqueous phase was extracted with dichloromethane, separated, and the combined organic phases were concentrated. The crude product was purified by silica gel column (PE:DCM = 6:1) to yield approximately 18.4 g of Compound 1-2, with a yield of 74%. MS (ASAP) = 778.8.

[0199] Synthesis of Compound H2-1: In a dry three-necked flask, compound 1-2 (22.95 g, 1.0 eq), palladium acetate (1.33 g, 0.2 eq), tricyclohexylphosphine tetrafluoroborate (4.56 g, 0.4 eq), and cesium carbonate (48 g, 5.0 eq) were placed. 500 mL of DMF was then added for dissolution. The mixture was vacuumed and filled with nitrogen for three cycles. The reaction solution was heated to 150°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, washed with water, and filtered. The solid was then dissolved by heating with NMP. While hot, the solid was passed through silica gel. The filtrate was collected, cooled, and the solid precipitated. The solid was filtered to obtain approximately 10.8 g of Compound H2-1, with a yield of approximately 58%. MS (ASAP) = 632.8.

[0200] Synthesis of compound H2-2

[0201] Synthesis of Compound 2-1: In a dry two-necked flask, 2-bromoindole[3,2,1-jk]carbazole (prepared according to J. Mater. Chem. C, 2021, 9, 8226) (224.4 g, 1.0 eq), phenylboronic acid (94.5 g, 1.1 eq), and tetrakistriphenylphosphine palladium (8.1 g, 0.01 eq) were placed. 1.4-dioxane (1 L) and 2M potassium carbonate aqueous solution (500 mL) were added to dissolve the mixture. After three cycles of vacuum and nitrogen filling, the reaction solution was heated to 85°C and stirred for 4 hours. After the reaction, the reaction solution was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The crude product was further passed through a silica gel column (PE:DCM = 10:1) to obtain approximately 106.8 g of compound 2-1, with a yield of 48%. MS (ASAP) = 317.4.

[0202] Synthesis of Compound H2-2: Compound 2-1 (16 g, 1.0 eq) was dissolved in 250 mL of anhydrous dichloromethane. Ferric chloride (33.82 g, 4.0 eq) was dissolved in 400 mL of anhydrous dichloromethane in a dry two-necked flask. The mixture was evacuated and refilled with nitrogen three times. The dichloromethane solution containing Compound 2-1 was slowly added dropwise to the single-necked flask. The reaction was allowed to react at room temperature for 1 hour. After completion of the reaction, the mixture was filtered, the filter cake rinsed with water, and silica gel was dissolved in DMF. The crude product was slurried with ethanol to yield approximately 8.5 g of Compound H2-2, with a yield of 53%. MS (ASAP) = 632.8.

[0203] Synthesis of compound H2-3

[0204] Synthesis of Compound 3-1: In a dry three-necked flask, 2-bromo-4-chloropyridine (135.6 g, 1.0 eq), phenylboronic acid (94.5 g, 1.1 eq), and tetrakistriphenylphosphine palladium (8.1 g, 0.01 eq) were placed. 1,4-dioxane (1 L) and a 2M aqueous potassium carbonate solution (500 mL) were added to dissolve the mixture. After three cycles of evacuation and nitrogen refilling, the reaction mixture was heated to 85°C and stirred for 16 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The crude product was further purified by silica gel column (PE:DCM = 20:1) to yield approximately 112.2 g of Compound 3-1, with a yield of 84%. MS (ASAP) = 189.6.

[0205] Synthesis of Compound 3-2: In a dry three-necked flask, compound 3-1 (94.8 g, 1.0 eq), pinacol diboronate (139.7 g, 1.1 eq), Pd(dppf)Cl2 (18.3 g, 0.05 eq), Xphos (47.7 g, 0.2 eq), and potassium acetate (245.4 g, 5 eq) were placed. 1,4-dioxane (1 L) was added for dissolution. After three cycles of evacuation and nitrogen refilling, the reaction solution was heated to 85°C and stirred for 16 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The resulting crude product was further purified by silica gel column (PE:DCM = 20:1) to yield approximately 132.2 g of compound 3-2, with a yield of 94%. MS (ASAP) = 281.2.

[0206] Synthesis of Compound 3-3: In a dry three-necked flask, compound 3-2 (112.5 g, 1.0 eq), 4-chloroaniline (56.1 g, 1.1 eq), and tetrakistriphenylphosphine palladium (4.6 g, 0.01 eq) were placed. 1.4-Dioxane (1 L) and a 2M aqueous potassium carbonate solution (500 mL) were added to dissolve the mixture. After three cycles of evacuation and nitrogen refilling, the reaction mixture was heated to 85°C and stirred for 16 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The resulting crude product was further purified by silica gel column (PE:DCM = 10:1) to yield approximately 82.8 g of compound 3-3, with a yield of 84%. MS (ASAP) = 246.3.

[0207] Synthesis of Compound 3-4: In a dry three-necked flask, compound 3-3 (23.8 g, 1 eq), 2,6-dichloroiodobenzene (29 g, 1.1 eq), palladium acetate (1.1 g, 0.05 eq), sodium tert-butoxide (13.9 g, 1.5 eq), and Xantphos (5.58 g, 0.1 eq) were placed and dissolved in 300 mL of toluene. The mixture was evacuated and filled with nitrogen three times. The reaction mixture was heated to 110°C and stirred for 3 h. After completion of the reaction, the mixture was cooled to room temperature, washed with water, and separated. The aqueous phase was extracted with dichloromethane, and the combined organic phases were concentrated. The crude product was purified by silica gel column (DCM:PE = 1:10) to obtain approximately 31.4 g of compound 3-4, with a yield of 83%. MS (ASAP) = 391.3.

[0208] Synthesis of Compound 3-5: In a dry three-necked flask, 4,4'-dibromobiphenyl (10 g, 1 eq), Compound 3-4 (31.4 g, 2.5 eq), sodium tert-butoxide (9.23 g, 3 eq), tri-tert-butylphosphine tetrafluoroborate (1.85 g, 0.2 eq), and Pd(PPh3)2Cl2 (2.24 g, 0.1 eq) were placed. 250 mL of toluene was then added for dissolution. The mixture was evacuated and filled with nitrogen three times. The temperature was raised to 110°C and stirred overnight. The mixture was cooled to room temperature, washed with water, and separated. The aqueous phase was extracted with dichloromethane, separated, and the combined organic phases were concentrated. The crude product was purified by silica gel column (PE:DCM = 6:1) to yield approximately 22.2 g of Compound 3-5, with a yield of 74%. MS (ASAP) = 932.8.

[0209] Synthesis of Compound H2-3: In a dry three-necked flask, compound 3-5 (22.2 g, 1 eq), palladium acetate (1.33 g, 0.2 eq), tricyclohexylphosphine tetrafluoroborate (4.56 g, 0.4 eq), and cesium carbonate (48 g, 5 eq) were placed, and 500 mL of DMF was added for dissolution. The mixture was vacuumed and filled with nitrogen for three cycles. The reaction solution was heated to 150°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, washed with water, and filtered. The solid was then dissolved by heating with NMP. The solid was then passed through silica gel while hot. The filtrate was collected, cooled, and the solid precipitated. The solid was filtered to obtain approximately 9.7 g of Compound H2-3, with a yield of approximately 52%. MS (ASAP) = 786.9.

[0210] Synthesis of compound H2-4

[0211] Synthesis of Compound 4-1: In a dry three-necked flask, 4-bromo-2,6-dichloroaniline (120.5 g, 1.0 eq), pinacol diboron (139.7 g, 1.1 eq), Pd(dppf)Cl2 (18.3 g, 0.05 eq), and potassium acetate (245.4 g, 5 eq) were placed. 1,4-dioxane (1 L) was added for dissolution. After three cycles of evacuation and nitrogen refilling, the reaction solution was heated to 85°C and stirred for 16 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The crude product was further purified by silica gel column (PE) to yield approximately 135.4 g of Compound 4-1, with a yield of 94%. MS (ASAP) = 288.0.

[0212] Synthesis of compound 4-2: 2-Bromoindole[3,2,1-jk]carbazole (prepared according to J. Mater. Chem. C, 2021, 9, 8226) (160.1 g, 1.0 eq), compound 4-1 (158.4 g, 1.1 eq) and tetrakistriphenylphosphine palladium (5.8 g, 0.01 eq) were placed in a dry two-necked flask, and 1.4-dioxane (1 L) and 2M potassium carbonate aqueous solution (500 mL) were added to dissolve. After vacuuming and nitrogen filling for three cycles, the reaction solution was heated to 85 ° C and stirred for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The crude product was further passed through a silica gel column (PE: DCM = 10: 1) to obtain approximately 156.5 g of compound 4-2 with a yield of 78%. MS (ASAP) = 401.3.

[0213] Synthesis of Compound 4-3: Compound 4-2 (140.5 g, 1.0 eq) was placed in a dry two-necked flask and dissolved in 500 mL of anhydrous DMF. N-bromosuccinimide (88.9 g, 1.0 eq) was slowly added to the solution in three portions under a nitrogen atmosphere. The mixture was allowed to react overnight at 35°C in the dark. After the reaction, the reaction solution was added to a large amount of water, resulting in a large amount of precipitate. The resulting solid was filtered and recrystallized from hot toluene to obtain approximately 147.9 g of Compound 4-3, with a yield of 88%. MS (ASAP) = 480.2.

[0214] Synthesis of Compound 4-4: Compound 4-3 (144.1 g, 1.0 eq) and cuprous cyanide (53.7 g, 2 eq) were placed in a dry two-necked flask and dissolved in 500 mL of anhydrous DMF. The mixture was reacted at 150°C for 24 hours. After completion of the reaction, the mixture was filtrated through silica gel while still hot. The resulting filtrate was added to a large amount of water, resulting in the precipitation of a large amount of precipitate. The resulting solid was filtered and recrystallized from hot xylene to yield approximately 115.1 g of compound 4-4, with a yield of 90%. MS (ASAP) = 426.3.

[0215] Synthesis of Compound 4-5: In a dry three-necked flask, compound 4-4 (106.6 g, 1.0 eq), bromobenzene (39.3 g, 1.0 eq), sodium tert-butoxide (48.1 g, 2.0 eq), tri-tert-butylphosphine tetrafluoroborate (14.5 g, 0.2 eq), and Pd2(dba)3 (22.9 g, 0.1 eq) were placed. 400 mL of anhydrous toluene was then added for dissolution. The mixture was evacuated and filled with nitrogen three times. The temperature was raised to 110°C and stirred overnight. The mixture was cooled to room temperature, washed with water, and separated. The aqueous phase was extracted with dichloromethane, separated, and the combined organic phases were concentrated. The crude product was purified by silica gel column (PE:DCM = 3:1) to yield approximately 92.9 g of compound 4-5, with a yield of 74%. MS (ASAP) = 502.4.

[0216] Synthesis of compound 4-6: In a dry three-necked flask, compound 4-5 (75.4 g, 1.0 eq), 4-bromo-5'-phenyl-1,1':3',1"-terphenyl (63.6 g, 1.1 eq), sodium tert-butoxide (28.8 g, 2.0 eq), tri-tert-butylphosphine tetrafluoroborate (8.7 g, 0.2 eq) and Pd2(dba)3 (13.7 g, 0.1 eq) were placed, and then 300 mL of anhydrous toluene was added for dissolution. Vacuum and nitrogen were circulated three times, the temperature was raised to 110°C, and the reaction was stirred overnight. The mixture was cooled to room temperature, washed with water, and separated. The aqueous phase was extracted with dichloromethane, separated, and the organic phases were combined and concentrated. The crude product was passed through a silica gel column (PE:DCM=3:1) to obtain approximately 84.7 g of compound 4-6, with a yield of 70%. MS (ASAP) = 806.8.

[0217] Synthesis of Compound H2-4: In a dry three-necked flask, compound 4-6 (80.7 g, 1 eq), palladium acetate (4.5 g, 0.2 eq), tricyclohexylphosphine tetrafluoroborate (14.7 g, 0.4 eq), and cesium carbonate (162.9 g, 5 eq) were placed, and 400 mL of DMF was added for dissolution. The mixture was vacuumed and filled with nitrogen for three cycles. The reaction solution was heated to 150°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, washed with water, and filtered. The solid was then dissolved by heating with NMP. The solution was then passed through silica gel while hot. The filtrate was collected, cooled, and the solid precipitated. The solid was filtered to obtain approximately 33.0 g of Compound H2-4, with a yield of approximately 45%. MS (ASAP) = 733.9.

[0218] Synthesis of compound H2-5

[0219] Synthesis of Compound 5-1: In a dry, single-flask, 3,6-di(pyridin-4-yl)-9H-carbazole (64 g, 1 eq), 1-bromo-4-chloro-2-fluorobenzene (46.1 g, 1.1 eq), and potassium carbonate (55.2 g, 2 eq) were placed. 150 mL of DMF was added to dissolve the mixture. The reaction mixture was then heated to 80°C and stirred overnight. After the reaction was completed, the mixture was added to 300 mL of distilled water, resulting in the precipitation of a solid. The resulting solid was filtered and passed through a silica gel column (PE:DCM = 10:1) to yield approximately 85.8 g of Compound 5-1, with a yield of approximately 84%. MS (ASAP) = 510.8.

[0220] Synthesis of Compound 5-2: In a dry three-necked flask, compound 5-1 (51.1 g, 1 eq), palladium acetate (4.5 g, 0.2 eq), tricyclohexylphosphine tetrafluoroborate (14.7 g, 0.4 eq), and cesium carbonate (162.9 g, 5 eq) were placed, and 200 mL of DMF was added for dissolution. The mixture was vacuumed and filled with nitrogen for three cycles. The reaction solution was heated to 150°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, washed with water, and filtered. The solid was then dissolved by heating with NMP. The solution was then passed through silica gel while hot. The filtrate was collected, cooled, and the solid precipitated. The solid was filtered to obtain approximately 28.0 g of compound 5-2, with a yield of approximately 65%. MS (ASAP) = 429.9.

[0221] Synthesis of Compound H2-5: In a dry two-necked flask, compound 5-2 (21.5 g, 1.0 eq), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (18.4 g, 1.0 eq), and tetrakistriphenylphosphine palladium (0.6 g, 0.01 eq) were placed. 1.4-Dioxane (200 mL) and a 2M aqueous potassium carbonate solution (50 mL) were added for dissolution. After three cycles of evacuation and nitrogen refilling, the reaction solution was heated to 85°C and stirred for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The crude product was further purified by silica gel column (PE:DCM = 2:1) to obtain approximately 24.8 g of compound H2-5, with a yield of 78%. MS (ASAP) = 634.7.

[0222] Synthesis of compound H2-6

[0223] Synthesis of Compound H2-6: In a dry two-necked flask, compound 5-2 (21.5 g, 1.0 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (18.4 g, 1.0 eq), and tetrakistriphenylphosphine palladium (0.6 g, 0.01 eq) were placed. 1.4-Dioxane (200 mL) and 2M potassium carbonate aqueous solution (50 mL) were added for dissolution. The mixture was evacuated and filled with nitrogen three times, and then heated to 85°C with stirring for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The crude product was further purified by silica gel column (PE:DCM = 2:1) to obtain approximately 23.8 g of compound H2-6, with a yield of 75%. MS (ASAP) = 634.7.

[0224] Synthesis of compound H2-7

[0225] Synthesis of Compound 7-1: In a dry, single-flask, 3,6-di(pyridin-4-yl)-9H-carbazole (64 g, 1 eq), 2-bromo-4-chloro-1-fluorobenzene (46.1 g, 1.1 eq), and potassium carbonate (55.2 g, 2 eq) were placed. 150 mL of DMF was added to dissolve the mixture. The reaction mixture was then heated to 80°C and stirred overnight. After the reaction was completed, the reaction mixture was added to 300 mL of distilled water, resulting in the precipitation of a solid. The resulting solid was filtered and passed through a silica gel column (PE:DCM = 10:1) to yield approximately 85.8 g of Compound 7-1, with a yield of approximately 84%.

[0226] Synthesis of Compound 7-2: In a dry three-necked flask, compound 7-1 (51.1 g, 1 eq), palladium acetate (4.5 g, 0.2 eq), tricyclohexylphosphine tetrafluoroborate (14.7 g, 0.4 eq), and cesium carbonate (162.9 g, 5 eq) were placed, and 200 mL of DMF was added for dissolution. The mixture was vacuumed and filled with nitrogen for three cycles. The reaction solution was heated to 150°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, washed with water, and filtered. The solid was then dissolved by heating with NMP. The solution was then passed through silica gel while hot. The filtrate was collected, cooled, and the solid precipitated. The solid was filtered to obtain approximately 28.0 g of compound 7-2, with a yield of approximately 65%. MS (ASAP) = 429.9.

[0227] Synthesis of Compound H2-7: In a dry two-necked flask, compound 7-2 (21.5 g, 1.0 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (18.4 g, 1.0 eq), and tetrakistriphenylphosphine palladium (0.6 g, 0.01 eq) were placed. 1.4-Dioxane (200 mL) and 2M potassium carbonate aqueous solution (50 mL) were added for dissolution. The mixture was evacuated and filled with nitrogen three times, and then heated to 85°C with stirring for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, separated, and the organic phase was concentrated by rotary evaporation and washed with water. The crude product was further purified by silica gel column (PE:DCM = 2:1) to obtain approximately 24.8 g of compound H2-7, with a yield of 78%. MS (ASAP) = 634.7.

[0228] Synthesis of compound H1-1

[0229] Synthesis of Compound H1-1: In a dry three-necked flask, 3,3-dicarbazole (5 g, 1 eq), 4-bromo-1,1'-biphenyl (7 g, 4 eq), palladium acetate (0.34 g, 0.1 eq), sodium tert-butoxide (5.78 g, 8 eq), and tri-tert-butylphosphine (1.22 g, 0.2 eq) were placed. 100 mL of anhydrous toluene was added to dissolve the mixture. The reaction mixture was heated to 110°C and stirred overnight. After the reaction, the organic phase was separated, concentrated by rotary evaporation, and washed with water. The crude product was further purified by silica gel column (PE:DCM = 5:1) to yield approximately 6.7 g of Compound H1-1, with a yield of approximately 70%. MS (ASAP) = 636.8.

[0230] Synthesis of compound H1-2

[0231] Synthesis of Compound H1-2: In a dry two-necked flask, 3,9'-bicarbazole (10 g, 1 eq), (3-bromophenyl)triphenylsilane (13.75 g, 1.1 eq), sodium tert-butoxide (4.34 g, 1.5 eq), Pd2(dba)3 (1.38 g, 0.05 eq), tri-tert-butylphosphine tetrafluoroborate (0.87 g, 0.1 eq.), and 250 mL of toluene were placed. The atmosphere was evacuated and replaced with nitrogen three times. The reaction was allowed to proceed at 110°C overnight. After completion of the reaction, the filter cake was washed with toluene. The mother liquor was directly decolorized by passing it through a short column of silica gel. The eluent was concentrated and purified by column chromatography using a 1:5 ratio of dichloromethane to n-hexane as the eluent. The product-containing eluent was concentrated to yield approximately 14.2 g of Compound H1-2, with a yield of 70%. MS (ASAP) = 666.9.

[0232] Synthesis of compound H1-3

[0233] Synthesis of Compound H1-3: In a dry two-necked flask, 2,9'-bicarbazole (10 g, 1 eq), (3-bromophenyl)triphenylsilane (13.75 g, 1.1 eq), sodium tert-butoxide (4.34 g, 1.5 eq), Pd2(dba)3 (1.38 g, 0.05 eq), tri-tert-butylphosphine tetrafluoroborate (0.87 g, 0.1 eq), and 250 mL of toluene were placed. The mixture was evacuated and replaced with nitrogen three times. The reaction was allowed to proceed at 110°C overnight. After completion of the reaction, the filter cake was washed with toluene. The mother liquor was directly decolorized by passing it through a short column of silica gel. The eluent was concentrated and purified by column chromatography using a 1:5 ratio of dichloromethane to n-hexane as the eluent. The product-containing eluent was concentrated to yield approximately 14.2 g of Compound H1-3, with a yield of 70%. MS (ASAP) = 666.9.

[0234] 2. Preparation of the Mixture

[0235] If H1-1 to H1-3 are used as the first compound H1 in the mixture, H2-1 to H2-4 are used as the second compound H2 in the mixture.

[0236] Mix the first compound H1 and the second compound H2 as evenly as possible in a mass ratio of 1:1, and then place the mixture in a -3 In a 100-torr vacuum environment, the temperature is raised to completely melt the two host materials. Once mixed, the mixture is cooled to room temperature to solidify, and then ground into a powder using a ball mill for later use. The resulting mixtures 1-8 can be used as blue or green phosphorescent hosts.

[0237] Table 1: Composition of the mixture

[0238] The energy levels of organic compound materials can be calculated through quantum calculations, such as using TD-DFT (time-dependent density functional theory) with Gaussian 09W (Gaussian Inc.). For detailed simulation methods, see WO2011141110. The molecular geometry is first optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). The energy structure of the organic molecule is then calculated using TD-DFT (time-dependent density functional theory) using the "TD-SCF / DFT / Default Spin / B3PW91" basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated using the following calibration formulas, with S1, T1, and ΔEst used directly. HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206 LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385 HOMO(eV)=((HOMO(G)×27.212)-0.9899) / 1.1206 LUMO(eV)=((LUMO(G)×27.212)-2.0041) / 1.385

[0239] HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, and the unit is Hartree. The results are shown in Table 2:

[0240] Table 2

[0241] Several examples of the application of the mixture or organic matter of the present invention in OLED devices are listed below to further illustrate the beneficial effects of the mixture or organic matter of the present invention. The materials used in the examples were purchased commercially or synthesized by ourselves.

[0242] Device Example 1: Preparation of a Single-Cell Blue Fluorescent Device

[0243] The single-cell blue fluorescent device structure is HT-1:PD (97:3, 10nm) / HT-1 (50nm) / HT-2 (5nm) / BH:BD=98:2(20nm) / HB(5nm) / ET:LiQ=50:50(25nm) / Yb(1nm) / Ag(80nm), and is prepared according to the following steps:

[0244] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrates: Wet clean with Decon90 surfactant solution, then rinse three times with water and isopropyl alcohol, blow dry with nitrogen, and bake at 120°C for 20 minutes before treating the substrate with nitrogen plasma.

[0245] b. Evaporation: Move the ITO substrate into the vacuum vapor deposition equipment and place it in a high vacuum (1×10 -6 At 100 mbar (100 mbar), two evaporation sources were used to vaporize the materials at different rates, achieving a HT-1:PD ratio of 97:3, forming a 10nm thick hole injection layer. Compound HT-1 was then evaporated on the HI layer to form a 50nm thick hole transport layer, followed by a 5nm thick light-emitting auxiliary layer (HT-2) on the hole transport layer. Two evaporation sources were then used to vaporize the materials at different rates, achieving a BH:BD-1 weight ratio of 98:2, forming a 20nm light-emitting layer. Compound HBL-1 was then evaporated to form a hole blocking layer (HB, 5nm). Compound H2-2 and LiQ were then co-deposited in separate evaporation units at a 50wt% ratio, forming a 25nm thick electron transport layer. Yb was then deposited as an electron injection layer (EIL), followed by an 80nm thick Ag cathode on the EIL.

[0246] c. Packaging: The device is encapsulated with UV curable resin in a nitrogen glove box.

[0247] The preparation process of Device Example 2 to Device Example 6 is the same as the preparation process of Device Example 1, except that Compound H2-2 is replaced by Compounds H2-3 to H2-7, respectively.

[0248] The preparation process of device comparative example 1 is the same as that of device example 1, except that compound ET-1 is used instead of compound H2-2.

[0249] The device performance of the above embodiment and comparative example was tested, as shown in Table 3. The driving voltage and current efficiency were measured at 10 mA / cm 2 The device life of T95 is tested at a constant current density of 50mA / cm 2 The time it takes for the brightness to decay to 95% is compared with T95 of Comparative Example 1 being 100%.

[0250] Table 3

[0251] Compared to Comparative Example 1, the external quantum efficiency and lifetime of Device Examples 1-6 were significantly improved, while the driving voltage was reduced. This demonstrates that the use of the organic compounds of the present invention as electron transport materials in OLEDs can improve device efficiency and lifetime while reducing the device's driving voltage.

[0252] Device Example 7: Preparation of a stacked blue light device

[0253] The stacked blue light device structure is HT-1:PD(97:3,10nm) / HT-1(50nm) / HT-2(5nm) / BH:BD=98:2(20nm) / HB(5nm) / ET-2:LiQ=50:50(25nm) / N-CGL:Yb=98.5:1.5(10nm) / HT-1:PD=95:5(10nm) / HT-1(50nm) / HT-2(5nm) / BH:BD=98:2(20nm) / HB(5nm) / ET-2:LiQ=50:50(25nm) / Yb(1nm) / Ag(80nm), and is prepared according to the following steps:

[0254] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrates: Wet clean with Decon90 surfactant solution, then rinse three times with water and isopropyl alcohol, blow dry with nitrogen, and bake at 120°C for 20 minutes before treating the substrate with nitrogen plasma.

[0255] b. Evaporation: Move the ITO substrate into the vacuum vapor deposition equipment and place it in a high vacuum (1×10 -6At 100 mbar, using two evaporation sources, the materials were vaporized at different rates to achieve a HT-1:PD ratio of 97:3, forming a 10nm thick hole injection layer. Compound HT-1 was then evaporated on the HI layer to form a 50nm thick hole transport layer, followed by a 5nm thick light-emitting auxiliary layer (HT-2) on top of the hole transport layer. Subsequently, using two evaporation sources, the materials were vaporized at different rates to achieve a BH:BD-1 weight ratio of 98:2, forming a 20nm thick light-emitting layer. Then, the compound HBL-1 was evaporated to form a hole blocking layer (HB, 5nm). After that, ET-2 and LiQ were placed in different evaporation units and co-deposited at a ratio of 50 wt% respectively to obtain a 25nm electron transport layer. Subsequently, two evaporation sources were used to control the vaporization of the N-type charge generation material and Yb at different rates, so that the weight ratio of compound H2-1:Yb was 98.5:1.5, forming an N-type charge generation layer (N-CGL) with a thickness of 10nm; then, two evaporation sources were used to vaporize the materials at different rates so that the ratio of HT-1:PD was 95:5, forming a P-type charge generation layer (P-CGL) with a thickness of 10nm; then, according to the same conditions as above, the hole transport layer, light-emitting auxiliary layer, light-emitting layer, hole blocking layer and electron transport layer were evaporated in sequence; then, 1nm of Yb was deposited as the electron injection layer, and finally, an Ag cathode with a thickness of 80nm was deposited on the electron injection layer.

[0256] c. Packaging: The device is encapsulated with UV-curable resin in a nitrogen glove box.

[0257] The preparation process of Device Examples 8 to 13 was the same as that of Device Example 7, except that Compounds H2-2 to H2-7 were used instead of Compound H2-1.

[0258] The preparation process of device comparative example 2 is the same as that of device example 1, except that compound ET-1 is used instead of compound H2-1.

[0259] The device performance of the above embodiment and comparative example was tested, as shown in Table 4. The driving voltage and current efficiency were measured at 10 mA / cm 2 The device life of T95 is tested at a constant current density of 50mA / cm 2 The time it takes for the brightness to decay to 95% is compared with T95 of Comparative Example 2 being 100%.

[0260] Table 4

[0261] Compared to Comparative Example 2, the driving voltage of Device Examples 7-13 was reduced by approximately 0.1 V, while the efficiency and lifetime were improved. This demonstrates that the use of the organic compounds of the present invention as N-type charge generation layer materials in OLEDs can reduce the device's driving voltage while simultaneously improving the device's efficiency and lifetime.

[0262] Comparative Example A0: Equivalent square resistance of the charge generation layer (CGL) containing ET-1 measured by the transmission line method

[0263] According to the present invention, the transmission line method for measuring the equivalent square resistance of the CGL layer can be performed as follows.

[0264] Substrate and Sample Component Preparation: ITO patterned glass with an interdigitated structure was used as the substrate. Interdigitated electrodes with four different channel lengths, l, of 20 μm, 40 μm, 60 μm, and 80 μm were used in different regions of the same substrate. The interdigitated overlap width was we = 2800 μm. Each pair of electrodes contained 17 pairs of interdigitated structures, forming 33 thin-layer conductive regions (2x - 1 = 33). Therefore, for each region, the equivalent channel width w = we * (2x - 1) = 92400 μm.

[0265] Before depositing the organic layer, the substrate was wet cleaned with Decon90 surfactant solution, then rinsed three times with water and isopropyl alcohol, dried with nitrogen, and baked at 120°C for 20 minutes before being treated with nitrogen plasma. -6 At 100 mbar, a resistive heating evaporation source was used. Two evaporation sources were used, and the materials were vaporized at different rates to ensure a weight ratio of HT-1:PD of 95:5, forming a 20nm P-CGL layer. Next, an N-CGL layer was evaporated. ET-1 and metallic Yb were placed in different evaporation units, ensuring a weight ratio of ET-1:Yb of 98.5:1.5, forming a 20nm N-CGL layer to form a CGL bilayer. Following this method, elements with one to three adjacent CGL bilayers were formed, designated element 1-1 to element 1-3. The composition and film thickness of the organic layers in these elements are shown in Table 5:

[0266] Table 5: Structure of the CGL layer sheet resistance measurement element

[0267] After deposition of the organic layers, the samples were encapsulated with UV-curable glue using an encapsulating glass cover including a desiccant before electrical measurements were performed.

[0268] Component square resistance calculation

[0269] On each electrode pair corresponding to a given channel length, a voltage between -5V and +5V is applied in steps of 0.5V and the current is measured. Figure 4 shows a measurement example of element 1-1. Based on the data in Figure 4, the slope of each measurement corresponding to a given channel length is calculated to obtain the resistance Rn of this channel length. The corresponding channel length is plotted against the resistance (Figure 5), the slope is calculated and multiplied by the channel width of 92400μm to obtain the measured sheet resistance Rs. In this example, the slope 1152700Ω / μm is multiplied by the channel width of 92400μm. The result is a sheet resistance of 106.5GΩ / square.

[0270] Based on the same method, the square resistance of components 1-1 to 1-3 is shown in Table 6:

[0271] Table 6: Sheet resistance of components 1-1 to 1-3

[0272] Calculation of equivalent square resistance of CGL layer

[0273] The reciprocal of the square resistance of elements 1-1 to 1-3 is plotted against the number of PN interfaces (Figure 6). Through linear fitting, the slope, i.e., the reciprocal of the equivalent square resistance of a single-section CGL, is obtained to be 0.0030374 square / GΩ, resulting in an equivalent square resistance of 329.2 GΩ / square for a single-section CGL.

[0274] Examples A1-A7: Equivalent square resistance of CGL layers containing compounds H2-1 to H2-7 was measured by transmission line method

[0275] The same method as that of comparative example A0 was used to prepare the components for testing the equivalent square resistance, and the equivalent square resistance of a single CGL was measured and calculated by the transmission line method. The only difference was that H2-1 to H2-7 were used instead of ET-1 in all N-CGL layers.

[0276] After calculation,

[0277] The equivalent square resistance of a single-section CGL containing H2-1 is 638.8 GΩ / square.

[0278] The equivalent square resistance of a single-section CGL containing H2-2 is 684.9 GΩ / square.

[0279] The equivalent square resistance of a single-section CGL containing H2-3 is 973.8 GΩ / square.

[0280] The equivalent square resistance of a single-section CGL containing H2-4 is 1034.7 GΩ / square.

[0281] The equivalent square resistance of a single-section CGL containing H2-5 is 1084.6 GΩ / square.

[0282] The equivalent square resistance of a single-section CGL containing H2-6 is 1204.3 GΩ / square.

[0283] The equivalent square resistance of a single-section CGL containing H2-7 is 1153.8 GΩ / square.

[0284] It can be seen that compared with the single-section CGL containing ET-1, the single-section CGL containing H2-1 to H2-7 has a higher equivalent square resistance, indicating that the organic compound according to the present invention is applied to the N-type charge generation layer material of OLED and can effectively block the lateral current.

[0285] Device Example 14: Preparation of Blue Phosphorescent Device

[0286] The blue phosphor device has a structure of: ITO / HT-3:PD (97:3, 10nm) / HT-3 (60nm) / HT-4 (5nm) / BH:BD (100:8, 18nm) / HBL (5nm) / ET:LiQ (30nm) / LiQ (2nm) / Al (100nm). The specific preparation steps are as follows:

[0287] a. Cleaning of the conductive glass substrate: Wet clean the substrate using Decon90 surfactant solution, then rinse three times with water and isopropyl alcohol, blow dry with nitrogen, bake at 120°C for 20 minutes, and treat the substrate with nitrogen plasma.

[0288] b. Move the ITO substrate into the vacuum vapor deposition equipment and place it in a high vacuum (1×10 -6 Using two evaporation sources at 100 mbar (100 mbar), the materials were vaporized at different rates, resulting in a 97:3 HT-3:PD ratio, forming a 10nm-thick hole injection layer. Compound HT-3 was then evaporated on the HI layer to form a 60nm-thick hole transport layer, followed by a 5nm-thick light-assisting layer (HT-4) on top of the hole transport layer. An 18nm-thick light-emitting layer was then formed using a 50:50:8 ratio of H1-2:H2-3:BD-2. Compound HBL-1 was then evaporated to form a 5nm-thick hole blocking layer (HB). Compound ET-3 and LiQ were then co-deposited in separate evaporation units at a 50 wt% ratio, forming a 30nm-thick electron transport layer. Yb was then deposited as an electron injection layer (EIL), followed by a 100nm-thick Ag cathode on the EIL.

[0289] c. Packaging: The device is encapsulated with UV-curable resin in a nitrogen glove box.

[0290] The preparation process of device examples 15 to 18 is the same as that of device example 14, except that different BHs are used, with H1-2:H2-4, H1-3:H2-3 and H1-3:H2-4 replacing H1-2:H2-3, respectively.

[0291] The preparation process of device examples 19 to 21 is the same as that of device example 14, except that different BHs are used, and mixtures 5 to 8 are used instead of H1-2:H2-3, respectively.

[0292] The preparation process of device comparative example 3 is the same as that of device example 14, except that different BHs are used, and H1-2:BH-1 are used instead of H1-2:H2-3 respectively.

[0293] The device performance of the above embodiment and comparative example was tested, as shown in Table 7. The driving voltage and current efficiency were measured at 10 mA / cm 2 The device life of T95 is tested at a constant current density of 50mA / cm 2 The time it takes for the brightness to decay to 95% is compared with T95 of Comparative Example 3 being 100%.

[0294] Table 7

[0295] Compared with Comparative Example 3, device examples 14 to 21 have lower driving voltages, while also having improved efficiency and lifespan. This demonstrates that the use of the organic compounds of the present invention as blue phosphorescent host materials in OLEDs can reduce the driving voltage of the devices while also improving their efficiency and lifespan.

[0296] Device Example 22: Preparation of Green Phosphorescent Device

[0297] The green phosphorescent device structure is: ITO / HT-1:PD (97:3, 10nm) / HT-1 (80nm) / HT-5 (10nm) / GH1:GH2:GD (50:50:8, 40nm) / HBL (5nm) / ET:LiQ (30nm) / LiQ (2nm) / Al (100nm). The specific preparation steps are as follows:

[0298] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrates: Use various solvents (such as one or more of chloroform, acetone or isopropyl alcohol) to clean, and then perform UV ozone treatment;

[0299] b. Evaporation: Move the substrate into the vacuum vapor deposition equipment and place it in a high vacuum (1×10 -6mbar), the ratio of HT-1 and PD was controlled to be 97:3 to form a 10nm hole injection layer (HI), and then the compound HT-1 was evaporated on the hole injection layer to form an 80nm hole transport layer (HTL), followed by evaporation of the invention compound HT-5 on the hole transport layer to form a 10nm hole auxiliary layer. As the light-emitting layer, a 40nm light-emitting layer film was formed with a mixture of 1:GD at a ratio of 50:50:8. Then the compound HBL-2 ​​formed a hole blocking layer (HB, 5nm), ET-2 and LiQ were placed in different evaporation units and co-deposited at a ratio of 50% by weight to obtain a 30nm electron transport layer, followed by deposition of 2nm of LiQ as an electron injection layer, and finally a 100nm thick Al cathode was deposited on the electron injection layer;

[0300] c. Packaging: The device is encapsulated with UV curable resin in a nitrogen glove box.

[0301] The preparation process of device examples 23 to 25 is the same as that of device example 22, except that different GH1:GH2 are used, and mixture 2 to mixture 4 are used instead of mixture 1, respectively.

[0302] The preparation process of device comparative example 4 is the same as the preparation process of device example 22, except that different GH1:GH2 are used, and PREMIX1 is used instead of mixture 1, where PREMIX1 is a mixture of H1-1 and GH-1, and the preparation method is the same as the preparation method of mixture 1.

[0303] The device performance of the above embodiment and comparative example was tested, as shown in Table 8. The driving voltage and current efficiency were measured at 10 mA / cm 2 The device life of T95 is tested at a constant current density of 50mA / cm 2 The time it takes for the brightness to decay to 95%.

[0304] Table 8

[0305] Compared to Comparative Example 4, device examples 22-25 exhibit lower driving voltages, while also improving efficiency and lifetime. This demonstrates that the use of the organic compounds of the present invention as green phosphorescent host materials in OLEDs can reduce device driving voltages while improving device efficiency and lifetime.

[0306] It should be noted that the above are only specific embodiments of the present invention, but the scope of protection of the present invention is not limited thereto. Any changes or substitutions that can be easily conceived by a person skilled in the art within the technical scope disclosed in the present invention should be included in the scope of protection of the present invention. The embodiments of the present invention and the features within the embodiments can be combined with each other unless there is a conflict. Therefore, the scope of protection of the present invention shall be based on the scope of protection of the claims.

Claims

1. An organic mixture comprising a first compound H1 and a second compound H2, characterized in that: The lowest unoccupied molecular orbital (LUMO) energy level (H1) of the first compound H1 is higher than the LUMO (H2) of the second compound H2, the first compound H1 is selected from the chemical formula (I-1) or (I-2), and the second compound H2 is selected from the chemical formula (II-1): Ar1-Ar3 are selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 40 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 40 ring atoms, or combinations of these groups, wherein one or more of these groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which they are bonded; R1-R6 are substituents which, at each occurrence, may be identical or different and are selected from D, or linear alkyl, alkoxy or thioalkoxy groups having 1 to 20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy or silyl groups having 3 to 20 carbon atoms, or keto groups having 1 to 20 carbon atoms, or alkoxycarbonyl groups having 2 to 20 carbon atoms, or aryloxycarbonyl groups having 7 to 20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyanate, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, a crosslinkable group, 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 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; n1, n3, n4 are integers selected from 0 to 7; n2 is an integer selected from 0 to 8; n5 and n6 are selected from integers from 0 to 10.

2. The organic mixture according to claim 1, characterized in that: The first compound H1 and the second compound H2 form a type II heterojunction structure, and min(LUMO(H1)-HOMO(H2),LUMO(H2)-HOMO(H1))≤min(E T1 (H1),E T1 (H2))+0.1eV, where HOMO(H1), LUMO(H1) and E T1 (H1) are the highest occupied molecular orbital, lowest unoccupied molecular orbital, and triplet energy level of the first compound H1; HOMO(H2), LUMO(H2) and E T1 (H2) are the highest occupied molecular orbital, lowest unoccupied molecular orbital, and triplet energy level of H2 of the second compound, respectively.

3. The organic mixture according to claim 1 or 2, characterized in that The first compound H1 is selected from any one of chemical formulas (I-1a), (I-1b) or (I-2a):

4. The organic mixture according to any one of claims 1 to 3, characterized in that The second compound H2 is selected from any one of chemical formulas (II-1a) to (II-1e):

5. The organic mixture according to any one of claims 1 to 4, characterized in that In the chemical formula (II-1), n5+n6≥1, and at least one of R5 and R6 contains an electron-withdrawing group.

6. The organic mixture according to any one of claims 1 to 5, characterized in that 1) The difference in molecular weight between the first compound H1 and the second compound H2 does not exceed 80 Dalton, and / or 2) The difference in sublimation temperature between the first compound H1 and the second compound H2 does not exceed 30K, and / or 3) At a certain vacuum degree and a certain evaporation temperature, the difference in evaporation rates between the first compound H1 and the second compound H2 does not exceed 5% (based on the evaporation rate of the first compound H1).

7. The organic mixture according to any one of claims 1 to 6, characterized in that The organic mixture further comprises a light emitter, which is selected from phosphorescent light emitters or TADF materials.

8. The organic mixture according to claim 7, characterized in that The phosphorescent emitter is a transition metal complex comprising at least one ligand or partial ligand selected from the group consisting of: Wherein T is selected from B, Al, Ga or In; K 1’ Is a direct bond selected from NR e PR e , O, S or Se; Y 1 -Y 15 are selected from C or N; Y' is selected from BR e NR e PR e ,O,S,Se,C=O,C=S,C=Se,C=NR e 、C=CR e R f 、S=O、SO2、CR e R f 、P(O)R e 、SiR e R f or GeR e R f； ; R e and R f Can be fused or linked to form a ring; R a 、R b 、R c and R d are represented as a single to the maximum possible number of substituents or unsubstituted, respectively; R a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d 、R e and R f are independently selected from H, D, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boron, arylalkyl, alkoxy, alkenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfonamide, sulfoxide, phosphorus, seleno or a combination of these groups; and R a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d Any two adjacent substituents may be fused or linked to form a ring or to form a multidentate ligand.

9. A composition comprising an organic mixture according to any one of claims 1 to 8, and at least one organic solvent.

10. An organic compound having a structure represented by chemical formula (II-1), characterized in that: 1) n5≥1, and at least one R5 contains an electron-withdrawing group; 2) n6≥1, and at least one R6 contains an electron-withdrawing group.

11. A photovoltaic device comprising the organic mixture according to any one of claims 1 to 8 or the organic compound according to claim 10.

12. The optoelectronic device according to claim 11, wherein: The optoelectronic device is an organic electroluminescent device and comprises a substrate, an anode, a light-emitting layer and a cathode arranged in sequence, wherein the light-emitting layer comprises at least one organic mixture according to any one of claims 1 to 8, or the organic compound according to claim 10, or is prepared using the composition according to claim 9.