Organic compound and application thereof in organic electronic device

Abstract

The invention provides an organic compound and application thereof in an organic electronic device. The organic compound is high in structural stereoscopicity, capable of effectively resisting molecular stacking crystallization, high in thermal stability and capable of improving the luminous efficiency of the device and prolonging the service life of the device.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electronic materials and devices, and particularly to an organic compound, a polymer, a mixture, a composition, an organic electronic device containing the same, and its application in an organic electronic device, especially in an organic light-emitting diode. Background Art

[0002] Due to the diversity in synthesis, relatively low manufacturing cost, and excellent optical and electrical properties of organic semiconductor materials, organic light-emitting diodes (OLEDs) have great potential in the application of optoelectronic devices (such as flat panel displays and lighting).

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic electroluminescent element utilizing the organic electroluminescence phenomenon usually has a positive electrode and a negative electrode, and an organic layer is included between them. To improve the efficiency and lifespan of the organic electroluminescent element, the organic layer has a multi-layer structure, and each layer contains different organic substances. Specifically, it may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic layer, and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons transition back to the ground state. Such an organic electroluminescent element has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness. Usually, the large difference in the highest occupied molecular orbital (HOMO) energy level between the hole transport layer and the light-emitting layer increases the difficulty of hole transfer from the hole transport layer to the light-emitting layer, resulting in the accumulation of holes at the interface between the hole transport layer and the light-emitting layer. To solve these problems, a hole auxiliary layer can be introduced between the hole transport layer and the light-emitting layer to facilitate hole transport.

[0004] Although prior arts such as CN111146349A, CN111279502A, CN113135903A, CN113461547A, CN115490601, etc. disclose some hole transport materials used as hole auxiliary layers, it is still necessary to design and develop new materials to achieve the effects of reducing the device voltage, improving the device efficiency and lifespan. Summary of the Invention

[0005] In view of the above deficiencies of the prior art, the purpose of the present invention is to provide an organic compound, a polymer, a mixture, a composition, an organic electronic device containing the same, and its application in an organic electronic device, aiming to solve the problem of low efficiency and lifespan of existing organic electronic devices.

[0006] The technical solution of the present invention is as follows:

[0007] An organic compound having a structure represented by the general formula (I):

[0008]

[0009] Wherein, R 1 -R 4 are the same or different and are each independently selected from a straight-chain alkyl group, alkoxy group, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl group, alkoxy group, thioalkoxy group, silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, carbamoyl group, halocarbonyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, CF 3 , Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, wherein one or more of these groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the group is bonded, and one or more H in each of the above groups may further be substituted by D.

[0010] Meanwhile, at least one of R 1 -R 4 contains a structure represented by the following general formula (I-1), and R 1 and R 2 may further form a ring, and R 3 and R 4 may further form a ring;

[0011]

[0012] * represents the bonding position.

[0013] L 0 、L 1 and L 2 are the same or different in each case and are each independently selected from a single bond, or a substituted or unsubstituted subaromatic group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted subheteroaromatic group having 2 to 30 ring-forming carbon atoms; wherein, any adjacent groups may form a ring, and one or more H in each of the above groups may further be substituted by D.

[0014] Ar 1 and Ar 2Identical or different, and each independently selected from substituted or unsubstituted aromatic groups or heteroaromatic groups having 5 to 60 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 60 ring atoms, or combinations of these groups, wherein one or more of the groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the group is bonded, and one or more H in each of the above groups may be further substituted by D.

[0015] The present invention also provides a polymer comprising at least one repeating unit, and the repeating unit comprises a structure corresponding to an organic compound as described above.

[0016] The present invention further provides a mixture comprising at least one organic compound or polymer as described above, and at least one other organic functional material, and the at least one other organic functional material may be selected from hole (also called electric hole) injection materials (HIM), hole transport materials (HTM), hole blocking materials (HBM), electron injection materials (EIM), electron transport materials (ETM), electron blocking materials (EBM), organic matrix materials (Host), singlet emitters (fluorescent emitters), triplet emitters (phosphorescent emitters), thermally activated delayed fluorescence materials (TADF materials) or organic dyes.

[0017] The present invention also provides a composition comprising at least one organic compound or polymer or mixture as described above, and at least one organic solvent.

[0018] Another object of the present invention is to provide an organic electronic device comprising at least one of the above organic compounds or polymers or mixtures. The organic electronic device may be selected from organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting electrochemical cells (OLEECs), organic field effect transistors (OFETs), organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors or organic plasmon emitting diodes.

[0019] In a more preferred embodiment, the organic electronic device is an organic electroluminescent device, which comprises a hole transport region, and the hole transport region comprises at least one of the above organic compounds, polymers or mixtures.

[0020] Beneficial effects: The organic compound according to the present invention has a strong three-dimensional structure and can be used as a hole transport material, an electron blocking material or a hole auxiliary layer material, which can improve the efficiency, inhibit the crystallization of molecules at the same time, improve the yield in the manufacture of organic electroluminescent elements, and improve the lifetime of organic electroluminescent elements. Detailed embodiments

[0021] The present invention provides an organic compound, its application in an organic electroluminescent device, and an organic electronic device comprising the organic compound. To make the objectives, technical solutions, and effects of the present invention clearer and more definite, the present invention is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0022] In the description of the embodiments of the present invention, the numerical range represented by "~" means a range that includes the values recorded before and after "~" as the lower limit value and the upper limit value.

[0023] In the description of the embodiments of the present invention, a substituent may be further substituted by a substituent. "Substituted group a" may mean that group a is substituted by a substituent, and the substituent may be substituted by at least one further substituent or may not be substituted.

[0024] In the present invention, the term "and / or" describes the association relationship of associated objects and indicates that three relationships may exist. For example, A and / or B may mean: A exists alone, A and B exist simultaneously, or B exists alone. Wherein A and B may be singular or plural. The character " / " generally indicates that the associated objects before and after are in an "or" relationship.

[0025] In the present invention, "at least one" means one or more, and "a plurality" means two or more. "At least one of the following items (pieces)" or similar expressions mean any combination of these items, including any combination of single items (pieces) or plural items (pieces). For example, "at least one of a, b, or c", or "at least one of a, b, and c" can both mean: a, b, c, a-b (i.e., a and b), a-c, b-c, or a-b-c, where a, b, and c can be single or plural respectively.

[0026] It should be understood that in various embodiments of the present invention, the magnitude of the serial numbers of the above processes does not mean the order of execution. Some or all of the steps may 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 to the implementation process of the embodiments of the present invention.

[0027] 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", "the", and "said" used in the embodiments of the present invention and the appended claims are also intended to include the plural forms unless the context clearly indicates otherwise.

[0028] The term "OLED" is an abbreviation for "Organic Light Emitting Diode", which refers to an organic electroluminescent diode, also known as organic electroluminescent display, organic light-emitting semiconductor (Organic Electroluminescence Display, OLED). OLED belongs to a current-type organic light-emitting device, and it is a phenomenon of luminescence caused by the injection and recombination of carriers, and the luminescence intensity is proportional to the injected current. Under the action of an electric field, the holes generated by the anode and the electrons generated by the cathode will move, and are respectively injected into the hole transport layer and the electron transport layer, and migrate to the light-emitting layer. When the two meet in the light-emitting layer, energy excitons are generated, which excite the luminescent molecules and finally generate visible light.

[0029] The term "TADF" is an abbreviation for "Thermally Activated Delayed Fluorescence", which represents thermally activated delayed fluorescence. Its essence is that when the energy of the triplet excited state is close to that of the singlet excited state, the triplet excited state can undergo thermally activated reverse intersystem crossing to the singlet excited state through heat activation. Traditional luminescence is fluorescence and phosphorescence, in which the exciton singlet state and triplet state return to the ground state in the form of radiative luminescence respectively. Moreover, the energy level difference between the generally lower singlet state and the lower triplet state is relatively large, resulting in the exciton being unable to return to the singlet state once it reaches the triplet state through the intersystem crossing (ISC) process from the singlet state.

[0030] In the present invention, the composition, printing ink, and ink have the same definition and can be interchanged.

[0031] In the present invention, the aromatic group, aromatic, and aromatic ring system have the same definition and can be interchanged.

[0032] In the present invention, the heteroaromatic group, heteroaromatic, and heteroaromatic ring system have the same definition and can be interchanged.

[0033] In the present invention, "substituted" means that a hydrogen atom in a compound is replaced by a substituent.

[0034] In the present invention, "the number of ring atoms" refers to the number of atoms among the atoms that form the ring itself in a structural compound obtained by bonding atoms into a ring (for example, monocyclic compound, fused-ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the following "the number of ring atoms" without special instructions. For example, the number of ring atoms in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thiophenyl group is 5.

[0035] In the present invention, an aromatic ring system or an aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including monocyclic groups and polycyclic ring systems. A heteroaromatic ring system or a heteroaromatic group refers to a hydrocarbon group (containing heteroatoms) containing at least one heteroaromatic ring, including monocyclic groups and polycyclic ring systems. The heteroatoms are preferably selected from Si, N, P, O, S and / or Ge, particularly preferably selected from Si, N, P, O and / or S. These polycyclic rings can have two or more rings, where two carbon atoms are shared by two adjacent rings, i.e., fused rings. Among these polycyclic rings, at least one is aromatic or heteroaromatic. For the purposes of the present invention, an aromatic group or a heteroaromatic group includes not only systems of aromatic or heteroaromatic groups, but also, where multiple aromatic or heteroaromatic groups can also be 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, triarylamine, diaryl ether, etc. are also considered aromatic groups for the purposes of this invention.

[0036] Specific examples of aromatic groups are: benzene, naphthalene, anthracene, phenanthrene, coronene, tetracene, pyrene, benzopyrene, triphenylene, acenaphthene, fluorene, and their derivatives.

[0037] Specific examples of heteroaromatic groups are: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thiophenopyrrole, thiophenothiophene, furanopyrrole, furanofuran, thiophenofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, perimidine, quinazoline, quinazolinone, and their derivatives.

[0038] In the present invention, "alkyl" may represent linear, branched and / or cyclic alkyl. The number of carbon atoms of the alkyl may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Non-limiting examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0039] In the embodiments of the present invention, the energy level structures of the organic materials, the singlet energy level S1, the triplet energy level T1, HOMO, and LUMO play crucial roles. The determination of these energy levels is introduced below.

[0040] The HOMO and LUMO energy levels can be measured by the photoelectric effect, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy) or by cyclic voltammetry (hereinafter referred to as CV). Recently, quantum chemical methods, such as density functional theory (hereinafter referred to as DFT), have also become effective methods for calculating the energy levels of molecular orbitals.

[0041] The singlet energy level S1 of the organic material can be determined by the emission spectrum, and the triplet energy level T1 can be measured by the low-temperature time-resolved emission spectrum. S1 and T1 can also be obtained by quantum simulation calculations (such as by Time-dependent DFT), such as through the commercial software Gaussian 09W (Gaussian Inc.). The specific simulation method can be referred to WO2011141110 or as described in the following examples. EST Defined as (S1-T1).

[0042] It should be noted that the absolute values of HOMO, LUMO, S1, and T1 depend on the measurement method or calculation method used. Even for the same method, different evaluation methods, such as the starting point and peak point on the CV curve, can give different HOMO / LUMO values. Therefore, reasonable and meaningful comparisons should be made using the same measurement method and the same evaluation method. In the description of the embodiments of the present invention, the values of HOMO, LUMO, S1, and T1 are based on simulations using Time-dependent DFT, but this does not affect the application of other measurement or calculation methods.

[0043] In the invention, (HOMO-1) is defined as the second-highest occupied orbital energy level, (HOMO-2) is the third-highest occupied orbital energy level, and so on. (LUMO+1) is defined as the second-lowest unoccupied orbital energy level, (LUMO+2) is the third-lowest occupied orbital energy level, and so on.

[0044] The present invention provides an organic compound having a structure represented by the general formula (I):

[0045]

[0046] Wherein, R 1 -R 4 Are the same or different and are each independently selected from a linear alkyl group, alkoxy group, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl group, alkoxy group, thioalkoxy group, silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, carbamoyl group, halocarbonyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, CF 3 , Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, wherein one or more of the groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded, and one or more H in each of the above groups may further be substituted by D. At the same time, at least one of R 1 -R 4 Contains a structure represented by the following general formula (I-1), and R 1 And R 2 May further form a ring, and R 3 And R 4 May further form a ring.

[0047]

[0048] * indicates the position of bonding; L 0 、L 1 and L 2 are the same or different in each case and are each independently selected from a single bond, or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, wherein any adjacent groups may form a ring, and one or more H in the above groups may be further substituted by D.

[0049] Ar 1 and Ar 2 are the same or different in each case and are each independently selected from a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, wherein one or more groups may form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the groups are bonded, and one or more H in the above groups may be further substituted by D.

[0050] In some preferred embodiments, L 0 is selected from a substituted or unsubstituted arylene group or heteroarylene group having 6 to 20 ring atoms.

[0051] In some preferred embodiments, Ar 1 -Ar 2 are each independently 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. In some preferred embodiments, Ar 1 -Ar 2 are each independently selected from 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.

[0052] In some preferred embodiments, the R of the organic compound 1 -R 4 is fully or partially deuterated each time it appears.

[0053] In certain preferred embodiments, the organic compound has a structure represented by General Formula (II-1) to General Formula (II-3):

[0054]

[0055] wherein, L 0 、L1 , L 2 , Ar 1 , Ar 2 , R 2 , R 3 , R 4 are defined as described above; where two adjacent Ls 0 can further form a ring, and two adjacent Ls 0 and R 2 can further form a ring, and two adjacent Ls 0 and R 4 can further form a ring.

[0056] In some preferred embodiments, the organic compound has a structure represented by General Formula (III-1) to General Formula (III-3):

[0057]

[0058] where L 3 is independently selected from a single bond, or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, where any adjacent groups can form a ring, and one or more Hs in the above groups can be further substituted by D; Ar 3 is independently selected from a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, where one or more groups can form a monocyclic or polycyclic aliphatic or aromatic ring system with each other and / or with the ring to which the group is bonded, and one or more Hs in the above groups can be further substituted by D; L 0 , L 1 , L 2 , Ar 1 , Ar 2 are defined as described above; adjacent L 0 and L 1 can further form a ring, adjacent L 0 and L 2 can further form a ring, adjacent L 1 and L 2 can further form a ring, adjacent L 0 and L 3 can further form a ring, adjacent L 0 and L 0 can further form a ring, adjacent L 3 and L 3 can further form a ring.

[0059] In some preferred embodiments, L 0 , L1 , L 2 and L 3 is preferably selected from a single bond or the following structures and combinations:

[0060]

[0061] * indicates the bonding position; the above structures may be further substituted by 0, 1, 2 or 3 substituents R 0 , and the substituent R 0 is selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl or C3-C10 cycloalkyl.

[0062] In certain preferred embodiments, the organic compound has the structures of the following general formulas (IV-1) to (IV-36):

[0063]

[0064]

[0065] wherein one or more H in the above structures may be further substituted by D; m is an integer and may be independently selected from 1, 2, 3 or 4; preferably, m is selected from 1, 2 or 3; more preferably, m is selected from 1 or 2; L 1 , L 2 , Ar 1 , Ar 2 are as defined above; each X and Y are the same or different and are each independently selected from a single bond, O, S, C=O, SiR 5 R 6 , CR 7 R 8 , NR 9 or P(R 10 R 11 )=O, where R 5 -R 11 is as defined for R 1 above.

[0066] In certain preferred embodiments, Ar 1- Ar 3 are each independently selected from the following groups or combinations thereof:

[0067]

[0068] wherein: Z is selected from N or CR 12 ; Q is selected from O, S, S=O, SO 2 , NR 13 , CR 14 R 15 or SiR16 R 17 ; R 12 -R 17 Each occurrence is independently selected from: H, D, or a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy, or silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF 3 , Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

[0069] Further, Ar 1 -Ar 3 is independently selected from the following structures and combinations thereof:

[0070]

[0071] The above structures may be further substituted by 0, 1, 2, or 3 substituents R 0 , and the substituent R 0 is selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl, or C3-C10 cycloalkyl; A 1 is defined as the above R 1 .

[0072] More preferably, Ar 1 -Ar 3 is independently selected from the following structures and combinations thereof:

[0073]

[0074] Wherein: A 1 is defined as above.

[0075] In certain embodiments, an organic compound according to the present invention is preferably, but not limited to, the following structures:

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087] In some embodiments, for the organic compound according to the present invention, its glass transition temperature (Tg) ≥ 100 °C; in some preferred embodiments, its Tg ≥ 120 °C; in some more preferred embodiments, its Tg ≥ 140 °C; in some even more preferred embodiments, its Tg ≥ 160 °C; in one most preferred embodiment, its Tg ≥ 180 °C.

[0088] In some more preferred embodiments, for the organic compound according to the present invention, part of the H is deuterated, preferably 10% or more of the H is deuterated, more preferably 20% or more of the H is deuterated, still more preferably 30% or more of the H is deuterated, most preferably 40% or more of the H is deuterated.

[0089] In some more preferred embodiments, for the organic compound according to the present invention, ((LUMO + 1) - LUMO) ≥ 0.1 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, still more preferably ≥ 0.35 eV, even more preferably ≥ 0.4 eV, most preferably ≥ 0.45 eV.

[0090] In certain preferred embodiments, for the organic compound according to the present invention, (HOMO - (HOMO - 1)) ≥ 0.15 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, still more preferably ≥ 0.35 eV, even more preferably ≥ 0.4 eV, most preferably ≥ 0.45 eV.

[0091] In some preferred embodiments, the organic compound according to the present invention is a small molecule material.

[0092] In some preferred embodiments, the organic compound according to the present invention is used in vapor deposition type OLED devices. For this purpose, for the organic compound according to the present invention, its molecular weight ≤ 1200 g / mol, preferably ≤ 1000 g / mol, more preferably ≤ 900 g / mol, most preferably ≤ 800 g / mol.

[0093] The present invention also relates to a method for synthesizing an organic compound according to general formula (I), in which raw materials containing active groups are used for the reaction. These active raw materials contain at least one leaving group, for example, bromine, iodine, boric acid or borate ester. Appropriate reactions for forming C-C bonds are well-known to those skilled in the art and are described in the literature. Particularly appropriate and preferred coupling reactions are the SUZUKI, STILLE and HECK coupling reactions.

[0094] The present invention also relates to a polymer comprising at least one repeating unit, and the repeating unit comprises a structure corresponding to the organic compound as described above. In certain embodiments, the polymer is a non-conjugated polymer, and the structural unit as shown in general formula (I) is on the side chain. In another preferred embodiment, the polymer is a conjugated polymer. The term "small molecule" as defined herein refers to a molecule that is not a polymer, oligomer, dendrimer, or blend. In particular, there is no repeating structure in the small molecule. The molecular weight of the small molecule is ≤3000 g / mol, preferably ≤2000 g / mol, and most preferably ≤1500 g / mol.

[0095] The polymer, i.e., Polymer, includes homopolymer, copolymer, block copolymer. Additionally, in the present invention, the polymer also includes dendrimer. For the synthesis and application of dendrimer, please refer to [Dendrimers and Dendrons, Wiley-VCH Verlag GmbH&Co.KGaA, 2002, Ed. George R. Newkome, Charles N. Moorefield, Fritz Vogtle.].

[0096] A conjugated polymer is a polymer whose backbone is mainly composed of sp 2 hybrid orbitals of C atoms. Well-known examples include polyacetylene and poly(phenylene vinylene), and the C atoms on the backbone can also be replaced by other non-C atoms. Moreover, when the sp 2 hybridization on the backbone is interrupted by some natural defects, it is still considered a conjugated polymer. Additionally, in the present invention, the backbone of the conjugated polymer contains aryl amine, aryl phosphine, other heteroaromatics, organometallic complexes, etc.

[0097] In some preferred embodiments, the synthesis method of the polymer is selected from SUZUKI-, YAMAMOTO-, STILLE-, NIGESHI-, KUMADA-, HECK-, SONOGASHIRA-, HIYAMA-, FUKUYAMA-, ULLMANT, and HARTWIG-BUCHWALD-.

[0098] In some preferred embodiments, for the polymer according to the present invention, its glass transition temperature (Tg) ≥ 100 °C, preferably ≥ 120 °C, more preferably ≥ 140 °C, even more preferably ≥ 160 °C, and most preferably ≥ 180 °C.

[0099] In some preferred embodiments, for the polymer according to the present invention, the value range of its molecular weight distribution (PDI) is preferably from 1 to 5, more preferably from 1 to 4, still more preferably from 1 to 3, even more preferably from 1 to 2, and most preferably from 1 to 1.5.

[0100] In some preferred embodiments, for the polymer according to the present invention, the value range of its weight-average molecular weight (Mw) is preferably from 10,000 to 1,000,000, more preferably from 50,000 to 500,000, still more preferably from 100,000 to 400,000, even more preferably from 150,000 to 300,000, and most preferably from 200,000 to 250,000.

[0101] The present invention also relates to a mixture, comprising at least one organic compound or polymer as described above, and at least one other organic functional material, where the at least one other organic functional material is selected from hole injection material (HIM), hole transport material (HTM), electron transport material (ETM), electron injection material (EIM), electron blocking material (EBM), hole blocking material (HBM), emitter, host material, organic matrix material, singlet emitter (fluorescent emitter), triplet emitter (phosphorescent emitter), thermally activated delayed fluorescence material or organic dye (TADF), or organic dye. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these 3 patent documents are hereby incorporated herein by reference. The organic functional material can be a small molecule and polymer material.

[0102] In a preferred embodiment, the mixture contains an organic compound according to the present invention and a phosphorescent emitter. Here, the organic compound according to the present invention can act as the host, and the weight percentage of the phosphorescent emitter ≤ 30 wt%, preferably ≤ 25 wt%, more preferably ≤ 20 wt%.

[0103] In another preferred embodiment, the mixture comprises an organic compound according to the present invention, another host material, and a phosphorescent emitter. Here, the organic compound according to the present invention serves as a co-host material, and its weight percentage is ≥10 wt%, preferably ≥20 wt%, more preferably ≥30 wt%, most preferably ≥40 wt%.

[0104] In a more preferred embodiment, the mixture comprises an organic compound according to the present invention, a phosphorescent emitter, and a host material. In this embodiment, the organic compound according to the present invention can serve as an auxiliary luminescent material, and its weight ratio to the phosphorescent emitter ranges from 1:2 to 2:1. In another preferred embodiment, the T1 of the organic compound according to the present invention is higher than that of the phosphorescent emitter.

[0105] In certain embodiments, the mixture comprises an organic compound according to the present invention and another TADF material.

[0106] In certain more preferred embodiments, the mixture according to the present invention includes an organic functional material H1 selected from the organic compounds as described above, and at least another organic functional material H2 selected from hole (also called electric hole) injection or transport materials (HIM / HTM), organic host materials (Host).

[0107] In certain preferred embodiments, in the mixture according to the present invention, at least one of the organic functional material H1 and the organic functional material H2 has ((LUMO + 1) - LUMO) ≥ 0.2 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, even more preferably ≥ 0.35 eV, very preferably ≥ 0.4 eV, most preferably ≥ 0.45 eV.

[0108] In some more preferred embodiments, in the mixture according to the present invention, the organic functional material H1 has ((LUMO + 1) - LUMO) ≥ 0.2 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, even more preferably ≥ 0.35 eV, very preferably ≥ 0.4 eV, most preferably ≥ 0.45 eV.

[0109] In certain preferred embodiments, in the mixture according to the present invention, at least one of the organic functional material H1 and the organic functional material H2 has (HOMO - (HOMO - 1)) ≥ 0.2 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, even more preferably ≥ 0.35 eV, very preferably ≥ 0.4 eV, most preferably ≥ 0.45 eV.

[0110] In some more preferred embodiments, for the mixture according to the present invention, (HOMO-(HOMO-1)) of the organic functional material H2 ≥ 0.2 eV, preferably ≥ 0.25 eV, more preferably ≥ 0.3 eV, even more preferably ≥ 0.35 eV, very preferably ≥ 0.4 eV, and most preferably ≥ 0.45 eV.

[0111] In certain even more preferred embodiments, for the said mixture, 1) ΔE(S1-T1) of the organic functional material H1 ≤ 0.30 eV, preferably ≤ 0.25 eV, more preferably ≤ 0.20 eV, and most preferably ≤ 0.10 eV; and / or 2) the LUMO of the organic functional material H2 is higher than the LUMO of the organic functional material H1, and the HOMO of the organic functional material H2 is lower than the HOMO of the organic functional material H1.

[0112] In certain preferred embodiments, for the said mixture, the organic functional materials H1 and H2 have a type-II semiconductor heterojunction structure, and min((LUMO(H1)-HOMO(H2),LUMO(H2)-HOMO(H1)) ≤ min(ET(H1),ET(H2)) + 0.1 eV, where LUMO(H1), HOMO(H1), and ET(H1) are respectively the lowest unoccupied molecular orbital, the highest occupied molecular orbital, and the energy level of the triplet state of the organic functional material H1, and LUMO(H2), HOMO(H2), and ET(H2) are respectively the lowest unoccupied molecular orbital, the highest occupied molecular orbital, and the energy level of the triplet state of the organic functional material H2. More preferably, min((LUMO(H1)-HOMO(H2),LUMO(H2)-HOMO(H1)) ≤ min(ET(H1),ET(H2)); even more preferably, min((LUMO(H1)-HOMO(H2),LUMO(H2)-HOMO(H1)) ≤ min(ET(H1),ET(H2)) - 0.1 eV.

[0113] In some preferred embodiments, the organic functional materials H1 and H2 have a type-I semiconductor heterojunction structure, and the singlet state energy level and triplet state energy level difference (S1-T1) of the organic functional material H1 or the organic functional material H2 ≤ 0.25 eV, preferably ≤ 0.20 eV, more preferably ≤ 0.15 eV, and most preferably ≤ 0.10 eV.

[0114] In some preferred embodiments, for the said mixture, the molar ratio of the organic functional material H1 to the organic functional material H2 is from 1:9 to 9:1; preferably from 2:8 to 8:2; the preferred molar ratio is from 3:7 to 7:3; the more preferred molar ratio is from 4:6 to 6:4; and the most preferred molar ratio is from 4.5:5.5 to 5.5:4.5.

[0115] In some preferred embodiments, for the mixture described above, the difference in molecular weight between the organic functional material H1 and the organic functional material H2 does not exceed 100 g / mol, preferably does not exceed 80 g / mol, more preferably does not exceed 70 g / mol, still more preferably does not exceed 60 g / mol, very preferably does not exceed 40 g / mol, and most preferably does not exceed 30 g / mol.

[0116] In another preferred embodiment, for the mixture described above, the difference in sublimation temperature between the organic functional material H1 and the organic functional material H2 does not exceed 50 K; more preferably, the difference in sublimation temperature does not exceed 30 K; still more preferably, the difference in sublimation temperature does not exceed 20 K; and most preferably, the difference in sublimation temperature does not exceed 10 K.

[0117] In some embodiments, for the organic functional material H1 and the organic functional material H2 in the mixture according to the present invention, at least one of them has a glass transition temperature (Tg) ≥ 100 °C; in some preferred embodiments, at least one of them has a Tg ≥ 120 °C; in some more preferred embodiments, at least one of them has a Tg ≥ 140 °C; in some still more preferred embodiments, at least one of them has a Tg ≥ 160 °C; and in some most preferred embodiments, at least one of them has a Tg ≥ 180 °C.

[0118] The organic compound according to the present invention can be used as a functional material in the functional layer of an electronic device. The organic functional layer includes, but is not limited to, a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron injection layer (EIL), an electron blocking layer (EBL), a hole blocking layer (HBL), and a light emitting layer (EML).

[0119] In some embodiments, the organic compound according to the present invention is used in the light emitting layer.

[0120] In some embodiments, the organic compound according to the present invention is used in the hole transport layer.

[0121] Some detailed descriptions (but not limited thereto) of the triplet host material (phosphorescent host material), triplet emitter (phosphorescent emitter), TADF material, and HTM material are given below.

[0122] 1. Triplet Host:

[0123] Examples of triplet host materials are not particularly limited, and any metal complex or organic compound can be used as the host as long as its triplet energy level is higher than that of the emitter, especially the triplet emitter or phosphorescent emitter. Examples of metal complexes that can be used as triplet hosts include (but are not limited to) the following general structures:

[0124]

[0125] M1 is a metal; (Y 1 -Y 2 ) is a bidentate ligand, Y 1 and Y 2 are independently selected from C, N, O, P or S; L is a auxiliary ligand; r1 is an integer whose value ranges from 1 to the maximum coordination number of this metal. In some preferred embodiments, the metal complex that can be used as a triplet host has the following form:

[0126]

[0127] (O-N) is a bidentate ligand, in which the metal coordinates with O and N atoms, and r1 is an integer whose value ranges from 1 to the maximum coordination number of this metal;

[0128] In some embodiments, M1 can be selected from Ir and Pt.

[0129] Examples of organic compounds that can be used as triplet hosts are selected from compounds containing cyclic aromatic hydrocarbon groups, such as benzene, biphenyl, triphenylbenzene, benzofluorene; compounds containing aromatic heterocyclic groups, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, dibenzocarbazole, indolocarbazole, pyridoindole, pyrrolodipyridine, pyrazole, imidazole, triazoles, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazines, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, oxazole, dibenzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, phthalazine, quinazoline, quinoxaline, naphthalene, phthalocyanine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranpyridine, furanopyridine, benzothiophenpyridine, thiophenpyridine, benzoselenophenpyridine and selenophenbenzodipyridine; groups containing 2 to 10 ring structures, which can be the same or different types of cyclic aromatic hydrocarbon groups or aromatic heterocyclic groups and are linked to each other directly or through at least one of the following groups, such as oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and alicyclic group. Among them, each Ar can be further substituted, and the substituents can be selected as hydrogen, deuterium, cyano, halogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl.

[0130] In some preferred embodiments, the triplet host material can be selected from compounds containing at least one of the following groups:

[0131]

[0132] Wherein: Ar 4 -Ar6 The definition of Ar is the same as above. 1 ; X 1 -X 8 Same or different, selected from CR 8 R 9 or NR 10 ; Y 0 Selected from CR 8 R 9 or NR 10 or O or S; R 1 -R 10 The definition of R is the same as above. 1 ; n 0 is an integer.

[0133] Examples of suitable triplet host materials are listed below but not limited to:

[0134]

[0135] 2. Triplet Emitter

[0136] The triplet emitter is also called a phosphorescent emitter. In some preferred embodiments, the triplet emitter is a metal complex having the general formula M(L)n, where M is a metal atom, L may be the same or different each time it appears, is an organic ligand, which is bonded or coordinatively linked to the metal atom M through one or more positions, and n is an integer greater than or equal to 1, preferably selected from 1, 2, 3, 4, 5 or 6. Optionally, these metal complexes are linked to a polymer through one or more positions, preferably through an organic ligand.

[0137] In some preferred embodiments, the metal atom M is selected from transition metal elements or lanthanide elements or actinide elements, preferably selected from Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag, and particularly preferably selected from Os, Ir, Ru, Rh, Re, Pd, Au or Pt.

[0138] Preferably, the triplet emitter contains a chelating ligand, i.e., a ligand that coordinates to the metal through at least two binding points. Particularly preferred is that the triplet emitter contains two or three identical or different bidentate or polydentate ligands. The chelating ligand is beneficial to improving the stability of the metal complex.

[0139] Examples of the organic ligand 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, by fluorine-containing or trifluoromethyl groups. The auxiliary ligand may preferably be selected from acetylacetone or picric acid.

[0140] In some preferred embodiments, the metal complex that can be used as a triplet emitter has the following form:

[0141]

[0142] wherein M2 is a metal selected from transition metal elements or lanthanide or actinide elements, and particularly preferably Ir, Pt, Au.

[0143] Ar1, each occurrence of which may be the same or different, is a cyclic group that contains at least one donor atom, i.e., an atom with a lone pair of electrons, such as nitrogen or phosphorus, through which the cyclic group is coordinately bonded to the metal; Ar2, each occurrence of which may be the same or different, is a cyclic group that contains at least one C atom, through which the cyclic group is bonded to the metal; Ar1 and Ar2 are covalently linked together and may each carry one or more substituents, and they may also be linked together through the substituents; L', each occurrence of which may be the same or different, is a bidentate chelating auxiliary ligand, preferably a monoanionic bidentate chelating ligand; q1 may be 0, 1, 2, or 3, and preferably 2 or 3; q2 may be 0, 1, 2, or 3, and preferably 1 or 0.

[0144] Examples of materials and applications of some triplet emitters can be found in the following patent documents and literature: WO200070655, WO200141512, WO200202714, WO200215645, EP1191613, EP1191612, EP1191614, WO2005033244, WO2005019373, US20050258742, WO2009146770, WO2010015307, WO2010031485, WO2010054731, WO2010054728, WO2010086089, WO2010099852, 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. Chem. Lett. 657, 1990, US20070252517A1, Johnson et al., JACS 105, 1983, 1795, Wrighton, JACS 96, 1974, 998, Ma et al., Synth. Metals 94, 1998, 245, US6824895, US7029766, US6835469, US6830828, US20010053462A1, WO2007095118A1, US2012004407A1, WO2012007088A1, WO2012007087A1, WO2012007086A1, US2008027220A1, WO2011157339A1, CN102282150A, WO2009118087A1, WO2013107487A1, WO2013094620A1, WO2013174471A1, WO2014031977A1, WO2014112450A1, WO2014007565A1, WO2014038456A1, WO2014024131A1, WO2014008982A1, WO2014023377A1. The entire contents of the above - listed patent documents and literature are hereby incorporated herein by reference.

[0145] Examples of some suitable triplet emitters are listed below:

[0146]

[0147] 3. TADF Materials

[0148] Traditional organic fluorescent materials can only utilize 25% of the singlet excitons formed by electrical excitation for luminescence, resulting in a relatively low internal quantum efficiency of the device (up to 25%). Although phosphorescent materials can enhance intersystem crossing due to the strong spin-orbit coupling of heavy atom centers, effectively utilize both singlet and triplet excitons formed by electrical excitation, and achieve an internal quantum efficiency of 100% for the device. However, issues such as the high cost of phosphorescent materials, poor material stability, and severe efficiency roll-off of the device limit their application in OLEDs. Thermally activated delayed fluorescence (TADF) materials are the third generation of organic light-emitting materials developed after organic fluorescent materials and organic phosphorescent materials. Such materials generally have a small singlet-triplet energy gap (ΔE ST ), and triplet excitons can be converted into singlet excitons for luminescence through reverse intersystem crossing. This can make full use of both singlet and triplet excitons formed under electrical excitation. The internal quantum efficiency of the device can reach 100%. At the same time, the material structure is controllable, the properties are stable, the price is cheap without the need for precious metals, and it has broad application prospects in the field of OLEDs.

[0149] TADF materials need to have a small singlet-triplet energy gap, preferably ΔE ST < 0.3 eV, second preferably ΔE ST < 0.2 eV, and most preferably ΔE ST < 0.1 eV. In a preferred embodiment, the TADF material has a relatively small ΔE ST, in another preferred embodiment, the TADF has a good fluorescence quantum efficiency. Some TADF-emitting 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. Mater., 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] Examples of some suitable TADF-emitting materials are listed below:

[0151]

[0152]

[0153] 4. HTM Materials

[0154] Suitable organic HTM materials may optionally include compounds having the following structural units: phthalocyanine, porphyrin, amine, aromatic amine, terphenyltriarylamine, thiophene, bithiophene, pyrrole, aniline, carbazole, indolocarbazole, and their derivatives.

[0155] Examples of cyclic aromatic amine-derived compounds that can be used as HTM include (but are not limited to) the following general structures:

[0156]

[0157] Each Ar 1 -Ar 9 can be independently selected from cyclic aromatic hydrocarbon compounds such as benzene, biphenyl, triphenylbenzene, benzophenanthrene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene; aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, furan, thiophene, benzofuran, benzothiophene, carbazole, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, phthalazine, quinazoline, quinoxaline, naphthyridine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, dibenzoselenophene, benzoselenophene, benzofuranpyridine, indolocarbazole, pyridineindole, pyrroledipyridine, furandipyridine, benzothiophenpyridine, thiophenpyridine, benzoselenophenpyridine, and selenophenedipyridine; groups having a 2- to 10-ring structure, which can be the same or different types of cyclic aromatic hydrocarbon groups or aromatic heterocyclic groups, and are linked to each other directly or through at least one of the following groups, such as an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an alicyclic group. Among them, Ar 1 -Ar 9 can be further substituted, and the substituents can be selected from hydrogen, deuterium, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl, or heteroaryl.

[0158] In some embodiments, Ar 1 -Ar 9 can be independently selected from groups having the following structural units:

[0159]

[0160] where: n 1 is an integer from 1 to 20; X 1 to X 8 is CH or N; the definition of Ar 10 is the same as Ar 1 .

[0161] Additional examples of cycloaromatic amine-derived compounds can be found in US3567450, US4720432, US5061569, and US3615404.

[0162] Examples of suitable HTM compounds are listed below:

[0163]

[0164]

[0165] The present invention also relates to a composition comprising at least one organic compound or polymer or mixture as described above, and at least one organic solvent; the at least one organic solvent is selected from aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, cycloaliphatic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

[0166] In a preferred embodiment, in a composition according to the present invention, the at least one organic solvent is selected from aromatic or heteroaromatic-based solvents.

[0167] Examples of aromatic or heteroaromatic-based solvents suitable for the present invention include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, 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, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 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, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0168] Examples of aromatic ketone solvents suitable for the present invention include, but are not limited to: 1-tetralone, 2-tetralone, 2-(phenyl epoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0169] Examples of aromatic ether solvents suitable for the present invention include, but are not limited to: 3-phenoxytoluene, butoxybenzene, 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-ethylphenetole, 1,3-dipropoxybenzene, 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.

[0170] In some preferred embodiments, in the composition according to the present invention, the at least one organic solvent may be selected from: aliphatic ketones, such as, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as, pentyl 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.

[0171] In some other preferred embodiments, in the composition according to the present invention, the at least one organic solvent may be selected from ester-based solvents: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate are particularly preferred.

[0172] The organic solvent may be used alone or as a mixture of two or more organic solvents.

[0173] In certain preferred embodiments, a composition according to the present invention comprises at least one organic compound or polymer or mixture as described above and at least one organic solvent, and may further comprise another organic solvent. Examples of the another 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.

[0174] In some preferred embodiments, solvents particularly suitable for the present invention are solvents having Hansen solubility parameters in the following ranges:

[0175] δd (dispersion force) is in the range of 17.0 to 23.2 MPa 1 / 2 and particularly in the range of 18.5 to 21.0 MPa 1 / 2 ;

[0176] δp (polar force) is in the range of 0.2 to 12.5 MPa 1 / 2 and particularly in the range of 2.0 to 6.0 MPa 1 / 2 ;

[0177] δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa 1 / 2 and particularly in the range of 2.0 to 6.0 MPa 1 / 2 ;

[0178] For the composition according to the present invention, the organic solvent is selected considering its boiling point parameter. In the present invention, the boiling point of the organic solvent ≥ 150 °C; preferably ≥ 180 °C; more preferably ≥ 200 °C; even more preferably ≥ 250 °C; most preferably ≥ 275 °C or ≥ 300 °C. Boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet print head. The organic solvent can evaporate from the solvent system to form a thin film containing the functional material.

[0179] In a preferred embodiment, the composition according to the present invention is a solution.

[0180] In another preferred embodiment, the composition according to the present invention is a suspension.

[0181] The composition in the embodiments of the present invention may include 0.01 wt% to 10 wt% of the organic compound or polymer or mixture according to the present invention, preferably 0.1 wt% to 10 wt%, more preferably 0.2 wt% to 5 wt%, and most preferably 0.25 wt% to 3 wt%.

[0182] 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 the preparation method by printing or coating.

[0183] 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, reverse roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brushing or pad printing, slot die coating, etc. Gravure printing, nozzle printing and inkjet printing are preferred. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, water repellents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc. Regarding printing techniques and their related requirements for relevant solutions, such as solvents and concentrations, viscosities, etc.

[0184] The present invention also provides an application of the above-mentioned organic compound, mixture or composition in an organic electronic device. The organic electronic device may be selected from, but is not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting electrochemical cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes, etc., and is particularly preferably an OLED. In the embodiments of the present invention, the aromatic amine compound is preferably used in the hole transport layer of an OLED device.

[0185] The present invention further relates to an organic electronic device comprising at least one of the above-mentioned organic compounds or polymers or mixtures. Further, the organic electronic device comprises at least one functional layer, and the functional layer comprises one of the above-mentioned organic compounds or polymers or mixtures or is prepared from the above-mentioned composition. Further, the organic electronic device comprises a cathode, an anode and at least one functional layer, and the functional layer comprises one of the above-mentioned organic compounds or polymers or mixtures or is prepared from the above-mentioned composition. The functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL) or a hole blocking layer (HBL); preferably, the functional layer is selected from a hole transport layer.

[0186] The organic electronic device may be selected from, but is not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting electrochemical cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emitting diodes, etc., and particularly preferably an organic electroluminescent device, such as an OLED, an OLEEC, an organic light-emitting field-effect transistor.

[0187] Further, the organic electronic device is an organic electroluminescent device and includes: a first electrode; a hole transport region disposed on the first electrode; a light-emitting layer disposed on the hole transport region; an electron transport region disposed on the emission layer; and a second electrode disposed on the electron transport region; the hole transport region contains at least one of the organic compounds, polymers, or mixtures described above.

[0188] In certain embodiments, the hole transport region has a multilayer structure, and the layer in the multilayer structure that contacts the light-emitting layer contains the organic compounds, polymers, or mixtures described above.

[0189] In certain embodiments, the hole transport region includes: a hole injection layer disposed on the first electrode; a hole transport layer disposed on the hole injection layer; and a hole assisting layer disposed on the hole transport layer, and the hole transport layer or the hole assisting layer contains the organic compounds, polymers, or mixtures described above.

[0190] In the above-described light-emitting device, particularly an OLED, it includes a substrate, an anode, at least one light-emitting layer, and a cathode.

[0191] The substrate can be opaque or transparent. A transparent substrate can be used to fabricate a transparent light-emitting component. 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 flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface. A substrate without surface defects is a particularly ideal choice. In a preferred embodiment, the substrate is flexible and can be selected from polymer films or plastics with a glass transition temperature (Tg) of 150 °C or higher, preferably exceeding 200 °C, more preferably exceeding 250 °C, and most preferably exceeding 300 °C. Examples of suitable flexible substrates include polyethylene terephthalate (PET) and polyethylene glycol (2,6-naphthalene) (PEN).

[0192] The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known, and those of ordinary skill in the art can easily select and use them. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present invention.

[0193] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL, ETL, or directly into the light-emitting layer. In a preferred embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the light-emitting body 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 the cathode of an OLED can potentially be used as the cathode material of 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 alloy, BaF 2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0194] The OLED may also include other functional layers, such as a hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), electron injection layer (EIL), electron transport layer (ETL), and 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 herein by reference.

[0195] Another aspect of the present invention relates to an organic electroluminescent device including a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein one of the organic layers contains an organic compound represented by the general formula (I).

[0196] The organic electroluminescent device can be manufactured using suitable materials known in the art by suitable methods known in the art, except that the organic compound of the general formula (I) is used to form the corresponding organic layer.

[0197] The organic layer of the organic electroluminescent device according to the present invention has a single-layer or multi-layer structure. For example, the organic layer can be a hole injection layer, a hole transport layer, a hole assisting layer, a light-emitting layer, an electron transport layer, and an electron injection layer. However, the number of organic layers is not limited and can be increased or decreased.

[0198] According to an embodiment of the present invention, the organic electroluminescent device can include a substrate, a first electrode, a first hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a second electrode, wherein a hole assisting layer containing the compound represented by the general formula (I) is interposed between the hole transport layer and the light-emitting layer. Due to the presence of the organic compound represented by the general formula (I), the hole transport to the light-emitting layer is facilitated, and further improvement in the light-emitting efficiency and lifetime characteristics of the device is achieved.

[0199] A more detailed description of the embodiments of the organic electroluminescent device according to the present invention will be given below.

[0200] The organic electroluminescent device of the present invention includes an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. The organic electroluminescent device of the present invention may also optionally include a hole injection layer between the anode and the hole transport layer and an electron injection layer between the electron transport layer and the cathode. If necessary, the organic electroluminescent device of the present invention may also include one or two intermediate layers. The intermediate layer can be a hole blocking layer or an electron blocking layer. The organic electroluminescent device of the present invention may also include one or more organic layers having various functions according to the desired characteristics of the device.

[0201] The organic electroluminescent device of the present invention may also include a hole assisting layer between the hole transport layer and the light-emitting layer, wherein the hole assisting layer may contain an organic compound represented by the general formula (I).

[0202] The organic electroluminescent device according to the present invention has a light-emitting wavelength between 300 nm and 1200 nm, preferably between 350 nm and 1000 nm, more preferably between 400 nm and 900 nm.

[0203] The present invention also relates to the application 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.

[0204] Examples

[0205] The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims define the scope of the present invention. Those skilled in the art should be aware that certain changes made to the embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

[0206] 1. Synthesis of compounds

[0207]

[0208] Synthesis of Compound 1-1: Accurately weigh adamantane-2,6-dione (16.4 g, 100 mmol) and add it to 100 mL of anhydrous tetrahydrofuran. After evacuating and purging three times in a cycle, cool the temperature to -78 °C, and then dropwise add phenylmagnesium chloride tetrahydrofuran solution (1 M, 200 mL) to the above solution under a nitrogen atmosphere. Allow the temperature to rise to room temperature naturally and react overnight. After the reaction is completed, add an appropriate amount of saturated ammonium chloride solution to quench the reaction at low temperature. After liquid separation, the organic phase is concentrated, mixed with silica gel, and subjected to column chromatography (n-hexane:dichloromethane = 50:1). After concentration, 21.5 g of Compound 1-1 is obtained, with a yield of 67%. MS (ASAP) = 320.4.

[0209] Synthesis of Compound 1-2: Weigh Compound 1-1 (16.5 g, 51.55 mmol) into a reaction flask, add 250 mL of anhydrous dichloromethane to dissolve it, evacuate and replace with nitrogen three times, cool the temperature to -10 °C, add triethylamine (20.9 g, 206.2 mmol), stir for 30 minutes, add trifluoromethanesulfonic anhydride (58.2 g, 206.2 mmol), and gradually raise the temperature to room temperature and stir the reaction overnight. After the reaction is completed, add 100 mL of water and stir for 30 minutes. Separate the aqueous layer, and directly pass the organic layer through a short silica gel column and concentrate to obtain 25.6 g of Compound 1-2, with a yield of 85%. MS (ASAP) = 584.5.

[0210] Synthesis of Compound 1: In a dry two-necked flask, add Compound 1-2 (22.9 g, 39.16 mmol), triphenylamine-4-boronic acid (24.9 g, 86.15 mmol) and palladium tetrakis(triphenylphosphine) (2.26 g, 1.96 mmol). Then add aqueous potassium carbonate solution (2 M, 200 mL) and 1,4-dioxane 500 mL. Evacuate and refill with nitrogen three times, and stir the reaction at 80 °C overnight. After the reaction is completed, allow the reaction solution to cool to room temperature, add 300 mL of water, then extract with dichloromethane. Combine the organic phases and dry over anhydrous sodium sulfate. After concentration, load the sample on silica gel for column chromatography (n-hexane:dichloromethane = 10:1), and concentrate to obtain 23.4 g of Compound 1 with a yield of 77%. MS (ASAP) = 775.1.

[0211]

[0212] Synthesis of Compound 2: In a dry two-necked flask, add Compound 1-2 (22.9 g, 39.16 mmol), triphenylamine-3-boronic acid (24.9 g, 86.15 mmol) and palladium tetrakis(triphenylphosphine) (2.26 g, 1.96 mmol). Then add aqueous potassium carbonate solution (2 M, 200 mL) and 1,4-dioxane 500 mL. Evacuate and refill with nitrogen three times, and stir the reaction at 80 °C overnight. After the reaction is completed, allow the reaction solution to cool to room temperature, add 300 mL of water, then extract with dichloromethane. Combine the organic phases and dry over anhydrous sodium sulfate. After concentration, load the sample on silica gel for column chromatography (n-hexane:dichloromethane = 10:1), and concentrate to obtain 22.5 g of Compound 2 with a yield of 74%. MS (ASAP) = 775.1.

[0213]

[0214] Synthesis of Compound 3-1: In a dry two-necked flask, add Compound 1-2 (22.9 g, 39.16 mmol), phenylboronic acid (4.77 g, 39.16 mmol) and palladium tetrakis(triphenylphosphine) (1.13 g, 0.98 mmol). Then add aqueous potassium carbonate solution (2 M, 200 mL) and 1,4-dioxane 500 mL. Evacuate and refill with nitrogen three times, and stir the reaction at 80 °C for 2 hours. After the reaction is completed, allow the reaction solution to cool to room temperature, add 300 mL of water, then extract with dichloromethane. Combine the organic phases and dry over anhydrous sodium sulfate. After concentration, load the sample on silica gel for column chromatography (n-hexane:dichloromethane = 50:1), and concentrate to obtain 18.1 g of Compound 3-1 with a yield of 90%. MS (ASAP) = 512.6.

[0215] Synthesis of compound 3-2: Add compound 3-1 (17.9 g, 35 mmol), 3-chlorophenylboronic acid (6.0 g, 38.5 mmol) and tetrakistriphenylphosphine palladium (1.61 g, 0.7 mmol) into a dry two-necked bottle, then add potassium carbonate aqueous solution (2M, 200 mL) and 1,4-dioxane 500 mL, evacuate and circulate nitrogen for three times, stir and react at 80°C overnight. After the reaction is completed, the reaction solution is cooled to room temperature, 300 mL of water is added, and then extracted with dichloromethane, the organic phases are combined and dried with anhydrous sodium sulfate, concentrated, and then mixed with silica gel column chromatography (n-hexane: dichloromethane = 40:1), and concentrated to obtain 14.5 g of compound 3-2, with a yield of 87%. MS (ASAP) = 475.1.

[0216] Synthesis of compound 3: Accurately weigh di(4-biphenyl)amine (10.6 g, 33 mmol), compound 3-2 (14.3 g, 30 mmol), tri(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol) and sodium tert-butoxide (6.73 g, 70 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 10:1), and concentrate to obtain 19.4 g of compound 3, with a yield of 85%. MS (ASAP) = 760.0.

[0217]

[0218] Synthesis of compound 4-1: Accurately weigh 4-aminobiphenyl (8.46 g, 50 mmol), 2-bromo-9,9-dimethylfluorene (13.7 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (1.37 g, 1.5 mmol), tricyclohexylphosphine (0.84 g, 3 mmol) and sodium tert-butoxide (9.61 g, 100 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 4:1), and concentrate to obtain 13.9 g of compound 4-1, with a yield of 77%. MS (ASAP) = 361.5.

[0219] Synthesis of compound 4: Accurately weigh compound 3-2 (14.3 g, 30 mmol), compound 4-1 (10.8 g, 30 mmol), tri(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol) and sodium tert-butoxide (5.77 g, 60 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 3:1), and concentrate to obtain 20.2 g of compound 4, with a yield of 84%. MS (ASAP) = 800.1.

[0220]

[0221] Synthesis of compound 5-1: Add compound 3-1 (17.9 g, 35 mmol), 4-chlorophenylboronic acid (6.0 g, 38.5 mmol) and tetrakistriphenylphosphine palladium (1.61 g, 0.7 mmol) into a dry two-necked bottle, then add potassium carbonate aqueous solution (2M, 200 mL) and 500 mL of 1,4-dioxane, evacuate and circulate nitrogen for three times, stir and react at 80°C overnight. After the reaction is completed, the reaction solution is cooled to room temperature, 300 mL of water is added, and then extracted with dichloromethane. The organic phases are combined and dried with anhydrous sodium sulfate, concentrated, and then mixed with silica gel column chromatography (n-hexane: dichloromethane = 40:1), and concentrated to obtain 14.5 g of compound 5-1, with a yield of 87%. MS (ASAP) = 475.1.

[0222] Synthesis of compound 5: Accurately weigh di(4-biphenyl)amine (10.6 g, 33 mmol), compound 5-1 (14.3 g, 30 mmol), tri(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol) and sodium tert-butoxide (5.77 g, 60 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 10:1), and concentrate to obtain 19.4 g of compound 5, with a yield of 85%. MS (ASAP) = 760.0.

[0223]

[0224] Synthesis of compound 6-1: Accurately weigh 2-bromobiphenyl (11.7 g, 50 mmol), 2-amino-9,9-dimethylfluorene (10.5 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (1.37 g, 1.5 mmol), tricyclohexylphosphine (0.84 g, 3 mmol) and sodium tert-butoxide (9.61 g, 100 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 4:1), and concentrate to obtain 14.3 g of compound 6-1, with a yield of 79%. MS (ASAP) = 361.5.

[0225] Synthesis of compound 6: Accurately weigh compound 6-1 (11.9 g, 33 mmol), compound 5-1 (14.3 g, 30 mmol), tri(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol) and sodium tert-butoxide (5.77 g, 60 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 10:1), and concentrate to obtain 19.2 g of compound 6, with a yield of 80%. MS (ASAP) = 800.1.

[0226]

[0227] Synthesis of compound 7-1: Accurately weigh 1-bromodibenzofuran (12.4 g, 50 mmol), 2-amino-9,9-dimethylfluorene (10.5 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (1.37 g, 1.5 mmol), tricyclohexylphosphine (0.84 g, 3 mmol) and sodium tert-butoxide (9.61 g, 100 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 4:1), and concentrate to obtain 16.5 g of compound 7-1, with a yield of 88%. MS (ASAP) = 375.5.

[0228] Synthesis of compound 7: Accurately weigh compound 7-1 (12.4 g, 33 mmol), compound 5-1 (14.3 g, 30 mmol), tri(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol) and sodium tert-butoxide (5.77 g, 60 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 10:1), and concentrate to obtain 20.5 g of compound 7, with a yield of 84%. MS (ASAP) = 814.1.

[0229]

[0230] Synthesis of compound 8-1: 1-bromo-3-chloronaphthalene (12.1 g, 50 mmol), biboronic acid pinacol ester (15.24 g, 60 mmol), potassium acetate (24.54 g, 250 mmol), [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium (1.83 g, 2.5 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.2 g, 2.5 mmol) were added to a dry reaction bottle, 250 mL of 1,4-dioxane was added to dissolve, vacuum nitrogen was replaced three times, and the temperature was raised to 85 ° C to react overnight. After the reaction was completed, it was cooled to room temperature, filtered, and the mother liquor was concentrated. It was dissolved with 400 mL of dichloromethane and then decolorized by passing through a short silica gel column. After concentration, silica gel mixed sample column chromatography (n-hexane: dichloromethane = 40:1) was obtained to obtain 12.4 g of compound 8-1, with a yield of 86%. MS (ASAP) = 288.6.

[0231] Synthesis of compound 8-2: Add compound 8-1 (11.3 g, 39.16 mmol), compound 3-1 (20.1 g, 39.16 mmol) and tetrakistriphenylphosphine palladium (2.26 g, 1.96 mmol) into a dry two-necked bottle, then add potassium carbonate aqueous solution (2M, 200 mL) and 500 mL of 1,4-dioxane, evacuate and circulate nitrogen for three times, stir and react at 80°C overnight. After the reaction is completed, the reaction solution is cooled to room temperature, 300 mL of water is added, and then extracted with dichloromethane. The organic phases are combined and dried with anhydrous sodium sulfate, concentrated, and then mixed with silica gel column chromatography (n-hexane: dichloromethane = 40:1), and concentrated to obtain 17.9 g of compound 8-2, with a yield of 87%. MS (ASAP) = 525.1.

[0232] Synthesis of compound 8: Accurately weigh di(4-biphenyl)amine (10.6 g, 33 mmol), compound 8-2 (15.8 g, 30 mmol), tri(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol) and sodium tert-butoxide (5.77 g, 60 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 3:1), and concentrate to obtain 20.7 g of compound 8, with a yield of 85%. MS (ASAP) = 810.1.

[0233]

[0234] Synthesis of compound 9-1: 3,5-dichloro-1-bromobenzene (11.3 g, 50 mmol), biboronic acid pinacol ester (12.7 g, 50 mmol), potassium acetate (24.54 g, 250 mmol), [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium (1.83 g, 2.5 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.2 g, 2.5 mmol) were added to a dry reaction bottle, 250 mL of 1,4-dioxane was added to dissolve, vacuum nitrogen was replaced three times, and the temperature was raised to 85 ° C to react overnight. After the reaction was completed, it was cooled to room temperature, filtered, and the mother liquor was concentrated. It was dissolved with 400 mL of dichloromethane and then decolorized by passing through a short silica gel column. After concentration, silica gel mixed sample column chromatography (n-hexane) was concentrated to obtain 11.9 g of compound 9-1, with a yield of 87%. MS (ASAP) = 273.0.

[0235] Synthesis of compound 9-2: Add compound 3-1 (20.1 g, 39.16 mmol), compound 9-1 (10.7 g, 39.16 mmol) and tetrakistriphenylphosphine palladium (2.26 g, 1.96 mmol) into a dry two-necked bottle, then add potassium carbonate aqueous solution (2M, 200 mL) and 1,4-dioxane 500 mL, evacuate and circulate nitrogen for three times, stir and react at 80°C overnight. After the reaction is completed, the reaction solution is cooled to room temperature, 300 mL of water is added, and then extracted with dichloromethane, the organic phases are combined and dried with anhydrous sodium sulfate, concentrated, and then mixed with silica gel column chromatography (n-hexane: dichloromethane = 10:1), and concentrated to obtain 16.4 g of compound 9-2, with a yield of 82%. MS (ASAP) = 509.5.

[0236] Synthesis of compound 9: Accurately weigh N-phenyl-4-benzidine (16.2 g, 66 mmol), compound 9-2 (10.7 g, 30 mmol), tri(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol) and sodium tert-butoxide (5.77 g, 60 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 3:1), and concentrate to obtain 23.6 g of compound 9, with a yield of 85%. MS (ASAP) = 927.3.

[0237]

[0238] Synthesis of compound 10-1: Add 5-bromo-2-iodobenzoic acid methyl ester (34.1g, 100mmol), 2,4-dichlorophenylboronic acid (19.1g, 100mmol) and tetrakistriphenylphosphine palladium (3.47g, 3mmol) into a dry double-necked bottle, then add potassium carbonate aqueous solution (2M, 250mL) and 1,4-dioxane 500mL, evacuate and circulate nitrogen for three times, stir and react at 80℃ overnight. After the reaction is completed, the reaction solution is cooled to room temperature, 300mL of water is added, and then extracted with dichloromethane. The organic phases are combined and dried with anhydrous sodium sulfate, concentrated, and then mixed with silica gel column chromatography (n-hexane: dichloromethane = 10:1), and concentrated to obtain 31.7g of compound 10-1, with a yield of 88%. MS (ASAP) = 360.0.

[0239] Synthesis of compound 10-2: The preparation method of the compound refers to patent CN113045553. Add compound 10-1 (28.8 g, 80 mmol) to a dry reaction bottle, add 100 mL of anhydrous tetrahydrofuran to dissolve. After vacuuming and nitrogen filling for three cycles, cool to -40 ° C, and add methyl magnesium bromide tetrahydrofuran solution (1M, 88 mL) to the above solution. After the addition is completed, naturally warm to room temperature and react overnight. After the reaction is completed, add a little water to quench the reaction. After the organic phase is concentrated, the intermediate is obtained. Add the above intermediate and 100 mL of trifluoromethanesulfonic anhydride to a dry reaction bottle, heat to 120 ° C, and react overnight. After the reaction is completed, cool to 0 ° C, add water to quench the reaction, and solid precipitates. Filter, and the crude product is recrystallized from toluene to obtain 20.5 g of compound 10-2, with a yield of 75%. MS (ASAP) = 342.1.

[0240] Synthesis of compound 10-3: Add compound 10-2 (17.1 g, 50 mmol), biboronic acid pinacol ester (12.7 g, 50 mmol), potassium acetate (24.54 g, 250 mmol), [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (1.83 g, 2.5 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.2 g, 2.5 mmol) to a dry reaction bottle, add 250 mL of 1,4-dioxane to dissolve, evacuate and replace with nitrogen three times, heat to 85 ° C and react overnight. After the reaction is completed, cool to room temperature, filter, concentrate the mother liquor, dissolve with 400 mL of dichloromethane, pass through a short silica gel column for decolorization, concentrate and mix with silica gel column chromatography (n-hexane: dichloromethane = 5:1), and concentrate to obtain 17.7 g of compound 10-3, with a yield of 91%. MS (ASAP) = 389.1.

[0241] Synthesis of compound 10-4: Add compound 3-1 (20.1 g, 39.16 mmol), compound 10-3 (15.2 g, 39.16 mmol) and tetrakistriphenylphosphine palladium (2.26 g, 1.96 mmol) into a dry two-necked bottle, then add potassium carbonate aqueous solution (2M, 250 mL) and 1,4-dioxane 500 mL, evacuate and circulate nitrogen for three times, stir and react at 80°C overnight. After the reaction is completed, the reaction solution is cooled to room temperature, 300 mL of water is added, and then extracted with dichloromethane. The organic phases are combined and dried with anhydrous sodium sulfate, concentrated, and then mixed with silica gel column chromatography (n-hexane: dichloromethane = 10:1), and concentrated to obtain 19.1 g of compound 10-4, with a yield of 78%. MS (ASAP) = 625.7.

[0242] Synthesis of compound 10: Accurately weigh diphenylamine (11.2 g, 66 mmol), compound 10-4 (18.8 g, 30 mmol), tri(dibenzylideneacetone)dipalladium (1.84 g, 2 mmol), tri-tert-butylphosphine (1.12 g, 4 mmol) and sodium tert-butoxide (12.5 g, 140 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 8:1), and concentrate to obtain 19.5 g of compound 10, with a yield of 73%. MS (ASAP) = 891.2.

[0243]

[0244] Synthesis of compound 11-1: Accurately weigh 2-bromo-4'-chloro-biphenyl (26.7g, 100mmol), dissolve it in 50mL of anhydrous tetrahydrofuran, evacuate and fill with nitrogen for three cycles, cool to -78℃, slowly drop n-butyl lithium (1.6M, 75mL), control the temperature below -78℃, keep warm for 2h, then slowly drop a solution of adamantane-2,6-dione (8.2g, 50mmol) dissolved in anhydrous tetrahydrofuran, control the temperature below -78℃, keep warm for 1h after the addition, then naturally warm to room temperature and stir overnight. Add methanol to quench the reaction, concentrate, add ethanol to pulp, white solid precipitates, filter, and obtain 16.2g of crude compound 11-1, with a yield of 60%. MS (ASAP) = 541.5.

[0245] Synthesis of compound 11-2: Accurately weigh compound 11-1 (16.2, 30 mmol) and add it to a dry three-necked flask, add 120 mL of glacial acetic acid and 120 mL of concentrated hydrochloric acid, heat to 100°C, and reflux for 2 hours. Then cool to room temperature, neutralize with saturated sodium carbonate aqueous solution, extract with DCM, combine the organic phases, concentrate, add ethanol to pulp, white solid precipitates, filter, and obtain 13.5 g of crude compound 11-2, with a yield of about 89%. MS (ASAP) = 505.5.

[0246] Synthesis of compound 11: Accurately weigh N-phenyl-4-benzidine (13.5 g, 55 mmol), compound 11-2 (12.6 g, 25 mmol), tri(dibenzylideneacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol) and sodium tert-butoxide (4.5 g, 50 mmol) and add them to a 250 mL two-necked flask, and add 100 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 5:1), and concentrate to obtain 16.8 g of compound 11, with a yield of 73%. MS (ASAP) = 923.2.

[0247]

[0248] Synthesis of Compound 12-1: Weigh accurately adamantane-2,6-dione (16.4 g, 100 mmol) and add it to 100 mL of anhydrous tetrahydrofuran. After evacuating and purging with nitrogen three times in a cycle, cool the solution to -78 °C, and then dropwise add phenylmagnesium chloride tetrahydrofuran solution (1 M, 100 mL) to the above solution under a nitrogen atmosphere. Let it warm up to room temperature naturally and react overnight. After the reaction is completed, add an appropriate amount of saturated ammonium chloride solution to quench the reaction at low temperature. After liquid separation, concentrate the organic phase, mix it with silica gel, and perform column chromatography (n-hexane:dichloromethane = 50:1). After concentration, 20.4 g of Compound 12-1 is obtained, with a yield of 84%. MS (ASAP) = 242.3.

[0249] Synthesis of Compound 12-2: Weigh Compound 12-1 (12.5 g, 51.55 mmol) into a reaction flask, add 250 mL of anhydrous dichloromethane to dissolve it clearly. Evacuate and cycle with nitrogen three times, cool to -10 °C, add triethylamine (10.4 g, 103.1 mmol), stir for 30 minutes, add trifluoromethanesulfonic anhydride (29.1 g, 103.1 mmol), and gradually warm up to room temperature and stir the reaction overnight. After the reaction is completed, add 100 mL of water and stir for 30 minutes. Separate the aqueous layer, directly pass the organic layer through a short silica gel column, and concentrate to obtain 17.4 g of Compound 12-2, with a yield of 90%. MS (ASAP) = 374.4.

[0250] Synthesis of Compound 12-3: Add Compound 12-2 (13.1 g, 35 mmol), phenylboronic acid (4.7 g, 38.5 mmol), and tetrakis(triphenylphosphine)palladium (1.61 g, 0.7 mmol) to a dry two-necked flask. Then add aqueous potassium carbonate solution (2 M, 25 mL) and 1,4-dioxane 100 mL. Evacuate and fill with nitrogen three times in a cycle, stir the reaction at 80 °C overnight. After the reaction is completed, wait for the reaction solution to cool to room temperature, add 20 mL of water, then extract with dichloromethane. Combine the organic phases, dry with anhydrous sodium sulfate, concentrate, mix with silica gel, and perform column chromatography (n-hexane:dichloromethane = 40:1). After concentration, 9.9 g of Compound 12-3 is obtained, with a yield of 94%. MS (ASAP) = 302.4.

[0251] Synthesis of compound 12-4: Accurately weigh 2-bromo-4,4'-dichloro-1,1'-biphenyl (9.67g, 32mmol), dissolve it in 20mL of anhydrous tetrahydrofuran, evacuate and charge with nitrogen for three cycles, cool to -78°C, slowly drop n-butyl lithium (1.6M, 20mL), control the temperature below -78°C, keep warm for 2h, then slowly drop compound 12-3 (9.07g, 30mmol) solution dissolved in anhydrous tetrahydrofuran, control the temperature below -78°C, keep warm for 1h after the addition, then naturally warm to room temperature and stir overnight. Add methanol to quench the reaction, concentrate, add ethanol to pulp, white solid precipitates, filter, and obtain a total of 11.0g of crude compound 12-4 with a yield of 70%. MS (ASAP) = 525.5.

[0252] Synthesis of compound 12-5: Accurately weigh compound 12-4 (10.5 g, 20 mmol) and add it to a dry three-necked flask, add 80 mL of glacial acetic acid and 80 mL of concentrated hydrochloric acid, heat to 100°C, and reflux for 2 h. Then cool to room temperature, neutralize with saturated sodium carbonate aqueous solution, extract with DCM, combine the organic phases, concentrate, add ethanol to pulp, white solid precipitates, filter, and obtain 9.1 g of crude compound 12-5, with a yield of about 90%. MS (ASAP) = 507.5.

[0253] Synthesis of compound 12: Accurately weigh N-phenyl-4-benzidine (8.10 g, 33 mmol), compound 12-5 (7.61 g, 15 mmol), tri(dibenzylideneacetone)dipalladium (0.64 g, 0.7 mmol), tri-tert-butylphosphine (0.39 g, 1.4 mmol) and sodium tert-butoxide (2.7 g, 30 mmol) and add them into a 250 mL two-necked flask, and add 60 mL of anhydrous toluene to dissolve. After three cycles of ventilation, heat to reflux and react overnight. After the reaction is completed, cool to room temperature, add a little water to quench the reaction, concentrate, mix with silica gel, and column chromatography (n-hexane: dichloromethane = 5:1), and concentrate to obtain 10.8 g of compound 12, with a yield of 78%. MS (ASAP) = 925.2.

[0254] 2. Energy structure of organic compounds

[0255] The energy levels of the organic materials can be obtained by quantum calculation, such as using TD-DFT (Time-Dependent Density Functional Theory) through Gaussian 09W (Gaussian Inc.). For the specific simulation method, reference can be made to WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet), and then the energy structure of the organic molecule is calculated by the TD-DFT (Time-Dependent Density Functional Theory) method "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated according to the following calibration formula, and S1 and T1 are used directly.

[0256] HOMO (eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206

[0257] LUMO (eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385

[0258] Where HOMO(G) and LUMO(G) are the direct calculation results of Gaussian 09W, with the unit of Hartree. The results are shown in Table 1 as follows:

[0259] Table 1

[0260] Material HOMO [eV] LUMO [eV] ΔHOMO [eV] ΔLUMO [eV] T1 [eV] S1 [eV] Compound 1 -5.31 -1.82 0.00 0.02 3.03 3.86 Compound 2 -5.34 -1.82 0.01 0.03 3.09 3.83 Compound 3 -5.30 -2.13 1.11 0.16 2.74 3.51 Compound 4 -5.27 -2.13 1.15 0.13 2.73 3.49 Compound 5 -5.24 -2.17 1.07 0.18 2.62 3.41 Compound 6 -5.26 -2.03 1.02 0.05 2.72 3.47 Compound 7 -5.31 -2.24 0.99 0.17 2.66 3.31 Compound 8 -5.29 -2.30 0.81 0.14 2.42 3.26 Compound 9 -5.26 -2.07 0.19 0.01 2.77 3.54 Compound 10 -5.26 -2.19 0.18 0.35 2.58 3.40 Compound 11 -5.27 -2.19 0.00 0.00 2.61 3.39 Compound 12 -5.25 -2.21 1.03 0.05 2.61 3.31 Comparative Compound 1 -5.23 -1.84 0.18 0.07 2.98 3.74 Comparative Compound 2 -5.32 -2.26 0.89 0.18 2.68 3.27

[0261] 3. Preparation and Characterization of OLED Devices

[0262] The following is a detailed description of the preparation process of the above OLED device through specific examples. The structure of the green light device is PD:HT-1 = 3:100(10) / HT-1(50) / HT-2(40) / GH1:GH2:GD = 50:50:8(25) / ET:LiQ = 50:50(30) / LiQ(1) / Al(100)

[0263]

[0264] a. Cleaning of the ITO (Indium Tin Oxide) conductive glass substrate: Clean it using various solvents (such as one or several of chloroform, acetone, or isopropyl alcohol), and then perform ultraviolet ozone treatment.

[0265] b. Evaporation: Transfer the substrate into a vacuum vapor deposition equipment, and under high vacuum (1×10 -6At a pressure of millibar), the ratio of PD to HT-1 is controlled to be 3:100 to form a 10-nm hole injection layer (HIL). Subsequently, compound HT-1 is evaporated on the hole injection layer to form a 50-nm hole transport layer (HTL). Immediately after that, the organic compound of the present invention is evaporated on the hole transport layer to form a 40-nm hole auxiliary layer. As the light-emitting layer, a 25-nm light-emitting layer thin film is formed with GH1:GH2:GD in a ratio of 50:50:8. Then, ET and LiQ are placed in different evaporation units and co-deposited at a ratio of 50 wt% respectively to obtain a 30-nm electron transport layer. Subsequently, 1 nm of LiQ is deposited as the electron injection layer. Finally, an Al cathode with a thickness of 100 nm is deposited on the electron injection layer.

[0266] c. Encapsulation: The device is encapsulated with an ultraviolet-curing resin in a nitrogen glove box.

[0267] The device performances of the above-mentioned examples and comparative examples are tested, as shown in Table 2 specifically; among them, the driving voltage and current efficiency are tested at a current density of 10 mA / cm 2 The device lifetime of T95 refers to the time when the brightness decays to 95% at a constant current density of 50 mA / cm 2

[0268] Table 2

[0269]

[0270] Compared with Comparative Example 1, in Examples 1 - 12 of the device, due to the presence of the organic compound of the present invention as the hole auxiliary layer material, the driving voltage can be effectively reduced, the emission efficiency can be improved, and the device lifetime can be extended.

[0271] Even if the hole auxiliary layer is also included, compared with Comparative Examples 2 - 3, Examples 1 - 12 of the device have obvious improvements in both current efficiency and lifetime, indicating the beneficial effects of the organic compound of the present invention applied to OLED devices.

[0272] The core structure of the present invention is that the triarylamine group and the aryl group are connected by the adamantyl group in the 2,2-substituted and 6,6-substituted manners. Through the space conjugation effect, the compound molecule has a suitable HOMO energy level and hole mobility, which is applicable to the hole transport region of organic electroluminescent devices, especially suitable for the hole auxiliary layer; at the same time, this molecular structure has good amorphous stacking performance, which can reduce the crystallinity of the material and extend the device lifetime. When the adamantane of the organic compound of the present invention is connected with the arylamine through the aryl group, the device performance is better.

[0273] The above-described embodiments merely represent several implementation manners of the present invention. The description is relatively specific and detailed, but it should not be construed as a limitation on the scope of the invention patent. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can still be made, and these all fall within the protection scope of the present invention. Therefore, the protection scope of the present invention patent shall be subject to the appended claims.

Claims

1. An organic compound having a structure as shown in general formula (I): in, R 1 -R 4 the same or different, independently selected from a linear alkyl, alkoxy, thioalkoxy group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy, thioalkoxy, silyl group having 3 to 20 C atoms, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, or a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, Cl, Br, F, a crosslinkable group, or a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy group or heteroaryloxy group having 5 to 60 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 bonded to the group, and one or more H in the above groups can be further substituted by D; At the same time, R 1 -R 4 At least one of them contains the structure shown in the following general formula (I-1), and R 1 With R 2 Can further form a ring, R 3 With R 4 Can further form rings; * indicates the location of bonding; L 0 , L 1 and L 2 are the same or different and are independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaromatic group having 2 to 30 ring carbon atoms, wherein any adjacent groups may form a ring, and one or more H in the above groups may be further substituted by D; Ar 1 and Ar 2 are the same or different and are independently selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 60 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 60 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 bonded to the group, and one or more H in the above groups can be further substituted by D.

2. The organic compound according to claim 1, having a structure as shown in general formula (II-1) to general formula (II-3): in, Two adjacent L 0 Can further form a ring, adjacent L 0 With R 2 Can further form a ring, adjacent L 0 With R 4 Can be further looped.

3. The organic compound according to claim 1 or 2, having a structure as shown in general formula (III-1) to general formula (III-3): in, L 3 Independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaromatic group having 2 to 30 ring carbon atoms, wherein any adjacent groups may form a ring, and one or more H in the above groups may be further substituted by D; Ar 3 Independently selected from substituted or unsubstituted aromatic or heteroaromatic groups having 5 to 60 ring atoms, or aryloxy or heteroaryloxy groups having 5 to 60 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 bonded to the group, and one or more H in the above groups can be further substituted by D; Adjacent L 0 With L 1 , or adjacent L 0 With L 2 , or adjacent L 1 With L 2 , or adjacent L 0 With L 3 , or adjacent L 0 With L 0 , or adjacent L 3 With L 3 Can be further looped.

4. The organic compound according to any one of claims 1 to 3, wherein L 0 , L 1 , L 2 and L 3 Each is independently selected from a single bond or the following structures and combinations: * indicates the location of bonding; The above structure may be further substituted by 0, 1, 2 or 3 substituents R 0 Substituted, substituent R 0 Selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl or C3-C10 cycloalkyl.

5. The organic compound according to any one of claims 1 to 4, having the following structures of general formula (IV-1) to general formula (IV-36): in, One or more H in the above structure may be further replaced by D; m is an integer independently selected from 1, 2, 3 or 4; X and Y are the same or different and are independently selected from a single bond, O, S, C=O, SiR 5 R 6 , CR 7 R 8 NR 9 or P(R 10 R 11 )=O, where R 5 -R 11 The same definition as R in claim 1 1 .

6. An organic compound according to any one of claims 1 to 5, wherein Ar 1- Ar 3 Selected from the following structures and combinations thereof: The above structure may be further substituted by 0, 1, 2 or 3 substituents R0, wherein the substituents R0 are selected from D, F, Cl, Br, cyano, C1-C4 alkyl, C1-C3 haloalkyl, phenyl, naphthyl, fluorenyl, spirofluorenyl or C3-C10 cycloalkyl; A1 is defined as R in claim 1 1 .

7. A polymer comprising at least one repeating unit, wherein the repeating unit comprises a structure corresponding to the organic compound according to any one of claims 1 to 6.

8. A mixture, characterized in that The method comprises at least one organic compound as described in any one of claims 1 to 6 or a high polymer as described in claim 7, and at least one other organic functional material, wherein the at least one other organic functional material can be selected from hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, organic matrix materials, singlet light emitters, triplet light emitters, thermally excited delayed fluorescence materials or organic dyes.

9. A composition, characterized in that The method comprises at least one organic compound according to any one of claims 1 to 6, or the high polymer according to claim 7, or the mixture according to claim 8, and at least one organic solvent.

10. An organic electronic device, characterized in that: Contains at least one organic compound according to any one of claims 1 to 6, or a polymer according to claim 7, or a mixture according to claim 8.

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