Compound for organic electroluminescent device and use thereof, organic electroluminescent device

Abstract

The present invention provides a deuterium-substituted compound and its use in an organic electroluminescent device. The compound has a structure represented by Formula I, and by linking a specific fused ring structure to a triazine structure, it has excellent electron transport and optoelectronic properties. Furthermore, its low triplet energy level makes it particularly suitable as a host material for the light-emitting layer. It can lower the energy level between the host and guest, reduce energy transfer losses, increase efficiency, and improve overall device performance. Furthermore, the present invention further improves the stability of the molecule by deuterizing the triazine substituent, thereby extending the service life of the device. [Formula 1] JPEG2026504764000093.jpg52170

Description

[Technical Field]

[0001] The present invention belongs to the technical field of organic electroluminescent materials, in particular to compounds and their use in organic electroluminescent devices. [Background technology]

[0002] In recent years, organic material-based optoelectronic devices have developed rapidly and become a hotspot of research in this field. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic solar cells, and organic sensors. OLEDs have developed particularly rapidly and have achieved commercial success in the field of information display. OLEDs can provide highly saturated red, green, and blue colors, and full-color display devices fabricated using OLEDs have the advantages of not requiring additional backlighting, vivid colors, and being thin and flexible.

[0003] The core of an OLED device is a multilayer thin-film structure containing various functional organic materials. Common functional organic materials include hole-injecting materials, hole-transporting materials, hole-blocking materials, electron-injecting materials, electron-transporting materials, electron-blocking materials, emissive host materials, and emissive guest materials (dyes). When electricity is applied, electrons and holes are injected and transported to the emissive region, respectively, where they recombine to generate excitons, which then emit light.

[0004] Current OLEDs can be classified into fluorescent, phosphorescent, thermally excited delayed fluorescence, and thermally activated sensitized fluorescence according to their emission mechanism. Typical fluorescent emitters primarily emit light using singlet excitons generated when electrons and holes combine, and are still widely used in various OLED products. Some metal complexes (e.g., iridium and platinum complexes) can emit light using both triplet and singlet excitons. These are called phosphorescent emitters, and their energy conversion efficiency can be up to four times higher than that of conventional fluorescent emitters. Thermally activated delayed fluorescence (TADF) promotes the conversion of triplet excitons to singlet excitons, effectively utilizing triplet excitons without the use of metal complexes, achieving high luminous efficiency. Thermally activated sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize emitters through energy transfer, also achieving high luminous efficiency.

[0005] Although products using OLED technology have been commercialized, the pursuit of high-quality display effects requires continuous improvement in device characteristics such as lifetime and efficiency. Therefore, there is an urgent need in this field to develop more organic materials with higher properties that can be used in organic electroluminescent devices to improve the device's light-emitting efficiency. Summary of the Invention [Problem to be solved by the invention]

[0006] In view of the shortcomings of the prior art, the object of the present invention is to provide a compound having excellent optoelectronic properties through the design of molecular structure, which is used in organic electroluminescent devices, particularly suitable as a host material for the light-emitting layer, and can effectively extend the service life of the device, and the use thereof, and an organic electroluminescent device. [Means for solving the problem]

[0007] To achieve this goal, the present invention employs the following technical solutions. In a first aspect, the present invention provides a compound having the structure shown in Formula I: JPEG2026504764000002.jpg57170 Formula I (In Formula I, Ar1 and Ar2 are each independently one of a substituted or unsubstituted C6 to C60 aryl and a substituted or unsubstituted C3 to C60 heteroaryl, and at least one hydrogen atom in Ar1 and Ar2 is replaced by a deuterium atom; L1, L2, and L3 each independently represent one of a single bond, a substituted or unsubstituted C6 to C30 alkylene, and a substituted or unsubstituted C3 to C30 heteroarylene; R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , and R 14 each independently represents one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1 to C10 chain alkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl; Ar1, Ar2, L1, L2, L3, and R1 to R 14 The substituted substituents in the formula (I) are each independently one or a combination of at least two selected from deuterium, halogen, C1 to C20 chain alkyl, C2 to C10 alkenyl, C3 to C20 cycloalkyl, C2 to C20 heterocycloalkyl, C1 to C10 alkoxy, carboxy, nitro, cyano, amino, hydroxy, mercapto, C1 to C20 alkylsilyl, C1 to C20 alkylamino, C6 to C30 arylamino, C3 to C30 heteroarylamino, C6 to C30 aryloxy, C3 to C30 heteroaryloxy, C6 to C60 aryl, and C3 to C60 heteroaryl.

[0008] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents, and when there are multiple substituents (at least two), they may be the same or different. Hereinafter, when the same expression is described, it all means the same unless otherwise specified, and the selection range of the substituent is as described above, and will not be described in detail here.

[0009] In the present invention, the halogen includes fluorine, chlorine, bromine, or iodine. Hereinafter, when the same expression is used, it all has the same meaning.

[0010] For the sake of convenience, the present application describes the possible role of each group / characteristic individually, but this does not mean that these groups / characteristics function independently. In fact, the essential reason for obtaining excellent properties lies in the optimized combination of the whole molecule, which is the result of synergistic interactions between individual groups, rather than the effect of a single group.

[0011] In the present invention, unless otherwise specified, the expression of a chemical element includes the concept of an isotope having the same chemical properties. For example, hydrogen (H) has the following isotopes: 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T) and carbon (C) 12 C. 13 Includes C etc.

[0012] In the present invention, the heteroatom of a heteroaryl is an atom or group of atoms selected from N, O, S, P, B, Si or Se, with N, O and S being preferred.

[0013] In the present invention, the expression of a ring structure with a "-" passing through the ring structure means that the linking site is at any position on the ring structure where a bond can be formed.

[0014] In the present invention, the expressions Ca to Cb indicate that the number of carbon atoms in the group is a to b, but unless otherwise specified, this number of carbon atoms generally does not include the number of carbon atoms in the substituent.

[0015] In this specification, the term "independently" means that when there are multiple objects, they may be the same or different.

[0016] In the present invention, the halogen includes fluorine, chlorine, bromine, or iodine.

[0017] In the present invention, the C6 to C30 (e.g., C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) aromatic ring includes a single aromatic ring and a fused aromatic ring, the single aromatic ring includes a benzene ring, a biphenyl ring, or a terphenyl ring, and the fused aromatic ring includes a ring containing at least two aromatic rings and in which the aromatic rings share two adjacent carbon atoms and are fused to each other, such as, but not limited to, a naphthalene ring, an anthracene ring, a phenanthrene ring, an indene ring, a fluorene ring and derivatives thereof (e.g., 9,9-dimethylfluorene ring, benzofluorene ring), a fluoranthene ring, a triphenylene ring, a pyrene ring, a perylene ring, a chrysene ring, or a tetracene ring.

[0018] The C3 to C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) heteroaromatic ring includes a monocyclic heteroaromatic ring or a fused heteroaromatic ring. Examples of the monocyclic heteroaromatic ring include, but are not limited to, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a thiophene ring, and a carbazole ring. The fused heteroaromatic ring refers to a ring structure containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and these two rings are fused to each other by sharing two adjacent atoms. Examples include, but are not limited to, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a benzofuran ring, a benzothiophene ring, an isobenzofuran ring, an isobenzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring and its derivatives (such as an N-phenylcarbazole ring, a benzocarbazole ring, a dibenzocarbazole ring, an indolocarbazole ring, and an azacarbazole ring), an acridine ring, a phenothiazine ring, a phenoxazine ring, and a hydrogenated acridine ring.

[0019] In the present invention, the C1-C20 chain alkyl includes C1-C20 linear alkyl and C1-C20 branched alkyl. For example, it may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18 linear or branched alkyl, but is preferably C1-C16 linear or branched alkyl, and more preferably C1-C10 linear or branched alkyl. Examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, and n-decyl.

[0020] In the present invention, the C2-C10 alkenyl may be any of C2, C3, C4, C5, C6, C7, C8, C9, and C10 alkenyl, which may contain at least one C=C, and examples thereof include, but are not limited to, vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, and pentadienyl.

[0021] Specific examples of the C1 to C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18) alkoxy of the present invention include monovalent groups in which the above-mentioned examples of linear or branched alkyl are linked to O.

[0022] In the present invention, the C3 to C20 cycloalkyl may be any cycloalkyl such as C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18, including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0023] Specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18) alkylsilyl include monovalent groups in which at least one hydrogen atom in —SiH3 is substituted with the above-mentioned linear or branched alkyl. Specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18) alkylamino include monovalent groups in which at least one hydrogen atom in —NH2 is substituted with the above-mentioned linear or branched alkyl.

[0024] Specific examples of the C2 to C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18) heterocycloalkyl of the present invention include monovalent groups in which at least one ring C atom in the above cycloalkyl examples is replaced with a heteroatom (e.g., O, S, N, or P), and examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0025] In the present invention, the C6-C60 aryl may be any of C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, and C58, but is preferably a C6-C30 aryl, including a monocyclic aryl and a fused-ring aryl. The monocyclic aryl refers to a group containing at least one phenyl, and when at least two phenyls are contained, the phenyls are connected to each other by a single bond. Examples include, but are not limited to, phenyl, biphenyl, and terphenyl. The fused ring aryl refers to a group containing at least two aromatic rings, and the aromatic rings are fused to each other by sharing two adjacent carbon atoms, and examples thereof include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylenyl, chrysenyl, anthracenyl, etc. The above-mentioned groups include all possible linking forms.

[0026] In the present invention, the C3 to C60 heteroaryl may be any heteroaryl such as C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58, but is preferably a C3 to C30 heteroaryl, more preferably a C4 to C20 heteroaryl, and includes a monocyclic heteroaryl or a fused ring heteroaryl. The monocyclic heteroaryl refers to a group containing at least one heteroaryl in the molecule, and when the molecule contains one heteroaryl and another group (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and the other group are connected by a single bond. Examples include, but are not limited to, furyl, thienyl, pyrrolyl, pyridyl, etc. The fused ring heteroaryl refers to a group that contains at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the adjacent two atoms shared by both of these rings are fused together, and examples thereof include, but are not limited to, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and hydrogenated acridinyl.The above-listed groups include all possible linking forms.

[0027] Specific examples of the C6 to C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) alkylene of the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned aryl examples. Specific examples of the C3 to C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) heteroarylene include divalent groups obtained by removing one hydrogen atom from the above-mentioned heteroaryl examples.

[0028] Specific examples of the C6 to C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) aryloxy of the present invention include monovalent groups in which the above-mentioned aryl examples are linked to O. Specific examples of the C3 to C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) heteroaryloxy include monovalent groups in which the above-mentioned heteroaryl examples are linked to O.

[0029] The C6 to C60 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58) arylamino of the present invention, preferably a C6 to C30 arylamino, is a monovalent group in which at least one hydrogen atom in —NH2 is substituted with the above-mentioned aryl, and examples thereof include, but are not limited to, phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, and biphenylamino.

[0030] The C3 to C60 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58) heteroarylamino of the present invention, preferably a C3 to C30 heteroarylamino, is a monovalent group in which at least one hydrogen atom in —NH2 is substituted by the above-mentioned heteroaryl, and examples thereof include, but are not limited to, pyridylamino, pyrimidinylamino, and dibenzofuranylamino.

[0031] Furthermore, in Formula I, L1 is selected from R1, R2, R3, R4, R7, R8, R 11 , or R 12Preferably, L1 is linked to any of the R1, R2, R3, and R4 sites.

[0032] Furthermore, in formula I, Ar1 and Ar2 are each independently one selected from substituted or unsubstituted C6 to C30 aryl and substituted or unsubstituted C3 to C30 heteroaryl, and at least one hydrogen atom in Ar1 and Ar2 is replaced by deuterium; Preferably, all hydrogen atoms in said Ar1 and / or Ar2 are replaced by deuterium.

[0033] Furthermore, in formula I, Ar1 and Ar2 are each independently one selected from substituted or unsubstituted phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, indolocarbazolyl, azadibenzothienyl, and azadibenzofuranyl, and at least one hydrogen atom in Ar1 and Ar2 is replaced by deuterium; When each of the above substituted or unsubstituted groups has a substituent, the substituent is one or a combination of at least two selected from deuterium, halogen, C1 to C10 chain alkyl, C3 to C10 cycloalkyl, C1 to C10 alkoxy, C2 to C10 heterocycloalkyl, C6 to C60 aryl, and C3 to C60 heteroaryl; Preferably, all hydrogen atoms in said Ar1 and / or Ar2 are replaced by deuterium.

[0034] Furthermore, in formula I, L1, L2, and L3 are each independently one selected from a single bond, phenylene, naphthylene, anthracenylene, phenanthrenylene, biphenylene, triphenylene, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, spirofluorenylene, benzofluorenylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, carbazolylene, triazinylene, triazolinylene, pyridylene, pyrimidinylene, quinazolinylene, quinoxalinylene, benzimidazolinylene, benzindazolylene, benzocarbazolylene, benzofurocarbazolylene, benzothienocarbazolylene, indolocarbazolylene, azadibenzothienylene, azadibenzofuranylene, phenyleneamino, naphthyleneamino, and biphenyleneamino; Preferably, L2 and L3 are each independently one selected from a single bond, phenylene, naphthylene, phenanthrenylene, biphenylene, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, spirofluorenylene, benzofluorenylene, pyridylene, dibenzofuranylene, dibenzothienylene, and pyrimidinylene, and L1 is a single bond, phenylene, naphthylene, dibenzofuranylene, dibenzothienylene, biphenylene, carbazolylene, phenanthrenylene, triphenylene, and pyridylene, More preferably, L1, L2, and L3 are each independently one selected from a single bond, phenylene, naphthylene, dibenzofuranylene, and dibenzothiophene.

[0035] Furthermore, in formula I, the R1 to R 14are each independently one of hydrogen, deuterium, halogen, methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, indolocarbazolyl, azadibenzothienyl, and azadibenzofuranyl; Preferably, the R1 to R 14 are each independently one of hydrogen, deuterium, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, pyridyl, and carbazolyl, and more preferably, 14 are each independently hydrogen or deuterium.

[0036] Preferably, the organic compound of the present invention has any one of the following structures: JPEG2026504764000003.jpg175170JPEG2026504764000004.jpg48170JPEG2026504764000005.jp g201170JPEG2026504764000006.jpg245170JPEG2026504764000007.jpg213170JPEG20265047640 00008.jpg208170JPEG2026504764000009.jpg229170JPEG2026504764000010.jpg255170JPEG202 6504764000011.jpg227170JPEG2026504764000012.jpg251170JPEG2026504764000013.jpg213170 JPEG2026504764000014.jpg200170JPEG2026504764000015.jpg255170JPEG2026504764000016.j pg255170JPEG2026504764000017.jpg215170JPEG2026504764000018.jpg235170JPEG20265047640 00019.jpg234170JPEG2026504764000020.jpg224170JPEG2026504764000021.jpg245170JPEG202 6504764000022.jpg235170JPEG2026504764000023.jpg231170JPEG2026504764000024.jpg230170

[0037] In the core structure of the compound of the present invention, a specific fused ring structure is designed to be connected to a triazine structure, so that such a compound has excellent electron transport properties and photoelectric properties and a low triplet energy level, making it particularly suitable as a host material for an emitting layer. This reduces the energy level difference between the host and guest, reduces the loss during energy transfer, achieves higher efficiency, and improves the overall characteristics of the device. Furthermore, in the present invention, the triazine substituent is deuterized to further improve the stability of the molecule and extend the service life of the device.

[0038] In this application, for the sake of convenience, the possible role of each group / characteristic is described separately, but this does not mean that these groups / characteristics function independently. In fact, the essential reason for obtaining excellent properties lies in the optimized combination of the whole molecule, which is the result of synergistic interactions between the individual groups, rather than the effect of a single group.

[0039] In a second aspect, the present invention provides the use of a compound according to the first aspect, wherein said compound is used in an organic electronic device.

[0040] Preferably, the organic electronic device includes an organic electroluminescence device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet scanner, or electronic paper.

[0041] Preferably, the compound is used in an organic electroluminescent device. Preferably, the compound is used in a red light organic electroluminescent device.

[0042] Preferably, the compound is used as an emissive layer material in an organic electroluminescent device. Preferably, the compound is used as a host material in an emissive layer in an organic electroluminescent device.

[0043] In a third aspect, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes, the organic layer comprising at least one compound according to the first aspect.

[0044] Preferably, said organic layer comprises at least one compound of the structure described in the first aspect.

[0045] Preferably, the organic layer includes an emitting layer, and the emitting layer includes at least one compound according to the first aspect.

[0046] Preferably, the light-emitting layer contains a host material and a doping material, and the host material contains at least one compound according to the first aspect.

[0047] In a preferred technical solution of the present invention, the compound functions as a host material in the light-emitting layer, and is an electron-type host material with a low triplet energy level, and is particularly suitable as a host material in the red light-emitting layer, which can extend the service life of the organic electroluminescent device.

[0048] Preferably, the host material comprises a combination of a first host material and a second host material, and the first host material comprises at least one compound according to the first aspect.

[0049] Preferably, the second host material is an arylamine compound.

[0050] JPEG2026504764000025.jpg28170 wherein Ar3, Ar4, and Ar5 are each independently any one selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and the substituents are each independently one or a combination of at least two selected from deuterium, halogen, C1-C20 chain alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxy, nitro, cyano, amino, hydroxy, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0051] Preferably, the compound is used in a dual-host device as a first host material, which has excellent electron transport properties, and when combined with a second host material, can effectively adjust and achieve a balance between hole and electron transport, further improving the efficiency and lifetime of the device and enhancing the overall performance of the device.

[0052] Preferably, the mass ratio of the first host material to the second host material is (0.1 to 2):1, for example, 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1, or 1.9:1, and more preferably (0.5 to 1.5):1).

[0053] Preferably, the organic layer further comprises a hole transport region and an electron transport region. Preferably, the hole transport region comprises any one or a combination of at least two of a hole injection layer, a hole transport layer, or an electron blocking layer. Preferably, the electron transport region comprises any one or a combination of at least two of an electron injection layer, an electron transport layer, or a hole blocking layer.

[0054] The present invention also provides an electronic device having a display screen or a display panel, wherein the display screen or the display panel uses the organic electroluminescence device described above. DETAILED DESCRIPTION OF THE INVENTION

[0055] Synthesis Examples The technical solution of the present invention will be further described below by means of specific embodiments. Those skilled in the art will understand that the above examples are merely for aiding in the understanding of the present invention and are not to be considered as particularly limiting the present invention.

[0056] In one particular embodiment, the compounds may be prepared according to the following representative synthetic scheme: JPEG2026504764000026.jpg49170 (where L1, L2, L3, Ar1, Ar2, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , and R 14 has the same limits as those of formula I, and X is a halogen, preferably Cl or Br.

[0057] The preparation method of the compound of formula I of the present invention is not limited to the above synthesis method, and those skilled in the art can generally adjust the preparation method according to actual needs, and compounds having the structure represented by formula I that are synthesized by other methods also fall within the protection scope of the present invention.

[0058] The following synthesis examples of the present invention provide specific synthesis methods for representative compounds as examples, and the solvents and reagents used in the synthesis examples can be purchased from chemical product markets or customized. Mass spectrometry characterization data (MS) of the intermediates and target compounds in the present invention can be obtained through tests using a mass spectrometer.

[0059] In one particular embodiment, the preparation of intermediates used in the synthetic examples below is as follows. Synthesis of intermediate M1: JPEG2026504764000027.jpg93170

[0060] 4-Hydroxy-1-bromonaphthalene (1 mol), compound S1 (1 mol), potassium carbonate (1.2 mol), tetrakis(triphenylphosphine)palladium(0) (0.01 mol), water (300 mL), and dioxane (1500 mL) were added to a reaction flask and heated to 90°C for 6 h. Completion of the reaction was monitored by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated and concentrated to give intermediate M1-A.

[0061] Intermediate M1-A (0.5 mol), palladium acetate (0.025 mol), tricyclohexylphosphine (0.05 mol), and potassium carbonate (0.8 mol) were added to N,N-dimethylacetamide (800 mL), heated to reflux, and reacted for 4 h. Completion of the reaction was monitored by thin-layer chromatography (TLC). The reaction mixture was filtered, and the solvent was distilled under reduced pressure and washed with ethanol to obtain intermediate M1-B.

[0062] Intermediate M1-B (0.4 mol) and triethylamine (0.8 mol) were added to dichloromethane (800 mL) and the mixture was cooled to -5°C. Trifluoromethanesulfonic anhydride (0.7 mol) was then added dropwise to the mixture. After the addition was completed, the mixture was allowed to react at room temperature for 4 hours. The completion of the reaction was monitored by thin layer chromatography (TLC). Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain intermediate M1-C.

[0063] Intermediate M1-C (0.3 mol), bis(pinacolato)diboron (0.36 mol), potassium acetate (0.4 mol), 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (0.003 mol), and dioxane (800 mL) were added to a reaction flask and heated to 100°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC). The reaction solution was directly filtered and concentrated to give oil M1, which was purified by column chromatography to give white intermediate M1.

[0064] Synthesis of intermediates M2, M3, and M4: Intermediates M2, M3, and M4 below were obtained in the same manner as in the synthesis of intermediate M1, except that 4-hydroxy-1-bromonaphthalene was replaced with equivalent amounts of 5-bromo-1-naphthol, 5-bromo-2-naphthol, and 8-bromo-2-naphthol, respectively. [ka] Synthesis of intermediate M5: JPEG2026504764000029.jpg43170JPEG2026504764000030.jpg49170

[0065] 2-Chloro-1-bromonaphthalene (1 mol), compound S2 (1 mol), potassium carbonate (1.2 mol), tetrakis(triphenylphosphine)palladium(0) (0.01 mol), water (300 mL), and dioxane (1500 mL) were added to a reaction flask and heated to 90°C for 6 h. The reaction was monitored by thin layer chromatography (TLC) for completion, and the mixture was extracted with water and dichloromethane. The organic phase was separated and concentrated to give intermediate M5-A.

[0066] Intermediate M5-A (0.5 mol), palladium acetate (0.025 mol), tricyclohexylphosphine (0.05 mol), and potassium carbonate (0.8 mol) were added to N,N-dimethylacetamide (800 mL), heated to reflux, and reacted for 4 h. Completion of the reaction was monitored by thin-layer chromatography (TLC). The reaction solution was filtered, and the solvent was distilled under reduced pressure and washed with ethanol to obtain intermediate M5-B.

[0067] Intermediate M5-B (0.4 mol) and triethylamine (0.8 mol) were added to dichloromethane (800 mL) and the mixture was cooled to -5°C. Trifluoromethanesulfonic anhydride (0.7 mol) was then added dropwise to the mixture. After the addition was completed, the mixture was allowed to react at room temperature for 4 hours. The completion of the reaction was monitored by thin layer chromatography (TLC). Water and dichloromethane were added for extraction, and the organic phase was separated and concentrated to obtain intermediate M5-C.

[0068] Intermediate M5-C (0.3 mol), bis(pinacolato)diboron (0.36 mol), potassium acetate (0.4 mol), 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (0.003 mol), and dioxane (800 mL) were added to a reaction flask and heated to 100°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC). The reaction solution was directly filtered and concentrated to give oil M1, which was purified by column chromatography to give white intermediate M5.

[0069] Synthesis of intermediate M6: M6 was synthesized in the same manner as M5, except that S2 was changed to an equivalent amount of 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-ol, to obtain intermediate M6. JPEG2026504764000031.jpg43170Synthesis of partially deuterated triazine substituents: JPEG2026504764000032.jpg59170

[0070] Phenylboronic acid-D5 (0.1 mol), 2-(4-biphenyl)-4,6-dichloro-1,3,5-triazine (0.1 mol), potassium carbonate (0.12 mol), tetrakis(triphenylphosphine)palladium(0) (0.001 mol), water (30 mL), and dioxane (300 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated and concentrated to give intermediate N1. JPEG2026504764000033.jpg63170

[0071] 3-Chlorophenylboronic acid (0.08 mol), Intermediate N1 (0.08 mol), potassium carbonate (0.1 mol), tetrakis(triphenylphosphine)palladium(0) (0.0008 mol), water (25 mL), and dioxane (250 mL) were added to a reaction flask and heated to 100°C for 8 h. Completion of the reaction was monitored by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated and concentrated to give Intermediate N2. JPEG2026504764000034.jpg53170

[0072] Phenylboronic acid-D5 (0.08 mol), 2,4-dichloro-6-phenyl-1,3,5-triazine (0.08 mol), potassium carbonate (0.1 mol), tetrakis(triphenylphosphine)palladium(0) (0.0008 mol), water (25 mL), and dioxane (250 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated and concentrated to give intermediate N3. JPEG2026504764000035.jpg43170

[0073] Phenylboronic acid-D5 (0.08 mol), 2,4-dichloro-6-(dibenzofuran-1-yl)-1,3,5-triazine (0.08 mol), potassium carbonate (0.1 mol), tetrakis(triphenylphosphine)palladium(0) (0.0008 mol), water (25 mL), and dioxane (250 mL) were added to a reaction flask and heated to 90°C for 5 h. Completion of the reaction was monitored by thin layer chromatography (TLC). The mixture was extracted with water and dichloromethane, and the organic phase was separated and concentrated to give intermediate N4. JPEG2026504764000036.jpg50170

[0074] Dibenzofuran-1-boronic acid-D7 (0.08 mol), 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (0.08 mol), potassium carbonate (0.1 mol), tetrakis(triphenylphosphine)palladium(0) (0.0008 mol), water (25 mL), and dioxane (250 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated and concentrated to give intermediate N5. JPEG2026504764000037.jpg50170

[0075] Phenylboronic acid-D5 (0.08 mol), 2,4-dichloro-6-(dibenzofuran-4-yl)-1,3,5-triazine (0.08 mol), potassium carbonate (0.1 mol), tetrakis(triphenylphosphine)palladium(0) (0.0008 mol), water (25 mL), and dioxane (250 mL) were added to a reaction flask and heated to 90°C for 5 h. Completion of the reaction was monitored by thin layer chromatography (TLC). The mixture was extracted with water and dichloromethane, and the organic phase was separated and concentrated to give intermediate N6. JPEG2026504764000038.jpg49170

[0076] Phenylboronic acid-D5 (0.2 mol), 2,4-dichloro-6-(3-chlorophenyl)-1,3,5-triazine (0.08 mol), potassium carbonate (0.1 mol), tetrakis(triphenylphosphine)palladium(0) (0.0008 mol), water (25 mL), and dioxane (250 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated and concentrated to give intermediate N7.

[0077] Synthesis Example 1 For the synthesis of compound A4, the synthesis scheme is as follows: JPEG2026504764000039.jpg54170

[0078] Intermediate M1 (0.02 mol), Intermediate N1 (0.02 mol), potassium carbonate (0.024 mol), tetrakis(triphenylphosphine)palladium(0) (0.0002 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100°C for 6 h. Completion of the reaction was monitored by thin layer chromatography (TLC). Water and dichloromethane were added for extraction, and the organic phase was separated, concentrated, and purified by column chromatography to give the desired product A4 (MS, 590.28).

[0079] Synthesis Example 2 For the synthesis of compound A34, the synthetic scheme is as follows: JPEG2026504764000040.jpg53170

[0080] Compound A34 (MS, 666.29) was obtained in the same manner as in Synthesis Example 1, except that intermediate N1 was replaced with an equivalent amount of N2.

[0081] Synthesis Example 3 For the synthesis of compound A37, the synthetic scheme is as follows: JPEG2026504764000041.jpg46170

[0082] Intermediate N3 (0.05 mol), 1-chloro-3-naphthylboronic acid (0.05 mol), potassium carbonate (0.06 mol), tetrakis(triphenylphosphine)palladium(0) (0.0005 mol), water (50 mL), and dioxane (300 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product A37-1.

[0083] Intermediate M1 (0.02 mol), compound A37-1 (0.02 mol), potassium phosphate (0.024 mol), tris(dibenzylideneacetone)dipalladium(0) (0.0002 mol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 8 h. When the reaction was complete, water and dichloromethane were added for extraction. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product A37 (MS, 640.28).

[0084] Synthesis Example 4 For the synthesis of compound A50, the synthetic scheme is as follows: JPEG2026504764000042.jpg55170

[0085] Compound A50 (MS, 680.27) was obtained in the same synthetic method as in Synthesis Example 3, except that 1-chloro-3-naphthylboronic acid was replaced with an equivalent amount of A50-S.

[0086] Synthesis Example 5 For the synthesis of compound B19, the synthetic scheme is as follows: JPEG2026504764000043.jpg49170

[0087] Intermediate M2 (0.02 mol), Intermediate N6 (0.02 mol), potassium carbonate (0.024 mol), tetrakis(triphenylphosphine)palladium(0) (0.0002 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 6 h. Completion of the reaction was monitored by thin layer chromatography (TLC). Water and dichloromethane were added for extraction, and the organic phase was separated, concentrated, and purified by column chromatography to give the desired product B19 (MS, 604.25).

[0088] Synthesis Example 6 For the synthesis of compound B32, the synthetic scheme is as follows: JPEG2026504764000044.jpg57170

[0089] Intermediate M2 (0.02 mol), Intermediate N7 (0.02 mol), potassium phosphate (0.024 mol), tris(dibenzylideneacetone)dipalladium(0) (0.0002 mol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 8 h. When the reaction was complete, water and dichloromethane were added for extraction. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product B32 (MS, 595.29).

[0090] Synthesis Example 7 For the synthesis of compound B41, the synthetic scheme is as follows: JPEG2026504764000045.jpg51170

[0091] 1-Bromo-6-chloronaphthalene (0.1 mol), bis(pinacolato)diboron (0.12 mol), potassium acetate (0.15 mol), 1,1-bis(diphenylphosphino)ferrocenepalladium dichloride (0.001 mol), and dioxane (300 mL) were added to a reaction flask and heated to 100°C under nitrogen protection for 6 hours. The reaction was monitored for completion by thin-layer chromatography (TLC), and the reaction solution was directly filtered, concentrated, and the solvent was removed. The resulting white solid B41-S1 was then purified by column chromatography.

[0092] Intermediate N3 (0.05 mol), compound B41-S1 (0.05 mol), potassium carbonate (0.06 mol), tetrakis(triphenylphosphine)palladium(0) (0.0005 mol), water (50 mL), and dioxane (300 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product B41-S2.

[0093] Intermediate M2 (0.02 mol), compound B41-S2 (0.02 mol), potassium phosphate (0.024 mol), tris(dibenzylideneacetone)dipalladium(0) (0.0002 mol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 8 h. When the reaction was complete, water and dichloromethane were added for extraction. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product B41 (MS, 640.28).

[0094] Synthesis Example 8 For the synthesis of compound C18, the synthetic scheme is as follows: JPEG2026504764000046.jpg57170

[0095] Intermediate M3 (0.02 mol), Intermediate N4 (0.02 mol), potassium carbonate (0.025 mol), tetrakis(triphenylphosphine)palladium(0) (0.0002 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 6 h. Completion of the reaction was monitored by thin layer chromatography (TLC). The mixture was extracted with water and dichloromethane, and the organic phase was separated, concentrated, and purified by column chromatography to give the desired product C18 (MS, 604.25).

[0096] Synthesis Example 9 For the synthesis of compound C49, the synthetic scheme is as follows: JPEG2026504764000047.jpg61170

[0097] Intermediate N3 (0.05 mol), compound C49-S (0.05 mol), potassium carbonate (0.025 mol), tetrakis(triphenylphosphine)palladium(0) (0.0002 mol), water (50 mL), and dioxane (300 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC), and the mixture was extracted with water and dichloromethane. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product C49-1.

[0098] Intermediate M3 (0.02 mol), compound C49-1 (0.02 mol), potassium phosphate (0.024 mol), tris(dibenzylideneacetone)dipalladium(0) (0.0002 mol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 8 h. When the reaction was complete, water and dichloromethane were added for extraction. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product C49 (MS, 680.27).

[0099] Synthesis Example 10 For the synthesis of compound D18, the synthetic scheme is as follows: JPEG2026504764000048.jpg61170

[0100] Intermediate M4 (0.02 mol), Intermediate N4 (0.02 mol), potassium carbonate (0.025 mol), tetrakis(triphenylphosphine)palladium(0) (0.0002 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 6 h. Completion of the reaction was monitored by thin layer chromatography (TLC). Water and dichloromethane were added for extraction, and the organic phase was separated, concentrated, and purified by column chromatography to give the desired product C18 (MS, 604.25).

[0101] Synthesis Example 11 For the synthesis of compound D24, the synthetic scheme is as follows: JPEG2026504764000049.jpg65170

[0102] Compound D24 (MS, 656.27) was obtained in the same manner as in Synthesis Example 10, except that N4 was replaced with an equivalent amount of N5.

[0103] Synthesis Example 12 For the synthesis of compound D34, the synthetic scheme is as follows: JPEG2026504764000050.jpg52170

[0104] Intermediate N4 (0.05 mol), 3-chlorophenylboronic acid (0.05 mol), potassium carbonate (0.06 mol), tetrakis(triphenylphosphine)palladium(0) (0.0005 mol), water (50 mL), and dioxane (300 mL) were added to a reaction flask and heated to 90°C for 5 h. The reaction was monitored for completion by thin layer chromatography (TLC), and water and dichloromethane were added for extraction. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product D34-1.

[0105] Intermediate M4 (0.02 mol), compound D34-1 (0.02 mol), potassium phosphate (0.024 mol), tris(dibenzylideneacetone)dipalladium(0) (0.0002 mol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 8 h. When the reaction was complete, water and dichloromethane were added for extraction. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product D34 (MS, 680.28).

[0106] Synthesis Example 13 For the synthesis of compound E6, the synthetic scheme is as follows: JPEG2026504764000051.jpg68170

[0107] Intermediate M6 (0.02 mol), intermediate N2 (0.02 mol), potassium phosphate (0.024 mol), tris(dibenzylideneacetone)dipalladium(0) (0.0002 mol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 8 h. When the reaction was complete, water and dichloromethane were added for extraction. The organic phase was separated, concentrated, and purified by column chromatography to give the desired product E6 (MS, 666.29).

[0108] Synthesis Example 14 For the synthesis of compound E15, the synthesis scheme is as follows: JPEG2026504764000052.jpg62170

[0109] Intermediate M5 (0.02 mol), compound A37-1 (0.02 mol), potassium phosphate (0.024 mol), tris(dibenzylideneacetone)dipalladium(0) (0.0002 mol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.0004 mol), water (20 mL), and dioxane (200 mL) were added to a reaction flask and heated to 100 °C for 8 h. Upon completion of the reaction, water and dichloromethane were added for extraction. The organic phase was separated, concentrated, and purified by column chromatography to obtain the desired product E15 (MS, 640.28).

[0110] The present invention exemplifies specific synthetic methods for the above-mentioned compounds, and other compounds for which specific synthetic methods are not specified can be prepared by similar methods and can be obtained by simply replacing the raw materials, so they will not be described in detail here, or can be prepared by those skilled in the art using other methods in the prior art.

[0111] Device Example Embodiment An OLED includes a first electrode, a second electrode, and an organic material layer located between the electrodes. The organic material layer may be further divided into multiple regions. For example, the organic material layer may include a hole transport region, an emissive layer, and an electron transport region.

[0112] In certain embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials that have good mechanical strength, thermal stability, waterproofness, and transparency. Additionally, thin film transistors (TFTs) can be provided on the substrate for displays.

[0113] The first electrode can be formed by sputtering or depositing a first electrode material onto a substrate. When the first electrode is used as an anode, transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO), zinc oxide (ZnO), and any combination thereof can be used. When the first electrode is used as a cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof can be used.

[0114] The organic layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic layer may be an organic small molecule, an organic macromolecule or polymer, or a combination thereof.

[0115] The hole transport region is located between the anode and the light-emitting layer. The hole transport region may be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one type of compound and a single-layer hole transport layer containing multiple types of compounds. The hole transport region may also have a multi-layer structure including at least one layer selected from the group consisting of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL). The HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0116] The material of the hole transport region may also be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers such as polyphenylene vinylene, polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or polymers containing conductive dopants, arylamine derivatives such as the compounds shown below as HT-1 to HT-51, or any combination thereof. JPEG2026504764000053.jpg41170JPEG2026504764000054.jpg221170JPEG2026504764000055.jpg231170JPEG2026504764000056.jpg126170

[0117] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be made of a single compound material or a combination of multiple compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds HI-1 to HI-3 described below, or may employ one or more of the compounds HT-1 to HT-51 doped with one or more of the compounds HI-1 to HI-3 described below. JPEG2026504764000057.jpg45170

[0118] The light-emitting layer may contain a light-emitting dye (i.e., a dopant) capable of emitting light of different wavelength spectrums, or may also contain a host material. The light-emitting layer may be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. Multiple monochromatic light-emitting layers of different colors may be arranged on a plane according to a pixel pattern or stacked to form a colored light-emitting layer. When stacking light-emitting layers of different colors, the light-emitting layers may be spaced apart from each other or connected to each other. Alternatively, the light-emitting layer may be a single color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.

[0119] Depending on the technology, the light-emitting layer materials can be fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescent luminescent materials, etc. OLED devices can use a single light-emitting technology or a combination of different light-emitting technologies. These different light-emitting materials, classified by technology, can emit light of the same color or different colors.

[0120] In one embodiment of the present invention, the light-emitting layer employs phosphorescent electroluminescence technology, and the host material of the light-emitting layer comprises a combination of a first host material and a second host material, wherein the first host material comprises at least one of the compounds of formula I or the compounds according to the present invention (A1-E16).

[0121] JPEG2026504764000058.jpg36170JPEG2026504764000059.jpg148170JPEG2026504764000060.jpg55170JPEG2026504764000061.jpg190170

[0122] In one embodiment of the present invention, the light-emitting layer employs phosphorescent electroluminescence technology, and the phosphorescent dopant of the light-emitting layer may be one or a combination of dopants selected from the following RPD-1 to RPD-28, but is not limited thereto. JPEG2026504764000062.jpg237170

[0123] In one embodiment of the present invention, an electron-blocking layer (EBL) is located between the hole-transporting layer and the light-emitting layer. The electron-blocking layer may employ, but is not limited to, one or more of the compounds HT-1 to HT-51 described above, one or more of the compounds PH-47 to PH-77 described above, one or more of the compounds P1 to P648 of the present invention, one or more of the compounds HT-1 to HT-51, one or more of the compounds PH-47 to PH-77, and a mixture of one or more compounds of the materials of the present invention.

[0124] The OLED organic material layer may further include an electron transport region between the light-emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multi-layer structure including at least one layer selected from the group consisting of an electron injection layer (EIL), an electron transport layer (ETL), and a hole-blocking layer (HBL).

[0125] In one embodiment of the present invention, the electron transport layer material may be one or a combination of materials selected from the following ET-1 to ET-73, but is not limited thereto. JPEG2026504764000063.jpg168170JPEG2026504764000064.jpg239170JPEG2026504764000065.jpg250170JPEG2026504764000066.jpg98170

[0126] In one embodiment of the present invention, a hole-blocking layer (HBL) is located between the electron-transporting layer and the light-emitting layer. The hole-blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 and one or more of the compounds PH-1 to PH-46, or may employ, but is not limited to, a mixture of one or more of the compounds ET-1 to ET-73 and one or more of the compounds PH-1 to PH-46.

[0127] The device may further include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material may include, but is not limited to, one or a combination of materials listed below.

[0128] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb In this example, the manufacturing process of the organic electroluminescent device is as follows. Example 1 The organic electroluminescent device of this example includes an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, an electron transport layer, an electron injection layer, and a cathode (Al), which are arranged in this order. The specific manufacturing method is as follows: (1) A glass plate coated with an ITO transparent conductive layer was ultrasonically treated with a commercially available cleaning agent, then rinsed with deionized water, and the oil was removed by ultrasonication in an acetone / ethanol mixed solvent. The plate was baked in a clean environment until the water was completely removed, and then cleaned with ultraviolet light and ozone. The surface was then irradiated with a low-energy positive ion beam. (2) Place the glass substrate with the ITO anode in a vacuum chamber and measure 1×10 -5 The vacuum was drawn to less than Pa, and a mixture of compounds HT-29:HI-1 (97 / 3, w / w) was vacuum-deposited onto the anode layer as a hole-injection layer at a deposition rate of 0.1 nm / s and a deposited film thickness of 10 nm. (3) As a hole transport layer, compound HT-29 was vacuum-deposited on the hole injection layer at a deposition rate of 0.1 nm / s to a film thickness of 60 nm. (4) As an electron blocking layer, compound HT-37 was vacuum-deposited on the hole transport layer at a deposition rate of 0.1 nm / s to a thickness of 60 nm. (5) An emissive layer containing a host material and a doping material (dye, RPD-18) was vacuum-deposited on the electron-blocking layer. The mass ratio (w / w) of the host material to the doping material was 100:3. The host material was a mixture of a first host material (compound A4 according to the present invention) and a second host material (compound H17) (the mass ratio of A4 to H17 was 1:1). The deposition rate was 0.1 nm / s, and the total deposited film thickness was 40 nm. (6) As a hole-blocking layer, compound ET-17 was vacuum-deposited on the light-emitting layer at a deposition rate of 0.1 nm / s to a thickness of 5 nm. (7) As an electron transport layer, a mixture of compounds ET-66 and ET-57 (50 / 50, w / w) was vacuum-deposited on the hole-blocking layer at a deposition rate of 0.1 nm / s to a total deposited film thickness of 25 nm. (8) As an electron injection layer, the compound LiF was vacuum-deposited on the electron transport layer at a deposition rate of 0.1 nm / s to a thickness of 1 nm. (9) A 150 nm thick aluminum metal layer was vacuum-deposited on the electron injection layer at a deposition rate of 1 nm / s to form a cathode, thereby obtaining the organic electroluminescence device.

[0129] Examples 2 to 14, Comparative Examples 1 to 5 In these exemplary organic electroluminescent devices, compared with Example 1, the host material of the emitting layer was changed to the material shown in the table, and the mass ratio of the first host material to the second host material was 1:1.

[0130] The structures of the host materials in the above examples and comparative examples are as follows: JPEG2026504764000067.jpg103170

[0131] Characterization of organic electroluminescent devices: The lifetime of the organic electroluminescent device was measured using a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent device was 10,000 cd / m 2to 9,700 cd / m 2 The time it took for the temperature to drop to 1000 V was measured and taken as the T97 lifetime of the device.

[0132] In Table 1, the life test value of Comparative Example 1 is recorded as 1, and all values ​​of other Examples are ratios to the test value of Comparative Example 1. In Table 2, the efficiency test value of Comparative Example 3 is recorded as 1, and all values ​​of other Examples are ratios to the test value of Comparative Example 3. The test results are shown in the table below. [Table 1]

[0133] [Table 2]

[0134] The data in the above table show that the compounds of the present invention are suitable for use in organic electroluminescent devices as red-light host materials in the emission layer and can effectively improve the device lifetime. A comparison of Ref-1 with A34 of the present invention reveals that the atomic masses of deuterium and hydrogen are significantly different, the bond formed by carbon and deuterium vibrates at a lower frequency, its zero-point fundamental energy is lower than the bond energy of the corresponding carbon-hydrogen bond, and the activation energies of their transition states are similar. Therefore, more energy is required to break the carbon-deuterium bond than to break the carbon-hydrogen bond. Therefore, the deuterated compounds of the present invention are more stable in devices and have a longer lifetime. Although Ref-2 is also a deuterated compound, its shorter lifetime is due to a significant difference in structure from the present invention, with the furan hetero-fused ring structure itself being less stable than the benzochrysene aryl aromatic fused ring of the present invention. Furthermore, the difference in their transport ability leads to a slightly worse carrier balance in the host emission layer, resulting in a shorter lifetime than the present invention or a shorter lifetime than the non-deuterated compounds of the same type as the present invention.

[0135] From the data analysis in Table 2, it can be seen that Comparative Examples 3 and 4 have similar structures to those of the present invention and also contain deuterium. However, their efficiency is lower than that of the present invention because their structural conjugation is lower than that of the present invention, resulting in a higher triplet energy level. As a result, the loss of energy transfer between the host and guest is greater, resulting in lower efficiency. Judging from Comparative Example 5, the triplet energy level of the material of the present invention is near 540 nm, which is within the optimal energy level range. Meanwhile, the material of Comparative Example 5 has a larger conjugation structure than the material of the present invention, which inevitably leads to a further decrease in the triplet energy level. Part of the energy is transferred back from the guest to the host, resulting in a significant decrease in efficiency.

[0136] The applicant has described the compound of the present invention and its use, and the organic electroluminescent device through the above examples, but the present invention is not limited to the above examples, that is, it does not mean that the present invention must be implemented depending on the above examples. Any improvements to the present invention, equivalent replacement of each raw material of the product of the present invention, addition of auxiliary components, selection of specific methods, etc. are all within the protection scope and disclosure scope of the present invention, it is obvious to those skilled in the art.

[0137] Although the present invention has been described with reference to the embodiments, it should be understood that the present invention is not limited to the above embodiments, and that various modifications and improvements can be made by those skilled in the art based on the concept of the present invention, and that the scope of the present invention is generally defined by the appended claims.

Claims

1. An organic compound having a structure represented by formula I: (In Formula I, Ar １ , Ar ２ are each independently one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl; Ar １ , Ar ２ wherein at least one hydrogen atom is replaced by a deuterium atom, L １ , L ２ , and L ３ are each independently one of a single bond, a substituted or unsubstituted C6 to C30 alkylene, and a substituted or unsubstituted C3 to C30 heteroarylene; R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ , R １２ , R １３ , and R １４ are each independently one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1 to C10 linear alkyl, substituted or unsubstituted C2 to C10 alkenyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl; Ar １ , Ar ２ , L １ , L ２ , L ３ , and R １ ~R １４ The substituents in the above substitutions are each independently one or a combination of at least two selected from deuterium, halogen, C1 to C20 chain alkyl, C2 to C10 alkenyl, C3 to C20 cycloalkyl, C2 to C20 heterocycloalkyl, C1 to C10 alkoxy, carboxy, nitro, cyano, amino, hydroxy, mercapto, C1 to C20 alkylsilyl, C1 to C20 alkylamino, C6 to C30 arylamino, C3 to C30 heteroarylamino, C6 to C30 aryloxy, C3 to C30 heteroaryloxy, C6 to C60 aryl, and C3 to C60 heteroaryl.

2. In Formula I, L １ is R １ , R ２ , R ３ , R ４ , R ７ , R ８ , R １１ , or R １２ and preferably L １ is R １ , R ２ , R ３ , and R ４ 2. The organic compound of claim 1, wherein the compound is linked to any of the following moieties:

3. The Ar １ , Ar ２ are each independently one selected from substituted or unsubstituted C6 to C30 aryl and substituted or unsubstituted C3 to C30 heteroaryl, and Ar １ , Ar ２ At least one hydrogen atom on the Ar group is replaced by a deuterium atom, and preferably, the Ar group １ and / or Ar ２ 2. The organic compound according to claim 1, wherein all hydrogen atoms in

4. The Ar １ , Ar ２ are each independently one selected from substituted or unsubstituted phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, indolocarbazolyl, azadibenzothienyl, and azadibenzofuranyl; Ar １ , Ar ２ wherein at least one hydrogen atom in When each of the above substituted or unsubstituted groups has a substituent, the substituent is one or a combination of at least two selected from deuterium, halogen, C1 to C10 chain alkyl, C3 to C10 cycloalkyl, C1 to C10 alkoxy, C2 to C10 heterocycloalkyl, C6 to C60 aryl, and C3 to C60 heteroaryl; Preferably, the Ar １ and / or Ar ２ 2. The organic compound according to claim 1, wherein all hydrogen atoms in

5. L １ , L ２ , and L ３ each independently represents one selected from a single bond, phenylene, naphthylene, anthracenylene, phenanthrenylene, biphenylene, triphenylene, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, spirofluorenylene, benzofluorenylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, carbazolylene, triazinylene, triazolinylene, pyridylene, pyrimidinylene, quinazolinylene, quinoxalinylene, benzimidazolinylene, benzindazolylene, benzocarbazolylene, benzofurocarbazolylene, benzothienocarbazolylene, indolocarbazolylene, azadibenzothienylene, azadibenzofuranylene, phenyleneamino, naphthyleneamino, and biphenyleneamino; Preferably, the L ２ and L ３ are each independently one selected from a single bond, phenylene, naphthylene, phenanthrenylene, biphenylene, 9,9-dimethylfluorenylene, 9,9-diphenylfluorenylene, spirofluorenylene, benzofluorenylene, pyridylene, dibenzofuranylene, dibenzothienylene, and pyrimidinylene, and １ is one selected from a single bond, phenylene, naphthylene, dibenzofuranylene, dibenzothienylene, biphenylene, carbazolylene, phenanthrenylene, triphenylene, and pyridylene, More preferably, the L １ , L ２ and L ３ and each independently represent one selected from the group consisting of a single bond, phenylene, naphthylene, dibenzofuranylene, and dibenzothiophene.

6. The R １ ~R １４ are each independently one of hydrogen, deuterium, halogen, methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, benzofluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, triazinyl, triazolyl, pyridyl, pyrimidinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, benzindazolyl, benzocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, indolocarbazolyl, azadibenzothienyl, and azadibenzofuranyl; Preferably, the R １ ~R １４ are each independently one of hydrogen, deuterium, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, pyridyl, and carbazolyl; More preferably, the R １ ~R １４ and each independently represent hydrogen or deuterium.

7. 2. The organic compound according to claim 1, which is selected from the following compounds:

8. Use of the organic compound according to any one of claims 1 to 7, The use is as a functional material in an organic electronic device, and the organic electronic device includes an organic electroluminescence device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information label, an electronic artificial skin sheet, a sheet scanner, or electronic paper; Preferably, the use of the organic compound is as a light-emitting layer material in an organic electroluminescent device.

9. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound according to any one of claims 1 to 7.

10. the light-emitting functional layer includes an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 7; Preferably, the light-emitting layer comprises a first host material and a second host material, the first host material contains the organic compound according to any one of claims 1 to 7, the second host material is an arylamine-based compound represented by the following formula, and a mass ratio of the first host material to the second host material is (0.1 to 2):1, more preferably (0.5 to 1.5):

1. (wherein, the Ar ３ , Ar ４ , and Ar ５ are each independently one type selected from substituted or unsubstituted C6 to C60 aryl and substituted or unsubstituted C3 to C60 heteroaryl, and the substituents of the substitution are each independently one type or a combination of at least two types selected from deuterium, halogen, C1 to C20 chain alkyl, C2 to C10 alkenyl, C3 to C20 cycloalkyl, C2 to C20 heterocycloalkyl, C1 to C10 alkoxy, carboxy, nitro, cyano, amino, hydroxy, mercapto, C1 to C20 alkylsilyl, C1 to C20 alkylamino, C6 to C30 arylamino, C3 to C30 heteroarylamino, C6 to C30 aryloxy, C3 to C30 heteroaryloxy, C6 to C60 aryl, and C3 to C60 heteroaryl.

11. 10. An electronic device having a display screen or a display panel, wherein the display screen or the display panel uses the organic electroluminescence device according to claim 9.

Images