Blue light host material and application thereof

Abstract

The invention provides a blue light host material and application thereof. The blue light host material has a structure as shown in a formula I. The blue light host material has high stability, and can improve the performance of the device and overcome the defects in the prior art when being applied to the organic electroluminescent device.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials, specifically to a blue light host material and its application in organic electroluminescent devices. Background Technology

[0002] Organic light-emitting diode (OLED) devices typically consist of a cathode, an anode, and an organic light-emitting layer located between the cathode and anode. When an OLED is powered, holes from the anode and electrons from the cathode are transported to the organic light-emitting layer, where they recombine and emit light. Compared to red and green light-emitting devices, the performance of blue light-emitting devices is a significant challenge and focus in OLED research, especially since the lifetime of blue light-emitting devices differs considerably from that of red and green light-emitting devices.

[0003] In the prior art, compounds based on 9,10-disubstituted anthracene are a widely used class of host materials for the emitting layer of blue light-emitting devices. Due to their large planar conjugated structure, they possess advantages such as high fluorescence quantum efficiency, strong carrier mobility and charge injection capability, and high thermal stability. However, it is precisely because of this large planar configuration that strong π-π stacking easily forms between molecules, reducing their luminous efficiency and causing a redshift in emission wavelength, thus limiting their application in blue light-emitting devices.

[0004] Therefore, designing and synthesizing novel anthracene-based materials with superior performance is a problem that needs to be solved in this field. Summary of the Invention

[0005] The purpose of this invention is to provide a blue light host material and its application. This blue light host material has high stability, and its application in organic electroluminescent devices can improve the performance of the devices and overcome the defects of the prior art.

[0006] To achieve the above objectives, the present invention adopts the following technical solution:

[0007] In a first aspect, the present invention provides a blue light host material having a structure as shown in Formula I:

[0008]

[0009] Ar is selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C5-C30 heteroaryl groups;

[0010] L1 and L2 are each independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C5-C30 heteroarylene;

[0011] a is any integer from 0 to 8; b is any integer from 0 to 3; c is any integer from 0 to 4.

[0012] R1, R2, and R3 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 arylthio, and substituted or unsubstituted C3-C30 heteroarylthio.

[0013] The substituents described in Ar, L1, L2, R1, R2, and R3 are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, and C3-C30 heteroarylthio.

[0014] In this invention, when L1 is selected as a single bond, it means that Ar and anthracene are directly connected by a single bond. Similarly, when L2 is selected as a single bond, it means that the anthracene is directly connected to the phenyl group containing R2 by a single bond.

[0015] In this invention, 'a' represents the number of substituents R1, and 'a' can be selected from 0, 1, 2, 3, 4, 5, 6, 7, 8. When 'a' is greater than or equal to 2, multiple (e.g., 2, 3, 4, 5, 6, 7, 8) R1s are the same or different groups.

[0016] In this invention, b represents the number of substituents R2, and b can be selected from 0, 1, 2, or 3; when b is greater than or equal to 2, multiple (e.g., 2 or 3) R2s are the same or different groups.

[0017] In this invention, c represents the number of substituents R3, and c can be 0, 1, 2, 3 or 4; when c is greater than or equal to 2, multiple (e.g. 2, 3 or 4) R3s are the same or different groups.

[0018] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents (at least two), they can be the same or different substituents. The same expression used below has the same meaning.

[0019] It should be noted that, for ease of explanation, the possible effects of each group / feature have been described separately in this invention, but this does not mean that these groups / features act in isolation. In fact, the essential reason for obtaining good performance is the optimized combination of the entire molecular structure, the result of the synergistic effect between various groups, rather than the effect of a single group / feature.

[0020] The following are preferred embodiments of the present invention, but are not intended to limit the embodiments provided by the present invention. The objectives and beneficial effects of the present invention can be better achieved and realized through the following preferred embodiments.

[0021] As a preferred embodiment, the blue light host material has a structure as shown in any one of Formula II-1, Formula II-2, Formula II-3, and Formula II-4:

[0022]

[0023] The definitions of Ar, L1, L2, R1, R2, R3, a, b, and c are the same as those in Equation I.

[0024] Preferably, the blue light host material has a structure as shown in Formula II-3.

[0025] As a preferred embodiment, Ar is selected from any one of substituted or unsubstituted C6-C25 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, etc.) aryl groups and substituted or unsubstituted C10-C25 (e.g., C10, C12, C14, C15, C16, C18, C20, C22, C24, etc.) heteroaryl groups.

[0026] Optionally, the substituents in Ar are each independently selected from deuterium, halogens (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C25 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, etc.) aryl, and C3-C25 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, etc.) heteroaryl, or a combination of at least two of these.

[0027] Preferably, the Ar is selected from any of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, binaphthyl, anthracene, phenanthryl, fluorenyl, spirodifluorenyl, dibenzofuranyl, benzonaphthuryl, dibenzothiophenyl, benzonaphthiophenyl, N-phenylcarbazoyl, carbazoyl.

[0028] Optionally, the substituents in Ar are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, and carbazoleyl.

[0029] Preferably, the Ar is selected from any of the following groups, whether deuterated or unsubstituted, where * indicates the linkage site of the group:

[0030]

[0031] In this invention, the number of deuterium atoms in the deuterated group is selected from 1 to the maximum permissible number of deuterations. For example, the number of deuterium atoms in a deuterated phenyl group can be 1, 2, 3, 4, or 5; similarly, the number of deuterium atoms in a deuterated biphenyl group can be 1, 2, 3, 4, 5, 6, 7, 8, or 9. The same expressions used below have the same meaning. Unless otherwise specified, they will not be repeated.

[0032] In some embodiments, the Ar is selected from any of the following groups, where * indicates the linkage site of the group:

[0033]

[0034]

[0035] In some embodiments, the Ar is selected from any of the following groups, where * indicates the linkage site of the group:

[0036]

[0037] As a preferred embodiment, L1 and L2 are each independently selected from any one of single-bonded, substituted or unsubstituted C6-C25 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, etc.) arylene, or substituted or unsubstituted C10-C25 (e.g., C10, C12, C14, C15, C16, C18, C20, C22, C24, etc.) heteroarylene.

[0038] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, halogens (e.g., F, Cl, Br, I), cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C25 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, etc.) aryl, and C3-C25 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, C24, etc.) heteroaryl, or a combination of at least two of these.

[0039] Preferably, L1 and L2 are each independently selected from any of the following groups: single bond, deuterated, or unsubstituted, where * indicates the linkage site of the group:

[0040]

[0041] In some embodiments, L1 and L2 are each independently selected from single bonds or any of the following groups, where * indicates the linking site of the group:

[0042]

[0043]

[0044] In some embodiments, L1 and L2 are each independently selected from single bonds or any of the following groups, where * indicates the linking site of the group:

[0045]

[0046] As a preferred embodiment, R1, R2, and R3 are each independently selected from any one or a combination of at least two of the following: hydrogen, deuterium, halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C12 (e.g., C6, C9, C10, etc.) aryl, and C3-C12 (e.g., C3, C4, C5, C6, C9, C10, etc.) heteroaryl.

[0047] Preferably, R1, R2, and R3 are each independently selected from any one or a combination of at least two of the following: hydrogen, deuterium, halogen, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophene, fluorenyl, and carbazole; more preferably, they are selected from any one of the following: hydrogen, deuterium, halogen, cyano, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothiophene, and deuterated dibenzothiophene. For example, R1 is selected from hydrogen or deuterium; and / or R2 and R3 are selected from hydrogen.

[0048] As a preferred embodiment, at least one H among Ar, L1, L2, R1, R2, and R3 is deuterated; preferably, the deuteration percentage is greater than or equal to 5% (e.g., 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 90%, 95%, 100%, or any value between them).

[0049] In this invention, the percentage of deuteration has its general meaning, specifically the percentage of all possible hydrogen atoms (e.g., hydrogen or deuterium positions) occupied by deuterium atoms in a compound.

[0050] As a preferred embodiment, the blue light host material is selected from any one of the following compounds:

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] In a second aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least one blue light host material as described in the first aspect; preferably comprising at least one compound with a structure shown in A1-A287.

[0063] Preferably, the organic layer includes a light-emitting layer, which includes at least one blue light host material as described in the first aspect; more preferably, it includes at least one compound with the structure shown in A1-A287.

[0064] Preferably, the mass percentage of the blue light-emitting material in the emitting layer is 80% to 99% (e.g., 82%, 84%, 86%, 88%, 90%, 92%, 94%, 96%, 98% or any value between them), based on the total mass of the emitting layer.

[0065] Preferably, the light-emitting layer further includes a dopant material (also known as a dopant, luminescent dye, dye, etc.), and the mass percentage of the dopant material can be 1% to 20% (e.g., 18%, 16%, 14%, 12%, 10%, 8%, 6%, 4%, 2% or any value between them), based on the total mass of the light-emitting layer.

[0066] Preferably, the doping material is a fluorescent doping material, and more preferably, a boron-nitrogen multiple resonance thermally activated delayed fluorescence doping material.

[0067] Preferably, the doping material is selected from any one of the following compounds:

[0068]

[0069] Preferably, the thickness of the light-emitting layer is 10-60nm, for example, it can be 12nm, 15nm, 18nm, 20nm, 22nm, 25nm, 28nm, 30nm, 32nm, 35nm, 38nm, 40nm, 42nm, 45nm, 48nm, 50nm, 52nm, 55nm, 58nm or any value between them, and more preferably 20-50nm.

[0070] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0071] Preferably, the hole transport region includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, and an electron blocking layer. The hole transport region may also include a hole auxiliary layer.

[0072] Preferably, the electron transport region includes any one or a combination of at least two of the following: an electron injection layer, an electron transport layer, and a hole blocking layer. The electron transport region may also include an electron buffer layer.

[0073] In a preferred embodiment, the organic electroluminescent device includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be further divided into multiple regions, such as a hole transport region, a light-emitting layer (which may also include a light-emitting auxiliary layer), and an electron transport region; the light-emitting layer includes at least one blue light-emitting host material as described in the first aspect; more preferably, it includes at least one compound with the structure shown in A1-A287.

[0074] In a preferred embodiment, the organic electroluminescent device includes a first electrode (anode), an organic layer, and a second electrode (cathode) sequentially disposed. The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer sequentially disposed, wherein the hole injection layer is in contact with the first electrode. The organic layer (preferably the light-emitting layer) includes at least one blue light-emitting host material as described in the first aspect; preferably, it includes at least one compound with the structure shown in A1-A287.

[0075] Thirdly, the present invention provides a display device or lighting device, including the organic electroluminescent device as described in the second aspect of the present invention.

[0076] In some implementations, the display device is a display device for smartphones, tablets, laptops, PCs, TVs, or automobiles.

[0077] In some implementations, the lighting device is an outdoor or indoor lighting device.

[0078] The present invention has the following beneficial effects: By introducing a rigid bispiro structure onto the anthracene group, the present invention can adjust its spatial configuration, increase the exciton recombination rate, thereby reducing the voltage of the device and enhancing the luminescence efficiency and lifespan of the device. Detailed Embodiments

[0079] In the following, the present invention will be described in detail. However, the following description is intended to explain the present invention and does not mean to limit the scope of the present invention in any way.

[0080] In the present invention, the halogen may each independently be fluorine, chlorine, bromine or iodine.

[0081] In the present invention, for the description of chemical elements, unless otherwise specified, the concept of isotopes with the same chemical properties is included. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0082] In the present invention, unless otherwise specified, the heteroatoms of the heteroaryl group are selected from N, O, S, P, B, Si or Se, preferably N, O or S. The heteroatoms of the heterocyclic alkyl group are selected from N, O, S, P, B, Si or Se, preferably N, O or S.

[0083] In the present invention, the expression of a ring structure with a "-" drawn across it indicates that the bonding site is at any position on the ring structure where bonding can occur.

[0084] In the present invention, both "-*" and "*" represent the bonding sites of the group.

[0085] In the present invention, "each independently" means that when the subject has multiple ones, they can be the same or different from each other.

[0086] In the present invention, the expression Ca-Cb represents that the group has a carbon atom number of a-b. Unless otherwise specified, the carbon atom number does not include the carbon atom number of the substituent.

[0087] In the present invention, the C1-C20 may each independently be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0088] In the present invention, the C3-C20 may each independently be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0089] In this invention, C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0090] In this invention, C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0091] In this invention, C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0092] In this invention, unless otherwise specified, the C6-C30 aryl (preferably C6-C20 aryl) includes monocyclic aryl and fused-ring aryl; the monocyclic aryl means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc.; the fused-ring aryl means that the group contains at least two rings (and at least one ring is an aromatic ring), and the rings share two adjacent carbon atoms fused together. Examples include, but are not limited to: naphthyl, anthracene, phenanthryl, indene, fluorenyl and their derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9-dinaphthylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl (benzo[A]fluorenyl, benzo[B]fluorenyl, benzo[C]fluorenyl), fluoranyl, triphenylene, pyrene, perylene, Aryl, tetraphenyl, acenaphthenyl, benzo[a]acenaphthenyl, etc. It should be noted that monocyclic aryl and fused-ring aryl groups linked by single bonds also fall under the category of aryl groups, such as phenylnaphthyl, naphthylphenyl, and binaphthyl.

[0093] In this invention, unless otherwise specified, the C3-C30 heteroaryl (preferably C3-C20 heteroaryl) and C5-C30 heteroaryl include monocyclic heteroaryl or fused-ring heteroaryl. A monocyclic heteroaryl means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, bipyridyl, phenylpyridinyl, pyridylphenyl, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), wherein the two share two adjacent atoms fused together in a group. Examples include, but are not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, dibenzofuranyl, benzonaphthofuranyl (benzo[B]naphtho[2,3-D]furanyl, benzo[B]naphtho[1,2-D) Furanyl, benzo[B]naphtho[2,1-D]furanyl), dibenzothiophene, benzo[B]naphtho[2,3-D]thiophene (benzo[B]naphtho[1,2-D]thiophene, benzo[B]naphtho[2,1-D]thiophene), carbazole and its derivatives (N-phenylcarbazole, N-naphthylcarbazole, benzocarbazole, dibenzocarbazole, indolecarbazole, azacarbazole, etc.), acridineyl, phenothiazinyl, phenotoxazinyl, hydrogenated acridineyl, etc.

[0094] In this invention, a specific example of the C6-C30 arylene can be a divalent group obtained by removing one hydrogen atom from the above-mentioned aryl examples; a specific example of the C5-C30 heteroarylene can be a divalent group obtained by removing one hydrogen atom from the above-mentioned heteroaryl examples.

[0095] In this invention, a specific example of the C6-C30 arylamino group is a monovalent group obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned aryl group. A specific example of the C3-C30 heteroarylamino group is a monovalent group obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned heteroaryl group.

[0096] In this invention, the C6-C30 aryloxy group is a monovalent group formed by attaching an aryl group to an oxygen group, as exemplified above; the C3-C30 heteroaryloxy group is a monovalent group formed by attaching an heteroaryl group to an oxygen group, as exemplified above. The C6-C30 arylthio group is a monovalent group formed by attaching an aryl group to an oxygen group, as exemplified above; the C3-C30 heteroarylthio group is a monovalent group formed by attaching an heteroaryl group to an oxygen group, as exemplified above.

[0097] In this invention, the C1-C20 alkyl group, preferably C1-C16 alkyl group, and more preferably C1-C10 alkyl group, includes straight-chain alkyl or branched-chain alkyl groups, and exemplary includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, etc.

[0098] In this invention, specific examples of the C1-C20 alkoxy group can be monovalent groups obtained by attaching the aforementioned alkyl group to O. Specific examples of the C1-C20 alkylsilyl group are monovalent groups obtained by replacing at least one hydrogen atom in -SiH3 with the aforementioned alkyl group.

[0099] In this invention, the C3-C20 cycloalkyl group, preferably C3-C10 cycloalkyl group, includes monocycloalkyl or polycycloalkyl groups. Monocycloalkyl refers to an alkyl group containing a single ring structure, while polycycloalkyl refers to a structure formed by two or more cycloalkyl groups sharing one or more carbon atoms on a ring. Exemplary examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0100] In this invention, specific examples of the C2-C20 heterocyclic alkyl group can be exemplified by groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (e.g., N, O, S, etc.), including but not limited to: epoxy group, oxetane, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrroleyl, tetrahydropyranyl, piperidinyl, piperazineyl, dioxaneyl, morpholinyl, etc.

[0101] In this invention, the C2-C20 alkenyl group, preferably C2-C10 alkenyl group, contains at least one C=C, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0102] In this invention, "combination" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by a person skilled in the art from the applicable list. Examples include combinations of alkyl / aryl and deuterium to form partially or fully deuterated alkyl / aryl groups (e.g., deuterated methyl, deuterated ethyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, etc.); combinations of halogen and alkyl to form partially or fully haloalkyl groups (e.g., trifluoromethyl, etc.); combinations of alkyl and aryl to form alkylaryl groups (methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, isopropylphenyl, diisopropylphenyl, tert-butylphenyl, di-tert-butylphenyl, isobutylphenyl, tert-pentylphenyl, neopentylphenyl, etc.) or arylalkyl groups (e.g., phenyl tert-butyl, etc.); and combinations of halogen, alkyl, and aryl to form haloarylalkyl groups, etc.

[0103] The specific preparation method of the blue light host material of the present invention will be described in detail below using several synthetic examples, but the preparation method of the present invention is not limited to these synthetic examples.

[0104] Synthesis Example 1: Synthesis of Compound A1

[0105]

[0106] Under nitrogen protection, starting materials M1-1 (0.1 mol), M1-2 (0.1 mol), potassium carbonate (0.2 mol), tetra(triphenylphosphine)palladium (0.002 mol), water (30 mL), and dioxane (300 mL) were added to a dry three-necked reaction flask. The mixture was heated to 85 °C and reacted for 7 h. The mixture was then cooled to room temperature, extracted with water and dichloromethane, and the organic phase was separated, concentrated, and purified by column chromatography to give compound A1 (yield 78.6%). The MS (m / e) value of compound A1 was 472.57.

[0107] Synthesis Example 2: Synthesis of Compound A47

[0108]

[0109] (2-1) Synthesis of intermediate S2-1:

[0110] Under nitrogen protection, starting material M1-1 (0.15 mol), starting material M2-1 (0.2 mol), potassium acetate (0.25 mol), 1,1-bis(diphenylphosphine)ferrocene palladium dichloride (0.003 mol), and dioxane (1000 mL) were added to a dry three-necked reaction flask, and the mixture was heated to 90 °C and reacted for 6 h. The mixture was then cooled to room temperature, extracted with water and dichloromethane, and the organic phase was separated, concentrated, and purified by column chromatography to give intermediate S2-1 (yield 77.1%).

[0111] (2-2) Synthesis of compound A47

[0112] The synthesis method of compound A47 is the same as that of compound A1, except that starting material M1-1 is replaced with starting material M2-2, and starting material M1-2 is replaced with intermediate S2-1, thus obtaining compound A47. The MS (m / e) of compound A47 is 638.02.

[0113] Synthesis Example 3: Synthesis of Compound A80:

[0114]

[0115] (3-1) Synthesis of intermediate S3-1:

[0116] Under nitrogen protection, starting material M3-1 (0.15 mol), starting material M3-2 (0.15 mol), potassium carbonate (0.3 mol), tetra(triphenylphosphine)palladium (0.003 mol), water (40 mL), and dioxane (400 mL) were added to a dry three-necked reaction flask, and the mixture was heated to 85 °C and reacted for 7 h. The mixture was then cooled to room temperature, and water and dichloromethane were added for extraction. After separating the organic phase, the mixture was concentrated and purified by column chromatography to obtain intermediate S3-1 (yield 80.2%).

[0117] (3-2) Synthesis of compound A80:

[0118] The synthesis method of compound A80 is the same as that of compound A47, except that the starting material M2-2 is replaced with intermediate S3-1 to obtain compound A80. The MS (m / e) of compound A80 is 730.22.

[0119] Synthesis Example 4: Synthesis of Compound A120:

[0120]

[0121] The synthesis method of compound A120 is the same as that of compound A80, except that starting material M3-1 is replaced with starting material M4-1, and starting material M3-2 is replaced with starting material M4-2, to obtain compound A120. The MS (m / e) of compound A120 is 724.79.

[0122] Synthesis Example 5: Synthesis of Compound A166:

[0123]

[0124] The synthesis method of compound A166 is the same as that of compound A80, except that starting material M3-1 is replaced with starting material M5-1, and starting material M3-2 is replaced with starting material M5-2, to obtain compound A166. The MS (m / e) of compound A166 is 812.65.

[0125] Synthesis Example 6: Synthesis of Compound A185:

[0126]

[0127] (6-1) Synthesis of intermediate S6-1:

[0128] The synthesis method of intermediate S6-1 is the same as that of intermediate S3-1, except that raw material M3-1 is replaced with raw material M6-1 and raw material M3-2 is replaced with raw material M6-2 to obtain intermediate S6-1.

[0129] (6-2) Synthesis of intermediate S6-2:

[0130] The synthesis method of intermediate S6-2 is the same as that of intermediate S2-1, except that the raw material M1-1 is replaced with intermediate S6-1 to obtain intermediate S6-2.

[0131] (6-3) Synthesis of intermediate S6-3:

[0132] The synthesis method of intermediate S6-3 is the same as that of intermediate S3-1, except that the raw material M3-1 is replaced with intermediate S6-2 to obtain intermediate S6-3.

[0133] (6-4) Synthesis of intermediate S6-4:

[0134] Under nitrogen protection, intermediate S6-3 (0.1 mol), starting material M6-3 (0.1 mol), potassium carbonate (0.2 mol), tetra(triphenylphosphine)palladium (0.002 mol), water (30 mL), and dioxane (300 mL) were added to a dry three-necked reaction flask, and the mixture was heated to 85 °C and reacted for 7 h. The mixture was then cooled to room temperature, extracted with water and dichloromethane, and the organic phase was separated, concentrated, and purified by column chromatography to obtain intermediate S6-4 (yield 77.7%).

[0135] (6-5) Synthesis of compound A185:

[0136] The synthesis method of compound A185 is the same as that of A1, except that the starting material M1-2 is replaced with intermediate S6-4 to obtain compound A185. The MS (m / e) of compound A185 is 781.16.

[0137] Synthesis Example 7: Synthesis of Compound A196:

[0138]

[0139] The synthesis method of compound A196 is the same as that of A47, except that the starting material M2-2 is replaced with starting material M7-1 to obtain compound A196. The MS (m / e) of compound A196 is 561.73.

[0140] Synthesis Example 8: Synthesis of Compound A215:

[0141]

[0142] The synthesis method of compound A215 is the same as that of A185, except that intermediate S6-3 is replaced with starting material M8-1, and starting material M6-3 is replaced with starting material M8-2, to obtain compound A215. The MS (m / e) of compound A215 is 758.61.

[0143] Synthesis Example 9: Synthesis of Compound A223:

[0144]

[0145] (9-1) Synthesis of intermediate S9-1:

[0146] The synthesis method of intermediate S9-1 is the same as that of intermediate S6-4, except that intermediate S6-3 is replaced with raw material M9-1 to obtain intermediate S9-1.

[0147] (9-2) Synthesis of intermediate S9-4:

[0148] The synthesis method of intermediate S9-4 is the same as that of intermediate S6-3. The only difference is that raw material M6-1 is replaced with intermediate S9-1, raw material M6-2 is replaced with raw material M9-2, and raw material M3-2 is replaced with raw material M9-3 to obtain intermediate S9-4.

[0149] (9-3) Synthesis of compound A223:

[0150] The synthesis method of compound A223 is the same as that of compound A185, except that the starting material M1-1 is replaced with intermediate S9-4, and intermediate S6-4 is replaced with intermediate S2-1, thus obtaining compound A223. The MS (m / e) of compound A223 is 868.20.

[0151] Synthesis Example 10: Synthesis of Compound A240:

[0152]

[0153] The synthesis method of compound A240 is the same as that of compound A223, except that intermediate S9-2 is replaced with starting material M10-1, and starting material M9-3 is replaced with starting material M10-2, to obtain compound A240. The MS (m / e) of compound A240 is 749.76.

[0154] Synthesis Example 11: Synthesis of Compound A243:

[0155]

[0156] (11-1) Synthesis of intermediate S11-1:

[0157] Add potassium hydroxide (0.1 mol), acetone (100 mL), water (300 mL), and ethanol (300 mL) to a dry three-necked reaction flask. Then, add raw material M11-1 (0.1 mol) and raw material M11-2 (0.1 mol) dropwise and stir overnight at room temperature. After the reaction is complete, filter under reduced pressure to obtain a solid. Add the solid to a mixed solution of glacial acetic acid and ethyl acetate (200 mL, v / v = 1 / 4), then add Pd / C (6 g, 5%), and then purge with hydrogen gas. Stir the reaction at room temperature and pressure for 10 h. After the reaction is complete, filter, wash with saturated NaHCO3 solution and water, filter under reduced pressure, dry, dissolve the residue in diethyl ether (500 mL), then add sodium dichromate dihydrate (25 g) and concentrated sulfuric acid solution (6 mL / 50 mL), and stir overnight at room temperature. The phases were separated, the aqueous phase was washed with diethyl ether, the organic phase was washed with saturated NaHCO3 solution and water, dried with anhydrous sodium sulfate, filtered under reduced pressure, and dried under vacuum to obtain intermediate S11-1 (yield 52.5%). (11-2) Synthesis of intermediate S11-2:

[0158] Intermediate S11-1 (0.05 mol), silicomolybdic acid (0.0025 mol), and benzene (300 mL) were added to a dry three-necked reaction flask, and the mixture was heated under reflux for 8 h. After the reaction was completed, the mixture was cooled to room temperature, filtered, washed with chloroform, evaporated under reduced pressure, and purified by column chromatography to obtain intermediate S11-2 (yield 30.4%).

[0159] (11-3) Synthesis of compound A243:

[0160] The synthesis method of compound A243 is the same as that of compound A1, except that starting material M1-1 is replaced with intermediate S11-2, and starting material M1-2 is replaced with starting material M11-3, to obtain compound A243. The MS (m / e) of compound A243 is 522.58.

[0161] This invention provides exemplary methods for synthesizing the above-mentioned compounds. Other compounds for which no specific synthesis method is provided can also be prepared using similar methods, requiring only the replacement of raw materials. These methods will not be elaborated here. Alternatively, those skilled in the art can prepare these compounds using other methods in the prior art.

[0162] Device Example 1:

[0163] An organic electroluminescent device is fabricated as follows: A glass substrate with a 120 nm thick indium tin oxide (ITO) anode is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then the substrate is mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 In the case of Torr, The deposition rate was achieved sequentially on the ITO anode using thermal vacuum. First, compounds HT and HI (97:3, w / w) were co-deposited as a hole injection layer (HIL) with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, compound A1, the blue light-emitting host material, and compound BD5 (98:2, w / w), the dopant material, were co-deposited as the emissive layer (EML) with a thickness of [missing information]. Compound HB is used as a hole blocking layer (HBL) with a thickness of [missing information]. The compound ET and 8-hydroxyquinoline-lithium (Liq) (50:50, w / w) were co-deposited as an electron transport layer (ETL) with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by vapor deposition. A thick layer of aluminum is used as the cathode. The device is then transferred back to the glove box and sealed with a glass cover to complete the device.

[0164] Device Examples 2-11, Device Comparative Examples 1-3

[0165] An organic electroluminescent device is disclosed, which differs from device example 1 only in that the blue light-emitting substrate material of the light-emitting layer is the compound shown in Table 1; the other layers, thicknesses, materials and preparation methods are the same as those in device example 1.

[0166] The molecular structural formulas of the relevant materials are shown below:

[0167]

[0168] Performance testing:

[0169] Table 1 lists the values ​​at 10 mA / cm 2 Voltage (V), external quantum efficiency (EQE, %), and lifetime (LT) measured at current density 95 (h). To better illustrate the data comparison, the voltage, external quantum efficiency, and lifetime of Device Comparative Example 1 were set to 1.00, while the voltage, external quantum efficiency, and lifetime of other devices were the ratios of their respective test values ​​to the test values ​​of Device Comparative Example 1.

[0170] Table 1

[0171] Device Number Main materials Voltage (relative value) EQE (Relative Value) <![CDATA[LT 95 (relative value) Device Example 1 A1 0.96 1.21 1.16 Device Example 2 A47 0.93 1.26 1.13 Device Example 3 A80 0.94 1.23 1.29 Device Example 4 A120 0.93 1.24 1.21 Device Example 5 A166 0.94 1.20 1.33 Device Example 6 A185 0.92 1.25 1.38 Device Example 7 A196 0.93 1.18 1.31 Device Example 8 A215 0.94 1.27 1.30 Device Example 9 A223 0.96 1.17 1.32 Device Example 10 A240 0.92 1.24 1.41 Device Example 11 A243 0.94 1.13 1.15 Device Comparison Example 1 D1 1.00 1.00 1.00 Device Comparison Example 2 D2 0.98 0.97 1.06 Device Comparison Example 3 D3 0.97 1.08 1.02

[0172] As can be seen from Table 1, the organic electroluminescent devices prepared using the compounds of this invention as the blue light host material of the luminescent layer have low voltage, excellent luminous efficiency and lifetime.

[0173] Although the present invention has been described in detail above with general descriptions, specific embodiments, and experiments, it is not intended to limit the scope of the invention, as will be obvious to those skilled in the art. Therefore, any modifications or improvements made without departing from the spirit of the invention are within the scope of protection claimed by the present invention.

Claims

1. A blue light-emitting substrate material, said blue light-emitting substrate material having a structure as shown in Formula I: in, Ar is selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C5-C30 heteroaryl groups; L1 and L2 are each independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C5-C30 heteroarylene; a is any integer from 0 to 8; b is any integer from 0 to 3; c is any integer from 0 to 4. R1, R2, and R3 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 arylthio, and substituted or unsubstituted C3-C30 heteroarylthio. The substituents described in Ar, L1, L2, R1, R2, and R3 are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, and C3-C30 heteroarylthio.

2. The blue light-emitting substrate material according to claim 1, characterized in that, The blue light host material has a structure as shown in any one of Formula II-1, Formula II-2, Formula II-3, or Formula II-4: The definitions of Ar, L1, L2, R1, R2, R3, a, b, and c are the same as those in Equation I.

3. The blue light-emitting substrate material according to claim 1 or 2, characterized in that, Ar is selected from any one of substituted or unsubstituted C6-C25 aryl groups and substituted or unsubstituted C10-C25 heteroaryl groups; Optionally, the substituents in Ar are each independently selected from any one or a combination of at least two of deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C25 aryl, and C3-C25 heteroaryl. Preferably, the Ar is selected from any of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, binaphthyl, anthracene, phenanthryl, fluorenyl, spirodifluorenyl, dibenzofuranyl, benzonaphthuryl, dibenzothiophenyl, benzonaphthiophenyl, N-phenylcarbazoyl, carbazoyl; Optionally, the substituents in Ar are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, and carbazoleyl. Preferably, the Ar is selected from any of the following groups, whether deuterated or unsubstituted, where * indicates the linkage site of the group: Preferably, the Ar is selected from any of the following groups, where * indicates the linkage site of the group: Preferably, the Ar is selected from any of the following groups, where * indicates the linkage site of the group:

4. The blue light-emitting substrate material according to any one of claims 1-3, characterized in that, L1 and L2 are each independently selected from any one of single bond, substituted or unsubstituted C6-C25 arylene, or substituted or unsubstituted C10-C25 heteroarylene; Optionally, the substituents in L1 and L2 are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C25 aryl, and C3-C25 heteroaryl. Preferably, L1 and L2 are each independently selected from any of the following groups: single bond, deuterated, or unsubstituted, where * indicates the linkage site of the group: Preferably, L1 and L2 are each independently selected from single bonds or any of the following groups, where * indicates the linkage site of the group: Preferably, L1 and L2 are each independently selected from single bonds or any of the following groups, where * indicates the linkage site of the group:

5. The blue light-emitting substrate material according to any one of claims 1-4, characterized in that, R1, R2, and R3 are each independently selected from any one or a combination of at least two of the following: hydrogen, deuterium, halogen, cyano, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C12 aryl, and C3-C12 heteroaryl. Preferably, R1, R2, and R3 are each independently selected from any one or a combination of at least two of hydrogen, deuterium, halogen, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, tert-pentyl, neopentyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophene, fluorenyl, and carbazole; more preferably, they are selected from any one of hydrogen, deuterium, halogen, cyano, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothiophene, and deuterated dibenzothiophene. For example, R1 is selected from hydrogen or deuterium; and / or R2 and R3 are selected from hydrogen.

6. The blue light-emitting substrate material according to any one of claims 1-5, characterized in that, The blue light-emitting substrate material is selected from any one of the following compounds:

7. An organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least one blue light host material as described in any one of claims 1-6; Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one blue light host material as described in any one of claims 1-6; Preferably, the mass percentage of the blue light-emitting material in the light-emitting layer is 80% to 99%, based on the total mass of the light-emitting layer; Preferably, the light-emitting layer further includes a doping material; Preferably, the doping material is a fluorescent doping material, and more preferably, a boron-nitrogen multiple resonance thermally activated delayed fluorescence doping material.

8. The organic electroluminescent device according to claim 7, characterized in that, The doping material is selected from any one of the following compounds:

9. The organic electroluminescent device according to claim 7 or 8, characterized in that, The thickness of the light-emitting layer is 10-60 nm, more preferably 20-50 nm; Preferably, the organic layer further includes a hole transport region and an electron transport region; Preferably, the hole transport region includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, and an electron blocking layer; Preferably, the electron transport region includes any one or a combination of at least two of the electron injection layer, electron transport layer, and hole blocking layer.

10. A display device or lighting device comprising the organic electroluminescent device of any one of claims 7-9.

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