Organic light-emitting device and display device

Abstract

The invention relates to an organic electroluminescent device and a display device, and belongs to the technical field of organic electroluminescence. The organic light-emitting device comprises an organic light-emitting layer, the organic light-emitting layer comprises a main body material and a doped dye, the main body material has a structure as shown in a formula I, and the dye has a structure as shown in a formula II. Wherein the energy corresponding to a light-emitting peak with the highest energy in the emission spectrum of the main body material is recorded as E1, and the energy corresponding to an absorption peak with the lowest energy in the absorption spectrum of the dye is recorded as E2; e1 is larger than E2, and E1-E2 is larger than or equal to 0.10 eV and smaller than or equal to 0.30 eV. According to the device disclosed by the invention, a method of co-doping the anthracene derivative main body material and the boron-nitrogen heterocyclic fluorescent dye is adopted, and the energy relationship between the anthracene derivative main body material and the boron-nitrogen heterocyclic fluorescent dye used as the luminescent dye is controlled, so that the performance of the device is effectively improved; the prepared OLEDs have the characteristics of high color purity, high efficiency, low roll-off and high stability.

Description

Technical Field

[0001] This invention relates to an organic electroluminescent device and a display device, specifically an organic electroluminescent device that uses anthracene derivatives as the main material and boron-nitrogen heterocyclic compounds as luminescent dyes, belonging to the field of organic electroluminescence technology. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are devices that emit light by being driven by an electric current. Their main characteristics come from their organic light-emitting layer. When an appropriate voltage is applied, electrons and holes combine in the organic light-emitting layer to generate excitons, which emit light of different wavelengths according to the characteristics of the organic light-emitting layer.

[0003] Further improving the color purity, efficiency, and lifespan of OLEDs remains a long-term goal pursued by the industry; the development of the emissive layer substrate and emissive dyes remains key to solving these problems. Various derivatives of anthracene compounds are the main source of substrate materials. In recent years, a class of emissive dyes with boron-nitrogen resonance structure characteristics has attracted much attention. They exhibit a distinctly narrow emission spectrum and a small Stokes shift between their absorption and emission spectra.

[0004] However, as OLED products gradually enter the market, people have increasingly higher requirements for their performance. Current OLED materials and device structures cannot fully solve the problems related to efficiency, lifespan, and cost of OLED products. Summary of the Invention

[0005] In view of the shortcomings of the prior art, one of the objectives of the present invention is to provide an organic electroluminescent device that has high luminous efficiency and long lifespan.

[0006] The organic electroluminescent device of the present invention includes a substrate, a first electrode, a second electrode, and an organic functional layer, wherein the organic functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes a host material and a light-emitting dye;

[0007] The feature is that the energy corresponding to the highest energy emission peak in the emission spectrum of the main material is denoted as E1, and the energy corresponding to the lowest energy absorption peak in the absorption spectrum of the luminescent dye is denoted as E2.

[0008] The value E1 > E2, and 0.10eV ≤ E1 - E2 ≤ 0.30eV; for example, 0.10eV, 0.12eV, 0.14eV, 0.15eV, 0.18eV, 0.20eV, 0.22eV, 0.25eV, 0.28eV, 0.30eV, etc.

[0009] The main material has the structure shown in Formula I:

[0010]

[0011] In Formula I, A and B are independently selected from one of unsubstituted or R'-substituted C6-C60 aryl groups and unsubstituted or R'-substituted C3-C60 heteroaryl groups;

[0012] In Formula I, R1 and R2 independently represent substituents from a single substituent to the maximum permissible number, R 1 and R 2 Each is independently selected from one of the following: hydrogen, halogen, amino, hydroxyl, ester, cyano, nitro, unsubstituted or R'-substituted C1-C20 chain alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 silyl, unsubstituted or R'-substituted C1-C20 thioalkoxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl, unsubstituted or R'-substituted C6-C60 arylamino, and unsubstituted or R'-substituted C3-C60 heteroarylamino.

[0013] The luminescent dye is a boron-nitrogen heterocyclic fluorescent dye with the structure shown in Formula II:

[0014]

[0015] In formula II, R 1 ~R 10 Each group is independently selected from hydrogen, deuterium, halogen, hydroxyl, carboxyl, nitro, cyano, sulfone, sulfoxide, alkynyl, or unsubstituted or R'-substituted groups of the following: C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkyl, C6-C30 acyl, C6-C30 amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused-ring aryl, C6-C60 aryloxy, C6-C60 arylphosphinyl, C5-C60 monocyclic heteroaryl, C5-C60 fused-ring heteroaryl, C6-C30 alkylsilyl, C6-C30 arylsilyl, or C6-C30 heteroarylsilyl.

[0016] The R' is independently selected from one of deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

[0017] Through extensive experiments, the researchers of this invention discovered a significant performance gap between devices made using various anthracene derivatives as the luminescent host material and boron-nitrogen heterocyclic compounds as fluorescent dyes. Further research revealed that by adjusting and screening specific luminescent host materials and dyes, ensuring that the emission spectra of the host material and the absorption spectra of the dye are within a certain reasonable range, and through extensive experimental verification, high-performance blue light-emitting devices can be obtained.

[0018] During operation, OLED devices continuously generate excitons through the combination of electrons and holes in the light-emitting layer. This electron-hole combination can occur on the host material or the guest material. If the excitons are generated on the host material, they need to transfer energy to the guest material to emit light efficiently. The color of the device is mainly determined by the energy of the excitons on the guest material. The energy of the exciton depends on the energy level of the material it resides in, which is determined by the material's chemical structure. Energy transfer refers to the transfer of excitons from a higher-energy material to a lower-energy material. The higher-energy material that provides the exciton is called the energy donor, and the lower-energy material that receives the exciton is called the energy acceptor. In this invention, the compound represented by Formula I serves as both the host and energy donor material; the compound represented by Formula II serves as both the guest and energy acceptor material.

[0019] This invention ensures the transfer of excitons from the host material to the dye by making the exciton energy of the host material greater than that of the dye, thereby effectively improving the luminous efficiency and lifetime of the device. However, extensive experimental verification and analysis have revealed that the energy difference between the two must be controlled within the range of 0.10 eV-0.30 eV to achieve this effect; an energy difference that is too large or too small will reduce efficiency and lifetime.

[0020] There are multiple ways to transfer exciton energy; for example, it can be done through... This is achieved through energy transfer mechanisms. Energy transfer rate k = (1 / τ) D )×(R0 / r) 6 , where τ D Let be the lifetime of the donor's fluorescent excited state, r be the actual distance between the donor and acceptor, and R0 be the effective energy transfer distance, which is proportional to the spectral overlap between the donor's emission spectrum and the acceptor's absorption spectrum. It can be seen that, when the distance between the donor and acceptor is the same, the greater the overlap between the donor's emission spectrum and the acceptor's absorption spectrum, the more efficient the energy transfer. The higher the energy transfer rate.

[0021] Please refer to the schematic diagram of the light-emitting mechanism in the light-emitting layer of the organic electroluminescent device of this invention.Figure 1 As shown, two triplet excitons recombine on a host with a lower triplet energy level undergo triplet-triplet annihilation to produce energy similar to the host's singlet state, and then upconvert to its singlet state. Energy transfer to dye molecules enables highly efficient luminescence. In this invention, the dye, acting as the acceptor, has a distinctly rigid structure and a narrow absorption spectrum. Therefore, the emission spectrum of the donor needs to be as close as possible to the absorption spectrum of the acceptor to maximize spectral overlap. Consequently, the energy difference between the emission spectrum of the host material (the donor) and the absorption spectrum of the dye (the acceptor) cannot be too large. Furthermore, since an excessively small energy difference cannot ensure the prevention of reverse energy transfer from the dye to the host, the energy difference between the emission spectrum of the host material (the donor) and the absorption spectrum of the dye (the acceptor) cannot be too small.

[0022] The excited-state energy of a material can be determined by the energies of its absorption and emission spectra. The absorption and emission spectra of a material are related to its current state.

[0023] In this invention, emission spectrum specifically refers to fluorescence emission spectrum.

[0024] In this invention, "the energy corresponding to the highest energy emission peak in the emission spectrum is denoted as E1" means that: there may be one or at least two emission peaks in the emission spectrum. When there is only one emission peak, the peak energy of that emission peak is denoted as E1. When there are at least two emission peaks, the highest emission peak is selected, and its peak energy is denoted as E1. "The energy corresponding to the lowest energy absorption peak in the absorption spectrum is denoted as E2" is similar, the only difference being that the lowest peak is selected.

[0025] In this invention, one of the first electrode and the other of the second electrode is an anode and the other is a cathode. For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0026] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, when the same expression is used, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0027] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0028] In this specification, the way a ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0029] In this specification, "each independently" or "independently" means that when there are multiple subjects, they may be the same or different from each other.

[0030] In this invention, the description of chemical elements, unless otherwise specified, usually includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes the concept of its isotopes 1H (protium or H) and 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., which will not be elaborated further.

[0031] In this invention, heteroatoms generally refer to atoms or groups of atoms selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0032] Examples of halogens in this specification include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.

[0033] In this invention, unless otherwise specified, aryl and heteroaryl groups include both monocyclic and fused-ring types.

[0034] In this invention, C6-C60 can be 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, etc.

[0035] C3-C60 can all be 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, etc.

[0036] C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0037] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0038] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0039] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0040] C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0041] In this invention, the substituted or unsubstituted C6-C60 aryl (aromatic ring) includes monocyclic aryl (aromatic ring) and fused-ring aryl (aromatic ring), preferably C6-C30 aryl, and more preferably C6-C20 aryl. A monocyclic aryl (aromatic ring) refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, exemplarily such as phenyl, biphenyl, terphenyl, etc. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl. A fused-ring aryl (aromatic ring) refers to a molecule containing at least two aromatic rings, where the aromatic rings are not independent of each other but share two adjacent carbon atoms fused together. Examples of such groups include naphthyl, anthraceneyl, phenanthryl, indene, fluorenyl, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, and their derivatives. The naphthyl group includes 1-naphthyl or 2-naphthyl; the anthraceneyl group is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyreneyl group is selected from 1-pyrene, 2-pyrene, and 4-pyrene; and the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl, and 9-tetraphenyl. The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl.

[0042] The C3-C60 heteroaryl (heteroaryl ring) mentioned in this invention includes monocyclic heteroaryl (heteroaryl ring) and fused-ring heteroaryl (heteroaryl ring), preferably C3-C30 heteroaryl, more preferably C4-C20 heteroaryl, and even more preferably C5-C12 heteroaryl. A monocyclic heteroaryl (heteroaryl ring) refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, and pyridinyl. A fused-ring heteroaryl refers to a molecule containing at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share two adjacent atoms fused together. Examples of fused-ring heteroaryl groups include: benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, acridineyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazoyl, azircarbazoyl, phenothiazinyl, phenothiazinyl, 9-phenylcarbazoyl, 9-naphthylcarbazoyl, dibenzocarbazoyl, indolocarbazoyl, etc.

[0043] The aryl group in this invention can be exemplified by the monovalent group composed of the above-mentioned aryl and heteroaryl groups and oxygen.

[0044] In this invention, arylamino represents a group formed by replacing the hydrogen on an amino group with one or two aryl groups, wherein the linking site of the arylamino can be linked to the aryl group in the arylamino or to the N group in the arylamino, and the exemplary number of carbons and specific groups of the aryl group in the arylamino are the same as described above.

[0045] Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0046] Examples of C3-C30 heteroaryl amino groups mentioned in this invention include pyridinyl amino, pyrimidinyl amino, and dibenzofuranyl amino.

[0047] Unless otherwise specified, the chain alkyl groups mentioned in this invention include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, substituted or unsubstituted C1-C30 chain alkyl groups are preferably substituted or unsubstituted C1-C16 chain alkyl groups, and more preferably substituted or unsubstituted C1-C10 chain alkyl groups. Examples of substituted or unsubstituted C1-C10 chain alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0048] In this invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single ring structure; polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on a ring; examples of C3-C20 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0049] In this specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of C1-C10 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentooxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy, and isopentoxy are preferred, and methoxy is more preferred.

[0050] In this specification, the substituted or unsubstituted C1-C20 silanes and the substituted or unsubstituted C1-C10 silanes are examples of silanes substituted with groups listed in the above C1-C10 silanes, specifically including: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, etc.

[0051] It should be noted that while the possible effects of each group / feature have been described separately for ease of explanation in this application, this does not mean that these groups / features act in isolation. In fact, the reason for achieving good performance is essentially the optimized combination of the entire molecule, the result of the synergistic effect between various groups, rather than the effect of a single group.

[0052] In this invention, E1 is the energy corresponding to the highest energy emission peak in the emission spectrum of the solution of the host material; and E2 is the energy corresponding to the lowest energy absorption peak in the absorption spectrum of the solution of the dye.

[0053] In this invention, the solvent and concentration of the solution of the main material and the solution of the dye are the same, exemplarily 10. -6 mol / L to 10 -5 mol / L.

[0054] Preferably, the test temperature for the emission spectrum is the same as the test temperature for the absorption spectrum, preferably 25°C.

[0055] In one aspect of the invention, both the absorption and emission spectra of the material are measured in a dilute solution, wherein the dilute solution refers to a solution with a concentration of 10... -6 Up to 10 -5 Solutions with concentrations between mol / L. In another aspect of the invention, different materials are dissolved in the same solvent to prepare dilute solutions for measuring their absorption and emission spectra. Common solvents include, but are not limited to, n-hexane, cyclohexane, n-heptane, petroleum ether, dichloromethane, chloroform, toluene, xylene, tetrahydrofuran, 2-methyltetrahydrofuran, acetone, ethyl acetate, etc. Preferably, all dilute solutions use 2-methyltetrahydrofuran as the solvent.

[0056] The absorption spectrum of dilute solutions can be determined using a UV-Vis spectrophotometer. The emission spectrum of dilute solutions can be determined using a photoluminescence spectrophotometer.

[0057] More preferably, in Formula I, A and B are each independently selected from one of unsubstituted or R'-substituted C6-C18 aryl groups and one of unsubstituted or R'-substituted C8-C18 heteroaryl groups, and at least one of A and B is one of unsubstituted or R'-substituted C10-C18 fused-ring aryl groups and one of unsubstituted or R'-substituted C8-C18 fused-ring aryl groups;

[0058] The R' is independently selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

[0059] R1 and R2 are each independently selected from hydrogen, deuterium, or one or a combination of at least two of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethynyl, trimethylsilylethynyl, tert-butylethynyl, triisopropylsilylethynyl, phenyl, tert-butylphenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, peryl, fluoranyl, azulene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, aziridine, azobiphenyl, terphenyl, triphenyl Phenyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, indene, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, triphenylene, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl Thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, benzoindole, carbazole, benzocarbazole, indocarbazole, dibenzocarbazole, pyridinyl, bipyridinyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, benzoquinazolinyl, benzodioxacyclopentenyl, acridine, dihydroacridinyl, phenanthridine Benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthomidazoleyl, phenanthrenemidazoleyl, pyridiniumimidazolyl, pyraziniumimidazolyl, quinoxaloylimidazolyl, oxazolyl, isoxazolyl, benzoxazolyl, benzoisoxazolyl, naphthomidazoleyl, anthraquinoxazolyl, phenanthrenemidazole 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, benzoisothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, benzoquinoxalinyl, 5,10-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene 4,5,9,10-Tetraazaperyl, Pyrazinyl, Phenazinyl, Phenoxazinyl, Phenthiazinyl, Naphridinyl, Azacarbazolyl, Benzocarbazolyl, Phenanthrolinel, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Benzotriazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetrazinyl, 1,2,3,4-Tetrazinyl, 1,2,3,5-Tetrazinyl, Purinyl, Pteridyl, Indazinyl, Benzothiadiazolyl, 9,9-Dimethylacridyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrolyl, piperidinyl, methoxy, trisenel, cyclosenel, tetrastyrene, naphthimide, triphenylboryl, cycloheptanetrienyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, triphenylsilyl, dimethylphenylsilyl, diphenylmethylsilyl, or tert-butyldiphenylsilyl.

[0060] More preferably, in Formula I, A and B are independently selected from any one of the following groups:

[0061]

[0062] Wherein, * represents the linking site of a group; the R' is independently selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, and C1-C10 alkoxy.

[0063] More preferably, in Formula I, A is selected from one of unsubstituted or R'-substituted naphthyl, unsubstituted or R'-substituted dibenzofuranyl, and R' is independently selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

[0064] Furthermore, in formula II, the R 1 ~R 10Each group is independently selected from hydrogen, deuterium, or one or more combinations of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethynyl, trimethylsilylethynyl, tert-butylethynyl, triisopropylsilylethynyl, phenyl, tert-butylphenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, peryl, uryl, fluoranyl, azulene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azabiphenyl, azobiphenyl, terphenyl, Phenylacetyl, naphthylphenyl, phenyl terphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, indene, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, triphenylene, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl, thiazolyl Fenyl, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, benzoindole, carbazole, benzocarbazole, indocarbazole, dibenzocarbazole, pyridyl, bipyridyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, benzoquinazolinyl, benzodioxanepentenyl, acridine, dihydroacridyl, phenanthridine, benzene benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthomidazoleyl, phenanthrenemidazoleyl, pyridiniumimazoleyl, pyraziniumimazoleyl, quinoxaloylimazoleyl, oxazolyl, isoxazolyl, benzoxazolyl, benzoisoxazolyl, naphthomidazoleyl, anthraquinoxazolyl, phenanthrenemidazoleyl 1,2-Thiazolyl, 1,3-Thiazolyl, benzothiazolyl, benzoisothiazolyl, pyridinyl, benzopyridinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, benzoquinoxalinyl, 5,10-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4 5,9,10-Tetraazaperyl, Pyrazinyl, Phenazinyl, Phenoxazinyl, Phenthiazinyl, Naphridinyl, Azacarbazolyl, Benzocarbazolyl, Phenanthrolinel, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Benzotriazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetrazinyl, 1,2,3,4-Tetrazinyl, 1,2,3,5-Tetrazinyl, Purinyl, Pteridyl, Indazinyl, Benzothiadiazolyl, 9,9-Dimethylacridyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrolyl, piperidinyl, methoxy, trisenel, cyclosenel, tetrastyrene, naphthimide, triphenylboryl, cycloheptanetrienyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, triphenylsilyl, dimethylphenylsilyl, diphenylmethylsilyl, or tert-butyldiphenylsilyl.

[0065] More preferably, in the organic electroluminescent device of the present invention, the boron-nitrogen heterocyclic fluorescent dye used as the dye has the structure shown in Formula III:

[0066]

[0067] In Formula III, group R 9 and R 10 The scope of the definition is the same as that in equation (2);

[0068] Preferably, the R 9 R 10 Each group is independently selected from one of the following groups:

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] in Indicates the linking site of a functional group.

[0075] Preferably, the host material in the organic electroluminescent device of the present invention is selected from the following specific structural compounds, which are only representative examples:

[0076]

[0077]

[0078] Preferably, the boron-nitrogen heterocyclic fluorescent dye in the organic electroluminescent device of the present invention is selected from the following specific structural compounds, which are only representative examples:

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] Preferably, E1 ≤ 3.0 eV, for example 2.0 eV, 2.1 eV, 2.2 eV, 2.3 eV, 2.4 eV, 2.5 eV, 2.6 eV, 2.7 eV,

[0094] 2.8 eV, 2.9 eV, 3.0 eV, etc., and / or, E2 ≥ 2.6 eV, such as 2.62 eV, 2.72 eV, 2.74 eV, 2.76 eV, 2.78 eV, etc.

[0095] 2.8eV, 2.83eV, 2.85eV, 2.87eV, 2.89eV, 2.91eV, 2.93eV, etc.

[0096] Researchers have discovered that high-energy excitons can accelerate the degradation of OLED materials, for example, by causing the breakage of chemical bonds in organic compounds, which is a significant factor in the performance degradation of OLED devices during operation. Given consistent bond energies, higher exciton energies are more likely to cause bond breakage. In one aspect of this invention, while meeting the requirements for luminous color, it is preferable that both the host material and the dye have low exciton energies, thereby further improving the luminous efficiency and lifetime of the device.

[0097] More preferably, in the organic electroluminescent device of the present invention, the luminescent dye accounts for 0.1%-20% of the mass percentage of the main material, for example 0.2%, 0.4%, 0.6%, 0.8%, 1%, 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, etc., preferably 0.5%-5%, and more preferably 1%-5%. Attached Figure Description

[0098] Figure 1 This is a diagram illustrating the light-emitting mechanism of the organic electroluminescent device of the present invention, wherein the FET is... Energy transfer, TTA is triplet-triplet annihilation, EL is electroluminescence.

[0099] Figure 2 This is a schematic diagram of the structure of the organic electroluminescent device prepared in the embodiments of the present invention. Detailed Implementation

[0100] Synthesis Example:

[0101] The technical solution of the present invention will be further illustrated below through specific synthetic embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention.

[0102] Example 1:

[0103]

[0104] Synthesis of Compound 2: 455 mg of N-bromosuccinimide (1.71 mmol) and 304 mg of aluminum tribromide (1.71 mmol) were weighed and added to dichloromethane (20 mL). After stirring at 0 °C for 30 minutes, a dichloromethane solution of Compound 1 (100 mg, 0.77 mmol) (20 mL) was added. After the addition was complete, the mixture was stirred overnight at 25 °C. After the reaction was complete, the mixture was filtered, and the solvent was removed under reduced pressure. The solution was then purified by column chromatography (eluent: petroleum ether: dichloromethane = 10:1) to give white solid 2 (117 mg, 53%). 1 ¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 8.07 (d, J = 7.2Hz, 2H), 7.78 (d, J = 6.8Hz, 2H), 6.60 (t, J = 7.2Hz, 2H). MS (EI) Theoretical value: C₈H₆BBr₂N: 284.90; Experimental value: 284.89 [M] + .

[0105]

[0106] Synthesis of compound 3: 1,3-Butadiene (1.05 mL, 2.09 mmol, 2.0 M in THF) and a solution of 9-boronbicyclo[3.3.1]nonane (9-BBN) (8.37 mL, 4.19 mmol, 0.5 M in THF) were added to a Shrek flask and stirred overnight at 25 °C. Compound 2 (500 mg, 1.74 mmol), palladium acetate (39.2 mg, 0.175 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (SPhos) (143 mg, 0.348 mmol), and potassium phosphate (1.11 g, 5.23 mmol) were added to another Shrek flask. The mixture was purged three times under argon protection. Tetrahydrofuran and water were added, followed by the solution that had been stirred overnight at 25 °C. The mixture was stirred and refluxed at 70 °C for 23 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The solution was then separated by column chromatography (eluent: petroleum ether) to obtain a pale yellow liquid 3 (260 mg, 82%). 1 ¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 7.66 (d, J = 6.8Hz, 2H), 7.31 (d, J = 6.4Hz, 2H), 6.57 (t, J = 6.8Hz, 2H), 2.95 (t, J = 5.6Hz, 4H), 1.94–1.90 (m, 4H). MS (EI) theoretical value: C 12 H 14 BN: 183.12; Experimental value: 183.12 [M] + .

[0107]

[0108] Synthesis of compound 4: Compound 3 (824 mg, 4.50 mmol) was weighed, purged three times under argon protection, and tetrahydrofuran (25 mL) was added. Tert-butyllithium (3.80 mL, 4.95 mmol, 1.3 M in pentane) was added dropwise at -78 °C. After stirring at 25 °C for 1 hour, 1,2-dibromoethane (1.27 g, 6.75 mmol) was added, and the mixture was stirred at 25 °C overnight. After the reaction was complete, the mixture was extracted with sodium sulfite solution and dichloromethane. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The mixture was then separated by column chromatography (eluent: petroleum ether) to give a pale yellow liquid 4 (566 mg, 48%). 1¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 8.32 (d, J = 7.2Hz, 1H), 7.35 (d, J = 6.4Hz, 1H), 7.18 (d, J = 7.2Hz, 1H), 6.98 (d, J = 6.8Hz, 1H), 6.70 (t, J = 6.8Hz, 1H), 2.98–2.90 (m, 4H), 1.92–1.88 (m, 4H). MS (EI) theoretical value: C 12 H 13 BBrN: 261.03; Experimental value: 261.03 [M] + .

[0109]

[0110] Synthesis of compound 5: Compound 4 (292 mg, 1.12 mmol), bis(triphenylphosphine)palladium dichloride (39.4 mg, 0.06 mmol), and cuprous iodide (15.0 mg, 0.08 mmol) were weighed, purged three times under argon protection, tetrahydrofuran (2 mL) was added, followed by the injection of triethylamine (2 mL) and trimethylsilylacetylene (165 mg, 1.69 mmol). The mixture was stirred and refluxed at 70 °C for 10 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The mixture was then separated by column chromatography (eluent: petroleum ether) to obtain a pale yellow liquid 5 (307 mg, 98%). 1 ¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 8.48 (d, J = 6.8Hz, 1H), 7.35 (dd, J = 6.8Hz, 1.2Hz, 1H), 7.24 (dd, J = 6.8Hz, 1.2Hz, 1H), 7.00 (d, J = 6.8Hz, 1H), 6.67 (t, J = 6.8Hz, 1H), 2.97–2.93 (m, 4H), 1.91–1.88 (m, 4H). MS (EI) theoretical value: C 17 H 22 BNSi: 279.16; Experimental value: 279.16 [M] + .

[0111]

[0112] Synthesis of compound 6: Compound 5 (307 mg, 1.10 mmol) and potassium carbonate (608 mg, 4.40 mmol) were weighed, and dichloromethane (7.3 mL) and methanol (3.6 mL) were added. The mixture was stirred at 25 °C for 3 hours. After the reaction was completed, the mixture was filtered, extracted with water and dichloromethane, and the organic layers were combined and dried with anhydrous magnesium sulfate. The mixture was filtered, evaporated to dryness, and separated by column chromatography (eluent: petroleum ether) to obtain a pale yellow liquid 6 (188 mg, 82%). 1 H NMR (400MHz, CDCl3, 297K, ppm) δ8.54(dd,J=7.2Hz,2.0Hz,1H),7.40(d,J=6.4Hz,1H),7.30(d,J=6.8Hz,1H),7.07(dd,J =6.8Hz, 2.0Hz, 1H), 6.72 (td, J = 6.8Hz, 2.0Hz, 1H), 3.64 (s, 1H), 3.00 (t, J = 3.2Hz, 4H), 1.99–1.92 (m, 4H). MS (EI) theoretical value: C 14 H 14 BN: 207.12; Experimental value: 207.12 [M] + .

[0113]

[0114] Synthesis of compound 7: Compound 6 (188 mg, 0.91 mmol) and platinum dichloride (24.2 mg, 0.09 mmol) were weighed, and the mixture was purged three times under argon protection. 1,2-Dichloroethane (10 mL) was added, and the mixture was stirred and refluxed at 125 °C for 16 hours. After the reaction was completed, water and dichloromethane were added for extraction. The organic layers were combined, dried with anhydrous magnesium sulfate, filtered, and evaporated to dryness. Column chromatography (eluent: petroleum ether) was performed to obtain a pale yellow liquid 7 (53 mg, 28%). 1 ¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 7.92 (d, J = 7.2Hz, 2H), 7.46 (d, J = 7.2Hz, 2H), 7.43 (s, 2H), 3.33–3.30 (m, 4H), 2.21–2.14 (m, 4H). MS (EI) theoretical value: C 14 H 14 BN: 207.12; Experimental value: 207.12 [M] + .

[0115]

[0116] Synthesis of compound E-1: Compound 7 (53 mg, 0.28 mmol) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (160 mg, 0.71 mmol) were weighed and added toluene. The mixture was heated and stirred at 60 °C for 9 hours. After the reaction was completed, water and dichloromethane were added for extraction. The organic layers were combined and dried with anhydrous magnesium sulfate. The mixture was filtered, evaporated to dryness, and separated by column chromatography (eluent: petroleum ether) to obtain red solid E-1 (28 mg, 54%). 1 ¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 9.14–9.09 (m, 2H), 9.02 (d, J = 8.0Hz, 2H), 8.80 (d, J = 8.0Hz, 2H), 8.37 (s, 2H), 8.08–8.02 (m, 2H). MS (EI) theoretical value: C 14 H 10 BN: 203.09; Experimental value: 203.09 [M] + .

[0117] The following describes in detail the synthetic method of borazine APD derivatives with examples. The method consists of two steps: (1) achieving five-membered ring closure through transition metal catalysis and the corresponding alkyne reaction; (2) preparing substituted borazine APD derivatives through dehydrogenation aromatization reaction.

[0118] Example 2:

[0119]

[0120] Synthesis of Compound 8: Compound 4 (130 mg, 0.50 mmol), (triphenylsilyl)acetylene (169 mg, 0.60 mmol), bis(triphenylphosphine)palladium dichloride (17.4 mg, 0.02 mmol), and triphenylphosphine (30.0 mg, 0.11 mmol) were weighed out, purged three times, and protected with argon. Benzene (1 mL) and xylene (1 mL) were added, followed by the injection of triethylamine (0.5 mL). The mixture was heated and stirred at 120 °C for 24 hours. After the reaction was complete, the mixture was extracted with water and dichloromethane. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The mixture was then separated by column chromatography (eluent: petroleum ether) to obtain the target compound 8 (180 mg, 78%) as a yellow solid. 1H NMR (400MHz, CDCl3, 297K, ppm) δ8.44(d,J=7.2Hz,1H),7.65–7.60(m,6H),7.56–7.51(m,3H),7.30–7.23(m,6H),7.18(m,1 H),7.11(d,J=6.8Hz,1H),6.98(d,J=6.8Hz,1H),6.49–6.46(m,1H),2.83–2.76(m,4H),1.77–1.71(m,4H).MS (MALDI) theoretical value: C 32 H 28 BNSi: 465.21; Experimental value: 465.21 [M] + .

[0121] Synthesis of compound E-508: Compound 8 (186 mg, 0.40 mmol) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (100 mg, 0.440 mmol) were weighed and added toluene (15 mL). The mixture was heated and stirred at 60 °C for 13 hours. After the reaction was completed, the mixture was extracted with water and dichloromethane. The organic layers were combined and dried with anhydrous magnesium sulfate. The mixture was filtered, evaporated to dryness, and separated by column chromatography (eluent was petroleum ether). The red solid E-508 (60 mg, 70%) was obtained by recrystallization from dichloromethane / methanol. 1 ¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 9.12–9.05 (m, 2H), 8.98 (d, J = 8.4Hz, 1H), 8.84 (d, J = 8.4Hz, 1H), 8.73 (d, J = 8.4Hz, 1H), 8.41 (s, 1H), 8.38 (d, J = 8.4Hz, 1H), 8.08–8.00 (m, 2H), 7.75–7.72 (m, 6H), 7.50–7.46 (m, 3H), 7.42–7.38 (m, 6H). HRMS (MALDI) theoretical values: C 32 H 24 BNSi: 461.18; Experimental value: 461.18 [M] + .

[0122] Example 3:

[0123]

[0124] Synthesis of Compound 8-1: This example is basically the same as Synthesis Example 2, except that (triphenylsilyl)acetylene needs to be replaced with an equal amount of 4-triphenylsilyl-1-butyne. The final product was the target compound, white solid 8-1 (98 mg, 40%). MS (MALDI) theoretical value: 493.24; experimental value: 493.24 [M].+ .

[0125] Synthesis of compound E-62: This example is basically the same as synthesis example 2, except that 8 needs to be replaced with an equimolar amount of 9-1. The final product was the target compound, a red solid 9-1 (117 mg, 60%). MS (MALDI) theoretical value: 489.21; experimental value: 489.21 [M]. + .

[0126] Example 4:

[0127]

[0128] Synthesis of Compound 8-2: This example is basically the same as Synthesis Example 2, except that (triphenylsilyl)acetylene needs to be replaced with an equimolar amount of 3-triphenylmethyl-1-butyne. The final product was the target compound, a white solid 8-2 (105 mg, 45%). MS (MALDI) theoretical value: 463.25; experimental value: 463.25 [M]. + .

[0129] Synthesis of compound E-70: This example is basically the same as synthesis example 2, except that 8 needs to be replaced with an equimolar amount of 8-2. The final product was the target compound, red solid E-70 (110 mg, 60%). MS (MALDI) theoretical value: 459.22; experimental value: 459.21 [M]. + .

[0130] Example 5:

[0131]

[0132] Synthesis of Compound 8-3: This example is basically the same as Synthesis Example 2, except that (triphenylsilyl)acetylene needs to be replaced with an equal amount of (tert-butyldiphenylsilyl)acetylene. The final product was the target compound, a white solid 8-3 (89 mg, 40%). MS (MALDI) theoretical value: 445.24; experimental value: 445.23 [M]. + .

[0133] Synthesis of compound E-58: This example is basically the same as synthesis example 2, except that 8 needs to be replaced with an equimolar amount of 8-3. The final product was the target compound, red solid E-58 (97 mg, 55%). MS (MALDI) theoretical value: 441.21; experimental value: 441.21 [M]. + .

[0134] Example 6:

[0135]

[0136] Synthesis of Compound 8-4: This example is basically the same as Synthesis Example 2, except that (triphenylsilyl)acetylene needs to be replaced with an equal amount of (tri-tert-butylphenylsilyl)acetylene. The final product was the target compound, a white solid 8-4 (158 mg, 50%). MS (MALDI) theoretical value: 633.40; experimental value: 633.39 [M]. + .

[0137] Synthesis of compound E-518: This example is basically the same as synthesis example 2, except that 8 needs to be replaced with an equimolar amount of 8-4. The final product was the target compound, red solid E-518 (151 mg, 60%). MS (MALDI) theoretical value: 629.36; experimental value: 629.36 [M]. + .

[0138] Example 7:

[0139]

[0140] Synthesis of Compound 8-5: This example is basically the same as Synthesis Example 2, except that (triphenylsilyl)acetylene is replaced with an equimolar amount of tris([1,1'-biphenyl]-4-yl)(acetylenyl)silane. The final product was the target compound, a white solid 8-5 (208 mg, 60%). MS (MALDI) theoretical value: 693.30; experimental value: 693.30 [M]. + .

[0141] Synthesis of compound E-545: This example is basically the same as synthesis example 2, except that 8 needs to be replaced with an equimolar amount of 8-5. The final product was the target compound, red solid E-545 (165 mg, 60%). MS (MALDI) theoretical value: 689.27; experimental value: 689.27 [M]. + .

[0142] Example 8:

[0143]

[0144] Synthesis of Compound 8-6: This example is basically the same as Synthesis Example 2, except that (triphenylsilyl)acetylene is replaced with an equimolar amount of ethynyltris(naphth-1-yl)silane. The final product was the target compound, white solid 8-6 (184 mg, 60%). MS (MALDI) theoretical value: 615.26; experimental value: 615.25 [M]. + .

[0145] Synthesis of compound E-529: This example is basically the same as synthesis example 2, except that 8 needs to be replaced with an equimolar amount of 8-6. The final product was the target compound, red solid E-529 (147 mg, 60%). MS (MALDI) theoretical value: 611.22; experimental value: 611.22 [M]. + .

[0146] Example 9:

[0147]

[0148] Synthesis of Compound 8-7: This example is basically the same as Synthesis Example 2, except that (triphenylsilyl)acetylene needs to be replaced with an equimolar amount of tris(3,5-di-tert-butylphenyl)acetylenylsilane. The final product was the target compound, a white solid 8-7 (248 mg, 62%). MS (MALDI) theoretical value: 801.58; experimental value: 801.58 [M]. + .

[0149] Synthesis of compound E-520: This example is basically the same as synthesis example 2, except that 8 needs to be replaced with an equimolar amount of 8-7. The final product was the target compound, red solid E-520 (175 mg, 55%). MS (MALDI) theoretical value: 797.55; experimental value: 797.55 [M]. + .

[0150] Example 10:

[0151]

[0152] Synthesis of Compound 10: Compound 4 (40.0 mg, 0.15 mmol), diphenylacetylene (32.0 mg, 0.18 mmol), tris(dibenzylacetone)dipalladium-chloroform adduct (15.8 mg, 0.02 mmol), tris(o-methylphenyl)phosphine (6.97 mg, 0.02 mmol), potassium acetate (44.9 mg, 0.46 mmol), and lithium chloride (6.47 mg, 0.15 mmol) were weighed out, purged three times, and protected with argon. Toluene (2 mL) and N,N-dimethylformamide (2 mL) were added, and the mixture was heated and stirred at 120 °C. After the reaction was complete, the mixture was extracted with water and dichloromethane. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The mixture was then separated by column chromatography (eluent: petroleum ether) to give a yellow solid 10 (22 mg, 40%). 1¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 7.95 (d, J = 7.2Hz, 2H), 7.49 (d, J = 7.2Hz, 2H), 7.46–7.43 (m, 4H), 7.42–7.35 (m, 6H), 3.35–3.30 (m, 4H), 2.21–2.17 (m, 4H). MS (MALDI) theoretical value: C 26 H 22 BN: 359.18; Experimental value: 359.18 [M] + Synthesis of compound E-201: Compound 10 (22 mg, 0.06 mmol) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (30 mg, 0.13 mmol) were weighed and added toluene (2 mL). The mixture was heated and stirred at 60 °C for 18 hours. After the reaction was completed, the mixture was extracted with water and dichloromethane. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The mixture was then separated by column chromatography (eluent was petroleum ether), and recrystallized from dichloromethane / methanol to give the target compound E-201 (10 mg, 47%) as a red solid. 1 ¹H NMR (400MHz, CDCl₃, 297K, ppm) δ 9.08–9.05 (m, 2H), 9.02 (d, J = 8.4Hz, 2H), 8.01 (d, J = 8.4Hz, 2H), 8.05–7.99 (m, 2H), 7.71–7.68 (m, 4H), 7.54–7.50 (m, 4H), 7.47–7.42 (m, 2H). MS (MALDI) theoretical value: C 26 H 22 BN: 355.15; Experimental value: 355.15 [M] + .

[0153] Example 11:

[0154]

[0155] Synthesis of Compound 10-1: This example is basically the same as the synthesis example 10, except that the diphenylacetylene is replaced with an equal amount of 4-tert-butylphenylacetylene. The final product was the target compound, a white solid 10-1 (24 mg, 35%). MS (MALDI) theoretical value: 471.31; experimental value: 471.30 [M]. + .

[0156] Synthesis of compound E-206: This example is basically the same as synthesis example 10, except that 10 is replaced with an equimolar amount of 10⁻¹. The final product was the target compound, red solid E-206 (17 mg, 62%). MS (MALDI) theoretical value: 467.28; experimental value: 467.27 [M]. + .

[0157] Example 12:

[0158]

[0159] Synthesis of Compound 10-2: This example is basically the same as the synthesis example 10, except that in this example, diphenylacetylene is replaced with an equimolar amount of (4-tert-butylphenyl)acetylenylbenzene. The final product is the target compound, a white solid 10-2 (28 mg, 45%). MS (MALDI) theoretical value: 415.25; experimental value: 415.25 [M]. + .

[0160] Synthesis of compound E-361: This example is basically the same as synthesis example 10, except that 10 is replaced with an equimolar amount of 10⁻². The final product was the target compound, red solid E-361 (12 mg, 50%). MS (MALDI) theoretical value: 411.22; experimental value: 411.22 [M]. + .

[0161] Example 13:

[0162]

[0163] Synthesis of Compound 10-3: This example is basically the same as the synthesis example 10, except that in this example, diphenylacetylene is replaced with an equal amount of phenylacetynyltrimethylsilane. The final product was the target compound, a white solid 10-3 (26 mg, 50%). MS (MALDI) theoretical value: 355.19; experimental value: 355.19 [M]. + .

[0164] Synthesis of compound E-345: This example is basically the same as synthesis example 10, except that 10 is replaced with an equimolar amount of 10⁻³. The final product was the target compound, red solid E-345 (12 mg, 60%). MS (MALDI) theoretical value: 351.16; experimental value: 351.16 [M]. + .

[0165] The preparation of boron-aza narrow-spectrum molecules with other substituents simply requires replacing the substituents of the reactants with the corresponding substituents, which will not be elaborated here.

[0166] Device Examples:

[0167] In OLED devices, the organic layer can be divided into multiple regions. For example, the organic layer may include a hole transport region, a light-emitting layer, and an electron transport region. The organic layer mainly includes any one or at least two combinations of a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer, or an electron injection layer.

[0168] In specific embodiments, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, thin-film transistors (TFTs) can also be incorporated into the substrate used for displays.

[0169] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0170] Organic layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. Compounds used as organic layers can be small organic molecules, large organic molecules, polymers, and combinations thereof.

[0171] The hole transport region is located between the anode and the emissive layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. Alternatively, the hole transport region can be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the emissive layer.

[0172] The material for the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, 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), aromatic amine derivatives as shown in HT-1 to HT-51 below; or any combination thereof.

[0173] The aromatic amine derivatives are compounds shown as HT-1 to HT-34 below. If the material of the hole transport region is an aromatic amine derivative, it can be one or more of the compounds shown as HT-1 to HT-34.

[0174]

[0175]

[0176]

[0177] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI-1 to HI-3 described below; it can also be one or more compounds of HT-1 to HT-34 doped with one or more compounds of HI-1 to HI-3 described below.

[0178]

[0179] The electron transport region can 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 5 can also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0180] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-57 listed below.

[0181]

[0182]

[0183]

[0184]

[0185] The structure of the light-emitting device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca.

[0186] The thickness of each of the above layers can be the conventional thickness of such layers in this field.

[0187] The following is a detailed description of the light-emitting layer. The organic light-emitting layer uses anthracene-based host material and novel boron-nitrogen heterocyclic dyes. Furthermore, the exciton energy of the host material is chosen to be greater than that of the dye (i.e., E1 > E2), while the energy difference is controlled within the range of 0.10 eV-0.30 eV. This effectively improves the device performance, resulting in an organic electroluminescent device with high luminous efficiency and long lifetime. The organic light-emitting layer is formed through a co-evaporation method.

[0188] The E1 value of the main material of the luminescent layer, the E2 value of the dye, and the E1-E2 values ​​used in the following examples and comparative examples are listed in Table 1.

[0189] serial number Main materials <![CDATA[E1(eV)]]> dye <![CDATA[E2(eV)]]> <![CDATA[E1-E2(eV)]]> 1 B-5 2.82 E-1 2.52 0.30 2 B-7 2.80 E-1 2.52 0.28 3 B-10 2.78 E-58 2.48 0.30 4 B-26 2.73 E-58 2.48 0.25 5 B-34 2.75 E-70 2.49 0.26 6 B-40 2.67 E-70 2.49 0.18 7 B-50 2.63 E-201 2.53 0.10 8 B-5 2.82 E-201 2.53 0.29 9 B-18 2.72 E-518 2.50 0.22 10 B-24 2.71 E-518 2.50 0.21 11 B-37 2.67 E-520 2.51 0.16 12 B-42 2.64 E-520 2.51 0.13 13 B-5 2.82 TBPe 2.54 0.28 14 B-5 2.82 TTPA 2.46 0.32 15 B-10 2.78 TBRb 2.40 0.38 16 B-10 2.78 DBP 2.35 0.43

[0190] The organic electroluminescent device of the present invention will be further described below through specific embodiments.

[0191] The method for preparing the organic electroluminescent device of the present invention includes the following steps:

[0192] 1. The glass plate coated with the anodic material is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixture of acetone and ethanol, baked in a clean environment until all moisture is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0193] 2. Place the glass plate with the anode inside the vacuum chamber and evacuate to a vacuum level of 1×10⁻⁶. -5 ~9×10 -3 Pa, a hole injection layer is vacuum-deposited on the above-mentioned anolyte film at a deposition rate of 0.1-0.5 nm / s;

[0194] 3. A hole transport layer is vacuum-deposited on top of the hole injection layer at a deposition rate of 0.1-0.5 nm / s.

[0195] 4. A light-emitting layer for the device is vacuum-deposited on top of the hole transport layer. The light-emitting layer includes a host material, a TADF dye, and a phosphorus photosensitizer. A multi-source co-evaporation method is used to adjust the evaporation rates of the host material, the TADF dye, and the phosphorus photosensitizer to achieve a preset doping ratio for the dye.

[0196] 5. The electron transport layer material of the device is vacuum-deposited on top of the organic light-emitting layer at a deposition rate of 0.1-0.5 nm / s;

[0197] 6. A LiF layer is vacuum-deposited at 0.1-0.5 nm / s as the electron injection layer on the electron transport layer, and an Al layer is vacuum-deposited at 0.5-1 nm / s as the cathode of the device.

[0198] The structural formulas of some organic materials used in the embodiments of this invention are as follows:

[0199]

[0200] Example 1

[0201] The device structure of this embodiment is shown below:

[0202] ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-1(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm)

[0203] In this embodiment, the anode is ITO; the hole injection layer is made of HI-2, with a total thickness of 5-30 nm, and 10 nm in this embodiment; the hole transport layer is made of HI-25, with a total thickness of 5-500 nm, and 40 nm in this embodiment; the main material of the organic light-emitting layer is a wide bandgap material B-5, and the dye is a BN heterocyclic material E-1 with a doping concentration of 1 wt%, with a thickness of 1-200 nm, and 30 nm in this embodiment; the electron transport layer is made of ET-50, with a thickness of 5-300 nm, and 30 nm in this embodiment; and the electron injection layer and cathode materials are LiF (0.5 nm) and aluminum (150 nm).

[0204] The device embodiments 1-62 and comparative examples 1-4 of the present invention were completed according to the above preparation steps and testing methods. The specific design scheme of the light-emitting layer is detailed in the following embodiments and Table 1.

[0205] Example 2

[0206] The device structure of this embodiment is shown below:

[0207] ITO / HI-2(10nm) / HT-25(40nm) / B-7:0.51wt%E-1(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm)

[0208] Its device significance is roughly the same as that of Example 1, the only difference being the main body.

[0209] Example 3

[0210] The device structure of this embodiment is shown below:

[0211] The device in ITO / HI-2(10nm) / HT-25(40nm) / B-10:0.5wt%E-1(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 1, with the only difference being the main body.

[0212] Example 4

[0213] The device structure of this embodiment is shown below:

[0214] The device in ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-1(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 1, with the only difference being the main body.

[0215] Example 5

[0216] The device structure of this embodiment is shown below:

[0217] The device in ITO / HI-2(10nm) / HT-25(40nm) / B-34:0.5wt%E-1(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 1, with the only difference being the main body.

[0218] Example 6

[0219] The device structure of this embodiment is shown below:

[0220] The device in ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-1(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 4, with the only difference being the main body.

[0221] Example 7

[0222] The device structure of this embodiment is shown below:

[0223] The device in ITO / HI-2(10nm) / HT-25(40nm) / B-50:0.5wt%E-1(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 1, with the only difference being the main body.

[0224] Example 8

[0225] The device structure of this embodiment is shown below:

[0226] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-58(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0227] Example 9

[0228] The device structure of this embodiment is shown below:

[0229] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-7:0.5wt%E-58(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 8, the only difference being the main body.

[0230] Example 10

[0231] The device structure of this embodiment is shown below:

[0232] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-10:0.5wt%E-58(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 8, the only difference being the main body.

[0233] Example 11

[0234] The device structure of this embodiment is shown below:

[0235] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-58(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 10, with the only difference being the main body.

[0236] Example 12

[0237] The device structure of this embodiment is shown below:

[0238] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-34:0.5wt%E-58(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 8, the only difference being the main body.

[0239] Example 13

[0240] The device structure of this embodiment is shown below:

[0241] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-58(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 8, the only difference being the main body.

[0242] Example 14

[0243] The device structure of this embodiment is shown below:

[0244] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-50:0.5wt%E-58(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 8, the only difference being the main body.

[0245] Example 15

[0246] The device structure of this embodiment is shown below:

[0247] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-62(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0248] Example 16

[0249] The device structure of this embodiment is shown below:

[0250] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-7:0.5wt%E-62(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 15, with the only difference being the main body.

[0251] Example 17

[0252] The device structure of this embodiment is shown below:

[0253] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-10:0.5wt%E-62(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 15, with the only difference being the main body.

[0254] Example 18

[0255] The device structure of this embodiment is shown below:

[0256] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-62(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 15, the only difference being the main body.

[0257] Example 19

[0258] The device structure of this embodiment is shown below:

[0259] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-34:0.5wt%E-62(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 51, the only difference being the main body.

[0260] Example 20

[0261] The device structure of this embodiment is shown below:

[0262] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-62(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 19, with the only difference being the main body.

[0263] Example 21

[0264] The device structure of this embodiment is shown below:

[0265] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-50:0.5wt%E-62(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 19, with the only difference being the main body.

[0266] Example 22

[0267] The device structure of this embodiment is shown below:

[0268] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-70(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0269] Example 23

[0270] The device structure of this embodiment is shown below:

[0271] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-7:0.5wt%E-70(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 22, the only difference being the main body.

[0272] Example 24

[0273] The device structure of this embodiment is shown below:

[0274] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-10:0.5wt%E-70(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 22, with the only difference being the main body.

[0275] Example 25

[0276] The device structure of this embodiment is shown below:

[0277] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-70(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 22, with the only difference being the main body.

[0278] Example 26

[0279] The device structure of this embodiment is shown below:

[0280] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-34:0.5wt%E-70(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 22, with the only difference being the main body.

[0281] Example 27

[0282] The device structure of this embodiment is shown below:

[0283] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-70(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 22, with the only difference being the main body.

[0284] Example 28

[0285] The device structure of this embodiment is shown below:

[0286] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-50:0.5wt%E-70(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 22, the only difference being the main body.

[0287] Example 29

[0288] The device structure of this embodiment is shown below:

[0289] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-201(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0290] Example 30

[0291] The device structure of this embodiment is shown below:

[0292] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-201(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 29, the only difference being the main body.

[0293] Example 31

[0294] The device structure of this embodiment is shown below:

[0295] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-201(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 29, the only difference being the main body.

[0296] Example 32

[0297] The device structure of this embodiment is shown below:

[0298] The device with the following structure is largely the same as that in Example 29: ITO / HI-2(10nm) / HT-25(40nm) / B-5:2wt%E-201(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm), except that the doping concentration of the boron-nitrogen heterocyclic fluorescent dye is different.

[0299] Example 33

[0300] The device structure of this embodiment is shown below:

[0301] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-508(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0302] Example 34

[0303] The device structure of this embodiment is shown below:

[0304] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-508(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 33, with the only difference being the main body.

[0305] Example 35

[0306] The device structure of this embodiment is shown below:

[0307] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-508(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 33, with the only difference being the main body.

[0308] Example 36

[0309] The device structure of this embodiment is shown below:

[0310] The device with the following structure is roughly the same as that in Example 33: ITO / HI-2(10nm) / HT-25(40nm) / B-5:1wt%E-508(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm), except that the doping concentration of the boron-nitrogen heterocyclic fluorescent dye is different.

[0311] Example 37

[0312] The device structure of this embodiment is shown below:

[0313] The device with ITO / HI-2 (10nm) / HT-25 (40nm) / B-5:0.5wt%E-518 (30nm) / ET-50 (30nm) / LiF (0.5nm) / Al (150nm) has a similar meaning to Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0314] Example 38

[0315] The device structure of this embodiment is shown below:

[0316] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-518(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 37, with the only difference being the main body.

[0317] Example 39

[0318] The device structure of this embodiment is shown below:

[0319] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-518(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 37, with the only difference being the main body.

[0320] Example 40

[0321] The device structure of this embodiment is shown below:

[0322] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:1.5wt%E-518(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 37, with the only difference being the different doping concentration of the resonant thermally activated delayed fluorescence material.

[0323] Example 41

[0324] The device structure of this embodiment is shown below:

[0325] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-520(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0326] Example 42

[0327] The device structure of this embodiment is shown below:

[0328] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-520(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 41, with the only difference being the main body.

[0329] Example 43

[0330] The device structure of this embodiment is shown below:

[0331] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-520(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 41, with the only difference being the main body.

[0332] Example 44

[0333] The device structure of this embodiment is shown below:

[0334] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:2.5wt%E-520(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 41, the only difference being the doping concentration of the boron-nitrogen heterocyclic fluorescent dye.

[0335] Example 45

[0336] The device structure of this embodiment is shown below:

[0337] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-529(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0338] Example 46

[0339] The device structure of this embodiment is shown below:

[0340] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-529(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 45, with the only difference being the main body.

[0341] Example 47

[0342] The device structure of this embodiment is shown below:

[0343] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-529(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 45, with the only difference being the main body.

[0344] Example 48

[0345] The device structure of this embodiment is shown below:

[0346] The device with the following structure is largely the same as that in Example 45: ITO / HI-2(10nm) / HT-25(40nm) / B-5:2wt%E-529(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm), except that the doping concentration of the boron-nitrogen heterocyclic fluorescent dye is different.

[0347] Example 49

[0348] The device structure of this embodiment is shown below:

[0349] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%E-545(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to Example 1, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0350] Example 50

[0351] The device structure of this embodiment is shown below:

[0352] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-26:0.5wt%E-545(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 49, with the only difference being the main body.

[0353] Example 51

[0354] The device structure of this embodiment is shown below:

[0355] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-40:0.5wt%E-545(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 49, with the only difference being the main body.

[0356] Example 52

[0357] The device structure of this embodiment is shown below:

[0358] The device with the following structure is largely the same as that in Example 49: ITO / HI-2(10nm) / HT-25(40nm) / B-5:5wt%E-545(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm), except that the doping concentration of the boron-nitrogen heterocyclic fluorescent dye is different.

[0359] Example 53

[0360] The device structure of this embodiment is shown below:

[0361] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-2:0.5wt%E-41(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 1, except that the main body and the types of boron-nitrogen heterocyclic fluorescent dyes are different.

[0362] Example 54

[0363] The device structure of this embodiment is shown below:

[0364] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-18:0.5wt%E-41(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 53, with the only difference being the main body.

[0365] Example 55

[0366] The device structure of this embodiment is shown below:

[0367] The device meaning of ITO / HI-2(10nm) / HT-25(40nm) / B-24:0.5wt%E-41(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) is roughly the same as that of Example 53, the only difference being the main body.

[0368] Example 56

[0369] The device structure of this embodiment is shown below:

[0370] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-2:1.5wt%E-41(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 53, the only difference being the doping concentration of the boron-nitrogen heterocyclic fluorescent dye.

[0371] Example 57

[0372] The device structure of this embodiment is shown below:

[0373] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-37:0.5wt%E-137(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 1, except that the main body and the types of boron-nitrogen heterocyclic fluorescent dyes are different.

[0374] Example 58

[0375] The device structure of this embodiment is shown below:

[0376] The device meanings of ITO / HI-2(10nm) / HT-25(40nm) / B-42:0.5wt%E-137(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) are roughly the same as those of Example 57, with the only difference being the main body.

[0377] Example 59

[0378] The device structure of this embodiment is shown below:

[0379] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-37:2.5wt%E-137(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar device meaning to Example 57, the only difference being the different doping concentration of the boron-nitrogen heterocyclic fluorescent dye.

[0380] Example 60

[0381] The device structure of this embodiment is shown below:

[0382] The device with ITO / HI-2 (10nm) / HT-25 (40nm) / B-37:0.5wt%E-206 (30nm) / ET-50 (30nm) / LiF (0.5nm) / Al (150nm) has a similar device meaning to Example 57, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0383] Example 61

[0384] The device structure of this embodiment is shown below:

[0385] The device with ITO / HI-2(10nm) / HT-25(40nm) / B-42:0.5wt%E-441(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm) has a similar meaning to that in Example 58, the only difference being the type of boron-nitrogen heterocyclic fluorescent dye.

[0386] Example 62

[0387] The device structure of this embodiment is shown below:

[0388] ITO / HI-2(10nm) / HT-25(40nm) / B-42:2.0wt%E-441(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm)

[0389] Its device significance is roughly the same as that of Example 61, the only difference being the different doping concentration of the boron-nitrogen heterocyclic fluorescent dye.

[0390] Comparative Example 1

[0391] The device structure of this comparative example is shown below:

[0392] ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%TBPe(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm)

[0393] Its device significance is roughly the same as that of Example 1, the only difference being that the light-emitting layer is replaced with a traditional fluorescent dye.

[0394] Comparative Example 2

[0395] The device structure of this comparative example is shown below:

[0396] ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%TTPA(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm)

[0397] Its device significance is roughly the same as that of Example 1, the only difference being that the light-emitting layer is replaced with a traditional fluorescent dye.

[0398] Comparative Example 3

[0399] The device structure of this comparative example is shown below:

[0400] ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%TBRb(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm)

[0401] Its device significance is roughly the same as that of Example 1, the only difference being that the light-emitting layer is replaced with a traditional fluorescent dye.

[0402] Comparative Example 4

[0403] The device structure of this comparative example is shown below:

[0404] ITO / HI-2(10nm) / HT-25(40nm) / B-5:0.5wt%DBP(30nm) / ET-50(30nm) / LiF(0.5nm) / Al(150nm)

[0405] Its device significance is roughly the same as that of Example 1, the only difference being that the light-emitting layer is replaced with a traditional fluorescent dye.

[0406] The organic electroluminescent devices prepared by the above process were subjected to the following performance measurements:

[0407] The devices prepared in Examples 1-52 and Comparative Examples 1-4 were subjected to the following performance measurements: the current, voltage, brightness, emission spectrum, current efficiency, external quantum efficiency and other characteristics of the prepared devices were tested simultaneously using a PR 655 spectral scanning luminance meter and a Keithley K 2400 digital source meter system, and the lifetime was tested using an MC-6000.

[0408] 1. Turn-on voltage: The voltage is increased at a rate of 0.1V per second, and the brightness of the organic electroluminescent device is measured when it reaches 1 cd / m². 2 The voltage at that time is the turn-on voltage;

[0409] 2. The lifetime test of LT90 is as follows: By setting different test brightness levels, the brightness and lifetime decay curves of the organic electroluminescent device are obtained, thus acquiring the lifetime value of the device at the required decay brightness. That is, the test brightness is set to 1000 cd / m². 2 Maintaining a constant current, the luminance of the organic electroluminescent device was measured to decrease to 900 cd / m². 2 Time, in hours;

[0410] The specific test results are shown in Table 2.

[0411] Table 2:

[0412]

[0413]

[0414]

[0415] The organic electroluminescent device structure of this invention exhibits an external quantum efficiency of around 10%, with a small efficiency roll-off at high brightness and a very narrow half-width, indicating good color purity. Furthermore, the device has a long lifespan, demonstrating overall superiority.

[0416] This invention also provides a display device, which includes the organic electroluminescent device as described above. Specifically, the display device can be an OLED display or other display device, as well as any product or component with display function, such as a television, digital camera, mobile phone, or tablet computer, that includes the display device. The advantages of this display device over the prior art are the same as those of the organic electroluminescent device described above, and will not be repeated here.

[0417] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some or all of the technical features therein, and these modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. An organic electroluminescent device, comprising a substrate, a first electrode, a second electrode, and an organic functional layer, wherein the organic functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes a host material and a light-emitting dye; Its features are, The energy corresponding to the highest energy emission peak in the emission spectrum of the main material is denoted as E1, and the energy corresponding to the lowest energy absorption peak in the absorption spectrum of the luminescent dye is denoted as E2. The condition is that E1 > E2, and 0.10eV ≤ E1 - E2 ≤ 0.30eV; The main material has the structure shown in Formula I: In Formula I, A and B are independently selected from one of unsubstituted or R'-substituted C6-C60 aryl groups and unsubstituted or R'-substituted C3-C60 heteroaryl groups; In Formula I, R1 and R2 independently represent substituents from a single substituent to the maximum permissible number, R 1 and R 2 Each is independently selected from one of the following: hydrogen, halogen, amino, hydroxyl, ester, cyano, nitro, unsubstituted or R'-substituted C1-C20 chain alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C1-C20 alkoxy, unsubstituted or R'-substituted C1-C20 silyl, unsubstituted or R'-substituted C1-C20 thioalkoxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl, unsubstituted or R'-substituted C6-C60 arylamino, and unsubstituted or R'-substituted C3-C60 heteroarylamino. The luminescent dye is a boron-nitrogen heterocyclic fluorescent dye with the structure shown in Formula II: In formula II, R 1 ~R 10 Each group is independently selected from hydrogen, deuterium, halogen, hydroxyl, carboxyl, nitro, cyano, sulfone, sulfoxide, alkynyl, or unsubstituted or R'-substituted groups of the following: C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkyl, C6-C30 acyl, C6-C30 amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused-ring aryl, C6-C60 aryloxy, C6-C60 arylphosphinyl, C5-C60 monocyclic heteroaryl, C5-C60 fused-ring heteroaryl, C6-C30 alkylsilyl, C6-C30 arylsilyl, or C6-C30 heteroarylsilyl. The R' is independently selected from one of deuterium, halogen, cyano, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic electroluminescent device according to claim 1, wherein in formula I, A and B are each independently selected from one of unsubstituted or R'-substituted C6-C18 aryl and unsubstituted or R'-substituted C8-C18 heteroaryl, and at least one of A and B is one of unsubstituted or R'-substituted C10-C18 fused-ring aryl and unsubstituted or R'-substituted C8-C18 fused-ring aryl; The R' is independently selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl. R1 and R2 are each independently selected from hydrogen, deuterium, or one or a combination of at least two of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethynyl, trimethylsilylethynyl, tert-butylethynyl, triisopropylsilylethynyl, phenyl, tert-butylphenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, peryl, fluoranyl, azulene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, aziridine, azobiphenyl, terphenyl, triphenyl Phenyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, indene, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, triphenylene, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl Thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, benzoindole, carbazole, benzocarbazole, indocarbazole, dibenzocarbazole, pyridinyl, bipyridinyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, benzoquinazolinyl, benzodioxacyclopentenyl, acridine, dihydroacridinyl, phenanthridine Benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthomidazoleyl, phenanthrenemidazoleyl, pyridiniumimidazolyl, pyraziniumimidazolyl, quinoxaloylimidazolyl, oxazolyl, isoxazolyl, benzoxazolyl, benzoisoxazolyl, naphthomidazoleyl, anthraquinoxazolyl, phenanthrenemidazole 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, benzoisothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, benzoquinoxalinyl, 5,10-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene 4,5,9,10-Tetraazaperyl, Pyrazinyl, Phenazinyl, Phenoxazinyl, Phenthiazinyl, Naphridinyl, Azacarbazolyl, Benzocarbazolyl, Phenanthrolinel, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Benzotriazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetrazinyl, 1,2,3,4-Tetrazinyl, 1,2,3,5-Tetrazinyl, Purinyl, Pteridyl, Indazinyl, Benzothiadiazolyl, 9,9-Dimethylacridyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrolyl, piperidinyl, methoxy, trisenel, cyclosenel, tetrastyrene, naphthimide, triphenylboryl, cycloheptanetrienyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, triphenylsilyl, dimethylphenylsilyl, diphenylmethylsilyl, or tert-butyldiphenylsilyl.

3. The organic electroluminescent device according to claim 2, wherein in formula I, A and B are each independently selected from any one of the following unsubstituted or R'-substituted groups: in, * Represents the linking site of a functional group; The R' is independently selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, and C1-C10 alkoxy; Preferably, in Formula I, A is selected from one of unsubstituted or R'-substituted naphthyl, unsubstituted or R'-substituted dibenzofuranyl, and R' is independently selected from one of deuterium, halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

4. The organic electroluminescent device according to claim 1, wherein in formula II, R 1 ~R 10 Each group is independently selected from hydrogen, deuterium, or one or more combinations of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethynyl, trimethylsilylethynyl, tert-butylethynyl, triisopropylsilylethynyl, phenyl, tert-butylphenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, pyrene, peryl, uryl, fluoranyl, azulene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azabiphenyl, azobiphenyl, terphenyl, Phenylacetyl, naphthylphenyl, phenyl terphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, indene, trimerinyl, isotrimerininyl, spirotrimerininyl, spiroisotrimerininyl, triphenylene, furanyl, benzo[a]furanyl, isobenzo[a]furanyl, dibenzo[a]furanyl, thiazolyl Fenyl, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, benzoindole, carbazole, benzocarbazole, indocarbazole, dibenzocarbazole, pyridyl, bipyridyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, benzoquinazolinyl, benzodioxanepentenyl, acridine, dihydroacridyl, phenanthridine, benzene benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthomidazoleyl, phenanthrenemidazoleyl, pyridiniumimazoleyl, pyraziniumimazoleyl, quinoxaloylimazoleyl, oxazolyl, isoxazolyl, benzoxazolyl, benzoisoxazolyl, naphthomidazoleyl, anthraquinoxazolyl, phenanthrenemidazoleyl 1,2-Thiazolyl, 1,3-Thiazolyl, benzothiazolyl, benzoisothiazolyl, pyridinyl, benzopyridinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, benzoquinoxalinyl, 5,10-diazathanel, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4 5,9,10-Tetraazaperyl, Pyrazinyl, Phenazinyl, Phenoxazinyl, Phenthiazinyl, Naphridinyl, Azacarbazolyl, Benzocarbazolyl, Phenanthrolinel, 1,2,3-Triazolyl, 1,2,4-Triazolyl, Benzotriazolyl, 1,2,3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,2,3-Thiadiazolyl 1,2,4-Thiadiazolyl, 1,2,5-Thiadiazolyl, 1,3,4-Thiadiazolyl, 1,3,5-Triazinyl, 1,2,4-Triazinyl, 1,2,3-Triazinyl, Tetrazolyl, 1,2,4,5-Tetrazinyl, 1,2,3,4-Tetrazinyl, 1,2,3,5-Tetrazinyl, Purinyl, Pteridyl, Indazinyl, Benzothiadiazolyl, 9,9-Dimethylacridyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrolyl, piperidinyl, methoxy, trisenel, cyclosenel, tetrastyrene, naphthimide, triphenylboryl, cycloheptanetrienyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, triphenylsilyl, dimethylphenylsilyl, diphenylmethylsilyl, or tert-butyldiphenylsilyl.

5. The organic electroluminescent device according to claim 1, wherein the boron-nitrogen heterocyclic fluorescent dye used as the dye has the structure shown in Formula III: In Formula III, group R 9 and R 10 The scope of the definition is the same as that in equation (2); Preferably, the R 9 R 10 Each group is independently selected from one of the following groups: in Indicates the linking site of a functional group.

6. The organic electroluminescent device according to claim 1, wherein the host material is selected from the following specific structural compounds:

7. The organic electroluminescent device according to claim 1, wherein the boron-nitrogen heterocyclic fluorescent dye used as the dye is selected from the following specific structural compounds:

8. The organic electroluminescent device according to claim 1, characterized in that, The luminescent dye accounts for 0.1%-20% of the mass percentage of the main material; Preferably, the luminescent dye accounts for 0.5%-5% of the mass percentage of the host material; more preferably, it accounts for 1%-5%.

9. The organic electroluminescent device according to claim 1 or 8, characterized in that, The organic functional layer further includes at least one of a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer, or an electron injection layer.

10. A display device, characterized in that, The display device includes the organic electroluminescent device of claim 1, wherein the display device is a display element, an illumination element, an information tag, an electronic artificial skin sheet, or electronic paper.

Images