Polar boron-nitrogen luminescent material, application thereof, and organic electroluminescent device containing the same

Abstract

The present invention relates to a compound of the general formula, belonging to the technical field of organic electroluminescence, and particularly to a multi-resonance organic compound. The compound has a structure of the following formula: #imgabs0# The electroluminescence spectrum of an OLED device prepared using the compound of the present invention has a narrow half-maximum width, showing a significant multi-resonance effect. The device also has the advantages of low starting voltage, high luminous efficiency and long life, showing good application prospects.

Description

Technical Field

[0001] The present invention relates to a general compound, belonging to the technical field of organic electroluminescence, and in particular to a multi-resonance organic compound and its application, as well as an organic electroluminescent device containing the compound. Background Art

[0002] Organic light-emitting diodes (OLEDs) are a type of device with a sandwich-like structure, consisting of positive and negative electrode layers sandwiched between layers of organic functional materials. OLEDs, due to their advantages such as high brightness, fast response, wide viewing angle, simple processing, and flexibility, have attracted considerable attention in the fields of new display and lighting technologies. Currently, this technology is widely used in display panels for new lighting fixtures, smartphones, and tablets, and is poised to expand into larger display products such as televisions. It is a rapidly developing and technologically demanding new display technology.

[0003] As OLEDs continue to advance in the fields of lighting and display, research on their core materials has become increasingly focused. This is because an efficient and long-lasting OLED device is typically the result of an optimized combination of device structure and various organic materials. To produce OLED light-emitting devices with lower driving voltages, better luminous efficiency, and longer device lifespans, and to continuously improve the performance of OLED devices, not only innovations in OLED device structure and manufacturing processes are required, but also continuous research and innovation in the optoelectronic functional materials used in OLED devices to produce functional materials with higher performance. For this reason, the OLED materials community has been committed to developing new organic electroluminescent materials to achieve low device startup voltages, high luminous efficiency, and improved device lifespans.

[0004] In the selection of OLED materials, singlet-state fluorescent materials have good lifespan and low price, but low efficiency; triplet-state phosphorescent materials have high efficiency, but are expensive, and the lifespan problem of blue light materials has not been solved. Adachi of Kyushu University in Japan proposed a new type of organic light-emitting material, namely thermally activated delayed fluorescence (TADF) material. The singlet-triplet energy gap (ΔE ST ) is very small (<0.3 eV), and triplet excitons can be converted into singlet excitons through reverse intersystem crossing (RISC) to emit light, so the internal quantum efficiency of the device can reach 100%.

[0005] The use of multiple resonance (MR) frameworks is an effective strategy for achieving high-efficiency, narrow-spectrum emission. However, given the requirements of practical applications, many challenges remain, such as complex synthesis processes, low yields, and limited molecular frameworks. Therefore, further research is needed to explore the types of narrow-band emission materials, optimize synthesis procedures, and expand material systems to accelerate the industrialization of narrow-spectrum luminescent materials. Summary of the Invention

[0006] In order to solve the above technical problems, the present invention provides a general formula compound, the specific general formula of the compound of the present invention is shown in the following formula (1):

[0007]

[0008] In formula (1), the dotted line represents connection or non-connection; Ring A, Ring B, Ring C, Ring D, Ring E and Ring F are each independently selected from one of C6-C60 aryl groups and C5-C60 heteroaryl groups;

[0009] X 2 and X 4 are independently NR1, BR2, O or S, X 1 and X 3 Each of n1, n2, n3 and n4 is independently 0 or 1;

[0010] R1 and R2 are each independently selected from unsubstituted or R x one of the following substituted groups: a C1-C36 chain alkyl group, a C3-C36 cycloalkyl group, a C1-C10 alkoxy group, a C1-C10 thioalkoxy group, a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C60 monocyclic aryl group, a C6-C60 fused-ring aryl group, a C6-C60 aryloxy group, a C5-C60 monocyclic heteroaryl group, or a C5-C60 fused-ring heteroaryl group; R1 and R2 are each independently unconnected to the adjacent ring A, ring C, ring D, or ring F, or are fused to form a ring via a single bond, an -O-, or a -S- bond;

[0011] R x One selected from the group consisting of deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 condensed-ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, and C5-C60 condensed-ring heteroaryl;

[0012] R a 、R b 、R c 、R d 、R e 、R f Each independently represents a single substituent to the maximum permissible substituent, and is independently selected from hydrogen, deuterium, or one of the following groups, which are substituted or unsubstituted: halogen, C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, adamantyl, silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 condensed ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, C5-C60 condensed ring heteroaryl; the R a 、R b 、R c and R d The adjacent two are not connected or are fused into a ring through a single bond, -O- or -S-bond;

[0013] When the above R a 、R b 、R c 、R d 、R e 、R f When substituents are present, the substituents are independently selected from one of deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 condensed ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, and C5-C60 condensed ring heteroaryl.

[0014] Furthermore, in formula (1), preferably, the ring A, ring B, ring C, ring D, ring E and ring F are each independently selected from a benzene ring, a naphthalene ring or a pyridine ring; more preferably, the ring A, ring B, ring C, ring D, ring E and ring F are all benzene rings.

[0015] Furthermore, in formula (1), preferably X 1 、X 2 、X 3 、X 4 Two of them are BR2 and the other two are NR1;

[0016] Or, X 1 、X 2 、X3 、X 4 Two of them are BR2 and the other two are O;

[0017] Or, X 1 、X 2 、X 3 、X 4 Two of them are BR2 and the other two are S;

[0018] Or, X 1 、X 2 、X 3 、X 4 Two of them are BR2, one is NR1, and the other is O;

[0019] Or, X 1 、X 2 、X 3 、X 4 One of them is BR2, two are NR1, and the other is O;

[0020] Or, X 1 、X 2 、X 3 、X 4 Two of them are NR1 and the other two are single bonds;

[0021] Or, X 1 、X 2 、X 3 、X 4 Two of them are O and the other two are single bonds.

[0022] Furthermore, the general formula compound of the present invention is represented by any one of the following formulas (2) to (4):

[0023]

[0024] In formula (2) to formula (4), X 1 、X 2 、X 3 、X 4 、R a 、R b 、R c 、R d 、R e 、R f 、R g and R x The definitions of are the same as those in formula (1); X 5 and X 6 are each independently a single bond, -O- or -S-, and n5 and n6 are each independently 0 or 1.

[0025] More preferably, in formula (2), X5 and X 6 All are single bonds, X 1 、X 3 All are single bonds;

[0026] or X 5 and X 6 All are single bonds, X 1 、X 3 All are O;

[0027] or X 5 and X 6 All are single bonds, X 1 、X 3 One is NR1 and the other is BR2;

[0028] or X 5 and X 6 All O, X 1 、X 3 All are NR1;

[0029] or X 5 and X 6 All O, X 1 、X 3 All are BR2;

[0030] More preferably, in formula (3), X 6 is a single bond, X 2 O, X 1 、X 3 All are single bonds;

[0031] or X 6 is a single bond, X 2 O, X 1 、X 3 All are O;

[0032] or X 6 is a single bond, X 2 O, X 1 、X 3 One is NR1 and the other is BR2;

[0033] or X 6 O, X 2 S, X 1 、X 3 All are NR1;

[0034] or X 6 O, X 2 S, X 1 、X 3 All are BR2;

[0035] More preferably, in formula (4), X 2 and X 4 All O, X 1 、X 3 All are single bonds;

[0036] or X 2 and X 4 All O, X 1 、X 3 All are O;

[0037] or X 2 and X 4 All O, X 1 、X 3 One is NR1 and the other is BR2;

[0038] or X 2 and X 4 All are S, X 1 、X 3 All are NR1;

[0039] or X 2 and X 4 All are S, X 1 、X 3 All are BR2.

[0040] Still further preferably, in the above general formula, the R a 、R b 、R c 、R d 、R e 、R f and R gare independently selected from hydrogen, deuterium or one of the following substituted or unsubstituted substituents: 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, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenylene, quaternaryl, fluorenyl, spirobifluorenyl, dihydro Phenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroistrimerized indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl , benzoxazolyl, naphthoxazolyl, anthraxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 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, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, silicon, or a combination of two substituents selected from the above;

[0041] When the above groups have substituents, the substituents are independently selected from any one of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy or thioalkoxy, C1-C10 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic hydrocarbon or condensed aromatic hydrocarbon group, C3-C30 monocyclic heteroaromatic hydrocarbon or condensed heteroaromatic hydrocarbon group;

[0042] More preferably, the R a 、R b 、R c 、R d 、R e 、R f and R g are independently selected from hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, tert-butyl, cyclohexyl, trifluoromethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, biphenyl, phenylene, terphenyl, triphenylene, quaternaryl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl, pyrrolyl, isoindolyl , carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthioimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, pyrimidinyl, benzopyrimidinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl azapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-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, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy or silyl.

[0043] Further preferably, in the above general formula, R1 and R2 are each independently selected from unsubstituted or R xsubstituted one of the following groups: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenyl, quadriphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroisotrimerized indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothiophene phenyl, dibenzothiophenyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzoxazolyl Thiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4- Oxadiazole, 1,2,5-oxadiazole, 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, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, or a combination of two of the above substituents;

[0044] R x One selected from the group consisting of deuterium, halogen, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C6-C30 aryloxy, and C5-C30 monocyclic heteroaryl;

[0045] More preferably, R1 and R2 are independently selected from hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, tert-butyl, cyclohexyl, trifluoromethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, biphenyl, phenylene, terphenyl, triphenylene, quaternaryl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl , pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthioimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, pyrimidinyl, benzopyrimidinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl , 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-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, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy or silyl.

[0046] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents (at least 2), they may be the same or different substituents. When the same expression is mentioned below, it has the same meaning, and the selection range of the substituents is as shown above and will not be repeated one by one.

[0047] In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following descriptions of the same elements have the same meanings.

[0048] In the present invention, unless otherwise specified, the expression of chemical elements includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1H (protium), 2H (deuterium, D), 3H (tritium, T), etc.; carbon (C) includes 12C, 13C, etc.

[0049] In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se.

[0050] In the present invention, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0051] In the present invention, the expression of Ca to Cb means that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms in the substituent.

[0052] In the present invention, “each independently” means that when there are multiple subjects, they may be the same or different.

[0053] In the present invention, the C6 to C60 can all 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.

[0054] The 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.

[0055] The C1 to C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0056] The C3 to C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0057] The C1 to C36 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C25, C28, C30, C32, C34 or C35, etc.

[0058] The C3 to C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C20, etc.

[0059] The C1 to C10 can all be C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0060] The C6 to C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0061] The C3 to C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0062] In the present invention, the C6-C60 aromatic ring, preferably a C6-C30 aromatic ring, further preferably a C6-C20 aromatic ring, includes a single aromatic ring and a condensed aromatic ring; the single aromatic ring includes a benzene ring, and the condensed aromatic ring means that the ring contains at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms to condense with each other, illustratively including but not limited to: naphthalene ring, anthracene ring, phenanthrene ring, indene ring, fluorene ring and its derivatives (9,9-dimethylfluorene ring, 9,9-diphenylfluorene ring, 9,9-dinaphthylfluorene ring, spirobifluorene ring, benzofluorene ring, etc.), fluoranthene ring, triphenylene ring, pyrene ring, perylene ring, Ring or tetracene ring, etc.

[0063] The C3-C60 heteroaromatic ring, preferably a C3-C30 heteroaromatic ring, more preferably a C3-C20 heteroaromatic ring, includes a single heteroaromatic ring or a condensed heteroaromatic ring. The single heteroaromatic ring illustratively includes, but is not limited to, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a furan ring, a thiophene ring, a pyrrole ring, and the like. The fused heteroaromatic ring means that the ring structure contains at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two share two adjacent atoms to be fused with each other, and exemplarily includes but is not limited to: quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, isobenzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring and its derivatives (N-phenylcarbazole ring, N-naphthylcarbazole ring, benzocarbazole ring, dibenzocarbazole ring, indolecarbazole ring, azacarbazole ring, etc.), acridine ring, phenothiazine ring, phenoxazine ring, hydroacridine ring, etc.

[0064] The C6-C60 aryl group, preferably a C6-C30 aryl group, further preferably a C6-C20 aryl group, includes a monocyclic aryl group and a condensed ring aryl group; the monocyclic aryl group means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are connected by a single bond, and illustratively include but are not limited to: phenyl, biphenyl, terphenyl, etc.; the condensed ring aryl group means that the group contains at least two aromatic rings, and the aromatic rings share two adjacent carbon atoms and are fused to each other, and illustratively include but are not limited to: naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylene, pyrenyl, perylene, phenyl or tetraphenyl etc.

[0065] The C3-C60 heteroaryl group, preferably a C3-C30 heteroaryl group, more preferably a C3-C20 heteroaryl group, includes a monocyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains a heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other group are connected by a single bond. Exemplary examples include but are not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, etc. The fused-ring heteroaryl group refers to a group containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) in the molecule, and the two share two adjacent atoms fused to each other, including but not limited to: quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and its derivatives (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolecarbazolyl, azacarbazolyl, etc.), acridinyl, phenothiazinyl, phenoxazinyl, hydroacridinyl, etc.

[0066] The C1-C36 chain alkyl group specifically includes a straight chain or branched chain alkyl group, preferably a C1-C20 straight chain or branched chain alkyl group, further preferably a C1-C16 straight chain or branched chain alkyl group, and further preferably a C1-C10 straight chain or branched chain alkyl group, illustratively including but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0067] The C3-C20 cycloalkyl group, preferably a C3-C10 cycloalkyl group, illustratively includes but is not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.

[0068] The C3-C20 heterocycloalkyl group is further preferably a C3-C10 heterocycloalkyl group, i.e., a group formed by replacing at least one carbon atom in the cycloalkyl group listed above with a heteroatom (such as O, S or N, etc.), illustratively including but not limited to: tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, dioxaneyl, etc.

[0069] In the present invention, the aryloxy group is a monovalent group consisting of the above-mentioned aryl group and oxygen, and the heteroaryloxy group is a monovalent group consisting of the above-mentioned heteroaryl group and oxygen.

[0070] Furthermore, the compounds of the general formula (1) of the present invention can preferably include the following specific structures, Compounds 1 to 580, which are only representative:

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] The present invention also provides an organic electroluminescent device comprising a substrate, a first electrode, a second electrode and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by any one of the above general formulas.

[0096] An embodiment of the present invention provides an organic electroluminescent device, comprising a substrate, and an anode layer, multiple light-emitting functional layers and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is formed between the hole transport layer and the electron transport layer; wherein, preferably, the light-emitting layer contains a compound of the general formula of the present invention shown in any one of the above general formulas.

[0097] The general formula compounds of the present invention (see the formula below) utilize a BN covalently doped MR resonant backbone to construct novel organic narrow-spectrum luminescent materials. The embedding of the BN bonds maintains the planar structure of the MR backbone while simultaneously imparting unique photophysical properties, such as bipolar carrier transport and intermolecular dipole-dipole interactions. Firstly, these compounds of the present invention offer advantages in synthesis, with a three-step synthesis method to obtain the target material. The borylation reaction conditions are simple, resulting in a high yield exceeding 90%. Compared with traditional borylation reactions, the compounds of the present invention are more amenable to large-scale production. Secondly, by optimizing the material structure through the use of a parent core, peripheral substituents, and fused ring parallel connections, the compounds of the present invention exhibit a fluorescence spectrum with a full width at half maximum (FWHM) of only 24-32 nm and a PLQY >90%, demonstrating high brightness.

[0098]

[0099] Specifically, ring A, ring B, ring C, ring D, ring E, and ring F in the general formula of the present invention can each be independently selected from a benzene ring, a naphthalene ring, or a pyridine ring. Although these groups have different electron-donating or electron-withdrawing abilities, when introduced into the general formula of the compound of the present invention, they significantly adjust the photophysical properties of the compound of the present invention, such as red-shift and blue-shift of absorption and emission. Since the molecular structure of the compound of the present invention has a rigid π-conjugated plane, the luminescence of the molecule mainly comes from short-range intramolecular charge transfer. Therefore, the ring AF has little effect on the half-value width and photoluminescence quantum efficiency of the compound of the present invention, and can obtain ideal photophysical properties. In combination with a more preferred embodiment, such as the X 2 and X 4 NR1, X 1 and X 3When they are all single bonds at the same time; when the peripheral groups are all carbazole groups, due to the relatively weak electron-donating ability of the carbazole group, the excited state electrons of this series of compounds are delocalized on the entire conjugated plane, and the luminescence performance and stability of the material are greatly improved. For example, another parallel scheme, X 2 and X 4 O or S, X at the same time 1 and X 3 When they are both single bonds at the same time, the heavy atom effect is introduced through the bridging of O atoms or S atoms, which improves the reverse intersystem crossing rate of the material, reduces the efficiency roll-off of the device, and improves its stability. 2 and X 4 O and NR1, X 1 and X 3 When they are both single bonds at the same time, a balance is achieved in the above two preferred structures, which not only has better luminescence performance but also reduces the efficiency roll-off of the device.

[0100] The electroluminescence spectrum of the OLED device prepared using the compound of the present invention has a narrow half-width at half maximum and exhibits a significant multiple resonance effect, thereby greatly enriching the material system of multiple resonance-thermally activated delayed fluorescence, while greatly optimizing the synthesis process and improving the reaction yield; and it has a low starting voltage, high luminous efficiency and a better service life, which can meet the current requirements of panel manufacturers for high-performance materials and show good application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0101] Figure 1 : Schematic diagram of the structure of the organic electroluminescent device prepared by the present invention, in which 1 is a substrate, 2 is an anode, 3 is a hole transport layer, 4 is an organic light-emitting layer, 5 is an electron transport layer, and 6 is a cathode. DETAILED DESCRIPTION

[0102] The specific preparation method of the above-mentioned novel compound of the present invention will be described in detail below using a plurality of synthesis examples as examples, but the preparation method of the present invention is not limited to these synthesis examples.

[0103] Various chemicals used in the present invention, such as petroleum ether, tert-butylbenzene, ethyl acetate, sodium sulfate, toluene, dichloromethane, potassium carbonate, boron tribromide, N,N-diisopropylethylamine, reaction intermediates, and other basic chemical raw materials, were purchased from Shanghai Titan Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to determine the following compounds was a ZAB-HS mass spectrometer (manufactured by Micromass, UK).

[0104] The synthesis method of the compound of the present invention is briefly described below. First, the intermediate compound (1) is obtained by a nucleophilic substitution reaction, and then a boron ester is added to obtain the intermediate (2) through a Suzuki coupling reaction. Finally, the target compound is obtained through an amino-directed electrophilic borylation reaction.

[0105]

[0106]

[0107] More specifically, the synthesis methods of representative specific compounds of the present invention are given below.

[0108] Synthesis Example

[0109] Synthesis Example 1:

[0110]

[0111] Synthesis of compound 1

[0112]

[0113] In a two-necked flask under nitrogen, compound 1-1 (1 g, 3.7 mmol) was dissolved in 30 mL of N,N-dimethylformamide. Carbazole (1.25 g, 7.5 mmol) and cesium carbonate (4.79 g, 14.7 mmol) were added, and the temperature was raised to 150°C for 16 hours. The solvent was evaporated in vacuo and the mixture was passed through a silica gel column (developing solvent: petroleum ether: CH2Cl2 = 10:1) to obtain the target compound 1-2 (1.5 g, 74% yield, 99.43% purity by HPLC) as a yellow solid.

[0114] In a two-necked flask under nitrogen, compound 1-2 (2.05 g, 3.6 mmol) was dissolved in 30 mL of a 3:1 mixture of dimethyl ether and water. Diphenylamine borate (2.56 g, 8.7 mmol), potassium carbonate (5.00 g, 36.2 mmol), and tetrakis(triphenylphosphine)palladium (0.42 g, 0.36 mmol) were added, and the mixture was heated to 80°C for 16 hours. The solvent was evaporated in vacuo and the product was passed through a silica gel column (developing solvent: petroleum ether:CH2Cl2 = 10:1) to obtain the target compound 1-3 (2.8 g, 81% yield, 99.65% purity by HPLC) as a yellow solid.

[0115] 1-3 (0.60 g, 0.8 mmol) was dissolved in 30 ml of xylene, and boron tribromide (0.81 g, 3.3 mmol) and triethylamine (0.82 g, 8.1 mmol) were added. The mixture was heated to 120°C and allowed to react for 18 hours. The solvent was evaporated in vacuo and the mixture was passed through a silica gel column (developing solvent: petroleum ether: CH₂Cl₂ = 10:1) to obtain the title compound 1 (0.35 g, 57% yield, HPLC purity 99.22%) as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 762.31. Elemental analysis: Calculated: C, 85.06; H, 4.76; B, 2.84; N, 7.35 (%); Found: C, 85.26; H, 4.62; B, 2.91; N, 7.42 (%).

[0116] Synthesis Example 2:

[0117]

[0118] Synthesis of compound 90

[0119]

[0120] This example was synthesized similarly to compound 1, except that carbazole was replaced with an equal amount of methyldiphenylamine, and diphenylamine boryl was replaced with methylcarbazole boryl. Target compound 90 (0.23 g, 38% yield, 99.55% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 870.41. Elemental analysis: Calculated: C, 85.53; H, 5.56; B, 2.48; N, 6.43 (%); Found: C, 85.46; H, 5.55; B, 2.59; N, 6.41 (%).

[0121] Synthesis Example 3:

[0122]

[0123] Synthesis of compound 3

[0124]

[0125] This example was synthesized similarly to compound 1, except that carbazole was replaced with an equal amount of diisopropyldiphenylamine, and diphenylamine borate was replaced with isopropyldiphenylamine borate. Target compound 3 (0.21 g, 25% yield, 99.65% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1098.69. Elemental analysis: Calculated: C, 85.23; H, 7.70; B, 1.97; N, 5.10 (%); Found: C, 85.36; H, 7.28; B, 1.99; N, 5.20 (%).

[0126] Synthesis Example 4:

[0127]

[0128] Synthesis of compound 28

[0129]

[0130] This example was synthesized similarly to compound 1, except that carbazole was replaced with an equal amount of tert-butylcarbazole, and diphenylamine borate was replaced with tert-butylcarbazole borate. Target compound 28 (0.31 g, 39% yield, 99.43% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1202.75. Elemental analysis: Calculated: C, 85.84; H, 7.71; B, 1.80; N, 4.66 (%); Found: C, 85.87; H, 7.73; B, 1.82; N, 4.54 (%).

[0131] Synthesis Example 5:

[0132]

[0133] Synthesis of compound 537

[0134]

[0135] This example was synthesized similarly to compound 28, except that tert-butyl carbazole borane was replaced with an equal amount of carbazole borane. Target compound 537 (0.30 g, 32% yield, 99.53% purity by HPLC) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 978.50. Elemental analysis: Calculated: C, 85.89; H, 6.18; B, 2.21; N, 5.72 (%); Found: C, 85.99; H, 6.16; B, 2.21; N, 5.75 (%).

[0136] Synthesis Example 6:

[0137]

[0138] Synthesis of compound 61

[0139]

[0140] This example is essentially the same as the synthesis of compound 1, except that the two reactants in the first two steps are kept at a 1:1 ratio, and the equivalent amount of cesium carbonate remains unchanged. Target compound 87 (0.42 g, 32% yield, 99.67% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1217.47. Elemental analysis: Calculated values: C, 88.74; H, 4.72; B, 1.77; N, 3.45; O, 1.31 (%); Found values: C, 88.77; H, 4.73; B, 1.69; N, 3.42; O, 1.38 (%).

[0141] Synthesis Example 7:

[0142]

[0143] Synthesis of compound 62

[0144]

[0145] This example is essentially the same as the synthesis of compound 61, except that the reactants shown in the figure are used instead. Target compound 62 (0.45 g, 38% yield, 99.88% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1275.77. Elemental analysis: Calculated: C, 84.69; H, 7.82; B, 1.69; N, 3.29; S, 2.51 (%); Found: C, 84.67; H, 7.88; B, 1.65; N, 3.25; S, 2.59 (%).

[0146] Synthesis Example 8:

[0147]

[0148] Synthesis of compound 97

[0149]

[0150] This example is essentially the same as the synthesis of compound 61, except that the reactants shown in the figure are used instead. Target compound 97 (0.55 g, 41% yield, 99.33% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1314.57. Elemental analysis: Calculated: C, 88.65; H, 5.29; B, 1.65; N, 3.20; O, 1.22 (%); Found: C, 88.66; H, 5.27; B, 1.69; N, 3.22; O, 1.23 (%).

[0151] Synthesis Example 9:

[0152]

[0153] Synthesis of compound 99

[0154]

[0155] This example is essentially the same as the synthesis of compound 61, except that the reactants shown in the figure are used instead. Target compound 99 (0.42 g, 36% yield, 99.54% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1182.62. Elemental analysis: Calculated: C, 77.15; H, 6.47; B, 1.83; N, 11.84; S, 2.71 (%); Found: C, 77.17; H, 6.48; B, 1.81; N, 11.81; S, 2.76 (%).

[0156] Synthesis Example 10:

[0157]

[0158] Synthesis of compound 129

[0159]

[0160] This example is essentially the same as the synthesis of compound 61, except that the reactants shown in the figure are used instead. Target compound 129 (0.52 g, 42% yield, 99.43% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1612.93. Elemental analysis: Calculated: C, 87.87; H, 7.19; B, 1.34; N, 2.61; O, 0.99 (%); Found: C, 87.85; H, 7.17; B, 1.31; N, 2.63; O, 0.99 (%).

[0161] Synthesis Example 11:

[0162]

[0163] Synthesis of compound 226

[0164]

[0165] This example is essentially the same as the synthesis of compound 61, except that the reactants shown in the figure are used instead. Target compound 226 (0.28 g, 29% yield, 99.42% purity by HPLC analysis) was obtained as a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1277.16. Elemental analysis: Calculated: C, 71.41; H, 3.55; B, 1.69; N, 3.29; S, 20.06 (%); Found: C, 71.49; H, 3.59; B, 1.62; N, 3.29; S, 20.07 (%).

[0166] Synthesis Example 12:

[0167]

[0168] Synthesis of compound 203

[0169]

[0170] This example is essentially the same as the synthesis of compound 61, except that the reactants shown in the figure are used instead. Target compound 203 (0.15 g, 19% yield, 99.62% purity by HPLC analysis) was obtained as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 1143.29. Elemental analysis: Calculated: C, 79.81; H, 3.44; B, 1.89; N, 3.67; O, 11.19 (%); Found: C, 79.86; H, 3.45; B, 1.83; N, 3.68; O, 11.12 (%).

[0171] Synthesis Example 13:

[0172]

[0173] Synthesis of compound 327

[0174]

[0175] This example is essentially the same as the synthesis of compound 1, except that the reactants shown in the figure are used instead. Target compound 327 (0.23 g, 42% yield, 99.55% purity by HPLC analysis) was obtained as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 720.16. Elemental analysis: Calculated values: C, 70.04; H, 2.80; B, 3.00; F, 15.83; N, 3.89; O, 4.44 (%); Found values: C, 70.02; H, 2.82; B, 3.04; F, 15.81; N, 3.87 (%).

[0176] Synthesis Example 14:

[0177]

[0178] Synthesis of compound 352

[0179]

[0180] This example is essentially the same as the synthesis of compound 1, except that the reactants shown in the figure are used instead. Target compound 352 (0.54 g, 62% yield, 99.45% purity by HPLC analysis) was obtained as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 1016.11. Elemental analysis: Calculated values: C, 56.73; H, 1.59; B, 2.13; F, 33.65; N, 2.76; O, 3.15 (%); Found values: C, 56.75; H, 1.55; B, 2.17; F, 33.62; N, 2.75 (%).

[0181] Synthesis Example 15:

[0182]

[0183] Synthesis of compound 336

[0184]

[0185] This example is essentially the same as the synthesis of compound 1, except that the reactants shown in the figure are used instead. Target compound 336 (0.24 g, 35% yield, 99.65% purity by HPLC analysis) was obtained as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 944.58. Elemental analysis: Calculated values: C, 83.89; H, 7.47; B, 2.29; N, 2.96; O, 3.39 (%); Found values: C, 83.83; H, 7.46; B, 2.23; N, 2.99; O, 3.37 (%).

[0186] Synthesis Example 16:

[0187]

[0188] Synthesis of compound 538

[0189]

[0190] This example is essentially the same as the synthesis of compound 61, except that the reactants shown in the figure are used instead. Target compound 538 (0.30 g, 33% yield, 99.21% purity by HPLC analysis) was obtained as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 961.53. Elemental analysis: Calculated: C, 84.91; H, 6.81; B, 2.25; N, 4.37; O, 1.66 (%); Found: C, 84.93; H, 6.83; B, 2.24; N, 4.39; O, 1.63 (%).

[0191] Synthesis Example 17:

[0192]

[0193] Synthesis of compound 386

[0194]

[0195] This example is essentially the same as the synthesis of compound 1, except that the reactants shown in the figure are used instead. Target compound 386 (0.12 g, 13% yield, 99.12% purity by HPLC analysis) was obtained as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 1102.3. Elemental analysis: Calculated values: C, 78.41; H, 3.66; B, 1.96; N, 10.16; S, 5.81 (%); Found values: C, 78.48; H, 3.68; B, 1.98; N, 10.19; S, 5.88 (%).

[0196] Synthesis Example 18:

[0197]

[0198] Synthesis of compound 539

[0199]

[0200] This example is essentially the same as the synthesis of compound 1, except that the reactants shown in the figure are used instead. 539-4 is obtained, then dissolved in 30 ml of dichloromethane. Trifluoromethanesulfonic acid and dichlorodicyanobenzoquinone are added to yield 539. Target compound 539 (0.32 g, 47% yield, 99.47% purity by HPLC analysis) is obtained as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 754.25. Elemental analysis: Calculated: C, 85.97; H, 3.74; B, 2.87; N, 7.43 (%); Found: C, 85.97; H, 3.72; B, 2.86; N, 7.43 (%).

[0201] Synthesis Example 19:

[0202]

[0203] Synthesis of compound 540

[0204]

[0205] This example was synthesized essentially the same way as compound 539, except that the reactants shown in the diagram were used instead. Target compound 540 (0.22 g, 27% yield, 99.89% purity by HPLC analysis) was obtained as an orange-red solid. MALDI-TOF-MS results: Molecular ion peak: 866.38. Elemental analysis: Calculated: C, 85.92; H, 5.12; B, 2.49; N, 6.46 (%); Found: C, 85.92; H, 5.12; B, 2.45; N, 6.41 (%).

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] The technical effects and advantages of the present invention are demonstrated and verified by applying the compound of the present invention to an organic electroluminescent device to test its actual performance.

[0221] An organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer located between the two electrodes. The organic material layer can be divided into multiple regions, for example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0222] The anode material can be made of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), and any combination thereof. The cathode material can be made of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof.

[0223] The hole transport region is located between the anode and the light-emitting 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. The hole transport region can also be a multilayer structure comprising at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0224] The material of the hole transport region can be selected from but 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, etc.

[0225] The light-emitting layer includes a luminescent dye (i.e., a dopant) that can emit light at different wavelengths, and may also include a host material. The light-emitting layer can be a monochromatic light-emitting layer that emits a single color, such as red, green, or blue. Multiple monochromatic light-emitting layers of different colors can be arranged in a planar pattern according to a pixel pattern, or they can be stacked together to form a multi-color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single-color light-emitting layer that can simultaneously emit different colors, such as red, green, and blue.

[0226] 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 can also be a multi-layer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0227] Combined with attachment Figure 1 The process for preparing an organic electroluminescent device is as follows: an anode 2, a hole transport layer 3, an organic light-emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on a substrate 1, followed by encapsulation. The organic light-emitting layer 4 is formed by co-evaporation of a wide bandgap material source, an electron donor material source, an electron acceptor material source, and a resonant TADF material source.

[0228] Specifically, the method for preparing an organic electroluminescent device of the present invention comprises the following steps:

[0229] 1. The glass plate coated with the anode material was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in an acetone:ethanol mixed solvent, baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0230] 2. Place the glass plate with the anode in a vacuum chamber and evacuate to 1×10 -5 ~9×10 -3 Pa, vacuum evaporating a hole injection material on the anode layer to form a hole injection layer at a rate of 0.1-0.5 nm / s;

[0231] 3. Vacuum evaporate the hole transport material on the hole injection layer to form a hole transport layer at a rate of 0.1-0.5 nm / s.

[0232] 4. Vacuum evaporate the electron blocking layer on the hole transport layer at a rate of 0.1-0.5 nm / s;

[0233] 5. Vacuum-depositing the organic light-emitting layer of the device on the electron blocking layer. The organic light-emitting layer materials include a host material and a TADF dye. Using a multi-source co-evaporation method, the evaporation rate of the host material, the evaporation rate of the sensitizer material, and the evaporation rate of the dye are adjusted to achieve a preset doping ratio of the dye.

[0234] 6. Vacuum-deposit a hole blocking layer on the organic light-emitting layer at a rate of 0.1-0.5 nm / s;

[0235] 7. Vacuum evaporating the electron transport material of the device on the hole blocking layer to form an electron transport layer at a rate of 0.1-0.5 nm / s;

[0236] 8. LiF was vacuum evaporated at 0.1-0.5 nm / s on the electron transport layer as the electron injection layer, and Al was vacuum evaporated at 0.5-1 nm / s as the cathode of the device.

[0237] An embodiment of the present invention further provides a display device comprising the organic electroluminescent device described above. Specifically, the display device may be an OLED display, or any other display-capable product or component incorporating the display device, such as a television, digital camera, mobile phone, or tablet computer. The advantages of this display device over existing technologies are the same as those of the organic electroluminescent device described above, and are not further elaborated here.

[0238] The organic electroluminescent device of the present invention is further described below through specific examples.

[0239] Device Example 1

[0240] The structure of the organic electroluminescent device prepared in this embodiment is as follows:

[0241] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%1(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0242] Among them, the anode material is ITO; the hole injection layer material is HI, the total thickness is generally 5-30nm, and the present embodiment is 10nm; the hole transport layer material is HT, the total thickness is generally 5-500nm, and the present embodiment is 40nm; Host is the main material of the organic light-emitting layer with a wide band gap, the compound 1 of the present invention is a dye and the doping concentration is 3wt%, the thickness of the organic light-emitting layer is generally 1-200nm, and the present embodiment is 30nm; the electron transport layer material is ET, the thickness is generally 5-300nm, and the present embodiment is 30nm; LiF (0.5nm) and metal aluminum (150nm) are selected as the electron injection layer and cathode materials.

[0243] A DC voltage was applied to the organic electroluminescent device D1 prepared in this example, and the luminous flux of 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 566nm, a half-maximum width of 29nm, CIE color coordinates (x, y) = (0.51, 0.55), and an external quantum efficiency EQE of 31.7% (driving voltage is 2.5V).

[0244] Device Example 2

[0245] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 7. The specific device structure is as follows:

[0246] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%7(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0247] The device performance of the organic electroluminescent device D2 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 566 nm, a half-peak width of 29 nm, CIE color coordinates (x, y) = (0.43, 0.55), and an external quantum efficiency EQE of 34.8% (driving voltage is 2.7 V).

[0248] Device Example 3

[0249] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 12. The device structure is as follows:

[0250] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%12(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0251] The device performance of the organic electroluminescent device D3 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 549nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.23, 0.57), and an external quantum efficiency EQE of 32.9% (driving voltage is 2.5V).

[0252] Device Example 4

[0253] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 18. The device structure is as follows:

[0254] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%18(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0255] The device performance of the organic electroluminescent device D4 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 502nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.27, 0.72), and an external quantum efficiency EQE of 36.4% (driving voltage is 2.6V).

[0256] Device Example 5

[0257] The preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced by 25 instead of 1. The device structure is as follows:

[0258] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%25(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0259] The performance of the organic electroluminescent device D5 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 522nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.31, 0.69), and an external quantum efficiency EQE of 33.4% (driving voltage is 2.6V).

[0260] Device Example 6

[0261] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 32 instead of 1. The device structure is as follows:

[0262] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%32(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0263] The performance of the organic electroluminescent device D6 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m2 The characteristics of the light emission are green light with a wavelength of 516 nm, a half-peak width of 26 nm, CIE color coordinates (x, y) = (0.20, 0.67), and an external quantum efficiency EQE of 34.0% (driving voltage is 2.6 V).

[0264] Device Example 7

[0265] The preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced by 40. The device structure is as follows:

[0266] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%40(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0267] The performance of the organic electroluminescent device D7 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 520nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.17, 0.63), and an external quantum efficiency EQE of 38.5% (driving voltage is 2.6V).

[0268] Device Example 8

[0269] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 46. The device structure is as follows:

[0270] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%46(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0271] The performance of the organic electroluminescent device D8 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 553nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.48, 0.53), and an external quantum efficiency EQE of 34.1% (driving voltage is 2.5V).

[0272] Device Example 9

[0273] The preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced by 52. ​​The device structure is as follows:

[0274] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%52(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0275] The performance of the organic electroluminescent device D9 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 545nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.23, 0.64), and an external quantum efficiency EQE of 38.6% (driving voltage is 2.6V).

[0276] Device Example 10

[0277] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 59. The device structure is as follows:

[0278] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%59(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0279] The performance of the organic electroluminescent device D10 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 551nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.55, 0.59), and an external quantum efficiency EQE of 33.4% (driving voltage is 2.7V).

[0280] Device Example 11

[0281] The preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced by 67. The device structure is as follows:

[0282] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%67(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0283] The performance of the organic electroluminescent device D11 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2The characteristics of light emission are green light with a wavelength of 516nm, a half-peak width of 29nm, CIE color coordinates (x, y) = (0.27, 0.58), and an external quantum efficiency EQE of 34.2% (driving voltage is 2.7V).

[0284] Device Example 12

[0285] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 73. The device structure is as follows:

[0286] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%73(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0287] The device performance of the organic electroluminescent device D12 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 499nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.15, 0.26), and an external quantum efficiency EQE of 31.5% (driving voltage is 2.6V).

[0288] Device Example 13

[0289] The preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced by 80. The device structure is as follows:

[0290] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%80(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0291] The device performance of the organic electroluminescent device D13 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 562nm, a half-maximum width of 30nm, CIE color coordinates (x, y) = (0.57, 0.43), and an external quantum efficiency EQE of 30.2% (driving voltage is 2.6V).

[0292] Device Example 14

[0293] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 87. The device structure is as follows:

[0294] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%87(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0295] The device performance of the organic electroluminescent device D14 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 529nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.21, 0.56), and an external quantum efficiency EQE of 34.8% (driving voltage is 2.6V).

[0296] Device Example 15

[0297] The preparation method is the same as that of device example 1, except that the dye in the light-emitting layer is replaced by 93 instead of 1. The device structure is as follows:

[0298] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%93(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0299] The device performance of the organic electroluminescent device D15 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 499 nm, a half-peak width of 25 nm, CIE color coordinates (x, y) = (0.12, 0.09), and an external quantum efficiency EQE of 40.4% (driving voltage is 2.7 V).

[0300] Device Example 16

[0301] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 99 instead of 1. The device structure is as follows:

[0302] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%99(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0303] The performance of the organic electroluminescent device D16 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2The characteristics of the light emission are green light with a wavelength of 520nm, a half-peak width of 29nm, CIE color coordinates (x, y) = (0.19, 0.62), and an external quantum efficiency EQE of 37.4% (driving voltage is 2.7V).

[0304] Device Example 17

[0305] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 105. The device structure is as follows:

[0306] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%105(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0307] The device performance of the organic electroluminescent device D17 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow light with a wavelength of 572nm, a half-peak width of 29nm, CIE color coordinates (x, y) = (0.58, 0.48), and an external quantum efficiency EQE of 40.7% (driving voltage is 2.6V).

[0308] Device Example 18

[0309] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 110. The device structure is as follows:

[0310] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%110(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0311] The device performance of the organic electroluminescent device D18 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 491nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.13, 0.15), and an external quantum efficiency EQE of 30.7% (driving voltage is 2.5V).

[0312] Device Example 19

[0313] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 116. The device structure is as follows:

[0314] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%116(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0315] The performance of the organic electroluminescent device D19 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 515nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.28, 0.60), and an external quantum efficiency EQE of 33.9% (driving voltage is 2.6V).

[0316] Device Example 20

[0317] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 123. The device structure is as follows:

[0318] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%123(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0319] The device performance of the organic electroluminescent device D20 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 510nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.24, 0.58), and an external quantum efficiency EQE of 37.9% (driving voltage is 2.6V).

[0320] Device Example 21

[0321] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 130. The device structure is as follows:

[0322] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%130(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0323] The device performance of the organic electroluminescent device D21 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are yellow-green light emission with a wavelength of 550nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.42, 0.49), and an external quantum efficiency EQE of 36.0% (driving voltage is 2.6V).

[0324] Device Example 22

[0325] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 136. The device structure is as follows:

[0326] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%136(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0327] The device performance of the organic electroluminescent device D22 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 517nm, a half-maximum width of 27nm, CIE color coordinates (x, y) = (0.23, 0.57), and an external quantum efficiency EQE of 31.4% (driving voltage is 2.6V).

[0328] Device Example 23

[0329] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 142. The device structure is as follows:

[0330] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%142(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0331] The device performance of the organic electroluminescent device D23 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 527nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.22, 0.59), and an external quantum efficiency EQE of 33.6% (driving voltage is 2.7V).

[0332] Device Example 24

[0333] The preparation method is the same as that of device Example 1, except that the dye used in the light-emitting layer is replaced by 150. The device structure is as follows:

[0334] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%150(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0335] The device performance of the organic electroluminescent device D24 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 545nm, a half-maximum width of 29nm, CIE color coordinates (x, y) = (0.18, 0.66), and an external quantum efficiency EQE of 33.1% (driving voltage is 2.6V).

[0336] Device Example 25

[0337] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 156. The device structure is as follows:

[0338] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%156(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0339] The device performance of the organic electroluminescent device D25 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 491nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.13, 0.12), and an external quantum efficiency EQE of 32.8% (driving voltage is 2.6V).

[0340] Device Example 26

[0341] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 162. The device structure is as follows:

[0342] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%162(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0343] The performance of the organic electroluminescent device D26 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2The characteristics of the light emission are blue light emission with a wavelength of 456nm, a half-maximum width of 26nm, CIE color coordinates (x, y) = (0.13, 0.09), and an external quantum efficiency EQE of 32.8% (driving voltage is 2.7V).

[0344] Device Example 27

[0345] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 168. The device structure is as follows:

[0346] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%168(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0347] The device performance of the organic electroluminescent device D27 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 553nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.15, 0.62), and an external quantum efficiency EQE of 32.8% (driving voltage is 2.6V).

[0348] Device Example 28

[0349] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 174. The device structure is as follows:

[0350] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%174(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0351] The device performance of the organic electroluminescent device D28 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 538nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.21, 0.67), and an external quantum efficiency EQE of 34.2% (driving voltage is 2.6V).

[0352] Device Example 29

[0353] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 180. The device structure is as follows:

[0354] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%180(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0355] The device performance of the organic electroluminescent device D29 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 518nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.23, 0.59), and an external quantum efficiency EQE of 31.7% (driving voltage is 2.6V).

[0356] Device Example 30

[0357] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 188. The device structure is as follows:

[0358] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%188(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0359] The D30 performance of the organic electroluminescent device prepared in this example is as follows: DC voltage is applied and the D30 of the device is measured at 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 547nm, a half-peak width of 29nm, CIE color coordinates (x, y) = (0.15, 0.66), and an external quantum efficiency EQE of 33.9% (driving voltage is 2.7V).

[0360] Device Example 31

[0361] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 192. The device structure is as follows:

[0362] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%192(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0363] The device performance of the organic electroluminescent device D31 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are blue light emission with a wavelength of 488nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.13, 0.09), and an external quantum efficiency EQE of 36.8% (driving voltage is 2.5V).

[0364] Device Example 32

[0365] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 198. The device structure is as follows:

[0366] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%198(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0367] The device performance of the organic electroluminescent device D32 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 490nm, a half-maximum width of 30nm, CIE color coordinates (x, y) = (0.14, 0.21), and an external quantum efficiency EQE of 30.7% (driving voltage is 2.6V).

[0368] Device Example 33

[0369] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 203. The device structure is as follows:

[0370] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%203(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0371] The device performance of the organic electroluminescent device D33 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 561nm, a half-peak width of 29nm, CIE color coordinates (x, y) = (0.49, 0.51), and an external quantum efficiency EQE of 37.5% (driving voltage is 2.5V).

[0372] Device Example 34

[0373] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 209. The device structure is as follows:

[0374] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%209(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0375] The device performance of the organic electroluminescent device D34 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow light emission with a wavelength of 577 nm, a half-peak width of 27 nm, CIE color coordinates (x, y) = (0.44, 0.62), and an external quantum efficiency EQE of 37.9% (driving voltage 2.5 V).

[0376] Device Example 35

[0377] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 215. The device structure is as follows:

[0378] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%215(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0379] The device performance of the organic electroluminescent device D35 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 463 nm, a half-peak width of 29 nm, CIE color coordinates (x, y) = (0.13, 0.10), and an external quantum efficiency EQE of 39.2% (driving voltage is 2.7 V).

[0380] Device Example 36

[0381] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 220. The device structure is as follows:

[0382] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%220(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0383] The device performance of the organic electroluminescent device D36 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are green light with a wavelength of 548 nm, a half-maximum width of 29 nm, CIE color coordinates (x, y) = (0.19, 0.70), and an external quantum efficiency EQE of 34.0% (driving voltage is 2.5 V).

[0384] Device Example 37

[0385] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 226. The device structure is as follows:

[0386] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%226(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0387] The device performance of the organic electroluminescent device D37 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 564nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.34, 0.52), and an external quantum efficiency EQE of 32.5% (driving voltage is 2.7V).

[0388] Device Example 38

[0389] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 232. The device structure is as follows:

[0390] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%232(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0391] The device performance of the organic electroluminescent device D38 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 536nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.21, 0.72), and an external quantum efficiency EQE of 30.8% (driving voltage is 2.7V).

[0392] Device Example 39

[0393] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 236. The device structure is as follows:

[0394] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%236(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0395] The device performance of the organic electroluminescent device D39 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 539nm, a half-maximum width of 29nm, CIE color coordinates (x, y) = (0.21, 0.67), and an external quantum efficiency EQE of 31.3% (driving voltage is 2.7V).

[0396] Device Example 40

[0397] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 242. The device structure is as follows:

[0398] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%242(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0399] The performance results of the organic electroluminescent device D40 prepared in this example are as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 470nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.12, 0.08), and an external quantum efficiency EQE of 38.7% (driving voltage is 2.5V).

[0400] Device Example 41

[0401] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 248. The device structure is as follows:

[0402] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%248(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0403] The device performance of the organic electroluminescent device D41 prepared in this example is as follows: DC voltage is applied and the luminous flux of 10 cd / m 2The characteristics of the light emission are yellow-green light emission with a wavelength of 565nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.29, 0.57), and an external quantum efficiency EQE of 31.8% (driving voltage is 2.5V).

[0404] Device Example 42

[0405] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 257. The device structure is as follows:

[0406] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%257(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0407] The device performance of the organic electroluminescent device D42 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 541 nm, a half-peak width of 25 nm, CIE color coordinates (x, y) = (0.24, 0.72), and an external quantum efficiency EQE of 40.5% (driving voltage is 2.5 V).

[0408] Device Example 43

[0409] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 263. The device structure is as follows:

[0410] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%263(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0411] The device performance of the organic electroluminescent device D43 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 483nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.13, 0.10), and an external quantum efficiency EQE of 38.2% (driving voltage is 2.6V).

[0412] Device Example 44

[0413] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 270. The device structure is as follows:

[0414] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%270(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0415] The device performance of the organic electroluminescent device D44 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow light emission with a wavelength of 578 nm, a half-peak width of 29 nm, CIE color coordinates (x, y) = (0.62, 0.30), and an external quantum efficiency EQE of 31.0% (driving voltage 2.7 V).

[0416] Device Example 45

[0417] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 276. The device structure is as follows:

[0418] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%276(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0419] The performance of the organic electroluminescent device D45 prepared in this example was measured as follows: a DC voltage was applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 552nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.24, 0.64), and an external quantum efficiency EQE of 35.1% (driving voltage is 2.5V).

[0420] Device Example 46

[0421] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 283. The device structure is as follows:

[0422] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%283(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0423] The device performance of the organic electroluminescent device D46 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are blue light emission with a wavelength of 460nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.12, 0.09), and an external quantum efficiency EQE of 39.3% (driving voltage is 2.7V).

[0424] Device Example 47

[0425] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 290. The device structure is as follows:

[0426] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%290(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0427] The device performance of the organic electroluminescent device D47 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 567nm, a half-maximum width of 30nm, CIE color coordinates (x, y) = (0.44, 0.60), and an external quantum efficiency EQE of 37.8% (driving voltage is 2.7V).

[0428] Device Example 48

[0429] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 296. The device structure is as follows:

[0430] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%296(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0431] The performance of the organic electroluminescent device D48 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 521nm, a half-maximum width of 27nm, CIE color coordinates (x, y) = (0.24, 0.69), and an external quantum efficiency EQE of 32.1% (driving voltage is 2.7V).

[0432] Device Example 49

[0433] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 302. The device structure is as follows:

[0434] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%302(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0435] The performance of the organic electroluminescent device D49 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 520nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.23, 0.67), and an external quantum efficiency EQE of 37.1% (driving voltage is 2.6V).

[0436] Device Example 50

[0437] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 306. The device structure is as follows:

[0438] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%306(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0439] The D50 performance of the organic electroluminescent device prepared in this example is as follows: DC voltage is applied and the D50 of 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 556nm, a half-maximum width of 30nm, CIE color coordinates (x, y) = (0.46, 0.59), and an external quantum efficiency EQE of 32.4% (driving voltage is 2.5V).

[0440] Device Example 51

[0441] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 312. The device structure is as follows:

[0442] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%312(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0443] The device performance of the organic electroluminescent device D51 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are yellow-green light emission with a wavelength of 550nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.40, 0.57), and an external quantum efficiency EQE of 31.2% (driving voltage is 2.6V).

[0444] Device Example 52

[0445] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 318. The device structure is as follows:

[0446] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%318(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0447] The performance of the organic electroluminescent device D52 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 508 nm, a half-maximum width of 27 nm, CIE color coordinates (x, y) = (0.20, 0.64), and an external quantum efficiency EQE of 33.0% (driving voltage is 2.6 V).

[0448] Device Example 53

[0449] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 320. The device structure is as follows:

[0450] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%320(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0451] The device performance of the organic electroluminescent device D53 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 472nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.12, 0.07), and an external quantum efficiency EQE of 40.3% (driving voltage is 2.5V).

[0452] Device Example 54

[0453] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 325 instead of 1. The device structure is as follows:

[0454] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%325(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0455] The device performance of the organic electroluminescent device D54 prepared in this example is as follows: DC voltage is applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 563nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.30, 0.62), and an external quantum efficiency EQE of 32.7% (driving voltage is 2.5V).

[0456] Device Example 55

[0457] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 331. The device structure is as follows:

[0458] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%331(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0459] The D55 performance of the organic electroluminescent device prepared in this example is as follows: DC voltage is applied and the D55 of the 10 cd / m 2 The characteristics of the light emission are yellow light with a wavelength of 573nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.59, 0.37), and an external quantum efficiency EQE of 37.1% (driving voltage is 2.5V).

[0460] Device Example 56

[0461] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 336. The device structure is as follows:

[0462] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%336(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0463] The performance of the organic electroluminescent device D56 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2The characteristics of the light emission are green light with a wavelength of 494nm, a half-peak width of 24nm, CIE color coordinates (x, y) = (0.17, 0.52), and an external quantum efficiency EQE of 29.2% (driving voltage is 2.5V).

[0464] Device Example 57

[0465] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 343. The device structure is as follows:

[0466] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%343(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0467] The performance of the organic electroluminescent device D57 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 576 nm, a half-peak width of 25 nm, CIE color coordinates (x, y) = (0.45, 0.54), and an external quantum efficiency EQE of 39.0% (driving voltage 2.7 V).

[0468] Device Example 58

[0469] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 350 instead of 1. The device structure is as follows:

[0470] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%350(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0471] The performance of the organic electroluminescent device D58 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 560nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.460, 0.44), and an external quantum efficiency EQE of 34.6% (driving voltage is 2.5V).

[0472] Device Example 59

[0473] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 357. The device structure is as follows:

[0474] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%357(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0475] The performance of the organic electroluminescent device D59 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 484nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.13, 0.12), and an external quantum efficiency EQE of 32.8% (driving voltage is 2.5V).

[0476] Device Example 60

[0477] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 363. The device structure is as follows:

[0478] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%363(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0479] The D60 performance of the organic electroluminescent device prepared in this example is as follows: DC voltage is applied and the D60 of the device is measured at 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 469nm, a half-maximum width of 28nm, CIE color coordinates (x, y) = (0.14, 0.16), and an external quantum efficiency EQE of 39.3% (driving voltage is 2.6V).

[0480] Device Example 61

[0481] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 369 instead of 1. The device structure is as follows:

[0482] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%369(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0483] The device performance of the organic electroluminescent device D61 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are green light with a wavelength of 528 nm, a half-peak width of 29 nm, CIE color coordinates (x, y) = (0.24, 0.67), and an external quantum efficiency EQE of 35.0% (driving voltage is 2.5 V).

[0484] Device Example 62

[0485] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 375 instead of 1. The device structure is as follows:

[0486] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%375(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0487] The device performance of the organic electroluminescent device D62 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 508nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.18, 0.64), and an external quantum efficiency EQE of 36.8% (driving voltage is 2.7V).

[0488] Device Example 63

[0489] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 381. The device structure is as follows:

[0490] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%381(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0491] The device performance of the organic electroluminescent device D63 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 494nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.15, 0.06), and an external quantum efficiency EQE of 36.4% (driving voltage is 2.5V).

[0492] Device Example 64

[0493] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 387. The device structure is as follows:

[0494] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%387(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0495] The device performance of the organic electroluminescent device D64 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 474nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.13, 0.10), and an external quantum efficiency EQE of 38.5% (driving voltage is 2.7V).

[0496] Device Example 65

[0497] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 394. The device structure is as follows:

[0498] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%394(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0499] The performance results of the organic electroluminescent device D65 prepared in this example are as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 506nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.21, 0.64), and an external quantum efficiency EQE of 34.3% (driving voltage is 2.6V).

[0500] Device Example 66

[0501] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 400. The device structure is as follows:

[0502] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%400(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0503] The performance of the organic electroluminescent device D66 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2The characteristics of the light emission are blue light emission with a wavelength of 459nm, a half-maximum width of 27nm, CIE color coordinates (x, y) = (0.13, 0.09), and an external quantum efficiency EQE of 39.6% (driving voltage is 2.7V).

[0504] Device Example 67

[0505] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 405. The device structure is as follows:

[0506] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%405(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0507] The performance of the organic electroluminescent device D67 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 455nm, a half-maximum width of 28nm, CIE color coordinates (x, y) = (0.13, 0.07), and an external quantum efficiency EQE of 33.1% (driving voltage is 2.7V).

[0508] Device Example 68

[0509] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 410. The device structure is as follows:

[0510] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%410(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0511] The performance of the organic electroluminescent device D68 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 451nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.14, 0.09), and an external quantum efficiency EQE of 39.2% (driving voltage is 2.5V).

[0512] Device Example 69

[0513] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 416. The device structure is as follows:

[0514] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%416(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0515] The performance of the organic electroluminescent device D69 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 548nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.24, 0.66), and an external quantum efficiency EQE of 37.2% (driving voltage is 2.7V).

[0516] Device Example 70

[0517] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 422. The device structure is as follows:

[0518] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%422(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0519] The D70 performance of the organic electroluminescent device prepared in this example is as follows: DC voltage is applied and the D70 of the device is measured at 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 542nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.24, 0.66), and an external quantum efficiency EQE of 37.8% (driving voltage is 2.5V).

[0520] Device Example 71

[0521] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 428. The device structure is as follows:

[0522] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%428(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0523] The performance of the organic electroluminescent device D71 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2The characteristics of the light emission are green light with a wavelength of 535nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.24, 0.62), and an external quantum efficiency EQE of 31.4% (driving voltage is 2.6V).

[0524] Device Example 72

[0525] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 432. The device structure is as follows:

[0526] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%432(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0527] The device performance of the organic electroluminescent device D72 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow light emission with a wavelength of 578 nm, a half-peak width of 25 nm, CIE color coordinates (x, y) = (0.45, 0.44), and an external quantum efficiency EQE of 38.5% (driving voltage 2.7 V).

[0528] Device Example 73

[0529] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 438. The device structure is as follows:

[0530] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%438(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0531] The device performance of the organic electroluminescent device D73 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 490nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.13, 0.12), and an external quantum efficiency EQE of 32.1% (driving voltage is 2.7V).

[0532] Device Example 74

[0533] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 442. The device structure is as follows:

[0534] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%442(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0535] The device performance of the organic electroluminescent device D74 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 532nm, a half-maximum width of 27nm, CIE color coordinates (x, y) = (0.21, 0.65), and an external quantum efficiency EQE of 31.7% (driving voltage is 2.6V).

[0536] Device Example 75

[0537] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 450. The device structure is as follows:

[0538] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%450(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0539] The performance results of the organic electroluminescent device D75 prepared in this example are as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 492nm, a half-peak width of 29nm, CIE color coordinates (x, y) = (0.15, 0.21), and an external quantum efficiency EQE of 34.3% (driving voltage is 2.6V).

[0540] Device Example 76

[0541] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 456. The device structure is as follows:

[0542] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%456(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0543] The device performance of the organic electroluminescent device D76 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are green light with a wavelength of 543nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.24, 0.69), and an external quantum efficiency EQE of 36.6% (driving voltage is 2.5V).

[0544] Device Example 77

[0545] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 463. The device structure is as follows:

[0546] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%463(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0547] The device performance of the organic electroluminescent device D77 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 560nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.46, 0.57), and an external quantum efficiency EQE of 40.5% (driving voltage is 2.6V).

[0548] Device Example 78

[0549] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 469. The device structure is as follows:

[0550] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%469(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0551] The performance of the organic electroluminescent device D78 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 526 nm, a half-peak width of 27 nm, CIE color coordinates (x, y) = (0.26, 0.57), and an external quantum efficiency EQE of 38.0% (driving voltage is 2.5 V).

[0552] Device Example 79

[0553] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 475. The device structure is as follows:

[0554] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%475(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0555] The device performance of the organic electroluminescent device D79 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 528nm, a half-peak width of 26nm, CIE color coordinates (x, y) = (0.26, 0.58), and an external quantum efficiency EQE of 39.6% (driving voltage is 2.7V).

[0556] Device Example 80

[0557] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 481. The device structure is as follows:

[0558] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%481(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0559] The D80 performance of the organic electroluminescent device prepared in this example is as follows: DC voltage is applied and the D80 of the device is measured at 10 cd / m 2 The characteristics of the light emission are yellow light with a wavelength of 578nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.57, 0.42), and an external quantum efficiency EQE of 35.3% (driving voltage is 2.5V).

[0560] Device Example 81

[0561] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 487. The device structure is as follows:

[0562] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%487(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0563] The device performance of the organic electroluminescent device D81 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2The characteristics of the light emission are sky blue light emission with a wavelength of 490nm, a half-peak width of 27nm, CIE color coordinates (x, y) = (0.16, 0.23), and an external quantum efficiency EQE of 32.4% (driving voltage is 2.6V).

[0564] Device Example 82

[0565] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 493. The device structure is as follows:

[0566] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%493(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0567] The device performance of the organic electroluminescent device D82 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 563nm, a half-maximum width of 30nm, CIE color coordinates (x, y) = (0.54, 0.67), and an external quantum efficiency EQE of 33.6% (driving voltage is 2.5V).

[0568] Device Example 83

[0569] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 499. The device structure is as follows:

[0570] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%499(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0571] The device performance of the organic electroluminescent device D83 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 531nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.24, 0.57), and an external quantum efficiency EQE of 36.9% (driving voltage is 2.6V).

[0572] Device Example 84

[0573] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 505. The device structure is as follows:

[0574] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%505(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0575] The performance of the organic electroluminescent device D84 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 553nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.23, 0.67), and an external quantum efficiency EQE of 37.2% (driving voltage is 2.6V).

[0576] Device Example 85

[0577] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 511. The device structure is as follows:

[0578] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%511(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0579] The performance of the organic electroluminescent device D85 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 544nm, a half-peak width of 25nm, CIE color coordinates (x, y) = (0.25, 0.75), and an external quantum efficiency EQE of 37.3% (driving voltage is 2.6V).

[0580] Device Example 86

[0581] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 516. The device structure is as follows:

[0582] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%516(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0583] The performance of the organic electroluminescent device D86 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2The characteristics of the light emission are blue light emission with a wavelength of 457nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.13, 0.10), and an external quantum efficiency EQE of 30.6% (driving voltage is 2.6V).

[0584] Device Example 87

[0585] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 525. The device structure is as follows:

[0586] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%525(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0587] The device performance of the organic electroluminescent device D87 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are yellow-green light emission with a wavelength of 569nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.54, 0.64), and an external quantum efficiency EQE of 36.3% (driving voltage is 2.5V).

[0588] Device Example 88

[0589] The preparation method is the same as that of device embodiment 1, except that the dye used in the light-emitting layer is replaced by 530. The device structure is as follows:

[0590] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%530(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0591] The performance of the organic electroluminescent device D88 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of light emission are green light with a wavelength of 551 nm, a half-peak width of 28 nm, CIE color coordinates (x, y) = (0.24, 0.74), and an external quantum efficiency EQE of 35.4% (driving voltage is 2.7 V).

[0592] Device Example 89

[0593] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 536. The device structure is as follows:

[0594] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%536(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0595] The device performance of the organic electroluminescent device D89 prepared in this example is as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are sky blue light emission with a wavelength of 494nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.15, 0.07), and an external quantum efficiency EQE of 32.8% (driving voltage is 2.5V).

[0596] Device Example 90

[0597] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 537. The device structure is as follows:

[0598] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%537(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0599] The performance of the organic electroluminescent device D98 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 550nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.42, 0.58), and an external quantum efficiency EQE of 28.6% (driving voltage is 2.7V).

[0600] Device Example 91

[0601] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 538. The device structure is as follows:

[0602] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%538(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0603] The performance results of the organic electroluminescent device D99 prepared in this example are as follows: DC voltage is applied and the 10 cd / m 2The characteristics of light emission are green light with a wavelength of 526nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.34, 0.64), and an external quantum efficiency EQE of 29.6% (driving voltage is 2.6V).

[0604] Device Example 92

[0605] The preparation method is the same as that of device example 1, except that the dye used in the light-emitting layer is replaced by 540. The device structure is as follows:

[0606] ITO / HI(10nm) / HT(30nm) / EBL(10nm) / Host:3wt%540(30nm) / HBL(10nm)ET(30nm) / LiF(0.5nm) / Al(150nm)

[0607] The performance of the organic electroluminescent device D100 prepared in this example was measured as follows: a DC voltage was applied and the luminous flux of 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 486nm, a half-peak width of 30nm, CIE color coordinates (x, y) = (0.13, 0.35), and an external quantum efficiency EQE of 30.7% (driving voltage is 2.7V).

[0608] Comparative Device Example 1

[0609] The preparation method is the same as that of device example 1, except that the compound 1 of the present invention used in the light-emitting layer is replaced by the compound P1 in the prior art. The specific device structure is as follows:

[0610] ITO / HI(10nm) / HT(40nm) / Host:3wt%P1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0611] The device performance results of the organic electroluminescent device DD1 prepared in this example are as follows: when a DC voltage is applied and the characteristics of the light emission at 10 cd / m2 are measured, blue light emission with a wavelength of 459 nm, a half-peak width of 28 nm, CIE color coordinates (x, y) = (0.13, 0.09), and an external quantum efficiency EQE of 13.5% can be obtained (driving voltage is 3.6 V).

[0612] Comparative Device Example 2

[0613] The preparation method is the same as that of device example 2, except that the compound 1 of the present invention used in the light-emitting layer is replaced by the compound P1 in the prior art. The specific device structure is as follows:

[0614] ITO / HI(10nm) / HT(40nm) / Host:3wt%P1(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0615] The device performance of the organic electroluminescent device DD2 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 460nm, a half-peak width of 28nm, CIE color coordinates (x, y) = (0.13, 0.09), and an external quantum efficiency EQE of 18.4% (driving voltage is 3.3V).

[0616] Comparative Device Example 3

[0617] The preparation method is the same as that of device example 1, except that the compound 1 of the present invention used in the light-emitting layer is replaced by the compound P2 in the prior art. The specific device structure is as follows:

[0618] ITO / HI(10nm) / HT(40nm) / Host:3wt%P2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0619] The device performance results of the organic electroluminescent device DD1 prepared in this example are as follows: when a DC voltage is applied and the characteristics of the luminescence at 10 cd / m2 are measured, green luminescence with a wavelength of 519 nm, a half-peak width of 38 nm, CIE color coordinates (x, y) = (0.27, 0.69), and an external quantum efficiency EQE of 19.5% can be obtained (driving voltage is 2.6 V).

[0620] Comparative Device Example 4

[0621] The preparation method is the same as that of device example 2, except that the compound 1 of the present invention used in the light-emitting layer is replaced by the compound P2 in the prior art. The specific device structure is as follows:

[0622] ITO / HI(10nm) / HT(40nm) / Host:3wt%P2(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0623] The device performance of the organic electroluminescent device DD2 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are green light with a wavelength of 519 nm, a half-peak width of 38 nm, CIE color coordinates (x, y) = (0.27, 0.69), and an external quantum efficiency EQE of 25.5% (driving voltage is 2.5 V).

[0624] Comparative Device Example 5

[0625] The preparation method is the same as that of device example 1, except that the compound 1 of the present invention used in the light-emitting layer is replaced by the compound P3 in the prior art. The specific device structure is as follows:

[0626] ITO / HI(10nm) / HT(40nm) / Host:3wt%P3(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0627] The device performance results of the organic electroluminescent device DD1 prepared in this example are as follows: when a DC voltage is applied and the characteristics of the luminescence at 10 cd / m2 are measured, blue luminescence with a wavelength of 459 nm, a half-peak width of 29 nm, CIE color coordinates (x, y) = (0.13, 0.12), and an external quantum efficiency EQE of 12.5% ​​can be obtained (driving voltage is 3.4 V).

[0628] Comparative Device Example 6

[0629] The preparation method is the same as that of device example 2, except that the compound 1 of the present invention used in the light-emitting layer is replaced by the compound P3 in the prior art. The specific device structure is as follows:

[0630] ITO / HI(10nm) / HT(40nm) / Host:3wt%P3(30nm) / ET(30nm) / LiF(0.5nm) / Al(150nm)

[0631] The device performance of the organic electroluminescent device DD2 prepared in this example is measured as follows: DC voltage is applied and the 10 cd / m 2 The characteristics of the light emission are blue light emission with a wavelength of 459nm, a half-maximum width of 29nm, CIE color coordinates (x, y) = (0.13, 0.12), and an external quantum efficiency EQE of 12.5% ​​(driving voltage is 3.3V).

[0632] The structural formulas of the various organic materials used in the above embodiments are as follows:

[0633]

[0634]

[0635]

[0636] The specific performance data of the organic electroluminescent devices D1 to D16 and devices DD1 and DD2 prepared in the above device embodiments are shown in Table 1 below.

[0637] Table 1:

[0638]

[0639]

[0640]

[0641]

[0642]

[0643]

[0644] The experimental data above demonstrate that the compounds of the present invention significantly simplify the introduction of B by introducing polar covalent bonds into the B and N molecular backbones exhibiting multiple resonance (MR) effects. This polar bond significantly simplifies the B introduction process while retaining the MR effect when B and N are in the para position, thus expanding the narrow-band emission molecular backbone system. Compared to existing MR-TADF materials, this series of materials offers simpler synthesis, with reaction yields exceeding 90%. Furthermore, the molecular fluorescence spectra exhibit a full width at half maximum (FWHM) of only 26-32 nm, a PLQY >90%, and high brightness. These materials significantly enrich the material system for multiple resonance-thermally activated delayed fluorescence (MR-TADF) and have promising application prospects.

[0645] Although the present invention has been described in conjunction with the embodiments, the present invention is not limited to the above embodiments. It should be understood that under the guidance of the concept of the present invention, those skilled in the art may make various modifications and improvements. The appended claims summarize the scope of the invention.

[0646] Obviously, the above embodiments are merely examples for clarity of explanation and are not intended to limit the implementation methods. Those skilled in the art will readily appreciate that other variations or modifications based on the above descriptions are possible. It is not necessary and impossible to enumerate all implementation methods here. Obvious variations or modifications arising therefrom remain within the scope of protection of the present invention.

Claims

1. A compound of the general formula, as shown in the following formula (1): In formula (1), the dotted line represents connection or non-connection; Ring A, Ring B, Ring C, Ring D, Ring E and Ring F are each independently selected from a benzene ring; X 2 and X 4 are independently NR1, BR2, O or S, X 1 and X 3 Each independently represents one of NR1, BR2, a single bond, O, S, S(=O)2, and C=O; n1, n2, n3 and n4 are each independently 0 or 1; R1 and R2 are each independently selected from unsubstituted or R x One of the following groups substituted: methyl, ethyl, n-propyl, tert-butyl, cyclohexyl, trifluoromethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, tetracenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenylene, quaternary, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroisotrimerized indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo thienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl oxazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 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, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, or a combination of two of the above substituents; R x One selected from the group consisting of deuterium, halogen, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C6-C30 aryloxy, and C5-C30 monocyclic heteroaryl; R1 and R2 are each independently not connected to the adjacent ring A, ring C, ring D or ring F, or are fused to form a ring through a single bond, -O- or -S- bond; R a 、R b 、R c 、R d 、R e 、R f Each independently represents a single substituent to the maximum permissible substituent, and is independently selected from hydrogen, deuterium, or one of the following groups, which are substituted or unsubstituted: halogen, C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, adamantyl, silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 condensed ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, C5-C60 condensed ring heteroaryl; the R a 、R b 、R c and R d The adjacent two are not connected or are fused into a ring through a single bond, -O- or -S-bond; When the above R a 、R b 、R c 、R d 、R e 、R f When substituents are present, the substituents are independently selected from one of deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylsilyl, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 condensed-ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, and C5-C60 condensed-ring heteroaryl. Formula (1) does not include the following compounds:

2. The compound of the general formula according to claim 1, wherein: X 1 、X 2 、X 3 、X 4 Two of them are BR2 and the other two are NR1; Or, X 1 、X 2 、X 3 、X 4 Two of them are BR2, and the other two are O; Or, X 1 、X 2 、X 3 、X 4 Two of them are BR2 and the other two are S; Or, X 1 、X 2 、X 3 、X 4 Two of them are BR2, one is NR1, and the other is O; Or, X 1 、X 2 、X 3 、X 4 One of them is BR2, two are NR1, and the other is O; Or, X 1 、X 2 、X 3 、X 4 Two of them are NR1 and the other two are single bonds; Or, X 1 、X 2 、X 3 、X 4 Two of them are O and the other two are single bonds.

3. The compound of the general formula according to claim 1, as shown in any one of the following formulas (2) to (4): In formula (2) to formula (4), X 1 、X 2 、X 3 、X 4 、R a 、R b 、R c 、R d 、R e 、R f 、R g and R x The definitions of are the same as those in formula (1); X 5 and X 6 are each independently a single bond, -O- or -S-, and n5 and n6 are each independently 0 or 1.

4. The compound of the general formula according to claim 3, wherein: In formula (2), X 5 and X 6 All are single bonds, X 1 、X 3 All are single bonds; or X 5 and X 6 All are single bonds, X 1 、X 3 All are O; or X 5 and X 6 All are single bonds, X 1 、X 3 One is NR1 and the other is BR2; or X 5 and X 6 All O, X 1 、X 3 All are NR1; or X 5 and X 6 All O, X 1 、X 3 All are BR2; In formula (3), X 6 is a single bond, X 2 O, X 1 、X 3 All are single bonds; or X 6 is a single bond, X 2 O, X 1 、X 3 All are O; or X 6 is a single bond, X 2 O, X 1 、X 3 One is NR1 and the other is BR2; or X 6 O, X 2 S, X 1 、X 3 All are NR1; or X 6 O, X 2 S, X 1 、X 3 All are BR2; In formula (4), X 2 and X 4 All O, X 1 、X 3 All are single bonds; or X 2 and X 4 All O, X 1 、X 3 All are O; or X 2 and X 4 All O, X 1 、X 3 One is NR1 and the other is BR2; or X 2 and X 4 All are S, X 1 、X 3 All are NR1; or X 2 and X 4 All are S, X 1 、X 3 All are BR2.

5. According to the general formula compound described in any one of claims 1 to 4, said R a 、R b 、R c 、R d 、R e 、R f and R g are independently selected from hydrogen, deuterium or one of the following substituted or unsubstituted substituents: 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, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, tetraphenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenylene, quaternaryl, fluorenyl, spirobifluorenyl, dihydro Phenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroistrimerized indenyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl , benzoxazolyl, naphthoxazolyl, anthraxazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 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, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidinyl, methoxy, or a combination of two of the above substituents; When the above-mentioned groups have substituents, the substituents are independently selected from any one of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy or thioalkoxy, C1-C10 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic hydrocarbon or condensed aromatic hydrocarbon group, C3-C30 monocyclic heteroaromatic hydrocarbon or condensed heteroaromatic hydrocarbon group.

6. According to the general formula compound described in any one of claims 1 to 4, said R a 、R b 、R c 、R d 、R e 、R f and R g are independently selected from hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, tert-butyl, cyclohexyl, trifluoromethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, biphenyl, phenylene, terphenyl, triphenylene, quaternaryl, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl, pyrrolyl, isoindolyl , carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthioimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, pyrimidinyl, benzopyrimidinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl azapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, azacarbazolyl, benzocarbolyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-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, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrolyl, piperidinyl or methoxy.

7. The compound of any one of claims 1 to 4, wherein R1 and R2 are independently selected from the group consisting of methyl, ethyl, n-propyl, tert-butyl, cyclohexyl, trifluoromethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, triphenylenyl, pyrenyl, biphenyl, phenylene, terphenylene, tripolyphenylene, quaterphenylene, fluorenyl, spirobifluorenyl, furanyl, benzofuranyl, thienyl, benzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, pyrimidinyl, benzopyrimidinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6 -diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazole oxazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, triarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrolyl, piperidinyl or methoxy.

8. A compound of the general formula selected from the following compounds:

9. Use of the compound according to any one of claims 1 to 8 as a functional material in an organic electronic device, wherein the organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper; 10. Use of the compound according to claim 9 as a light-emitting layer material in an organic electroluminescent device.

11. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, characterized in that: The organic layer comprises at least one luminescent material according to any one of claims 1 to 8.

Images