Organic compound, light emitting device, and display panel

Abstract

The invention relates to an organic compound, a light-emitting device and a display panel, the structural formula of the organic compound is # imgabs0, a deuterated aromatic ring is connected with benzanthracene and benzofurophenanthrene groups, when the compound is used as a main body material of a light-emitting layer, the compound has dark blue fluorescence emission, the light-emitting efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] This application relates to the field of display technologies, and particularly to an organic compound, a light-emitting device, and a display panel. Background Art

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

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic electroluminescent element utilizing the organic electroluminescence phenomenon typically has a structure including a positive electrode and a negative electrode, and an organic layer therebetween. To improve the efficiency and lifespan of the organic electroluminescent element, the organic layer has a multi-layer structure, and each layer contains different organic substances. Specifically, it may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic layer, and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons transition back to the ground state. Such an organic electroluminescent element has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast ratio, and high responsiveness.

[0004] Currently, various light-emitting layer material systems based on fluorescence and phosphorescence have been developed. For both fluorescent materials and phosphorescent materials, the development of excellent blue light materials is a huge challenge. Generally speaking, the organic light-emitting diodes using current blue fluorescent materials have higher reliability. Currently, most blue fluorescent materials adopt the method of doping a guest material into a host material, and the host material has a great influence on the luminescence quality, service life, and luminescence efficiency. When the currently used host materials are applied to the light-emitting layer of an organic light-emitting device, their color purity is poor, which is not conducive to emitting deep blue light. Moreover, their poor luminescence efficiency also affects the device power consumption and display effect. At the same time, the stability of OLEDs using such blue light-emitting layer host materials needs to be further improved to enhance the service life of the device. Summary of the Invention

[0005] Embodiments of this application provide an organic compound, a light-emitting device, and a display panel, which can not only emit deep blue light, but also further improve their luminescence efficiency and service life.

[0006] To achieve the above object, according to the first aspect of this application, an organic compound is provided, and its structural formula is shown as formula (1), (2), or (3):

[0007]

[0008] Among them, R1 to R4 are selected from one or more combinations of H, D, alkyl groups having 1 to 20 C atoms, alkoxy groups having 1 to 20 C atoms, thioalkoxy groups having 1 to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aryloxycarbonyl groups having 7 to 20 C atoms, cyano groups, carbamoyl groups, halocarbonyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, amino groups, CF3, Cl, Br, F, I, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, substituted or unsubstituted aryloxy groups having 5 to 60 ring atoms, and substituted or unsubstituted heteroaryloxy groups having 5 to 60 ring atoms;

[0009] a is an integer from 0 to 6; b is an integer from 0 to 4; c is an integer from 0 to 8; d is an integer from 0 to 3;

[0010] Ar1 and Ar2 are selected from one or more combinations of substituted or unsubstituted aromatic groups having 6 to 14 ring atoms and substituted or unsubstituted heteroaromatic groups having 6 to 14 ring atoms.

[0011] Optionally, the Ar1 and the Ar2 include any one of the following structural formulas:

[0012]

[0013] X is selected from CR5 or N;

[0014] Y is selected from NR6, CR6R7, SiR6R7, O, S, S=O or SO2;

[0015] R5 - R7 are selected from one or more combinations of H, D, alkyl groups having 1 to 20 C atoms, alkoxy groups having 1 to 20 C atoms, thioalkoxy groups having 1 to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aryloxycarbonyl groups having 7 to 20 C atoms, cyano groups, carbamoyl groups, halocarbonyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, amino groups, CF3, Cl, Br, F, I, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, substituted or unsubstituted aryloxy groups having 5 to 60 ring atoms, and substituted or unsubstituted heteroaryloxy groups having 5 to 60 ring atoms.

[0016] Optionally, Ar1 and Ar2 are selected from any one of the following structural formulas:

[0017]

[0018] Optionally, Ar1 and Ar2 are selected from at least one of the structures shown in A1 to A7:

[0019]

[0020] Among them, * represents the connection site.

[0021] Optionally, the organic compound is selected from any one of the compounds represented by Formula I-1 to Formula I-16:

[0022]

[0023]

[0024] In the second aspect of the present application, a light-emitting device is provided, including a first electrode, a second electrode, and an organic functional layer located between the first electrode and the second electrode, and the material of the organic functional layer includes at least one of the above organic compounds.

[0025] Optionally, the organic functional layer includes a light-emitting layer, the material of the light-emitting layer includes a host material and a guest material, the host material is selected from at least one of the organic compounds, and the guest material is selected from at least one of the compounds represented by Formula II:

[0026]

[0027] Among them, Ar 3 -Ar 7 is selected from at least one or a combination of more than one of a substituted or unsubstituted aromatic group having 6 to 60 ring atoms and a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.

[0028] Optionally, the Ar 3 , the Ar 4 , the Ar 5 , the Ar 6 and the Ar 7 are selected from any one of the following structural formulas:

[0029]

[0030] Among them, V is selected from CR8 or N;

[0031] W is selected from NR9, CR9R 10 , SiR9R 10, O, S, S=O or SO2;

[0032] R8-R 10 selected from one or more combinations of H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms.

[0033] Optionally, the guest material is selected from at least one of the following compounds:

[0034]

[0035] The third aspect of the present application provides a display panel including the above-mentioned light-emitting device.

[0036] In the organic compound, light-emitting device and display panel provided by the present application, the compound connects a deuterated aromatic ring to a benzanthracene and a benzofurophenanthrene group. When the compound is used as the host material of the light-emitting layer, it has a fluorescence emission with a short-wavelength emission wavelength, and its emission spectrum shows a narrow full width at half maximum. Therefore, this type of substance has a deep blue fluorescence emission. Moreover, due to the introduction of the benzanthracene and benzofurophenanthrene groups, the rigidity increases, the molecular weight increases, and the degree of molecular distortion increases, so the light-emitting efficiency of the device can be improved and the device life can be extended, while the deuterated aromatic ring helps to further improve the light-emitting efficiency.

[0037] Other features and advantages of the present application will be described in detail in the following specific implementation section. Description of the Drawings

[0038] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative efforts.

[0039] In order to more fully understand the present application and its beneficial effects, the following will be described in conjunction with the drawings, where the same reference numerals in the following description represent the same parts.

[0040] Figure 1 Schematic diagram of a light-emitting device provided for an embodiment of the present application.

[0041] Reference numerals in the drawings: 100, light-emitting device; 10, substrate; 20, anode; 30, hole injection layer; 40, hole transport layer; 50, light-emitting layer; 60, electron transport layer; 70, cathode. Detailed implementation manners

[0042] Next, the technical solutions in the embodiments of the present application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present application.

[0043] In the present application, composition, printing ink, and ink have the same meaning and can be used interchangeably.

[0044] In the present application, aromatic group, aromatic, and aromatic ring system have the same meaning and can be used interchangeably.

[0045] In the present application, heteroaromatic group, heteroaromatic, and heteroaromatic ring system have the same meaning and can be used interchangeably.

[0046] In the present application, "substituted" means that a hydrogen atom in the substituent is replaced by a substituent. "Substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. When the defined group is substituted, it should be understood that it is optionally substituted by a group acceptable in the art, including but not limited to an alkyl group having 1 to 30 carbon atoms, a heterocyclic group having 3 to 20 ring atoms, an aryl group having 5 to 20 ring atoms, a heteroaryl group having 5 to 20 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halocarbonyl group, a formyl group, -NRR', a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, a nitro group, or a halogen, and the above groups can also be further substituted by a substituent acceptable in the art; it is understandable that R and R' in -NRR' are substituted by a group acceptable in the art, including but not limited to H, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 ring atoms, a heterocyclic group having 3 to 8 ring atoms, an aryl group having 5 to 20 ring atoms, or a heteroaryl group having 5 to 10 ring atoms, and the above groups can be further substituted by one or more of the following groups: an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 ring atoms, a heterocyclic group having 3 to 8 ring atoms, a halogen, a hydroxyl group, a nitro group, or an amino group.

[0047] In the present application, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple Rs 1 , then R 1 can be independently selected from different groups. For example, when all 6 carbon atoms on the benzene ring are bonded to R 1 , the 6 Rs on the benzene ring1 may be the same as or different from each other. Moreover, the number of substituents satisfies the substitution rules. For example, in which o represents the number of substituents, and o can be selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, while in [another case], o can be selected from 0, 1, 2, 3, 4, 5 or 6.

[0048] In the present application, "the number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself in a structural compound obtained by bonding atoms into a ring (e.g., monocyclic compound, fused-ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by substituents, the atoms contained in the substituents are not included in the ring-forming atoms. The same applies to "the number of ring atoms" described below without special explanation. For example, the number of ring atoms in a benzene ring is 6, the number of ring atoms in a naphthalene ring is 10, and the number of ring atoms in a thiophenyl group is 5.

[0049] In the present application, an aromatic ring system or an aromatic group refers to a hydrocarbon group containing at least one aromatic ring, including monocyclic groups and polycyclic ring systems. A heteroaromatic ring system or a heteroaromatic group refers to a hydrocarbon group (containing heteroatoms) containing at least one heteroaromatic ring, including monocyclic groups and polycyclic ring systems. The heteroatoms are preferably selected from Si, N, P, O, S and / or Ge, and particularly preferably selected from Si, N, P, O and / or S. These polycyclic rings can have two or more rings, in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. Among these polycyclic ring species, at least one is aromatic or heteroaromatic. In the present application, an aromatic group or a heteroaromatic group includes not only a system of an aromatic group or a heteroaromatic group, but also, a plurality of aromatic groups or heteroaromatic groups can be interrupted by short non-aromatic units (<10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Therefore, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, etc. are also considered aromatic groups in the present application.

[0050] Specifically, examples of aromatic groups include: benzene, naphthalene, anthracene, phenanthrene, coronene, tetracene, pyrene, benzopyrene, triphenylene, naphthaceneacenaphthene, fluorene and their derivatives.

[0051] Specifically, examples of heteroaromatic groups include: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thiophenopyrrole, thiophenothiophene, furanopyrrole, furanofuran, thiophenofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, perimidine, quinazoline, quinazolinone and their derivatives.

[0052] In the present application, "alkyl" may represent a straight-chain, branched-chain, and / or cyclic alkyl group. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0053] In the present application, "alkoxy" may represent a straight-chain, branched-chain, and / or cyclic alkoxy group.

[0054] In the present application, "thioalkoxy" may represent a straight-chain, branched-chain, and / or cyclic thioalkoxy group.

[0055] In the present application, "*" connected to a single bond represents a connection site or a fusion site.

[0056] In the present application, when the connection site of a group is not specified, it means that any optional connection site in the group can be used as the connection site.

[0057] In the present application, when the fusion site of a group is not specified, it means that any optional fusion site in the group can be used as the fusion site. Preferably, two or more sites adjacent to each other in the group are fusion sites.

[0058] In the present application, a single bond to which a substituent is attached passes through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring. For example, in which R is connected to any substitutable site of the benzene ring, means Can be used with The benzene rings are optionally fused to form a ring, preferably adjacent C atoms on the benzene rings.

[0059] In this application, the triplet energy level ET1, the highest occupied molecular orbital energy level HOMO, and the lowest unoccupied molecular orbital energy level LUMO play a key role in the energy level structure of organic materials. The following is an introduction to the determination of these energy levels.

[0060] HOMO and LUMO energy levels can be measured using the photoelectric effect, such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy), or cyclic voltammetry (CV). Recently, quantum chemical methods, such as density functional theory (DFT), have also become effective methods for calculating molecular orbital energy levels.

[0061] The triplet energy level ET1 of an organic material can be measured by low-temperature time-resolved luminescence spectroscopy or calculated by quantum simulation (e.g., time-dependent DFT). For example, it can be calculated using the commercial software Gaussian09W (Gaussian Inc.). For specific simulation methods, see WO2011141110 or the methods described in the Examples below.

[0062] It should be noted that the absolute values of HOMO, LUMO, and ET1 depend on the measurement or calculation method used, and even different HOMO / LUMO values can be given for the same method and different evaluation methods. Therefore, reasonable and meaningful comparisons should be made using the same measurement method and the same evaluation method. In the description of the embodiments of this application, the values of HOMO, LUMO, and ET1 are obtained based on time-dependent DFT simulations, but this does not affect the application of other measurement or calculation methods.

[0063] Current blue-emitting host materials, typically fused-ring derivatives of anthracene, suffer from poor thermal stability and easy decomposition, resulting in a short device lifespan. Furthermore, these compounds suffer from poor color purity, making it difficult to achieve deep blue emission. Their low luminous efficiency compromises display quality, and their high production costs hinder mass production.

[0064] To solve the above problems, the first aspect of the embodiment of the present application provides a first organic compound,

[0065] Its structural formula is shown in formula (1), (2) or (3):

[0066]

[0067] Among them, R1 to R4 are selected from one or more combinations of H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms;

[0068] a is an integer from 0 to 6; b is an integer from 0 to 4; c is an integer from 0 to 8; d is an integer from 0 to 3;

[0069] Ar1 and Ar2 are selected from one or more combinations of a substituted or unsubstituted aromatic group having 6 to 14 ring atoms and a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms.

[0070] In some embodiments, a can be 0, 1, 2, 3, 4, 5, 6; b can be 0, 1, 2, 3, 4; c can be 0, 1, 2, 3, 4, 5, 6, 7, 8; d can be 0, 1, 2, 3.

[0071] In some embodiments, R1-R4 are selected from one or more combinations of H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms.

[0072] In some embodiments, R1-R4 are selected from one or more combinations of at least H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, and a phenyl group having 6 to 10 C atoms.

[0073] In some embodiments, R1-R4 are selected from H, D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl or 2-(2-methyl)butyl.

[0074] In some preferred embodiments, R1-R4 are selected from H or D.

[0075] It is understood that when multiple R1s appear, each R1 can be the same as or different from each other; when multiple R2s appear, each R2 can be the same as or different from each other; when multiple R3s appear, each R3 can be the same as or different from each other; when multiple R4s appear, each R4 can be the same as or different from each other.

[0076] In some embodiments, Ar1 and Ar2 are each independently selected from any one of the following structural formulas:

[0077]

[0078] X is selected from CR5 or N;

[0079] Y is selected from NR6, CR6R7, SiR6R7, O, S, S=O or SO2;

[0080] R5-R7 are selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of one or more thereof.

[0081] It is understood that in the present invention, when X is a connection site, X is C.

[0082] It is understood that when there are multiple R5s, each R5 can be the same as or different from each other; when there are multiple R6s, each R6 can be the same as or different from each other; when there are multiple R7s, each R7 can be the same as or different from each other.

[0083] In some embodiments, R5 - R7 are selected from at least one or a combination of more than one of H, D, a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, and a phenyl group having 6 to 10 C atoms.

[0084] In some embodiments, Ar1 and Ar2 are each selected from any one of the following structural formulas:

[0085]

[0086] In a further preferred embodiment, Ar1 and Ar2 are selected from When Ar1 and Ar2 are selected from these two groups, not only is the molecular conjugation enhanced, but the molecular weight does not increase too much.

[0087] In some embodiments, Ar1 and Ar2 are each selected from at least one of the structures shown in A1 to A7:

[0088]

[0089] Wherein, * represents the connection site.

[0090] It is understood that Ar1 and Ar2 can each contain only one or a combination of more than one of A1 to A7.

[0091] In some specific embodiments, Ar1 and Ar2 are selected from the structures shown in any one of A1 to A2:

[0092]

[0093] Further, Ar1 is selected from A1.

[0094] In some embodiments, R5 is selected from one or more combinations of H, D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl or 2-(2-methyl)butyl.

[0095] In some embodiments, the first organic compound is selected from any one of the compounds represented by Formula I-1 to Formula I-16:

[0096]

[0097]

[0098] In some embodiments, R1 to R5 are selected from one or more combinations of H, D, straight-chain alkyl groups having 1 to 10 C atoms, branched-chain alkyl groups having 3 to 10 C atoms, cyclic alkyl groups having 3 to 10 C atoms or phenyl.

[0099] In some embodiments, the first organic compound is any one of the following compounds:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] In the embodiments of the present application, D4-D 27 represents that in the above compounds, excluding the molecular formula After the number of D atoms in a part, the number of D atoms in the remaining part is 4 to 27; D4-D 29 It represents that in the above compound, after removing the number of D atoms in a part in the molecular formula, the number of D atoms in the remaining part is 4 to 29; D4-D 31 It represents that in the above compound, after removing the number of D atoms in a part in the molecular formula, the number of D atoms in the remaining part is 4 to 31.

[0109] It can be understood that the organic compounds represented by formula (1), formula (2) or formula (3) provided in the embodiments of the present application are not limited to the several kinds listed above.

[0110] In some embodiments, the above first organic compound is used in the functional layer of an electronic device, especially in an OLED device. Functional materials can be divided into hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), emission materials (EM), host materials and guest materials (such as organic dyes).

[0111] In some embodiments, the first organic compound provided in the embodiments of the present application can be used as an emission material in the emission layer of an emission device.

[0112] In a specific embodiment, the first organic compound provided in the embodiments of the present application can be used as a host material in the emission layer of an emission device.

[0113] Furthermore, the first organic compound provided in the embodiments of the present application can be used as a blue light host material in the emission layer of an emission device.

[0114] The first organic compound provided by the present application connects a deuterated aromatic ring to a benzanthracene and a benzofuranophenanthrene group. When used as the host material of the light-emitting layer, the compound has a fluorescence emission with a short-wavelength emission wavelength, and its emission spectrum shows a narrow full width at half maximum. Therefore, this type of substance has a deep blue fluorescence emission. Moreover, due to the introduction of the benzanthracene and benzofuranophenanthrene groups, the rigidity increases, the molecular weight increases, and the degree of molecular twisting increases, so the light-emitting efficiency of the device can be improved and the device life can be extended, while the deuterated aromatic ring helps to further improve the light-emitting efficiency. Further, the compound has a simple structural design and is easy to synthesize and mass-produce.

[0115] The second aspect of the embodiments of the present application provides a second organic compound, and the general formula of the second compound is shown in (4):

[0116]

[0117] Among them, L1 and L2 are each independently selected from one or more combinations of a single bond, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;

[0118] Q1 and Q2 are each independently selected from one or more combinations of an alkyl group having 1 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms;

[0119] R 11 is selected from one or more combinations of hydrogen, deuterium, an alkyl group having 1 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms;

[0120] n is an integer selected from 0 to 8.

[0121] In some embodiments, n can be 0, 1, 2, 3, 4, 5, 6, 7, 8.

[0122] In one embodiment, the second organic compound is any one of the following compounds:

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] It is understandable that the organic compounds represented by formula (4) provided in the embodiments of the present application are not limited to the several examples listed above.

[0129] In some embodiments, the above-mentioned second organic compound is used in the functional layer of an electronic device, especially in an OLED device. Functional materials can be divided into hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), emission materials (EM), host materials, and guest materials (such as organic dyes).

[0130] In some embodiments, the second organic compound provided in the embodiments of the present application can be used as an emission material in the emission layer of a light-emitting device.

[0131] In a specific embodiment, the second organic compound provided in the embodiments of the present application can be used as a host material in the emission layer of a light-emitting device.

[0132] Furthermore, the second organic compound provided in the embodiments of the present application can be used as a blue light host material in the emission layer of a light-emitting device.

[0133] The third aspect of the present application provides a mixture. The first mixture includes at least one of the above-mentioned first organic compounds and at least one of the above-mentioned second organic compounds.

[0134] The fourth aspect of the present invention provides a functional hybrid material, which includes at least one of the above-mentioned first organic compounds or the above-mentioned mixture and at least one other organic functional material. The organic functional material is selected from any one of hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), host materials, and guest materials.

[0135] It is understandable that the other organic functional materials in the functional hybrid material are other organic functional materials except for the above-mentioned first organic compounds or the above-mentioned mixture provided in the embodiments of the present application.

[0136] In some embodiments, other organic functional materials in the functional hybrid material are selected from host materials applied to the light-emitting layer. Further, other organic functional materials in the functional hybrid material are selected from blue-light host materials.

[0137] A fifth aspect of the embodiments of the present application provides a composition, comprising a first organic compound or the above mixture or the above functional hybrid material and a first organic solvent.

[0138] In some embodiments, the first organic solvent is selected from a combination of one or more of aromatic, heteroaromatic, esters, aromatic ketones, aromatic ethers, aliphatic ketones, aliphatic ethers, cycloaliphatic, olefinic compounds, borate esters, and phosphate esters.

[0139] In some embodiments, the first organic solvent is selected from aromatic or heteroaromatic-based solvents.

[0140] Examples of aromatic or heteroaromatic-based solvents suitable for the present invention include: p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0141] Examples of aromatic ketone solvents suitable for the present invention include: 1-tetralone, 2-tetralone, 2-(phenyl epoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0142] Examples of aromatic ether solvents suitable for the present invention are: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether.

[0143] It is understood that the aromatic, heteroaromatic, ketone or aromatic ether solvents of the present application should include but are not limited to the above selections.

[0144] In some preferred embodiments, the first organic solvent is selected from aliphatic ketones, such as: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-pentyl ketone, etc.

[0145] In some preferred embodiments, the first organic solvent is selected from aliphatic ethers, such as, pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.

[0146] In some preferred embodiments, the first organic solvent is selected from ester-based solvents, such as: alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkanolactone, alkyl oleate, etc.

[0147] Particularly preferred is one or a combination of more of octyl octanoate, diethyl sebacate, diallyl phthalate or isononyl isononanoate.

[0148] It is understood that the first solvent can be a single component or two or more components.

[0149] In some preferred embodiments, the composition further comprises a second organic solvent.

[0150] The second organic solvent includes one or a combination of more than one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene.

[0151] It is understood that the second organic solvent should include but is not limited to the above selections.

[0152] In some preferred embodiments, the first solvent and / or the second solvent particularly suitable for this application are solvents with Hansen solubility parameters in the following ranges:

[0153] δd (dispersion force) ranges from 17.0 to 23.2 MPa 1 / 2 and especially ranges from 18.5 to 21.0 MPa 1 / 2 ;

[0154] δp (polar force) ranges from 0.2 to 12.5 MPa 1 / 2 and especially ranges from 2.0 to 6.0 MPa 1 / 2 ;

[0155] δh (hydrogen bond force) ranges from 0.9 to 14.2 MPa 1 / 2 and especially ranges from 2.0 to 6.0 MPa 1 / 2 ;

[0156] For the composition according to this application, when selecting the first organic solvent and / or the second organic solvent, their boiling point parameters need to be considered. In the embodiments of this application, the boiling point of the first organic solvent and / or the second organic solvent ≥ 150 °C; preferably ≥ 180 °C; more preferably ≥ 200 °C; even more preferably ≥ 250 °C; most preferably ≥ 275 °C or ≥ 300 °C. Boiling points within these ranges are beneficial for preventing nozzle blockage of the inkjet print head. The first organic solvent and / or the second organic solvent can evaporate from the solvent system to form a functional material thin film.

[0157] In a preferred embodiment, the composition according to this application is a solution.

[0158] In another preferred embodiment, the composition according to this application is a suspension.

[0159] The solution or suspension may further comprise one or more components, such as: surface active compounds, lubricants, wetting agents, dispersants, water repellents, binders, etc., for adjusting viscosity, film-forming properties, improving adhesion or meeting relevant requirements related to printing techniques, such as: solvents and concentrations, viscosities, etc.

[0160] In some embodiments, the composition comprises 0.01 wt% to 10 wt% of a first organic substance, mixture or functional hybrid material; preferably 0.1 wt% to 15 wt%, more preferably 0.2 to 5 wt%, and most preferably 0.25 wt% to 3 wt%.

[0161] The sixth aspect of the present application provides the use of the above composition as a coating or printing ink in the preparation of light-emitting devices.

[0162] In some embodiments, the above composition is used to prepare light-emitting devices by printing or coating methods.

[0163] Among them, suitable printing or coating techniques include inkjet printing, letterpress printing, screen printing, dip coating, spin coating, knife coating, roller printing, reverse roller printing, lithography, flexography, rotary printing, spraying, brushing, pad printing or slot die extrusion coating, etc. The preferred ones are gravure printing, inkjet printing and inkjet printing.

[0164] The seventh aspect of the present application provides the application of the above first organic compound, second organic compound, mixture, functional hybrid material or composition in light-emitting devices, and the light-emitting devices include organic light-emitting diodes (OLEDs), organic photovoltaic cells (Organic Photovoltaics, OPV), organic light-emitting electrochemical cells (Organic Light-Emitting Electrochemical Cell, OLEEC), organic field-effect transistors (Organic Field-Effect Transistor, OFET), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors or organic plasmon emitting diodes (Organic Plasmon Emitting Diode, OPLED), etc., and OLEDs are particularly preferred.

[0165] In the embodiments of the present application, the first organic compound, second organic compound, mixture, functional hybrid material or composition is used in the light-emitting layer of OLED devices.

[0166] The eighth aspect of the embodiments of the present application provides a light-emitting device, including a first electrode, a second electrode, and an organic functional layer located between the first electrode and the second electrode. The material of the organic functional layer includes at least one of the above-mentioned first organic compounds, the above-mentioned mixture, the above-mentioned functional hybrid material, or the organic functional layer is prepared from the above-mentioned composition.

[0167] In some embodiments, the organic functional layer includes a light-emitting layer, and the material of the light-emitting layer includes a host material and a guest material. The host material is selected from at least one of the first organic compounds.

[0168] Currently, most of the blue-light guest compounds are arylvinylamine compounds. These compounds have poor thermal stability and are prone to decomposition, resulting in poor device lifetime. At the same time, these compounds have poor color purity and it is difficult to achieve deep blue light emission. Therefore, there are problems in realizing a full-color display.

[0169] In some embodiments, the guest material is selected from at least one of the compounds represented by Formula II:

[0170]

[0171] Wherein, Ar3 - Ar7 are selected from at least one or a combination of one or more of a substituted or unsubstituted aromatic group having 6 to 60 ring atoms and a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.

[0172] In some embodiments, Ar 3 、Ar 4 、Ar 5 、Ar 6 and Ar 7 include any one of the following structural formulas:

[0173]

[0174] Wherein, V is selected from CR8 or N;

[0175] W is selected from NR9, CR9R 10 、SiR9R 10 、O, S, S=O or SO2;

[0176] R8 - R 10One or more combinations selected from H, D, alkyl groups having 1 to 20 C atoms, alkoxy groups having 1 to 20 C atoms, thioalkoxy groups having 1 to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aryloxycarbonyl groups having 7 to 20 C atoms, cyano groups, carbamoyl groups, halocarbonyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, nitro groups, amino groups, CF3, Cl, Br, F, I, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, substituted or unsubstituted aryloxy groups having 5 to 60 ring atoms, and substituted or unsubstituted heteroaryloxy groups having 5 to 60 ring atoms.

[0177] In some embodiments, the guest material is selected from at least one of the following compounds:

[0178]

[0179] In some specific embodiments, the guest material is selected from at least one of the following compounds:

[0180]

[0181] It is understood that the compounds represented by Formula II may include but are not limited to the above compounds.

[0182] In some embodiments, the guest material is selected from at least one of the compounds represented by Formula III:

[0183]

[0184] Ar8 - Ar 11 One or more combinations selected from substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms and substituted or unsubstituted heteroaromatic groups containing 6 to 60 ring atoms.

[0185] In some embodiments, Ar8 - Ar 11 One or more combinations selected from substituted or unsubstituted aromatic groups containing 6 to 14 ring atoms and substituted or unsubstituted heteroaromatic groups containing 6 to 14 ring atoms.

[0186] In some embodiments, the said Ar8 - Ar 11 Comprises any of the following structures:

[0187]

[0188] Wherein:

[0189] V1 is selected from CR11 or N;

[0190] W1 is selected from NR 12 , CR 12 R 13 , SiR 12 R 13 , O, S, S═O or SO2;

[0191] R 11 -R 13 is selected from one or more combinations of H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, or an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, and a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms.

[0192] In some embodiments, R 11 -R 13 is selected from one or more combinations of H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms.

[0193] In some embodiments, R 11 -R 13 is selected from one or more combinations of H, D, a straight-chain alkyl group having 1 to 10 C atoms, a branched-chain or cyclic alkyl group having 3 to 10 C atoms, and a phenyl group having 6 to 10 C atoms.

[0194] The host material and the guest material in the embodiments of the present application can not only emit deep blue light and be applied to light-emitting devices, but also help to improve the light-emitting efficiency and extend the service life of the devices.

[0195] Specifically, the light-emitting devices provided by the embodiments of the present application include, but are not limited to, organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light-emitting electrochemical cells (OLEECs), organic field-effect transistors (OFETs), organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon-emitting diodes (OPEDs).

[0196] In a specific embodiment, the light-emitting device is an organic electroluminescent device, such as an OLED, an OLEEC, or an organic light-emitting field-effect transistor.

[0197] In a specific embodiment, the light-emitting device is an OLED device and includes a substrate, an anode, at least one light-emitting layer, and a cathode.

[0198] The substrate can be opaque or transparent. A transparent substrate can be used to fabricate a transparent light-emitting component. For example, see Bulovic et al., Nature 1996, 380, p29, and Gu et al., Appl. Phys. Lett. 1996, 68, p2606. The substrate can be rigid or flexible. The substrate can be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and of course, a substrate without surface defects is a particularly ideal choice. In some preferred embodiments, the substrate is flexible, and the material of the substrate is selected from polymer films or plastics, and its glass transition temperature Tg is above 150 °C, preferably above 200 °C, more preferably above 250 °C, and most preferably above 300 °C. In some embodiments, the material of the flexible substrate includes poly(ethylene terephthalate) (PET) and poly(ethylene 2,6-naphthalate) (PEN).

[0199] The anode can include a conductive metal, metal oxide, or conductive polymer. The anode can easily inject holes into the hole injection layer (HIL), hole transport layer (HTL), or light-emitting layer. In a specific embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving as the HIL, HTL, or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), etc. Other suitable anode materials are known, and those of ordinary skill in the art can easily select and use them. The anode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode is pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the light-emitting devices according to the present application.

[0200] The cathode may include a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL, ETL, or directly into the light-emitting layer. In some preferred embodiments, the absolute value of the difference between the work function of the cathode and the LUMO energy level or the conduction band energy level of the light-emitting substance in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer (EIL), electron transport layer (ETL), or hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as the cathode of an OLED may be used as the cathode material of the light-emitting device of the present application. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0201] The OLED may also include other functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0202] In some specific embodiments, for the structure of the light-emitting device 100, refer to Figure 1 , which includes a substrate 10, an anode 20, a hole injection layer (HIL) 30, a hole transport layer (HTL) 40, a light-emitting layer 50, an electron transport layer (ETL) 60, and a cathode 70 stacked in sequence.

[0203] In a specific embodiment, the light-emitting device of the embodiments of the present application is selected from solution-based OLEDs.

[0204] In a specific embodiment, the light-emitting layer of the light-emitting device of the embodiments of the present application is prepared from the aforementioned composition of the present application.

[0205] In some embodiments, the light-emitting device has a light-emitting wavelength between 300 and 1000 nm, preferably between 350 and 900 nm, and more preferably between 400 and 800 nm.

[0206] The present application also relates to the application of the above-mentioned light-emitting device in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, etc.

[0207] This application also relates to electronic devices including the above-mentioned light emitters, including but not limited to, display devices, lighting devices, light sources, sensors, and so on.

[0208] The light-emitting device provided by the embodiment of this application contains the first organic compound of the embodiment of this application. This compound connects a deuterated aromatic ring to a benzanthracene and a benzofuro[3,2-a]phenanthrene group. When this compound is used as the host material of the light-emitting layer, it has a fluorescence emission with a short-wavelength emission wavelength, and its emission spectrum shows a narrow full width at half maximum. Therefore, this type of substance has a deep blue fluorescence emission. Moreover, due to the introduction of the benzanthracene and benzofuro[3,2-a]phenanthrene groups, the rigidity increases, the molecular weight increases, and the degree of molecular twist increases. Therefore, the luminous efficiency of the device can be improved and the device life can be extended, while the deuterated aromatic ring helps to further improve the luminous efficiency.

[0209] The embodiment of this application also provides a display panel, which includes the above-mentioned light-emitting device.

[0210] Specifically, the display panel further includes an array substrate and a packaging layer; the light-emitting device is disposed on the array substrate and is electrically connected to the array substrate; the packaging layer covers the array substrate and the light-emitting device.

[0211] It can be understood that the array substrate is used to replace the light emission of the light-emitting device, and the packaging layer is used to protect the light-emitting device.

[0212] Specifically, the display panel further includes an optical film and a cover plate on the side of the packaging layer away from the light-emitting device, and the optical film is located between the packaging layer and the cover plate. Among them, the optical film includes at least one of a polarizer, a light conversion layer, and a color filter.

[0213] The display panel provided by the embodiment of this application contains the light-emitting device of the embodiment of this application. This light-emitting device contains a first organic compound. This compound connects a deuterated aromatic ring to a benzanthracene and a benzofuro[3,2-a]phenanthrene group. When this compound is used as the host material of the light-emitting layer, it has a fluorescence emission with a short-wavelength emission wavelength, and its emission spectrum shows a narrow full width at half maximum. Therefore, this type of substance has a deep blue fluorescence emission. Moreover, due to the introduction of the benzanthracene and benzofuro[3,2-a]phenanthrene groups, the rigidity increases, the molecular weight increases, and the degree of molecular twist increases. Therefore, the luminous efficiency of the display panel can be improved and the life of the display panel can be extended, while the deuterated aromatic ring helps to further improve the luminous efficiency. Thus, the display effect of the display panel is improved.

[0214] The present application will be described below in conjunction with preferred embodiments, but the present application is not limited to the following embodiments. It should be understood that the appended claims define the scope of the present application. Under the guidance of the inventive concept of the present application, those skilled in the art should realize that certain changes made to the embodiments of the present application will be covered by the spirit and scope of the claims of the present application. Specific Embodiments

[0216] (I) Synthesis of Organic Compounds

[0217] Synthesis of Compound 1 in Example 1

[0218] The synthetic route of Compound 1 is as follows;

[0219]

[0220] The synthesis process of Intermediate 1-3 is as follows:

[0221] Dissolve Intermediate 1-1 (10 mmol) and 1-2 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Stir at 100 °C for 6 h under a nitrogen atmosphere; after cooling, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain Intermediate 1-3 with a molar amount of 9.05 mmol and a yield of 90.5%. MS(ASAP) = 454.

[0222] It can be understood that MS(ASAP) represents the results of atmospheric pressure solids analysis probe mass spectrometry (ASAP-MS) of the compound, which is used to confirm the target product.

[0223] Synthesis of Compound 1:

[0224] Dissolve Intermediate 1-3 (10 mmol) and 1-4 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, rotary evaporate to remove most of the solvent, then extract and wash with water and separate the layers. The organic phase is purified by column chromatography and recrystallized to obtain Compound 1 with a molar amount of 8.67 mmol and a yield of 86.7%. MS(ASAP) = 727.

[0225] Synthesis of Compound 2 in Example 2

[0226] The synthetic route of Compound 2 is as follows:

[0227]

[0228] The synthetic route of Intermediate 2-2 is as follows:

[0229] Intermediate 2-1 (10 mmol), pinacol borate (60 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(OAc)2 (0.1 mmol) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, it was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 2-2, with a molar amount of 6.24 mmol and a yield of 62.4%. MS (ASAP) = 432.

[0230] The synthetic route of intermediate 2-4 is as follows:

[0231] Intermediate 2-2 (10 mmol) and 2-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, it was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 2-4, with a molar amount of 7.36 mmol and a yield of 73.6%. MS (ASAP) = 487.

[0232] The synthetic route of compound (2) is as follows:

[0233] Intermediate 2-4 (10 mmol) and 1-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, it was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain compound 2, with a molar amount of 7.36 mmol and a yield of 73.6%. MS (ASAP) = 779.

[0234] Synthesis of compound 3 in Example 3

[0235] The synthetic route of compound 3 is as follows:

[0236]

[0237] Synthesis of compound (3):

[0238] Intermediate 3-1 (10 mmol) (for the synthesis method, refer to Intermediate 2-4, the difference is that 2-3 is replaced by 2-boronic acid 7-deuterated naphthalene), 1-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, it was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain Compound 3, with a molar amount of 8.34 mmol and a yield of 83.4%. MS (ASAP) = 779.

[0239] Synthesis of Compound 4 in Example 4

[0240] The synthetic route of Compound 4 is as follows:

[0241]

[0242] Synthesis of Intermediate 4-2:

[0243] Intermediate 1-4 (10 mmol) and 4-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, it was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain Intermediate 4-2, with a molar amount of 8.94 mmol and a yield of 89.4%. MS (ASAP) = 469.

[0244] Synthesis of Intermediate 4-4:

[0245] Intermediate 4-2 (10 mmol) and 4-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, it was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, then extracted and washed with water and separated by liquid separation. The organic phase was purified by column chromatography and recrystallized to obtain Intermediate 4-4, with a molar amount of 8.33 mmol and a yield of 83.3%. MS (ASAP) = 545.

[0246] Synthesis of Intermediate 4-5:

[0247] The intermediate 4-4 (10 mmol) and pinacol borate were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(OAc)2 (0.1) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain intermediate 4-5 with a molar amount of 8.67 mmol and a yield of 86.7%. MS (ASAP) = 637.

[0248] Synthesis of Compound 4:

[0249] The intermediate 4-5 (10 mmol) and 1-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 4 with a molar amount of 7.52 mmol and a yield of 75.2%. MS (ASAP) = 777.

[0250] Synthesis of Compound 5 in Example 5

[0251] The synthetic route of Compound 5 is as follows:

[0252]

[0253] Synthesis of Intermediate 5-1:

[0254] The intermediate 1-4 (10 mmol) and 4-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Intermediate 5-1 with a molar amount of 8.71 mmol and a yield of 87.1%. MS (ASAP) = 419.

[0255] Synthesis of Intermediate 5-2:

[0256] Intermediate 5-1 (10 mmol) and 4-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 5-2 with a molar amount of 8.86 mmol and a yield of 88.6%. MS (ASAP) = 545.

[0257] Synthesis of intermediate 5-3:

[0258] Intermediate 5-2 (10 mmol) and pinacol borate were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(OAc)2 (0.1 mmol) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain intermediate 5-3 with a molar amount of 8.13 mmol and a yield of 81.3%. MS (ASAP) = 637.

[0259] Synthesis of compound (5):

[0260] Intermediate 5-3 (10 mmol) and 1-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallized to obtain compound 5 with a molar amount of 7.08 mmol and a yield of 70.8%. MS (ASAP) = 777.

[0261] Synthesis of compound 6 in Example 6

[0262] The synthetic route of compound 6 is as follows:

[0263]

[0264] Synthesis of intermediate 6-2:

[0265] Intermediate 5-1 (10 mmol) and 6-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-2 with a molar amount of 8.35 mmol and a yield of 83.5%. MS (ASAP) = 595.

[0266] Synthesis of intermediate 6-3:

[0267] Intermediate 6-2 (10 mmol) and pinacol borate were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(OAc)2 (0.1 mmol) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain intermediate 6-3 with a molar amount of 8.51 mmol and a yield of 85.1%. MS (ASAP) = 687.

[0268] Synthesis of compound (6):

[0269] Intermediate 6-3 (10 mmol) and 1-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain compound 6 with a molar amount of 7.15 mmol and a yield of 71.5%. MS (ASAP) = 827.

[0270] Synthesis of compound 7 in Example 7

[0271] The synthesis route of compound 7 is as follows:

[0272]

[0273] Synthesis of intermediate 7-1:

[0274] Intermediate 1-4 (10 mmol) and 6-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 7-1 with a molar amount of 8.19 mmol and a yield of 81.9%. MS (ASAP) = 519.

[0275] Synthesis of Intermediate 7-2:

[0276] Intermediate 7-1 (10 mmol) and 4-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 7-2 with a molar amount of 8.646 mmol and a yield of 86.4%. MS (ASAP) = 595.

[0277] Synthesis of Intermediate 7-3:

[0278] Intermediate 7-2 (10 mmol) and pinacol borate were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(OAc)2 (0.1 mmol) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 5-3 with a molar amount of 8.93 mmol and a yield of 89.3%. MS (ASAP) = 687.

[0279] Synthesis of Compound 7:

[0280] Intermediate 7-3 (10 mmol) and 1-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain Compound 7 with a molar amount of 7.83 mmol and a yield of 78.3%. MS (ASAP) = 827.

[0281] Synthesis of Compound 8 in Example 8

[0282] The synthetic route of Compound 8 is as follows:

[0283]

[0284] Synthesis of Intermediate 8-2:

[0285] Dissolve Intermediate 5-1 (10 mmol) and 8-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol). Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase is purified by column chromatography and recrystallized to obtain Intermediate 8-2 with a molar amount of 7.96 mmol and a yield of 79.6%. MS(ASAP)=495.

[0286] Synthesis of Intermediate 8-3:

[0287] Dissolve Intermediate 8-2 (10 mmol) and pinacol borate in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(OAc)2 (0.1 mmol) and potassium acetate (30 mmol). Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase is purified by column chromatography and recrystallized to obtain Intermediate 8-3 with a molar amount of 7.69 mmol and a yield of 76.9%. MS(ASAP)=587.

[0288] Synthesis of Compound 8:

[0289] Dissolve Intermediate 8-3 (10 mmol) and 1-1 (10 mmol) in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and add Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol). Stir at 100 °C for 6 h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then extracted, washed with water and separated by liquid separation. The organic phase is purified by column chromatography and recrystallized to obtain Compound 8 with a molar amount of 8.21 mmol and a yield of 82.1%. MS(ASAP)=727.

[0290] Synthesis of Compound 9 in Example 9

[0291] The synthetic route of Compound 9 is as follows:

[0292]

[0293] Synthesis of Intermediate 9-1:

[0294] Intermediate 1-4 (10 mmol) and 1-2 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Intermediate 9-1 with a molar amount of 9.06 mmol and a yield of 90.6%. MS (ASAP) = 495.

[0295] Synthesis of Intermediate 9-2:

[0296] Intermediate 9-1 (10 mmol) and pinacol borate were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(OAc)2 (0.1) and potassium acetate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Intermediate 9-2 with a molar amount of 8.93 mmol and a yield of 89.3%. MS (ASAP) = 587

[0297] Synthesis of Compound 9:

[0298] Intermediate 9-2 (10 mmol) and 9-3 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 / 2 ml), and Pd(PPh3)4 (0.1) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then the mixture was extracted, washed with water, and separated by liquid-liquid extraction. The organic phase was purified by column chromatography and recrystallization to obtain Compound 9 with a molar amount of 6.36 mmol and a yield of 63.6%. MS (ASAP) = 727.

[0299] Synthesis of Compound 10 in Example 10

[0300] The synthetic route of Compound 10 is as follows:

[0301]

[0302] Synthesis of Compound (10):

[0303] Intermediate 9-2 (10 mmol) and 10-1 (10 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain Compound 10 with a molar amount of 7.46 mmol and a yield of 74.6%. MS (ASAP) = 727.

[0304] Synthesis of Compound 11 in Example 11

[0305] The synthetic route of Compound 11 is as follows:

[0306]

[0307] Synthesis of Intermediate 11-2:

[0308] Intermediate 1-3 (10 mmol) and 11-1 (10 mmol) (the synthesis method is the same as that of Intermediate 2-4, except that 2-3 is replaced with phenylboronic acid) were dissolved in a mixed solvent of 1,4-dioxane and water (21 ml / 2 ml), and Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) were added. Under a nitrogen atmosphere, the mixture was stirred at 100 °C for 6 h. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain Intermediate 11-2 with a molar amount of 8.32 mmol and a yield of 83.2%. MS (ASAP) = 722

[0309] Synthesis of Compound (11):

[0310] Intermediate 11-2 (10 mmol) was dissolved in 10 ml of deuterated benzene and stirred at 60 °C overnight. After cooling, most of the solvent was removed by rotary evaporation, and then extraction and washing with water were carried out for liquid separation. The organic phase was subjected to column chromatography and recrystallization to obtain Compound 11 with a molar amount of 9.32 mmol and a yield of 93.2%. MS (ASAP) = 756.

[0311] 2. Preparation and Characterization of OLED Devices

[0312] (1) The energy levels of organic compound materials can be obtained through quantum calculations. For example, using TD-DFT (Time-Dependent Density Functional Theory) via Gaussian09W (Gaussian Inc.). The specific simulation method can be referred to in WO2011141110. First, the molecular geometry is optimized using the semi-empirical method "Ground State / Semi-empirical / Default Spin / AM1" (Charge 0 / Spin Singlet). Then, the energy structure of the organic molecule is calculated by the TD-DFT (Time-Dependent Density Functional Theory) method "TD-SCF / DFT / Default Spin / B3PW91" with the basis set "6-31G(d)" (Charge 0 / Spin Singlet). The HOMO and LUMO energy levels are calculated according to the following calibration formulas, and S1, T1, and the harmonic factor f(S1) are directly used.

[0313] HOMO(eV) = ((HOMO(G) × 27.212) - 0.9899) / 1.1206

[0314] LUMO(eV) = ((LUMO(G) × 27.212) - 2.0041) / 1.385

[0315] Where HOMO, LUMO, T1, and S1 are the direct calculation results of Gaussian 09W, in Hartree units. The results are shown in Table 1 below:

[0316] Table 1

[0317]

[0318]

[0319] (2) Preparation of OLED devices

[0320] The compound structures involved in the preparation of OLED devices are as follows:

[0321]

[0322] Among them, the synthesis method of BH-ref-1 refers to US20150349265 A1, the synthesis method of BH-ref-2 refers to KR2024009814 A, the synthesis method of ET refers to US20130248830 A1, the synthesis method of Liq refers to CN101514188A, and the synthesis method of BD-1 refers to CN117447497A

[0323] The preparation process of the OLED device using the above - mentioned compound will be described in detail through specific examples below. The structure of the OLED device is: ITO / anode / HIL / HTL / EML / ETL / cathode. The schematic diagram of the OLED device is as shown in Figure 1 Figure 1, where 10 is the substrate, 20 is the anode, 30 is the hole injection layer (HIL), 40 is the hole transport layer (HTL), 50 is the light - emitting layer, 60 is the electron transport layer (ETL), and 70 is the cathode.

[0324] The preparation steps of OLED - 1 are as follows:

[0325] a. Cleaning of the ITO (indium tin oxide) conductive glass substrate: Clean it using various solvents (such as one or several of chloroform, acetone, or isopropyl alcohol), and then perform ultraviolet - ozone treatment;

[0326] b. HIL (hole injection layer, 40 nm): 60 nm of PEDOT (polyethylenedioxythiophene, Clevios AI4083) is spin - coated as the HIL in a cleanroom and treated on a hot plate at 180 °C for 10 minutes;

[0327] c. HTL (hole transport layer, 20 nm): 20 nm of TFB or PVK (Sigma Aldrich, average Mn 25,000 - 50,000) is spin - coated in a nitrogen glove box. The solution used is TFB or PVK added to toluene solvent with a solution concentration of 5 mg / ml, and then treated on a hot plate at 180 °C for 60 minutes;

[0328] d. EML (organic light - emitting layer, 40 nm): The EML is spin - coated in a nitrogen glove box. The solution used is a methyl benzoate solution with different host - guest materials (the weight ratio of the host - guest is 95:5), with a solution concentration of 15 mg / ml. Then it is treated on a hot plate at 140 °C for 10 minutes. The guest structure is BD - 1, and the host uses compound 1 of Example 1.

[0329] e. Electron transport layer and cathode: Transfer the heat - treated substrate to a vacuum chamber. Then place ET and Liq in different evaporation units and co - deposit them at a ratio of 50 wt% each in a high vacuum (1×10 - 6 mbar) to form a 20 - nm electron transport layer on the light - emitting layer, and then deposit an Al cathode with a thickness of 100 nm.

[0330] f. Encapsulation: The device is encapsulated with ultraviolet - curable resin in a nitrogen glove box.

[0331] The preparation schemes of OLED-2 to OLED-11, OLED-Ref-1 and OLED-Ref-2 refer to OLED-1, with the difference that Compound 1 in Example 1 is replaced by the compounds in Table 2.

[0332] The current-voltage (J-V) characteristics of each OLED device were characterized by a characterization device, and important parameters such as efficiency, lifetime, and external quantum efficiency were recorded simultaneously. The results are shown in Table 2.

[0333] Table 2

[0334]

[0335] As can be seen from Table 2, the y value of the CIE color coordinates of the OLED-1 to OLED-11 devices is less than 0.1 compared with OLED-Ref-1 and BH-ref-2. When the y value is less than 0.1, the light color is dark blue. Therefore, compared with OLED-Ref-1 and OLED-Ref-2, the OLED-1 to OLED-12 devices can all emit dark blue light. Therefore, using any one of the organic compounds provided in Examples 1 to 11 of the present application as the host material of the light-emitting layer (EML) in a blue light-emitting device is beneficial to obtaining better color coordinates, so that the color purity of the light-emitting device is high, and dark blue light emission can be achieved.

[0336] Moreover, as can be seen from Table 2, the luminous efficiencies of the OLED-1 to OLED-11 devices are all in the range of 8.2 cd / A to 9.3 cd / A, and are much greater than the luminous efficiencies of OLED-Ref-1 and OLED-Ref-2, indicating that using any one of the organic compounds provided in Examples 1 to 11 of the present application as the host material in the light-emitting layer, the fabricated blue light devices have more excellent luminous efficiency.

[0337] In addition, as can be seen from Table 2, the service lives (LT90@1knits) of the OLED-1 to OLED-11 devices are much greater than those of OLED-Ref-1 and OLED-Ref-2, indicating that using any one of the organic compounds provided in Examples 1 to 11 of the present application as the host material in the light-emitting layer, the fabricated blue light devices have longer service lives.

[0338] Furthermore, as can be seen from Table 2, compared with OLED-4 to OLED-11, the luminous efficiency of OLED-1 to OLED-3 can be further increased to the range of 9.1 cd / A to 9.3 cd / A, and the service life is further increased to the range of 489 h to 495 h. Therefore, applying the compounds of Examples 1 to 3 to the light-emitting device can further improve the luminous efficiency and service life.

[0339] In the organic compounds and light-emitting devices provided by the present application, a deuterated aromatic ring is connected to a benzanthracene and a benzofuro[3,2-a]phenanthrene group. When this compound is used as the host material of the light-emitting layer, it has a fluorescence emission with a short-wavelength emission wavelength, and its emission spectrum shows a narrow full width at half maximum. Therefore, this type of substance has a deep blue fluorescence emission. Moreover, due to the introduction of the benzanthracene and benzofuro[3,2-a]phenanthrene groups, the rigidity increases, the molecular weight increases, and the degree of molecular twist increases, so the light-emitting efficiency of the device can be improved and the device lifetime can be extended, while the deuterated aromatic ring helps to further improve the light-emitting efficiency.

[0340] In the description of the present application, the terms "first" and "second" are only used for descriptive purposes and cannot be construed as indicating or implying relative importance or implicitly specifying the quantity of the indicated technical features. Thus, the features defined with "first" and "second" may explicitly or implicitly include one or more features. In the description of the present application, the meaning of "a plurality" is two or more, unless otherwise specifically defined.

[0341] In the above embodiments, the descriptions of the respective embodiments have their own emphases. For the parts not detailed in a certain embodiment, reference may be made to the relevant descriptions of other embodiments.

[0342] The embodiments, implementation manners and related technical features of the present application can be combined and replaced with each other without conflict.

[0343] The above are only the preferred embodiments of the present application and do not impose any form of limitation on the present application. However, any simple modification, equivalent change and modification made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application still fall within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that, Its structural formula is shown in Formula (1), (2) or (3): Wherein, R1 to R4 are selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of one or more thereof; a is an integer from 0 to 6; b is an integer from 0 to 4; c is an integer from 0 to 8; d is an integer from 0 to 3; Ar1 and Ar2 are selected from a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms, or a combination of one or more thereof.

2. The organic compound according to claim 1, characterized in that, The Ar1 and the Ar2 are selected from any one of the following structural formulas: X is selected from CR5 or N; Y is selected from NR6, CR6R7, SiR6R7, O, S, S=O or SO2; R5 to R7 are selected from H, D, an alkyl group having 1 to 20 C atoms, an alkoxy group having 1 to 20 C atoms, a thioalkoxy group having 1 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, CF3, Cl, Br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of one or more thereof.

3. The organic compound according to claim 2, characterized in that, The Ar1 and the Ar2 are selected from any one of the following structural formulas:

4. The organic compound according to claim 1 or 2, characterized in that, The Ar1 and the Ar2 are selected from at least one of the structures shown in A1 to A7: Wherein, * represents the connection site.

5. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the compounds represented by Formula I-1 to Formula I-16:

6. A light-emitting device, characterized in that, It includes a first electrode, a second electrode, and an organic functional layer located between the first electrode and the second electrode, and the material of the organic functional layer includes at least one of the organic compounds described in any one of Claims 1 to 5.

7. The light-emitting device according to claim 6, characterized in that, The organic functional layer includes a light-emitting layer, and the material of the light-emitting layer includes a host material and a guest material. The host material is selected from at least one of the organic compounds, and the guest material is selected from at least one of the compounds represented by Formula II: wherein, Ar 3 -Ar 7 is selected from at least one or a combination of a substituted or unsubstituted aromatic group having 6 to 60 ring atoms and a substituted or unsubstituted heteroaromatic group having 6 to 60 ring atoms.

8. The light-emitting device according to claim 7, wherein The said Ar 3 、The said Ar 4 、The said Ar 5 、The said Ar 6 and the said Ar 7 is selected from any one of the following structural formulas: Among them, V is selected from CR8 or N; W is selected from NR9, CR9R 10 , SiR9R 10 , O, S, S=O or SO2; R8-R 10 Selected from one or more combinations of H, D, alkyl groups having 1 to 20 C atoms, alkoxy groups having 1 to 20 C atoms, thioalkoxy groups having 1 to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aryloxycarbonyl groups having 7 to 20 C atoms, cyano groups, carbamoyl groups, halocarbonyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxy groups, nitro groups, amino groups, CF3, Cl, Br, F, I, substituted or unsubstituted aromatic groups having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, substituted or unsubstituted aryloxy groups having 5 to 60 ring atoms, and substituted or unsubstituted heteroaryloxy groups having 5 to 60 ring atoms.

9. The light-emitting device according to claim 7, characterized in that, The host material is selected from at least one of the following compounds:

10. A display panel, characterized in that, Comprising the light-emitting device according to any one of claims 6 to 9.

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